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 46 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 2 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
In media, a smart point of view beats long-term correctness
“It's more important that we have a smart point of view than that we're right in the long term.”
Google's ad dominance stems from DoubleClick capturing early international market share
“And that is the reason today, 25 years later that, you know Google still has a commanding share because we got it early on and it's never been given up.”
Henry Blodget did nothing legally wrong during Wall Street research scandals
“And so legally, I don't think he did anything wrong. Everything he wrote was approved by his superiors and order.”
Core consumer problems in e-commerce have already been solved
“So one of the reasons I do almost nothing in e-commerce these days is because I don't see the problem. We solved, the industry solved the problem. Meaning if you name anything on the planet earth, just about, you know, you can find a site. They'll have 10,000 …”
MongoDB lost $1 billion before becoming profitable, now earns $300M yearly
“I mean, Mongo, between being a private and public company, raised and lost a billion dollars before they had a profitable quarter. And now already make three hundred million dollars a year in profits.”
MongoDB will reach a $50 billion valuation within 10 years
“So that's why it's so valuable is because it's an, it's just an incredible company growing quickly, enormous market share, and is going to grow for the next 10 years. It'll be a fifty billion dollar company.”
DoubleClick expanded to 25 countries before operations became profitable anywhere
“So double case, the perfect example, we expanded to 25 countries before our first country was profitable.”
Business Insider reached 300 million unique visitors with zero ad spend
“What I'm proudest of is that Business Insider is at three hundred million uniques today and never spent one dollar in advertising.”
BuzzFeed failed to build a durable daily brand compared to Business Insider
“I don't believe they built up a true brand. They showed up in search results, they got traffic, but there were many, many people that religiously read Business Insider every single day. So it just had a brand that I think was much stronger and more defined.”
Infrastructure software like MongoDB requires up to $100M and cannot be bootstrapped
“Like Mongo, you got to take years to build a good enough product, and there's no way to bootstrap that. You know, it takes 20, 50, you know, there's a hundred million dollars generally for those types of companies to get there.”
Short-term AI utility is mundane workflow optimization, not true standalone companies
“The real use of AI in the short term is going to be much more mundane. It's optimizing customer support, you know, making your coding more efficient, things like that. We're a long ways before, you know, true AI companies are coming”
Some AlleyCorp portfolio companies cut 30% of staff recently
“And I have companies right now that we've cut 30% of the people in the last year because given this market and what they were doing, we had too many people.”
Any good business idea is independently conceived by competitors within six months
“You know, any good idea I'd come up with, eventually, even six months later, three other people are going to come up with the same idea. So you need to move quickly.”
Founders systematically underestimate the risk of inaction
“People tend to, they, most people understand the risk of doing something. They understate the risk of not doing something.”
The Wall Street Journal did not update its website intraday in 2007
“The Wall Street Journal and Businessweek at the time did not, basically did not update their websites during the day.”
Henry Blodget's lack of newsroom experience was a strength for Business Insider
“He had never really worked in a newsroom, which can be viewed as a weakness. I viewed it as a strength, and so he changed the rules, and we were willing to do that, and he did an incredible job.”
Ryan: Founders must act as coaches recruiting top talent, not players
“You got to think of yourself as you are the coach. You are not the player. And if you're a coach and if you manage to persuade, you know, LeBron James and Kevin Garnett and a bunch of people on your team, your team's going to do well. That's actually the job.”
Betting on one-year trends is too late; founders must target ten-year shifts
“Where is the world going to be in 10 years? That's the North Star for what we're doing. If something's gonna happen next year, it's too late. I need to bet on a ten-year trend.”
Six months and 100 interviews unlocks viable startup ideas in any industry
“I'm a bigger and bigger believer now of industry focus. You know, it's a, you know, you and I are not going to think of something that applies to the chemical industry right now. But if that's all you did for six months and interviewed a hundred people, you'd …”
Rising labor costs will drive inevitable business automation
“The cost of labor is going to just keep going up. And so, you know, waiters were paid 15 dollars an hour. Now it's 20 to 25 dollars an hour in New York. Unless we change immigration or something fundamentally changes, that could be 30 dollars an hour. So you k…”
AlleyCorp backed a teleoperated vehicle company to bypass autonomous driving regulations
“Another company we invested in is, so driverless cars is, as you know, not legal in most countries, most states, but having a remote driver is.”
The vast majority of unicorns are product businesses, not services
“The vast majority of quite successful companies are in that category. The services oriented companies, you know, it's harder to get to be a unicorn. It can happen, but there aren't that many.”
