I love “the process.” I’ve always been interested in how reporters make decisions, especially the ones that can feel almost mystical from the PR side. The lede is a perfect example: how do you decide where a 5,000-word story actually begins?

In this chapter, Alex explains why a memorable anecdote is not automatically a strong lede, how he tested several different openings for his Column feature, and why the Ethiopia story ultimately won out.

The above is a screenshot. If you want to read the full Anatomy of a Feature:

Donate $50 to ALD Connect → https://aldconnect.org/donate/

Once you’ve donated, submit your confirmation here:

Get access to Anatomy of a Feature → https://tally.so/r/9qAB9K

Here’s Chapter 2: Choosing the Lede

From the feature (shortened for brevity):

Which makes it all the more notable when, in a planning session with top lieutenants this past September, he brings up the Ethiopia incident.

“I’m still traumatized,” he tells them. Then he turns to explain.

It was last summer, and Hockey was on one of his tours of African capitals to secure Column partnerships with local banks. Usually, these meetings follow a formula: the local ambassador tees up a few meetings; Hockey and team show up in suits; they field questions about how young they look, and rattle off arcane facts about the local financial system; they enjoy a formal dinner together; they close a deal with a handshake.

But this time, as soon as he sat down in the room in Addis Ababa, he could tell from his hosts’ expressions that something was very wrong. The bank leader slammed an article down in front of Hockey with a pointed question: how dare he show his face, after laundering money for drug cartels?

It might have been funny, if it wasn’t happening to him. Scrambling to read the article, Hockey realized he was looking at an opinion piece about TD Bank paying billions in fines for such malfeasance. But the article had been syndicated with the word “column” in its headline, and a bank monitoring service had flagged it as related to Column – his company.

How forthcoming was Column about the incident in Ethiopia?

The story came out while I was embedded with the company. I spent time shadowing Hockey, sitting in meetings, and collecting stories, which is where anecdotes like this tend to come from.

Having a CEO prepared to share those kinds of war stories gives a reporter material for a great yarn. Hockey actually told me several stories that might’ve made even juicier ledes, but some were off the record, so they stayed off the record.

At what point did you recognize that it could open the article?

To be candid, I debated what the lede should be. I wrote several versions of the Column story with different openings.

I shared those drafts with a handful of trusted readers, including my wife, other reporters, and a couple of people in tech. The consistent feedback was that the Ethiopia story was the most engaging opening. It also showed what made Hockey different and placed him in a situation most founders would never encounter.

In your opinion, what made it more than simply a funny anecdote?

A fun anecdote isn’t automatically a strong lede. It has to connect directly to the argument or central themes of the story.

The Ethiopia incident worked because Column’s business is deeply connected to the international movement of money and Hockey’s willingness to put boots on the ground in markets around the world. The anecdote introduced those themes while also revealing something about him.

Had Column not been so focused on international money flows, it might have appeared lower in the story, or not at all.

Introducing…

Anatomy of a Feature is a behind-the-scenes look at Alex Konrad’s “biggest feature of the year” on fintech startup Column and its founder and CEO, William Hockey.

For those unfamiliar, Hockey previously co-founded Plaid before leaving to build Column, a bootstrapped fintech infrastructure company that has quietly grown into a major player. If you haven’t read Alex’s feature on Column, I strongly encourage you to. Consider what you’d ask Alex about how the feature came to be.

Anatomy of a Feature explores why now was the right time to cover Column, the access and evidence the feature required, the importance of friction, what was left on the cutting-room floor, and much more from Alex’s perspective. The finished project spans more than 4,000 words across nine chapters.

It is the most ambitious thing I’ve published through Sorry for Cold Calling.

So rather than just hitting publish, I want to use this project to support an organization that means a lot to me: ALD Connect.

Why ALD Connect?

Something I don’t broadcast about myself: I was diagnosed with adrenoleukodystrophy (ALD) in early childhood.

It’s a rare disease with no known cure that can significantly impact quality of life. Unlike others with the same diagnosis, I’ve been incredibly lucky that ALD hasn’t greatly affected my life to this point. At the same time, I realize my reality is very, very different from so many others with ALD.

That’s why I want to use Anatomy of a Feature to raise $2,000 for ALD Connect to help fund research and improve outcomes for people affected by the disease. That means I need 40 PR professionals to join me!

Accessing the Content

So, from now until the end of September, anyone who donates $50 or more directly to ALD Connect can get immediate access to the complete Anatomy of a Feature.

Donate $50 to ALD Connect → https://aldconnect.org/donate/

Once you’ve donated, submit your confirmation here:
Get access to Anatomy of a Feature → https://tally.so/r/9qAB9K

I’ll verify the donation and send you the complete piece.

Beginning in October, I’ll release this edition of Anatomy of a Feature publicly on Sorry for Cold Calling, two chapters at a time.

So you can wait and read the entire project for free. It’ll just take a while.

Thank you to Alex for being willing to pull back the curtain. Thank you to everyone who helped me put this together. And, especially, thank you to anyone who chooses to support ALD Connect.

The short version: Ruth is thrilled to be helping shape Second Opinion’s editorial strategy and deepen its relationship with readers. She wants more questions from subscribers for her new advice column, and more tips on what’s happening in health tech.

What I found so interesting about this conversation is that Ruth contributes to two very different new media outlets. Unlike many of the independent journalists I’ve interviewed, she isn’t building a publication on her own or writing for just one place. We talked about how that compares with traditional freelancing, the different roles she plays at each outlet, and how she decides where a story belongs.

Here’s what she said before we went our separate ways.

You recently launched an advice column for Second Opinion. What has been the hardest part of getting it going? Has it been finding people willing to participate or getting readers to ask the right questions?

People have been really receptive to the concept. The harder part isn’t finding people willing to answer questions; it’s getting the questions themselves.

We’re working through a few, but I’ve seen seeded questions. As in: Someone submits a question and then suggests it be answered by a person they represent. I can spot those a mile away, and I’m not going to use them.

It also makes the process harder because someone could have a genuine question for a lesser-known person, and now I may look at it more skeptically.

The broader goal of the column is to engage Second Opinion’s community directly. What questions do our readers actually have? We have a great network of people we can tap to answer them, so why not use it?

What brings you to Las Vegas for Ai4? What about the discussion around AI in healthcare interests you most?

The opportunity to build up my sourcing among healthcare executives and the federal employees leading AI initiatives. The big conversation around AI in healthcare and modernization, more broadly, is: How are we going to do this?

Healthcare is such a regulated industry, and you’re dealing with people’s health and well-being. The industry is trying to figure out how to use AI responsibly across patient care and administrative work. At the same time, healthcare organizations operate on thin margins, so they need to see a real return on investment, and it can’t come at the expense of more physician burnout.

What’s been interesting from my conversations here is seeing both sides of that. The government is thinking about how to shape the use of AI in healthcare, while companies are exploring ways to use it to help patients engage more proactively with their health information.

It’s all still very early.

You contribute to two different new media outlets in Second Opinion and HUNTERBROOK. What has it been like having two editorial homes at the same time?

I sometimes describe myself as a fractional worker. That’s my rebrand for freelancing.

At Second Opinion, I’m helping develop the editorial strategy. I can still do the kind of reporting I was doing at POLITICO, but I also get to help build what the publication becomes.

I’ve been in this industry a long time, so getting to be hands-on and contribute ideas about editorial strategy is really exciting.

HUNTERBROOK is different. The work is longer-form and investigative, so the stories take much more time. Sometimes I’m supporting an investigation, sometimes I’m assigned something, and sometimes I’m following my own leads.

It’s a unique place. It’s nontraditional in some ways, but the editorial structure can also feel more traditional.

How do you decide whether an idea belongs at Second Opinion or HUNTERBROOK? Does each outlet give you the freedom to follow your own interests, or is there broader editorial direction shaping what you pursue?

The outlets serve very different purposes.

At Second Opinion, I’m thinking about our audience and the questions people in healthcare actually care about. We want to sit just above the day-to-day trade-publication cycle. We’re not trying to cover every individual development, but we also don’t want to be so high-level that the coverage loses its usefulness.

The goal is to deliver meaningful on-the-ground stories and insights for people working in healthcare or invested in modernizing the industry.

At HUNTERBROOK, the starting point might be a tip, a legal gray area, or a business practice that could be causing harm. Then you investigate whether there is really a story there and determine how to tell it responsibly.

Those investigations can take much longer. The biggest question is purely editorial: What story are we telling, and what reporting do we need to tell it?

What are you most excited about with the all-new Second Opinion? What can subscribers expect from you that might feel different from what came before?

The biggest challenge is time. We’re a small team, and new editorial products take time to build.

What excites me most is that Chrissy has created a real community, not just a following. At other publications, I pushed for more direct engagement with readers and rarely got the chance to do it. Chrissy wants to do that, and so do I.

A huge part of what we’re building is finding more ways to engage with readers, learning what they care about, and creating opportunities for subscribers to connect with one another.

We have a big event coming up in October. Events can help expand an audience, but we also want to go deeper with the audience we already have.

Subscribers can expect thoughtful stories and insights grounded in what people working in healthcare actually want and need to understand in order to innovate in the sector – not coverage of every announcement simply because it happened.

You’re in Las Vegas this week. Do you have any additional travel planned for August or September?

Nothing is confirmed yet. Someone is trying to get me to go to Texas, so we’ll see.

Otherwise, I expect to do more local travel for now. I may be in Philadelphia in October, and I’m planning to be in Washington, D.C., in September. A lot of East Coast travel for the time being.

I caught up with Salvador Rodriguez about The 2026 Dispatch, his World Cup Substack chronicling a trip he has been planning since 2018.

Sal has been traveling from city to city throughout the tournament, taking in the World Cup as both a fan and a Substacker, covering a sport he’s loved for as long as he can remember.

What started as a bucket-list trip became something more: a way to bring subscribers, friends, and family along for the ride.

Because this one is unique – in a great way – I’m skipping the Call Notes. All of us have experienced the World Cup in some form over the past few weeks. This felt like a fun way to relive it through someone else’s perspective.

So, here’s what Sal said when I called him back.

Where did the idea for The Dispatch come from? I’ve thought a few times throughout the tournament that we may not get another opportunity like this for decades – a World Cup across North America. Was that part of what pushed you to do it?

It goes all the way back to 2014, when my dad and I went to the World Cup in Brazil together. We had so much fun, and I think we both walked away thinking, “That’s not our last World Cup.”

I knew the U.S. had been trying to host another World Cup, and as soon as it was announced ahead of the 2018 tournament, I made the call to start saving for it. For eight years, I was saving up to do as much as I could at this World Cup.

I banked vacation days at two different jobs, and about a year ago, I started booking flights and Airbnbs.

At the same time, I started a listserv for friends and family who I knew wanted to attend the World Cup. I was giving them tips based on what I learned from going to Brazil.

Then, in late February, I got laid off.

At that point, it was like, “Damn. This sucks, but let me run some numbers.” I got a generous exit package, and I realized it would allow me to be present for the full World Cup.

So I went full force. I booked as many games as I could.

Because I already had the listserv, I went down to Guadalajara in March for one of the final qualifying matches. When I got back, I had so much to write and say to my friends that I thought, “Maybe I should stop giving this away for free. Maybe I should try a Substack.”

I thought the writing was strong, and I wanted to do it more seriously.

So I started writing group previews. When I was a kid, whenever the World Cup was about to start, I wanted to read about the favorites, the top players, the sleepers, and the storylines to follow.

I wasn’t seeing anyone else do that in the way I wanted to read it. So I thought, “I might just do this for an audience of one. Even if I don’t do the Substack, even if I get another job before the World Cup, I want to read this, so I’m going to write it.”

And then I went for it. It really was the perfect storm.

What have your subscribers responded to most? Have certain parts of the trip really connected with people?

I think people have enjoyed the analysis.

I play soccer recreationally in San Francisco as a goalkeeper. I’ve watched a lot of World Cup soccer. I know a lot of the trauma that these teams have. I understand a lot of the mistakes teams tend to repeat. And I know what it takes to win.

So I think people have enjoyed me being a huge soccer nerd and shepherding them through the tournament – what to look for, what to expect, and how to understand what’s happening.

How different is the rhythm of covering soccer compared with covering tech?

There are so many differences.

With soccer, it’s full of emotion. It’s joyful. It’s raw. It’s real.

The analysis is fascinating, especially because soccer is so different from other sports I’ve written about. In American football, the strategy is a little more obvious. In baseball, there are so many stats that help tell the story.

Soccer is not really like that. There aren’t as many stats that tell the whole story, so that has been interesting.

With technology and business, there’s really no emotion for the most part. It’s very much: Why didn’t you hit expectations? What’s up with the quarter? What’s going on with this technology? Can this be profitable? How much growth are you showing?

At the core of it, the biggest difference is the emotion.

What’s your favorite memory from the tournament so far?

It’s so hard to choose, but if I had to pick one, I would pick being in Philadelphia with my brother and my best friend.

None of us had been to Philadelphia before. We thought being there on the Fourth of July weekend, for a soccer match, during the 250th anniversary of our country, would be incredible.

We had such high expectations. We thought the match would be France versus Germany. It wasn’t. We thought we’d see France win 4-0. They didn’t. We thought it would be this awesome Fourth of July moment. It wouldn’t stop raining.

Then afterwards, we were hoping to see Mexico beat England. They did not.

So we had all these high expectations, and they didn’t really get met. And yet, we still had an absolute blast.

We were wearing our green jerseys, partying with all the other Mexicans in Philadelphia, and getting to explore this awesome urban city with so much history. It’s the birthplace of the nation, especially in the times that we’re in.

It didn’t meet our expectations, but in so many ways, it became its own version of special. To share that with my brother and my best friend was awesome.

Do you see this as a one-off adventure, or the start of a bigger lane for you? The appetite for soccer content in the U.S. only seems like it’s going to grow.

I think I’ll probably stay in journalism, and that’s my preference.

Probably within tech or business, just because that’s my forte. That’s where I have experience. I’m not necessarily married to it, but in newsrooms, it can be hard to break out of what you’ve been doing. People are often reluctant to take a chance.

Part of the draw for me in doing this was to experiment with new things, like Substack.

So many journalists go and do Substack, but there are very few who go and return to a newsroom. So in many ways, newsrooms lack knowledge and experience when it comes to Substack and what it’s all about.

I wanted to try it for myself and gain that knowledge so I could bring it back to a newsroom.

I’ve also used AI for so much of this. I’ve used it for research, editing, and brainstorming in a way that many newsrooms are reluctant to do right now for a variety of reasons.

I’d love to keep editing, whether it’s tech, business, sports, or something else.

But my priority is to find a job that allows me, as a private person, to continue writing. I think at my core, I’m a writer. And writers write, whether that’s during the day for whatever newsroom you’re working at or after work and on the weekends for whatever other project you might have in mind.

