Sam Lessin
29 statements across 4 episodes · 11 bullish · 15 bearish · 1 people on the record · first statement May 25, 2016 by Sam Lessin · said 48 times in 18 episodes since 2016 · across every show →
On the record as a speaker too: Sam Lessin's record, appearances and statements → this page counts the times other people say the name.
Mentions by year
brought up most by Harry Stebbings (27), Dave Morin (7), Matt Mazzeo (6), Jason Lemkin (3), Mike Maples (2), Will Quist (1), Gary Liu (1), Alexa von Tobel (1)
tap a year for its mentions
2026 1 mention in 1 episode
2025 3 mentions in 2 episodes 2 per episode
2023 13 mentions in 6 episodes 2 per episode
- Phin Barnes: The Services Model of Venture Capital is Broken, The Best Founders Do Need Help | E1067 · 20VC with Harry Stebbings
- Beezer Clarkson: Are LPs Open for Business & Why Do LP Incentive Mechanisms Need to Change? | E1073 · 20VC with Harry Stebbings
- Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
- Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
- Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
- Adam Mosseri: Why Video Is Bad For Business; Does Feed Matter Anymore? | E1039 · 20VC with Harry Stebbings
- every mention in 2023, scene by scene →
2022 2 mentions in 1 episode
2020 5 mentions in 1 episode
2019 2 mentions in 2 episodes 1 per episode
- 20VC: Why Startup Founders Have One Core Job, How To Reduce Risk & Increase Probability In Your Startup & Why You Should Not Send A Pitch Deck Pre-Investor Meeting with David Rogier, Founder & CEO @ Masterclass
- 20VC: How To Build Meaningful Relationships With Your Investors, 4 Key Elements CEOs Must Focus On In Scale Mode & How Top Optimise Leadership Team Dynamics with Joel Flory, Founder & CEO @ VSCO
- every mention in 2019, scene by scene →
2017 1 mention in 1 episode
2016 21 mentions in 4 episodes 5 per episode
- 20VC: Dave Morin on Why Building A Fund Is Like A Company, Why Venture Is A Craft & The Journey To Establish Slow Ventures
- 20VC: Lowercase's Matt Mazzeo on Being Chris Sacca's Partner and The 3 KPIs to Successful Investing
- 20VC: The Information's Jessica Lessin on The Future For Online Journalism & The Benefits Of A Subscription Based Business Model
- 20VC: Digg CEO, Gary Liu on The Rebirth Of Digg & The Evolution Of Content
- every mention in 2016, scene by scene →
Everything said about Sam Lessin, oldest first
May 25, 2016 negative
May 25, 2016 positive
May 25, 2016 negative
May 25, 2016 bullish
Lessin: Augmenting memory is the most compelling bot use case
“I'll tell you the thing that I love the most is augmenting my memory. I don't have the world's greatest memory. I like to take lists. I try to keep lists together and things like that, but I find it really, really hard to keep track of all The ideas and people…”
Feb 4, 2019 positive
Operating and investing simultaneously makes you better at both
“I'm a huge believer in investing and operating at the same time. I think being an investor who makes you a much Better operator and being an operator makes you a better investor. You know, investors can't go deep on anything, and they really don't understand w…”
Feb 4, 2019 neutral
Feb 4, 2019 negative
Feb 4, 2019 positive
Knowledge work will shift to on-demand cloud infrastructure
“And I think, you know, the future of work probably looks a lot more like this kind of cloud metaphor where, you have kind of the ability as a firm or as someone who needs to get a task on a turn on or turn off capacity. Utilization can go up. You know, you hav…”
Aug 11, 2023 negative
Aug 11, 2023 bullish
Aug 11, 2023 bullish
Lessin: Founders will prefer 80% of a $50M business over VC scale
“I actually am very optimistic that there's gonna be a whole generation of people like, oh shit, I would, you know, I, it is a much better life to own 80% of a business that has fifty million top line than on 10% of a business that does 500, right? With a bunch…”
Aug 11, 2023
Lessin: I personally invest in deals Slow Ventures deems too expensive
“There are places like, you know, in history, there have been a few instances, my partners are like, we like the deal, it's too expensive. I'm like, ah, fuck it. I'll put in a few personal dollars because like, who cares? It's so little money, right?”
Aug 11, 2023 bearish
Aug 11, 2023 bullish
Lessin: Slow Ventures will target sub-$5M valuation, self-sustaining seed deals
“I am very excited to fund a bunch of companies at five and under in weird things that are coming to you because no one else will give them money that are going to be highly profitable on the way up and create option value down the line. Right. So it's kind of …”
Aug 11, 2023 negative
Lessin: VC's worst outcome is picking a winner without equity upside
“You know, I think the most depressing thing in the world is not being wrong. It's being right and not making money. You know, being right to the tune of, like, having these epic outcomes and being like, ah, fuck, that was a one-ex returner of the fund, right? …”
Aug 11, 2023 negative
Lessin: I will not fund Stanford graduates trying to be Elon Musk
“So yeah, of course, like the kids coming out of Stanford who like have this, like, I want to be Elon Musk thing. Like, I'm not gonna fund those people, right? Like, you know, every once in a while, I'll miss one because like, I love the founders fund guys. The…”
Aug 11, 2023 bearish
Aug 11, 2023 bearish
Lessin: The factory model of seed investing is dead and won't return
“My view when I say Seed is dead is that I think the factory model of Seed, which supported massive scaling of it, is dead. And we're kind of back to where we have been historically, which is Seed is a bespoke It's a bespoke thing. Some people can do it well. I…”
Aug 11, 2023 bullish
Aug 11, 2023 negative
Aug 11, 2023 bearish
Aug 11, 2023 negative
Aug 11, 2023 bullish
Lessin: Future of VC is $3M capital-efficient, profitable startups
“I think the future is in these companies. There are a lot of companies you can put three million dollars into and get to a place where like, you're pretty sure it's profitable. It's going to be worth, it's worth a 102 hundred, and you have an option on somethi…”
Aug 11, 2023 negative
Jun 5, 2025 bearish
Jun 5, 2025 bullish
Lessin: Seed investors can exit via secondaries unlike Series A leads
“I really strongly believe private to private is an important future, and I love being early and small and first because I actually can sell into the private markets in a way that you can't if you've written a 30, forty million dollar check into the Series A.”
Jun 5, 2025
Lessin: VCs take longer to master selling than buying
“As an early stage investor, you get hundreds of shots to buy. You get really good at buying. You have so fewer shots at learning to sell that it actually takes much longer to learn to sell well. Right. But it's still as important as learning to buy well.”
Jun 5, 2025 bearish
Lessin: $1 billion venture capital funds operate in a death zone
“I don't know how you make multiples on a billion dollars consistently, right? In VC. I think once you're doing 10, you're playing a completely different game of asset gathering and asset deployment where you no longer have the same Goals. So I personally think…”