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Opinion
Lessin: Founders who ask VCs for help are weak
“Because I, if you're coming to me for help, my view is you're almost by definition, or you're saying, I need help or whatever I want help. I think you're a weak founder.”
Sam Lessin Aug 11, 2023 ▶ 44:28 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Opinion
Lessin: Venture fund paper markups are irrelevant and often negative signals
“I know full well, I know this is an investor. That the marks that you made up or the marks of SoftBank listed something somewhere are completely irrelevant. In fact, the negative signal in a lot of cases. So like the marks are irrelevant and stupid.”
Sam Lessin Jun 5, 2025 ▶ 4:41 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Opinion
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…”
Sam Lessin Jun 5, 2025 ▶ 8:54 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Opinion
Lessin: Most capital deployed into Series A rounds is completely wasted
“Most of the money at Series A is completely wasted, right?”
Sam Lessin Jun 5, 2025 ▶ 14:45 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Opinion
Lessin: Chime is not an important or paradigm-shifting company
“Is Chime an important company? I just don't see it, right? Like, is it, you know, it's good company? Like, they provided some banking products to unbanked people or underbanked people. I get it. It's not bad. They did a good job. They built a good app. But lik…”
Sam Lessin Jun 5, 2025 ▶ 31:10 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Prediction Not checkable as stated
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…”
Sam Lessin Aug 11, 2023 ▶ 2:45 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Prediction Not checkable as stated
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…”
Sam Lessin Aug 11, 2023 ▶ 31:06 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Disclosure
Lessin: Slow Ventures avoids Y Combinator deals because they lack signal
“As an investor, you know, we've stayed away from it for a long time, partially because there's no signal in it because everything comes off the factory line looking exactly the same, packaged properly.”
Sam Lessin Aug 11, 2023 ▶ 37:42 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Ethereum cannot support decentralized applications operating at scale
“Ethereum cannot support anything of scale.”
Sam Lessin Feb 4, 2019 ▶ 20:18 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Prediction Not checkable as stated
Western democracies lack structures to re-examine constitutional governance for tech
“For instance, I think that things as basic as, you know, the Constitution, et cetera, really are going to have to be reexamined in a lot of ways, and I don't think that we have the social structures to do that very well in the West.”
Sam Lessin Feb 4, 2019 ▶ 28:50 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Opinion
Lessin: AI is extremely overhyped and largely fictitious
“We think AI is extremely overhyped. And also kind of fictitious.”
Sam Lessin May 25, 2016 ▶ 7:35 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Opinion
Lessin: The internet has failed as an information platform
“I personally believe the internet has mostly failed in its mission to become an information platform. It's a great content platform. It's super engaging, but it doesn't inform the way I expect it to. I'm super disappointed in Wikipedia.”
Sam Lessin May 25, 2016 ▶ 15:18 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Prediction Not checkable as stated
Lessin: Society will rent everything; only poor people will own items
“I think we're going to live in a world where the only people who don't rent everything are the people who can't afford to. So ironically, it will be only poor people, right? Who won't be completely rental based.”
Sam Lessin May 25, 2016 ▶ 19:59 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Prediction Not checkable as stated
Lessin: Capitalism cannot survive an ultra-efficient, deflationary world
“So if we get much more efficient and you live in a fundamentally deflationary world, like I don't know how capitalism survives that, you know, which is going to be, I think, really exciting.”
Sam Lessin May 25, 2016 ▶ 20:11 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Insight
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.”
Sam Lessin Jun 5, 2025 ▶ 15:27 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Insight
Lessin: Customer acquisition cost only goes up as companies scale
“CAC only goes up, right? Like people just consistently get this wrong, right? And so I think that. Almost always up at scale, right? It's like, this is how the world works. And like, you know, the kind of argument that you're going to get good at something and…”
Sam Lessin Jun 5, 2025 ▶ 30:18 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Opinion
Lessin: The most obvious AI bets are Facebook, Amazon, and Microsoft
“It's like, you want to bet on AI? Bet on Facebook. Bet on Amazon. Bet on Microsoft. It's so obvious.”