More than anything, I want something that allows me to continue to pursue, publish, and execute on that creative part of me.

Tiernan was early to the independent model, but what makes his story especially interesting is the lane he chose. While much of the financial press has concentrated on MANGOS, Tiernan has built a publication around the sizable public tech companies that still matter to investors but fall outside the media spotlight.

That made this conversation a little different from some of the others I’ve had. I’ve spent a lot of time talking to reporters and creators who are still in the early stages of building. Tiernan has been doing this for years, which means he can speak not only to why he went independent, but also to what he would have done differently with the benefit of hindsight.

And because it’s Tiernan, we also spent a good amount of time on what PR professionals need to understand when pitching earnings: What metrics matter, what separates a product announcement from a market-moving announcement, and why introductory conversations pay off long before a reporter writes.

The full transcript of our conversation is below, but if you only have time for a quick scan, check out my “Call Notes” for the points you can’t miss!

Call Notes

• The gap in enterprise reporting: Companies below the trillion-dollar threshold may not dominate CNBC segments, but they can still have tens of billions in revenue and meaningful investor interest. That is the lane Tiernan is trying to fill with The Technology Letter.

• Tiernan’s audience is broader than institutional investors: His readers include institutional investors, retail investors who do their own research, and those who mainly want stock picks. A meaningful portion of his readership is also international, with readers looking for insight into U.S.-listed equities they cannot easily access overseas.

• Analyst notes are a cheat sheet: PR professionals should look at sell-side reports from the previous quarter to understand what analysts focused on, what the company missed or beat, and what reporters like Tiernan are likely to home in on next.

• A product launch is not automatically market-moving: New features and platform updates only matter to an investor audience if the company can connect them to revenue, adoption, monetization, or another financial proof point.

You were early to the paid newsletter model, launching The Technology Letter in August 2020. What did you see in the format that traditional media was missing then?

Many major outlets no longer do enterprise reporting on sizable publicly traded tech companies with market caps below a trillion dollars. They won’t write about much beyond seven companies.

I left Barron’s in 2018, then freelanced for TheStreet. There, I couldn’t get them interested in companies like Arista Networks, Applied Materials, Lam Research Corp., Salesforce, or ServiceNow, even though these are companies with tens of billions of dollars in revenue.

They had decided there was no audience. They were pivoting to Apple, Alphabet, Amazon, Microsoft, Meta, and Tesla. Even NVIDIA wasn’t important in 2018 because it was still seen as a gaming company.

I started The Technology Letter because I felt there was a market to inform readers about investable stocks that couldn’t get coverage. There was an opening to write about the kinds of companies those publications used to cover, back when they believed readers still wanted to read about interesting public companies whose stock you could buy or short.

That used to be the domain of The Wall Street Journal and Barron’s, and it just isn’t anymore. There was a gap.

If the focus is solely on those six or seven companies, where does the diversity come from?

It’s a vicious cycle. If you present people with the same over-invested companies again and again, the audience isn’t stupid. They tune out.

As they tune out, media companies try desperately to get more stories about the same giant companies, hoping readers will feel a sense of urgency. But again, readers tune out.

I think it started with publications deciding no one would read enterprise stories anymore. Stories about smaller companies that readers might not know about. That used to be the point of a Wall Street Journal page-one story or a Marketplace story: “You don’t know this company. Let’s introduce you to it.”

Who makes up your subscriber base?

It’s three audiences, leaving out public relations professionals and executives at tech companies who also subscribe.

The first is institutional investors. That can mean hedge funds, and some are mutual fund managers.

The second is retail investors who like to do their own research. I get a lot of feedback from people who say, “Thank you for telling me about ‘X’ company. I researched them a bunch. I didn’t know about them, but it put them on my radar,” or, “I traded it this week and made money on the earnings.”

The third audience is also retail investors, but they really just want a list of stocks to buy. They’re not interested in reading articles. They say, “Give me a pick.”

My retail investor audience is split between U.S. and international readers. About 40% of the readership is international, with a heavy concentration in Europe, but I also have readers in Asia-Pacific, including Australia, Singapore, and China. They’re interested in U.S.-listed equities because they can’t get as much intel overseas.

When they hear directly from the CEOs I interview, they feel like they’re getting local insight into U.S. equities.

If you were launching The Technology Letter today, in a much more crowded newsletter ecosystem, what would you do differently?

What I would do differently is timing. When I left Barron’s in 2018, I was burnt out. I couldn’t blog anymore, so I slowed down and did freelance work for TheStreet and ZDNet, along with special projects. I waited until August 2020 to launch The Technology Letter, and I lost momentum.

A lot of readers knew me from Barron’s. I had that marquee brand behind me. If I had to do it over again, I would have gone straight from Barron’s into my own thing and started the blog immediately. I would have captured the momentum I had instead of waiting two years.

So I would say to anyone: If you’re with a marquee publication, don’t go to the beach for two years. Go directly into your own thing. Use the momentum you have. Use the name value of your major employer when you start.

You’ve covered technology through multiple hype cycles. What feels different about this AI cycle, and what feels the same? Is AI a bubble?

The problem is that we are not seeing the corporate revenue we’re supposed to see. Enterprise AI revenue is not coming through from corporate customers the way people expected.

That is a major problem for the tens, hundreds, and potentially trillions of dollars being invested in infrastructure – the picks and shovels. I think revenue will continue not to show up the way people expect, even as some of these giant AI companies eventually go public.

That is a real problem. Investors are not going to see the revenue payoff they need to justify some of these market caps.

Switching gears, how do you decide which lesser-known companies deserve attention?

Any publicly traded tech company that wants to talk is interesting because investors are interested.

Even if it’s a microcap, people want to hear from the CEO. They appreciate that access.

Sometimes, if it’s a company no one has heard of, the readers who want to do their own research will still consider it a service. You’ve helped them get started by cracking what would otherwise be a complete mystery.

They can say, “Okay, this is what the CEO thinks they’re doing. This is the strategy.” They’re interested. So, I’ll talk to anyone who’s publicly traded.

Maybe the better question is: What makes you want to talk to them again?

Given enough time, I would do that. Once you’ve written one interview, you have somewhat of an obligation to keep your readers informed.

If it’s a one-off, readers may say, “I don’t understand. You interviewed this person six months ago. They had a whole strategy. What’s going on?”

People do say that. I’ve done interviews with smaller companies, and readers will ask, “What happened? You interviewed that person about his company. How’s it going?” And I’ll say, “I don’t know. I haven’t talked to them in six months.”

That becomes a weak thing. I believe you need to make as much time as you can to stay in touch with these people and follow up on the story.

When you look at earnings results now, what metrics actually matter to you, and which ones do you think are mostly noise?

Most companies know what the Street cares about.

If you really want to be strong at that aspect of IR or PR, get the brokerage reports from the prior quarter. Look at what they featured as the thing that was missed or beat. Then you’ll know what someone like me is going to home in on.

How do you prepare for conversations?

How has the stock done? What is the revenue? Are they a $10 million company or a $100 billion company? It’s very basic. Are they profitable or not? Do they have cash flow or not? Are they covered by Street analysts?

That’s a big deal, because if you’re not covered by Street analysts, then there are no estimates. That means there isn’t something to measure every quarter.

Do you value introductory conversations?

I often suggest that.

What I usually say is: I come to the first interview with some knowledge, but not as much as I should have. So I ask them to be patient with me. I’m getting to know them.

If we talk again in 45 days when they report, I will have done a lot more work. Having the benefit of the first conversation gives me a start. Going forward, interviews two, three, and four will have more intelligent questions.

What should PR people understand about the difference between a product announcement and a market-moving announcement?

If the company doesn’t report it financially, you can’t do anything with it.

If they have agentic technology, nobody cares until they break out the financial impact. Maybe they include it regularly in the financial statement: “We have $20 million now from our new agentic line.”

Or maybe they don’t tell you every quarter, but they give you something this quarter: “We’re on track to make $70 million from this agentic feature we added on top of the license.”

It has to be something you can cite. Otherwise, we won’t care. If you say, “We just launched an agentic feature,” nobody cares.

The short version: Ron covered his ideal guest, the kinds of stories he wants to explore on the podcast, where he’ll be through the end of the summer, and why he wants to do more moderating.

Here’s what he said before we ended the call.

Who is your ideal podcast guest? Are you mostly looking for C-level executives, CEOs, or product-focused leaders?

I just started the podcast, so I’ve had some inbound interest, which has been good.

Aaron Levie of Box was my first guest. My second guest will be Don Schuerman from Pegasystems. Then, in August, I have Jeetu Patel of Cisco lined up. I’ve known Jeetu for many years, going back to when he was in marketing at EMC and I was covering content management.

Ideally, I’m thinking about four types of guests: executives, analysts, authors, and VCs.

They also, ideally, need to be people others have heard of.

From a FastForward perspective, I view the podcast, newsletter, and blog as a three-legged stool. They feed each other from a content perspective. A good podcast conversation can become a story, clips, newsletter ideas, or blog posts.

I record once a month right now, but eventually, I hope to go twice a month. It’s a lot of admin overhead for one person. I don’t have a producer reaching out to guests on my behalf. It’s just me.

Hopefully, as more people listen to the podcast and like it, I’ll get more inbound interest, and it’ll become less work on my part.

What kinds of stories or trends are you looking to cover? Should PR people reach out about news moments or company milestones?

I’m not that interested in organizational milestones.

I want to talk about the same things I’m already writing about. AI is huge, but it sucks the energy out of any other type of news.

I want to keep exploring new trends. That’s what I do, and that’s what I’ve always tried to do: stay ahead of where things are going. I’m often a little bored by the time things actually happen in the market because I’ve already been writing about them.

The conversation also has to give me something I can do more with. With Aaron, for example, he talked about the impact of AI on jobs and why he didn’t believe it would actually be negative.

Tell me about the relationship with Playaz Production Network. Why did that partnership make sense?

I’ve known Brent Leary and Paul Greenberg for many years.

They’ve typically focused on CRM, customer experience, and marketing tools types of podcasts.

My thinking in affiliating with them was simple: I’m solo, and I know very little about podcasting. I probably could have learned it, but it would have taken a long time to put this together on my own. Even when we were starting FastForward at boldstart ventures, I knew I wanted a podcast.

When Brent approached me about joining their network, it was a no-brainer. He’s also been a tremendous partner to me.

What does your travel schedule look like through the end of the summer? Where can people find you?

I’m not traveling this summer for work. I’m going to Europe on vacation for a month in July. I’ll do some writing, but in terms of podcasting, I have nothing lined up that month.

August is quiet on the conference front. But in September, I’ll be at HumanX in Amsterdam. I’ll also be at HubSpot’s annual conference in Boston. Beyond that, I’m still figuring out my schedule.

I also want to point out that I’m doing professional moderating for a fee. I did a fireside chat last week at Pax8 Beyond and a video interview with Zscaler’s Swamy Kocherlakota at their Zenith conference in Las Vegas.

I enjoyed them immensely, and I’m looking for more opportunities like that.

The short version: Sharon sees a real opening for original AI reporting focused on infrastructure, security, and policy. For PR people, the bar is high: she’s interested in the right leaders, news, and trend perspectives, not routine product news. She’s also headed to Black Hat and DEF CON later this summer.

Here’s what she said before we ended the call.

Why was now the right time for you to go independent with Ground Level AI?

For one thing, I think the timing is good for an AI reporter who has been covering the beat for more than four years. AI is an overwhelming beat, and I think there is a real opening for original journalism focused on foundational issues like infrastructure, security, and policy.

On the other hand, there is never a good time. You still have to be willing to take the leap. And I am someone who enjoys a new project and likes building things. So, it’s a good time for me.

For comms professionals, when should we be reaching out to you? Are you looking for interviews with AI leaders, market-moving news, or perspectives on trends?

I’m not typically covering product news or embargoes. I’m certainly always on the lookout for interviews with the right AI leaders, news, or trend perspectives, but I get far more than I could ever use.

I’ll definitely respond if I’m interested.

Could you see Ground Level AI becoming a podcast in the not-so-distant future?

Absolutely. That’s part of the platform plan. I hope to start the Ground Level AI podcast sometime over the summer.

What do the next few weeks look like for you? Are you traveling anywhere, attending any shows, or looking to meet with new sources?

I’m heading back to SF next week for an event, and I’ll be in Los Angeles for a bit in early August, as well as at Black Hat and DEF CON in Vegas.

I also hope to make it to Washington, D.C. this summer.

If you haven’t kept up with Jane recently, you may be surprised to know she left Bloomberg at the end of February. You may be even more surprised to know she has spent the last four years studying math and physics at The Open University. It was a decision rooted in one of the clearest lines from our conversation: “If you don’t get it, you can’t write it.”

Jane is now hard at work getting QuantumJane ready for a September launch, and I could not be more excited for her.

This conversation is different from my past interviews because QuantumJane isn’t live yet. Instead of talking about what she has already built, we spent a lot of time on why she is building it, why quantum matters to her, and why she wants to make such a technical field feel more accessible.

In many ways, QuantumJane feels like Jane returning to a curiosity she had as a kid, but with the reporting experience she possesses now to make it useful to everyone else. I hope it inspires others the same way it inspired me.

The full transcript of our conversation is below, but if you only have time for a quick scan, check out my “Call Notes” for the points you can’t miss!

Call Notes

• Jane wants to push the hockey puck forward: Institutional media often covers what’s already happened – look no further than the industry’s coverage of AI. With QuantumJane, Jane wants to decode what’s coming next in quantum.

• Why it’s time to cut the jargon: A major theme of our conversation, and QuantumJane more broadly, is accessibility. Jane does not think quantum should be protected behind jargon moats. She wants to make the space approachable for everyone, including those visiting her site for the first time.

• Understanding the ROI: Jane wants to help readers understand all aspects of the quantum ecosystem. She plans to keep CEO interviews unpaywalled, which means there is real value in helping her meet the right people and understand the right ideas. While Jane is still building, and beyond, PR people can be a resource by introducing her to useful sources and context. Her goal isn’t to push one-off news.

Tell me about QuantumJane. What are you building, and what do you hope subscribers will come to rely on it for once it launches?

I’ll dial it back to 2015. Actually, I’ll dial it back even further.

When I was a kid, I thought I would be an inventor. I grew up in Korea, and in the Korean system, it wasn’t like America, where there were lots of clubs and things to do. Back in the late ’70s and ’80s, there were no makerspaces or things like that.

When it came to math, I would often make small mistakes, things like forgetting a minus or plus sign, and occasionally my grades would be below 90 (out of 100). That sounds fine in a Western context, but in an Asian context, people would say, “What’s wrong with your math?”

