People are talking about how surprising it is that Mark Zuckerberg, i.e. Zuck, went direct for Meta’s Llama-3 launch this week. What is “going direct” though?

A kind of literal definition — “Going direct” is when people or companies skip traditional media to connect directly with their audience. According to Lulu Meservey, who I’d call Silicon Valley’s “new PR” guru, going direct “means crafting and telling your own story, without being dependent on intermediaries.”

Hence some people are saying what Zuck did isn’t exactly “going direct” — because he doesn’t control the channels. Because he went through intermediaries, even if not legacy media. But going direct isn’t about exclusively speaking via channels you own — it’s simultaneously more philosophical and pragmatic than that.

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I find there’s something to learn from almost anyone who does something really well. In fact, I strongly believe some of the best lessons and examples come from outside of your usual environments, communities, lanes. Sports isn’t one of the top things I study or write about, but every time I do, I come away with new inspiration — so hear me out.

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Last week I outed myself as a strong believer in granny hobbies for health. (I like to keep my domain purchases close to the vest, but I’ve quietly held grannyhobby .com for a while too.) A lot of people seemed to resonate with my confession, so Twitter then forcibly showed it to 2 million people.

The same week there were two related New York Times pieces (related because granny hobbies overlap a lot with the world of leisure-crafting): One profiled Happy Medium, a newco opening casual “art cafes” in NYC. The second was all about the brain benefits of handwork.

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In times of change, learners inherit the earth, while the learned find themselves beautifully equipped to deal with a world that no longer exists. — Eric Hoffer

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Greetings fellow theorists — I’ve been mulling over this one for a bit. I expect it’ll surface some strong opinions. I hope it’ll open up discussion for the greater good.

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This essay unpacks a principle for building products that I’ve been harping on for a bit.

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The famous phrase “do things that don’t scale” has a silent clause:

Do things that don’t scale in service of building things that do scale.

It refers to what startup founders should do to kickstart a company’s engine: manually recruit customers, service those customers, even act as a human-in-the-loop for a nascent software product.

I can’t help but notice though that after a successful stint at building things that do scale (or at least giving it a really good, long try), many people seem to gravitate towards building things that don’t scale.

I have a theory that chasing things that scale makes you need therapy, and the therapy is pursuing things that can’t scale.

II

I once wrote that every entrepreneur’s dream is to succeed at building an impossibly hard business and then finally open a local coffee shop to be happy.

I got a flurry of replies with people swapping out “coffee shop” for their preferred lifestyle enterprise — farm, ranch, restaurant, pub, orchard, bookstore, sports club, gym, ice cream parlor, hot dog stand, falafel stand, landscaping business, movie theater, library, flower shop, music studio, beach bar … there were more.

Even among high profile people, we see examples. One extreme case in point: Zuck (fka Mark Zuckerberg). He’s arguably built the biggest scale thing. As of some time in 2023, Facebook had more than 3 BILLION monthly active users.

Yet these days, a lot of what we see and appreciate from Zuck (and what it frankly seems like he gets a disproportionate amount of joy from) are his pursuits that can’t scale. He’s picked up martial arts and dedicated himself to mastering it. He’s adult-boyscouting with skills such as archery. Now he’s picked up cattle ranching too. And all of this seems integrated into life as more of a family man.1

Of course, he hasn’t given up on the impossibly hard, massive scale business thing. Unlike many ex-CEOs of similar status who’ve bowed out to the leisure life, Zuck’s still grinding away at the helm of Facebook, perhaps as an unrelenting competitor, perhaps on principle.

III

Chasing scale seems to be a kind of early life affliction. The more you chase it, the bigger the thing you chase gets. Perhaps it’s a natural desire to see how important we can be or at least how important our creations can be to the world (and hence how important we can be by proxy …). A desire to take on a seemingly insurmountable challenge, perhaps a noble one (though not always), and see if we can conquer it.

For most of history though, our visions of grandeur were limited by what we literally could scale. In recent decades, we’ve shattered these limits. Maybe the worldwide internet takeover and pay-per-flight space tourism (and yes, text-to-video AI) were the last things that had to happen to shatter the illusion of human limits once and for all.

