If you’re new here, Friend Of is about gays, power, and their influence on culture and business. The name is a nod to the phrase “a Friend of Dorothy,” once used to quietly ask if someone was gay. If you’re reading this, you’re a friend of mine.

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It’s Monday evening at 5:00 in New York City and the 6’5”, blue eyed, men in finance — or at least the gay and curious ones — tiptoe out of their hellish investment banking offices, walk across some cobblestone-lined streets in FiDi, loosen up their ties, and line up for a Very Important “Board Meeting.” That’s the plan, at least.

A few weeks ago, a Friend Of this newsletter sent me the Board Meeting’s Instagram. Comments, reddit threads, and the group’s 400-member WhatsApp are rightfully confused whether this is a sex party, a formal networking event, or something else. I went straight to the source, and asked Sam Wilson, the man behind it all.

Sam, who does creative direction for brands, started The Board Meeting with his friend, Jason, an architectural designer who works in FiDi. They realized there isn’t a gay bar in FiDi for “gays who are professional but who are not into the nightlife scene” or, said differently, “guys who don’t feel represented in Brooklyn on a Saturday night or Hell’s Kitchen on a Thursday.” Reasonable. Some of the gays in finance, Sam tells me, may not be interested in the scene at all — or out in the workplace — and may “prefer discretion and a more low-key vibe.” I think it’s smart, differentiated, and not far off from where this newsletter got its name: ‘Friend of Dorothy’ was a widely understood code phrase that once allowed for gay men to recognize one another while maintaining plausible deniability.

So far, they’ve called four board meetings and are taking a “pop-up style” approach, with this Monday’s meeting being held at the Highwater Rooftop at 120 Water Street. Sam described the demographic so far as “early to mid-20s, younger professionals who want to go out after work until 9:00 or 10:00pm.” While it starts at 5:00pm, he expects people to trickle in after work until 6:30/7:00pm.

I’m planning on going — reply to this email if you wanna join

Here’s what the power gays are up to

• ‘Be greedy when others are homophobic.’ That’s the investment strategy for one guy buying Grindr’s stock. Grindr’s CEO, George Arison, told Pomp that two different investors discount Grindr’s stock by 25% because straight portfolio manages may not want to pitch Grindr to their bosses or clients

• Derek Chadwick ducked out from Goose, the company he helped start, saying he’s “no longer involved in any capacity.” The much-hyped gay dating app launched less than 60 days ago but has come under tons of scrutiny for creating fake AI profiles, updating its Terms of Service around photo ownership, and running bizarre “organic” TikTok campaigns to promote the service. It’s odd because the pre-launch and offline marketing was so well done. They held really tasteful events, and sprung up coffee and hot dog pop-ups in Miami, LA, and NYC, but their judgment for growth hacking is clearly misguided

• The WSJ featured Chipotle’s founder, Steve Ellis, for its My Monday Morning series (one of my favorites). I learned he started a NYC sandwich chain called Counter Service, with one of Peloton’s founders. They make bread from scratch every day

• Rumors of Keith Rabois’ “relocation” from Miami to NYC in Axios are mostly false. He tells me he’s remaining an FL resident but splits his time each month among NYC, Miami, SF, and DC. Catch him at 6am Aarmy or Barry’s

• Speaking of Barry’s, they just emailed instructors about a new non-compete policy, barring them from teaching other fitness classes. Instructors are upset and taking to TikTok and reddit

• The Shards, the new show from Ryan Murphy, is predictably good, gay, and gruesome

• Gwyneth Paltrow may or may not be hosting an al fresco dinner at her Amagansett home “in honor of” OpenAI cofounder Sam Altman. The invite states it’s “off-the-record.” This is weird, right? Anyways, she’s having fun with rage-baiting the internet on her Instagram

• Mitchell Jackson, the outspoken celebrity publicist, is back representing Clavicular. Mitchell and I grabbed breakfast the other week as we overshared about our personal lives. He’s hilarious

• The founders of Whatnot, the live shopping site that started out with Funko Pops (??), have a lot to celebrate. The company’s now worth $20 billion

• Bowen Yang takes over as Mary Todd Lincoln in Broadway’s Oh, Mary! from September 15—December 6

• Chris Appleton’s Cotswolds home got the AD treatment. It’s stunning. I need to get into the hair business.

• Kevin Harrington started a new entertainment marketing agency, Patrick Patrick. He previously led social strategy for Love Island US and was the campaign lead for SNL50

• Grant Gibbs, the “Twink” half of “Twink and Redhead,” just signed with CAA. If you’re hyper-online like I am, you know that Grant was the one who, depending on who you ask, outed the Crumbl co-founder…

• Derek Blasberg published a hardcover book featuring hundreds of old photographs from his days writing a column for Interview Magazine

• Meadow Lane’s Sammy Nussdorf was profiled in The New York Times

• GQ’s Charlie Sosnick has a fun piece about how men are getting into spray tans: “staying tan telegraphs that you exercise outdoors, or can afford beach and ski vacations, or are not chained to a desk 24/7”

xo

JACK RANDALL

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Friend Of is about powerful gays influencing business and culture. Gays have shaped culture, fashion, and media for decades, but recently, we’ve ascended into two other centers of power: technology and government. We’re wealthier and more educated than the general population. And we run fashion houses, tech companies, the Treasury, primetime, and late-night news. That’s worth writing about. The name is a nod to the phrase “Friend of Dorothy,” once used to quietly ask if someone was gay.