When I was 14, a chemistry teacher said in passing, “If your math isn’t good, you really should go into humanities instead of STEM.” I was a little crushed. [But in the back of my mind,] I thought, “Maybe she’s right. What else can I do?”

Randomly, I decided I was going to be a broadcast journalist. People would say, “Oh, you want to be like Barbara Walters?” And I’d say, “Who’s Barbara Walters?” That’s how naive I was. I was in Korea, so why would I know Barbara Walters? But still, if someone says they’re going to be a journalist, you’d think they read the newspaper, know the personalities, or know current affairs. I knew none of it. I didn’t really care to read the newspaper. I wasn’t a news junkie. I’m still not a news junkie.

But once the goal was set, the blinders went on, and I marched straight ahead. I marched my whole life to be a journalist. I went to Columbia Journalism School, and I kept going.

But I always knew there was something off about how I became a journalist. When I was writing my application to Columbia Journalism School, there was a question: “Why do you want to be a journalist?” It took me forever to answer that. I think I might have made something up, because I didn’t know.

Then, in December 2015, I was a video journalist at Reuters and was assigned to cover D-Wave, the Canadian quantum company. They had a press conference with Google and Ames Research. To prepare for it, I had to figure out what quantum mechanics was. For the first time, I was forced to read something I had been told my whole life was only for “smart people.”

I was fascinated by it. It’s really crazy stuff. I thought, “Wow, this is so fascinating. I have to do this. What am I doing in journalism?” It was an awakening moment.

And it was Silicon Valley. It’s in the air that you can do anything you set out to do. So little by little, I started telling people I really loved [quantum] and wanted to figure out a way to do it.

Slowly, people started reaching out with quantum companies to cover. I took every one of those calls. Whether I could cover that company or not, I took the intro call and had whoever was on the call explain the technology to me. I started writing more and more.

As you know, once you write one story, there’s an avalanche of communications people reaching out with other quantum companies. It snowballed, especially because in institutional media, [so few people] really cover this stuff.

Everyone in the quantum community has also been great at explaining things.

As a journalist, you get to ask rudimentary questions without apologizing for it. If you don’t get it, you can’t write it.

Then, in 2021, a colleague of mine moved from Venezuela to the Bay Area. I was talking to her about how I was hesitating whether to stay in journalism or quit and go back to school to study physics full-time. She said, “My husband is a physicist. You should meet him. He’s also a former Reuters journalist.”

I met him, and he immediately said, “No, you have to study. You can just do it at The Open University. I’ve researched it all. This is the perfect thing for you to do.”

So I signed up. By 2022, I had started a bachelor’s degree in science at The Open University in the U.K., studying math and physics.

For the past four years, I’ve been covering as much quantum as I can. I did stories on quantum-inspired algorithms and how GPS spoofing has created demand for quantum positioning systems using quantum sensors.

But in institutional media today, it’s more about covering what happens than covering what we think will happen. We’re following the hockey puck rather than getting ahead of it.

All that is to say, I had been itching to do more quantum coverage and looking for a way to do it. What I wanted to do clashed with what I was supposed to do, or what I was paid to do.

Then, in January, my former global tech editor from Reuters was visiting Taiwan. He saw me struggling with what I wanted to do versus what I was doing. He told me, “This is such a niche area that it might actually work.” He was the founding editor of The Industry Standard, so I trust him.

A week later, I set up QuantumJane.

I want to do something that interests me, that I’m passionate about, that I have fun with, and that still challenges me. I love a challenge.

There was also a void. And I’m a little angry, because quantum physics has always been talked about as if it’s only for smart people. Especially coming from Asia and Korea, the message was: What are you doing in this pond? Go away.

At a fundamental level, yes, it’s Albert Einstein, Niels Bohr and some of the smartest minds of our time. But that doesn’t mean other people should be locked out of it. It shouldn’t be written in Latin so nobody can read it. It should be written in a way that everybody can access and understand at some fundamental level.

I want to build bridges. I want to be a translator.

You’re still in the building phase. What has surprised you most about bringing QuantumJane to life?

The biggest surprise is that I’m doing this at a time when this kind of thing is going to take off, thanks to AI.

Initially, the advice was to do Substack. But I had ideas about what I wanted QuantumJane to be. I didn’t want it to be a newsletter. The other day, someone called it a newsletter, and I said, “Oh, not a newsletter. I’m a news site.”

There are things I want to do that Substack can’t do, at least based on my initial research. I want to thread things together so that if someone comes to QuantumJane in a year and wants to know what a quantum sensor is, they can click into the topic section and see all the stories related to quantum sensors, along with the companies involved.

It’s really a place for people to come and learn for the first time. I want a page for people coming to this for the first time, with an order of things they can look at.

Another surprise is that I can do this by myself. Of course, I have a lot of support from friends and people friends have introduced me to. But with AI and the platforms that exist now, it’s possible for me to do it myself.

I’ve also been surprised by how passionate independent people are about building their own thing. Everybody is super supportive. There’s an understanding that we’re all in this together, trying to create something.

How can people in PR, founders, or researchers be helpful to you right now and after you launch?

For my purposes, I appreciate people reaching out with pitches in the quantum space.

Over the course of my career, I’ve taken every pitch that has a quantum company or quantum angle in it. I meet with all of them. If you’re willing to connect me with your clients without any expectation of an article, that’s a huge help.

I should have a huge interview lined up for the launch. If that goes well, it should get immediate traction. Then it’s up to me to deliver stories that you can’t find elsewhere and that are valuable.

CEO interviews or introductions to companies [will be free]. I think when people give me their time, those stories should also get an audience. They’re also not as labor-intensive, and they’re fun.

I love filming, video, and editing. I love meeting people and seeing things. So I’m fine with not charging for that. That’s how I’ll get people to QuantumJane.

The paid section will be well-researched news stories and explainers. And I will keep everything as short as possible. I will be a sieve of information and an explainer.

The short version: Nat is excited by AI’s potential, but she’s keeping an eye on the gap between the speed of development and the industry’s ability to govern it.

Here’s what she said before we ended the call.

What events, conferences, or trips are on your radar for the rest of the summer?

I just got done with a pretty big event season. I was in the Bay Area at least half a dozen times for NVIDIA’s GTC conference, HumanX, Temporal Replay, and most recently, Microsoft Build and Snowflake Summit.

So thankfully, I’m getting a little break from the Bay Area. I’m based in LA, so it’s not a far flight or anything, but I’m grateful to have a couple of weeks off.

The next one I have coming up is AI4 in August.

When you step back from the launches and announcements, where is your head at on AI right now?

That’s such a hard question to answer because it changes every day.

For context, all of my reporting comes through the lens of responsible and ethical AI, and the impact this technology could have broadly on businesses, individuals, society, and the way we work, think, act, and exist.

Because that’s the lens I’m approaching things from, it makes me turn a very critical eye to any announcement, initiative, product, or anything these major companies are putting forward.

There is a lot of potential in this technology. It can obviously do amazing things, and it has proven itself there. But I don’t think responsibility and considerations for safety are being put forward enough.

The excitement around the technology and its development is outrunning our ability to secure, control, and govern it. That’s largely what I’ve been hearing from sources, too. Security is talked about, but the development of the technology itself is outpacing our ability to rein it in.

For PR people trying to be helpful to you, what actually makes a pitch, intro, or event invite useful right now?

As far as sourcing, I love getting things in advance. I love embargoes and exclusives. We’ve been getting more exclusives lately, which has been very exciting for a young publication.

Any opportunity to give us something another publication doesn’t have is great, but that’s the obvious thing.

The less obvious thing is that I want to know your source’s hot take. I want to know what they’re thinking about, how they’re thinking about AI, how they’re using it in their daily lives, what they think is scary or dangerous about it, and what they find exciting.

Especially if the source is a subject-matter expert on a specific aspect of AI, I love talking to those people and really understanding where their head is at.

I caught Kelly on the phone to discuss the unique differences among all three brands, the evolution of the cybersecurity space since Dark Reading was founded almost 20 years ago, and parts of the outlet you may not have known existed.

The full transcript of the conversation can be found below, but if you only have time for a quick scan, check out our “Call Notes” for the points you can’t miss!

Call Notes

• Dark Reading’s 20th Birthday Celebration: Dark Reading is turning 20 next year, and they’re planning special coverage and other surprises to mark the milestone.

• Pitching Guide:

  • Dark Reading: Aims to be the first stop for security practitioners — from the SOC to the CISO — to discover what’s happening in their industry, what it means to their roles, and what they need to know in their daily jobs.

  • Cybersecurity Dive: Focuses on equipping C-level decision-makers with the “news of the day” to keep them informed and prepared for discussions and decisions.

  • SearchSecurity: Provides “day-three analysis,” offering deep technical guidance and tutorials on new and existing technologies to inform decision-makers.

• Cybersecurity Awareness Month: This year, the three media brands will create a special compilation that packages together work from all three brands with content around security training and awareness issues.

• Dark Reading CISO Advisory Board: This board helps Dark Reading hear directly from security leaders across multiple vertical markets. They meet quarterly, and the members inspired Dark Reading’s creation of “CISO Corner” for curated, high-priority stories. They’re always looking for new members from enterprises (not security vendors).

• Dark Reading Contributed Content is Changing: Jim Donahue retired (and he’s missed!). Senior Editor Becky Bracken is now leading this section and shifting it to an Op-Ed model. Expect fewer, but higher-quality and more strategic opinion pieces, especially from CISOs and practitioners.

• AI’s Impact on SOCs: AI isn’t going anywhere. Kelly wants to hear how it’s actually helping SOCs with things like surfacing alerts, triaging threats, reducing analyst fatigue, and streamlining response. They’re looking for practical, proven stories, not just product announcements.

The Informa Tech/TechTarget merger was announced almost a year ago now. What are some of the most noticeable changes that have taken place? Less noticeable?

Our new company is Informa TechTarget, blending three media businesses: Informa Tech, which is where Dark Reading resided; TechTarget, which was the home of SearchSecurity; and Industry Dive, which was part of Informa Tech and the home to Cybersecurity Dive.

Our group, the Cybersecurity Media Group, was one of the first in Informa TechTarget to organize around a market or industry. Other groups have come together more in the last few months, including the EIT side. But we’ve been together since January.

What struck me first about the three cybersecurity media brands is that we are really different, even though we’re in the same industry. In some ways, we’re targeting the same readers, but we really do that in very different ways.

Stepping back, first, so the readers of this know my new role. I am now the VP of the Cybersecurity Media Group, which includes Dark Reading, SearchSecurity, and Cybersecurity Dive. I am also still the editor-in-chief at Dark Reading and now Cybersecurity Dive. I have been working closely with all three brands, so I can explain how they differ and complement one another.

Dark Reading has been around since 2006. Next year will be our 20th anniversary.

Is there a 20th anniversary party coming?

We are actually working on our plans now. We held a big celebration for our tenth anniversary. Back then, we did a package of special coverage, and we plan to create something similar again. More to come — I can’t give it all away.

When Dark Reading began 20 years ago, there were not many cybersecurity publications out there. The industry was still in its infancy. Our original goal — which has not changed even after all these years — is to serve as a major media site for cybersecurity practitioners at all levels. Because at that point, the CISO role was extremely rare, and there were few security vendors. Today, there are 3,000 or so vendors, or close to that.

Dark Reading’s original strategy was to be the first stop for security practitioners to uncover what is happening in their industry and what they need to know to do their jobs every day. That has not changed. We cover news, but we look beyond the face value of the news and dig into what the news event or trend means for security professionals and what they can or should do about a new threat or issue.

We have some of the most experienced and renowned cybersecurity reporters who have been covering this industry for a long time. We know the industry really well. Our reporters possess the sources, the context, and the technical knowledge to write those kinds of stories.

Beyond news, how else can we work with the Dark Reading team?

We have two big sections in addition to our news. We have the Edge feature section, which was originally our concept of the old Sunday newspaper magazine, and is headed by Fahmida Rashid.

We also have Dark Reading Technology, also led by Fahmida. That is a space for us to dig into “game-changing” technology trends and unique product announcements.

What differentiates you from one another?

I’ll start with Cybersecurity Dive. It’s a two-person operation: Eric Geller and David Jones, who are excellent journalists. They are classic investigative reporters; that is their thing, and they have that nose for news. The Dive approach is newsletter-forward, targeting the C-level. The goal is to equip those C-level decision-makers with the news of the day so they are prepared to respond and build their strategies accordingly.

SearchSecurity is known for its deep technical guidance and tutorials. They understand, better than anyone, new and existing technologies and how they work. Sharon Shea is the Executive Editor of SearchSecurity. They are after “third day analysis,” a term coined by Sharon. For example, related to the SolarWinds attack, they published stories about preventing supply chain attacks and lessons learned from SolarWinds.

We provide the full gamut of security content for the industry, so we complement one another really well.

What changes might a day-to-day reader notice?

They probably don’t see much difference from the outside, but they might notice that we are being more strategic with our coverage or more selective.

What do you mean by strategic?

So our three brands meet together weekly. We work closely together, ensuring we know who is doing what, so we do not duplicate efforts. If we are covering the same topic or news, it will look completely different on each site. We complement each other, and each of us creates content in its own unique way, providing what I like to call a full, 360-degree view of an issue.

We also link to one another’s stories on our sites and highlight each other’s work in our individual newsletters.

What other ways do you work as a team?

The Cyber Media Team meets weekly as a group. We have our own chat on Teams together. We are also still settling into a new way of working. I think everyone is really embracing it, which is admirable, because change is so hard.

The first time we met, I confess I was nervous about how to bring the three groups together, who were all affected in different ways by this merger. Everyone was feeling the challenges of change. But right away, there was chemistry. We have a group of people who like and respect each other, and it’s showing up in the form of creative ways we work together and support one another. We now have a weekly movie trivia contest, and it has been fun for us to be able to joke around with one another and enjoy our work.

You know how Cyber Security Awareness Month sometimes gets mocked by industry insiders? We are all like, “Oh gosh, what are we gonna write about this year?” None of us writes for consumers. That was one of those moments where we all rallied together and came up with an idea for the group package.

I have my feelings about Cybersecurity Awareness Month, but I could not imagine how you and your team feel. You are fielding the pitches.

What I think is important about it is that, and something we have published in the past, exploring the perspective of why attacks are still so easy even in the age of cyber awareness training, so how are companies training their employees, given that ongoing challenge? The latter is what we want to lean into this year.

What team changes have taken place as a result of the merger?

One of the biggest strengths of our Dark Reading team is our depth. Dark Reading’s “superpower” has always been the deep-dive, investigative content that no one else produces. At the time of the merger, Dark Reading was short-staffed, and Informa TechTarget’s management was looking to ensure the three cyber brands were unique. The executive team decided to bring three writers, Arielle Waldman, Rob Wright, and Alex Culafi, from TechTarget to fill those gaps, and they have been great fits.

