Power-law investing and expected value

Why do the people who build the most meaningful things almost always choose the hardest path and what does that unlock in the long run? In this episode, I talk with Larsen Jensen, Founding General Partner of Harpoon Ventures, about why deliberately choosing difficult problems builds the resilience, clarity, and long-term edge required to create category-defining companies. Larsen shares lessons from his time as an Olympic medalist and Navy SEAL, how those experiences shaped his investing philosophy, and why venture capital is ultimately a power-law game driven by rare outliers. We explore how founders develop mental toughness, how conviction is formed under uncertainty, and why great investors learn to trust teams more than models.

Highlights:

• Why hard things produce disproportionate personal and professional growth
• How resilience is built only through adversity, not theory
• The role of mental conditioning in elite performance
• Why venture returns come from rare exceptions, not rules
• How founders choose investors more than the reverse
• What it really takes to find product–market fit
• Why 10x solutions and desperate customers matter most
• The difference between vitamins and painkillers in startups
• Why the best teams are upstream of product and market
• How humility and mission matter more than ego

Guest Bio:

Larsen Jensen is the Founding General Partner of Harpoon Ventures, a venture firm focused on investing in companies that serve the national and economic interests of the United States and its allies. Before venture, Larsen was an Olympic medalist in swimming and served as a U.S. Navy SEAL, experiences that shaped his emphasis on resilience, mission, and long-term thinking. At Harpoon, he backs founders building frontier technologies across defense, cybersecurity, AI, and critical infrastructure, and is known for his founder-first, conviction-driven approach to early-stage investing.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

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Stay Connected with Larsen Jensen:

LinkedIn: https://www.linkedin.com/in/larsen-jensen/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (0:14) Larson Jensen's background and embracing challenges (1:56) Benefits and importance of overcoming adversity (4:38) Parallels between parenting, self-coaching, and mental toughness (7:33) Resilience across multiple careers and challenging environments (10:22) Mental toughness in venture capitalism and adapting to market changes (13:41) Harpoon Ventures' investment strategy and collaboration with major funds (16:30) Mentorship, servant leadership, and characteristics of successful founders (21:43) Distinguishing high beta vs. low beta investment ideas (24:06) Defining venture capital as an access class (27:27) Startups: Achieving product-market fit and the importance of team (34:38) Building mental toughness in founders and venture capitalists (38:57) Overcoming challenges for meaningful success (42:05) Advice for aspiring fund managers and the pitfalls of rigid VC rules (44:46) Resilience in successful individuals (45:46) Closing remarks