Disclaimer: References to individuals do not imply orientation. Don’t come for me; I am lawyered up.

We survived the first half of Pride month. I like to say that being gay is a full-time job. Being gay in NYC, during Pride, and especially if you have any interest in sports, feels like working overtime.

I’ve heard of three new approaches to gay member clubs and dating apps in the last 30 days. While each one takes a slightly different approach, they’re all focused on building stronger platonic, professional, or romantic connections. They all emphasize in-person events or experiences, and they’re all either invite-only or priced like a luxury good.

If your Instagram feed is anything like mine, you’ve seen promotions and teasers for Goose, the new app “for the boys.” Derek Chadwick, the influencer and actor who also started his Chaddy Cosmetics line, is behind it, along with David Aliagas, who previously worked with BeReal and Partiful. Goose is an invite-only dating app for gay men. A gay Raya, of sorts. Goose says guys can wave to each other in the app, but the intention is for them to have a “social-first” mindset rather than a romantic or hookup-focused one.

Grindr is testing an “invite-only luxury experience” for its most engaged users, offering more functionality and profile visibility in the app, as well as events and curated intros. I hear it may cost $4k-$6k per year or more.

I just learned that next week Josh Adan, is launching Adan & Cie, a “private, invitation-only experience firm.” Josh comes from luxury hospitality: Jean-Georges, The Mark Hotel, and Thomas Keller. I expect his company will make curated introductions among members, but focus more on romantic connections.

Sector, the popular private community for gays, focuses on curated 1:1 introductions and in-person events. Brian Tran, the founder, opted for text-based messaging with its concierge, Neil, who makes intros over text and invites you to everything from a talk on longevity and peptides to a party at Boom and a rooftop dinner in Brooklyn. Since Sector launched in January, I’ve made many friends and professional connections and gone on three dates with Sector members. Thank you, Brian.

• Founders Fund, the VC firm started by Peter Thiel, premiered MAFIA, where they flex their Rolodex (and portfolio). OpenAI’s Sam Altman, Anduril’s Palmer Luckey, longevity guy Bryan Johnson, and Figma’s Dylan Field are some of the players. It’s wildly entertaining to watch some of the best entrepreneurs hang out and drink, not talk about work, and, of course, as the game calls for, lie and deceive one another. Mike Solana, Founders Fund’s CMO, is the brainchild here. Episode one has 3.2M views on X

• Peter Thiel has lots to celebrate: Founders Fund’s ~$600M investment in SpaceX over the years is worth ~$70 billion. I want to see Peter play Mafia next

• Call Me By Your Name is back in AMC theaters until Friday

• Leviticus is a new Australian film out in theaters this Friday. It’s a gay romance-horror, so basically a documentary. Happy pride

• GLAAD is raising funds with an old-fashioned eBay auction. Items range from tickets to Titanique, Hilary Duff, and Sam Smith, but the item with the most bids and the highest bid is Rob Rausch’s worn overalls

• Match Group, the parent company behind Tinder, Hinge, and many other dating apps, is investing $100 million into Sniffies. The press release describes Sniffies users as “non-heterosexual men.” Describing a group by what they aren’t is weird!

• The Crumbl cookie founders are stepping back from their day-to-day roles but will keep their board seats. As with matcha drinkers, I don’t believe anyone who says they like Crumbl cookies

• Bari Weiss’ reign at CBS and 60 Minutes continues to be filled with drama, firings, newsroom infighting, and rage-quitting. I watch 60 Minutes every Sunday and have immense respect for how deeply they report each story. Anderson Cooper left to (actually) spend more time with his kids. Here’s a beautiful tribute to his time there

• Spotify has a new Pride playlist, titled GLOW. It already has over 1 million saves. I listened to it while writing this, and it’s quite gay

• Grindr and Madonna continued their partnership to announce her new album, Confessions II. They threw a surprise concert in Times Square and kindly invited me. It was fab, and so was the after-party at The Edition. Grindr’s CEO, George Arison, says Madonna’s team reached out first, and he initially thought it was spam

• U.S. Treasury Secretary Scott Bessent says 6 million children are signed up for Trump Accounts. I love this initiative because it gives kids upside in our great stock market, but also because my former employer, Robinhood, helped design the app and bring it to life

• Tim Cook hosts his last WWDC at Apple

• David Hockney passed away. Here’s a great obit on his life

• Jacob Tierney says Heated Rivalry Season 2 is coming next April

• Antoni Porowski has a new show, Best of the World, where he travels to and dines in Paris, CDMX, and NYC

• Lightspeed’s CMO, Josh Machiz, also debuts a new show, called Lightwork. They recently hired Claire Zau, an investor and content creator with 350k+ followers, as co-host

• CAA and TPG launch a $250M creator fund, under the name Compound. Tucker Brown from CAA runs it and says they’ll back creators across TikTok, Instagram, and Substack who are making $10M+ annually

xx,

JACK RANDALL

Friend Of is about powerful gays influencing business and culture. Gays have shaped culture, fashion, and media for decades, but recently, we’ve ascended into two other centers of power: technology and government. We’re wealthier and more educated than the general population. And we run fashion houses, tech companies, the Treasury, primetime, and late-night news. That’s worth writing about. The name is a nod to the phrase “Friend of Dorothy,” once used to quietly ask if someone was gay.