Yet without limits, we try to find them. This is true on many levels, whether it’s about how big we want our creations to become or how people should be able to lead their personal lives or how much candy kids can eat after a Halloween haul. But I think having no limits is unnatural. Chasing scale to the level we do is too. Whether we succeed or not, it stresses the system and inevitably burns us out.

Then a new motivation seems to surface, a desire to pursue something that can’t scale. See, my theory is that chasing things that scale makes you need therapy, and the therapy is pursuing things that can’t scale. The antidote to burnout and the existential inquiry it brings seems to be doing things that don’t scale in pursuit of things that can’t scale. It becomes exciting not to see what you can do without limits, but to see what you can do with them.

What are these pursuits that can’t scale? They could be skills, like archery or chess or cooking. They could be close relationships, like making friends. Maybe it’s building a truckload of IKEA furniture. Or maybe it’s starting a local small business. These pursuits could be considered hobbies or something more serious. It doesn’t matter so much what it is than that it has a clear and visible ceiling.

IV

Most people who flirt with the heights of scale once could certainly try again. Some do. Others don’t, and maybe even choose to do nothing for a while after.

But most people eventually pick up a new pursuit. Often it’s something that they’d always had an interest in but wouldn’t have deemed “enough” before (scale demands compromise). One of my favorite stories in this distinctly weird startup world is of Audrey Gelman, the once high-profile founder/CEO of the Wing, who after moving out of the spotlight, started a country store in Brooklyn.

One way to rationalize this is that after being in the driver’s seat of such a large-scale, fast-paced effort, it’s hard for people to do nothing at all or go back to working for someone else. So pursuing something that can’t scale is a happy medium — maintaining full autonomy and control without the stress of chasing scale (and all that comes with it in terms of customers, investors, attention, etc.).

I think another driver of this sentiment and behavior is that chasing scale strips you of some humanity. It puts your head too high up in the clouds. It removes you from what happens in the real world with real people. Pursuing something that can’t scale does the exact opposite: it grounds you. It’s a comforting and healing next act.

Perhaps most instinctually, people just want to do things and get better at them. It’s an innate drive that even the wisest and most determined people can’t so easily turn off. I don’t imagine that people who summit Mount Everest decide to never climb another hill again, no matter how much it’ll pale in comparison. There’s always something to learn, to improve upon, even at low altitude.

Skeptics might say that this kind of exploration is only available to people who’ve “made it” financially or status-wise. I’d concede that any privilege makes something that feels like risk easier, but does this mean people without the privilege are fated to keep chasing scale forever? I don’t believe so. I increasingly see people who aren’t “post-economic” (or from wealthy family backgrounds) starting to question the pursuit of things that scale. They’re also questioning the traditionally hailed approach to chasing these lofty goals.

V

The natural next question is: why don’t we just do this from the start? Why do we need to go through the ups and downs of chasing scale only to come back down?

I don’t have the definitive answer, but I think it lies in our self-image — that humans are explorers by nature. “One of our gifts as humans is our ability to picture ourselves in places or situations that we have never been.” Yet, not everyone has the same urge to chase scale. Perhaps some people are relieved of this drive by their peers and mentors. Or maybe they were just born that way.

One of my favorite pieces of modern wisdom ever uttered comes from Jim Carrey:

“I’ve often said that I wish people could realize all their dreams and wealth and fame so that they could see that it’s not where you’re going to find your sense of completion … No matter what you gain, ego will not let you rest. He will tell you that you cannot stop until you’ve left an indelible mark on the earth, until you’ve achieved immortality … As far as I can tell, it’s just about letting the universe know what you want and working toward it while letting go of how it comes to pass. Your job is not to figure out how it’s going to happen for you, but to open the door in your head. And when the door opens in real life, just walk through it.”

There’s nothing wrong with the pursuit of doing something big, especially if the desire sprouts organically through action and even a sense of duty. But there are trap doors along the way. “Scale” can hide within it the vices of grandeur — of chasing wealth, fame, status, and the rest. Regardless, once “scale” is within your grasp, it starts to look less marvelous. That’s when you start to reconcile in earnest what matters and how small anything we do is in the grand scheme of it all.