Sam Lessin Aug 11, 2023 ▶ 0:05 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Disclosure
Lessin: Slow Ventures' top seed returns came from non-consensus, cheap deals
“When I look at our seed portfolio over a long period of time now, my own personal investing longer, you know, the seed deals that have mattered have always been the ones that were hardest to package. They were not on the factory line. The places we've made ser…”
Sam Lessin Aug 11, 2023 ▶ 7:17 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Disclosure
Lessin: Slow Ventures made a 1,000x return on its Solana seed
“Like, I made a thousand X on our Solana seed, right?”
Sam Lessin Aug 11, 2023 ▶ 21:19 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Insight
Lessin: Seed fund math breaks down for mega seed funds
“If you have a 50, even a hundred million dollar fund, you can make seed math work. But these mega seed funds, like, and all of a sudden, oh my god, your two billion dollar return is only a three x. Like, the math won't work, right?”
Sam Lessin Aug 11, 2023 ▶ 22:12 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Prediction Not checkable as stated
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…”
Sam Lessin Aug 11, 2023 ▶ 30:40 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Assertion Supported
Lessin: VC funds are cutting target sizes amid LP pullback
“They're funds, they're cutting fund sizes left and right, and they're combining funds to bulk them up.”
Sam Lessin Aug 11, 2023 ▶ 57:36 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Prediction Not checkable as stated
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 …”
Sam Lessin Aug 11, 2023 ▶ 1:01:50 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Insight
Institutional VC forces specific business models, leaving good companies unfinanced
“From an institutional capital model perspective, it ends up forcing certain types of companies to exist, and making it very hard to finance other types of companies that might be very good companies, but can't provide that type of venture economics.”
Sam Lessin Feb 4, 2019 ▶ 5:46 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Prediction Held up
Cities will not allow scooter companies to be meaningfully profitable
“I don't think the cities are going to let the scooter companies be profitable or be meaningfully profitable.”
Sam Lessin Feb 4, 2019 ▶ 24:22 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Prediction Not checkable as stated
Media trust will collapse when AI deepfakes reach human-level realism
“But that trust is going to go away as soon as we have algorithms that can fake video and photos as well as, you know, we can tell with our eyes, right?”
Sam Lessin Feb 4, 2019 ▶ 28:18 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Prediction Not checkable as stated
Lessin: Display advertising will become irrelevant in a bot world
“You know, I think obviously in a bot world, a lot of the display driven, engagement driven advertising that, you know, we're all used to seeing as the way services monetize and exist becomes a heck of a lot less relevant.”
Sam Lessin May 25, 2016 ▶ 11:29 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Prediction Not checkable as stated
Lessin: Auto industry won't survive as required car volume collapses
“I think it's going to be pretty hard for the auto industry to survive at all. Right. Because just the number of cars we're going to need is going to go dramatically down.”
Sam Lessin May 25, 2016 ▶ 18:43 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Prediction Not checkable as stated
Lessin: Private car ownership will end in favor of shared vehicles
“I cannot come up with a possible world where we don't end up sharing cars. It just, I literally, it does not, maybe in a world of infinite free energy and, you know, zero pollution and no resource constraints, everyone owns cars, but x that, there's no possibl…”
Sam Lessin May 25, 2016 ▶ 18:59 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Insight
Lessin: Venture allocators must never sell their top-performing assets
“The number one rule as a fund out an allocator is you cannot sell the things that matter.”
Sam Lessin Jun 5, 2025 ▶ 16:25 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Opinion
Lessin: Public markets ignore $200M revenue companies with 30% margins
“No one gives a shit about a company that does two hundred million in top line and grows with 30% margins, right? No one cares.”