Disclaimer: References to individuals do not imply orientation. Don’t come for me; I am lawyered up.

Friend Of is about gays, power, and their influence on tech and culture. The name nods to the phrase “a Friend of Dorothy,” once used to quietly ask if someone was gay. If you’re reading this, you’re a friend of mine.

Subscribe now

I was in Washington, D.C. over the weekend to see friends and go to parties celebrate the media and the First Amendment. One of the most-talked-about parties surrounding the White House Correspondents’ Association (WHCA) Dinner wasn’t hosted by a media organization. Instead, it was a party hosted by Grindr at a lavish estate in Georgetown. Throughout the mansion and gardens, Republicans and Democrats alike rubbed shoulders and enjoyed the scene.

A few notable attendees: CNN host Kaitlan Collins; Nebraska Senator Deb Fischer; Grindr CEO George Arison; DNC Chair Ken Martin; Don Lemon; Jim Acosta; the Pod Save America hosts; Taylor Lorenz of User Mag; RHOSLC star Bronwyn Newport; and author and columnist Jamie Kirchick.

The party was stocked with caviar, burgers, and fries, and servers walked around serving oysters alongside an ice sculpture carved to resemble Grindr’s mask logo. Drinks were flowing, as expected: Grindr had three bars and hired buff bartenders who were brand-new to bartending. Few complained about that, but one guest complained to me that there were “way too many women.” Another said, “Not enough twinks.” Don Lemon had a more thoughtful take:

“Black people and gay people are always leading in culture, and so it’s appropriate that we are here. Grindr’s been ahead of the curve and now people are catching up and it’s the most sought-after party.”

The next day, I watched C-SPAN while chaos erupted during the WHCA dinner. Shaken up but still poised and professional, the WHCA President said something that stuck with me: “…journalism is a public service, because when there is an emergency, we run to the crisis, not away from it. And on a night when we are thinking about the freedoms in the First Amendment, we must also think about how fragile they are." I was impressed but not surprised to see how quickly and responsibly the media covered the event from inside the ballroom, where moments before they could’ve been targets or casualties. I’m glad everyone was kept safe. I want a ticket to the next one.

Here’s what else is happening

• Tim Cook will step down as Apple’s CEO and become Executive Chairman on September 1st. As an Apple fanboy since childhood, I was lucky enough to intern in Apple’s PR department, and have always admired Tim Cook. Yes, he increased shareholder value, grew their services business tremendously, introduced the Apple Watch and AirPods, and was an operations genius, but it was his commitment to ethics and principled leadership that always stood out to me.

  • He’s a very private person but bravely came out as gay in 2014 in a beautifully written essay published in Bloomberg Businessweek. It impacted me a great deal, and I’ve gone back to read it several times since. He was the first openly gay CEO of a Fortune 500 company. I pasted the full text below, but here are excerpts:

    …let me be clear: I’m proud to be gay, and I consider being gay among the greatest gifts God has given me.

    Being gay has given me a deeper understanding of what it means to be in the minority and provided a window into the challenges that people in other minority groups deal with every day. It’s made me more empathetic, which has led to a richer life…It’s also given me the skin of a rhinoceros, which comes in handy when you’re the CEO of Apple.

    I don’t consider myself an activist, but I realize how much I’ve benefited from the sacrifice of others. So if hearing that the CEO of Apple is gay can help someone struggling to come to terms with who he or she is, or bring comfort to anyone who feels alone, or inspire people to insist on their equality, then it’s worth the trade-off with my own privacy.

  • He made Apple’s devices more accessible and directed them to do more with Health and Fitness. Answering a shareholder’s question, he said: “When we work on making our devices accessible by the blind, I don’t consider the bloody ROI. If you want me to do things only for ROI reasons, you should get out of this stock.”

  • He prioritized user privacy through iOS and macOS and famously refused to create a digital backdoor for the FBI to access the iPhone of the San Bernardino shooter.

  • He pushed Apple to take on big environmental and sustainability efforts: achieving 100% renewable energy on all facilities, expanding the recycling program, making suppliers commit to clean energy…

  • I hope he finds more time to enjoy his compound at the Madison Club in Palm Springs. (The New York Post)

• Sam Altman was the unfortunate subject of a big Ronan Farrow profile in The New Yorker. Days later, people targeted his home with a Molotov cocktail and a round of shots. Last night, OpenAI published a blog post about what principles it stands for. AI has a PR problem. Reversing it requires a lot more than writing 1,000 nice words. (The New Yorker, The San Francisco Standard, OpenAI)

  Altman interrupted his “war room” at six o’clock each evening with a round of Negronis. “You need to chill,” he recalls saying. (The New Yorker)

• Celebrity publicist Mitchell Jackson dropped Clavicular as a client after his recent overdose: “I’m doing this as a plea for his health.” He also debunks the semi-niche rumor that Peter Thiel had been funding Clavicular. (NYT, X)

• Kara Swisher got a new show on CNN, “Kara Swisher Wants to Live Forever”, and it follows her interviewing Bryan Johnson and others about health and longevity. It has the same Kara-snark you expect (and either love or hate!). (Instagram)

• The Thiel Foundation released its 2026 class of Thiel Fellows. They get $250,000 over two years to build their startup. RIP to their DMs. (X)

• Madonna announced a collab with Grindr on Friday to promote her upcoming album, Confessions II. Madonna appeared on users’ grids, likely next to a sea of torsos, offering Grindr users a special vinyl picture disc. (Billboard)

• Tech’s favorite coffee chain, Philz Coffee, did an about-face after removing pride flags from some of its locations. People were upset. They course-corrected days later. I can’t imagine this happening if they hadn’t sold to private equity last year. (The Guardian)

XX,

JACK RANDALL

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Tim Cook Speaks Up

October 30, 2014 (Bloomberg)

Throughout my professional life, I’ve tried to maintain a basic level of privacy. I come from humble roots, and I don’t seek to draw attention to myself. Apple is already one of the most closely watched companies in the world, and I like keeping the focus on our products and the incredible things our customers achieve with them.

