Insight
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 …”
Insight
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 …”
Insight
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 …”
Insight
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…”
Insight
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.”
Insight
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, …”
Assertion Not checkable as stated
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.”
Insight
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.”
Assertion Contradicted
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.”
Insight
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,…”
Insight
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…”
Insight
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.”
Insight
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.”
Insight
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…”
Insight
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.”
Insight
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.”
Prediction Not checkable as stated
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 …”
Opinion
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.”
What-if
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…”
Insight
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.”
Opinion
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.”
Assertion Not checkable as stated
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…”
Insight
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.”
Assertion Supported
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…”