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 189 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 1 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
Caldwell: Ex-Google executives join early startups because they underperformed or misunderstood reality
“What usually happens is they either are, either they joined your startup because they're, they weren't doing well. I'm trying to think of a nice way to say it. Either there's a reason they joined your startup and left Google, or they had expectations that you …”
Caldwell warns that overly friendly industry networkers are often highly exploitative
“A lot of the folks who are most approachable when you are a first timer, or when you're just moving to the area, or you're trying to break into the industry, the friendly people that want to talk to you are often
The most exploitative, and they're the people …”
Caldwell: Starting a company by pitching VCs invites exploitation
“If your idea for how you start a startup is to first create a pitch deck and go pitch VCs, you're setting yourself up to get screwed. You're setting yourself up to get taken advantage of by people who are gonna have 20 different ways to rip you off, versus if …”
Caldwell: Predatory service providers systematically target and exploit struggling startup founders
“We see this a lot with struggling startups. All sorts of people will come out of the woodwork to sell you services or promise they'll connect you with the investors or they'll help you fundraise or you name it. And it's like, it's kind of like moving to Hollyw…”
Caldwell: Effectively no startup gets acqui-hired after running out of runway
“No one gets acquired effectively. Like there's an asterisk next to no one. But the companies, of the companies that attempt, when they're lower on runway, they're, they flew the plane into the side of the mountain. There's no acquisition coming, man.”
Founders carry startup failure forever while venture investors quickly move on
“This is what's so weird about this business is like, who has to live with the rest of their lives that that was their startup. Or that they could have done something different. They weren't able to versus the investors like, yeah, whatever. Cool. And they go, …”
Caldwell: Many ex-Facebook employees feel they made money doing evil
“Yeah, like, I know a lot of ex-Facebook people who kind of, like, feel that they did evil, and they made money doing it, and they seem pretty unhappy about it. They're not happy about the work that they did in the universe.”
Caldwell: If Elon Musk overthought, he would have abandoned his companies
“And if he was an overthinker, he would do, he would rule all the stuff out. All the stuff is like, obviously a bad idea. And anyone in the Midwit territory would rule out all these ideas.”
Caldwell: Consumer startups make up only about 5% of YC's portfolio
“People think that YC funds consumer companies, and this is what our bread and butter is. And like, Yeah, like, I think it's like five percent consumer.”
Caldwell: Conditional Commitments Are a 'Cheap Shot' Founders Despise
“So one thing that we hear a lot of, especially for folks that haven't done much of this, is they say, okay, I'm in, once you go find the rest of the round. And this is the cheapest of cheap shots that you can possibly do because what you're actually saying is,…”
Caldwell: Market Trend Forecasting Is Flawed for Decade-Long Startup Horizons
“When we make an investment, often it does not become a big company for at least 10 years. And so, if you're trying to do market analysis and market trends for an investment that won't become big for a decade later, it's kind of flawed analysis versus if you're…”
Caldwell: Startup classes teach investor analysis instead of zero-to-one execution
“Startup classes. And they tend to be taught by non-founders. They tend to be taught by investors. And a lot of what you learn is about how to pitch, how to do market analysis, how to identify ideas via market trends.”
Caldwell: Later-stage VC is about finding traction, not predicting unproven winners
“What do I think great investors do, especially later stage than what Y Combinator is, it's they find companies that have product market fit that are taking off, that have incredible traction, and they try to find them and invest in them, and that's the job.”
Former PMs fail at early sales by relying on user research tactics
“I think that a lot of people are trained as PMs and they're trained to do user research. And being trained to do user research, I remember taking a user research course in college, is you're trained to sort of like interview people rather than sell products to…”
Founders with average skills but high conviction often succeed
“Eh, not the best programmer, not the best salesperson, not the best fundraiser, but very high conviction and able to focus their energy one direction in a superhuman way. Those people tend to succeed.”
Caldwell: Daily News Consumption Bombards Audiences With Tech Negativity
“If all you do is read the news every day, You get bombarded with negativity, especially around technology. There's a lot of, the biggest technology stories right now are some version of, like, This is bad. These people are bad.”
Caldwell: Future generations will view human-driven cars as barbaric
“And the number of people that every day get seriously injured or die in car accidents, I think we're going to look back and be like, that was crazy barbaric. That was like having surgeons that didn't wash their hands. In that era. Is I think how we'll look at …”
Caldwell: Software startups without software co-founders are not in the stadium
“If you're saying, yeah, I'm gonna build a software company. And you don't have a software co-founder, it just, you're not even in the ball game. You're not even in the stadium.”
Caldwell: DoorDash and Airbnb would have failed using outsourced dev shops
“But I think if you just look at the facts of the companies we funded, like literally DoorDash or literally Airbnb or any of these folks, they lived and died by their speed of shipping software. And if they, what they did was buy white label software or have so…”
Caldwell warns having equal equity means sharing blame when startups fail.
“If you have equal equity with someone and you have a seat at the table in decision making, just because it's not working doesn't mean you get the right to blame other people.”
Caldwell: Startups Do Not Need to Be in SF to Succeed
“I don't think everyone's startup needs to be in San Francisco to be successful. And that you could build a successful startup and not live in San Francisco.”
Caldwell: Few Top Tech Companies Were Built in SF Proper
“And so clearly in the history of this stuff, all these great companies were built outside of San Francisco. Like if we actually look, how many of the most epic companies in the world in tech were actually built in San Francisco? It's actually not that many. An…”
Caldwell: Founders Outside Hubs Don't Realize What They Miss
“And basically, what's weird about network effects is if you're not Benefiting from them. You don't know what you are missing.”