At the same time, I believe deeply in the words of Dr. Martin Luther King, who said: “Life’s most persistent and urgent question is, ‘What are you doing for others?’ ” I often challenge myself with that question, and I’ve come to realize that my desire for personal privacy has been holding me back from doing something more important. That’s what has led me to today.

For years, I’ve been open with many people about my sexual orientation. Plenty of colleagues at Apple know I’m gay, and it doesn’t seem to make a difference in the way they treat me. Of course, I’ve had the good fortune to work at a company that loves creativity and innovation and knows it can only flourish when you embrace people’s differences. Not everyone is so lucky.

While I have never denied my sexuality, I haven’t publicly acknowledged it either, until now. So let me be clear: I’m proud to be gay, and I consider being gay among the greatest gifts God has given me.

Being gay has given me a deeper understanding of what it means to be in the minority and provided a window into the challenges that people in other minority groups deal with every day. It’s made me more empathetic, which has led to a richer life. It’s been tough and uncomfortable at times, but it has given me the confidence to be myself, to follow my own path, and to rise above adversity and bigotry. It’s also given me the skin of a rhinoceros, which comes in handy when you’re the CEO of Apple.

The world has changed so much since I was a kid. America is moving toward marriage equality, and the public figures who have bravely come out have helped change perceptions and made our culture more tolerant. Still, there are laws on the books in a majority of states that allow employers to fire people based solely on their sexual orientation. There are many places where landlords can evict tenants for being gay, or where we can be barred from visiting sick partners and sharing in their legacies. Countless people, particularly kids, face fear and abuse every day because of their sexual orientation.

I don’t consider myself an activist, but I realize how much I’ve benefited from the sacrifice of others. So if hearing that the CEO of Apple is gay can help someone struggling to come to terms with who he or she is, or bring comfort to anyone who feels alone, or inspire people to insist on their equality, then it’s worth the trade-off with my own privacy.

I’ll admit that this wasn’t an easy choice. Privacy remains important to me, and I’d like to hold on to a small amount of it. I’ve made Apple my life’s work, and I will continue to spend virtually all of my waking time focused on being the best CEO I can be. That’s what our employees deserve—and our customers, developers, shareholders, and supplier partners deserve it, too. Part of social progress is understanding that a person is not defined only by one’s sexuality, race, or gender. I’m an engineer, an uncle, a nature lover, a fitness nut, a son of the South, a sports fanatic, and many other things. I hope that people will respect my desire to focus on the things I’m best suited for and the work that brings me joy.

The company I am so fortunate to lead has long advocated for human rights and equality for all. We’ve taken a strong stand in support of a workplace equality bill before Congress, just as we stood for marriage equality in our home state of California. And we spoke up in Arizona when that state’s legislature passed a discriminatory bill targeting the gay community. We’ll continue to fight for our values, and I believe that any CEO of this incredible company, regardless of race, gender, or sexual orientation, would do the same. And I will personally continue to advocate for equality for all people until my toes point up.

When I arrive in my office each morning, I’m greeted by framed photos of Dr. King and Robert F. Kennedy. I don’t pretend that writing this puts me in their league. All it does is allow me to look at those pictures and know that I’m doing my part, however small, to help others. We pave the sunlit path toward justice together, brick by brick. This is my brick.

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Friend Of is about powerful gays influencing business and culture. Gays have shaped culture, fashion, and media for decades, but recently, we’ve ascended into two other centers of power: technology and government. We’re wealthier and more educated than the general population. And we run fashion houses, tech companies, the Treasury, primetime, and late-night news. That’s worth writing about. The name is a nod to the phrase “Friend of Dorothy,” once used to quietly ask if someone was gay.

Disclaimer: References to individuals do not imply orientation. Don’t come for me; I am lawyered up.

I moved (back) to NYC and couldn’t be happier about it. My first year and a half here was cut short when I moved to the Bay Area for a startup, but after I quit, I realized I could just… go back? So I did. I bought my first place in downtown Manhattan and moved in 12 days ago. I immediately liked the place when I toured it and knew I had to buy it: the location is perfect, it has uninterrupted views, a shared rooftop, and most importantly, lots of natural sunlight. The flip side of homeownership, I’m quickly learning, is that I am responsible for everything. I’m currently getting swindled by window repairmen and locksmiths.

The other day, I was sifting through the mail and saw an envelope addressed to Emily Weiss, the Glossier founder. After some Google searching, I confirmed she once lived in my condo while writing Into the Gloss, which famously evolved into Glossier. Good lore for a first home.

