We launched Free Agency Season Three this week and with it are making a few deliberate updates:

• Idea selection: Deepening emphasis on the specialness of idea selection.

• In-person: Eight weeks in our New York office.

• Anti-accelerator: a bias toward slowness in a moment is overly focused on speed.

We started Free Agency as an experiment last year. It has worked really well. It’s led to several of our earliest investments at Terrain. If you care about metrics, there are plenty: acceptance rates on par with elite colleges, applicants from top companies, early companies now raising meaningful follow-on capital, closing enterprise deals, and finding traction faster than we expected.

Those signals are encouraging. But they are not the point. At this stage, they are incomplete. You don’t win a game in the first quarter. The work we care about happens earlier, before any of that is visible.

Free Agency is built around the idea that choosing what to build (and why) is the most important and most under-supported part of starting a company. Rather than optimizing for speed or momentum, the program is designed to create space for reflection, iteration, and honest evaluation. There is plenty of time later to move quickly. This is a period to be more considered, not rushed through with poorly considered vibe prototypes and slop decks.

The name draws from the period in sports when an athlete pauses between seasons to evaluate their options and decide where they have the best chance to succeed. It is a moment defined not by activity, but by judgment.

We’re extending that metaphor into the construct of a residency. Free Agency is an Ideas Residency, a protected period of structured time and space set aside to do the hard thinking that ordinary circumstances won’t allow. Writers take them. Artists take them. They exist because the world optimizes for movement, not for the kind of slow, honest investigation that produces something worth making.

This feels particularly relevant now. As AI continues to lower the cost and increase the speed of building, the relative advantage shifts earlier in the process. Execution is becoming more accessible. Clarity of thought and intention (what to build, for whom, and why it matters) becomes more important, and harder to arrive at.

Most existing programs assume that decision has already been made. They are structured to accelerate what comes next. Free Agency is designed for the period before that commitment.

Season Three runs this summer, over eight weeks, from our office in New York. New York, especially in the summer, provides a uniquely energizing and generative backdrop for this kind of work.

The program centers on close, one-on-one engagement with our team and a small group of advisors. We do not take equity, and there is no demo day. The goal is not to push participants toward starting something quickly, but to help them arrive at a decision they have real conviction in — whether that means moving forward or choosing not to.

Applications are open now. →

Terrain launched roughly two years ago. In that time, we’ve found that being a great partner sometimes means doing things that venture firms of our scale and age don’t often do.

For us, this has taken shape as a sizable body of work alongside our investing work.

We’ve created programs that offer support in idea selection, no-strings-attached. We’ve produced events that bring founders and makers together in ways that don’t follow the standard conference format. We built internal and external tools for founders. We’ve worked with our portfolio companies to produce commercials, video interviews, newspapers, and launch films, with more to come.

None of this was planned as a portfolio service or a marketing strategy. It came from taking the founder partnership seriously enough to act on it. Like the founders we back, we are building Terrain as a company: one where our customer is the founder and our product is a partnership itself. The output has been sourcing, hires, partnerships, and new opportunities we couldn’t have manufactured otherwise.

We’re not satisfied with where this stands today. Our list of what we want to do next is more ambitious and scaled than what we’ve done. There are stories that haven’t been told. Ideas that need to see the light of day. And each new initiative requires more coordination and expertise than the last.

We’re now hiring someone to take ownership of this work.

Not to run events. Not to manage content calendars. But to make ideas happen. The kind of person a film production company or creative studio would call a Producer — someone who holds together complex, high-quality projects, makes good decisions under pressure, and cares about the quality of every output. This is a specific role that we believe many firms like ours will one day employ.

This person probably hasn’t worked at a venture firm, or maybe even in technology. They’ve done meaningful work somewhere, an agency, a brand, a cultural institution, and done it with enough care that the details were never an afterthought.

They see what needs to happen, and they do it. They care what things look like. They push back when something isn’t right.

If this sounds like you, we’d love to meet. Email hiring@terrain.com

I grew up going to Quaker Meeting and went to a Quaker school, and I’ve always found it surprising how little they appear in the American story of commerce, entrepreneurship, and honest hard work, given their contributions.

Reading Will Manidis and Nabeel Qureshi's essay on moral formation versus moral signaling in commerce reminded me of their significance.

Will and Nabeel’s essay traces the Quaker spirit through the English Industrial Revolution, and it surfaces something most economic histories miss. The Quakers didn’t succeed because they were honest and hardworking; plenty of people are honest and hardworking. They succeeded because their honesty was structurally enforced. Community accountability, real consequences for fraud, and constraints that couldn’t be renegotiated the moment they became costly. The results included the introduction of fixed pricing and fair dealing. Economic levers that worked because the people wielding them believed the constraints were received from God rather than chosen for advantage.

As Jony Ive shared of the Quaker’s ethos: “Work as though you are being watched by God and for the good of mankind.”

There’s an American chapter of the same story that deserves telling, because it may be the earliest example of something we’ve taken for granted in Silicon Valley and shows signs of breaking.

In the late 1780s, Moses Brown, a Rhode Island merchant and Quaker convert, became obsessed with a specific technology problem. England had industrialized cotton spinning and made it illegal to export the machinery or even the plans for it. Brown believed that whoever brought that capability to American soil would reshape the economy. He funded a series of attempts to create similar technology with local mechanics, burning capital on conviction long before he had any proof it would pay off. Every single one failed.

Then, in 1789, he found Samuel Slater. Slater was a 21-year-old English apprentice who had memorized the design of a British water frame and had recently emigrated to America with nothing but the plans in his head. Brown brought him to Pawtucket and backed him. He provided the capital, the workspace, the raw materials, and the network of merchants who would take whatever Slater could produce to market. By the early 1790s, they had built what became Slater Mill in Pawtucket, widely regarded as the first successful water-powered cotton mill in America and the seed from which New England’s entire industrial system grew. President Jackson visited the mill 30 years later, recognizing Slater as “father of the American manufactures.” You can still visit the mill today. I took several field trips there as a kid.

Brown was, in the plainest sense, a seed investor — arguably among the first on American soil. He identified a strategic gap, sourced a founder with unique and irreplaceable knowledge, bankrolled repeated failure until the technology worked, and then provided the commercial infrastructure to scale it. The pattern is indistinguishable from what the best early-stage firms do today.

But then, as now, the capital was the easy part. What made it possible was a web of trust and mutual obligation dense enough that two people who barely knew each other could bet their livelihoods on a handshake. Famously, Brown’s entire underwriting process was a letter, an apprenticeship paper, and a conversation in a mid-winter sleigh ride to Pawtucket. The partnership terms he offered gave half the business to a young immigrant whose only collateral was a promise and a memory. Slater reportedly told Brown: if he couldn’t produce yarn as good as England’s, he’d take nothing for his services and throw the whole attempt over the bridge. Brown took him at his word. The contract was already written in something older and more binding — a shared understanding that the work was meaningful, that the constraints were not negotiable, and that the community underwriting the deal would hold both parties accountable through ups and downs. The Quaker method.

This carried forward hundreds of years and, while not directly, underpins the structure that made Silicon Valley work for decades — one I, and countless others, have benefited from directly. Optimistic people taking bets on creativity and ambition, deploying high-risk capital into technology ventures where the investors have little control. That method only functions when the trust is real, and the interconnecting bonds are meaningful.

Lately, there’s a growing sense that those bonds are thinning. Nikunj Kothari wrote about this recently: https://substack.com/home/post/p-186363614

More transactional, weaker loyalties, and in some cases even public fraud and lying from supposed leaders in the market. Funds invest in competitors because they “can’t afford not to.” Co-founders boomerang between hyperfunded startups chasing higher equity packages right when the vesting cliff is reached. Founders do YC angling for an acquihire before they’ve shipped anything.

None of it is necessarily irrational in isolation. But collectively, it hollows out the thing that made the system work in the first place: the belief that the people on the other side of the table meant what they said and would still mean it when conditions changed.

The trust and relationship bond isn’t dead, but it’s scarcer, which makes it more valuable, not less.

The Quakers, who call themselves the Society of Friends, had community and God to drive discipline. Silicon Valley had tight networks and visible reputational accountability. Neither scales to a world of global capital and media. We can’t recreate the structural enforcement that made Moses Brown and Samuel Slater’s handshake last. The void is real.

But some bonds still hold. Like the Society of Friends, they operate on principles and accountability for one’s actions. The work itself is the moral act: make good products with good people, pay fairly, tell the truth even if it costs you. The firms and founders operating this way won’t necessarily outperform in the next cycle. But they’ll outperform over the twenty-year arc where trust compounds while transactional players burn capital on lawyers and optionality.

This requires the same thing it required in Pawtucket. Not virtue as signaling or a moral high ground. But rather a higher calling to act on principle and absorb the cost that comes with it. Those people will find each other, and what they build will outlast the cycles.

As the world inevitably becomes more transactional, I don’t know if this is true, but it’s certainly the game worth playing.

“Be real”

That’s the advice right now. Be authentic. Be human. That’s how you’ll stand out in the age of AI. Founders, VCs, thought leaders, AI company ads — all converging on the same message: authenticity is the answer to AI, to its sameness, to the optimization of everything to a single prompt.

Yes, there is a lack of realness today. We all feel it. But while the world is telling you to be real, how do you actually do it? You can’t pursue it directly. Telling people to just be authentic is like telling a tortoise to speak French.

Realness is an output, not an input. It is not something that someone will produce and put in front of you. It will only come from within, from a light you carry and a proof of what you care about.

Today, as we roll into the Super Bowl, one of America’s last “shared reality” experiences, we’re seeing this play out in real time. Tech marketing is converging on a single message: wrap the product in craft, warmth, and comfort. Shoot on film, use analog audio, show the user’s humanity. “Realness” is framed as the foil against an easy villain: fake, corporate, generated, hollow, even scary.

Two examples, among what I’m sure will be many:

• Website builder Wix has an ad featuring a maker of handmade furniture, the paragon of craft artisans, bathed in warm sunlight, using Wix’s AI tool to build a website. She directs the AI to “give the site more soul.” The obedient machine moves some images around and adds color. The message: with Wix, your humanness isn’t erased, it’s enhanced.

