Ben Lerer, Managing Partner and Founder of Lerer Hippeau, has built one of New York's most influential early-stage venture firms across nine funds and nearly $1.5B in AUM. In this VC edition of the GTMnow podcast, Ben sits down with Max and Paul to unpack how he actually picks founders, why he wants to be the "worst investor" at his own fund, and the contrarian belief that backing good, sensible businesses is a mistake.Ben got his start in media, building Thrillist before it merged into Group Nine, then turned those relationships and that operator empathy into a venture career writing early checks into companies like Warby Parker and Casper. He shares what's changed about winning deals in a more competitive, sharp-elbowed market, how Lerer Hippeau runs its investment committee on conviction rather than consensus, and the process failure behind passing on Peloton.We also get into the debate every investor is wrestling with right now: the crazy, fast-moving AI-native founder versus the second or third-time operator with deep domain expertise, and why the answer is rarely a silver bullet.A real venture-nerd conversation on firm building, IC decision-making, founder selection, and what it takes to chase the power law.Topics covered:- The "worst investor at my own fund" philosophy- Conviction vs. consensus in the investment committee- Why Lerer Hippeau funds "crazy" founders, not good companies- The Peloton miss and what it revealed about process- From Thrillist and digital media to venture capital- AI-native founders vs. domain experts- How to win competitive deals as a smaller firmChapters:00:00 Intro00:52 Max and Paul on the episode: IC process and founder selection14:36 Conversation with Ben Lerer begins15:02 Nine funds, $1.5B AUM, and the early-stage strategy23:00 From Thrillist to venture: the media springboard28:00 What's changed in picking founders and winning deals33:00 How the investment committee grew and evolved37:40 The "magic" deal and chasing high-conviction bets50:43 Why Ben wants to be the worst investor at his fund53:00 Funding crazy people, not good companies51:35 Yankees or Mets?Connect with Ben Lerer: https://x.com/BenjLererLinkedIn: https://www.linkedin.com/in/benlerer/Connect with Max: https://x.com/hackitmaxlinkedin.com/in/maxaltschulerListen on Apple and Spotify, and subscribe for more GTMnow VC editions.Visit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.