Caldwell: Brex and Retool appeared to be their YC batch's worst startups
Dalton Caldwell · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (YC) · Apr 18, 2024 · at 13:39
Dalton Caldwell, Managing Director at Y Combinator, recounts the Winter 2017 batch to illustrate why early batch struggles do not predict long-term startup outcomes.
0:00 / 0:27exact quote · 27.3s
▶ Watch the full episode on YouTube → 720p mp4 · rendered on demand · StarZero watermark
“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 worst in terms of like, it's, everything is going bad were by far in retrospect, the most successful companies in that group.”
quote is from the automated transcript, cleaned for reading: filler sounds and stutters are removed, nothing is rephrased. names can be misheard (the analysis reads context, assessments check outside sources). how →
More from Dalton Caldwell
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: 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…”