• In similarly warm tones, Anthropic released a series of ads framing other unnamed LLMs as planning to insert ads directly into chat dialog. The personified AI comes across as uncanny and fake: unblinking, awkward, like a character from Pluribus (the recent Apple TV show where humans have surrendered individuality to join a hive mind).

The silicon valley crowd has had a field day with the Anthropic spots. The payoff is meant to be that Claude is more real and human-aligned.

Maybe, but by how much? And to whom? Will Super Bowl viewers come away saying “Claude is the best” or just think “AI is alien and creepy”?

This is the water we’re all swimming in. We are at a moment of seeming peak unreality (and headed higher).

AI enters this picture not as the origin of unreality but the latest entrant in a long line. The last decade gave us infinitely personalized feeds, replica goods indistinguishable from originals, filters making people unrecognizable to themselves, and a wholesale degradation of shared truth. AI makes creation and simulation cheap, social media makes truth plural, inequality makes solidarity thin.

So “realness” returns as a style to bank on. But style is not a substitute for meaning.

And startups are drowning in this.

AI hype plus capital abundance has produced a seeming oversupply of a certain type of founder and company — one built in the right way to be fundable, legible, and video-friendly. Not necessarily a big vision or a necessary problem. Many move like they’re trying to escape some closing door rather than towards something specific. The message “you can just build things” is trumpeted everywhere as a declaration of agency when it feels more like it is pushing people to act for the sake (and ease) of it.

What these companies lack is actual perspective and feeling. It reads like performance, because it is. Pursuing authenticity directly is a trap. Realness, authenticity, aura — these are byproducts of living what you believe. If you don’t already have a sense of what you believe, no amount of trying will produce it. You have to care about something specific first.

The founders I admire have their own ideals and the willingness to commit before they have proof. They aren’t trying to be real. It never comes up. They’re building what they believe in. Authenticity is a side effect.

When we launched Terrain in 2024, we articulated this in Call Your Shot: that the assumptions the startup ecosystem was built on were crumbling, and we needed new answers. Internal conviction over external validation.

This may sound like a uniquely modern phenomenon. But we’ve been here before.

There is no brand more synonymous with selling “realness” through a feeling than Coca-Cola. The product is a “real” formulation of sugar water but the meaning is entirely constructed. Which is exactly what makes them the perfect case study.

In 1969, Coca-Cola launched a now iconic campaign: “It’s the Real Thing.” The goal back then was the same as today: position yourself as authentic when trust is cracking everywhere. Vietnam, the Civil Rights fight, the rise of broadcast TV, a fractured country. In 1971, they paired it with the utopic hilltop ad, “I’d Like to Buy the World a Coke,” casting the beverage as a unifier of a divided world.

It worked, but it was still a marketing construct. As Coke’s brand manager said at the time, it was a direction that “responds to research which shows that young people seek the real, the original and the natural as an escape from phoniness.”

That could have been written today. Realness is what people ask for when belief collapses.

A decade ago, Mad Men used this ad to close out the series. Don Draper, the man forever in search of meaning, meditating on the California coast, having an epiphany cutting to the iconic “It’s the real thing” ad. But he hasn’t had some transformation. He’s just commodifying his earlier trip across America, taking realness and distilling it into an ad for the moment.

This is the trap Draper spent seven seasons caught in. He was able to sell authenticity to everyone except himself. He could manufacture meaning on demand, but never locate his own. Not because he wasn’t talented or even sensitive — he was both. But he never could turn inward. He kept looking for the answer in the next pitch, the next woman, the next reinvention. He had no interior life to draw from, so everything he made was borrowed.

Coke could sell “the real thing” because no one expected a soda to deliver on an existential promise. The distance between the marketing and the product was the whole point. Startups don’t get that distance. At the early stage, the founder is the product. Your investors, your first ten employees, your first hundred customers — they’re all close enough to feel the gap between what you say you believe and what you actually do. The marketing has to be the truth, or it’s nothing.

So if realness can’t be claimed and craft can (and will) be copied, what’s left? The only thing that can’t be replicated: the specific thing you believe and the visible proof that you’re living it. That is real.

It’s hard to find online. The algorithm is powerful. The feed is loud. The onslaught of people telling you what to think, what to build, how to present yourself — it will drown out any signal you have. Many of the people who seem “plugged in” are mouthpieces of the moment, championing the Current Thing, with little sense of what they actually believe. They are like Draper. They don’t have their own principles and can’t help you find yours.

You have to turn inward before you can project outward. This applies to people. It applies to startups.

Here is what I think that requires:

• You need an internal compass. Not a mission statement, not a positioning exercise — a sense of what you care about that doesn’t shift when the discourse or heat shifts. Something specific enough that you can feel when you’re drifting from it. It takes time. It’s developed from a lot of different (and sometimes conflicting) inputs and then tuned on your own beliefs. The work is interior. It happens before you have anything to show for it.

• You need to let your choices prove it. Where you spend your time, how you spend your money, what you say no to — these communicate more than any brand voice or founder narrative. The founders I trust most have a visible consistency between what they say and what they do

• You need to resist performing the process. The temptation is to narrate the journey — the “building in public” reflex, the vulnerability posts, the authenticity signaling. But the real work of developing conviction is slow and boring. It starts humble and personal, not bombastic or cult-like. It builds from simple origins and then earns the audience.

Startups are belief machines. Belief in the real thing before it is there. Early valuations are belief. Early hiring is belief. Early customers are belief. Realness in startups has always been a shared conviction that becomes true because enough people act as if it is — and then follow through to make it so.

You can tell when certain companies and people have it. A small group of people with no distance between themselves and the vision. Driven by hope more than proof. But there is confidence they will get there. They create a collective spirit and soul that others latch onto in spite of facts. Then the “cult” is created.

Before you worry about how you come across, before you think about cutting through: figure out what you actually believe. What you’d still be building if there were no scoreboard. It’s slow, and it’s thankless in the short term. But over time, that becomes magnetic. It brings others along.

That’s how the real thing gets made.

We’re entering a strange inversion point with work, one defined by the rise of polished overabundance, a world where the ability to produce images, videos, and ideas has become nearly frictionless.

Contrast this to most of human history, where the finished object held the value. The painting. The film. The product. What it was mattered. How it was made was someone else’s problem, the craftsman’s, the factory’s, the studio’s.

We will quickly get to a spot where we won’t trust or even register the images/videos/works as special anymore. We will need some other method of verifying the “value.” And while the geopolitical implications of deepfaked world leaders are real, the more useful point here is simpler: when images become untrustworthy, their meaning collapses, and the burden shifts to the maker to demonstrate intent and authenticity.

Try to go back just a few years, before ChatGPT and image models. Back then, a brand pulling off a spectacular, high‑effort visual moment would stop you in your tracks. You would take note. Now, it’s commonplace. Expected, even. You scroll right by.

This dynamic has played out before. Handmade Belgian lace was once so valuable that it was regulated by luxury taxes and regulated like alcohol, smuggled across borders, willed to heirs like jewelry. Then machine looms arrived, and within a generation, lace became decorative trim. The object didn’t change, just the value of its creation.

We’re watching this happen again, just faster and more completely—a deluge of posts, images, and media that quickly blurs into noise. This will continue; like fast food and cable TV before it, you cannot (and should not) fight AI slop. Some will be great and creative and novel and will cut through, but most won’t. Noise will intensify. The algorithm and our attention will decide.

And yet we still yearn for human-scale meaning — a desire that’s clearer when separated from the specific examples that follow, which are better placed in the dedicated examples section below. We still want to feel that tingle of care connecting us to whoever made the thing. I have seen more signs of this recently. Maybe right now, just at the “high-end,” the companies and creative makers who we’ve collectively defined to have “taste” (A24, Stripe, Apple), it would appear that the process is the antidote to this phenomenon. How it was made and by whom matters increasingly. Is there more to the story, to its provenance? Did it show the authors are credible enough to know and care for the details?

Take filmmaking, for example, not as a story about meticulous detail, but as a demonstration of how the process itself becomes the source of meaning. For decades, filmmakers have had access to CGI, green screens, and entire synthetic environments. Yet the work that resonates most deeply tends to come from directors who let the making shape the outcome. A committed process introduces constraints, unpredictability, and texture, all of which accumulate into something the audience can feel, even if they can’t articulate why.

Nearly every great film includes a “making of,” because understanding the process unlocks the emotional charge inside the work: how the film was shot, how actors inhabited their roles, how worlds were constructed or researched into being.

This has bled into the marketing of films: Timothée Chalamet’s recent Zoom meeting for Marty Supreme brought the audience into a meta of the film’s marketing and deliberately toeing the line between genuine behind-the-scenes moment and engineered mememaking, providing provenance to the end result. What made the bit work was the trail of real outputs (a real blimp over CA and TX, a viral jacket) coming from real people, capturing it in the real world. It was messy and a bit sloppy in parts but felt like it was unfolding naturally.

We’re seeing this now in digital production, where brands are making a choice to take the practical, manual way, even if the result is indecipherable to the end audience. Apple TV made a point to do a small amount of design press on the making of their new intro card, pointing out that it is, in fact, real glass. Stripe’s Black Friday website was a physical model city full of wood and glue and, yes, imperfections. Tiny storefronts and street signs. Easter eggs referencing iconic customers. A world in which every building was a nod to someone who uses Stripe. And on the simpler end of the spectrum, Parallel’s recent fundraising announcement was a typewritten letter (on an Olivetti Valentine, no less) on a hand-stamped piece of paper. For a company building primarily for AI agents, the announcement authentically “touched grass.”

Each could have been made by a person with a laptop, in less time and fewer resources. But both create a visible tactile trail of evidence and a world that they’re inviting you into. The world in each is charming precisely because it was made one piece at a time, a series of “unnecessary decisions” to borrow something said by a friend recently, versus one shot via a prompt.

Maybe this is a temporary effect of our transition into a frictionless AI world… like skeuomorphism was for touch displays, or just maybe it’s an early signal that viewers will increasingly value visible evidence that someone, somewhere, cared.

Let people see the labor and your fingerprints. Let the audience see the process and your intent, even if messy. Show that you spent more time than was reasonable. That you chose the longer path, to learn and grow and make with your heart and hand

.

Every maker and founder faces the same unavoidable decision: what to call the thing they’re building. As attention spans shrink and new stories and brands proliferate with increasing speed, getting this right has become both harder and more consequential.

