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 190 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 3 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
Wilkinson: Rolling Out Existing AI and Self-Driving Would Eliminate 20% of Jobs
“So if we just paused AI, we shut down all the AI labs and all we focused on was just rollout of what already exists. I think probably Between self-driving cars and AI agents, 20% of all current jobs are gone.”
Wilkinson: Software will commoditize as AI eliminates coding barriers
“And so my belief is basically that as more and more people don't need to learn how to code and can build software, software will become more and more commoditized. There'll be way more competition and it'll be a way harder world for software businesses.”
Wilkinson: Angel Investing Is Roulette, Not Poker
“I think of it as roulette. And I think like this period that we're talking about was about me learning how to play poker, right? Poker has way better odds than roulette. If you're good at poker, you can actually win. You've got, you know, a 60% odds. When you …”
Wilkinson: True value creation by Chamath Palihapitiya won't be clear for decades
“Chamath, we won't know if Chamath has actually built value for another 10 or 20 years. And frankly, like his, it's all very like secret. Cause I think a lot of his stuff is private. So we really have no clue how much money he has, how much money he made what's…”
Venture Capital Investing Is Totally Random and Functions Like Roulette
“I still think ventures totally random. I do it for fun off the side of my desk.”
Tech salary inflation will reverse as remote hiring shifts overseas
“I think that this high salary inflation is not here to stay. I think what's happened is all these companies down in San Francisco are going, oh, crazy. We can hire cheap people in Canada, but they're not yet going, oh, hey, we can hire people in India and the …”
Wilkinson: Claude Saved $100K Annually in Taxes Across Holding Companies
“I actually saved a 100,000 dollars a year of cash taxes by moving an investment from one hold code to another thanks to Claude”
Wilkinson: Indistinguishable 4K Video AI Coworkers on Zoom Within 24-36 Months
“I think that within 24 to 36 months, these will be four K video people that are indistinguishable, indistinguishable from a human that you'll talk to on zoom.”
Wilkinson Has Invested $25M to $30M Into Venture Startups
“And so I think I have like. 25 or thirty million dollars of venture.”
Wilkinson: Boring $2M Cash-Flow Businesses Beat Venture-Backed Startups
“Look, if you just started a boring business, like a trash hauling business or window cleaning business or whatever it is, You got it to one or two million dollars of cashflow, sell it or hold it. You're set for life. And instead they go off and they raise all …”
Wilkinson: Andrew Huberman's Media Business Is Completely Undisruptible
“His business, I'm like, that is a completely undisruptible business unless he gets hit by a bus or something.”
Wilkinson: Tiny forces AR discipline by leaving companies with two weeks' cash
“Chris, Chris and I, we used to leave two weeks expenses in the business. If it meant that if they don't collect their AR, their accounts receivable, they go off a cliff. Now, what they don't know is they're not going to go off a cliff because Tiny, the bank, w…”
Wilkinson: Buying Cash-Flowing Businesses Beats Venture Capital
“I think that I'm much better off incubating businesses and buying businesses. Cause it's a very steady, 15 to 30% cash return. And I feel it. I feel the wind in a much bigger way.”
Wilkinson: Ackman exited his short position before his viral CNBC interview
“If you actually look at the timeline, he'd already sold out of that position when he went on CNBC.”
