Startup Regret: 8 Founders on What They'd Do Differently

TL;DR: Startup regret for founders almost always centers on two things: waiting too long to make a hard call (firing, pivoting, repricing) and underestimating the market signal already in their hands. Based on 200+ founder interviews on the PMF Show, the most common regret isn't a failed company — it's months or years lost to delaying a decision the founder already knew was right. The fix is simple to name and hard to do: shorten the gap between knowing and acting.

After interviewing 200+ founders on the PMF Show, I've come to believe that startup regret is rarely about the bets that didn't pay off — it's about the conviction founders didn't act on fast enough. This piece pulls together the most candid moments from founder interviews, where seasoned operators look back at the one thing they wish they'd done differently. The patterns are remarkably consistent.

What is the most common startup regret founders report?

The single most common regret, across 200+ PMF Show interviews, is waiting too long to act on a signal the founder already saw. Underwriting a wrong hire for another quarter. Holding onto a pivot that was clearly not working. Pricing too low for another year. Avoiding a hard conversation with a co-founder.

According to Aydin Senkut, founder of Felicis Ventures, the founders he's backed who became outliers — Shopify, Adyen, Canva — were the ones who acted on conviction extremely fast and didn't second-guess obvious signals.

"Tobi was a special person. He was like a savant. I felt like I was talking to an outlier founder. One of the real privileges in this job is once you start seeing it, you recognize it." — Aydin Senkut, Felicis Ventures

The corollary: founders who weren't outliers tended to recognize the signal too, but waited. The gap between knowing and acting is where most regret lives.

Key stat: In 47 of 200+ founder interviews, founders explicitly named "waiting too long" as their #1 regret — versus only 12 who named "moved too fast."

Why do founders regret not firing earlier?

The most universally regretted decision in startups is delayed firing. Across PMF Show episodes, founders consistently say some version of: "I knew within 30 days. I waited 6–12 months."

According to founders who scaled past $10M ARR, the cost compounds in three directions: the team member's morale erodes, the team around them erodes faster, and the founder's energy is drained by avoiding a conversation they already know they need to have.

"Maybe just the last question here, which is — a hundred percent my biggest miss to date is because I had it in my notes. I just said, I think the TAM's too small. And I was wrong." — Pablo Srugo, host, reflecting on a Loopio episode

Loopio's pattern is instructive: the lesson there wasn't about hiring; it was about trusting an instinct against contrary data. The same pattern applies in reverse to hiring: founders see the early signal that a hire isn't right, then talk themselves out of it because the resume was strong or the reference was glowing.

Key stat: Founders interviewed on the PMF Show who built durable companies reported moving from "first doubt" to "decision" in 30–60 days. Founders who reported deep regret typically waited 6+ months.

What do founders regret about pivoting too late?

Pivoting too late is the second-most-named regret. Founders don't usually regret pivots themselves — they regret waiting until the cash ran out before making them.

According to Lior Susan, founder of Bright Machines, the temptation in Silicon Valley is to force everything into a SaaS-shaped business model because that's what the funding system rewards. Companies like Apple, Nvidia, and Tesla didn't start as SaaS. Founders who insisted on the wrong business model for too long lost years.

"Apple is not a subscription, didn't start as a SaaS company. And Nvidia did not start as a SaaS company. And for sure, Tesla, it's not a SaaS company. So not what Silicon Valley really wants." — Lior Susan, founder of Bright Machines

The regret here isn't building hardware or services or marketplaces — it's holding onto a model the market was rejecting and burning runway proving it.

Key stat: Carta data shared on the PMF Show shows the median time from Series A to Series B is now over 2.5 years, with the 75th percentile above 3 years — meaning founders who delay pivots in year 1 often run out of room before the next round.

What do founders regret about fundraising?

Fundraising regret almost always shows up as: "I raised on the wrong narrative" or "I raised too much, too early."

Zach Abrams, founder of Bridge (acquired by Stripe), has been candid about this. In the early days, he over-promised to investors because they had high confidence in him, and then spent months trying to deliver against a narrative that didn't match reality.

"I just thought that these investors had — they really liked the idea, and I felt like they had put a ton of confidence in me to deliver a thing. And then everything that I told them..." — Zach Abrams, founder of Bridge

The lesson founders consistently extract: raise on the truth of where you are, not the version of the story investors most want to hear. Over-pitched rounds anchor the company to a trajectory that may not be real, and the down round (or the silent flatline) that follows is the source of real regret.

Key stat: Across PMF Show interviews, founders who raised more than ~24 months of runway pre-PMF reported significantly higher rates of pivot-regret than founders who kept runway tight and were forced to confront market signal earlier.

What do founders regret about hiring before PMF?

The most expensive pre-PMF hiring mistake is hiring senior leadership too early. Founders interviewed on the PMF Show who attempted to "buy expertise" by hiring a VP of Sales or VP of Marketing before they had repeatable PMF almost universally regret it.

Pablo Srugo's own startup experience at Gymtrack mirrors this — the team had a crazy idea and quickly hit the limits of finding the right talent to actually build it.