Your name ships first. Before anyone watches your launch video, lands on your website, or tries your product, they encounter your name. Names travel farther than features and last longer than campaigns. They either buy you trust—or burn it—before you’ve even said a word.

I have been working on making this process less chaotic, first by accident and now by design, starting almost a decade ago when I found myself repeatedly helping founders I backed with naming and eventually building Onym, a widely used naming resource.

After working with nearly a hundred startups, teams, and companies (helping create names that have sparked trends like The Browser Company of New York and Modern Life, evocative monikers like Imprint and Keeps, and brand foundations for breakout companies like Base Power), I’ve distilled the work of developing a successful name into something any focused founder can complete in an afternoon. It’s captured in a clear sequence: Orient, explore, distill, validate, commit, execute.

I’m sharing two free-to-use tools as part of our work at Terrain supporting early-stage founders:

• “How to Name Anything in an Afternoon,” a comprehensive step-by-step guide to go from brand definition through naming and selection.

• Untitled.new, an AI tool designed to guide you through a streamlined version of the same creative process.

So block off a few hours. Grab a small group you trust (or run solo). Follow the steps. By the end, you’ll have a better sense of what you’re building and a name to build around.

The act of naming

Before you begin using the guide, or Untitled.new, it’s worth going deeper into what makes a name really work, so you will know it when you see it. What you’re looking for is a hook that sets itself into a person’s mind, linking their brain back to your idea, product, and company. The act of naming has always symbolized the beginning of something: the moment the founder, the artist, the lawmaker, the developer, the parent, arrives at the name is the moment it becomes real.

Despite this almost divine act, the process of naming is usually messy: Gather the team, throw words on a whiteboard, argue, and when the deadline looms, finally settle on “good enough.” Similarly, most naming advice remains stuck in a 2000s-era creativity workshop: cutesy contrived exercises, random walks through dictionaries, and tired ideas of what cutting-edge looks like. The recent explosion of AI-powered “name generators” has only highlighted the problem. These tools promise to solve naming in a single prompt, but they rely on models that have been trained on the same publicly available advice. Their outputs look plausible but lack spark, context, or wit.

While you may get caught up on a perfect name, in reality, the best names are first and foremost appropriate in their form and context. They both situate (where does this thing live in the world, what is its context, its category) and differentiate (what makes it unique, special). They give off a strong sense of who they are serving and the goals they want to achieve.

To achieve this, you need to know who you are—the more concrete you can articulate this, the better. It is easier to name a brand that knows exactly what audience they need to reach via what channels and what success looks like than it is to name a brand that aspires to be an abstract representation of a vision they do not yet fully understand.

What makes a name great

When done right, a great name actively propels a brand further. It compounds over time, growing richer, deeper, and more powerful with each repetition, embedding itself into culture, conversation, and memory. But how do you measure something so intangible? It is admittedly subjective, but I’ve found six dimensions that are the most relevant when evaluating a name:

1. Depth: Does it have layers of meaning? What’s its tone, attitude, and character? Can it carry metaphorical significance without being cumbersome? Does it match your culture and customers’ expectations? Virgin suggests rebellion and rule-breaking; Amazon moved from bookstore to boundless selection, signaling scale and possibility.

2. Temperature: Does it feel warm and inviting or cold and distant? Technical correctness isn’t always optimal; approachability can matter more. Mailchimp feels approachable and human; Blackstone conveys stability and force; Anthropic bucks high-tech convention and opts the Greek word for “human” to convey a sort of high-brow warmth.

3. Voice: How does it sound aloud? Does it flow smoothly or create friction? Zoom sounds crisp and quick; Etsy is playful and cute. OpenAI, coined by Elon Musk, gives a unique mix of regular words and acronyms, creating a memorable rhythm (as a bonus, OpenAI also plays on one of Elon’s favorite naming tricks: contractions (SpaceX = Space Exploration Technologies Corporation).

4. Visual: How does it look on tiny screens or billboard signage? Does it have visual rhythm and balance? Do capitals or lowercase characters change the aesthetic? Slack looks concise and casual; SONOS is an elegant ambigram (readable when viewed from a different direction or perspective). Hewlett-Packard feels cluttered and traditional, but HP renders as fast-moving and tight.

5. Differentiation: Does it clearly stand out from competitors or blend into background noise? Is it viable from a trademark perspective? Amidst countless names like Cloudera or MongoDB, Snowflake immediately stood apart in data infrastructure.

6. Special Wrongness: The special ingredient. This phrase is borrowed from designer Ben Pieratt and author Peter Mendelsund. The concept that a name should have “an unforgettable newness. A new shape. 1+1=3,” and the idea that it can spark a new trend that “in the future, this will be done a lot.” It can manifest in many ways: a slight misspelling, a unique pronunciation, an unexpected word pairing, or an intriguing origin that makes it memorable yet accessible. It is what makes ChatGPT somehow work, why The Browser Company of New York felt fresh, and gives Teenage Engineering its distinctive edge.

Like with anything, some people are better at naming than others. There are professionals and agencies who can help you on that journey, but let’s be clear, there is no magic process. There is just the work. If you do it, especially a lot, I can guarantee you will get great results. But you have to put in the work and volume.

I’ve assembled these two resources to help you in your process. The guide is a thorough method you can use with your team in an afternoon or so to generate candidate names and methods to refine to select the one. Untitled.new speeds up this process further, taking you through a process that is stripped down to the essence of what I have found in both my research and practice. They both provide parameters and guidance to yield great outcomes—chiefly, the right set of names for your company or project.

The long game

Names that hit on most of the above qualities, and carry a touch of offness, become magnetic. They shine just enough to spark imagination, yet remain simple enough to travel the world unburdened. They feel both familiar and surprising, the combination that our brains (and hearts) find irresistible.

When naming your company, I have found it helpful to keep in mind two powerful forces that will pull at you:

1. Ego whispers for something ambitious, clever, impressive; a name that can endure for decades and satisfy your vanity.

2. Logic insists on something clear, direct, sufficient; a name easy to pronounce, remember, and type.

Tesla works because it feels visionary and bold enough to match Elon Musk’s grand ambitions and ties to historical greats (ego), yet remains crisp, clear, and approachable (it has a nice mix of hard and soft sounds; for instance, the -la ending leaves your mouth open) to customers worldwide (logic).

Bear in mind, also, that the name you choose will travel between two audiences:

1. External customers, investors, and the general public who will judge it based on snap decisions in a sea of other brands.

2. Internal team members who will look to it daily for meaning in their work and ways of expanding on your mission.

As you wrestle with these dichotomies, you notice details others overlook: how the name sounds when you’re tired, how it looks in all caps, and whether it translates reasonably. You envision strangers pronouncing it: investors, customers, critics. You test it quietly against futures you can’t yet see.

Great names resonate across registers. They are felt as much as understood—emotional, visual, linguistic, cultural. On the surface, they are plain words, yet they carry hidden machinery, compressing stories and aspirations into something you can fit in your pocket.

And over time, great names deepen. Each repetition lays down another layer. A name gathers meaning the way a river gathers silt, slowly reshaping the landscape around it. Nike means victory not only by definition but by decades of triumph. Google came to mean search because of the company’s relentless investment in it (from their colorful logo to their geeky demonym: Googlers). Amazon was once puzzling; now it connects as everything, A to Z.

You don’t need the perfect name. Perfect names don’t exist, only names that work for what you’re building, for who you’re serving, and for how boldly you stand behind them. You need one you’ll use with conviction. The compounding of consistency and time will do the rest.

You can get the full “How to Name Anything in an Afternoon” guide and try Untitled for free.

Base Power Company just announced $1BN in new funding and the opening of Base Factory 1. Base was our very first investment at Terrain, and we’ve invested four more times since.

Working closely with the team has shaped how we think about execution.

There’s a quality to how they move: fast, focused, and relentlessly learning, that we call Base Pace.

We wrote about it here, and how you can bring the same energy to your own work.

Base Pace

Two years ago, Justin Lopas and Zach Dell founded Base Power. In the summer heat, they started knocking on doors, hauling batteries up driveways, and convincing homeowners to let an unknown startup install power systems in their homes. In just the last month, Base installed over 20 MWh across 3 markets, opened a Next‑Gen factory in Austin, Texas, and raised $1B to advance their mission.

Base was our first investment at Terrain. Since then, we’ve worked both as investors and close partners. What we’ve seen up close is a natural rhythm born of ownership, constant learning, and a distinctive pride in work that we now refer to as Base Pace.

Base Pace is not performative speed or “locking in,” it is a constant baseline. Organizations with high Base Pace learn faster and accomplish more. Here’s how to achieve it:

1. Start with the end state

At Terrain, we work with founders who call their shot. They start by asking: when all is said and done, what should the world look like? Base’s answer is foundational for America’s future: abundant energy for all.

When talent can choose between seven-figure packages or putting humans on Mars, your mission has to matter. Base’s end state is ambitious enough to attract the best, tangible enough to explain at the Thanksgiving table, and specific enough to guide daily choices. It’s lived every day, not filed away. A north star that stays fixed while tactics evolve.

2. Break the end state into ambitious parallel paths

Base deconstructed this vision into three equally important tracks: residential energy, grid-scale solutions, and regulatory transformation; each owned by a leader who could found a company. Alumni of SpaceX, Tesla, Starlink, and Anduril run their domains like parallel ventures aimed at one finish line.

3. Ship the smallest unit of progress possible

Inspired by SpaceX’s cadence, Base focused on the smallest atomic units of learning, for each path: one installation, one conversation, one kWh traded. They refused to let planning theater or perfecting slide decks delay field time.

Early on they installed systems one by one, learning through hardware misses and regulatory friction. When a major storm opened Houston, they launched quickly while others would have waited for “readiness.” They shipped to learn, not to look perfect.

The results are that while similar companies would likely just be launching their first product, Base is already on Gen 3, incorperating all of their learnings along the way.

4. Leaders set strategy and get in the weeds

Fast organizations preserve information fidelity top to bottom. Leaders reviewed site surveys, sold door‑to‑door, drove trucks, and installed hardware. The people deciding what to do also touched how it actually worked—so context stayed warm and decisions sharp.