Tesla's Competitive Advantage Is Overestimated Due to Apple and Google Software
“I just think that everyone overestimated their competitive advantage. And then at the end of the day, you've got all these legacy manufacturers and, you know, ultimately if Apple and Google are providing the interface that most people use, it barely matters, r…”
Market Panic Will Let Cash Buyers Acquire Businesses at 20-30% Yields
“You're about to enter an environment where anyone with cash who has a large sum of cash is going to be able to buy a business at say a 20 or a 30% earnings yield, meaning you can buy a business and pay yourself back in two or three years, maybe five years, and…”
SaaS Founders Can Hedge Concentration Risk by Shorting Public Competitors
“Let's say that you own a SaaS business. And your entire net worth is in the SaaS business and you currently you know, you've raised money at 20 times revenue or something. You might want to find a SaaS business that's publicly traded, that is a comp to you. An…”
Smart Investors Should Rent Homes and Put Their Capital Into Equities
“If someone's completely, if they're not an investor at all, then sure, go buy a house all day, whatever. It's a reasonably okay investment. But if you're even remotely smart and you know how to read and you go and read investing books and stuff, I think it's c…”
Wilkinson: Extreme entrepreneurial success requires a personality disorder or trauma
“I think in order to be that successful, you have to have some kind of personality disorder. Or like trauma or something, and you look at Musk or Bezos, or if you read more about Bezos, I think he's a really difficult person to work for.”
Wilkinson: Closing a $100M+ acquisition was simpler than a $1M deal
“We just did our biggest deal ever. And it was over a hundred million dollars and it was no more work or complexity than doing a one million dollar deal. And in fact, It was simpler than a one million dollar deal. Cause it's just a better business with a better…”
Wilkinson: Tiny stopped monthly CEO reporting; involvement harms portfolio performance
“We just did this a tiny, we changed, we don't get monthly reports anymore from the CEOs. So like there's businesses where I don't, I haven't even talked to the CEO for like three or four months. I don't even know what their numbers are. And what we've realized…”
Wilkinson: First-time founders are raising at $40M valuations with just ideas
“I've seen companies of with a founder, who's a first time founder, With an idea and they're raising it a forty million dollar pre valuation, right?”
Wilkinson: How billionaire-backed Asana crushed his bootstrapped startup Flow
“The story was basically, we started productivity software called Flow. I decided to bootstrap it like Basecamp. And we had a big competitor, Asana. And Asana was run by a billionaire, the co-founder of Facebook. He raised a shitload of money. And originally I …”
Wilkinson: Targeting Billionaire Status Is a Mistake and an Overreach
“I think overshooting is a mistake that a lot of people make myself included. And I think they think, okay, I need to be a billionaire or be worth hundreds of millions of dollars when in reality that is overdoing it.”
Wilkinson: Wealth creates a lose-lose social dynamic when dining bills arrive
“There's this weird dynamic that happens where when the bill comes, if you pay the bill, you're showing off, or you're implying they can't afford it, and if you don't pay the bill, you're an asshole because you can afford to, and so that's why we do that.”
Wilkinson: E-commerce businesses are the thin-margin online equivalent of retail bakeries
“E-commerce businesses are bakeries in my opinion.”
Wilkinson: Hired CEOs will always spend excess cash because incentives are misaligned
“If you ask the dinner guests, what's for dinner, they will always say steak. And I was like, oh my God, that's so true. Right. It's like, why wouldn't they, you know, it's not their money. They, you know, yes. Don't get me wrong. Like a CEO is incentivized for…”
Wilkinson: Public reputation drives M&A deal flow far better than cold outreach
“We've realized that, like, cold outreach is not the way to go. Like, we would much rather go and have a public presence and a reputation and have people actually seek us out and say, hey, I want to sell you my company.”
Wilkinson: Issuing frequent non-binding LOIs establishes serious M&A deal traction
“We throw out LOIs constantly. Like I have no qualms about that. They're not binding documents. You know, we'll send someone an offer and there's something about if I read an email and I say, Hey, I'll offer you two million dollars for your business. I don't th…”
Wilkinson: Dr. Peter Attia's private practice costs hundreds of thousands to join
“Well, I think it's, so it's a lot of money, obviously it's hundreds of thousands of dollars.”
Wilkinson: High work pace is innate and cannot be coached into employees
“I've never hired someone who doesn't have high pace. And then coached them into having high pace, right? People either do or they don't.”
Wilkinson: Distressed acquisition Girlboss generates its purchase price in annual profit
“Basically now the business is, I won't say numbers, but it's making as much as we paid for it every year in profit. And I think it's probably five or 10 X more valuable than what we paid for it at least.”
