Podcast Summary: How I Invest with David Weisburd
Episode 275: Does Grit Actually Matter in a GP — or Is It Just a Good Story?
Date: January 5, 2026
Guest: Larson (Founding GP of Harpoon Ventures)

Main Theme

This episode explores the true value of grit, resilience, and mental toughness in the world of venture capital, both at the individual (GP) and portfolio company/founder level. David Weisburd (host) and guest Larson—a former Olympic swimmer, Navy SEAL, and now GP at Harpoon Ventures—discuss whether grit has intrinsic value in success or is simply a narrative device, and how experience in extreme environments translates into investing, leadership, and company building.

Key Discussion Points & Insights

The Value of Embracing Difficult Challenges

• Grit in Life and Venture:
  • Larson attributes much of his personal and professional fulfillment to consistently choosing the "hardest things" (00:31).
  • Draws parallels from Olympians, Navy SEALs, and iconic founders like Elon Musk, arguing that remarkable accomplishment often appears irrational at the outset.
• Intrinsic Value of Hard Things:
  • "Even if you're going through hard things where the end state may not be obvious...by training yourself to know you can overcome life's adversities, that has a benefit in and of itself." – Larson (01:54)
  • Warns against pursuing tough endeavors without higher purpose; mental fortitude should be matched with impactful goals, not just challenge for its own sake (02:45).

Parenting, Self-Compassion, and Coaching the Self

• Translating Lessons to Parenting:
  • Discussion on teaching resilience to children and why adults should “coach themselves as they would coach their kids” (04:10).
  • Reflections on balancing self-criticism and self-grace: "There’s been some days where I wake up and I feel so down on myself...I would never in a million years want my kids to feel that same way." – Larson (04:35).
• Behavioral Conditioning:
  • Comparison of pushing through adversity in sports to overcoming business plateaus and setbacks (05:51).

Cohort Effects and “Sixth Gear”

• Importance of Being in a Cohort:
  • Shared suffering/effort with a group (e.g., investment banking analysts, startup founders) creates crucibles that form lasting resilience (07:33).
  • "All people, especially young men, benefit from this ascension past something that’s really, really difficult." – Larson (08:00).
• Unlocking “Sixth Gear”:
  • Major formative experiences (SEALs, Olympics) can permanently provide an extra level of resilience, but maintaining it amid life complexity is challenging (09:09).

Endurance and Resilience for Investors

• Mental Toughness in VC:
  • "Things are never as good as you think, and they're never as bad as you think either." – Advice from Peter Levine to Larson (10:09).
  • Resilience as an investor is shaped by setbacks, missed deals, and being adaptable to an evolving market (11:05).
• Avoiding Complacency:
  • "If you’re overly wedded to just doing things one way and you don’t have the resilience...to maneuver with the market, that’s where you can get into trouble." – Larson (12:09).

Harpoon Ventures’ Edge

• Unique Right to Win:
  • Focus on national interest tech for the US and its allies, helping deep tech startups penetrate government markets—a strategic wedge not matched by traditional VCs (12:38).
  • Over $1B in contracts facilitated for portfolio companies since inception (13:21).
• Strategic Collaboration:
  • Collaborative stance with mega funds (A16Z, Lightspeed), but now also focuses on earliest-stage deals (15:05).

On Mentorship, Leadership & Empowerment

• Importance of Being Led:
  • True leadership is about “servant leadership” and putting the team first, as learned in the military (16:48).
  • "Leaders eat last...you got that respect by letting your people be taken care of before you are." – Larson (17:10).
• Empowering Others:
  • Reference to Keith Rabois’ ‘barrels and bullets’ framework: great leaders can empower the “middle” to become more entrepreneurial (18:43).
  • Worst leaders are those who ignore critical input; best solicit and synthesize diverse perspectives (19:47).
  • "Having the humility to be told from a bottoms up standpoint, I think, makes all the difference..." – Larson (20:28).
• Mission over Ego:
  • "Do you value the mission more than your own ego?" – David (21:05).
  • "Everybody's in love with their own idea...just recognizing that and parking it helps you accomplish more." – Larson (21:10).

Venture’s Power Law & Risk

• High Hit Rate vs High Impact:
  • "Almost every idea that we're pitched is a good idea...but we almost definitionally need to look for things that appear to be bad ideas." – Larson (23:07).
  • Emphasis on searching for non-consensus, “bad at first glance” outlier ideas that could change markets—even if their expected hit rate is lower (25:07).
• Venture as an ‘Access’ Not Asset Class:
  • "Venture capital isn't an asset class, it's an access class." – Learned from Ravi at Lightspeed (25:46).
  • Only outcome that matters is the magnitude of winners, not quantity of losses (25:07).
• Founders Pick Investors:
  • "When I have LP conversations, like 'How did you pick this company?' It's like—this company picked me!" – Larson (26:40).
• Best VCs Are Fast Followers:
  • "Best founders are six to twelve months ahead of best investors in the world...venture investors are the fast followers." – Larson (31:40).

