Sam Lessin, a General Partner at Slow Ventures, former VP of Product at Facebook, and founder of Drop.io and Fin, is a prominent voice in the tech and venture capital landscape. Known for his candid and often contrarian perspectives, Lessin shares his insights through his writing at The Information, various interviews, and podcasts.
On Venture Capital and Investing
- The End of an Era: "The 'factory system' era of venture is dead."[1] Lessin argues that the model of predictably manufacturing billion-dollar companies is no longer viable.
- The Middle Market Squeeze: "I think the really big guys are fine, I think the really small guys are fine, but it'll be competitive and the middle drops out because the middle always drops out."[2]
- The Inefficiency of Seed Investing: Lessin views seed investing as "the least efficient market in the world," which is what makes it an attractive space for finding unique opportunities.[3]
- The Real Job of a VC: "What I'm best at is finding people and finding ideas that other people have written off and saying 'But what if they're right?'"[3]
- The Nature of Early-Stage Investing: "You're mostly wrong, you mostly lose money… Success comes from being very right occasionally, not being right consistently."[4]
- On Conviction: "I love when everyone thinks I'm wrong and I'm right, it's like emotionally very valuable to me and so it's a good match with seed investing."[5]
- Investing in People: "Investing directly in people is the future of VC."[6][7] Lessin is a proponent of investing in creators and entrepreneurs as individuals, not just in their companies.
- The Value of Weird Ideas: Slow Ventures actively seeks out "weird" investment ideas, such as income share agreements and backing creators.[8]
- Venture Capital is Just Money: "Everyone says you think of a VC as something special, it's not, it's just money, and more and more people are willing to play in the money game."[2]
- Capital as a Tool: "You want to be the person who said capital is my tool. I'm looking for places to deploy that's the highest leverage where no one else is and it's good for me and it's good for capitalism."[3]
On Startups and Founders
- The Missionary Mindset: "The only way to get through that and be successful is to truly be missionary about what you're working on."[9]
- Emotional Resilience is Key: Lessin looks for founders who are in a place "where they're going to be able to weather the downs and also not get too manic at the ups."[9]
- The 'Wizard of Oz' Method: For complex ventures, Lessin advises starting with a manual process to deeply understand the problem before building technology.[10]
- The Importance of Patience: "Most success isn't quick wins. Venmo took 'so many turns of the crank.' Be patient finding the right wind, then sail fast when you catch it."[4]
- Founder-Market Fit: "Don't ask 'is this a great person?' Ask, 'Is it the right person at the right moment?' Success requires all three elements to align, not just talent."[4]
- Forgoing the "Gold Star": Lessin encourages aspiring entrepreneurs to move beyond seeking external validation and realize that "you could just do stuff."[5]
- The Value of Focus: He advises founders to avoid the temptation of starting multiple businesses that aren't authentic to their core brand and mission.[11]
- The Challenge of Hard Tech: Lessin cautions against starting highly complex ventures without significant experience and financial security.[10]
On Technology and the Future
- AI is Not a Disruptor (for startups): "AI is a big deal, but not for startups...it's just more internet."[1] He believes the major benefits of AI will accrue to the incumbent tech giants.
- Crypto is Fundamentally Disruptive: "AI is kind of like mobile. It's not disruptive. It's great tech. Crypto is fundamentally disruptive."[5]
- The Future of Brands is People: "The most valuable brands of the future are going to be people rather than companies."[6]
- The Metaverse is Coming: Lessin has written about the impending arrival of the metaverse and its potential implications.[7]
- Bots and Conversational Interfaces: He sees significant potential in bots to change the way businesses and the internet operate.
