Dalton Caldwell
116 statements across 29 episodes · 27 bullish · 47 bearish · 3 people on the record · first statement Jul 1, 2017 by Dalton Caldwell · said 7 times in 5 episodes since 2018 · across every show →
On the record as a speaker too: Dalton Caldwell's record, appearances and statements → this page counts the times other people say the name.
Mentions by year
brought up most by Geoff Ralston (3), Kevin Hale (2), Paul Buchheit (1), Jared Friedman (1)
tap a year for its mentions
2022 1 mention in 1 episode
2019 2 mentions in 1 episode
Everything said about Dalton Caldwell, oldest first
Jul 1, 2017
Mar 7, 2018
Caldwell: Successful Angel Investments Demand a Ten-Year Liquidity Horizon
“Even the companies that go really well, we are talking about a 10 year time horizon. PB's about to talk, and like, you know, a lot of the investments that he made in 2008, 2007 are still hanging out there. He's getting no liquidity from it.”
Mar 7, 2018 negative
Mar 7, 2018
Caldwell: YC Urges Founders to Secure Wires Before Investors Flake
“We definitely encourage founders to get the money wired from the investor. We, every, there's so many sad stories that we know, where someone commits to invest and then disappears, or like never actually wires the money. And so we do encourage people to say, o…”
Mar 7, 2018 negative
Mar 7, 2018
Mar 7, 2018 positive
Caldwell: The Best Startup Investments Look Deeply Unappealing to Most
“Really good investments are often contrarian or unfashionable, or somehow are deeply unappealing to everybody else, right? Those are the really good ones, is that you see something that other folks don't, and that, that, the fact that it's deeply unappealing i…”
Mar 7, 2018
Mar 7, 2018 negative
Mar 7, 2018
Caldwell: YC Tracks Progress of Rejected Startups to Iterate Decisions
“We keep track of everything we fund. We keep track of things we don't fund. We track their progress. We keep track of who does really well and who doesn't do really well. And we take ample notes on everything. So we do a lot of reviewing our process, and we tr…”
Mar 7, 2018 positive
Mar 7, 2018 negative
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,…”
Mar 7, 2018
Caldwell: Founder Defensiveness About Competition Is a Major Red Flag
“Usually if the founder is super defensive and flips out about it, that is a good red flag for you, right? That is a very good red flag if the person has a very hard time Speaking on an even tone about competition, or is unwilling to admit the competition eithe…”
Mar 7, 2018 positive
Caldwell: Investors Should Treat Pitches as Job Interviews For Themselves
“In terms of bad meetings one thing to think about is pretend that the investor meeting is your job interview, where they're interviewing you for a job, and not the other way around. There's often a lot of power dynamic things of making it feel like the founder…”
Mar 7, 2018
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 …”
Feb 15, 2019
Feb 15, 2019
Caldwell: Investor hype is not predictive of startup success; retention and revenue are
“Excitement around the core product or feeling like other investors are excited about it and things like that definitely give a founder, like yourself, tons of leverage. But that I actually have learned to not take that too seriously as an investor, as a signal…”
Feb 15, 2019
Feb 15, 2019 neutral
Caldwell sometimes discourages profitable side projects from raising venture capital
“Sometimes what I do is actually discourage someone from doing venture financing if they have a side project working, especially if they're making money, And they never will have, like, they can support themselves on it, and they can basically have the job fore…”
Feb 15, 2019 neutral
Feb 15, 2019
Feb 15, 2019
Jan 5, 2022 neutral
Jan 5, 2022 negative
Jan 5, 2022 negative
Jan 26, 2022 positive
Caldwell: OpenSea spent two years grinding on a barely working, simple website
“OpenSea was in YC in 2018, and you know, it was a rough start. They changed their idea. They were working on something else to begin with, and they pivoted into OpenSea, and they actually spent something like a year to two years Grinding it out with this reall…”
Jan 26, 2022
Feb 2, 2022
Feb 23, 2022 negative
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…”
Feb 23, 2022
Caldwell says most startup failures come from getting zero customers, not fundraising
“What failure usually looks like for a lot of our companies is they get zero real customers. Zero. It's not that the failure was they couldn't get a Series A, it's that they just, like, bombed. Like, complete disaster.”