Arielle Waldman had a strong interest in writing features, so she moved over to work with Fahmida in our features section. She is doing exceptional work. Rob Wright supports Tara Seals on the news operation side, which is incredibly fast-paced. We publish around seven or more stories a day, so Rob has become Tara’s “right hand,” doing reporting and helping with daily editorial flow. Alex Culafi is writing excellent news analysis stories. We wanted to ensure our staff writers had the bandwidth to produce more in-depth news analysis, which we are known for, so this team expansion really helped.

Can you share more about the Dark Reading CISO Advisory Board and how to get involved?

This is a concept we had envisioned for years, but only launched in 2023 once we had the resources. The goal of the CISO Advisory Board was to ensure we are hearing from the security leaders we serve. We did not want to assume we know what CISOs need; we want to ask them. CISOs on the board serve 18-month terms, and surprisingly, almost everyone in our first cohort came back for a second term when their first term ended. And, I’m excited to say we are bringing in new members.

Today, the CISO Advisory Board is composed of CISOs from a range of company sizes and sectors, including Reddit and Con Edison, in addition to university and city government. Diversity of perspective was key from the start. We meet quarterly via Teams to share what we are working on and ask for candid feedback: What is helpful? What is missing? What do you not want to read about? One concrete outcome from those meetings was our CISO Corner. A member of the board shared they were too busy to dig through content and wanted a dedicated space with curated, high-priority stories. So we created a manually curated homepage section for them.

Beyond advising us, the board members have also participated in our podcast, virtual events, and live panels at Black Hat, giving them a voice and fostering peer-to-peer networking. And for us, it has helped us get out of our bubbles and hear from those on the front lines. That has been a huge asset to our reporting.

What are some other ways that Dark Reading has evolved to expand readership?

Historically, our platform was not set up well for video, but that has changed. We now have the tools to make video a bigger part of our content strategy.

Under the leadership of Tara Seals, our managing editor for news, Dark Reading is expanding its content strategy beyond traditional text by incorporating more video content. This includes:

• Video Sidebars in Articles: Short video clips embedded within articles.

• Video Explainers: Dedicated videos to explain complex topics.

• Social-First Video Snippets: Short, engaging videos designed for social media platforms.

• Reporters’ Notebooks: Videos featuring reporters discussing their insights (e.g., Arielle Waldman and Eric Geller on IoT Security).

• Writer Camera Embeds: Journalist intros and insights into their stories.

• CISO-Focused Video Pieces: Video interviews with CISOs run by Dark Reading’s Kristina Beek.

• Highlighting Dark Reading’s Editorial Webinar Content: Converting longer webinar content into shorter, digestible clips.

This shift aims to connect with readers, especially younger security professionals who prefer video and audio content over text.

There is also Dark Reading Confidential, our monthly podcast, which is a storytelling-style show that emphasizes stories and voices of security practitioners. Becky Bracken is the host and manager of Dark Reading Confidential.

What’s happening with contributed content now that Jim Donahue has retired?

Dark Reading is returning to the original vision for the section, which is more of a curated op-ed space. Becky Bracken is leading it now and brings fresh ideas on the types of OpEds we want to run. We will have fewer pieces, but aim for higher-profile contributors, including CISOs and practitioners. We’re focusing on strong opinion pieces. More to come as we finalize the structure, but the direction is clear: higher quality, more strategic voices.

Let’s close out with AI. How are you approaching AI coverage, and what’s top of mind for you going into 2026?

AI is not going anywhere. We are interested in how AI will reshape SOCs, including enhancing their ability to surface alerts, triage threats, reduce analyst fatigue, and streamline incident response. The “needle in the haystack” problem remains, and we want to report on where AI actually helps vs. what marketing teams say. Our readers prefer stories about what’s practical and proven, not just announcements of the latest AI product.

Editor’s note: This piece was originally published in April 2025 and is being republished here as part of the launch of Sorry For Cold Calling. Some references reflect the time it was originally written.

We spoke again recently to discuss the launch of his podcast, The Upstarts Podcast, available on Apple, YouTube, and Spotify. We covered what success looks like, growing an audience, and how he evaluates potential guests.

The full transcript of the conversation is below, but if you only have time for a quick scan, check out my “Call Notes” for the points you can’t miss!

Call Notes

• Being an Upstart: While the core remains rooted in tech entrepreneurship, the lens is widening to capture the “Upstart moments” across entertainment, sports, the arts, culinary, and other industries.

• Building for Longevity: The strategy prioritizes evergreen value over the 24-hour news cycle, ensuring a conversation recorded today remains a must-listen for builders months down the road.

• Substance Over Valuation: A massive valuation or a household name is no guarantee of a slot. The focus is on leaders who have earned the audience’s attention through a compelling, high-stakes narrative.

• The Audition for Authenticity: Every guest is vetted through past performances to ensure the medium matches the message. By avoiding the over-toured guest circuit, the show protects its commitment to fresh, untold perspectives.

Love the studio you’re using. Is your goal to do most podcasts in person? How has the experience been for you, being in-person and virtual?

I’ve found that in-studio conversations bring out a much more dynamic and engaging product.

I was lucky to get to talk to Melanie Perkins for my first episode, and she’s in Australia. So, remote made sense. I recorded another remote podcast coming out with a CEO based in Jacksonville, Andrew Rush from Star Catcher. So I have to be opportunistic and scrappy, but whenever possible, I prefer to be there in person with the guest. It’s a more naturally flowing conversation.

I’ve also found that my audience wants to feel like they’re there in the room with the guest and me.

To avoid the crashing plates scenario you described in our last interview, what do you define as success for the podcast?

I want to do this for a long time. My current objective is to earn an even bigger season two.

I’m confident that we’ll have a smooth 12-episode arc for the first season. We’ve already recorded over half of the conversations, so I’m not worried about the quality of the guests. Audience building, however, is really important. I need to engage with them so that they come back to the show, not just for the debut or a big name.

We were also lucky enough to have a presenting sponsor for the first season. I hope to excite the community enough that we have no shortage of possible sponsors for the future.

One of the best parts of Upstarts is the ability to say I’m going to do something, and actually do it, without worrying about it being perfect or needing 100 people to sign off on it.

How are you thinking about audience building?

I’m sharing the podcast in a few different places and testing what resonates regarding sharing. Every episode goes into a newsletter that I send out. I also share it on social media, and then I have clips. I’ve already gotten feedback that people want even more short clips. I have those, but I can get even better at distributing them, and those shorts building their own audience will be a good sign of success.

With the first few episodes, I’ve noticed you’ve focused on the founder story. Are you planning to dig into more topical episodes that bring guests on to discuss news of the day?

Your question is very timely, and the answer to it is that it’s a balancing act! The episode I just published experiments with mixing the founder’s Upstart moment and journey with a topical discussion.

For those interested, I spoke with Ryan Petersen, the CEO of Flexport, about their AI tariff rebate calculator. During the conversation, you’ll hear about Ryan’s Upstart moment, but also how he’s trying to bring America’s money back from tariffs.

For Upstarts, I want episodes to be evergreen enough that busy listeners find value going back a month, or even a few weeks, to say: ‘I want to hear about this founder story, of this cool technology.’ I don’t want them to think: ‘it’s been a week, it’s too late.’ At the same time, I need to be mindful of the world and what’s exciting.

It’s not an accident that the nuclear energy company, Valar Atomics, which we featured recently, had massive news the week before. They flew a small nuclear reactor to Utah with the U.S. government as part of a larger energy initiative, and we talked about where it all began, raising $150M to build gigasites.

Dream guest outside of someone you’ve already spoken to at Forbes/Upstarts Media?

The goal of the podcast is to highlight founder stories and Upstart moments across entrepreneurship, even beyond technology.

I can’t give too much away yet, but I’ve been in discussions with great people in the entertainment industry. Interviewing someone from the sports world would be fun as well. I also know there are amazing entrepreneurial stories in the arts and food spaces.

The show’s true north will always be tech entrepreneurs; the goal is definitely to widen the aperture, though.

Someone specific, if he reads this, is Paul Rabil. He and his brother created the Premiere Lacrosse League. Paul is a former lacrosse star, and I met him a few years ago through Forbes. Their whole goal is to bring lacrosse mainstream. That would be another type of person who one day would be fun for the show.

Are you planning to take the show on the road to any conferences this year?

We’re open to it. I have a preferred studio in New York, but I go where my guests need me. I taped an upcoming episode in London, and I will also be at Human X in San Francisco.

From there, when there are live events or exciting moments that make sense for Upstarts, I’ll gladly consider it.

What makes a good guest for the podcast?

I’m focused on companies that have earned the listeners’ attention, and leaders who have a compelling Upstart narrative. There is an incredible amount of ‘pretty good’ content out there, so my goal is to provide a tactically helpful conversation for builders that fits within a single commute.

I’ve already received a significant number of pitches, but having a large company or a high valuation doesn’t automatically make someone a good fit. I’m asking the audience to trust my curation to find a varied narrative arc from our guests. It is ultimately more of an art than a science.

How do you vet potential speakers to ensure the conversation lands well?

I look for past speaking engagements, whether a panel, a podcast, or a keynote, to get a sense of whether this medium suits them. If the format isn’t a good fit for the guest, it’s not good for the listener or the show.

I also keep an eye on guest oversaturation. Some leaders have stories that are so widely known that it becomes difficult to find a fresh perspective. I want to ensure we aren’t just repeating a narrative that is already everywhere.

Editor’s note: This piece was originally published in March 2026 and is being republished here as part of the launch of Sorry For Cold Calling.

Now the founder and editor of Upstarts Media, Alex is the latest example of someone who charted a new course in the emerging “new media” realm. At Upstarts, Alex covers a topic near and dear to his heart – startups, particularly founders who, as Alex described it to me, “haven’t quite figured it out yet.”

The full transcript of the conversation is below, but if you only have time for a quick scan, check out my “Call Notes” for the points you can’t miss!

Call Notes

• What makes an Upstart: Upstarts Media is focused on startups and founders, particularly companies that “haven’t quite figured it out yet.”

• Building Upstarts in public: Konrad is experimenting with the model in real time, from newsletters to podcasts, video, events, WhatsApp, and founding memberships.

• The benefits of becoming a founding member: Founding members get a direct line to Konrad through WhatsApp, early event access, and a closer look at what he is building. Like other independent media models, Upstarts is not just a publication; it is a community around a specific audience.

• Pitches should help create a news cycle, not chase one: One of the clearest instructions for communicators: bring him hot takes, overlooked trends, unusual stories, or companies that are not simply riding the buzzword of the moment.

What’s one lesson you’ll take from your more than twelve years at Forbes and bring to Upstarts Media?

Forbes taught me the art of storytelling in a way that’s really difficult to learn on your own today. What I mean by that is when you write for a magazine, every word counts: you have to make every word justify its spot in the print layout. It’s so much easier to write long than it is to write short.

[Being deliberate with every word] is something that, as a new publication, I have to be disciplined about. I have to re-earn their attention every paragraph. Forbes taught me that a 400-word story has your attention for a finite amount of time. If you want it to be an 800-word story, you have to be twice as good to justify why they should spend the extra time, and so on.

My goal with Upstarts is that, because I’m only writing a newsletter twice a week with original reporting, I’m not covering every startup story, so I want every startup story I cover to matter. I don’t think I’m doing my job if the reader isn’t plausibly getting to the end.

Will the podcast eventually be an extension of those longer, in-depth features? Could it also be a space for us to talk about breaking news from those same companies, or is your goal for it to be more thought leadership-focused?

The caveat for the audience is that the podcast is still in development. I want to ensure my newsletter is in a good place before I fully embark upon it. My biggest fear is that I throw too many plates in the air and they all crash down.

How I’m thinking about the podcast right now is that it will slot in between daily, more topical talk shows and more evergreen formats. On one end, you have the old morning radio show formats – The Daily is an example of a podcast that’s done an amazing job with this – and then, on the other end of the spectrum, you have these sorts of multi-hour shows, like Acquired, or one-hour-plus interview formats, like Invest Like the Best.

For me, the gap in the market, and where I’d have the most fun, is in between: weekly interviews around a topic or a theme I think we should be discussing more. So it’s not ‘tell me your life story,’ but ‘let’s talk about one thing that, unless you’re chronically online like me, you didn’t necessarily fully pick up on this week.’ Or it could inform you when you talk to someone you know over the weekend.

I’m sure you’re thinking about evergreen content, especially so you can take time off and have content banked.

I think one challenge for me, where the Upstarts community can give me feedback and help me out, is getting the balance right between content that has an evergreen nature, in the sense that you could look it up later and it’s still helpful – because we’re all so busy – and content that can be so evergreen that it’s never valuable in the first place. I don’t want it to become sanitized in a way that cuts out the juice. I have to figure out the balance there.

What gave you the confidence that now was the right time to go out on your own? To me, these tailwinds have been brewing for a while, especially now with the recent acquisition of TechCrunch.

I had a somewhat unique situation where I was at Forbes for 12 years. That’s a long time in media. And I loved my team. My boss, whom I didn’t want to leave, was John Paczkowski. He’s incredible and someone I respect. I also really respect the team I had at Forbes, from editors like Katharine Schwab to reporter friends such as David Jeans and Emily Baker-White. If anything, I feel like I stayed longer than anticipated because of that team of killers.

Giving that up was hard, but I also felt I had achieved all my objectives at Forbes. I needed to take a risk to flex new muscles and push myself to the next level of my career.

It’s hard to exceed the expectations that I have now, building a new business. I’m trying to do things I never had to do before, from business development to community building, to figuring out a content strategy, all while still being a good reporter. It’s a big swing chance to go to another level in my career.

I also believe this is a moment in media where going independent has a tailwind. It’s a pivotal moment for in-depth, original reporting around the startup ecosystem. I’m happy to go more in-depth there if it’s helpful.

I’d love you to, and I’d even follow up by saying you’re entering a market that companies are just now trying to figure out. And being a first mover at something like this is one of the most valuable things you can do. You have the opportunity to carve out a niche for yourself.

This is a moment when so much media attention, for very understandable reasons, is focused on big tech politics and policy questions. I wrote a cover story on AI policy, and I believe that’s important, but I’ve always enjoyed and found that I could contribute a lot covering startups and the founder journey. I do a good job of explaining how things work, figuring out what motivates a founder. And so when I thought about what articles I enjoy writing, and what stories I think my audience resonates with, it really was that startup journey up to and around the IPO. When things were not fully figured out.

Who, if anyone, are you leaning on for advice about Upstarts Media? What Substacks do you read and subscribe to/want to emulate?

The best advice I got was to not overthink and build in public and ship experiments. Those people said your audience will be rooting for you, and they’ll be well aware you are out there on your own, trying this stuff.

