Feb 4, 2019 · 36m · 20vc
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
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In this episode of 20VC, host Harry Stebbings interviews Sam Lessin, Founding Partner at Slow Ventures, about venture capital fund mechanics, human-AI symbiosis in knowledge work, cryptocurrency protocol scaling, and the societal challenges of deepfakes.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 31.9% of the talking time here. How this is scored →
Harry as informed peer 4.7 Guest teaching 4.3 Guest disagreement 2.2 Harry pushing back 2.4
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 30:15 Calling platform surprise excuses 'a load of bollocks'
Sam forcefully rejects the host's leading premise that platform problems were unforecastable, calling tech industry surprise narratives a load of bollocks.
Hardest push from Harry ▶ 18:17 Challenging crypto decentralization with centralized realitiesHarry directly challenges Sam's crypto decentralization thesis by arguing that centralized entry points like Coinbase and app layers re-centralize user power.
Biggest teaching moment ▶ 24:05 Explaining municipal game theory and scooter profit limitsSam educates Harry on micro-mobility economics, explaining how cities learned from Uber and will restrict scooter margins to protect municipal infrastructure.
Harry holds his own ▶ 22:40 Citing Avichal Garg to challenge global decentralizationHarry demonstrates deep sector awareness by citing Avichal Garg's thesis on Silicon Valley re-centralization to press Sam on regional tech power.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Sam Lessin on Transitioning from Angel Investing to Institutional Venture Capital | 4 | 4 | 1 | 1 | Harry asks an off-schedule question about how Sam's mindset shifted when moving from angel investing to institutional VC. Sam explains that small check wins mean a lot to personal finances but are statistically irrelevant to a $200M fund, reframing how fund economics force specific business types to exist. | |
| Evaluating Market Sizing and the Scale of Global Niche Markets | 4 | 3 | 1 | 1 | Harry quotes Danny Rimer from Index Ventures regarding VCs underestimating niche market sizes. Sam agrees in part, detailing his 10x and 100x mental framework, while noting that globalized markets scale small niches far bigger than expected despite hard market size boundaries. | |
| The Knowledge Work Cloud and Precision Operational Measurement | 3 | 4 | 0 | 0 | Harry asks about the 'human knowledge work cloud' concept, prompting Sam to elaborate on the analogy between AWS compute infrastructure and operational workforce management. Sam explains that precision operational measurement acts like New Relic for human workflows. | |
| Workplace Productivity, Human Engagement, and the Future of Work | 5 | 4 | 2 | 2 | Harry cites an article by Sam's partner Andrew Cortina regarding male productivity decline to probe whether human apathy is to blame. Sam reframes the issue around global competitive leverage and micro-breaks during work hours rather than inherent laziness. | |
| Crypto Infrastructure, Decentralized Databases, and Protocol Priorities | 6 | 5 | 2 | 5 | Harry challenges Sam's decentralized crypto narrative by pointing out that centralized apps like Coinbase capture most user value and quoting Adam Goldberg on dApp infrastructure limits. Sam responds by emphasizing that securing the base database layer must come before scaling user applications. | |
| Valuation Dynamics in Crypto and the Global Decentralization of Tech Hubs | 6 | 5 | 4 | 4 | Harry cites Avichal Garg from Electric Capital on crypto pricing difficulty and his claim that tech hubs will re-centralize in Silicon Valley. Sam disagrees with the Valley re-centralization thesis, highlighting active global crypto hubs across Israel, Asia, and New York. | |
| Why Scooter and Micro-Mobility Companies Struggle as Venture Investments | 5 | 6 | 3 | 3 | Harry notes European VCs rushing into micro-mobility and asks why Sam considers scooters a poor venture business. Sam delivers a lesson on municipal game theory, explaining that cities burned by Uber will not allow scooter companies to extract high profit margins off city infrastructure. | |
| Deepfakes, Information Architecture, and the Trade-Off Between Freedom and Security | 6 | 6 | 6 | 5 | Harry brings up Sam's tweets on synthetic video and asks a leading question assigning blame to distribution platforms like Facebook. Sam rejects the premise that platform dynamics were unexpected, calling claims of surprise 'a load of bollocks' and pointing out that social trust systems are simply unwinding online. | |
| Quickfire Round: Book Recommendations, Attention, Operating, and Fetcher.ai | 3 | 2 | 1 | 1 | In a rapid-fire sequence, Harry asks about book recommendations, attention management, operating while investing, and recent deals. Sam explains why active operating at Finn makes him a sharper investor at Slow Ventures. |
Statements from this episode (20)
A $5M exit is a failure for a $200M VC fund
“A five million dollar exit to a two hundred million dollar fund is basically irrelevant, right? That's actually a failure in a lot of cases.”
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.”
Investors systematically underestimate the scale of global niche markets
“I think people systematically under appreciate how large the world is, and therefore, especially in a globalized environment, how big niche markets actually can be when you blow them up and scale them up.”
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 …”
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.”
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…”
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.”
Workers in Western countries engage in very little actual work
“And the answer is in the West, we work very little.”
AI will make steady, repeatable, predictable jobs much harder to find
“I think the real thing that's going to be challenging is that I think it'll be harder to find steady, repeatable, trusted work.”
Crypto fundamentally provides decentralized memory and identity
“What crypto really fundamentally is that when you really strip it all away, it is that secure ability to have secure, decentralized, private memory and secure decentralized private identity.”
Ethereum cannot support decentralized applications operating at scale
“Ethereum cannot support anything of scale.”
Slow Ventures avoids dApp investments to focus on crypto protocols
“First, we, I generally don't invest in dApps. Again, like we're much more focused on protocols. There are very few exceptions we would make to that.”
Crypto is the most globalized tech boom to date
“So crypto is by far the most globalized The tech revolution or boom we've seen in my mind to date”
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.”
The electric scooter market is not winner-take-all
“No, I don't think it's a winner-take-all market.”
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?”
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.”
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.”
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…”
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…”