Chasing scale will always be a part of the human experience. So the best advice I give myself and anyone else will listen is to stay grounded in your pursuit. Don’t abandon the myriad interests and opportunities that come your way just because they can’t scale. Don’t defer them for “later,” for your soft retirement plan.

Society tends to paint a picture that the final act of every big dreamer’s journey is in scaling up to unimaginable heights, but I think it’s the opposite — it’s actually in scaling back down after trying to reach the proverbial top. Make time to pursue things that can’t “scale.” I’d bet it does you as much good as “real” therapy ever could.

If this essay resonated with you, you might enjoy these spirtually related pieces:

• Status Limbo, about the place you land when you step off the career ladder

• Love the Mission or Love the Game, about finding your core motivation

• Rise of the Silicon Valley Small Business, about scaling with small business values

Working Theorys is entirely reader-enabled. If you enjoy my writing, consider liking it or sharing with a friend or becoming a patron. Thanks for reading!

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Nearly every entrepreneurial origin story you hear is about someone with such a strong passion for something that they couldn’t help but manifest it into existence. Usually it’s a passion for solving a particularly troubling human problem or a deep curiosity for exploring a given subject or an unyielding obsession with a futuristic idea. But what we don’t talk enough about is a deep love of the game of building “enterprises” itself.

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I started angel investing in 2019. The first check I wrote was a $10K check into a consumer health company. I was actively evaluating consumer health ideas to build, and my sister, a practicing physician, was a classmate of the founder.

Fast forward to today and I’ve done ~ 15-20 angel investments, which crosses some threshold for being “active.” I consider what I do, and what many others like me do, to be “freelance angel investing.” It’s not a hobby, not a full-time job, and there’s no institutional affiliation or long-term commitment.

Hence, I haven’t been focused on hitting investing quotas and the like. I’ve more so spent this time figuring out what being a good angel investor means and how I want to play this role in the ecosystem. And meanwhile, the number of angel investors, and maybe even the meaning of the phrase itself, has changed a lot.

I’ve had many thoughts of late about the topic of angel investing and how it is evolving, spurred on by the ever evolving startup ecosystem and of course broader market and technology tailwinds too. I want to unpack those thoughts here.

P.S. This essay’s more freeform, candid, and self-reflective than usual, and hence a subscriber-only post for now. This will probably be most interesting to early-stage angel investors, those considering getting into investing, and the generally investing-curious.

A few topics I’m going to cover:

• why I angel invest

• what my angel portfolio looks like

• reflections on my process, good & bad

• archetypes of modern angel investors

• how I think angel investing is evolving

• who I believe should angel invest now

Heads up: some of these sections have a lot of prose, so I wrote a quick summary at the start of each so you can more easily skip to what’s most interesting to you.

I. Why I angel invest

Tl;dr — I angel invest primarily to build strong connections with smart, like-minded people and expand my own tactical knowledge of spaces I care about.

My interest in angel investing started with my interest in making things. I started my first startup about a decade ago, and though it wasn’t successful on traditional metrics, I learned a lot about creating something from nothing, building a team, what aspects of entrepreneurship I liked and disliked, and many what-not-to-do’s.

Since then I’d always liked meeting other founders, learning about the ins and outs of their vision, teams, products, and progress. So as I thought about founding again, I naturally found myself around more founders — wanting to help those working on ideas that I gravitated towards yet didn’t see myself going all-in on.

So one appeal of angel investing was just being involved in the journeys of people I wanted to talk to and companies that I had a personal interest in. Another was the allure of “picking” — the game of making my own assessment of a team, product, market, and betting on it. Everyone likes to see if they’re “right.”

And perhaps third, I knew I would be playing in the startup ecosystem for the next chunk of my life, and I had an interest in multiple sides of it. For a minute I considered VC as a career, but I wasn’t all-in on it, so this was a way to keep that part of me — the one that gets to learn at the higher level, to understand markets, to see patterns, curate my own perspectives, and help other builders — alive.

The last reason is the possibility of a financial win. In part because I have invested my own money, I’ve been conservative with check size and number of investments. And hence, the potential financial outcome of any given investment still isn’t life changing and not on any immediate timeline either. Hence it was the least of the reasons, and it still is now (more on this later).