Here’s what other gays have been up to:

• Earlier this week, Jacob Helberg, Under Secretary of State, hosted the 3rd annual Hill & Valley Forum in D.C. I went last year, and I remain struck by his ability to draw in the biggest names in tech, finance, and government. (Newcomer)

• Barry Diller just paid $11 million for JFK’s former NYC penthouse at The Carlyle. The Love Story effect? (WSJ)

• Chappell Roan got herself in some hot water, but a bodyguard to many other celebs just took the blame for berating Jude Law’s kid, saying he acted on his own and wasn’t part of Roan’s security that day. This incident caused Roan to have to utter: “I don’t hate children. Like, that is crazy.” (Page Six)

• Trump confirmed that the CIA told him the new Iranian leader is gay. “I think a lot of people are saying that, which puts him off to a bad start in that particular country.” (New York Post)

• Mike White, creator of The White Lotus, joined the cast for Survivor’s 50th season. You read that right, and I’ve watched each one. He was runner-up on a 2018 season, years before he created The White Lotus. I won’t spoil anything in case anyone else is a Survivor fan, but he’s great television.

• Marc Jacobs is the subject of a new documentary, the first by Sofia Coppola. It’s appropriately called Marc by Sofia.

  WSJ Mag: What’s the secret to a happy marriage?

  “Yes, dear.” [Laughs] I think saying yes and moving on is a good way to avoid a short relationship. No, we do couples therapy and I think we know each other well enough to know when to leave the other person alone and give it space. We work on repair as opposed to screaming and yelling or fighting or disagreeing.

• Sam Altman’s OpenAI is rumored to be raising an additional $10 billion, which would value the company at $850 billion. When I was in middle school or high school, I remember how crazy it was that Facebook bought Instagram for $1 billion. Now, we’re seeing $10 billion rounds. (Bloomberg)

• Mark Guiducci, Vanity Fair’s editorial director, recently hosted his first VF Oscars party. To apply for the top editorial role, he wrote a 57-page memo on how he’d run the magazine. (The Financial Times)

• Pete Buttigieg has a new profile in The Atlantic. A scruffy beard, a simple black coffee, and crouched over at a local diner. Looks like a man who wants to run for something.

• Troye Sivan joined Substack and seems to be using it as a stream-of-consciousness. He purged all other social and dating apps. He’s stronger than I am.

  I deleted instagram, TikTok (ages ago), and the dating apps on my phone to free up space in my mind, accept my loneliness, boredom, emotional vulnerability, and stop numbing myself. The issue is of course that I now have space in my mind, am lonely, bored, emotionally vulnerable and not numb.

Reply with any of these, and I’ll love you forever

• guest ideas for my upcoming Q&A series

• designer for Friend Of branding work

• interior designer or contractor in NYC

xx,

JACK RANDALL

Friend Of is about powerful gays influencing business and culture. Gays have shaped culture, fashion, and media for decades, but recently, we’ve ascended into two other centers of power: technology and government. We’re wealthier and more educated than the general population. And we run fashion houses, tech companies, the Treasury, primetime, and late-night news. That’s worth writing about. The name is a nod to the phrase “Friend of Dorothy,” once used to quietly ask if someone was gay.

Disclaimer: References to individuals do not imply orientation. Don’t come for me; I am lawyered up.

Welcome to Friend Of, about powerful gays influencing tech and culture. The name is a nod to the phrase “Friend of Dorothy,” once used to quietly ask if someone was gay. If you’re reading this, you’re a friend of mine.

People are upset!

WIRED published a 5,000 word essay titled “Inside the Gay Tech Mafia.” (free version here). It’s basically the extended version of this newsletter. I was early!

The piece dives into what many people in tech already know: there are founders, operators, and investors who have become very successful — and happen to be gay. They are friends. They work out and vacation together. They support each other. They sometimes date and sleep with each other.

The writer is on the tech culture “beat”, and often writes colorful, fly-on-the-wall stories like this Vanity Fair one about the 20-year-olds building defense and hardware startups, the absurd Sperm Racing, and “Inside Burning Man” from 2018.

The gay mafia one struck a nerve.

I saw a wide range of takes online and from friends, from neutral and balanced to dramatic and thin-skinned:

• what’s wired?

• i can’t read it, it’s paywalled

• it’s way too long, i didn’t read it

• the photos are funny

• the photos are distasteful

• the photos are homophobic

• it was a nothingburger

• it was amusing

• it was a hit piece

• i canceled my wired subscription

• it’s disgusting and homophobic!

I scanned hundreds of comments about the article on X, Instagram, and Reddit. Many people had surface-level comments about the photo choices. (WIRED’s photo team successfully rage-baited you). Others lobbed lazy comments like “this feels homophobic” (emphasis mine). I doubt these people read even half of the article. My group chats and side chats with gay friends found it entertaining. Interestingly, it was more of my straight friends who found it upsetting.

I was not offended by it. I found it to be a fun and entertaining ride. Yes, many of the quotes were exaggerated hyperbole, and I didn’t relate to several aspects of what others described, but I think it’s a directionally correct look at the gay tech subculture.

If you read the whole thing, what do you think? Please take my oversimplified poll.

Some of the discourse:

xx,

JACK RANDALL

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Friend Of is about powerful gays influencing business and culture. Gays have shaped culture, fashion, and media for decades, but recently, we’ve ascended into two other centers of power: technology and government. We’re wealthier and more educated than the general population. And we run fashion houses, tech companies, the Treasury, primetime, and late-night news. That’s worth writing about. The name is a nod to the phrase “Friend of Dorothy,” once used to quietly ask if someone was gay.