- AI as an Efficiency Driver: "It's going to be an efficiency driver, it's very clear, and companies that can incrementally harvest that efficiency are going to do fabulously."[12]
- Skepticism of AGI: "The second you start talking about you know super intelligence or alternative intelligences...I think that is much more religion than practical."[12]
On Work and Life Philosophy
- Embrace "Type 2 Fun": "Type 2 fun 'completely sucks while you're doing it, but there's joy on the other side' (climbing mountains, marathons). Entrepreneurs need Type 2 fun experiences."[4]
- Practice Voluntary Hardship: Lessin sees value in undertaking difficult challenges, not for the love of the activity itself, but to build perseverance.[4]
- Nobody Knows What They're Doing: A lesson from his time at Bain was that even prestigious companies "have no idea what you're doing," which can be a liberating realization.[4]
- The Power of Writing: "Writing is thinking. If you can't write, you can't think."[4] He also emphasizes the importance of writing publicly to create a record of your intellectual journey.
- Joy as a Competitive Advantage: "I just don't think that in the long run, angry people win." He believes that being around optimistic people who find joy in their work is a key to success.[4]
- The Importance of Family: "Putting family first, and certainly kids first within the family, is just something I really believe in."[3]
- Be Early or Be Late, Don't Be on Time: This quote encapsulates a strategic approach to timing and opportunity.[4]
- The Freeing Power of Metrics: While initially skeptical, Lessin came to appreciate how clear metrics can empower teams with the freedom to innovate on how they achieve their goals.[5]
- Find Your People: "One of the most important things when you're doing anything...is you need to find your people which means both finding people who love it and it's actually good when lots of people hate it."[13]
Additional Learnings and Insights
- On Tech Layoffs and Talent Hoarding: Big tech companies "didn't need those people, they were hoarding the talent. It was an option bet."[12]
- The Problem with Public Markets: "Going public kind of sucks...the public markets do face an adverse selection problem" because the highest-quality companies often have less need to go public.[2]
- Investing in Creators: His firm, Slow Ventures, has been experimenting with investing directly in creators, buying a percentage of their future earnings.[6][10]
- The Shift from Communities to Cults: Lessin observes that online spaces have evolved from open communities to more insular "cults."[11]
- The Internet as a Medium for Extremes: "The internet is a medium for being extreme and causing extreme emotions in lots of directions."[13]
- The Story Behind "Slow Ventures": The name reflects the reality that "many 'overnight successes' actually start slowly and take time to ramp up."[10]
- On His Role at The Information: Lessin is a regular columnist for The Information, a publication founded by his wife, Jessica Lessin, where he writes his "Modest Proposals."[11]
- On Backing Solana: Slow Ventures was a very early investor in Solana, a position that returned almost 2000x for the fund.[4][5]
- The Importance of Being Accessible: Slow Ventures aims to be highly accessible to founders for strategic advice, preferring quick consultations over deep operational involvement.[10]
- The Value of a Contrarian View: Many of Lessin's most successful investments and insightful takes come from a willingness to go against the prevailing consensus.
- From Angel Investor to Fund Manager: Lessin began his investing journey by making angel investments with friends, which eventually evolved into the formal establishment of Slow Ventures.[10]
- On Personal Growth: He left Facebook because he "really didn't want to be a manager" and sought to do something "more authentic to myself."[3]
- The Power of Screenshot Essays: He uses this format on X (formerly Twitter) to provoke reactions with a headline while ensuring the full context of his argument travels with every share.[13]
- On the Creator Economy: Lessin believes that providing capital directly to creators allows them to invest in their brand and explore various monetization strategies over the long term.[11]
- The VC-Founder Relationship: He emphasizes the need for VCs to have patience and respect for founders who are pouring their lives into their ideas, even the ones that seem "silly or stupid."[3]
- The Long-Term Perspective: The philosophy behind Slow Ventures and many of Lessin's learnings points to a focus on patience, long-term growth, and the non-linear path to success.[10]
Sources:
- Sam Lessin's Website: https://www.samlessin.com/[14]
- The Information Articles: https://www.theinformation.com/reporters/sam-lessin
- Muck Rack Profile (with links to articles): https://muckrack.com/sam-lessin/articles[6]
- Forbes Profile: https://www.forbes.com/profile/sam-lessin/[15]
- Various Podcast and Video Interviews: As cited throughout the list.
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