Sam Lessin Aug 11, 2023 ▶ 51:25 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Insight
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? …”
Sam Lessin Aug 11, 2023 ▶ 23:22 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Prediction Not checkable as stated
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…”
Sam Lessin Aug 11, 2023 ▶ 25:22 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Disclosure
Lessin: Slow Ventures is stepping back from SaaS investments
“I'm not spending a lot of time on SaaS these days, I think partially for the dynamics you're talking about, right?”
Sam Lessin Aug 11, 2023 ▶ 33:50 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Insight
Lessin: Willingness to join early startups anti-correlates with sales talent quality
“I think sales is incredibly hard to hire at startups, specifically because the whole nature of sales is like the people who want to go early are like anti correlated with the good people, right?”
Sam Lessin Aug 11, 2023 ▶ 48:24 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Insight
Lessin: Good tech businesses are worth less today, but great ones command higher premiums
“The good businesses aren't worth as much as people thought they were. The great businesses are worth more.”
Sam Lessin Aug 11, 2023 ▶ 52:01 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Insight
AI productivity gains require reorganizing work around human leverage
“To my own horn, as I was trying to push years ago, and we still push you know, the real model, I think, is you have to think about AI and people as symbiotic, and you have to think about the real transition in the industrial revolution of knowledge work we're …”
Sam Lessin Feb 4, 2019 ▶ 8:19 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Prediction Not checkable as stated
Full AI adoption in knowledge work will take 15 to 20 years
“It's going to be faster. Maybe it's 20 years, right, for AI, or 15 years for AI to be adopted, but it's also not tomorrow.”
Sam Lessin Feb 4, 2019 ▶ 9:55 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Prediction Not checkable as stated
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…”
Sam Lessin Feb 4, 2019 ▶ 11:13 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Insight
Technology and productivity are the only way Western economies retain jobs
“I mean, I would argue that technology and productivity is the only path to having jobs.”
Sam Lessin Feb 4, 2019 ▶ 14:11 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Assertion Not checkable as stated
Workers in Western countries engage in very little actual work
“And the answer is in the West, we work very little.”
Sam Lessin Feb 4, 2019 ▶ 14:50 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Opinion
The electric scooter market is not winner-take-all
“No, I don't think it's a winner-take-all market.”
Sam Lessin Feb 4, 2019 ▶ 25:19 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Insight
Social platforms face an impossible trade-off between privacy and security
“I think that they're in an unwinnable position in a lot of ways because society is simultaneously telling them we want privacy and we want security. And as I said, you can't have both. You have to make some choices.”
Sam Lessin Feb 4, 2019 ▶ 30:48 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Insight
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…”
Sam Lessin Feb 4, 2019 ▶ 32:36 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Prediction Not checkable as stated
Another wave of consumer apps is not coming anytime soon
“I would love to see some form of consumer apps come back. I think we're at like a pretty boring place for consumer apps for the last bunch of years, and I don't think we're done building them. That's kind of, I don't know how that would happen. I think you'd n…”
Sam Lessin Feb 4, 2019 ▶ 33:16 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Disclosure
Lessin: Fin charges users directly because human-augmented AI is costly
“Our business model for Fin is extremely simple, which is we charge people for it. And, you know, we charge people for it both because of the service we offer is expensive to run. It's, I mean, AAI is not an inexpensive thing to do well because it's not just bi…”
Sam Lessin May 25, 2016 ▶ 12:03 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Insight
Lessin: Very few companies build sustainable businesses on affiliate fees
“Affiliate models, just, I don't know, like there are very few companies that have made them sustainably good businesses, right? You know, I would challenge you to come up with a company that's deeply driven by affiliate fees that works in the longterm.”
Sam Lessin May 25, 2016 ▶ 13:13 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Assertion Supported
Lessin: The long tail of mobile apps has failed
“The long tail of apps has mostly failed, right? The real estate and time and attention has been taken up by a few head application publishers.”
Sam Lessin May 25, 2016 ▶ 14:26 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
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