On Substack, I look up to Alex Kantrowitz of Big Technology and Alex Wilhelm, who used to work at TechCrunch and has a Substack, Cautious Optimism. Eric Newcomer is another friend who has been so impressive and helpful with Newcomer.

Another old work pal is Polina Pompliano, who writes The Profile. I also read journalism-adjacent newsletters, like The Pragmatic Engineer by Gergely Orosz, who’s done amazing work. I’ve read a lot of Packy McCormick’s writing from Not Boring and Lenny Rachitsky’s Lenny’s Newsletter. All the leading tech community writers have done an incredible job building an audience and close relationships with them. I can learn so much from them.

I want to get nostalgic with you for a minute. What was the one feature you wrote about an under-hyped challenger that made you know you wanted to focus on this group for the rest of your career?

It was great to do a story on Microsoft’s turnaround with Satya Nadella and go deep with a public company. I’ve also done interesting ones around AI. One was more of a trend story on Marc Andreessen versus Vinod Khosla and Reid Hoffman. That was its own challenge.

If it’s just one profile, it has to be Canva and Melanie Perkins. I profiled Canva in 2019. It was the first big feature about them; the company was valued at $3 billion and not as well known because it was based in Australia. And Melanie is such an interesting tech leader. She and her husband, a co-founder of Canva, got engaged with a $30 engagement ring they found at a bazaar in Turkey. They’re Australian backpackers at heart, and they’re both worth billions of dollars, but it all goes to the Canva Foundation to have an impact on the world. I’ve had people tell me they got into tech because of her story. So, from an impact standpoint, that meant a lot to me.

I’ve gotta ask, how did I get you to go to Pittsburgh to attend a board game competition?

That was a good story! Let’s talk about it. I was thinking back about my favorite profiles in terms of quirky experiences I did, and it was a top-three quirky bucket list experience. I mean, board games in the middle of the Pennsylvania Poconos.

You almost missed the flight.

I almost missed the fight. I rented a car to drive to a hotel, and it’s this mountain lodge place. I still have [Appian founder Matt Calkins’] board games.

Understanding founders’ passions and other things they do, even if it feels unrelated to their day job, tells you a lot about who they are, how they build, and what’s driving them in a way that can make their companies more relatable. It all makes more sense.

Camping with local founders in the Utah foothills was a way to get to know Silicon Slopes. Singing karaoke with Marc Benioff in Japan alongside the CEO of Rakuten was a unique way to understand the world of leaders that Benioff rubs shoulders with. Observing Calkins winning at board games was an experience, too.

Anything you can share with me and readers of this blog that you’re excited to unveil?

I’m interested in how I can create more multimedia stories. Coming soon to Upstarts, for those interested, will be a joint emergency pod-style episode with a founder whose startup I’m covering. We’ll both be guests on another person’s show to discuss the story. I did a live video with the CEO of Runway a couple of weeks ago. I want to do more impromptu video chats. There are so many ways to connect with startups and leaders in the industry, where the timing isn’t right to do a full-fledged feature.

How far out are you planning for longer, in-depth features? What can we PR people pitch to you to have our clients be considered (company milestones, funding, C-level hire, surveys/data, etc.)? How might it differ from what we offered you at Forbes?

Over time, I plan to standardize covering one exclusive funding round and one possible deep dive on a fund or new fund announcement from a VC, every month. I’d like there to be systemization to that, where people can pitch me, and it’s meritocratic: I’m looking for what, I feel, is the most interesting for the Upstarts audience. For now, send me stories that are interesting to share with the Upstarts community versus a more traditional publication – quirky or fun ones.

I want Upstarts to be inclusive for the entire startup community, where people who never pay still get value, so we’ll have sponsors and other ways to make that work. But then, I also need to ensure that anyone who pays to subscribe gets great value and feels good about supporting me. And so to the extent that clients or companies can share a hot take with me, or say, ‘we could be part of an interesting trend that people aren’t aware of,’ I’m interested. I know that by doing that, you’re trying to go against the news cycle to create your own. For anyone who feels like they’re not using the buzzword of the moment, that could be a good reason to connect with Upstarts.

I know your time is precious, especially now as you’re ramping up, but will you travel to user conferences at all? If so, what factors will you use to assess each event?

I heard a founder say recently at an event I attended, “I’m always paranoid that I can be doing more. I feel guilty even being on the stage right now, because it’s an afternoon I’m not working on my business.” That resonated with me in a new way.

I want to be out there sharing the word about Upstarts, engaging with our community, and meeting audience members, but I also need to report. I’ll be speaking at Startup Grind at the end of April. I’m considering doing some sort of subscriber meetup while I’m in the Bay Area. If I spend two days in San Francisco, I need to get as much out of that as I can. Similarly, I’m thinking about other cities I can go to where I could cluster a big event with a small Upstarts-focused one and reporting opportunities.

Beyond access to you via WhatsApp, what can founding members expect from their commitment?

We’ve only been live for two weeks, so I appreciate people’s patience as we ramp everything up. The benefit of the Founding Upstarts’ WhatsApp group is that it offers a direct line to me. I can share tidbits of news that don’t rise to the newsletter, you can get early word on events, and my feedback on your responses. It’s a real commitment for me. These individuals are serious about this news and pay attention to my work, so I’m very hopeful it’s a high-quality discussion.

A number of the first Founding Upstarts are coming to my launch party towards the end of the month. I plan to find as many ways as I can, within reason, to bring those Founding Upstarts close to what I’m doing, to ensure they feel like they’re part of the community and proud that they are.

I really appreciate you taking the time to talk with me. Any closing thoughts we didn’t cover?

If anyone has an idea for something I didn’t mention, or where I could be engaging with people, I’m building in public at Upstarts Media. I welcome feedback.

For anyone asking how they can support me, the most obvious way is that if you haven’t subscribed, go to Upstartsmedia.com and sign up. And if you haven’t paid or are considering paying, that will be the best way to allow us to build all this faster.

Editor’s note: This piece was originally published in April 2025 and is being republished here as part of the launch of Sorry For Cold Calling. Some references reflect the time it was originally written.

The full transcript of the conversation is below, but if you only have time for a quick scan, check out my “Call Notes” for the points you can’t miss!

Call Notes

• The known versus the unknown: When it comes to making the most of her limited time at the show, Sam prioritizes on-the-record interviews with companies she knows, rather than intro meetings. She wants to know for certain that when the conversation wraps, Sam will have a quote for something she’s working on.

• Black Hat vs. DEF CON: Sam’s approaches to Black Hat and DEF CON are very different. DEF CON is all about panels, and that’s consistent every year. Black Hat, for her, is about catching the handful of high-profile keynotes. She bases her selection on her knowledge of the speakers, whether she knows if they’ll provide value to her understanding of a topic, or someone who often gives a buzzworthy quote about China or AI.

• Why events are so valuable: To maximize her time on-site, Sam prefers to attend a press conference or a media mixer where she can connect with multiple experts from a company at once. If she knows that your company is hosting a party, she would rather attend that than try to arrange one-on-ones with each of them to save time. Don’t be surprised when she doesn’t reach out to schedule for that reason.

• Make your pitches standout: When it comes to getting a journalist to read your pitch email, Sam’s advice is to make it personal and make it quick: “Here’s why I think you would be great. You want it?”

Something I want to demystify for readers is the time you have available to take meetings at conferences. It would be great if you could take us through a day in the life of an Axios reporter at Black Hat.

Because I’m the only person who covers my beat, I live and breathe by this one Google Doc. For a show like Black Hat, I compile everything, usually a week or two before, depending on the news that year. This year, it was days before. I don’t recommend that.

When I arrive at the show, I’m usually on the ground prioritizing meetings from the jump. I start meetings around 10 a.m. From there, it’s bouncing around from room to room, trying to get as many one-on-ones done based on all of the bigger picture stories I’m working on.

I make the most of the fact that everyone is in one spot, and we don’t have to coordinate phone calls or make calendars line up. We don’t have to play that game because we’re all in one spot. It’s amazing to find a place in the lounge or the media room and chat for 20 minutes.

I prioritize on-the-record interviews with companies that I know, rather than introductory meetings, because I need things for my newsletter and to file stories.

At some point during the day, I do eat. It’s unclear when I’ll have time. But I eat at some point. Or I lean into coffee.

After that, I try to pop into a panel or two. But some years, if I can’t make it to a panel, it’s not a big deal. I’m here mostly to take meetings on the side.

In the evenings, I usually make it to two or three parties, and if there’s a vendor I couldn’t do that catch-up meeting with, I’ll say hi and hang out with them off-the-record. That always makes things so much easier. I want to show that I’m a human being who’s friendly and kind and not out for someone. That way, if, god forbid, I ended up on a call where it gets a little tense, at least we know my intentions and we have that relationship. Then, at some point, I cap it. The week here is so long that I usually attend one or two, and I’m in bed by nine.

Rarely do I file from the conference, especially if it’s unrelated to the newsletter. I would only publish something “big picture” on cybersecurity.

It’s a lot of running around, wearing sneakers, and meeting with whoever I can.

You mentioned you were late to dig into the agenda this year. What sessions stuck out? And how many do you plan on attending?

It’s funny, because [what sticks out] also keeps changing. It’s usually a few of the government ones. But now, this year, I have a big hole in my calendar. This year, in particular, it varies between Black Hat and DEF CON. I would say my approach to DEF CON is the opposite of Black Hat, in that [DEF CON is] very panel-focused every year. If we’re talking Black Hat, I attend high-profile keynotes. I prioritize the ones where I know the speaker will provide value to my understanding of a topic, or give a buzzworthy quote about China or artificial intelligence. I know they’ll cut through the BS of what people need to know about the threat landscape and how it’s changing, or similarly, how defenders need to be on top of that evolution.

This year, I’m trying to go to [Former U.S. National Cyber Director] Chris Inglis and [Founding Partner of Silver Buckshot Ventures] Nicole Perloth’s keynotes. And then anything panel-wise on AI. I’m personally super obsessed. I’m super obsessed with the cat and mouse of whether or not defenders are ready for what’s coming. Attackers can play with AI all day long. They don’t have to get their CFO to sign off on buying OpenAI subscriptions. Attackers also don’t have to explain to their CTO about the organization’s heightened cloud usage.

I’m obsessed with how quickly we’re adapting. Do we have the tools? I’m always trying to get a read on that temperature track, and what is actually legitimate and objective in AI for cybersecurity. At some point, I’ll go through the expo room and count how many of the booths have agentic AI signage displayed on them. I’ll likely run out of time doing that.

Back to your original question, likely one or two sessions a day.

I published an interview with CSO’s Cynthia Brumfield about the agenda being light on government officials this year. A show like Black Hat likely makes it easier to get in front of them. Does that take away from the experience for you?

Yes and no. For me, I’m the rare cybersecurity reporter that’s not in Washington, D.C., so the lack of government speakers is not as detrimental to me as it is for others, in part because I’m thinking about the industry at large.

I would take a broader view. This administration seems like it will take a light touch on regulation, compared to any other administration. Cybersecurity partnerships aren’t as heavily relied on. Maybe they will be, but that’s up in the air. Because of all that, I think a lot of the change in the industry, and in cybersecurity as a community, will be driven by industry over the next few years. D.C. is not going to operate the same way. CISA is much smaller than it was six months ago. The DOD is not as engaged in these events. Everyone I knew at the NSA is now gone, which is rare, no matter the administration.

I’m personally thinking about AI and social engineering, [managed service providers] and insurers. The industry still comes here. I try to meet with as many CEOs as well. That, and the lack of government presence, is a story in and of itself. So it doesn’t change the experience much for me, but it does mean I value one-on-one time more.

You publish the Future of Cybersecurity Newsletter once a week on Tuesdays. You hinted in your last edition that you’d have a bonus issue for Black Hat. When do you carve out time to write? Because this blog won’t publish until well after your newsletter, can you tease what you may cover?

How do I carve out time to write is an amazing question. It’s been a lot of trial and error. Some years, I definitely overbooked. That meant I was writing quickly, and I got the smart brevity in the 10 minutes I had between sessions or meetings in the media room. Or it meant I was eating my dinner in my bed with my computer in the hotel room at nine o’clock at night, trying to file for the next day. In past years, it was harder because I had the Friday newsletter. That meant I had to file multiple times in the week, but I figured it out.

This year, I pushed myself to carve out time. I also had to carve out time to take breaks. I will RSVP to attend parties, but if I realize halfway through the day that I don’t have the energy and I have to write, I won’t go. I’ve allowed myself to be super flexible with my schedule without having to be at or do everything. I’m one person, and I have my limits.

Story-wise, a lot of the things I’m eyeing here are evergreen, big-picture thoughts that I was already thinking about before I left for Vegas. These were things I believed would be big at the show. I did a roundup of all the announcements I’ve gotten. I have an inbox full of product pitches that I just don’t have the time to reply to. Many of them are, “XYZ vendor has a new autonomous agent that can do XYZ.” I plan to ask executives where this is all heading. Will adoption be fast or slow, and what does that look like on the defense side?

Generally, I get a lot from walking into a briefing and telling the interviewee I have three topics, and see what happens. Then, someone says an off-hand thing, and that plants a seed.

Then, I would like to do a prediction series once a month. I’d spotlight high-profile executives who have been in the industry for years about what they’re thinking and what might happen next year. Someone once told me that, in the next year, we’ll have our first trillion-dollar cybersecurity company that isn’t Microsoft.

I’ve partnered with you on panel moderation at events. Have you been approached to moderate any panels at Black Hat this year? How do you pick and choose which ones you want to be a part of or not?

I do, but I didn’t get any for Black Hat. I’ve been doing a lot this year, so I wasn’t upset. I was thinking, “I don’t have to pack my nice shoes.”

In terms of how I choose, it’s usually a dual decision. [First,] we have editorial guidelines within Axios, so it depends on who’s asking. It depends on the audience, the purpose of the panel. They can feel a little like I’m helping a company do a sales pitch, which I know can be a tough line, but if the ask is, “Sam, we need you to go on stage and ask our CEO questions about our new product,” then I’m not the right fit. In general, I rarely ever turn things down.

[Second,] I want it to be a good group of people or an interesting topic that will help others learn. I view them as networking opportunities. I get to know the panelists in a way that we wouldn’t otherwise. Then they think of me more than another byline that they saw somewhere, like another person. If it’s interesting and there’s a conversational feel, I’m down.

You mentioned to us that you like attending events that companies host in the evening. As this interview has shown, your schedule is tight. Is it easier for you to attend events or take one-on-ones?

This is a hard ranking. I definitely put a panel last. Someone who’s a daily publication reporter might rank that differently, but for me, smart brevity, I’m not writing on every panel.