Product-Market Fit & Team

• On Product-Market Fit:
  • Draws on learnings from John Vrionis (Lightspeed) and Andy Rachleff (Benchmark): A 10x innovation + a desperate customer are prerequisites (28:19).
  • It’s crucial to find referenceable customers within a focused cohort before market expansion.
• Team Above All:
  • The “three-legged stool”: world-class team, desperate market, new tech unlock. But the right team can compensate for the other two, especially since they adapt (31:40).
  • Market size still matters: “Market always wins. You can have the best team in the world, but if you’re operating in a crummy market… you’re dead to rights.” (34:27).
• Knowing When to Pivot:
  • Founders can be so tough that they overcommit to small markets; sometimes “firing” existing customers is required to chase bigger opportunities—an act demanding immense resilience (35:30).

Building Mental Toughness on Purpose

• How to Condition Grit:
  • “The only easy day was yesterday”—adopt a mindset preparing for daily new challenges (37:36).
  • Put yourself in uncomfortable, low-stakes settings to build calluses for when stakes rise—akin to SEAL training (37:58).
  • “The things you’re most proud of…were probably the hardest ones.” – Larson (39:10).

Decision-Making, Optimism, and Perspective

• Reframing Challenges:
  • On a hypothetical 150-question LP questionnaire: “At face value, I did not expect this and I’m not excited…but what a blessing.” – Larson (40:23).
  • Optimism flows from gratitude for opportunity and reframing tough asks as affirmations of worth (41:51).
• Advice for Starting Out:
  • “I wish I knew what a limited partner was.” – Reflecting on being an industry outsider as an advantage (43:03).
  • “Rules are the enemy of returns”—sometimes your best deal breaks all your rules (advice from Chris Dixon/Peter Thiel; 43:50).

Notable Quotes & Memorable Moments

• “The things that are most difficult in life are the ones where you feel the most fulfillment.” – Larson (00:31)
• “Just treat yourself as you would your kids—and coach yourself that way.” – Larson (04:10)
• “Things are never as good as you think, and they’re never as bad as you think either.” – Peter Levine, relayed by Larson (10:09)
• “Venture is a game of outliers…based on an outlier deal where you probably broke every single rule you set for yourself.” – Advice from Chris Dixon/Peter Thiel, via Larson (43:50)
• “Venture capital isn’t an asset class, it’s an access class.” – Ravi (Lightspeed), via Larson (25:46)
• “Venture is 99% saying no and 1% begging.” – David quoting an (anonymous) tweet (27:34)
• “We do this not because it's easy, but because we thought it would be easy.” – Start-up flag anecdote (46:07)

Timestamps for Key Segments

• [00:31] – Embracing difficult challenges: Olympics, SEALs, venture, fulfillment
• [01:54] – Intrinsic benefit of tough pursuits and purposeful challenge
• [04:10] – Parenting, self-coaching, grace for oneself
• [07:33] – Cohort effects: why shared hardship matters (e.g., investment banking as crucible)
• [09:09] – “Sixth gear”: sustaining drive as life diversifies
• [10:09] – Peter Levine's “never as good or bad as you think” advice
• [12:38] – Harpoon's value proposition and strategic focus
• [15:15] – Securing backing from A16Z and Lightspeed
• [16:48] – Servant leadership: lessons from the SEALs
• [18:43] – ‘Barrels and bullets’ leadership; empowering teams
• [23:07] – Hit rates vs outlier ideas in venture
• [25:46] – Venture as access class, not asset class
• [28:19] – Product-market fit wisdom from John Vrionis/Andy Rachleff
• [31:40] – Team > product/market at early stage
• [34:27] – Why market always ultimately wins
• [37:36] – Building “grit light”: engineering discomfort for resilience
• [40:23] – Reframing challenges as opportunity
• [43:03] – If starting over: “wish I knew what a limited partner was” & rules as enemy of outlier returns
• [46:07] – On why people start companies: “We do this not because it's easy, but because we thought it would be easy”

Conclusion

Larson and David’s dialogue masterfully covers the role of grit, the importance of adaptability, the unique demands and strategies of venture capital, and the psychological frameworks that differentiate great founders, leaders, and investors. As succinctly summed up in the SEAL motto and the world of startups: “The only easy day was yesterday.”