The early team worked from a converted house that doubled as an install site and lab. It was scrappy, the lights sometimes flickered, but it kept everyone close to the ground. Hands-on work builds intuition: servicing customer needs, wiring systems, and working alongside crews.

Stay in the weeds as long as it meaningfully improves the quality of your bets, and the quality of delegation with intact context.

5. Create organizational pressure through parallel execution

When multiple teams build toward one end state, no one wants to be the bottleneck. Base made the pressure visible: a small turtle figurine sits with the team most likely to slow the chain. Everyone sees it. Everyone knows why. It’s lightweight and memorable accountability.

Each function feels the others’ pull. Sales can’t overpromise what operations can’t deploy. Operations can’t deploy what supply hasn’t secured. Trading can’t optimize what isn’t installed.

That tension drives outcomes. Marketing, where Willem has worked closely over the last year, shipped campaigns that teams 10x the size struggle to match. In parallel, regulatory turned compliance into an advantage; Texas retail energy licensing became a moat through speed.

The compound effect

Roughly two years ago, Base was notes and spreadsheets. Today, they’ve put 100+ MWh into the ground, passed meaningful state legislation, built U.S. manufacturing capacity, established utility relationships, and created a brand competitors struggle to match.

Fast companies attract fast people. When your organization learns in weeks what others learn in years, the highest performers want in. And when you’re running next to top performers, you naturally pick up the pace. Ultimately, in markets with constant change, a culture of learning faster than everyone else is a durable advantage.

A challenge to the next generation

Every ambitious founder should study Base. Not to mimic tactics, your atomic unit of progress will differ, but to challenge the conventional wisdom of how long things “should” take.

Base is proving this is possible. They’ve shown that a two-year-old company can shape markets, influence policy, and compress cycles from years to weeks—not by moving fast and breaking things, but by learning and building at Base Pace.

—

View the entire newspaper and the JOIN THE CHARGE announcement at BaseAmerican.com.

In addition to this essay, I met up with CEO Zach Dell to visit Base Factory 1 and discuss the company’s upcoming plans, hiring, and culture.

We just launched Season Two of Free Agency, Terrain’s program to select your startup idea, before founding or funding.

Applications are open until September 14 at terrain.com/freeagency.

Why Free Agency?

When you're thinking about starting a company, you have unprecedented leverage and choice. You're a free agent, unencumbered, with infinite possibilities. But it's also one of the highest-stakes decisions you'll ever make.

Here's what usually happens: The moment you signal you want to start something, the machine kicks in. Investors slide into your DMs. Friends ask what you're doing. Former colleagues want to join. Momentum starts whether you're ready or not.

Most programs feed this. EIRs, accelerators, and incubators can be great, but they put you on their timeline, give you their playbook, and push you towards set terms and frenzied demo days.

What we do is different.

Free Agency is the space before starting. To push you to start for the right reason. 8 weeks, we take no equity, no strings attached. Just you, us, and the question that matters most: What should you build?

We launched Season One in February, as an experiment, and worked with 8 free agents. Of those:

> 5 raised capital
> 2 decided not to start a company
> 1 is bootstrapping

We consider each of these outcomes a success. In each, they reached personal clarity and an outcome that was right for them.

Free Agency starts with you. Your roots. What energizes you. The problems you can't stop thinking about. Then we help you get going, with access to customers, products, and resources to build.

• 1:1 partnership with experienced investors and founders to navigate the idea maze.

• Collaboration on core methods dedicated to surface and select the right idea.

• $350k+ in tech credits from Microsoft, OpenAI, Anthropic, Framer, and more, along with other benefits, including early access to new technologies and go-to-market support.

• Access to specialists, customers, and CEO advisors.

At the end of the program, you’ll reach one of two outcomes: (1) A high-conviction startup with early momentum, or (2) A clear realization that now isn’t the right time, and that’s a win, too.

Free Agency gives you the space, structure, and support to make the right decision. On your terms.

Applications close September 14, and Free Agency starts shortly after. To learn more about what to expect, watch our explainer video here:

Three weeks into my first foundations class at the Rhode Island School of Design (RISD), I pulled my first all-nighter. Wrestling with clay, I was convinced I was making something profound. Then came the critique.

Peers and professors dissected every poorly considered curve, every spot where I'd tried hiding incompetence with excess material. They tore my work apart. But that friction, the confrontation with my limitations, carved something permanent into me.

For years, I learned this way: Attempt, fail, dissect, try again. In Color Theory, mixing a hundred shades between two hues. In Typography, I spent hours kerning a series of words until their rhythm felt just right. These weren't arbitrary exercises; they etched precise grooves in my perception. It was specific and cumulative. Friction eroded poor execution and clumsy ideas until something simpler and more elegant was revealed.

Trial, error, filling skill gaps, honing hand and eye: it was reinforcement learning built through thousands of small decisions I'd been forced to defend or abandon. I carried this mindset to my design work at Apple, Google Maps, and later my own startup, Oyster.

But friction, once an indispensable process of building competency and perspective, is vanishing to AI. A single prompt generates polished landing pages, completes brand systems, and ships working applications. The fruit that once required long, arduous labor now drops directly into our laps, ripe yet uncannily hollow.

Automation threatens millions of jobs, but beyond near-term economic pain is a deeper concern. Entry-level roles stand to be disproportionately affected—the places where, for generations, people went to accumulate experience and learn their craft. Knowledge risks becoming merely transactional, a commodity to be accessed, rather than relational or internalized. Information on tap instead of an ongoing dialogue with ourselves and the world. We should use automation to take away mundane obstacles and drudgery. I do. But we must recognize the distinction between that and what I call productive friction. This is the kind of difficulty that’s worth preserving, the kind of struggle that pushes you forward as you push against it.

The trick is in knowing what to look for.

Productive friction has three main principles:

1. Immediate feedback: You understand when you've failed and can see why.

2. Cumulative learning: Each attempt builds your reference library.

3. Transferable principles: The specific teaches the general.

This manifests differently in different fields. But it’s universal. It’s also the foundation of building taste. Taste is often held up as an irreducibly human thing, the saving grace of our uniqueness in the AI age. But taste isn’t something anyone is born with or even a deterministic goal. The focus placed on it mistakes the output for the input. And when you ask what people mean by taste, typically they’ll stumble around for a bit before landing on something like “you know it when you see it,” or list off some nice-looking design features that have been sold to them as “craft.”

Taste isn’t any one thing. It is your thing. And it’s a product of friction.

Taste is an accumulated ability, earned through making and repeated discernment. It cannot be shortcut or passively consumed. It can only bloom through practice, care, and cumulative experience. Friction isn't inefficiency to be eliminated. It's the resistance necessary to build genuine judgment and refine taste. Its value doesn't lie in the final product but in the work itself. AI allows production without labor, creating the illusion of progress while sidestepping much of the actual learning.

AI might push toward immediate legibility or conventions, but taste—my own, for instance, shaped by American sportswear, early internet aesthetics, graphic design history, and specific cultural elements from New York City and New England—is an accumulation earned only through repeated struggle in unforgiving studios, offices, and workshops. Friction, in other words.

It works in subtle, but discernible, ways.

The path of more resistance

Friction forces articulation. In those RISD critiques, “I just liked it better” meant blank stares and humiliation. I learned to identify and name what I was seeing: the way warm gray advances while cool gray recedes, how a curve that accelerates too quickly feels anxious and disjoint.

It builds pattern libraries. After hand-kerning enough headlines, researching enough papers, you internalize rhythms. After mixing enough chemicals, you predict how they will interact. This allows you to remix and build on a strong foundation.

Friction also develops conviction through contestation. When peers attacked my composition, defending successful elements while acknowledging weak points taught me to distinguish personal preference from universal principles. This conviction becomes a position you can articulate clearly beyond “I like it.”

This phenomenon isn’t exclusive to design. A chef adjusts seasoning instinctively because they've oversalted dishes thousands of times. Carpenters anticipate how walnut splits because they've felt it crack beneath their chisels. Mechanics hear subtle engine faults after years of troubleshooting rattles.

Automation streamlines tasks but inhibits mastery. Junior developers who only lean on AI may struggle to debug from first principles; writers who exclusively prompt can’t structure an original argument. They become adept at generating outputs, but become disconnected from foundational insights.

The solution isn't to abandon AI but to be intentional about where friction remains and matters. In my own work, I am constantly using AI (as much as possible); it would be stubborn and short-sighted not to. But like any tool or collaborator, it requires thoughtful restraint and careful judgment of when to engage.

Before starting a project, I clarify what kind of answer I actually need. AI can instantly deliver plausible solutions, but are those solutions meaningful, or just comfortably convincing? When approaching design, I first sketch by hand to avoid tool-driven thinking, and ensure simplicity and clarity from the start. With branding projects, I intentionally let ideas simmer, accumulating influences through serendipitous wandering rather than rushing to resolution. When writing, I commit to an initial full draft—raw and messy if necessary—before seeking AI-assisted refinements. Most critically, when learning something new, I go straight to primary sources rather than settling for summaries or shortcuts.

This intentional friction keeps my thinking sharp and ensures that when I do engage with automation, I do so from a place of genuine understanding and deliberate choice.

The proof-of-work world

How do we recognize genuine expertise now? For generations, we’ve looked to credentials, like degrees attained and company names on resumes. Increasingly, the proof is in the outputs: visible friction, evidence of struggle, and personal investment made tangible.

Today, it's harder for many to find a first job, yet never easier to create your first opportunity. Human labor is shifting toward adept humans leveraging AI to accomplish vastly more. In this emerging world, proof of work replaces credentials and titles. What matters is what you've made or shipped, not what degrees you have or where you got them. A teenager building their own thriving app; a Shopify intern candidate proactively pitching themselves; a student provocatively challenging university administrators. This is friction made manifest. Knowledge gained from this kind of experience cannot be prompted into existence; it must be earned.

How do you do this work? Simple: Do it. Try lots of things, fast. Bring people along with what you are doing. Instead of trying to climb some arbitrary career ladder, consider following experiments and ideas that draw you in. Every hour spent wrestling with software, every failed print run, every brutal critique creates part of a foundation that you’ll later need to place bigger bets and call bolder shots.