I don’t think the order of prioritization was clear to me at the start, but this is roughly how I’d rank the reasons I angel invest now:

• Get to know and support people that I respect and that have shared interests

• Better understand the lifecycle of products and markets that I care about

• Cultivate the generalist and analytical thinker in me

• Have fun playing a game

• Possibly make money

Side note: There was a window in 2021/2022 when many people floated the idea to raise a small proof-of-concept fund. I believe I had enough of a point of view, track record, and network, but I wasn’t so sure about managing other people’s money as a formal job. 

II. What my angel portfolio looks like

Tl;dr — 15-20 investments, mostly in consumer, median check size of ~ $5K.

Let me add a bit more color to my angel investing over the past few years.

• Done ~15-20 angel investments. Most were seed stage, some pre-seed, one in Series A (and 2 investments in small VC funds that focus in these stages).

• Majority of investments in the consumer space, focused on social, media, creators, community, and games (which I find tend to have a lot of overlap).

• Secondary spaces I’ve been interested in are tools for startups and the future of work broadly and in consumer health and wellness.

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We’ve heard of zero-sum games and positive-sum games. Similarly, there are zero-sum products and positive-sum products. One isn’t inherently better than the other, but it’s valuable to know which you’re building. If you do, you’ll have a much clearer picture of what success is and how to (and not to) go about getting it.

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A little while ago I was back in the idea maze. I’d learned something each time I’d been there before. So I came prepared with a short list of attributes of the kind of thing I wanted to create next.1

Of course the idea maze doesn’t just have one good idea. You usually discover many good ideas, so the real question becomes — how do you choose? It’s not having an idea that’s the bottleneck, it’s having enough conviction in one.

This time around the idea maze I learned something that I hadn’t accounted for in my list — that the best idea is rarely the new, shiny one. It’s actually the best idea that won’t go away.

Old ideas are better than new ideas

Ideas can be new or they can be old.2 (And by this I mean new to you, or old to you). Perhaps counterintuitively, I think old ideas are almost always better for you than new ideas. And the “idea that won’t go away” is by its very nature an old idea.

New ideas have that new idea energy.

They fill you with optimism. You feel the high of the “eureka…

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About a year ago, I published my thesis on the Silicon Valley Small Business, a new startup archetype that combines big tech know-how and ambition with small business principles. Importantly, the SVSB isn’t about small outcomes; it’s a set of principles for any size outcome. One of the principles is about not relying on outside funding by default, yet not dismissing it entirely. I explore this idea in greater detail in this essay.

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There’s an age-old debate about whether you should go to business school or not. It rarely comes up these days but yes, I went to business school — arguably to the most business-school-y of business schools, Harvard Business School.

Business school isn’t “popular” in modern Silicon Valley and the startup world. Yet, more than a few of the “in crowd” have an MBA, and many more have considered getting one. There’s also lots of skepticism about the future of higher education. But that’s all besides the point and for another time.

I want to talk about what you should do if you happen to find yourself there.

The best thing you can do in business school is actually start a business.

(Yep, this is the punchline to the essay. If it’s all you remember from it, I’ll still be happy.)

Starting a business any time is very hard, so this might sound crazy, but it’s not.

If you’ve never started a business before, but you think or even know you want to “some day,” just do it in business school. (If you have started one before, it’s still a great time to take another shot at it.)

There are lots of reasons why it make sense to start a business in business school:

• You have an incredible amount of resources around you (in fact any sizable educational institution does, let alone one that’s focused on business)

• Your professors, peers, alumni all are potential mentors or even customers

• There’s often non-dilutive funding accessible to students with new ventures

• You’re not holding down a job at the same time (for most full-time MBAs)

• You have to keep up with classes but don’t need to chase a certain GPA

There are always objections of course; these are some of the usual ones:

• You need to focus on your classwork and learning

• You need time to build your social and professional network

• Recruiting for post-grad jobs takes up all your “free” time

• It’s hard to do the business justice unless you’re “all in”

• You didn’t need to go to business school to start a business (this one’s sneaky)

My response to these objections: if you can treat it as a key objective, you can usually figure out how to make it work alongside everything else. And the sooner you start, the sooner you’ll find out if it’s something you enjoy, if there’s a future in this path, or if not, what to do next.

