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May 13, 2025 45 mins

What if one of the boldest early-stage investors in frontier tech got her start chasing down a job over yoga pants and no website?


Kristina Simmons, founder and managing partner of Overwater Ventures, began her career launching Lululemon’s e-commerce before rising through the ranks at Andreessen Horowitz and Khosla Ventures. Now she’s channeling that rare mix of brand, ops, and VC experience into Overwater, a fund built to help science-backed startups become world-shifting companies. From AI-powered IVF to wildfire prevention and next-gen food systems, Kristina is betting on bold ideas—and even bolder founders.


In this episode, we dive into her nonlinear path through tech and retail, how she evaluates deep tech at the earliest stages, and why she believes great investors need both a thesis and a gut.


Key themes we cover:


- Why smaller funds are outperforming giants—and what it means for founder investor fit

- The art (and science) of translating white papers into winning pitches

- How Overwater blends A16Z scale with Khosla grit—and why her fund is built like a startup

- What founders get wrong about commercialization—and how to fix it

- Why storytelling, not specs, closes rounds—and how to nail it without the hype


From Vancouver yoga floors to Silicon Valley boardrooms, Kristina’s journey proves that great venture firms aren’t born—they’re built, brand-first, by people who know exactly when to ride the wave and when to change the tide.


Chapters:

Welcome & Kristina Simmons Introduction (00:01 – 00:40)

Why Start a New Fund Outside of Big VC (00:41 – 02:35)

The Case for Smaller Checks and Leaner Startups (02:36 – 03:52)

Early Hustle: From Michigan to Lululemon (03:53 – 06:15)

Entering Venture via Andreessen Horowitz (06:16 – 07:43)

Lessons from Khosla Ventures (07:44 – 10:54)

Overwater's Investment Thesis and Framework (10:55 – 15:15)

Problem-First Thinking and Prepared Mind Approach (15:16 – 19:43)

Portfolio Highlights: Fertility, Food, Fire Prevention (19:44 – 22:18)

Redefining Consumer vs. Enterprise in Deep Tech (22:19 – 23:28)

Preventative Health and Real-Time Biomarkers (23:29 – 26:24)

AI, Longevity, and Drug Development (26:25 – 29:15)

Pitching Deep Tech: Common Founder Mistakes (29:16 – 30:44)

Hands-On VC vs. Passive Capital (30:45 – 33:09)

Fund Strategy: Lessons from Fund I (33:10 – 34:54)

Overwater Brand and Founder Support Model (34:55 – 36:24)

How Founders Should Build Brand Early (36:25 – 38:44)

Underhyped Frontier Tech Trends (38:45 – 40:30)

Why Now Is a Great Time for Big Bets (40:31 – 41:59)

Fundraising Strategy & Investor Psychology (42:00 – 43:36)

Final Advice & Rapid Fire Round (43:37 – 45:48)


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