The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 36 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
McCormick: I likely would have written a positive sponsored post on Theranos
“One of the tests that I always run for myself, and I probably actually would have failed this test, is if Theranos had come to me on a sponsored post, you know, however many years ago, chances are, frankly, I would have written something positive on Theranos b…”
McCormick: Independent creator-investors lose value when joining traditional venture firms
“As soon as I go in-house somewhere, Like I lose half of my value or, you know, X percent of my value as soon as I go in-house somewhere. And that is kind of one, even though, you know, I do do sponsored posts and all of that, there is like this independent voi…”
McCormick: Opendoor stock will outperform rivals due to its iBuying lead
“I think that Opendoor is gonna do the best. I think they have the biggest lead in, in iBuying, and I think that's a huge, huge opportunity Particularly because they have the best company value in all of the world, which is bips for breakfast.”
McCormick: A DAO with physical locations is perfect for modern social clubs
“I mean, today, what not boring club would have been is really a Dow probably with physical locations. I think actually that model works really well for what I was trying to do at the time.”
McCormick predicts Not Boring will cross $1M in revenue in 2021
“And I have a few pieces kind of coming up, and so I think chances are we're going to just kind of cross a million dollars in 2021.”
McCormick: 80% of DAOs will fail, but the top 20% outperform corporations
“I think Eight out of 10 DAOs might totally fail because they have like kind of that leadership issue or like who is the final decision maker issue. But I think those other two are going to do things that like you might not have ever thought to do with a tradit…”
McCormick: Not Boring Capital never led a round across 91 investments
“Did you lead a single round? Did you write any term sheets? Were you the biggest check in any one of those 91 investments? Never. And that's all part of the strategy, right?”
McCormick: Not Boring Capital does less diligence than most co-investors
“I wrote in both the public and private memo that like I'm doing probably less diligence than most people on a specific company than most people who are investing in a company will.”
McCormick details the scope of his advisory role with a16z Crypto
“The advisory there is like, you know, working with some of the companies in their portfolio to think about how they tell their story, writing pieces. Like I wrote with Chris in the economists, like they'll introduce me to companies, you know, that they've inve…”
McCormick: Opendoor generated an adjusted EBITDA profit in 2021
“They finally turned, ah, an adjusted EBITDA profit last year so they can make money on this business.”
McCormick: Playing an online persona makes creator work unsustainably difficult
“If you're not yourself, it's not like a be true to yourself kind of thing. It's like, you're going to have a miserable experience because all of your interactions are going to be other people wanting to interact with this persona, or if I were writing from a d…”
McCormick: Paid newsletters succeed when companies expense them for specific roles
“Lenny's audience is so specific and like, you know exactly who you are and who should be paying for that, which is people who do product or people who do growth. And not only do they know that they should be reading that and that they need to pay for it, their…”
McCormick: A tech bear market will lead to attacks on my optimism
“I think when the market turns and when we enter a bit of a bear market and in tech and web three, like it will be really easy to throw stones at me. Like I am unabashedly optimistic about all of this and like things are going to turn on. I'm going to like, you…”
McCormick: Independent investigative journalism is severely limited without institutional legal backing
“I think it's really hard to do that kind of journalism. Independently because you need lawyers who have your back and you need editors to make sure that you get everything right. And you need like all this stuff to protect you when you're doing this really bra…”
McCormick: Solana's token increased 3.5x two months after his deep dive
“And then of course, Solana, like three and a half X in the next two months.”
McCormick: Running a venture fund scales better than writing sponsored newsletters
“It does scale a lot better to run a venture fund than to show up every week and get a sponsor and then write, write an essay.”
McCormick: I made 91 investments in Not Boring Capital Fund 1
“Fund when I did fund when I did 91 91 investments and not all of them have investment memos.”
McCormick: Expanding creator brands beyond core content risks turning into shill factories
“The more I do of that stuff, the more dilutes the core thing. And the more it makes it seem like kind of a shill factory”
McCormick: Not Boring can reach 1M subscribers within five years
“There's a path to this being a million person newsletter at some point in the next five years.”
McCormick: Becoming a full-time VC partner would never be attractive
“I've had that other conversation with funds, too, where it's like, hey, you want to come work and, you know, be a full-time partner at this fund? And no, like, we've talked for the past couple of hours about how much fun I'm having doing this particular thing,…”
McCormick: Winning founder allocation depends on if they are already active readers
“I don't think it's gotten, you know, any easier convincing founders to give me allocation at 50,000 readers or 88,000 readers. Like if they're a reader, then they kind of get it. And if they're not, then You know, they don't on the sponsorship side. It's diffe…”
McCormick: Venture funds cannot deploy a billion dollars purely with follow-on checks
“It changes the strategy completely though. You can't deploy a billion dollars in follow checks.”
McCormick: I bought 38 Bitcoin at $100 and sold at $150
“I bought Bitcoin at a hundred, sold it at one 50.”
McCormick: I was the largest Uber Rush consumer worldwide during Breather's expansion
“We actually, I was the largest consumer of Uber rush messengers in the world for a while.”
McCormick: Breather launched a space daily in 2016-2017, crushing gross margins
“We added a space per day in. 2016, 20 17 for about a year there. Every day we were launching a new space. And so we were deeply oversupplied. Our gross margins were awful, negative, I think -25%.”
McCormick: Substack is completely free for Not Boring's ad-supported model
“The most beautiful part about sub stack is because they've taken such a strong stand for subscriptions and against advertising. No one on their team has ever even reached out to me. And so I paid zero dollars for my main platform because they want to pretend l…”
McCormick: Ramp raised at $1.1B and $1.6B valuations in one deal
“It was ramp. And like they're kind of double unicorn round when they raised at a 1.1 billion dollar valuation and a 1.6 billion dollar valuation in the same transaction.”
McCormick: Startup where I worked sold for $3M after raising $120M
“I was an employee, not a founder. At a startup that sold for three million dollars after raising a hundred twenty million dollars.”
McCormick: Not Boring reached 105,000 Twitter followers and 88,000 newsletter subscribers
“I'm like, you know, a 105 or something on Twitter and 88 in the newsletter.”
McCormick: Not Boring Fund II would potentially target $25M to $30M
“And fund two, were it to exist would potentially be in the 25 to thirty million dollar range.”
McCormick: Not Boring has severe key-person risk and momentum slows without me
“If I get hit by a bus, like not boring is just done. And that's like the extreme example and the example that everybody uses when they talk about one person things, but that means that like every week, if I don't show up and write something, the momentum slows…”
McCormick: Not Boring adds 1,000 to 2,000 subscribers per week
“It still grows a thousand to 2000 people a week, the newsletter, but a thousand to 2000 people a week is a lot different when you're at 40,000 versus 80,000.”
McCormick: I will not raise outside venture capital for Not Boring
“I think I don't want to raise money because then I'd have bosses and I don't think I'd get a valuation that I'd be happy to sell part of myself for.”