Feb 23, 2022 negative
Feb 23, 2022 negative
Caldwell says founders regret giving equity for celebrity influencer promotional posts
“Most of my experience, both personally and with founders NYC, is the founders kind of feel like they got a raw deal on these and that the clicks they get from the posts or whatever, Were not as helpful as they had hoped.”
Feb 23, 2022 negative
Mar 2, 2022 negative
Mar 2, 2022
Caldwell: People struggle to believe how silly successful startups were initially
“I think if you haven't seen really successful startup companies, either personally, like where you were the founder of one, or you know people and you saw them go through it. It's hard to believe how silly these things are when they start. Like, I think unless…”
Mar 2, 2022 negative
Mar 2, 2022
Mar 2, 2022 positive
Mar 2, 2022 neutral
Mar 2, 2022 positive
Mar 2, 2022 negative
Mar 2, 2022 negative
Mar 31, 2022 negative
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…”
Mar 31, 2022 positive
Caldwell: Startup sales requires uninterrupted maker blocks, not 20-minute slots
“What I've learned that I did not appreciate when I was a founder is that the maker schedule vibe works for sales and talking to customers too.
And it's scheduling, 20 minute blocks to talk to customers is not the same as an eight hour.
Like even if it's not li…”
Mar 31, 2022
Caldwell: Effective programming requires eight-hour uninterrupted blocks of maker time
“When you're programming, the more of the program you can keep in your head at any one time, The easier it is for you to know what's going on and have the context up here to make changes and fix bugs. And it takes like an hour or two cold of looking at a progra…”
Mar 31, 2022 positive
Caldwell: Successful founders keep live KPI dashboards on screen 24/7
“The number one thing that I do that
I realize that a lot of the other successful founders did too
Was I had my analytics dashboard or whatever was important KPIs on the business up on my screen, 24, seven, and I would stare at it all the time.”
Apr 20, 2022 negative
May 6, 2022 negative
May 6, 2022 positive
Caldwell: DoorDash succeeded despite high burn due to sophisticated tracking
“DoorDash, who I guess we always talk about, but you know, they were good at numbers and they understood default alive, default dead, and they understood burn, like very sophisticated. And so even though they were playing, they were flying the plane very close …”
May 6, 2022
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?”
May 6, 2022 negative
May 6, 2022 positive
May 6, 2022
Overhiring, rather than office perks, drives excessive startup burn rates
“Well, for most folks, it's literally headcount. It's not office snacks. I'm sorry. That's probably not the thing that's, you know, perks are not bankrupting the company. It's that you hire too many folks. People are expensive.”
Jun 8, 2022 positive
Jun 8, 2022 bullish
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…”
Jul 22, 2022 negative
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…”
Jul 22, 2022 negative
Caldwell: Founders can accumulate personal health debt for up to ten years
“At some point, no matter, it's almost like you're going into debt, like personal health debt or whatever you want to call it. And man, you can go pretty far into debt. You can go five years into debt. You can go 10 years into debt. I don't know. But at some po…”
Sep 1, 2022 negative
Sep 1, 2022 negative
Caldwell: Feeling smarter than others leads to morally rationalizing exploitation
“I think if you feel that you are smarter than other people, and this is something we encounter sometimes in our jobs, I think if you feel that you are more intelligent than others, perhaps you can end up on the slippery slope of moral arguments, that it's okay…”
Sep 9, 2022 positive
Caldwell: The Best Founders Master Cognitive Dissonance During Crises
“And I think the best founders Have techniques and they can do it. I think, and they can like be really good at it. I think something to aspire for is a founder is someone who can know both. Oh no. Like my star employee just quit and says my startup is horrible…”
Sep 9, 2022 bearish
Caldwell: A tech trend has peaked once it dominates YC applications
“You can tell when something has jumped the shark, when it is a, one of the more common ideas people apply with. Like, remember chatbots? Everyone was building a chatbot for a couple of years there, and that's when you knew it was over, basically.”
Sep 9, 2022 negative
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.”