The choice

The world divides in two. On one side: utility, stripped of mystery, measured in speed, cost, and precision. Frictionless. On the other: meaning, full of ambiguity, judged by story, risk, and personal intent. AI is conquering the first. It should. Let it drive the bus, draft the forms, color-correct the photo, and sand some of the rougher edges. Then you can focus on what matters. Preserve friction where it counts, not as nostalgia or high-minded purism, but as method and meaning. This approach will better prepare us to work successfully in the AI age. Offload the boring. Keep the stakes.

Years later, I finally understood my professor’s lesson. The point wasn't to produce flawless art; it was to develop the judgment that can only come from having your hands in the material and experiencing intentional struggle.

That failed clay sculpture? I kept it. In a world rushing to remove the struggle, it reminds me that friction was never the enemy. It was always the teacher.

Historically, I have found that hiring for first designers is a bit more idiosyncratic than building out an engineering team or a first business hire. Oftentimes, founders' networks intersect less with designers and even if they have an appreciation and eye for design, founders often have a more cursory view of what makes a designer successful in an early-stage company. It can result in frustrating and slow processes.

I’ve helped dozens of companies hire their first designers but never documented a process. Two of our early-stage portfolio companies at Terrain are now hiring founding designers, and this caused me to reflect on what founders should look for and how they could find the best designer for their stage and needs.

This is meant as a guide to help any early-stage founder find some solid ground when scoping their first design hire. This isn’t a how-to-hire or a when-to-hire guide; those are important but different topics.

What follows is a profile on what to look for in a great first designer and how to best attract them to your company.

And if the following designer sounds like you, I’ve put a bit on two opportunities hiring below; feel free to reach out.

—

Despite good intentions, most startups approach their first design hire all wrong.

This isn’t their fault. They are fed many big ideas about design quality. They learn about design from a very limited set of sources and leaders. They look at these companies known for “good design” and see polished landing pages & products, robust design systems, high-end brand campaigns, and specialist after specialist in their ranks. They often conflate PMF, budget, visual decoration, and actual good design. I don’t want to name names, but just think about a few examples you know.

And when the time comes to hire. I’ve heard the same refrain again and again…

“Our freelancer is maxxed out and design is a bottleneck, so we’re looking to hire.”

“We paid a designer to make a design system/brand and need someone to apply it across materials.”

“We really value design and want someone from [insert hot, tasteful company of the moment.]”

“I really like Jony Ive.”

These searches often begin from scarcity, 3 weeks after you needed it. They are overly focused on pixel-perfect portfolios and impressive backgrounds. This isn’t how you create the template for an ideal teammate. Early-stage companies need something fundamentally different than what large enterprises or famous freelancers provide.

When searching, founders should start by flipping the orientation away from these qualities and instead focus on their company and needs. How do you specifically answer the question “Why you?” — what are the uniquely compelling aspects to your company that no one else can provide, and what do you really need from the role?

From there, you can get started. The best designers for startups consistently demonstrate range and pace—qualities essential for getting things off the ground and installing a design culture. So, what exactly are range and pace, and how do you identify them?

Range & Pace

Range is a flexibility with tools, surface areas, outputs, and knowing which to lean on and when. The ability to change altitude from details to the bigger picture—scrutinizing an animation's timing one moment, then articulating how the product roadmap affects investor perception the next. This isn’t a generalist; it is someone with discernible skills and is capable of both business reasoning and tactical design execution.

Signs of genuine range:

• Skill and obsession in their lane, but vision for the entire business. They ask insightful questions about customer acquisition costs, engineering tradeoffs, support loads, and onboarding emails. They proactively define foundational elements, like your first design system, and anticipate future needs that may affect other parts of the company. They understand design extends beyond the primary product flow and can articulate stories incorporating the whole picture.

• Opinionated on outcomes, flexible on solutions. They hold strong views on quality and taste but readily adapt when presented with new perspectives. They admire and learn from other business functions—sales, markets, engineering, customer service—seeing all of these as essential design inputs. They have the humility to pass responsibilities to someone better suited when appropriate. Startups resemble basketball teams: everyone is on the court together, and knowing precisely when to pass, when to shoot, is how you win as a cohesive team.

• Willingness to do what it takes. This is a big one for me, personally. They need to be able to get dirty and do work that others may see as “below” them. This doesn’t mean they will only be doing this type of work, but they will step up where it counts: speaking to users, building testing frameworks, learning to read the data, understanding what economic limitations may apply, and questioning deep-seated ideas or philosophies.

Pace is speed of design execution, a comfort with shipping quickly before perfection, and an ownership of the outcome. Pace doesn't necessarily mean grinding nights and weekends. Great designers who move quickly aren't frantic—they're even-keeled, efficient, and intentional. They know when polish is essential and when rough edges are perfectly fine.

You'll recognize real pace when you see:

• They ship, consistently. Their actions demonstrate short feedback loops and getting things done. Ideas move from sketches to prototypes to user reactions in days—not weeks. If something is out of their skill set they ask for help or learn it and keep moving.

• Always on-top of new tools and ideas. This doesn't mean being religious about tool optimization or trend-following but they need to have a finger on the pulse of what is happening in design. They actively explore new ideas, have opinions on favorites and dislikes, adopting and discarding rapidly. They pour over new concepts because they're excited about them, not because anyone is telling them they have to. They're never stuck using outdated workflows or styles for the sake of it.

• Obsession with outcomes, not outputs. They'd rather ship something imperfect today than something flawless next month if it means faster insight. They do not reinvent the wheel or get hung up on decoration, they want to see things improve for the product, not their portfolio.

Together, these qualities create the organization's breathwork—expand wide to imagine the grand structure; contract fast to lay the next brick. Outside of founders, designers are some of the best positioned to provide this and over time that inhale-exhale becomes the pulse of the product.

Spotting "Range & Pace" in action

These are not qualities that show up consistently in specific companies or alumni. It is certainly not about titles or seniority. But there are signs:

• They have a portfolio (if not a site, they share work online or have live projects) filled with their own experiments, side projects, and shipped MVPs—not just attractive, conceptual screens or exhaustive case studies and sticky notes.

• They can flex top-tier quality (or potential) in a few ways, be it visual design, brand, motion, prototyping, code. They need to have a few clear spikes that they are quick at to pair with a broader set of abilities.

• They're responsive, proactive communicators throughout the hiring process and show a willingness to create their own momentum.

• You never catch yourself making excuses for them because they're “hot talent.” Their hiring behavior matches exactly how they'll act on day 30.

• They are a calming force, welcoming faster cycles rather than panicking or pushing back because of those constraints.

Lastly, on one of the oldest demands for modern design: “Should designers code?” I reframe the ask: I think a designer needs mastery over their medium. Increasingly, yes, this can mean code, but it can also manifest in other ways… Maybe they have an ability to design something so perfectly brilliant that they cause engineering partners to move 10x faster, or they offer tremendous value to marketing, that works just as well. Again, it is about the right outcome, not the specific output.

The “Why you?”

This is where things get specific. Finding a designer with range and pace is one thing, identifying why they should join your company is another. Even if you just raised a hot, oversubscribed round, and are growing like a weed, this is a good exercise. Designers are in demand like never before and there are shockingly few who really fit the “first designer” archetype.

Make two lists to give focus to your search. Clearly define:

1. What your company specifically needs in design: brand identity, product interfaces, onboarding, etc.

2. What makes your role uniquely appealing: cutting-edge tech, special customer base, and creative freedom.

This clarity will make it easier to recognize what actually matters and how to get it.

Building a design culture that sustains

The best way to attract a great designer is to create a culture that already values design. This does not happen overnight and, like most things in a startup, starts with you, the founder. Some notes on how to cultivate a thriving environment:

• Design literacy starts at the top. You don't need to move pixels yourself, but you must learn what good design looks like and why it matters. (read terrain.com/design-literacy for more on this.)

• Define your north star for quality. Without clear direction, pace becomes chaos. Give your designer a clear vision and sense of what matters most, then trust their judgment on how to get there.

• Give autonomy with clear, specific feedback. Step back and trust their expertise. Great designers thrive with autonomy and adequate heads-down time. When you come in with feedback, learn how to deliver it — understand the right fidelity and know what matters when (don’t let a button color get in the way of seeing the product thinking).

• Make reasonable expectations. You wouldn't ask one front-end engineer to handle your entire stack. Likewise, don't expect one designer to do all visual design, research, animation, and branding indefinitely.

• Occasionally, let them have time to pursue bold, unconventional ideas. It keeps creativity alive and freshness flowing.

Early-stage design isn't shipping the perfect screen or hype video; it's training a muscle to accelerate your team's overall rate of learning and assembly. Hire deliberately for range and pace, nurture a culture where design is more than aesthetics, and watch the whole org shift into a higher gear.

The right first designer won’t just make beautiful work, they will put oxygen into the system.

—

If you are a designer reading this and want to make this actionable, here are two first designer opportunities for the right individual with range and pace:

Systems Product Designer – Seed-stage (stealth)

• Build the rails & ecosystem that enables makers to earn real money on day one.

• Experience and excitement to own a marketplace, rewards, payouts, and ecosystem experience.

Mobile Product Designer – Seed-stage (stealth)

• Bring workflows formerly reserved for power users and desktop software to mobile.

• Passion for making a code editor and brand that feels like magic.

Both roles are in-person in SF and come with strong comp and equity packages. Each company is highly ambitious and led by experienced founding teams. No arbitrary tenure or pedigree requirements—only clear evidence of range and pace in your work.

DM or email me willem@terrain.com if either sounds right for you.

—

Thanks to Frank Guzzone, Carly Ayres, Kevin Twohy, Cameron Koczon, Duncan Fraser, and Brandon Jacoby for reading earlier drafts of this essay.

“Agency” is the kind of word that, right now, floats thickly across the web — one of those sticky buzzwords the cynical love to hate but secretly recognize as necessary. It's a bit like “taste”: precise enough to examine closely yet vague enough to become a catch-all. Why the appeal? Probably because while intelligence is becoming as mundane and effortless as a keystroke agency stubbornly clings to our human heart, reminding us we're still choosing, still acting, still (mostly) not robots.

There is one week left to apply for Free Agency (you can apply here), and this impending deadline has kicked off some reflection on how agency manifests in individuals.