Disclaimer: References to individuals do not imply orientation. Don’t come for me; I am lawyered up.

Welcome to Friend Of, about powerful gays influencing tech and culture. The name is a nod to the phrase “Friend of Dorothy,” once used to quietly ask if someone was gay. If you’re reading this, you’re a friend of mine.

Subscribe now

Just last week, my friend Brian Tran hosted a launch party for his new company, Sector. He’s building a “private network for gays around the world” and wanted to officially unveil the brand and celebrate the 100 Founding Members.

He didn’t disappoint.

About 150 well-dressed, high-IQ and high-EQ men — and two women, by my cursory scan four drinks deep — mingled in a beautiful Tribeca home featuring an original Keith Haring mural. I saw lots of Prada, some Thom Browne, and Saint Laurent boots. Brian also printed a collectible magazine, introducing Sector and spotlighting the early members. A bunch of us went to a party at Boom after.

Here’s my debrief with Brian:

You just had your Sector launch party — how are you feeling a few days later?
I’m on cloud nine, but also overwhelmed with the amount of membership requests and inquiries. Someone lend a hand — or a lorazepam.

Any memorable fashion statements or brands you saw?
Everyone delivered! My personal fave was a Saint Laurent smoking jacket with a t-shirt and Levi jeans.

Any hookups or dates stemming from the party?
What happens at Sector stays at Sector!

Where’d you find those very good-looking servers and bartenders?
Scott Breschini is a Sector member and has a hospitality company that can deliver anything you need. Chic glasses, camera-ready bartenders, piles of artisan ice, you name it.

Tell me about the Sector members. Who are they?
The most kind, handsome, and successful guys you haven’t met yet. Because they’re not on Instagram or the apps. We have Olympic athletes, startup founders, Fortune 500 CEOs, celebrated photographers, and film directors as members.

How can people join Sector? Is there a waitlist?
The best path is to get a referral from one of our 100 founding members. But you can also submit an inquiry through our website. We’re looking for our next 100 members right now, actually.

What’s the grand vision for Sector?
Every gay is on Sector and we curate your world. I think we could displace Grindr in the coming years.

When can we expect another party or event?
Mark your calendar for the end of February. We’re debuting Sector Stories, which will be unfiltered conversations with the most fascinating and ambitious voices in our community. Hear how they went from 0 to 100, then stay for cocktails, music, and connections.

I’m calling it now: in the future, all well-to-do, cosmopolitan gays will be Sector members and Friend Of subscribers.

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Here’s what the gays have been up to:

• Pillion makes Heated Rivalry look like a kids’ movie. While I was in NYC, I went to an early screening of Pillion, the new A24 BDSM movie starring Alexander Skarsgård and the actor who played Neville from Harry Potter. God took his time with Skarsgård. I kinda loved the movie. Other people did too: it has 100% on Rotten Tomatoes. It was steamy, funny, heart-warming, sad at times, and British the whole time.

• Ryan Murphy’s new show, Love Story, about John F. Kennedy Jr. & Carolyn Bessette, comes out on Thursday. He’s been busy: he just released The Beauty with Ashton Kutcher, and last fall, he had All’s Fair with Kim Kardashian and the Monster/Ed Gein show releases.

• Michael Kors was featured in one of my favorite columns, WSJ’s My Morning Routine. Some banger quotes:

  I first wake up at 5:30. I will quickly scroll Instagram to see if there’s anything interesting, and I look at the headlines from you guys, the Times, Women’s Wear Daily and Puck. Then I fall back asleep and get up around 7:00.

  I have breakfast together with my husband every morning. We’re together 24/7. We’re the human version of swans.

  If I’ve been a good boy all weekend, I’ll have an everything bagel, but if I’ve been a bad boy all weekend, I have a vanilla protein shake.

It’s personal

• Feed Me’s Emily Sundberg gave Friend Of a shoutout in her West Coast Edition. I stop mid-task whenever a Feed Me notification hits my phone.

  A newsletter about powerful gay guys in tech. SF-based comms advisor Jack Randall started a newsletter called Friend Of. He told me, “Friend Of is about how powerful gays influence tech, business, and culture. There’s riches in the niches and the gays are very rich...but the newsletter is for girls, gays, and anyone who works for powerful gays, which is probably a lot of people.” I wish some of you were this clear with the purpose of your newsletters.

• Andreessen Horowitz announced its inaugural New Media Fellows, and I’m lucky to be among so many greats. It’s being dubbed “the Thiel Fellowship for the terminally online.”

• I did a Q&A about tech PR with SBS Comms, one of my fave agencies. I told PR people to get a backbone.

xx,

JACK RANDALL

Friend Of is about powerful gays influencing business and culture. Gays have shaped culture, fashion, and media for decades, but recently, we’ve ascended into two other centers of power: technology and government. We’re wealthier and more educated than the general population. And we run fashion houses, tech companies, the Treasury, primetime, and late-night news. That’s worth writing about. The name is a nod to the phrase “Friend of Dorothy,” once used to quietly ask if someone was gay.

Disclaimer: References to individuals do not imply orientation. Don’t come for me; I am lawyered up.

