Sam Lessin is a Partner at Slow Ventures, with prior experience as Vice President of Product Management at Facebook and CEO of Drop.io. He has invested in notable companies like OpenPhone and Identiq, focusing on sectors like Direct-to-Consumer and FinTech. Lessin’s career highlights include serving as a key executive at Facebook, leading product management efforts, and successfully co-founding Fin. His current role at Slow Ventures involves investing in innovative startups across various sectors, showcasing his expertise in entrepreneurship and venture capital.

Watch our conversation on YouTube. And SUBSCRIBE!

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global’s team of 30,000 people around the world have the hustle and grit to deliver.

Order Our USA TODAY Best-Selling BOOK, The Score That Matters. “People spend far too much time obsessing about external scoreboards and not nearly enough time thinking about their internal one. Hawk and Cupps offer an important corrective, arguing the most important measure is whether or not you are living in alignment with your core values.” — Brad Stulberg, Best-Selling Author of Master of Change

Be part of “Mindful Monday” — Text Hawk to 66866

The Learning Leader Show

  • Key Learnings
    • The 4:30 AM Advantage – Sam’s father would be at his desk by 4:30 AM every day, saying, “It’s easy to look smart if you have a several-hour head start on everyone else.” Early work creates compounding advantages over time.
    • Either Be Early or Be Late, Don’t Be On Time – Father’s wisdom about timing and seasons. Start your career super early to get ahead, or strategically wait and come in later. Timing matters more than perfect preparation.
    • Joy as the Ultimate Competitive Advantage – “I just don’t think that in the long run, angry people win.” Look for joyful people in hiring and partnerships because joy is sustainable while anger burns out.
    • Type Two Fun Builds Resilience – Type 1 fun is enjoyable while doing it (rollercoaster). 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.
    • Practice Voluntary Hardship – Sam ran a sub-3-hour marathon and got a pilot’s license not for love of activities, but for “practice moments” of perseverance. Creates evidence that you can handle business adversity.
    • Right Person, Right Opportunity, Right Time – 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.
    • Write Publicly for Intellectual Receipts – “If you can’t write the check, write me the thesis and timestamp it.” Writing creates accountability, proves thinking ability, and builds reputation over time.
    • Nobody Knows What They’re Doing – Working at Bain taught Sam that even prestigious companies “have no idea what you’re doing.” This is liberating—you can figure it out too.
    • Big Things Take Time (Slow Ventures Philosophy) – 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.
    • Embrace Being Wrong Most of the Time – Seed investing means “you’re mostly wrong, you mostly lose money.” Success comes from being very right occasionally, not being right consistently.
    • The Solana 2000x Return Story – Put in $400K, returned 2000x to LPs. Success came from the intersection of thesis (looking for “Ethereum killer”) and relationships (following Raj Gokal through multiple startups).
    • Use Humor and Authenticity as Filters – Slow Ventures website looks like a law firm in tuxedos “on purpose.” If you don’t think it’s funny, “you’re not who we want to invest in.”
    • Writing Pushes Away Wrong People – “I really like to be not liked by the people I don’t want to work with.” Authentic writing attracts the right people and repels the wrong ones.
    • Manufacturing Hardship for Privileged Kids – “Tiger Dad” sports culture might be a misguided attempt to create necessary adversity for wealthy children who lack natural hardships.
  • I loved the throughline of this whole conversation being about his dad, working exceptionally hard, and having joy and excitement for the journey. Maybe it was the near-death experiences that his dad had that led to that mindset. Regardless, it’s something we can all learn from. We want to be around optimistic people who have joy and love for what they’re doing…
  • Nobody knows what they’re doing. We’re all figuring it out as we go. You’ll never learn unless you go out and do the thing. Figure it out as you go. Just get started. And iterate. Learn. Try again. And keep going.
  • Advice from Sam – Write publicly. You don’t know what you think until you get your thoughts out of your head onto the page. And if you publish them, you have a record of the journey. Also, you might attract someone to work with. That is how Jack Raines (guest on episode #539) caught Sam’s attention, and now they work together.
  • Useful Quotes:
    • “It’s easy to look smart if you have a several-hour head start on everyone else.”
    • “I just don’t think that in the long run, angry people win.”
    • “Either be early or be late, don’t be on time.”
    • “The right question is, is it the right person at the right moment?”
    • “Writing is thinking. If you can’t write, you can’t think.”
    • “I feel like a tenured professor of capitalism—responsible to make a lot of money over the long term by being very right every once in a while with permission to be wrong all the time.”
    • “One of the most insulting things you can call someone is a market participant.”
    • “The beauty of the internet is so big. The right people find you.”
    • “Big things take time.”
    • “Life’s short. Is this really what you’re spending your time on?”
  • Apply to be part of my next Learning Leader Circle.
Resources:

More Learning:

Episode 078: Kat Cole – From Hooters Waitress To President of Cinnabon

Episode 216: Jim Collins — How To Go From Good To Great

Episode #300: AJ & Keith Hawk – How To Instill Work Ethic & Curiosity In Your Children

Episode #303: General Stanley McChrystal – The New Definition Of Leadership

Time Stamps:

00:11 Sam’s Dad’s Unique Career Path

00:39 Life Lessons from My Dad

04:35 The Trade-offs of Hard Work

06:57 Betting on the Right People

07:23 The Importance of Joy in Success

10:39 Overcoming Hardships and Building Resilience

20:40 My Journey: From Harvard to Bain

26:06 Joining Facebook and Learning from Mark Zuckerberg

29:36 Balancing Joy and Competitive Spirit

30:15 The Story of Rippling and Parker

31:48 The Solana Investment Journey

34:33 The Importance of Writing and Public Thought

41:07 The Philosophy Behind Slow Ventures

52:54 Advice for Aspiring Venture Capitalists

55:46 Future Plans