Agency, I've found, expands through doing. It's cumulative: action breeds more action, and suddenly a hesitant doer transforms into someone natively agentic. Those who've had a restlessness of agency since childhood — often seen in obsessive hobbies, early passions, or late-night tinkering on tools and toys — rarely lose it. But the corporate world tends to try and tamp down agency, and thus sometimes it whispers rather than shouts, especially at the start of something new — a company, a project, a timid idea barely breathed aloud.

To pin some of these ideas down, I’ve been collecting notes on these agentic actions and mindsets. I've arranged them into a chart, simple and clear, like one of those tidy diagrams you'd see at the top of a trailhead outlining the guidelines of the park. 

And if you find yourself admiring the aesthetic, it nods (humbly) toward another set of principles: those drafted for the Sea Ranch community.

A 90-day program from Terrain to help you select the right startup idea—before founding.

No equity required. No capital to accept. No demo days. No strings attached. Just the freedom to find what's truly worth building.

How it works:

Terrain provides 1:1 support, $350k+ in resources, access to CEO advisors & specialists to uncover your idea. Like in pro sports, this is your moment to explore options with intention. We'll help you strip away the noise and find clarity ahead of committing.

We will work with a select number of ambitious individuals from any field seeking to build their next great work. You don't need a fully formed idea—just unique insights & the courage to make something wonderful. Let’s find what's worth your energy and focus.

Why are we doing this?

Founding has shifted from creative inspiration to a career rung. For many, it's easier to raise capital than decide what to work on. VCs flood DMs with offers even if your idea leads nowhere. But this is wrong. What you work on matters.

Most accelerators strip you of agency. At worst, making you a surrogate for their idea. At best, manufacturing momentum for a quick markup. Agency isn't given. It's created. You can't outsource it. You have to think for yourself.

The reality is, startups are hard. The path is ambiguous, uncharted. We believe facing this early will steel you for what's to come. If you do this right, others will follow. But first, you must prove to yourself it's worth doing at all.

Free Agency isn't about competing with others—it's about pursuing your own greatness. The truly exceptional aren't satisfied with following tracks; they forge their own.

If this resonates, I invite you to declare your free agency and apply for our inaugural season by March 25 via the link below. Let’s build something worthy of you.

terrain.com/free-agency

Imagine a tree. A great, sprawling fruit tree, its branches weighing heavy. Each fruit is a possibility, an option, a future you might one day grab. The tree is vast, its bounty endless. You stand beneath it, gazing up at the broad canopy, thinking: I am free. I am limitless.

But here’s the catch: the fruit is rotting.

Not all at once, not in a dramatic collapse, but slowly, quietly, almost imperceptibly. The options are still there, still dangling, but they’re softening, browning, losing their vitality. The illusion remains until you reach up and realize the fruit is already past its prime.

This is option rot, the slow decay of potential that comes when we refuse to choose. When we refuse to pluck the fruit.

Nick Saban, that sage of Alabama football, once said something so simple it takes a second to realize the revelation:

“These guys, they all think they have this illusion of choice. Like I can do whatever I want to do. You have a younger generation now that doesn’t always get told no. They don’t get told this is exactly how you need to do it. So they have this illusion that they have all these choices. But the fact of the matter is, if you want to be good you don’t really have a lot of choices. It takes what it takes. You have to do what you have to do to be successful. You have to make the choices and decisions to have the discipline and the focus to the process of what you need to do to accomplish your goals.”

At first glance, it sounds like the kind of thing your father might mutter while tightening a bolt on the lawnmower. But Saban isn’t just talking about football players. He’s talking about life. How excellence has a price. About how greatness doesn’t slip away in a single moment, but erodes over time. Because we refuse to commit. Because we refuse to close doors.

How we love our doors.

Our culture has become an endless hallway of doorways, each one leading to some idealized, hypothetical future.

Remote work means you can live anywhere, so why plant roots?

Streaming services offer endless entertainment, so why bother making friends?

Doordash delivers everything to your doorstep, so why get out into your community?

Dating apps mean you can swipe forever, so why choose one?

Even children—the ultimate commitment—are deferred indefinitely, because, well, none of my peers are doing it either.

This is the optionality trap. It whispers to us in the voice of reason: Keep your options open. Stay flexible. The world is changing too fast to commit. And so we float. We dabble. We optimize for a future that never arrives.

The internet’s voyeuristic lens has amplified this optionality mindset. We can peek into countless different lives and paths, living vicariously through them; all seemingly perfect and possibly within reach but never achieved. Echoes of “I could do that if I wanted to” ring in your head.

But here’s the thing: this is a mirage. Optionality promises freedom but delivers paralysis. It offers endless paths but leaves us stranded at the crossroads. The more doors we leave open, the less we walk through any of them. And slowly, imperceptibly, those doors close and the options begin to rot.

The Generalist’s Lament

This paralysis of choice goes beyond the personal. It has a hold on entire industries and career paths. Nowhere is this optionality more visible than in the tech industry.

Software has been historically expensive and difficult to build, and few people have had the skills to do it (according to one measure, 0.5% of the world’s population knows how to code). Engineers and designers could therefore apply their skills to any number of problems, no experience necessary. But this flexibility, while appearing advantageous, often becomes a trap. It has become common for someone to move between categories and markets fluidly throughout their career; from consumer to fintech to healthcare to crypto to AI, all within a single decade. Chase the hot thing. What would have once been seen as an erratic, or even impossible, career path a generation ago has become the norm.

This is the optionality mindset in action: the belief that the future belongs to the generalist, the jack-of-all-trades, the eternal dabbler. But it’s a lie. The future doesn’t belong to the generalist. It belongs to the obsessed.

Take Palmer Luckey. Luckey didn’t succeed because he kept his options open. He succeeded because he committed, fully, recklessly, absurdly to a single vision. He didn’t dabble in VR. He became VR. And then, for the next act, he became American Dynamism.

Or Patrick Collison and his brother, John, who launched Stripe when payment processing was considered boring infrastructure. While their peers chased consumer apps, the Collisons committed to solving the unsexy problem of online payments. They didn’t dabble in fintech. They became fintech.

Or consider Bryan Johnson and Blueprint. His body is his company. Is he a bit ridiculous? Yes. But what groundbreaking person isn’t? He has hard-committed to his thing. And if he is right, soon many others will follow.

And now? You don’t want to compete with these founders on their turf. Because when you commit to something with that level of intensity and obsession, you become unstoppable.

The Courage to Close Doors

The best things in life: love, skill, interest, compound over time. But they only compound if you let them. If you commit. As you go deeper, you build your competence, your insight, your network, and your confidence in the decisions you make. You get to play your own game.

This isn’t to say that exploration is worthless. As a child, as a student, as a human being, you should dabble. You should wander. You should sample everything life has to offer. But at some point, you have to pick a piece of fruit. You have to grab it and dig in.

The difference between those who succeed and those who stagnate isn’t access to options; it’s the willingness to exercise agency over them. To say: “This matters enough that I’m willing to let other things go.” While the world obsesses over accumulating options, the impactful are busy eliminating them, channeling their finite energy toward the few things that compound over time.

So ask yourself: What are you obsessed with? What door are you afraid to close? And what might happen if you did?

Optionality is a product of fear. And the only way to beat fear is to face it. To walk through the door and close it behind you.

And while others allow their options to rot on the vine, the focused few pluck that fruit at its ripest.

Between 1920 and 2020, humanity did something unprecedented: we made a world almost entirely for ourselves. Not for gods, not for kings, but for the individual human being.

In these hundred years, we birthed mass culture and it became our shared nervous system. Everything from Elvis’s hips, Sputnik’s launch, and the Friends theme song stitched together a global identity. And for the first time, we archived not just the extraordinary but the mundane: countless laughs, smudges, and offhand remarks. The 20th century turned humanity’s ephemeral noise into a cathedral of data, one that would become the foundation for artificial minds..

It was also a fleeting time, we realize now—a century where we wielded the power of mass creation without the support of artificial minds. Like all great transitions in human history—from oral traditions to written word, from scriptorium to printing press—this shift marks both an ending and a beginning.

Cultural memory has a certain rhythm: every generation romanticizes the era roughly 30 years before its own. Gen Z clings to the pixelated naivete of the 2000s; millennials buff the 1980s and 90s into a yuppie golden age; Gen X yearned for the 1960s idealism. But the 2020s mark a rupture in this continuum. When an AI-generated song hit the Billboard charts in 2023, the prior century collapsed into legend: the last time creativity wasn’t a dialogue with silicon.

Future generations, my own kids included, will be raised in a culture where every song, building, and political system is co-authored by machines. They will look back on this era with wonder and nostalgia: a mythic age when creation was raw, imperfect, fragile, and ours alone.

Consider Apollo 11 moon landing, an apex moment of the 20th century. The Apollo computer ran on 2MHz of processing power (an electric toothbrush has more), schematics drafted in pencil, mission control in a haze of cigarette smoke, astronauts training in swimming pools. Future humans will marvel not at the triumph, but at the audacity: They did this with slide rules and human spirit.

What made it mythic wasn’t the output, but the constraints. We awkwardly and inefficiently built atop the work of other humans, not synthetic minds. The Ford assembly line wasn’t designed by algorithm; Pixar’s Toy Story wasn’t a latent diffusion of a simple prompt. Apple was born in a garage by misfits, not from some rigorous analysis. Even our failures—the Edsel, Google Glass, Fyre Festival, the Juicero—were authentically ours. You can feel the humanity: vision, overreach, ego, lack of precision—the trembling hand of a species not fully optimized.

Then came the pivot point. As pandemic lockdowns accelerated our migration to digital symbiosis, something else awakened alongside us. OpenAI released GPT-3 to little public acclaim, but it marked a threshold we couldn’t uncross. Shortly thereafter came DALL-E 2 and Midjourney. Suddenly, anyone could type “a fox in a spacesuit, oil painting” and conjure it. The shock wasn’t just the output; it was how swiftly it felt normal.

Henceforth, every painting, pickup line, and thought piece (even this one!) carries a silent question: Was this you, or the machine?

The results aren’t perfect yet, but like the first steam engine or the typewriter, they hint at a world where creation requires less work. Less staring at blank pages. Less wandering. Less doubt.