Welcome to Friend Of, about powerful gays influencing tech and culture. The name is a nod to the phrase “Friend of Dorothy,” once used to quietly ask if someone was gay. If you’re reading this, you’re a friend of mine.

I somehow got into sports betting, so now I’m writing this gay newsletter while watching straight men play football. I lost $300 on the Indiana game.

Here’s what the gays have been up to:

• People are pretending to be gay in San Francisco to get VC funding, according to the host of the ‘niche and unserious podcast’, Members of Technical Staff.

  “Don’t come to SF and try and pretend to be gay…they will get you to prove it. They are some of the most powerful people in San Francisco and so, therefore, the world. ‘If I could come across as gay maybe I could raise my seed round.’ Don’t do that. Their culture is not your costume.”

• Heated Rivalry has become quite the phenomenon, especially among women. I hope the takeaway isn’t: make more sports dramas. It’s simply to make hot people have hot sex on television. That’s it. The show is “the most-watched non-animated show acquired by HBO Max” (The New Yorker). It’s rated 99% on Rotten Tomatoes. For a time, hard copies of the book were sold out.

  “On Dec. 22, four days before the finale streamed, 53 percent of the show’s viewers were female, an HBO spokesman said. By the end of last week, roughly two-thirds of the viewers were women.” (The New York Times)

• Related, Hollywood has been cranking out new shows with gay main characters and plotlines: Heated Rivalry, Boots, Hunting Wives, Pluribus, and Stranger Things come to mind.

• Grindr might become the Goop for Gays. A reporter got hold of an internal memo outlining plans to expand into lifestyle and DTC products. From the memo: ‘Our users have significant disposable income and are spending it on DTC products and services elsewhere — e.g., medications; wellness and fitness products; luxury experiences; travel; networking.’ Grindr already sells ED medicine, masterfully named Woodwork (Business Insider)

• Fashion designer Valentino passed away at 93. “When travelling on his 14-seat Challenger jet, Valentino and his entourage went to the airport in three cars: one for the staff and luggage, one for five of the pugs, and one for Giammetti, Valentino, and the pug Maude, who always travelled with Valentino.” (Wikipedia)

• Feed Me’s new podcast had the Meadow Lane founder on to talk about the highs and lows of opening his gourmet grocer and building in public. One thing he said struck me: “Some people have this misunderstanding of Meadow Lane as a status symbol and it’s so far from that.” If I wanted to build a high-end brand, that’s exactly what I’d say too. (Expense Account)

• Looksmaxxer and the current ragebaiter, Clavicular, says gay actor Matt Bomer, of Magic Mike and Fellow Travellers, is the ‘closest person we can get to perfection’. Does that make the Ultimate Chad, gay? (The Free Press)

• Aspen’s annual Gay Ski Week just wrapped up: “Orlando Bloom leads a conga line of ‘power gays’ while celebrating his 49th birthday.” I want the NYT Style section to do a piece on the scene there. (Page Six)

• Tucker Carlson dedicated a 2.5 hour episode to the gays, titled “Why are you gay?” I watched 20 minutes and had to stop, but it was an entertaining 20 minutes. Living rent-free.

• Sam Altman’s OpenAI is reportedly planning an IPO this year. If that wasn’t keeping him busy enough, he also just announced that he co-founded Merge Labs. OpenAI invested in Merge’s reported $250M seed round. (OpenAI)
  

It’s personal

• Since the last letter, I’ve traveled to Mexico City (Travieso Travieso, Voraz, and Pistilo are my new favorites), twice to New York City, did NYE in Miami, had a colonoscopy, started advsing two AI startups, went to the ER for chest pain (turns out it was likely an anxiety attack and I was being dramatic oops), and put an offer in on a condo...🤞🏼

P.S. I’m starting a Q&A series. Who are 1-2 people I should interview? If you hit reply to this, I’ll see your email.

xx,

JACK RANDALL

Subscribe now

Friend Of is about powerful gays influencing business and culture. Gays have shaped culture, fashion, and media for decades, but recently, we’ve ascended into two other centers of power: technology and government. We’re wealthier and more educated than the general population. And we run fashion houses, tech companies, the Treasury, primetime, and late-night news. That’s worth writing about. The name is a nod to the phrase “Friend of Dorothy,” once used to quietly ask if someone was gay.

Disclaimer: References to individuals do not imply orientation. Don’t come for me; I am lawyered up.

Before I start, I want to sincerely thank everyone for reading, subscribing, and sharing my first letter. I like being behind the scenes, so this felt different for me, but it’s literally just writing a newsletter. It’s not that deep.

It was a big month for the powerful gays and normal gays alike:

• People Magazine named Jonathan Bailey 2025’s Sexiest Man Alive. He deserves the title. The photoshoot is something else. It’s the first time an openly gay person has won. I first googled him after watching him in Fellow Travelers. I’m a bad gay and haven’t seen his other big hits, Bridgerton or Wicked.

• The Netherlands elected its first gay Prime Minister, who is dating a former Olympian field hockey player. People on the internet asked why we can’t have that here, but….

• Our President is busy building a pretty new ballroom and fielding reports about him and Bill “Bubba” Clinton (SNL’s cold open on the matter)

• Barry Weiss, EIC at CBS News and after just selling her elite right-leaning outlet, The Free Press for $150 million, has 6 hot, chiseled bodybuilders flanking her as she moves around Manhattan. Money well spent.