Wilkinson: Major AI competitors to GPT-3 will emerge within six months
“There's going to be a lot of. A lot of other players in that space coming out over the next probably three to six months. And that it will be, there's going to be an ecosystem of offering similar to AWS and Azure and Google cloud. I think it'll be the same thi…”
Wilkinson: Chamath stopped comparing Social Capital to Berkshire after underperforming
“In his annual shareholder letters, he would he would compare himself to Berkshire Hathaway. So he would track social capital's results versus Berkshire. And then one year he just stopped. And I think it was the one year that he didn't actually beat them. I thi…”
Wilkinson: Spreadsheet Investors Underestimate Operational Execution and Organizational Change
“One of the big problems with investors these days is they're often what I call spreadsheet investors. They look at a business like a spreadsheet and they go, oh, it's easy. We'll just increase margin by 20%. Not realizing that in order to do that, you have to …”
Wilkinson: BlackRock does not build value compared to Warren Buffett
“BlackRock doesn't build value. They just index. They own a bunch of pieces of paper. Warren Buffett actually grows stuff.”
Wilkinson: Charlie Munger admitted he cannot talk CEOs out of their ideas
“Chris and I had dinner with Charlie Munger a couple of years ago, and we asked him how involved do you get with the CEOs? And he really said I'll never forget this. He goes, I've never been able to change someone's mind. If someone has an idea about something …”
Wilkinson: A high-volume, low-ACV customer base beats concentrated enterprise revenue
“I always think it's better to have 10,000 people paying you a small amount of money than a hundred people paying you a lot of money.”
Wilkinson: Holding declining businesses beats selling for 1x profit
“Let's say the business is on a major downslope. You might get like one times profit. And so you're basically making a bet that it's going to die before a year, which very few businesses die that quickly. And so usually it's better off just to hold forever.”
Wilkinson: Bitcoin is currency trading and speculation, not productive business investing
“And I think that Bitcoin is currency trading, right? Like just buy great businesses, do the thing, you know, and I think everyone is just speculating on this stuff and there's a ton of fascinating arguments for it and I follow it, but I have just fully steered…”
Wilkinson claims the Canadian stock market is plagued by rampant fraud
“In, in the Canadian stock market, there's tons of fraud and there's very little enforcement and”
Wilkinson: Supercast valuation was cut 50% after missing revenue milestone
“We raised at a ten million dollar valuation, which at the time was kind of a good you know, angel, angel round valuation, but it was structured so that within two years, if the business doesn't do a million dollars of revenue, that turns into a five million do…”
Wilkinson: VC incentives push viable small companies into futile failure
“What I've seen is the incentive creates this situation where the founder is sitting on a business that could make them happy and give them a great lifestyle, but they have a gun to their head. And so they continue down the venture path, even when it's actually…”
Wilkinson: Raising from retail investors at inflated valuations is unethical
“I have a fundamental problem with taking money from someone when I know I can't give them a return or there's like a five percent chance and positioning it as, you know, you're investing in this super solid, awesome thing.”
Wilkinson: Guaranteed VC management fees will disappear in the long term
“And so I think this is something that will go away in the longterm.”
Tiny Bought $500,000 in S&P 500 Put Options in February 2020
“And so what we did is we basically said, okay, in late February, we said, okay, if this, if the S and P 500, the index of the 500 largest companies in America goes down by 20%, we will get a big payout. And so we bought for 500,000 dollars, put options that we…”
Tiny Lost $6.5M Reinvesting Pandemic Hedge Profits When the Fed Intervened
“And so we take all the money except for 500 grand. We took 500 grand out. We took all the money and we re-bet it and we lost everything because the Fed came in and the markets rebounded.”
Wilkinson Uses Interest-Only Mortgages to Keep His Capital in Operating Businesses
“I hate real estate so much that I don't build equity in my own houses. So I do interest only mortgages because I want everything in businesses because businesses, a business can earn a million dollars of revenue and then the next year do a hundred million doll…”