Investor Interviews

Interviews and lessons from studying investors

Apr 11, 2025

📶 Bryce Roberts (Founder @ INDIE) on efficiency, the pursuit of revenue-per-employee, and escaping the venture rat race

Efficiency and growing revenue-per-employee, automating the back office vs. front office, why creators are bad at pursuing the right ways to monetize their audience, and how seedstrapping changes venture math

Mar 27, 2025

📶 Kevin Novak (GP @ Rackhouse) on new business models and AI-first businesses

Founder errors of the past and present, second-order effects of intelligence becoming cheaper, how to think about investment time horizons in today's world, and why infrastructure matters more than algorithms

Mar 13, 2025

📶 Leo Polovets (GP @ Humba Ventures) on what makes a great LP, attributing luck to seed investing, and using transparency to your advantage

What GPs look for from their LPs, making the case for venture investing vs. other asset classes, and some philosophy around reserves and follow-on investments

Mar 11, 2025

📶 Sean Doolan (GP @ Virtue) on healthcare complexities, scaling a fund, and a fork in the road for junior investors

Healthcare vs. SaaS investing, getting to conviction quickly, and filling a gap in the funding market

Mar 6, 2025

📶 Ashley Smith (GP @ Vermilion Cliffs Ventures) on operators-turned-investors, the evolution of engineering roles, and how GTM is changing in 2025

Non-traditional paths to become a GP, secondary effects of AI co-pilots, hiring the unhireable, and why you can't take a one-size-fits-all approach to GTM strategy

Feb 26, 2025

📶 Zoe Weinberg (GP @ ex/ante) on agentic tech and reasons to be optimistic about AI

Pre-seed capital, signaling risk, and what changes as it becomes easier to spin up an MVP, the threats and opportunities in AGI (and why a lot of the noise is overhyped), and how alpha is created through unique lived experiences

Feb 14, 2025

📶 Jeff Morris, Jr. (GP @ Chapter One) on growing your internet surface area

Publishing on the internet, building leverage through teambuilding, and scaling a fund into an institution

Feb 10, 2025

📶 Charley Ma (GP @ Pathlight) on how to think as a thematic GP

The choice to be a thematic investor, the challenge of thinking over long time horizons with the pace at which the world is changing today, takeaways from moving upstream and warranting more ownership, how the role of emerging managers will change over the next ten years

Jan 31, 2025

📶 Mack Healy (GP @ KdT Ventures) on the non-glamorous parts of venture

Incubating companies while operating a fund, common misconceptions about running a venture fund, questions he wishes founders would ask more often, overlooked opportunities

Jan 22, 2025

📶 Maya Bakhai (GP @ Spice Capital) on true signal, seed fund portfolio construction, and the opportunity for being non-consensus

Avoiding venture groupthink, gaining conviction at pre-seed, investing in "scar tissue" zones, math on why you're probably not as good at picking as you think

Jan 10, 2025

📶 Tim Chen (Managing Partner @ Essence) on the infrastructure opportunity

Reasons to be bullish on developer tools, advantages and disadvantages of being a solo GP, and the right time to approach institutional capital

Dec 17, 2024

📶 Rex Woodbury (Founder & Managing Partner @ Daybreak) on the trends changing the world

Trends on where the world is heading, unconventional investment theses, pairing a newsletter alongside a fund, and some hard truths about VC

Dec 10, 2024

📶 Nik Milanović (GP @ The Fintech Fund) on turning media into equity

Converting a media brand into an investment firm, the opportunity zones for fintech over the next decade, and some non-consensus bets that he’s placing

Apr 26, 2024

outlier frameworks: how tier-one investors think

96 mental models used by investors at Sequoia, Benchmark, Accel, and others

Mar 21, 2024

📶 13 Lessons from Elad Gil (Angel Investor in Notion, Coinbase, Airbnb)

How to choose a career, what makes a great executive, and why you should back "revenge" founders

Mar 7, 2024

📶 25 Lessons from Jeremy Giffon (Managing Partner @ Tiny)

The irony of outlier expectations, why audiences are still underrated, the best types of business, and discovering God's purpose for you

Feb 16, 2024

📶 21 Lessons from David Frankel (Managing Partner @ Founder Collective)

The most profitable route to wealth, why trends don't matter, and how to create FOMO for investors

Feb 8, 2024

📶 21 Lessons from Erik Serrano (CEO @ Stable Asset Management)

A masterclass on how to invest into investment firms

Jan 25, 2024

📶 19 Lesson from Alexis Ohanian (Founding Partner @ Seven Seven Six)

Reputation as a proxy for future returns, the power of process design, how you should spend your time while building zero-to-one, and why the first 100 users determine company direction

Jan 18, 2024

📶 25 Lessons from David Sacks (Founding Partner @ Craft Ventures)

How to think about startup sales, solving unit economics before growth, and why chaos is a good thing

Jan 5, 2024

📶 15 Lessons from Doug Leone (Managing Partner @ Sequoia)

Winning through simplicity, finding a person's drive, investing in outliers, and how to earn trust

Nov 9, 2023

📶 16 Lessons from Ben Horowitz (GP @ a16z)

Decision-making velocity, creating motion through stories, skills vs. experience, and the two types of friends every person needs

Nov 2, 2023

📶 15 Lessons from Bryan Schreier (Partner @ Sequoia)

The downside of specialization, two questions to ask when choosing investors, developing a service-first approach to investing, and how to think about board meetings

Oct 26, 2023

📶 17 Lessons From Bill Gurley (General Partner @ Benchmark)

The most important KPI metric, acknowledging luck, what makes a great marketplace, and why being right doesn't always pay

Oct 19, 2023

📶 16 Lessons from Brad Feld (Partner @ Foundry Group)

Expanding startup investing out of Silicon Valley, networks of trust, benefits of flying under the radar, and what the market rewards in a downturn