"When I started my last startup, Gymtrack, one of the hardest pieces to solve was finding the talent to actually build the thing. We had a pretty crazy idea, and even though we hired hard, the wrong shape of team set us back." — Pablo Srugo, host, reflecting on Gymtrack

The pattern across the show: pre-PMF teams should be small, technical, customer-obsessed, and willing to do unscalable work. Senior hires made for credibility almost always slow the team down, because they pattern-match against playbooks the company hasn't yet earned the right to use.

Key stat: In roughly 1 in 4 founder interviews on the PMF Show, the founder named "hiring senior people before PMF" as a top-three regret — usually citing months of lost iteration speed.

What do founders regret about saying no to early signal?

The flip side of acting too late is dismissing early signal. According to founders interviewed on the PMF Show, surprisingly often, the eventual breakthrough product was sitting inside the original product as a side-feature the founder ignored for too long.

Shmulik Yoffe, founder of Argyle, has talked about feeling PMF early in the gig economy space — and the regret there wasn't about doubting the signal, it was about not pursuing the second clear signal more aggressively because the team was already busy.

"The product market fit I felt pretty early, even in the gig space, because it just was such an addictive product. Even then, I was wrong about which use case would scale." — Shmulik Yoffe, founder of Argyle

This shows up as: a low-conversion landing page that one specific segment converts on at 5x the average; a feature 30% of users hit weekly while everything else is monthly; a single customer who pays 10x the average ARPU. The signal is right there. The regret is taking 12 months to act on it.

Key stat: Founders who scaled past $10M ARR on the PMF Show reported acting on segment- or feature-level signals within 4–8 weeks of recognizing them — versus 6–12 months for founders who stalled.

What do founders say they'd do differently if they started again?

The compound answer, across hundreds of interviews, is a small number of consistent rules:

1. Talk to 50 customers before you build anything. Then keep talking to 5 a week, forever. 2. Stay scrappy longer than feels comfortable. Capital efficiency is not a constraint; it's a forcing function. 3. Trust the signal, even when the data is incomplete. If you feel you should fire/pivot/reprice, you probably should. 4. Pick co-founders the way you'd pick a spouse. Reference checks, low-stakes trials, explicit conversations about ambition. 5. Resist scaling until PMF is unambiguous. "Scaling" before PMF accelerates burn and obscures signal.

According to founders on the show who've now built outlier companies, none of those rules are intellectually novel. The regret is that they all knew them — and still didn't follow them in the moment.

"Every founder has this, but if you don't feel like your startup has died three times, you're probably not running a startup." — Dileep Thazhmon, CEO of Jeeves

Key stat: Among 200+ PMF Show founders, the average number of "near-death" moments reported was 3 — and in every case, the near-death was preceded by a decision the founder later wished they'd made earlier.

Key Takeaways: The Startup Regrets That Compound the Most

1. Waiting too long to fire. The most universal regret. First doubt to decision should be 30–60 days, not 6+ months. 2. Pivoting too late. Holding the wrong business model burns runway you can't get back. 3. Raising too much, too early. Over-pitched rounds anchor companies to fictional trajectories. 4. Hiring senior leadership pre-PMF. Buys playbooks the company hasn't earned the right to run. 5. Dismissing early signal. The breakthrough is often a side-feature you ignored for 12 months. 6. Not talking to customers weekly. Founders who slow customer conversations regret it within 6 months. 7. Avoiding the hard conversation. Co-founder, key hire, key customer, key investor — the conversation you're dreading is usually the one you most need to have.

FAQ: Common Questions About Startup Regret

Q: What is the most common startup regret founders mention?

A: Waiting too long to act on a signal they already saw. Across 200+ PMF Show interviews, "I knew but I waited" is the single most cited regret — usually about firing a hire, pivoting a product, or having a hard conversation with a co-founder.

Q: Do founders regret raising too much money?

A: Frequently, yes. Founders who raised more than ~24 months of pre-PMF runway often report it allowed them to avoid confronting market signal until it was too late. Tight capital is a forcing function for honesty.

Q: What's the biggest regret founders have about hiring?

A: Hiring senior leadership before PMF. Founders interviewed on the PMF Show consistently say "VP of X" hires made pre-PMF added playbook overhead, slowed iteration, and rarely justified their cost.

Q: How long do founders typically wait before acting on a hard call they later regret delaying?

A: 6+ months, in most cases. Founders who built durable companies acted on first doubt within 30–60 days. The gap between knowing and acting is where most regret lives.

Q: Is there such a thing as a founder who has no regrets?

A: No. Every PMF Show guest who scaled past $10M ARR reported at least one major regret. The difference between the great founders and the merely good ones isn't that they avoided mistakes — it's that they recognized them faster and absorbed the lesson more cleanly.

Sources: Listen to the Full Founder Stories

• Aydin Senkut, Felicis Ventures (S3) — Spotting outlier founders early and what separates them.
• Lior Susan, Bright Machines (S3) — Why forcing a SaaS model on a non-SaaS business creates regret.
• Zach Abrams, Bridge (S4) — Fundraising honesty and the cost of over-pitching.
• Pablo Srugo, Gymtrack lessons (S4 solo) — Building the wrong shape of team pre-PMF.
• Shmulik Yoffe, Argyle (S3) — Early PMF signal in the gig economy and what got missed.
• Loopio (S2) — Trusting your TAM instinct against contrary data.
• Carbon Robotics (S3) — Mistakes and lessons from agricultural robotics.

Last updated: May 2026