Packy McCormick, one man show
The writer and investor talks about one-person trillion-dollar-organizations, burnout, and optimism.
Written by Meghna Rao
Photography by Amir Hamja
In some ways, Packy McCormick is in the running for one of his grand ideas for the world: within two decades, we’ll see a trillion-dollar-organization run by a single person, a solo creator who will be able to creatively stack a suite of mega-powerful APIs or plug into a DAO to produce as much value as an entire organization. And not just any organization — only five companies are worth $1T as of mid-July 2022: Amazon, Alphabet, Microsoft, Saudi Aramco, and Apple.
But McCormick is a self-professed generalist. He’s taken himself out of the race. “By the time the technology gets to the point where someone like me can do it, it’ll probably be too late, there’ll probably be too much competition,” he laughs. “I’m picturing someone younger and more technical than me. Maybe my son.”
To start, then, maybe McCormick will be among the cohort of multi-million-dollar one-person organizations that proliferate in the next 20 years. McCormick launched his free Substack newsletter Not Boring at the start of the pandemic and has managed, over these two and a half years, to become a man of the moment. He’s grown his audience from 400 readers in March 2020 to over 125,000 as of June 2022, raised two funds off the hype of that audience and the quality of his words, and made at least 30 investments in startups of all sizes.
And he’s done it all without the help of a full-time team. Instead, he’s tapped into a range of companies to get set up — a clunky toolbox of products and services that don’t work very well with each other but are effective and sharp on their own, and are still miles ahead of what we had access to five years ago.
Substack to run his newsletter, Figma to make graphics (mostly watermarked memes), Descript to record and edit audio versions of this newsletter, and Twitter to shill his work and build an audience. From his newsletter, McCormick makes money in two ways: ads placed in his newsletters and strategy deep dives, like he did for Ramp in December 2020.
That’s the tech and growth stack, but then there are the parts that are unquantifiable, like what exactly is it that makes McCormick's pieces hits. With easier access to tools comes more competition. And yet, McCormick has been able to anoint himself as one of tech’s de facto storytellers, part of a cohort that include The Generalist’s Mario Gabriele and Lenny Rachitsky, insiders who chronicle what’s happening across the industry with speed, expertise, access to insider sources, and a generosity that’s not often granted to the industry by institutional media.
One (unnamed) close friend of McCormick’s describes his particular je ne sais quoi as voice-market fit — maybe it's that he launched during the pandemic into difficult times with infectious optimism, the likes of which many of us left behind in the 2010s. The type of optimism that would tell you that the pandemic might have been the "greatest catalyst for progress and creativity in human history."
Once McCormick writes about a concept, he formulates a thesis. From there, he funds companies. And then, he writes another thesis. “I only invest in companies that I want to write about,” explains McCormick. “Otherwise, why would I invest in them?”
So far, these qualities have helped him raise two funds and a syndicate. His first investment was in July 2020 in Apt, a startup that standardizes housing development by developing and operating low-rise multi-family homes.
“Not to be overly humble, I used to think that investors were something that I could never be,” he remembers. “At first, I’d be like wow a company wants me to invest?!”
As a “solo capitalist,” McCormick doesn’t have the challenge of larger funds — he moves fast. He is the general partner, the one who runs due diligence, the one who approves investments. No bloat whatsoever.
McCormick’s thesis behind the solo, mega-powerful organization is as follows: new technologies will help individuals hook up to tools that others have built without having to write a single piece of code. The time saved will let these individuals add previously out-of-reach abilities to their stack. They will move faster and smarter than ever before. And these technologies will evolve at a rapid pace.
To some extent, that has already happened. Like the seven lines of code from Stripe’s API that allow just about anyone to accept payments (and much more) — these seven lines also make it so that you can get access to the company's tools, including their engineering team that updates code 16 times a day, without you having to do any of the legwork.
But Stripe has become so commonplace that there are rarely any oohs or aahs when we see a new website that uses the company to accept payment. We’re already ready for the next step. It’s a simple cycle; start as revolutionary, become commonplace, eventually become infrastructure.
To use a McCormick-specific example, imagine that there is a newsletter platform that lets writers hook up to an NFT marketplace's API. With the API, writers can mint and sell iconic memes as NFTs directly to their readers (maybe McCormick will mint his image of John Updike touting Excel).
Or maybe the newsletter platform will let McCormick add the API of an automated fundraising tool like Party Round to his newsletter, so that readers can read his pieces and hit “invest” right alongside him afterwards.
Suddenly, solo-corporation McCormick can do much more than before. And these new capabilities don't exactly need to come from a string of APIs. They can be built on the blockchain. And they can even be open.
“I’m imagining the start of this open, minimally extractive infrastructure,” McCormick says. “And a lot of the ideas snapping into this infrastructure will get better and better.”
At first, McCormick adds, these new technologies might seem like they only empower the existing winners. If a company the size of Stripe plugs into a low-effort high-value tool, they'll reap much more than if a company the size of McCormick does it.