It’s a slight edge for one-on-ones over events, but they’re interchangeable depending on the event. If there’s a press conference or a media mixer where I know multiple experts I would have spoken with from a company will be in attendance, I’ll prioritize that over a one-on-one with each of them. It’s so easy for me to pop in for an hour and talk to everyone. The companies I know that do the mixers, I won’t reach out to schedule time with them. I prioritize interviews where I know I’ll get an end product.

As someone we’re sure has countless emails in their inbox to meet companies at Black Hat, what advice would you give to a comms person to stand out? Is it persistence? Do you want to see an understanding of the trends you’re covering?

It’s hard because it depends on the comms person. I don’t want to sound like I’m unaware, especially at an agency, of how different clients have different things. The more tailored or personal it is, the better. I receive so many product announcement emails, and people are persistent because they know I cover agentic.

Be targeted and consistent with them. The more you understand what they do at a publication, the better. Punch up the pitches. Some are four or five-paragraph essays. The more you can just say, “Hey, I have this under embargo,” or, “Here’s why I think you would be great. You want it?” Also, “Meet with this CEO based on your past coverage of X, Y, and Z.”

I’m not sure about persistence, because I have so many people ringing my phone off the hook all the time, and I usually don’t have time. I don’t like having a bunch of emails in my inbox, and there’s no way you do either.

Editor’s note: This piece was originally published in August 2025 and is being republished here as part of the launch of Sorry For Cold Calling. Some references reflect the time it was originally written.

Together, we explored everything from how she approaches Black Hat convention coverage to why staying for DEF CON is so important, along with the agenda gaps she’s noticed that were historically filled by public policymakers. Beyond the trade shows, we also discussed product news and her secret sauce for identifying trends that matter to her readers.

The full transcript of the conversation is below, but if you only have time for a quick scan, check out my “Call Notes” for the points you can’t miss!

Call Notes

• Metacurity is guided by signal density: Brumfield uses a custom RSS and keyword system to identify which cybersecurity stories are gaining real traction across the media. When multiple publications cover the same topic, the system clusters those stories together and pushes them up in priority. That means her editorial judgment is informed by where coverage is already concentrating, not just by individual pitches.

• Product news needs a larger editorial hook: Brumfield made clear that CSO and the other publications she freelances for are not venues for standalone product announcements. Metacurity can occasionally include products, but only when they connect to a bigger news story or broader security angle.

• Travel risk is now part of the conference calculus: Black Hat and DEF CON may be seeing fewer policymakers, reporters, and international attendees, not because the events are less relevant, but because U.S. border uncertainty has made attendance feel riskier.

I’m curious to learn about how you tackle coverage for larger industry conferences.

Every year I’ve covered what I call the “Hacker Summer Camp” events has been different. I’ve covered two [Black Hat conferences] in person, on the ground, live. That’s been much different from attending them remotely. Of course, you really can’t attend DEF CON remotely, so remote coverage is contingent on research that’s released in conjunction with both Black Hat and DEF CON. That research gives me a sense of the information being conveyed at DEF CON.

Because I’m a freelancer, my time allocation and pitches are contingent on what the publications want. The year before last, I wrote several big pieces on the ground from both DEF CON and Black Hat around two specific angles, because the publication I was writing for really wanted to get at those particular questions. In other circumstances, I go through the agenda for both events and identify writing opportunities that way. It’s all contingent on editorial interest and what people are willing to pay for.

We’ve heard many reporters say they prefer to be in Las Vegas the second half of the week so they can also attend DEF CON. Is that your preference as well?

There’s a lot of overlap. Many organizations and researchers will give a talk at Black Hat and share the same presentation or talk at DEF CON, but the approach is different. Black Hat tends to be more corporate than DEF CON. I mean, we’re forgetting BSides Las Vegas, which always sounds very cool and usually precedes the other two big events, but has a lot of the same kinds of speakers and content. I haven’t been fortunate enough to get to Vegas early enough to attend BSides Las Vegas, but when I have attended [the major shows] in person, I’m there the entire week.

It’s a Las Vegas overdose. That’s what happened the year before last, when I went in person. Part of it is because I do want to be there for everything, but it depends on the budget and how much intestinal fortitude people have to spend that much time in Vegas, where they think the more interesting topics will be. DEF CON is more interesting in some respects than Black Hat because it’s much less corporate and marketing-focused. But so much of DEF CON is off the record, as is the video and image-based content, where it’s not at Black Hat.

They’re both good. I’m feeling a little bit of FOMO by not going this year. On the other hand, I’ve been to Vegas three times in the past year, so I’m not terribly sad to not be going.

How do you feel about product news generally?

Well, I’ll be honest and say that 99% of the pieces that I’m pitched are products. They’re kind of banal in their approach. Nothing is exciting about them, nothing interesting.

I do tend to look more at embargoed pitches because they may include something interesting that nobody else has covered. Seldom do I take a pitch that’s been pitched to me and then pitch to my editors, but I will use that pitch at some point if it’s relevant to a topic I’m interested in that has a good angle for the readership of the various publications.

I hate to burst your bubble, but rarely do I pick up a pitch and say, “I’m going with that one.”

What is it like to work as a freelancer for CSO? Do you have the freedom to cover what you want, or does a dialogue need to happen with your editor in the weeks leading up to publication?

None of the publications I freelance for want product pitches. That’s not their media. That’s not what they do. I have another publication of my own called Metacurity, where sometimes products make it in because they’re hooked to a bigger news story or a bigger angle.

I’ve had people say to me, “Why don’t you include this product announcement of my company in Metacurity?” I tell them that’s not what I do.

It’s just not engaging to you.

Some products are just so dynamite that you can’t not include them, and they’re engaging in different ways, but for the most part, no.

What product in the last six to 12 months have you heard about and said, “That’s dynamite?”

Google has an AI agent it calls Big Sleep. The PR team shared that Big Sleep detected a second critical vulnerability that was on the radar of threat actors, but hadn’t been exploited yet.

How do you decide what to include in your newsletter?

About six years ago, I sat down and built this system that would go through RSS feeds and pick out stories based on keywords. Then, if multiple publications covered that particular keyword, it would cluster all the publications together.

That’s what, to a large degree, guides my prioritization, both for Metacurity and what I pitch to other publications. Today [July 21], for example, my system flagged SharePoint’s zero-day. So, when I ran the system, it clustered 16 to 17 different articles at the top of the results that I ran through this complex algorithmic system. I use that as a guide very frequently for what is and isn’t relevant.

I also keep an eye on social media to see what people are talking about on Bluesky. A major scoop by top publications will catch my attention, even if my algorithm disagrees.

What do you anticipate the top three or four trends that will show up in your inbox?

It’s hard to know. AI has been so dominant the last couple of years, and is even more so now. We even have subverticals of AI now, “vibe hacking” and “vibe coding.” There’s also the evolving law and policy surrounding emerging AI products. That’s going to be dominant, too.

When it comes to Hacker Summer Camp, It’s hard for me to tell you because a lot of my previous DEF CONs and Black Hats pieces have been driven by public policymakers who show up and give keynotes. The last time I checked the agenda, there were a few from the public policy arena, but it was even very light this year at the RSAC Conference. There aren’t the kind of keynote speeches that you’ve expected from a week at Black Hat. I assume threat intelligence will be divulged during the event, which will probably be focused on China. China still seems to be dominant as it has been over the last couple of years.

You mentioned not seeing a significant number of keynotes from public policymakers this year. We get readouts of reporters being added to the attendee list. It seems smaller than in past years. I wonder if there’s a correlation there.

This year, we have the added dark cloud of the Trump administration pulling people out of line at airports and detaining them before returning them to their home countries. The grounds for this are difficult to determine. I know, and you probably know, who some of these people are who say they’re not coming to Black Hat and DEF CON because they don’t want to risk it. That’s been disincentive. I suspect that’s true for many events.

You’ve covered the Trump administration’s cybersecurity policy closely since his inauguration. Do you find sources to be forthcoming with their opinions, or are they guarded?

It was even difficult under the Biden administration. CISA was very helpful in communication around the CVE (Common Vulnerabilities and Exposures) Program because they are the primary funder. The House Committee on Homeland Security is really good.

How have cybersecurity vendors helped to close the gap?

Vendors and CISOs in particular have been very communicative with me on all kinds of issues. But there’s a real hesitancy at the moment to step into the political arena, because no one wants to be publicly supportive or critical of anything that may be transpiring. No one wants to say anything in either direction.

We’ve discussed industry shows, but do you attend vendor conferences?

As a freelancer, I don’t have the budget to attend vendor conferences using the publication’s budgets. There are sponsored vendor conferences, which I’ve attended on my own. They have to be really interesting. I want to make connections and learn more about topics that are relevant to me. I’m very choosy.

Editor’s note: This piece was originally published in July 2025 and is being republished here as part of the launch of Sorry For Cold Calling. Some references reflect the time it was originally written.

The full transcript of the conversation is below, but if you only have time for a quick scan, check out my “Call Notes” for the points you can’t miss!

Call Notes

• Understand their audience: Big Technology started as an extension of Kantrowitz’s book. That matters for PR people because the pitch should map back to the creator’s stated interests: tech giants, AI strategy, and where the industry is headed.

• Independent media is not a side channel: Brands still debating whether “new media” matters are already late.

• Audience quality beats audience size: Big Technology’s value is not just reach. It is audience quality. The paid Discord, subscriber Q&As, and newsletter all point to a highly engaged community with a strong signal-to-noise ratio.

• Access matters, but the bar is high: Kantrowitz is selective about conferences and travel because he is a one-person publication. He will attend if there is a clear editorial payoff, such as a strong executive interview. For communicators, “come meet our executives” is not enough. The pitch needs a tangible story.

I’m sure a blog post exists about it online, but I want to start at the beginning with you and those reading this. Why start Big Technology?

I released my book, Always Day One in April 2020. After that, amid all the craziness of the COVID news cycle, I wanted to spend my time focused on the topics I covered in that book. Looking at things like how the tech giants operate, their strategies, and most importantly, how they use AI in their processes. I felt I’d be much more effective if I tackled these questions as an independent reporter working on my own than as a reporter within a newsroom. So in May 2020, I gave my notice at BuzzFeed and published the first story a few weeks later. It’s almost been five years to the day. It doesn’t feel like five years. But it’s been such a cool, cool journey.

When did you know it was the right time for you in your career to leave BuzzFeed and start your own thing? I’m sure it wasn’t an easy decision.

It would’ve been harder to say no. If I didn’t leave I would’ve been laid off. I spent two years putting my heart into this book and my options were to sort of allow it to disappear in a very busy news cycle, or put everything I had into talking more about it, continuing to write on the same themes, and sinking or swimming based off of the success or failure of that next project. The only option I felt I had was to go out and do everything I could to continue to keep it in people’s minds. And so, the Big Technology experiment really started as a way to keep the book alive, an extension of the book, and then it became a real media company.

What early challenges were you forced to navigate? Was building a subscriber base the toughest? Do you have any idea how many of your Buzzfeed readers followed you?

For the podcast, a lot of my early energy was put into figuring out how to set up a podcast and finding the right partners. I was really excited about the opportunity, and I wanted to make sure that, when it launched, I did it right. On the audience, it’s a great question. It turned out that wasn’t a major issue. I had a pretty good, built-in audience right away. That’s for two reasons: 1) I was lucky that BuzzFeed let me take my email newsletter list with me when I left. I really can’t say enough good things about BuzzFeed. And so I started with a list of 5K engaged subscribers right away. I was still doing the book tour when I launched Big Technology, and the best way to build a podcast is to go on other podcasts and tell listeners you have a show as well. The tail end of the book tour helped seed the audience for the podcast, and so I felt comfortable bringing guests on in the early days and knowing that there would be people listening to it, as opposed to just us talking to a ghost town.

What factors i​nfluenced your decision to launch a paid subscriber option?

I launched paid subscriptions on Big Technology in October 2023, more than three years after the publication got off the ground. I did it largely out of encouragement from friends, readers, and Substack itself. I think there’s a desire out there among people to support publications, especially if you’re valuable and they want to read more. Until that point, I’d mostly relied on advertising, and I wanted to make that option available to readers only at the right time. It took me a long time to figure out exactly what I wanted to offer at a price I felt was fair. Eventually, I thought it was time to launch a premium tier that would give readers more access to each other. Part of the paid subscription tier now is the ability to participate in a private Discord. The signal-to-noise ratio there is incredibly good. It also enabled me to bring some guest writers on and pay them a fair wage for their work.

What other mediums do you have on your radar to explore?

I’m very active on LinkedIn, and the community there is fantastic. I published stuff from my page and the Big Technology page, and I’m investing heavily in video there. A couple of years ago, I wrote this story about how it’s the one good social network. That was before I worked with them on the podcast network, and I stand by that today.

What advice do you have for brands who are interested in pursuing opportunities with “new media” but are unsure of the value or where to get started?

I would say ignore [new media] at your own risk. If someone is asking those questions, you’re already behind. We also know what happened in the “Podcast Election.” Smart executives and smart companies know the value of working with individual creators. There’s a reason why Google DeepMind’s CEO Demis Hassabis, Salesforce’s CEO Marc Benioff, and AWS’ CEO Matt Garman all came through Big Technology over the past few months. You’re not too late, but you are late.

I heard from colleagues that you attended re:Invent last year. How often are you able to travel to conferences and meet with new sources in an introductory format?

I am a one-person publication, so I have to be very selective when I go to things. It’s not only a financial investment, but a time investment, so I need to make sure it’s worth spending the time if I go. I think the long and short of it is I’ll go to something if I can be pretty sure I’ll be able to bring a great interview to the podcast audience and write something based on that. AWS reinvent was a no-brainer for me. I was lucky enough to be able to interview Matt Garman and publish the transcript, then publish a reaction piece at the end of the week as well.

Quickly on AI, what themes interest you most? Or, what do you see yourself exploring more beyond AI in 2025?

I’m obsessed with two things. 1) Where the industry is going. We talk about that every Friday on the podcast. 2) The weirder things. I, for whatever reason, care a lot about people falling in love with AI bots and believing they’re real, or AI with potentially emergent behaviors. I’m working on a story about AI working to deceive its evaluators [published on February 21]. This stuff is crazy, this technology is mind-blowing in so many different ways. Five years from now, that’s anyone’s guess. There’s going to be a lot that’s going to happen between now and then. The AI labs have to pay off these record-breaking investments they’re taking in the battle between open-source and proprietary models. I think, most importantly, there’s the big question of whether there will be applications beyond ChatGPT that’ll take off with consumers.

You recently did a subscriber Q&A with Box CEO Aaron Levie. What can you tell me about that and are there plans to do another executive Q&A soon? Was that a paid activation or someone your subscribers wanted to hear from?