Sep 9, 2022
Oct 28, 2022 neutral
Caldwell: Venture fundraising is not an efficient market and has distinct ecosystems
“Too many folks think fundraising is a market like the stock market. And that there's like graphs and charts you can have, and it all operates like an efficient market instead of what it actually is, which is like 10 different things, right, Michael? Like the Y…”
Oct 28, 2022 positive
Oct 28, 2022 negative
Caldwell: Founders do all the work, investors do not build companies
“The way you build a company is not, you're not baking a cake where you sprinkle in three different investors and then a cake pops out. Like, that's like the stupidest thing I've ever heard. This is a really common misconception out there, which is like, I hate…”
Jan 11, 2023 negative
Jan 11, 2023 neutral
Caldwell: Founders must acknowledge failure instead of weaving victim narratives
“If something doesn't work to accept it, to acknowledge it, to look at it, but realize you're the boss of yourself and you should just not feel a need to make a million excuses or have like create this long narrative where you're the victim and everyone else, i…”
Jan 11, 2023 negative
Jan 11, 2023 negative
Caldwell: Founders invent fake metrics to avoid measuring whether products work
“The actual meaning of the metric, which is to capture if it's working or not. You know, it's like every, every which way people are so creative in finding ways to like, not actually measure the thing that they know they're supposed to be measuring.”
Jan 11, 2023 negative
Caldwell: Founders spending all day on Twitter lose touch with real money
“If you spend all day on Twitter and discord and everything's a game and everything to joke, everything's silly, you can kind of, I just have noticed some folks lose themselves and not realize that the numbers in the spreadsheet are real dollars”
Jan 11, 2023 negative
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…”
Feb 5, 2023 neutral
Post-crash tech attracted genuine computer enthusiasts, not profit-seekers
“Like it was pretty much people that just liked computers would be my assessment had nothing to do with financial. Seeking financial gains. Cause again, if you do that, you do management consulting, you do, there's a bunch of other options. And so it was kind o…”
Feb 5, 2023 positive
Feb 5, 2023 neutral
Feb 5, 2023 negative
Obsession with startup drama and personalities signals that a founder is conformist
“It's just a sign of what you're focused on. And so when folks are really involved in the scene, in the drama, in the characters and are obsessed with the startup scene as opposed to their own thing and solving customer problems. That's usually a sign of like c…”
Feb 23, 2023 positive
Apr 14, 2023 positive
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…”
May 12, 2023
Caldwell: YC selection criteria explicitly weighs whether applicants follow directions
“Our entire application process has these detailed instructions, and we definitely take into account if you follow them in our selection criteria. This is one of the ways to tell How detail-oriented someone is if they just follow directions, and so pro tip, rea…”
May 12, 2023 neutral
Caldwell: Non-tech businesses lacking programming or biotech should not apply to YC
“If your business is not a technology startup, say it's more of a traditional business where there's no technical component, there's no programming, there's no biotechnology. That's probably a good reason not to apply. That's not really our sweet spot.”
Jun 30, 2023 positive
Jun 30, 2023 positive
Caldwell: Pre-Google conventional wisdom wrongly treated search as a commodity
“I think that the conventional wisdom pre-Google was that search was a commodity, and that Yahoo was good enough, and that incremental engineering breakthroughs in search wouldn't matter, and Google disproved that where it was actually a hard technical problem,…”
Jun 30, 2023 negative
Jun 30, 2023 negative
Caldwell: Founders flamed out by blindly copying WeWork and Zume Pizza
“Well, again, just to be super concrete, how many people do we see that were influenced by WeWork and building WeWork for X? And their entire strategy was based on WeWork. We saw the same thing. Zoom pizza. Like robotic pizza making. And so you'd see these thin…”
Jun 30, 2023
Aug 1, 2023 neutral
Aug 1, 2023 bearish
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…”
Aug 1, 2023 bullish
Nov 1, 2023 negative
Caldwell says exploited founders in YC applications are usually technical people.
“So this comes up a lot for us at YC where we read a lot of applications and we interview a lot of companies and we see folks where it's pretty clear what's going on. We can see it a mile away in the application that someone is getting exploited or ripped off a…”
Nov 1, 2023 neutral
Nov 1, 2023 negative
Caldwell says early technical employees doing co-founder work get hosed with 1%.