But these aren’t winner-take-all moments; McCormick envisions a world with endless opportunities. A big organization might move slow and take its time to make a decision. And a one-person organization might enter in the meantime, see possibilities that no 1000-person company could, and extract millions worth of value.
McCormick wasn’t always the type to go off solo; raised in Philadelphia and a product of Catholic schools, McCormick graduated in 2009 into a job in finance at Merill Lynch. When he grew bored with the lack of autonomy, he turned to AngelList and went all-in on interviewing with Breather, a startup that gives people in Manhattan spaces to nap.
“When I was working in finance, I always knew I wanted to nap, but there was nowhere to sleep,” he remembers. He wrote his own job description and interviewed nowhere else. “I was like, oh wow, you could just take a network of spaces all over the city where you might go take a nap in, kind of like you had in school. This is great.”
Breather had a hard time taking off; it later pivoted into co-working spaces. By then, it was up against the likes of WeWork. Plus, McCormick adds, the demand just wasn’t there. Everyone wanted a workplace pod, but Breather had made a fatal assumption — the big, vacuous-seeming buildings around Manhattan weren’t just willing to give up their space to some company that would bring in a revolving door of strangers.
Work began to get rote. McCormick started writing. He went to David Perrell’s famous writing course; mostly, he explains, writing was a way for him to remember who he was, a way for him to remain himself.
“I’d just be sitting in meetings, and — this isn’t an insult to anyone — would look around and feel like there was no way to remain intellectually curious while I was still there. I’d say, I don’t want to become like these people. I had to write to change that.”
When McCormick quit, he was six years into Breather. He briefly tried to raise money for what he describes as “Soho House meets college extracurriculars,” a place for people building things to convene. “A few people talked me out of raising, other people talked me out of building before having a community — thank God,” he laughs. “And my wife was saying, ‘it’s a dumb idea,’ but in much nicer words.”
"I only invest in companies that I want to write about. Otherwise, why would I invest in them?"
And then, the refrain that’s now become common: the pandemic hit. McCormick’s wife was pregnant. “Shake ups are really scary and they can be good,” he says. “I decided to go all in on writing. A few of my friends were like, what the fuck is Packy doing? They were just kind of making fun of me.”
But McCormick kept writing his newsletter. Soon, link roundups turned into pieces; his initial newsletter name Per My Last Email turned into Not Boring.
Later, when I sit down to write, I try to remember the patterns on the wallpaper behind McCormick. Blue whales with frothy spouts. No, they were island palm trees with dancing leaves. But my memory fails me.
Maybe I should have taken McCormick’s advice and written it down; when I ask him about how he takes notes, he doesn't answer my question directly. Instead, he tells me about his grandmother, who was diagnosed with Alzheimer’s a decade ago.
“I realized that I write as much as I do because I’m afraid of losing my memory,” he says, still smiling, even then. “I forget a lot of things. And writing, for me, is a way of not forgetting."
What feels difficult about the solo organization — whether one is making $1T, $100M, or $10K — is the emotional toll of working alone at a high-performance job. No coworkers. Only one person to bear the brunt of making mistakes.
But McCormick dismisses this worry quickly. He says he’s got the community angle covered. He can plug in easily into his Twitter and Telegram groups. Plus, he’s got his wife, his family, and his brother for emotional support.
And, McCormick adds, he’s not as solo as he once was. He co-writes pieces more often. And he’s recently added two part-time research analysts to his team: Elliot Hershberg, who’s getting his Ph.D. in the department of biogenetics at Stanford, and Rahul Rana, who’s studying astrophysics and finance at Rutgers. They’ll work with McCormick as long as they'd like, until they're ready to go off and do their own things.
“I want to work with people who can help me be more cutting edge,” McCormick explains, “to tell me — you’re either buying too much into the hype or you’re missing this whole area. And I want to be able to move earlier-stage with people who can analyze the earlier-stage stuff.”
Then, there are the mistakes. Being a creator is difficult. Being a creator whose business is built on accurate, hyper-timely takes is even more difficult.
"Writing, for me, is a way of not forgetting."
About a week after we talk, McCormick is — for lack of a better word — “canceled.” He makes an off-the-cuff remark about web3 and the internet pounces on him, from his audience on Twitter to commentators on Reddit.
It’s an odd coincidence considering our conversation the week before. I’d asked him about cancellation, and his answer is clear, like he’s already pre-empted that it will happen. “I’m pretty clear that what I’m saying is not gospel,” he says to me. “I’m learning and writing a lot of things at the same time.”
A week after the debacle, he releases a post on optimism, quoting physicist David Deutsch to explain that one of the goals of optimism is “a way of explaining failure, not prophesying success.”
In essence: we all make mistakes, be kind, the way of the future includes some leeway. That’s the only way an individual can rise up to their full potential; that’s the only way we’ll create multiple one-person organizations.
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