  

• The RealReal’s former CMO shared how they grew the market cap by almost 650%. It was incredible to watch. The pop-up shop on Canal Street was chef’s kiss.

  Our creative team executed this provocative idea of a gorgeous luxury store on Canal St in New York– the mecca of counterfeit luxury goods–with fake purses (submitted to us) that you can’t shop. The intention was to start a conversion about the importance of authenticity and the impact of counterfeit goods on the environment versus resale.

• For a year, I’ve patiently waited for Meadow Lane, a new gourmet grocer in Tribeca, to open. The founder has been documenting the trials and tribulations on TikTok @BrokebackContessa (are you kidding me with that perfect name). They opened last Friday, and it looks gorgeous. I can’t wait to give them my money, but the chicken nuggets need more time in that oven.

It’s personal

• I’ve been a busy bee: consulting for a major VC-firm-that-won’t-be-named-yet, helping friends launch their startups, angel investing, winning a gay Halloween costume contest (I went as a SeaWorld dolphin trainer), visiting NYC before the weather turned, and attending a bunch of media events/launch parties.

xx,

JACK RANDALL

Friend Of is about powerful gays influencing business and culture. Gays have shaped culture, fashion, and media for decades, but recently, we’ve ascended into two other centers of power: technology and government. We’re wealthier and more educated than the general population. And we run fashion houses, tech companies, the Treasury, primetime, and late-night news. That’s worth writing about. The name is a nod to the phrase “Friend of Dorothy,” once used to quietly ask if someone was gay.

Disclaimer: References to individuals do not imply orientation. Don’t come for me; I am lawyered up.

For decades, gays have shaped culture, fashion, and media. But recently, I’ve noticed an ascendance into two other centers of power: technology and government. We run the tech mafia (see Apple, OpenAI). We hold top government posts (see the Treasury Secretary). We anchor primetime news and the NYE Ball Drop. Our dating app’s stock outperforms its straight peers. And in the U.S., gay men are, on average, better educated and wealthier than the general population.

Friend Of is my attempt to highlight this growing influence over business and culture, mixed with my own musings and distractions.

This is not a serious newsletter. I’ll try not to wade into politics. It’s meant to be a light read. An upper, not a downer. I’ll publish letters semi-regularly.

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Let’s begin. Welcome to #1: Who run the world? Gays.

I’m typing my first letter on a Sunday night, in a robe on my couch, popping what must be my 14th Hershey’s Kiss despite being lactose intolerant.

• Apple CEO Tim Cook is looking for his successor. He turns 65 next month. While the company’s market cap has exploded under his tenure, they are getting dragged for Apple Intelligence and bleeding top AI talent to Meta and OpenAI. Bloomberg’s Apple whisperer Mark Gurman says the likely contender is hardware chief John Ternus, who just got a primetime slot at last month’s iPhone Air event. He’s the same age Tim Cook was when he took over from Steve Jobs.

• Grindr Inc. has drama, naturally. Semafor reported (and Grindr later confirmed) that some board members are facing personal financial issues and exploring ways to take the company private.

• Netflix’s new show Boots is an easy, entertaining watch. It’s based on a memoir by a man who enlisted in the U.S. Marine Corps in 1979 when it was illegal to be gay in the U.S. military. Unsurprisingly, the Pentagon’s spokesman called the show ‘woke garbage.’

• A24’s new BDSM romance-comedy film, Pillion (trailer), starring Alexander Skarsgård, officially has my attention. It hits theaters in the U.S. in February and already has a 100% score on Rotten Tomatoes.

• My friend Brian Tran is quietly starting Sector, an invite-only social club for gays. It’s currently focused on building a community in NYC. Members include an Olympian, founders, execs, and members of the media. I’m one of the 100 Founding Members. Read the website and text me if interested.

• IAC owner and media mogul Barry Diller came out in his memoir this summer. I’ve always loved his marriage to powerhouse designer Diane von Furstenberg. From her new interview with Variety:

Legend.

• Charlie Sheen shared in his book and documentary that he hooked up with men, telling 60 Minutes: “Well, there’s a lot of stuff on the other side that I’ve never looked at. And I was like, well, hold on now. And I’m like, well… well, sure. Why the hell not?”

• On Friday, President Trump commuted George Santos. He’s already making birthday Cameo’s for fans. Big win for George, bigger win for Cameo. Worth re-watching clips of his Ziwe interview.

It’s personal

• A year and a half ago, I reunited with Robinhood’s co-founder for his new space and defense startup, Aetherflux. I loved introducing the brand and its mission and working in a new industry. Launching a satellite in space…can take years…and I ended up leaving a few weeks ago after considering where I wanted to spend my time. I’ll share what’s next soon!

• From Boyz to Men: A twenty-something year old ‘surprised’ me with a day trip to wine country recently. After he picked me up, he admitted he hadn’t actually planned anything. My dream of being a passenger princess quickly turned into me calling wineries and restaurants I already knew. We had a good time regardless. Compare that to last week’s text from a man 40+ (I have range). I chose option one, and after dinner, we went to SF’s new cocktail and social club, Ama:

  

• Halloween is around the corner. I expect to see lots of sexy labubus this year.

Disclaimer: References to individuals do not imply orientation. Don’t come for me; I am lawyered up.

Write back with what you liked, hated, want more or less of pls!

xx,

JACK RANDALL