In-person will be a bigger part of my strategy moving forward. Aaron Levie had been on the show several times already. Every time he was on, it seemed like something crazy was happening in the AI world. He was a natural first guest for the public in-person event. We brought everybody together like an old-school New York Tech meetup style – pizza and beer night at a company in the tech scene. Getting a chance to chat with Aaron about the latest in AI and open up the floor for Q&A was very cool.

Have you thought about adding to your team (other reporters or producers) at Big Technology? How might that work?

We’ve been really lucky to have Kristi Coulter, an ex-Amazon employee who was there for more than a decade, and she writes about not only her experiences at Amazon but the current slate of Amazon news through her perspective as a former insider. She was able to, for instance, break down the changes in the leadership organization chart and give a sense of where the company was going. This week, Mike Shields, former AdWeek editor, former Wall Street Journal reporter, and a current fellow Substacker at Next In Media, is doing a story that I’ve always wanted to reel in, but just didn’t have the time or the chops necessarily to do it. It’s a look at how Meta circumvented Apple’s anti-tracking restrictions and built an even stronger ad business than it had before Apple cracked down on it. These types of stories are wins for everybody. It’s more reporting and better reporting.

How about full-timers under the Big Technology umbrella?

It’s always possible. I’m comfortable running a one-person publication now, but if I’m in a position to hire somebody, that’d be amazing. I just brought on a second intern or fellow. The first person I had in that role helped me with reporting and co-bylined pieces with me. We syndicated one of those in the Boston Globe. They’re currently a full-time reporter, so that system has worked well for me. I could see it expanding over time, potentially.

I really appreciate you taking the time to talk with me. What are some things you’re working on now that people should be aware of?

Come on board with Big Technology. Subscribe to the newsletter, sign up to be a paid subscriber, and join our Discord. At the very least, check out our twice-weekly podcast episodes. I’m having fun, and our audience is having fun. You can also enjoy yourself and learn something as you do it.

Editor’s note: This piece was originally published in March 2025 and is being republished here as part of the launch of Sorry I Cold Called You. Some references reflect the time it was originally written.

The full transcript of the conversation is below, but if you only have time for a quick scan, check out my “Call Notes” for the points you can’t miss!

Call Notes

• The Maker Over the Marketer: The Deep View prioritizes makers, builders, founders, product managers, and developers—the people behind the solutions—rather than just the executives calling the shots.

• Cutting Through the Noise: Coverage isn’t about chasing every 24-hour news cycle. Jason encourages the team to chase stories where they can provide deeper context, adding original perspectives, exclusive scoops, and analysis that cuts through the noise.

• Deep View on the Move: To stay close to the individuals at the forefront of AI, the team maintains an active in-person presence at major shows, including NVIDIA GTC, HumanX, and Google I/O. User conference travel is accepted on a case-by-case basis, provided there is a high-value editorial hook.

• Conversational Chemistry: The bar for the The Deep View: Conversations podcast is a “coffee-shop chat” vibe. If an executive is too polished or over-media-trained, they are likely a mismatch.

Why was now the right time to join The Deep View? Were there hesitations or fears about leaving ZDNET when you did?

I wasn’t looking for an opportunity; it came looking for me. At ZDNET, I had the dream. I built the team and relaunched the site, brand, and mission for the next decade. I had four years there, where I finally got to do tech media the way I always wanted to. It was tough to leave that.

When we relaunched in August 2022, I told the team — and, this looks naive today — that in three years, AI would be our biggest topic. At that point, it was our 22nd most popular topic on ZDNET. Then ChatGPT launched three months later. By the beginning of 2023, it was already our number one topic. We had a great run, in which we became one of the leading outlets covering AI with a dedicated team and section.

By 2025, I realized there was so much happening so fast in AI, but I could only devote so much time to it because we covered everything from consumer electronics to enterprise tech. I felt this pull to spend all my time learning and writing about AI.

When a recruiter I trust reached out, I talked to the founder, Faris Kojok, and was incredibly impressed. He wasn’t trying to make a quick buck; he wanted to build a generational media brand.

Faris’ vision aligned with the thesis I had at ZDNET since 2022: The future of media is deeper engagements with specific audiences. It was an opportunity for me to do two things: cover AI full-time, and build a next-generation media company.

My thesis has been that the era of playing to algorithms, SEO, socials, and otherwise, is ending. The future is earned trust, where people (purposefully) subscribe to you. Again, The Deep View was the opportunity to cover AI full-time and build a next-gen media company around that thesis.

Did you consult anyone during the process? Did it take much convincing to get you to join?

I talked to several mentors in the industry. Mark Larkin, who was our President at CNET and is now the CEO of Clearlink; Wayne Silverman, a former Chief Revenue Officer of Spiceworks Ziff Davis, and The Channel Company; and Matt McMahon, who held SVP and EVP roles at CBS and Paramount. Matt had started multiple startups and had multiple exits, so he knew the startup game really well. That was a great help because moving to a scrappy startup is a very specific experience.

I didn’t speak with anyone who had run a newsletter specifically, because I’d run those for a long time at TechRepublic, CNET, and ZDNET. I felt confident there. It was more about thinking strategically about my career and the day-to-day of building a team.

I couldn’t help but notice Sabrina Ortiz also joined The Deep View shortly after you. Do you have plans to bring more team members into the fold? I also saw Steven Vaughan-Nichols contribute recently as well.

I take it as a huge compliment when people want to work with me again. It means they had a good experience and that you were a good mentor. I have one person, Allison DeNisco Rayome, who has worked with me on three teams: TechRepublic, CNET, and ZDNET. She’s still at ZDNET and doing amazing work.

Poaching is a sensitive topic, so I let people seek me out. I don’t like to burn bridges. Many freelancers I’ve worked with are interested in coming to The Deep View, but my budget is more modest to start. I’m also thoughtful about letting the dust settle, and I certainly want ZDNET to continue to be very successful. I left a lot of my blood on the floor over there, helping to build that brand for the next decade.

For a comms professional potentially unfamiliar with The Deep View, what can they expect to find? How can we be the best partners to you and your team?

We have a strong perspective on helping the audience make sense of AI. There’s so much confusion. Narratives about bubbles bursting vs. AI being the best investment, or AI killing jobs vs. creating them. As journalists, that uncertainty is where there’s amazing work for us today to help the audience.

We are not doomers, and we aren’t cheerleaders. We have a mature, nuanced, analytical view. We help people cut through the fluff and understand what this means for their coworkers, family, and community. We only write stories where we have something to add, whether it’s original reporting, scoops, exclusives, or deeper analysis. We’re building around quality and trust. We don’t try to curate all the news, because AI will eventually do that better than us. We pick the three most important stories of the day and give you a double-click beyond the headlines.

We want the story behind the story. We love the human element. Can we get the product manager, the executive, or the developer who started the thing? We want to talk about the why, the roots of the project, and the dream state for the product.

As things become more automated, human storytelling builds trust. We want to talk to the makers and builders because they have a perspective that is very clear and considered, rather than just a marketing pitch.

I saw Sabrina at Mobile World Congress this week. What other events will your team have a presence at this year?

We’ll be at HumanX, Google I/O, Ai4, and many other events where AI is a critical topic. We’re dedicated to covering the most important AI events in person because that’s how you get closest to the people. We do selectively accept paid travel as long as it’s disclosed. Sabrina Ortiz just went to Samsung Unpacked and MWC on partner-sponsored trips.

It looks like you took over The Deep View: Conversations podcast in an official capacity about a month ago. Are there new things that you want to experiment with in future episodes?

I love podcasting. Sabrina Ortiz and Nat Rubio Licht will host some episodes, too, so PR can pitch all three of us. We want natural, freewheeling conversations that feel like two friends catching up over coffee. If someone is the most polished speaker in the world, they might not be the right fit. We want people who are working on solving important problems related to AI.

I’m inundated with podcast pitches now, so I can’t respond to all of them. But people I’ve worked with before know how to get a hold of me on LinkedIn or via text. I’m always willing to consider a new guest who is a good talker and is passionate about chatting up AI.

Anything coming up that readers should know about?

The newsletter is truly a labor of love. And I love hearing feedback, good or bad. You can also follow my updates on AI in real-time on X or reach out on LinkedIn. Hearing from the audience is one of my favorite parts of the job.

Editor’s note: This piece was originally published in March 2026 and is being republished here as part of the launch of Sorry For Cold Calling.

Alex’s career is remarkable – from reporting at The Verge and running the Command Line newsletter to his work at The Information, Business Insider, and other outlets, breaking news about all the top tech companies.

The full transcript of the conversation is below, but if you only have time for a quick scan, check out my “Call Notes” for the points you can’t miss!

Call Notes

• Is the new, best path for everyone to become independent? Alex believes this career path won’t be for all up-and-coming journalists, due to the financial and career risks associated with being independent. He does anticipate a shift where new graduates will look to new media for jobs, rather than vying for the few opportunities at legacy outlets.

• Benefits of being “Alltogether”: Sources is part of Altogether, a new collective of independent journalists, including Alex, Alex Konrad, Casey Newton, Alex Kantrowitz, and Mosheh O., founded by AJ Frucci. Altogether bundles the scale of the collective to secure larger advertising budgets from major ad holding companies.

• Why Alex wants “good hangs” on the Access podcast: Alex and Ellis Hamburger are two friends with complementary backgrounds who started a podcast in partnership with Vox Media. If you haven’t tuned in, the banter between them is great. In terms of guests, they’re looking for “good hangs” with tech leaders. Their initial guest list has included Mark Zuckerberg, Dylan Field, Vlad Tenev, and more.

• Look out for Alex this year at CES, the World Economic Forum, SXSW, and other top tech events this year. He sees live events as a big part of his business and plans to hit the pavement in 2026.

• Pitching Sources?: Do your homework. He wants PR people to understand the spaces he covers and show why your executive should be in the mix with some of the most influential technology leaders today. Curveballs are appreciated, but do your research.

• More on being a “good hang”: Based on feedback from listeners, the best-received interviews are those where guests are authentic and vulnerable, not just delivering “talking points.” Alex and Ellis want more of this in 2026.

• AI predictions for 2026:

  • The collective conversation will focus more on world models (3D models that understand 3D spaces, controlling robotics, and agents).

  • The gap between ChatGPT and alternatives will narrow.

  • Sam Altman is predicted to no longer be the CEO of OpenAI this time next year.

I like to ask everyone who’s taken this path: Why start Sources now? Was there a moment or thought that sparked it for you? Were there any hesitations or fears?

[Starting Sources] is something I’ve been thinking about for a long time. So many of my friends have gone independent, and none of them have regretted it. I also knew how much fun it would be to start something of my own.

I’ve spent my career covering entrepreneurs who have founded tech companies. I thought, well, why not just give this a shot myself?

There was never going to be a perfect time to launch Sources. So, why not just do it? And also, things are moving so quickly with AI and what I cover. It’s a very consequential time. I knew I wanted to build this and grow this during this time. It couldn’t wait.

Seeing so many of your friends and peers be successful. Did that give you additional confidence?

Yes. Over the years, all of them have told me that, to their credit, they have more freedom, feel more creatively fulfilled, and make more money.

I know it’s a grind. And it’s not just about the content. It’s about the business. I’ve had to think more holistically than I did when I was part of a newsroom. To be successful, you really need a voice, brand, and platform that stand out. That’s very difficult to cold start if you’re not a known entity.

Everyone is increasingly realizing that you can own that platform. There’s definitely a sense of everyone saying, “Come on in the water, the water is warm.” It’s not easy, but it’s warmer.

I’m working more than I’ve ever worked, but it’s so rewarding.

Curious to get your take on this. Do you think legacy media will be leveraged as a pathway for independent journalism? Will up-and-comers use legacy media to build an audience and brand, then move on?

I’m not sure it becomes “the path” for most people. Most people don’t have the risk appetite to do what I and others have accomplished. Or, frankly, the ability.

I’m incredibly fortunate. My wife is the ultimate support system. Not everyone is in a position to take the kind of career risk or financial risk that comes with it.

Many people also still want to be part of a newsroom and team. They want to report and write. That’s why they got into this career path in the first place.

What I do envision happening, though, is that people coming out of school will increasingly look to some of these new brands to start their careers. They’ll just have more options. It won’t be that you have to go to one of the five (or so) New York media institutions that were always the path to a successful career. Those places are competitive, they only have a few spots, and you’re low on the totem pole.

We’re in this great unbundling phase in media, where people are going independent. It’s like the history of media; if you study it, it just goes back and forth.

Can you talk about your relationship with the new collective? I thought that was such a huge move. An explanation may be helpful for those unfamiliar with it.

Altogether is a new collective of independent journalists, like myself. AJ Frucci is the founder. He worked at Axios, Vox, and Puck. AJ has incredible experience in this space.

His idea, as he explained it to me, is to bundle together independent journalists who don’t have the scale of a large website and use that combined scale to open doors with the larger ad holding companies and brands. Basically, we’re all stronger together than we are on our own.

AJ handles the advertising. We’re both incentivized to grow ad revenue as quickly as possible while maintaining a high-touch approach. I want my audience to feel respected by me through ads that aren’t super intrusive or low-quality. I really prize my editorial independence, which AJ helps ensure by handling conversations with sponsors.

It’s great because he lets me focus on what I want to do, which is the work.

What’s one piece of advice you got while you were in the process of launching Sources?

Trust yourself. You didn’t leave and start your own thing so someone else could tell you how they think you should do what you do.

You know, it’s lonely. There’s a responsibility and weight with it. I still have to repeat it – trust yourself. That’s what I’m trying to practice.

You launched Access around the same time with your co-host, Ellis. How are you enjoying that? Between the show and Sources, do you feel pressure to produce content?

Access didn’t start because I had some creative idea for a podcast. I see podcasting as an essential medium for reaching my audience. I did a lot of podcasting at The Verge and Vox Media for different shows, and I always enjoyed that form of expression.

I’ve always known I wanted my own show, but I didn’t want to do it by myself. I didn’t want to do just another interview or solo show.

Ellis Hamburger and I have known each other for a long time. He’s a former tech journalist. We’ve almost overlapped several times in our careers.

Ellis also has a unique story because he went into tech. Ellis worked at Snap Inc. and The Browser Company. He’s now consulting for the buzziest AI startups with Meaning. Ellis just has a really unique vantage point on this space we cover. Not to mention, we’re friends.

Our goal for the podcast was to make it smart and insider-y. But we also want to give listeners a good hang. That comes with having great guests. Those guests, so far, have been big-name CEOs. Over time, though, you’ll see a lot of surprising guests that you may not be familiar with or you’ll see in a different light. We’re actually about to have our 2026 strategy planning.

Access is a nice complement to Sources. Sources is meant to be more scoopy, but with the pod, we just want to have a conversation. We want our guests to be a good hang for the listeners and us.

Tell me more about your planning session this afternoon. Anything you can preview?