“Well, the early employee notoriously kind of gets hosed on this stuff, especially if they're providing the work of an equal technical co-founder, yet they get one percent or less of the company. Again, this is very common where you'll have two business founder…”
Nov 1, 2023 positive
Caldwell notes unequal founder equity splits are easily fixed when directly challenged.
“We see this with equity splits because often sometimes it'll just be, Hey, have you all thought about maybe like, or how did you come up with the equity splits? Like, well, it's, you know, 9010. Well, why? Well, it's my idea. Well, you know, most of the work i…”
Nov 1, 2023 negative
Caldwell warns excluding engineers from business meetings clearly signals exploitation.
“If you're trying to self-diagnose, am I being exploited as an engineer, as a technical person, is the whole point that the business people have a lot of meetings that you're not invited to, and all decisions about everything are made by the business people, an…”
Nov 1, 2023 positive
Nov 30, 2023 negative
Nov 30, 2023
Caldwell: Top engineers refuse to be worker bees for idea guys
“What often happens, again, to go deep on this, is that the way they'll pitch the person is they'll pitch them their idea. They'll be like, I'm an idea guy. I've got a great idea. Do you want to be my, like, worker bee to go do all my ideas? And of course the p…”
Nov 30, 2023 negative
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…”
Nov 30, 2023 negative
Dec 21, 2023 negative
Caldwell: Political tribalism causes people to dismiss technological progress
“I think when you're really caught up in the moment, everything gets polarized into political stuff or tribal warfare about who's on what team, and so if it's, if your team is the thing pushing for the thing, you celebrate it, but if the other team is, you know…”
Dec 21, 2023 positive
Caldwell: Optimism is more fruitful than cynicism for builders
“If you're actually building things and you want to be a part of creating it. It's much easier and more fruitful to be optimistic and think about all the things you can do and think about what you personally can do and what you can work on. Versus just being li…”
Dec 21, 2023 positive
Caldwell: Major Technological Shifts Only Become Obvious Decades Later
“The reason to enumerate this stuff is that in the moment when all this stuff was happening, it wasn't immediately obvious that the world was changing. It was just kind of normal, like, oh, this new thing came out. Oh, that's cool. And even at the time, some of…”
Dec 21, 2023 negative
Feb 29, 2024 negative
Founders must use their own products before trying to sell them
“You should at least be able to use your own tool. And be proud to use it or feel like it's providing some value, the V in the V, it's viable for you. And if you can't even get your, you can't bring yourself to use your own product. It's a little weird to be tr…”
Feb 29, 2024 positive
Feb 29, 2024 negative
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…”
Feb 29, 2024 positive
The primary customer a pivoting founder must convince is themselves
“The metaphor I sometimes like to tell people when they're pivoting is the most important customer is yourself. And the founder psychology thing you want to do is build conviction in your own mind that this thing is worth working on. And so it's not to make inv…”
Feb 29, 2024 negative
Feb 29, 2024
Mar 21, 2024 neutral
Mar 21, 2024
Caldwell: Founders avoid launching because they fear capping out at $50M ARR
“We see this a lot where there's companies that find real problems and something they're experts in, but they are facing crippling anxiety that it's not venture scale. Again, they might be right, but they're so obsessed with this way of thinking that, oh, what …”
Mar 21, 2024 negative
Caldwell: YC Applicants Often Pitch Big-Company Decks With Zero Traction
“An example that I notice a lot in a YC interview is They want to present a PowerPoint deck or a slide deck. And the way they describe the company is the way you would describe a very large company. But then when you're like, well, do you have any customers? No…”
Mar 21, 2024 neutral
Mar 21, 2024
Caldwell: Early-stage founders must unlearn corporate skills and spreadsheet modeling
“All, you know, all the Excel spreadsheet modeling you learn as an investment banker. That's great. Just turn that off though. Like unlearn that doesn't serve you now. And embrace the beginner's mind. To get your startup off the ground.”
Mar 21, 2024 neutral
Mar 21, 2024 positive
Caldwell: Founders reaching $20M–$40M ARR rarely run out of growth ideas
“It's so rare in this job where we see a company that gets to 20,000,030 1,000,040 million in annual revenue, and the founder has no idea on how to grow it. They're out of ideas. I'm not going to say that never happens, but it's extremely rare.”
Mar 21, 2024 negative
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.”