🎉 50 episodes of
@InvestNStartups! We’re marking the milestone with a special episode packed with the biggest insights and hardest lessons I’ve learned from hosting the show.
We dive into the game-changing impact of AI on founders and investors, the fiercest debates shaking up venture, what I’ve completely reversed my thinking on, and my most contrarian take on VC.
Here's the longer breakdown of my conversation with good friend and guest host
@ChrisHillALX, host of
@MoneyUnpluggedP:
AI has been the defining force in venture since the show started in 2024. AI has changed how startups get funded, how fast they grow, and how lean they can be, helping revive venture after the post-2021 downturn.
The rebound has been real, but highly concentrated to the biggest winners. AI is also driving growth and efficiency at once. Startups can scale revenue much faster without scaling headcount the same way, pushing more value toward companies that pair strong demand with small teams.
One of venture’s biggest debates is around portfolio construction. I talked about the tension between ultra-diversified investing, which improves the odds of catching a unicorn at the expense of diluting its impacts to returns, and concentrated investing, which can raise the quality bar and leave more time to support founders.
Another major split is hot deals versus non-consensus deals. Some investors want the most in-demand founders regardless of price, while others hunt for overlooked opportunities in less fashionable markets and sectors.
Several guest conversations changed my thinking. One example was
@MacConwell on reserves: instead of setting aside large amounts for future rounds that may never materialize, I now favor a “fast follow” approach when conviction rises.
Another lesson, from
@nikiscevak, was the importance of finding your tribe with fundraising. Rather than trying to change minds, it is more effective to build a clear identity and attract founders and LPs who already share your worldview.
My most contrarian take is that ownership targets are overrated. What really matters to LPs and fund performance is not what percentage of a winner a fund owns, but what percentage of the fund’s capital is invested in the winner.
We also talked about emerging managers and the insights from guests on why they're able to outperform. Namely, that smaller, newer funds are hungrier, more focused, and more flexible.
Lastly, we talked about AI's role in VC. AI will increasingly help investors analyze startups, move faster, and operate with fewer people, even if judgment remains difficult to automate. AI will also narrow the gap between small and large venture firms by giving smaller managers better tools without requiring a large internal team.
Thanks to Chris for guest hosting this one, to all our listeners, and to the 50 amazing guests who have come on the show!