Don’t view business school as a pit stop or a break. View it as a limited period of time in which you can take a risk with a lot of resources backing you up.

The other type of objection sounds like this: “I’m not sure I want to be an entrepreneur.” And to that I’d say — you don’t have to commit to being one. But even still, here’s why it can be useful to take a swing at it:

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We often think of “social products” as synonymous with “social networks,” but they’re not. Social networks are just a subset of social products, though arguably the most popular and lucrative kind that we also talk about a lot.

But I think it’s the wrong time to build a new social network. There’s something more compelling to build — something I refer to as a social utility.

Why not build social networks?

The current context is this: we’re in an era of legacy social network dominance and what feels like category saturation too.

Facebook, Instagram, TikTok, Snapchat, X (fka Twitter) are the big players. And the barrier to durable entry for any new social network seems extremely high. We see this with the plethora of new apps that launch seemingly every day yet very, very rarely find a value proposition that sticks.

Eugene Wei’s famed Status as a Service outlines three dimensions to evaluate social product strength — social capital, entertainment, and utility. The essay focuses mostly on status and how it’s valued and accrued by creators across the different kinds of social networks that have scaled.

Wei doesn’t dissect the entertainment dimension, but it’s of course a big value prop for the consumption use case. And on utility, he briefly opines:

Utility doesn't require much explanation … a social network like Facebook allows me to reach lots of people I would otherwise have a harder time tracking down, and that is useful. A messaging app like WhatsApp allows me to communicate with people all over the world without paying texting or incremental data fees, which is useful. Quora and Reddit and Discord and most every social network offer some forms of utility.

An overwhelming number of builders have launched social networks to tackle the social capital and entertainment use cases. The success cases have only amplified the allure of building networks — the opportunity for virality, tremendous scale, strong network effects, and massive financial value.

Relatively fewer people have focused on utility. Even when they do, it’s usually done more quietly. However, I think utility is a very valuable dimension that’s been underexplored by product builders and philosophers alike.

So, yes, you could try to build a new social network via one of few challenging strategies. Or instead, as this essay calls for, you could build what I call a social utility — I believe it’s an especially good time to do it. So let’s dig in …

What is a social utility?

In his piece, Come for the tool, stay for the network, Chris Dixon talks about utility as a strategy for bootstrapping networks:

The idea is to initially attract users with a single-player tool and then, over time, get them to participate in a network. The tool helps get to initial critical mass. The network creates the long term value for users, and defensibility for the company.

He cites Instagram as an example — its first feature was photo filters, a single-player tool for edit photos before sharing them elsewhere. Of course Instagram eventually became the place to share those photos, connect with friends and discover others, an evolution into the network we now know.

Dixon’s examples focus on the “single-player tool.” The tactical value is this: you only have to serve one user instead of getting a critical mass of users to join, connect, regularly use your product, and create a strong network effect. Starting single-player helps you refine a product’s value for individual users and stabilize retention on the basis of that value before introducing social or network features.

Both tools and networks offer a kind of utility to users, so I think of them as two ends of a utility spectrum. Not every network starts with a tool, and not every tool becomes a network. (Of course networks can offer tools too, but the core value prop tends to come from one side.)

Along these lines, there are single-player tools, there are social networks, and there is something in between that has aspects of both. I think of these as social tools, or social utilities.

Here’s a tactical definition:

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I was one of these kids. I had so much potential — to be a great surgeon, to be a great lawyer, to be a great musician, to be many great things. I got used to being someone who had the potential to really be someone. And it was a good feeling.

One that I soon learned didn’t hold as much value as it at first seemed.

II

One problem with having “high potential” is that it’s a false identity. You can’t be someone today on the basis of a fictional future you that hasn’t yet arrived. And when your present identity is too dependent on your future (more impressive) identity, you risk wanting to just merge them out of what I refer to as ego-convenience. The problem is, if you merge…

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What's one way to maximize your startup's chance of success? Be a big TAM founder working on a smaller TAM startup.1

This probably sounds unsavory. We're so used to talking about maximizing everything: Pick the biggest market. Tackle the largest problem. Chase the greatest outcome.