By 2030, the cultural pendulum will have fully swung this way. A child will instantly generate a film that Kubrick might’ve made, or a dozen sequels to Grand Theft Auto. But future critics will likely note a telltale smoothness in post-2020s art—and originality will require new depths. We’ll have to go further to find our rough edges, our in-jokes, our fingerprints. The Warhol of 2070, raised on infinitely customizable and scalable AI, will marvel at how the original Warhol worked: cutting film by hand in a filthy loft, drinking Campbell’s Soup straight from the can, turning literal trash into something sacred.

The longing for this bygone era will grow exponentially. We’ll become their Roman Empire—a civilization whose artifacts speak of both triumph and limitation. Future humans will understand our art through AI-powered analysis, algorithms dissecting every petrified scroll and quantifying why a punk riff recorded in a garage technically feels a certain way. But comprehension isn’t communion. They’ll stare at our relics the way a parent gazes at home videos of a young child’s play—knowing its fleeting nature, mourning its loss.

The very concept of “human-made” will gain new significance, just as “handmade” became meaningful only after industrialization. An ad hoc TikTok dance, a cringe brand tweet, a SoundCloud rapper’s mixtape—these may become folk art, not because they’re profound, but because they’re uncalculated. Future creators, drowning in endless AI-generated permutations, will envy our constraints.

For a century, between the crackle of AM radio and the first whispers of the LLM, we lived in a world sized for human hands. Looking ahead, AI isn’t our end—it’s the culmination of our obsession with making: we finally built something that makes better than we can alone. No one will celebrate a website coded without copilots, just as no one mourns the loss of dial-up internet. There’s a temptation to resurrect that era—to shove this genie back into its bottle. But as the Luddites of the industrial age remind us: progress like this is often inevitable despite any well-meaning hopes to stop it.

Our descendants will split their gaze: some tending to islands of pure human creation, others resultsmaxxing in endless machine-made worlds. But they’ll return, always, to our century’s archive—that last great collection of purely human noise. Not because it was better, but because our very limitations made it meaningful. In a world of endless possibility, our constraints will seem romantic; our imperfections, divine.

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Ask someone to define design, and they’ll likely describe what designers make—architects draft buildings, graphic designers create logos, industrial designers shape products, and software designers make apps. This is how we typically understand design, by its outputs. The weight of these definitions grows heavier over time. The older the craft, the more its history constrains what seems possible, what is acceptable, and what defines “good design.”

My parents are both designers—though they never used the word “design,” my father built boats and my mother made art. Growing up, their worlds of design engineering and artistic expression seemed to barely intersect. But over time, I discovered they were practicing the same fundamental methods of design. To each of them, design transcends output—it’s a way of thinking, seeing, and bringing ideas to life.

The distinction between design as mindset versus output matters more than ever—whether you are a designer or not. As AI reshapes how we create, we face uncertainty about which human capabilities will endure and which will transform.

This new ease of creation would seem to imply that products made with AI will soon not fall short of perfect. Despite this, something is still missing. The designer’s ingenuity, their eye for beauty, their vision of the whole, their understanding of the why and when something must exist will take on new meaning.

Product success will largely be determined by intention and vision—before anything is built, before AI or humans begin creation. As engineering becomes focused on pushing the AI frontier, design's role shifts to making these powerful but complex tools intuitive, accessible, and desired. Just as users choose products for their value rather than their infrastructure, they'll choose AI products for what they enable, not their underlying technology. This requires cultivating a new intelligence: one that combines craft and intuition with strategic thinking and execution.

Design and the profession of the designer must transform from a specialist function pushing pixels into a universal attitude of resourcefulness and inventiveness. We move beyond asking if designers should code to embracing design as a universal capability. This mindset adapts to any medium and isn’t focused on acquiring technical skills, tools, or reserved for specific roles.

This primal way of design exists in how early humans shaped tools & rituals, how children imaginatively arrange toys, and how investors rely on taste to back early companies. I see this type of design everywhere in my work with founders, engineers, salespeople, and investors—they are all designers in their own right. It is innate—it just needs to be unlocked.

Design as curiosity

My time at RISD and Brown transformed and formalized my understanding of design and its intersecting qualities. RISD taught rigorous craft, critique, and experimentation: the path to proficiency takes hard work. Trying and failing were essential to growth, forging a mindset that embraced complexity and ambiguity. Brown expanded this by showing how design as a methodology could apply to other fields—economics, entrepreneurship, engineering, media studies.

But at the time, I questioned this approach. Why study semiotics when I could be building a portfolio site? Why pull all-nighters just to endure brutal critiques—tossing the work away and starting over? But the process—thinking, making, critique—proved transformative. The school wasn’t teaching design as ornamentation or styling. Instead, it was an intense course in principled thinking and creating connections between fields of art and making. It forced you to depart from your comfort zone and expertise as an artist and then return to apply it with new knowledge. I recall working with materials like wood (not my specialty) and coming away with an appreciation for reading grain, understanding structural forces, and anticipating how pieces will be used and age. These skills translate surprisingly well to software design & development. The same careful attention to functional properties and respect for inherent constraints and possibilities applies whether you’re crafting joinery or designing apps. It’s not about superficially copying patterns from one domain to another but about developing an intuition for how fundamental principles—modularity, use, resilience, elegance—manifest across different mediums.

In retrospect, I find it ironic that at RISD and Brown, two schools which oppose the idea of professional training, gave me such invaluable tools for my work. You must learn the ground truth to know how to manipulate it. You can’t transform what you don’t understand. And you can’t know what you haven’t touched, haven’t built, haven’t broken.

Design as curation

These academic experiences taught me that design education isn’t just about mastering tools—it’s about developing an eye for what matters and what you like. This curatorial instinct, first honed in art history classes and cross-disciplinary projects, becomes essential when following your curiosity into diverse realms.

The richest insights are found in overlooked sources and connections that are beyond the reach of the internet and the incentives of its curatorial algorithms. My inspiration comes from unexpected places: the yellowed pages of out-of-print software books, modern science fiction essays, the writings of early religious leaders, and unique items in maritime consignment stores. Even DIY projects shape my perspective, like building a traditional sauna or making bookcases for my kids inspired by Dutch canal houses.

The journey of curation requires experimentation, and experimentation takes time. Each discovery reveals your preferences and how they fit together to comprise personal style and taste.

Curation leads to expertise. Through curation, you better understand yourself, history, and unlikely connections across fields. Increasingly, we will curate sources and ideas and let AI handle execution or assembly. Honing an ability to curate and arrange these sources will cultivate depth and meaning in your work—tuning the machine to your specific eye.

Design as conviction

Curiosity and curation train you to form principles as well as personal opinions, confidence, and a sense of “feel” around what is good. My mother, a painter and art teacher, taught me that good design—like art—draws from personal experience and perspective. She creates a conduit for her feelings, ideas, and beliefs. They flow through her natively.

Conviction often stands in opposition to market trends. To have conviction before validation may make you seem weird or delusional, but it defines great artists—the ability to appreciate what others overlook or even fight against. To borrow YC parlance, they pursue “low-status things.” Maintaining this vision requires courage, especially when it seems complicated or insurmountable. As all artists (and founders) know, this process is a fight, requiring persistence and relentless effort, particularly when others doubt or ignore your ideas.

This intrinsic motivation—creation for its own sake, the pursuit of “better than good”—is rare. When deeply held opinions drive your work, they shine through in their expression and are unique to you—in art, design, product, or company.

Design as obsession

My father embodies design to the fullest extent. He says, “It’s a lifestyle, not a job.” He brings the same intensity to everything—whether solving engineering problems, crafting sales messages, or building side projects. He brings opinion. He is a polymath maniacal about every aspect his work touches. He is obsessed.

When he built boats, he wasn’t selling fiberglass and chrome—he was selling performance, adventure, and freedom. Many customers wanted a piece of this world, drawn in by his passionate, authentic vision of what boating could be. My favorite of his taglines captures this energy: “The ultimate off-road vehicle.” The t-shirt featured a gleaming sportfishing boat outfitted with massive offroading tires cutting through the surf. He was obsessed with both the product and its distribution—the same energy that went into perfecting hull designs went into crafting the perfect story and sales.

His gift was communicating this vision with infectious enthusiasm while maintaining craft in every detail. He spent hours equally on factory floors and at sales shows—examining the technical through to the tactile. This isn’t just perfectionism that AI could replicate; it was a distinctly human integration of engineering pragmatism, market understanding, and relationship building. He didn’t just perfect hull designs—he understood how materials, shapes, and experiences made people feel and how technical details could translate into human aspiration.

This fusion of obsession and insight made him more than a boat builder. Every detail served a larger vision—he was a designer of both products and the company that brought them to life.

Design as orchestration

The designer must see the core as well as the periphery, the immediate and the ultimate. If obsession fuels this work, orchestration makes it productive.

My father’s single-minded attention to both detail and experience mirrors the approach of the best founders I’ve worked with. At Thrive and now Terrain, working with founders at the formation of their businesses, I saw how they designed products and entire systems—teams, workflows, and frameworks that scale.

These founders recognize that company design goes beyond playbooks, case studies, or podcasts. Consider how modern startups approach product development: A technically proficient team might build perfect features, but design-literate founders create experiences that make users feel something when using the product. Notion succeeded not through technical superiority but by understanding how modularity & collaboration could transform how teams work. Stripe won by treating documentation and developer experience as a first-class product—showing how design can elevate infrastructure often regarded as an afterthought.

Often, we see this brilliance in early versions of products—born from founder-built brute force and passion—only to see it fade with scale. Ultimately, you are only as good as your team, so you better craft it intentionally and with heart. The company becomes your great work. The best designed of these organizations become durable as they scale and create self-improving systems—from leaders developed within. This manifests in frameworks that scale while maintaining autonomy (Spotify’s squads), protocols that efficiently align expectations (Amazon’s memos), and systems that balance creativity with quality (Pixar’s Braintrust).

As AI democratizes individual capability, making it easier for anyone to create and build, this orchestration skill becomes even more essential for teams to set themselves apart. Orchestration creates conditions where talented people navigate complexity together, evolving beyond traditional management.

Design as literacy

Just as the printing press proliferated printed text and commodified knowledge and communication, AI is accelerating the speed of inference and democratizing access to intelligence — commoditizing creation and transforming technical competence.