Caldwell: YC accepts startups with $500K ARR or $1M+ raised
“We have folks that get into YC that have, I don't know, half a million dollars in annual recurring revenue. Also a common one here these days is, oh, I'm too far along because I've already raised some money. We have folks that apply and get accepted to YC that…”
Caldwell: Most founders in recent YC batches are repeat applicants
“And the fact is, most of the folks in the most recent YC batches are not first-time applicants. There's some folks that applied five times, six times, seven times.”
Caldwell: Technical founding teams have 5x higher odds of a YC interview
“So if there is a team that's applying where at least one of the founders is at a skill set level to be hired into a technical role at a top YC company, they have five X better odds than teams that don't.”
Caldwell: YC is designed to fund strangers without warm intros or decks
“The entire YC model was built to not require networking. We don't want warm intros. We don't want pitch decks. We don't want to hop on a quick call. That is not how YC works in our funding decisions. We built a system that is optimized for funding complete str…”
Caldwell: Playing the credential game beats rejecting the academic system
“To the extent you can learn to work, to understand the rules of the game, and play the game with credentials, and realize that leveling up on the credential game will help you with your long-term goals. I think that's much better than like, rejecting the syste…”
Caldwell: Founders Angel Investing Alienate Employees and Strain Capital
“The prizes that you win playing the game is congratulations. Now a bunch of your money is tied up in illiquid investments that may or may not show up. So now maybe you're like financially strapped. Maybe you're worried about other stuff. You're worried about y…”
Caldwell: People with strongest opinions on YC never did a batch
“I think another big misconception was just folks, a lot of folks that apparently have the strongest opinions of telling people about YC never actually were in a batch.”
Caldwell: Non-Technical Founders Who Have Shipped Nothing Are Overly Optimistic
“If you can't build a product and you don't have a tech co-founder or whatever, or you have never once built a product and given it to anyone and you think it's going well, you are too optimistic. Like it's not going well, like, sorry.”
Caldwell: Tech workers and founders are moving back to SF and NYC
“I think a lot of folks are moving back right now. New York too. It just seems like people are going back to the big centers because they're getting bored and lonely and feel kind of over it.”
Caldwell: Downturns are ideal times for low-burn underdogs to attack high-burn rivals
“Cause again, for some folks, the actual move is to go on offense, right? Just like we said a moment ago where they're like, okay, I see. So this is the score. Got it. Time to go hard against my competitors who are have higher burn. Yeah. You know, like this is…”
Caldwell: Outside venture capitalists get angry at YC for empowering founders
“And it's just funny how like doing that really seems to annoy investors that we're like, again, we're like giving away We're like on the wrong team a lot. They seem really mad at us.”
Caldwell: Portfolio math incentivizes VCs to push startups toward explosive outcomes
“It actually makes sense from a portfolio theory to advise people to do this because either way, either it works great or it dies and goes away and you get to spend your time on something else, but like either way it's explosive, right?”
Caldwell: Fast raised $100M and burned it in 10 months
“What did fast do? They raised a hundred million and they burned it in 10 months. They got into a ten million A month burn.”
Caldwell: Most FAANG engineers secretly work on trivial tasks and ad servers
“Most people that get most jobs at Fangs, when you talk to them after they have the job, if they're, you know, get a couple of beers in them, they're working on some bullshit ad server. They're working on like one pixel on one corner of one thing. They're worki…”
Caldwell: FAANG engineers mostly learn proprietary tools useless for early startups
“A lot of what you learn is how to use the tools of the FAANG, which you don't get to use when you don't work there anymore.”
Caldwell: Spending too much time at FAANG becomes a negative VC signal
“But I think at some point, the more time you spend there, what was once a good positive signal could turn into a negative one. Again, I can't speak for all investors, but at some point you lose the shininess of getting that validation as well as what team you'…”
Caldwell: Cycling through startup mentorship programs is a massive time suck
“I'm not saying like it's all bad, but it's a bottomless pit of time suck. Like you could go so far deep in there. You could be in that bottomless pit for years and be a startup founder that's never built a product and has never gotten a single customer because…”
Caldwell: Naive founders benefit because failure risks never occur to them
“The beauty of not knowing anything is that you think everything is easy, and none of the innumerable reasons why something might be hard or your startup might fail even occurs to you.”
Caldwell: Filing patents for early IP is a classic overthinking mistake
“Michael, should I file patents for all of my IP? Exactly. That's a classic overthinking thing. Probably not.”
Caldwell: The genius startup strategy is asking what an idiot would do
“The beauty of the midwit meme is the genius and the idiot come to the same conclusion. So what is the idiot approach? Like that's actually how you can define the genius approach is you're like, what would an idiot do?”
Caldwell says founders prioritize financial engineering and treat product as an afterthought
“Too many founders treat product as an afterthought. They're basically trying to do financial engineering, and the product is like delegated.”
Caldwell says non-tech investors often demand crazy terms and operational control
“If someone made all their money investing in real estate or in strip malls or franchise McDonald's franchises or something like just something that is not remotely a tech startup, they will often ask for crazy terms that would make sense if they were investing…”
Caldwell says junior VC associates push fundraising to show quick valuation markups
“Their KPI is that if you raise money and they can mark up their investment, it makes them look good. So they can go tell their colleagues or their investors, Hey, I invested in this company and it went on to raise more money at a better valuation than I invest…”
Caldwell says young investors just regurgitate trends from VC Twitter and essays
“I think you kind of see this from these investors where they just, they read what other investors say and do, and they sort of like say and do whatever it is they read. And so like, whatever the hot new trend is, whatever people are tweeting about, whatever, l…”