Investors definitely want you to do this. You want to do it too. It's brave. And if it works, you're brilliant. But it's also the most risky. You have less control in engineering its success.

So what's the polar opposite? Pick the smallest market. Tackle the smallest problem. Chase the smallest outcome. (Go ahead, you can cringe a little. But then actually think about it.)

Here's an example of this very idea in action: newsletters.2 You've seen the jokes about the smartest people in the Valley starting a Substack instead of an ambitious VC-backed startup.

Who are they? Big TAM founders. People who have the experience and skills to tackle something with huge potential. What are they doing? Working on a small TAM startup (at least a noticeably small-er TAM than they're believed to be capable of tackling). And why? Because they see a higher chance of success, even if the potential outcome is smaller.

To drill down more, they see less market risk. And even the execution risk seems manageable. Execution is largely a matter of operational consistency (e.g. sticking to a newsletter format and schedule) rather than niche expertise (e.g. retail supply chain management). As a result, a smart generalist can run the business, and it can just hire more smart generalists to help. A newsletter is also what I’d consider a positive-sum product, making it easier to succeed without strictly competing. Podcasts and other relatively low-budget, media-focused projects have similar attributes and appeal.

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First, what is a "public intellectual?" Here's a solid dictionary definition — "an intellectual, often a noted specialist in a particular field, who has become well-known to the general public for a willingness to comment on current affairs." It's arguably vague, but they have a big impact on public discourse.

So, who is the modern day public intellectual?

The most identifiable people in this arena aren’t "traditional" scholars. They’re usually not researchers, scientists, or writers by education or trade. Instead, they seem to have just put themselves forth as vessels — to study the world, share their observations, and sprinkle in their own thinking along the way.

The other thing they have in common: they’re men.

At least the most "top-of-mind" ones seem to be. What’s the basis of this? Well, a lot of observations and studying the world. And asking who comes to mind when people hear the phrase “public intellectual.” One friend rattled off names of several prominent men, then paused for a minute and named one woman, admitting she needed to think longer to diversify the list.

What kinds of men are these public intellectuals?

I call the first kind the “new media men.”

The work-life generalists like Tim Ferris. Social scientists like Sam Harris. Long-form interviewers like Lex Friedman. Modern shaman like Andrew Huberman. Social psychologists like Jordan Peterson. Sociopolitical pundits like Ben Shapiro. Modernized network hosts like Jon Stewart. Why do we all know of them? They preach on widely applicable topics and have adopted new media to go direct, to reach us online and in our ears.

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I've realized that one thing I really enjoy about writing is that I can do it all myself. Idea, draft, edit, design, publish. But when I build software products, I have to rely on a trusted partner (I've written a few lines of code, but I'm squarely the "non-technical" founder).

Usually people tell you this isn't a good mentality to have — the desire to be self-sufficient, nor to actually do everything yourself. But I kind of disagree. I think it's good to be able to do everything yourself (even if you don't always end up running at things solo).

Whether it's writing, building products, or something else — I think it's good to be full-stack at something.

What does it mean to be full-stack?

The "full-stack" label is usually an engineering description. Being a full-stack engineer is like being a "technical" renaissance man. The solo founders just hacking away at project after project — usually full-stack devs. The coveted first eng hire for a startup without stellar technical chops — often a full-stack dev.

With the creator economy maturing, I’ve also heard the phrase “full-stack creator.” It usually describes an online content creator that can do it all themself. The actual tasks, e.g. scripting, speaking, film, editing videos, designing, coding (or no-code). And the overarching domains of audience building and marketing.

I haven’t heard the phrase "full-stack" used in many other fields, but I think it exists in every single domain.

What does it mean to be a full-stack designer? A full-stack marketer? A full-stack founder? A full-stack investor? A full-stack writer? A full-stack performer (maybe the closest is the “triple threat”)? What does it mean to be skilled, or at least have a working knowledge of something, in totality — from end-to-end?

What's the benefit of being full-stack?

There are a number of reasons being “full-stack” is good for you.

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