AlleyCorp avoided early-stage AI startup investments in 2023 due to irrational pricing
“Six months ago, you know, the pricing on AI was insane. You know, three people walk in and say we're worth a hundred million dollars because we're going to put together an AI company. Just didn't make sense. So we didn't make any direct investments there.”
Ryan: Founders cannot successfully be CEO of multiple companies simultaneously
“You know, you can't truly be CEO of multiple companies, but you can be chairman of multiple companies, but you got to start with one. And if you try and do two or three at the same time on your own, it's not going to work.”
Kevin Ryan instructs his marketing team to keep him unrecognized in public
“No, the people are on my marketing team know that the goal is that we are very successful. And that when I walk into a restaurant, no one knows who I am.”
Kevin Ryan has personally invested $250 million into AlleyCorp's startups
“I've invested probably two hundred fifty million dollars into the various companies over the years.”
Business Insider sold to Axel Springer for 11x its $40 million revenue
“We were doing forty million at the time. We sold it for 11 times revenues, which is a big, big number for immediate properties.”
Kevin Ryan: Emotional Detachment from Board Chairs Is Essential for M&A and Strategy
“I think it's important to not get too emotional about any one company. And that's one of the things I can bring to the table. When you're CEO, you're just so close to it. You're in the forest. I can step back a little bit and sometimes say, look, you know, thi…”
DoubleClick cut staff as 70% of clients went bankrupt in dot-com crash
“Then we spent three years bringing back to a thousand people as the internet collapsed and 70% of our clients went bankrupt.”
Gilt Groupe sold for $250 million
“We sold for two hundred fifty million, which was less than we thought, but it's Still obviously a, you know, a real number.”
AlleyCorp invests $1.5 million to launch each new startup
“So we started each company with a million dollars. So 500,000 from each one of us. And that was for Gilt, Business Insider and Mongo. And then we, I did after that Dwight semi-retired. And so I did that with Nomad. I did that with Zola. And now, by now I put a…”
Kevin Ryan chairs 12 AlleyCorp companies, spending half his time guiding them
“So I chair 12 companies. So about half my time is spent focusing on those 12, which are 12 of our most valuable companies to really guide them and make sure that they do as well as possible.”
Kevin Ryan is the leading funder of Yale's psychedelic research center
“I'm the leading funder of the Yale Center for Psychedelic Research.”
Transcend Therapeutics raised $40 million at an $80 million pre-money valuation
“Because we started off with a million and a half dollars, but we raised forty million dollars about a year to a year and a half later in two tranches at eighty million free.”
Transcend Therapeutics secured a patent for mental health compound methylone
“If you follow this industry, you know that you can't patent MDMA or mushrooms because those have been around for a long time, but we actually did get a patent for methylone, which is the compound that we're working on.”
AlleyCorp holds a $50 million position in Transcend off $5 million invested
“Now there's still risk, but that company is, you know, we currently have a fifty million dollar position based on our five million that we've invested so far, and we think it has a lot of potential.”
MongoDB is approaching a $2 billion revenue run rate
“Then finally, Sequoia came in and then we raised a lot of money and now it does getting close to a two billion dollar run rate.”
AlleyCorp operates an in-house 70-engineer firm and executive search agency
“I have 70 engineers who work for me. I have my own in-house outsourced engineering company, which helps us build product now very quickly, which we've had the last three years. I own a big chunk of a search firm, a 10 person executive search firm that we set u…”
The assisted fertility sector will continue growing over the next 10 years
“That's going to grow for the next 10 years for all the reasons we know about people having children later, sperm counts are down, a bunch of things.”
AlleyCorp backed a robotic massage startup to fill a 17,000-therapist shortage
“We're an investor in a company that gives robotic massages. There's 17,000 open positions for massage therapists in this country. And so, you know, there's hotels that just can't offer massages because they don't have the people.”
Kevin Ryan seriously considered running for Mayor of New York City
“I did Think about running for mayor, you know, eight years ago. I've been very involved in politics in many ways representing tech community and in every dimension. All my life, I thought I would want to, that'd be the one other thing I'd want to do. And then …”
AlleyCorp operates as a single-LP fund where all employees receive carry
“I'm purely just investing my own money, but I have all infrastructure and a whole firm that does that. So it's like, it has historically been a single LP fund. Everyone has carry. It's no different than you and Square Ventures or Thrive or anything else. Just …”
Kevin Ryan invests 90% of his net worth in private companies
“All in on private companies. So probably 90% of my net worth is just in my own farm in, in investing in various companies and things. I have a li, I have some in, in some VC and private equity firms, you know, as an LP. You know, and I do have some real estate…”