While AI can generate endless “perfect” outputs, the crucial design decisions are innately human: which questions to ask, guided by feeling & relationships rather than pure logic, and aligning execution against context and strategy. AI might generate hundreds of landing page variants, but it takes design sensibility to know which will genuinely resonate with users and fulfill their needs.

This human element of design literacy will become as important as verbal literacy, not only in understanding culture and aesthetics but also in forming and expressing new ideas. It’s a new type of intelligence and design that will separate those who thrive from those who fade into the noise.

Startups are the ideal canvas for applying design literacy. They require continuous iteration, not static perfection, in order to succeed. They are not timeless; they exist and succeed in their moment alone. They cannot rely on distribution or incumbency, only original thinking, relentless iteration and, for those persistent enough, transformative growth.

What happens next?

Advanced AI presents two paths: one democratizing creativity and distribution like the printing press and internet before it, leading towards a new golden age of original creation. The other leads to algorithmic homogenization—where we succumb to efficiency—technical perfection masking constrained thinking and corporate sameness. In the latter, we slide fully into a world where intelligent automation reduces the art of what we make to refined outputs of the machine—lacking any semblance of the uniqueness or sacredness, erased completely for performance and scale.

In either, the undeniable fact is that we are working in a world of more as a result of AI: more content, more noise, more distractions competing for our attention. The challenge is consistent — how do you cut through and create meaning?

The winning path is clear: design literacy as a cultivated mindset, not another acquired skill—embedded in every role from engineering to sales. Teams that embrace this will take risks to build cultures where authentic expression outweighs safe choices, conviction beats consensus, and craft is prioritized more than algorithmic smoothness. This does not mean you turn away from the tools of the future. AI becomes a tool for developing this way of seeing—helping us iterate faster, recognize subtle patterns, and explore more possibilities than ever before.

I want to partner with founders who embrace this worldview. Like the best designers, these founders understand that in a world where anyone can build, what sets them apart is having the confidence to know what to build, who to serve, and why their products must exist.

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The last decade has created an industrialization and institutionalization towards building startups. Faster. Bigger. Broader.

Founding became a rung on the career ladder, not a creative act. Venture became about who could scale resources fastest, create the biggest exec platform, and be first to give you a playbook on how to build. All with good intentions — but incentives between investor and founder diverged.

That era has come crashing to a halt. We are now in a rawer, more chaotic moment for startups. The track is gone but in time we will realize we never needed it anyway.

This moment demands founders who call their shot. Those who look into the future, point to a specific point, and say: this is where we want to go and here is how we are going to do it. 

Today Eric Stromberg and I are introducing Terrain to back and support these founders as they bring their companies to life.

Terrain is a seed stage investment firm. 

We invest and partner during a company’s first year — not forever.

We go deep in a few select areas to drive outcomes and impact. 

When we work together, we match your energy, creativity, and intensity.

We’ve already started and made several investments to-date. Our first was in Base Power Company, announced earlier this week, with more to come.

We wrote a letter about the past, the future, and who we think will come to define it.

We'd love for you to read it here: terrain.com/letter

Today we see great architecture as timeless and absolute. It is a reason that building is such an adaptive metaphor. But so many were the result of disruptive evolution in their respective cities: Paris’ 19th century Hausmann blocks were regarded as a "destruction of Paris."

While you can visit a Hausmann building, you can never return to Belle Epoque Paris. Startups are similar. Just as you cannot revisit Paris in the 1870, you can’t revisit early Twitter and its close-knit community of 2008.

High growth startups embrace this state of fluidity. The timeless aspects are not product design or features — they are principles, customer focus, and dedication to certain ideas over others. Adopting this perspective shifts the focus from crafting a single, unchanging vision, to embracing the dynamism of the moment in time.

This approach has been helpful in the development of early startup ideas and narratives. Envisioning an early-stage company as a pioneer town within a newly settled valley prompts several questions:

• What will it stand for? 

• What resources does it have? 

• Who will lead it? 

• Why will it attract the 100th settler? 

• And crucially, what aspects will endure a century from now?

No one ever expects cities to be static (except maybe NIMBYs) — nor should startups. To thrive, both must transform over time, withstanding fleeting generations and demands while ensuring strength in foundational principles and visions.

For millennia our primary medium for well... everything… has been rectangles.

Stone tablets. Papyrus scrolls. Printed books. TVs. PCs. Smart phones. The rectangle has reigned supreme.

Does Apple Vision Pro have the potential to change our relationship with this mighty shape?

As everyone for the last week has heralded the start of the “spatial computing” era, they’ve also been quick to imagine dynamic 3D interfaces and a “breaking out of the box.”

But one of the most striking parts of the Vision Pro launch and early demos was that… everything was so… rectangular.

Yes, these rectangles escape beyond the confines of the phone or computer, but they’re still largely flat, UI rectangles.

The obvious take is that V1 of visionOS is a bridge. Much like leather-bound skeuomorphism for the early iOS and PCs with literal desktops to help users acclimate to this new interaction model and world. Just as we’ve seen in the past, we should expect this paradigm to break over time.

But the more interesting take is that, even if spatial computing does result in a new platform, we may never ditch the rectangle — that is, we will continue to interact with most content in these rectangles, even if they are beautifully rendered in a digital 3D space.

While this certainly is the more pragmatic future — I think it is also the most likely one — particularly for productivity. And even if Vision Pro (and subsequent versions) are an order of magnitude more successful than any predecessor VR devices, it will pale in comparison to iPhone scale.

And so long as the iPhone still constitutes the center of your digital life — scalable (spatial) rectangles will rule. Don’t get me wrong, I don’t see this as wholly negative.

Yes, there will be immersive 3D experiences, but I wager those will primarily be things that are already 3D in the real world. Experiences like modeling, interacting with objects in a real world manner, or fully immersed backdrops & entertainment.

For everything else... perhaps humans today are just like our cavemen brethren — reasoning with and interacting best with orderly content in two dimensions?

Why do we all shoot iPhone videos at concerts and sporting events or (worse yet) fireworks?

The iPhone camera is good at many things but this isn’t one of them. I’d also wager that the median views on most concert videos is 0. While it certainly takes you out of the moment, I believe this behavior is about feeling ownership. The act of capturing becomes a way to create a lasting memory, even if it is never revisited.

Digital notes and bookmarks are a bit the same… click the icon, jot something down, tuck it away, and never come back to it. There are a lot of tools to try to make sense of this saving and organization problem. I find that simplicity and speed are the most important facets of a tool in this category. This has led me to not organize, but instead, to simply use whatever is most handy. Usually Apple Notes, but also Twitter bookmarks, email drafts, etc. Pile it into the attic.

This attic then, of course, brims over. In my scheme, lots of boxes without always remembering what was tucked where. Rather than building some more elegant organization system, I have started regularly revisiting and clearing it out, harvesting the good bits… a spring cleaning every so often. This is both cathartic and allows a revisiting of past threads — with new perspective. 

The journey can stop there but I think that publishing this raw material offers another opportunity. When someone shares these ideas, you get a glimpse of how they organize and present their thoughts and the corners of their internet. These are not blog posts or essays. Their result is more akin to a well-kept garden or curated art gallery.

Some people do this really well. A few examples that come to mind are Patrick Collison’s Fast or Stu Griffith’s ReadJPEG. This idea of curating and inviting others into this semi-organized space was something we talked a lot about at the start of The Browser Company. Today it is core to their vision for exploring the internet beyond Google’s ten blue links.

In a recent review of my notes, I came across a collection of some wisdom that I collected from founders, colleagues, and others during my time at Thrive. I jotted these down for one reason or another in the moment — and I am happy that I did.  I’ve collected together a few of these notes below to share with you. I am pleased to now have some more room in the attic to collect new ones.

— —

Perspectives from the Thrive team & founders, 2018-2023
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Building a firm is different from building a company. It is about building trust between individuals and a flexible platform to rise to the challenge or opportunity dynamically.
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Investment firms can have a product as well: investment strategy, process, people, and ambition of partnership with founders.
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Taking a builder mindset to your work — building an investment firm as a product and company — is still rare and unique in this business.
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Lean on your team to improve your own independent perspective, not to seek consensus or outside validation.
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Founders are everything in this business. They are the heroes in this business. But their story is incredibly romanticized. Being a founder is very, very hard. Starting and incubating companies allows us to experience a small part of that alongside them.
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Building companies also gives an informed perspective on investing in products and markets. It enables you to be a more meaningful partner to founders as a result.
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The best ideas can come from anyone and anywhere — but they rarely come from the headlines.
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Being opportunistic doesn’t mean lacking focus — it requires extreme focus.
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Passion, tenacity, and grit will beat pedigree and experience every time.
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Listen more than you talk.
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Decision-making is simple if you always do the right thing. Doing the right thing is always the right thing. People remember how you make them feel about themselves.
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Focus on the inputs, not the outputs.
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Life is short and long. You grow more in moments of turbulence but what is constant is winning with integrity and kindness. How you show up in these moments, when it is not in your self-interest to support, are often the most important.
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The world does not end very often.
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Unpopular actions can result in the most popular achievements. Success comes from a willingness to be bold.
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It is equally hard to build something small as something big. So build something big.
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Having something to prove to yourself and being in competition with yourself is the greatest motivator one can have.
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Nothing you ever do at work will measure up to what you do at home.
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Show gratitude. Be present. Have balance.

— —

They say you become the average of the people you surround yourself with and I am lucky to have been surrounded by the thoughtfulness and culture of these founders and the broader Thrive team over the last five years. Onward.

So how do you go about it?

Like in any type of creative work, the best way to figure things out in startups is to just go and make things — consistently. Make small progress constantly. Talk to users, sell an idea, write code, design, share an idea, and seek out inspiration. Every big thing is made of many small pieces. Valuing the small, incremental progress matters.

How do you know if this is the right thing? You might not. One starting point is to follow your own excitement. That tends to be a good rule of thumb, especially when building for yourself. Another is to ask: will this matter in the future? If the answer is murky, maybe reconsider. 

Even making a wrong turn allows you to learn and see things you otherwise wouldn’t have seen. Each day your heading gets more accurate.

Lastly, learn to block out the noise around that big vision. Yes, you have grand ambitions. Yes, there are expectations. There is little value in sitting with those today.

Just show up and make something happen. Compound that learning consistently, getting off the ground, and the bigger vision will realize itself.

Go 1-0 today.