Dalton Caldwell
Co-Founder & General Partner, Standard Capital. On 2 shows, 33 appearances. The Shows tab opens the full record on each.
investorfounderhostexecutive@daltonc ↗LinkedIn ↗daltoncaldwell.com ↗Wikipedia ↗
Caldwell co-founded digital music platform imeem and subscription social network App.net. Over more than a decade at Y Combinator, he advised over 1,000 startups before co-founding early-stage investment firm Standard Capital.
2shows
33appearances
221statements
19resolved
16supported
2contradicted
84%fully supported
13said about them ↓ Everything Dalton Caldwell said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Caldwell: Instagram was a free knockoff of Hipstamatic combined with a social graph
“And so they basically built a pretty legitimate knockoff of the Hipstamatic filters, combining it with a social graph and they launched it and it pretty quickly took off. So of course this is Instagram.”
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: Successful startup founders rationally should have quit at some point
“If you look at all the startup stories that we have at YC and all the companies we funded over all the years, the underlying theme is that rationally the founder should have given up at some point.”
Caldwell: Startup success requires irrational persistence through multiple near-death experiences
“Across the portfolio of YC and non YC companies, there has to be this irrational, you know, intention to keep going even when the world tells you it's not working and you feel completely defeated. And you likely have to go through this many times and have thes…”
Caldwell: Rigorous TAM calculations at the earliest stages are misleading
“The earlier you go, the less it matters. And some of the most phenomenally good startups, if you were really pedantic about it, the TAM would be like tiny. Like the TAM of Uber would be like nothing, right? Like how the TAM of Airbnb would have been nothing.”
Caldwell: Investor pressure to hire big-tech executives often leads to startup failure
“You get pushed often by investors to hire executives or to scale the team, or we need, you know, We need, we re you raise all this money. You got to spend it. You know, we got to, you got to show you're serious about growth and building a world-class organizat…”
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: Brex and Retool appeared to be their YC batch's worst startups
“Vyond Change their idea and got really excited about it and renamed to Brex. And this was Brex, which is like a Decacorn. And Cashew changed their idea and renamed to something called Retool. And so out of my 35 companies, the ones that objectively seemed the …”
Caldwell: Successful pivots move closer to founder expertise and prior learnings
“Usually a successful pivot gets warmer instead of colder from what you're an expert at and somehow builds on what you learned on the prior idea.”
Caldwell: Founders can find big markets by targeting hated enterprise incumbents
“My suggestion was to start by looking at what companies are publicly traded and or owned by private equity that are large and that also are hated by their customers. And to try to intentionally find where there's a knowable big market within a comment. Combine…”
Caldwell: Tar pit startup ideas generate positive feedback and persuasive arguments
“The weird aspect of what we call a tar pit idea is an idea that a lot of people come up with, and then it seems like an unsolved problem and you get lots of positive feedback for, right? And you have a really good set of arguments that it's a really good start…”
Caldwell: Founders use landing pages and ads to avoid awkward customer conversations
“And I think a lot of folks, their inclinations are to like, you know, build a landing page and buy some Instagram ads and try to get people to sign up for something. And again, maybe I, maybe that's something, but I think a lot of the reason people do that is …”
Caldwell: Founders should spend 20% to 30% of their time on customer calls
“I think it's look at your calendar and there should be, you know, 20 or 30% of your time that the calendar says something like customer Meeting, customer call, like meeting with foo, meeting with this person. And when the calendar is not that, or it's all, you…”
Caldwell: Andreessen Horowitz passed on Instagram due to a conflict with Picplz
“And basically because Andreessen Horowitz had like invested in my company was on the board, even though they were investors in Instagram That was like a conflict and they didn't do the deal.”
Caldwell: Growth hacking and A/B testing waste time for early startups
“I think growth and growth hacking and doing all this analytics, AB testing stuff is a total waste of time for very early startups.”
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…”
The other half of the tape: Dalton Caldwell's own voice is left out of every number here. Other people bring the name up 11 times in 6 episodes across the shows. 2 statements on the record name them. every mention, with the transcript →
Who brings them up most Jessica Livingston 4Geoff Ralston 3Kevin Hale 2Paul Buchheit 1Jared Friedman 1
Statements about Dalton Caldwell, by other people (2)
Seibel: Everyone who left the Bay Area during COVID returned
“You and I both saw a lot of people leave the Bay Area during COVID. All of them came back and they all said this.”
Ralston: Angel investors must lose money before becoming experts
“Meeting founders and making decisions is way more of an art than a science, and as Dalton says unfortunately in this game I think you have to Lose some money before you can really become an expert, as much as anyone is an expert at answering the questions you …”
Every mention by year
tap a year for its mentions
the Y Combinator Startup Podcast 7
Lenny's Podcast 4
2024 4 mentions in 1 episode
2022 1 mention in 1 episode
2019 2 mentions in 1 episode
One line per show, most statements first. The link opens Dalton's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| Y COMBINATORLEDGER | Co-Founder & General Partner, Standard Capitalhost | 32 | 189 | 82% 14/17 | full record on the Y Combinator Startup Podcast → |
| LENNY'S PODCASTLEDGER | Co-Founder & General Partner, Standard Capital | 1 | 32 | 100% 2/2 | full record on Lenny's Podcast → |