We just did our first live show with Google Ventures. We definitely want to do more of that next year. We’ll discuss the opportunities and decide where we should lean in.

There’s also our recording setup. Do we move to an in-person show? Currently, we’re recording virtually. Do we move to a studio? Logistically, how would that work?

Then, we’ll talk about the future – how do we want to evolve the show? Do we want it to have the same feel? It’s our chance to review the data and see what’s working and not.

You’ve already landed several high-profile guests and interviews. What do readers need to know before pitching their executive? Equally as valuable, have you had a favorite interview so far, and why?

Look at what I’ve done before. There are so many pitches I get that make clear the person has not looked at the kind of guests I’ve had on and interviewed. Also, look at the caliber of them.

I do want curveballs. I want to be surprised and to have opportunities to meet individuals I wouldn’t have thought of. But the bar is high. I’ve published Q&A interviews with people like:

• Greg Brockman, the co-founder and president of OpenAI

• Demis Hassabis, CEO of Google DeepMind

• Daniel Ek, the founder of Spotify

That’s not to say I wouldn’t publish a Q&A with your startup founder. But that’s the caliber that you’re up against. Think hard about how you’re going to stand out. I have a finite bandwidth to interview everyone, so I need to be selective.

If you study my work, you can see through-lines, including the prediction markets and the consumer chatbot race. Leaning into those spaces will increase your chances as well.

Have you had a favorite interview so far, and what made it your favorite?

You know. It’s funny. We’ve had Mark Zuckerberg and Dylan Field on Access. Big, big, big names in technology. The podcast that we received the most feedback on was our interview with Raiza Martin. She’s the founder of an AI audio startup called Huxe. She led the vision and development of NotebookLM at Google.

Raiza really opened up to us on the podcast about her personal journey as an entrepreneur and the advice her husband has given her along the way. She was vulnerable about going out on her own, and being personal really resonates with listeners, especially in a podcast form. Authenticity is important.

We have public CEOs come on all the time who have their talking points, and it’s really challenging to get them off-script. No one wants to hear about the last earnings call.

That factor will influence how we book in the future. We’re actually going to start booking people who are not those kinds of interviewees. Because those are just better conversations. Before you pitch us for Access, consider if your executive can be a good hang.

How was the first live show? Are there plans to do more in the future? Could we see you and Ellis at some vendor user events in the future, recording the show?

We’re looking at CES, SXSW, and the other big tech conferences. Vox has been a great partner for that, especially getting us to SXSW. The goal is to do live shows with Access to engage with our audience.

I’m also planning to do some Sources Live events next year. I’ll be at Davos.

On Access, we don’t want it to be just an interview show. The best shows have a parasocial connection between the host(s) and the audience. You need to be sharing things about your life. You need to comment on topics in an entertaining and relatable way for listeners, while also being informative.

Do you have predictions for AI in 2026 and beyond?

I think we’re all, collectively, going to talk a lot more about world models in 2026. LLMs are still, obviously, very important, and will continue to be so. But I believe the conversation will shift toward 3D models that understand 3D and can therefore control robotics and agents in 3D spaces.

ChatGPT will remain the dominant consumer chatbot platform, but the gap between ChatGPT and alternatives will close. I don’t see them being the far-and-away leaders in 2026.

Sam Altman will not be the CEO of OpenAI this time next year. I’m not saying he won’t still be with the company, but I’d bet that he won’t have the CEO title.

Editor’s note: This piece was originally published in December 2025 and is being republished here as part of the launch of Sorry For Cold Calling. Some references reflect the time it was originally written.

The full transcript of the conversation is below, but if you only have time for a quick scan, check out my “Call Notes” for the points you can’t miss!

Call Notes

• From journalist to founder: Ron took a leap of faith to build FastForward, an entire publication from scratch. He paralleled pitching his new venture for the first time with the trials of being a startup founder – an interesting coincidence, given his years at TechCrunch.

• Mindset shift toward new media: In new media, Ron believes trust should be placed in the individual and their work. Initial skepticism from PR teams shifted to active engagement only once his first few profiles were published.

• Ron’s “AI Adventures” and reality check: Ron talked about his love-hate relationship with AI. Later, he divulged his prediction for 2026 that the AI bubble is primed to burst. Expectations for the technology have been blown out of proportion, and we’re in for a cold “AI November.”

• The “right” conference is a content goldmine: Ron emphasized the importance of content available on-site for him to consume and the invaluable “organic flow” that comes with being in person that virtual attendance cannot replicate.

• AI talk is becoming stale: Ron is eager to learn about other technologies in executives’ orbits that aren’t being talked about yet. He also plans to cover more of the startup journey in 2026.

You started FastForward in the first week of December last year. What’s one thing you learned about yourself during that process?

When I started, I had already been a journalist for a long time. I worked for existing platforms. And, for both me and the boldstart partners, that (FastForward) was a leap of faith on both sides.

They knew me through TechCrunch. I met Ed Sim and Elliot Durbin, who were and are the two principals for boldstart, about eight years ago. At the time, I was reporting on the New York City startup scene, and we established a connection then because they’re deep in enterprise technology. I covered them a lot because they funded cutting-edge enterprise startups (and still do), and I used them as sources.

When we discussed working together, they knew I could write an article and submit it to a platform with a staff of reporters at my side. But, they didn’t know if I could take something and build it. And frankly, I wasn’t sure either. I had built other things, but an entire publication, no. Getting FastForward off the ground was a challenge for me, from the design process of the logo to building the site and working with an outside firm.

I remember the logo. There were numerous minor iterations, but I liked that it stated “powered by boldstart”. I wanted the rest of the site to reflect that.

While that was happening, I was writing the first supply of content.

You’ve written for multiple platforms over the years. Can you compare the feeling of the first article you ever wrote to publishing your first on FastForward?

It was tremendously gratifying. We started with an idea. The whole thing was by the seat of our pants; you never know if it will truly work. And leaving TechCrunch, I had to pitch myself for the first time, especially for that first supply of content.

You mentioned in your anniversary post that the script was flipped with PR. What does your inbox look like today?

It was hard for me to read all the emails I received when I was at TechCrunch. I spent my mornings processing and asking, “Does this look interesting?”

Then, when I left TechCrunch, even though I had 10 years of experience and all that came with it, that didn’t seem to matter to those same people. I contacted PR teams, saying, “I have a new project, would you like to be part of it?” and they would respond that they want to see how it looks first. They were cautious. It felt very much like what a startup founder would face, convincing people that what they were doing was worth it.

I think you’d agree that a mindset shift is necessary with new media: people are trusting you and your work, not the outlet.

That’s right. I hoped that would be the case, but it wasn’t always. My theory was, once we got the first four profiles up on the site – Salesforce, Blackstone, Juniper, and PayPal – others would say, “Oh, this is cool. I want my executive on there.” And it worked. That week, when I launched, PR teams from prominent companies were in my inbox. I was confident, but I didn’t know what was going to happen. The second hurdle was publishing and seeing what happened with readership. There was also the newsletter that evolved throughout the year.

The newsletter continues to evolve. I published a newsletter before at FierceMarkets. I looked at more than a dozen newsletters from others for inspiration. I began with the original version, looking at industry trends. Over the last six weeks, I’ve reacted to news. I’m also using the newsletter to drive clicks back to the blog. I’ll never have the audience I had at TechCrunch again. I have a small fraction of that, but the audience is committed. And I think that’s the future of media. It’s small publications with small staffs, with committed audiences who cover niche topics.

Anyone you follow or admire?

Look at what Alex Konrad is doing at Upstarts Media, covering startups, or what Casey Newton is doing at Platformer. He covers those big AI platforms, and it’s just him. It’s amazing what he puts together every week. I’m so impressed with him.

Talk to me about your “AI Adventures.”

That was something I was doing on LinkedIn. In that section of the newsletter, I write about my experiences with AI. I want my readers to follow along with my AI discovery journey. Some of the things I use AI for are amazing. It helps with my research and speeds up my process as an individual, but there are still warts to AI.

Can you talk about experiments you’ve tried with the newsletter or blog? Compared to working at TechCrunch, the autonomy to try something and know the results, whether it worked or not, must be a big change.

I learned about blogging in 2003 at a blogging conference in Boston. The speaker was Rafat Ali, who had just started paidContent.org. He sold that to The Guardian. Then, in 2009, he started a travel website called Skift. So this was a person who knew a lot about publishing, but back then, he was just a guy. He obviously later became very successful.

I was trying to do the same then, when blogging was emerging. You didn’t have to beg at the door of the people who own the printing press or website anymore. After that conference, I literally went home and started a blog. I had it for 15 to 20 years. I only recently (in the last few years) shut it down. The ability to publish yourself is amazing. It brings back memories.

With FastForward, there’s pressure on me to produce all this content every week. I’m in a good rhythm now, but there’s a lot of work that goes into doing something yourself. There’s gratification, also, but there’s pressure to keep producing.

How is that different from working at TechCrunch?

One of the things I liked about working at TechCrunch was independence. When the management changed, that independence started to be pulled back.

How do you treat conferences? What is the bar to get you to travel?

It’s part of what I do for sure. I have to go out and make these relationships. Going to conferences has several benefits for me.

One is that I stay on top of trends, which I need to do to remain interesting. Two, I meet people, some of whom I could profile. Others can be sources for me to contact for comments.

I recently attended a one-day event because I was on the West Coast. That turned out to be incredible. I was there for six hours and ended up writing three pieces, so it was very useful. Sometimes you go for content, but usually it’s the act of networking that’s most helpful for me as a journalist.

How I pick and choose what I’ll go to: the content matters. I’ll look at the agenda and see who’s coming and what they’re talking about. That’s one thing. It has to be worthwhile and in my wheelhouse. There’s also the factor of the distance I have to travel. If it’s a one-day conference in San Francisco, I’m on the East Coast, so I’m not going to that, no matter how good it is.

One thing that gets forgotten is that your time is everything. You don’t have a team to fall back on. It’s all you.

You don’t have anybody to cover for you. Yeah, exactly. That’s another thing I take into consideration when I’m traveling. It puts more pressure on me to produce my content.

Sometimes I can write on an airplane, sometimes I can’t. It depends. Sometimes the person in front of you reclines, and then you can’t even open your laptop. I go in with the best of intentions. Or if the WiFi is wonky, then I can’t really work because I don’t have access to my transcript or collateral materials. There’s definitely that aspect of it.

I didn’t attend Dreamforce, but I still wrote about it. I watched the stream online and was pre-briefed on the news beforehand. Did I necessarily have to be there? No.

The difference being there, on the ground, is that you get the perspective. For Dreamforce, to get my perspective on Salesforce, I asked some sources for comments. But it’s not the same as having those conversations in the hall with fellow journalists, analysts, and others in the middle of it.

We learned during the pandemic that being together as humans is better than not.

I’ll be at re:Invent again this year. When I attend a conference like that, I like to do several things. I might not even sit in the auditorium during the keynotes because it’s just so crazy. I might sit in my hotel room and watch the stream. Then, I’ll go and talk to people and set up interviews, hopefully with individuals from AWS. Then, if I meet anyone at their events and parties, I enjoy chatting with them. It’s like a huge organic flow that happens in a flywheel because you’re on the ground and not virtual.

Speaking to CIOs and CTOs every week, what’s a constant that comes up in every interview?

Obviously, AI. We talk about AI an egregious amount. I’d prefer to change things up a little in upcoming interviews. I want to ask: What’s one thing that you’re thinking about that’s not AI? Every interview is starting to feel a little too similar, even though they’re all different and organic. You want to touch AI. AI is touching everything. So for me, it’s become let’s have an AI section of the conversation. I just don’t want the interviews to be that predictable, though.

So I’m thinking about how I can change up the interviews? Although AI is front and center in everybody’s mind. You can’t get away from it. It’s always, “How is it going to work?” “Are you finding that you’re getting a return on investment?” “How do you look at it?” “How do you talk to customers about it?”

The interesting thing about AI is that it’s very different from, say, Kubernetes or cloud computing. The difference is the CEO isn’t going to come to you as the CIO or the CTO and say, “I just read about Kubernetes. My kid is using it.”

Don’t get me wrong, we should be using AI. But with AI, everyone has an unreasonable set of expectations because it’s so accessible. And it wasn’t always that way. It used to be niche machine learning models and natural language processing. Now, all of a sudden, with generative AI, we’re all interacting with it either through voice or typing.

There’s a lot of pressure on the technology side of the house to make something happen because there’s so much FOMO from leadership.

One of the reasons I do my “Adventures in AI” series is to show people that the reality of using these tools does not match the hype. Not the executives I speak with, but too many others believe they can cut headcount because they have this technology. And I think that that’s the unrealistic expectations that those folks have to deal with.

We’re coming up on the end of the year, prediction time for many. I thought it would be fun to ask you if you’d like to make a prediction for next year. Will we still be talking about agentic AI 12 months from now? Will the AI bubble burst as many are predicting?

The AI bubble is going to burst. The amount of money being thrown around and poured into this, the amount of data center capacity they’re building, all under the belief that it will make AI smarter. I don’t think that’s true.

It’s not like software. When you upgrade software, you get more functionality. With AI, some barriers are tough to overcome when you hit them. I think we saw that with ChatGPT-4 and 5. We expected a huge leap, and we didn’t get it.

ChatGPT was a breakthrough, that’s undeniable. I remember in April 2023, I would go to conferences, and people would say, “Wow. If ChatGPT-4 is like this, I couldn’t imagine what 5, 6, and 7 are going to be like.” And, it doesn’t work that way. I don’t claim to be an AI expert. I’m a journalist. I talk to my people. I’m not technically savvy in that way. The individuals I trust say it doesn’t move in a straight line. There are detours where you hit a barrier, and it’s difficult to overcome that barrier. There’s this belief that brute force is the answer, but that won’t get us past those bumps.

We’re going to conclude not too far into the New Year that maybe we need to put the brakes on. I don’t think it’ll be like an AI Winter, where it will be a decade before we return to AI. I think it’s going to be an AI November, where the masses will hunker down and rethink their strategies because right now, the hype doesn’t match the reality.

Editor’s note: This piece was originally published in November 2025 and is being republished here as part of the launch of Sorry I Cold Called You. Some references reflect the time it was originally written.

I’ve spent more than a decade in tech PR, working with late-stage companies and Fortune 500 brands to turn dense, technical products into stories people actually want to read. That work has helped executives and companies appear in some of the top business and technology outlets globally.

This Substack is where I’m exploring the changing media landscape, specifically, the shift from established media brands to individual voices with devoted audiences. To give peers a peek behind the curtain, I’ll be “cold calling” journalists who left top outlets to build independent platforms and asking what they’ve learned about audience-building, storytelling, business models, and the future of media.

It’s for PR people, founders, journalists, and anyone trying to understand where attention is moving next.