We're celebrating our recent 50th episode with a special conversation between host Joe Magyer and guest host Chris Hill of Money Unplugged. Chris interviews Joe about his lessons learned from the first 50 episodes, how AI is impacting startups and venture capital, what Joe has changed his mind about, and investing in startups, both the craft and the show. Joe and Chris also unpack how AI has reshaped venture in just two years—changing what it costs to start a company, how many people startups need to hire, how quickly they can build product, and why investors are again leaning into the category after a brutal post-2021 reset.

They revisit one of venture’s oldest debates: concentrated vs. diversified portfolios. Joe explains why some investors want as many shots on goal as possible, while others prefer to place fewer, higher-conviction bets so they can spend more time with founders and have a better chance of meaningful ownership in the winners. Another core tension in the episode is consensus vs. non-consensus investing. Joe talks through why the hottest deals often get hot for good reasons—great founders, fast growth, strong co-investors—but also why crowded rounds can compress returns and leave investors paying up for certainty that may already be priced in.

Finally, Joe also shares how hosting the podcast has changed his own investing style. Hearing other managers explain their frameworks pushed him to rethink rigid reserve strategies, become more flexible about follow-on investing, and focus more on doubling down when real conviction builds through direct founder relationships.

Investing in Startups is produced by Seaplane Ventures and (usually) hosted by Joe Magyer.