After Dot-Com, SaaS, and Crypto: Why Venture Capital Still Feels Fun in the AI Era

I’ve been in this business long enough to watch people fall in love with it, grind through it, and eventually move on. Some retire. And I’ve seen a new generation of VCs enter.

I used to wonder why all the transition. I think I understand it a little better now.

Arthur Brooks writes about this in his happiness research – the idea that the first half of a career is driven by achievement and accumulation, and the second half, if you’re lucky, shifts toward meaning and contribution. The people who struggle in the second half are often the ones who never made that transition.

They kept chasing the same metrics that worked at 35, and somewhere around 50 they looked up and wondered why it felt hollow. I think about that a lot in the context of venture. Its a fast business in one respect, with exceptionally long feedback loops.

There are things about this job that have genuinely gotten harder to love. The market has gotten more transactional. Founders pitching five VCs simultaneously, optimizing for speed and terms. VCs running parallel processes, never fully committing until they have to. It’s a bit like dating on Tinder!

I also understand now why some people retire from this business earlier than expected. It’s not always burnout in the obvious sense. It’s more subtle -somewhere along the way the craft gets crowded out by the mechanics. When that happens, the fun quietly leaves the room.

But here’s what’s pulled me back, and honestly reinvigorated me more than I expected.

AI tools have changed how I work in ways I didn’t anticipate. Research that used to take hours takes minutes. I can go deeper, faster, on more ideas. That sounds operational but it actually gives me more time for the part of the job I love – the conversation, the thinking, the people.

I’ve also been more intentional about my mindset walking into founder meetings. At some point I realized I was showing up with a filter – pattern matching, looking for reasons to pass, running the checklist. I’ve tried to replace that with something closer to genuine curiosity. Every founder knows something I don’t. Every meeting is a chance to learn something about a market, a problem, a person. When I walk in with that attitude, the whole thing feels different.

Practically, four days in person a week has been the right rhythm for me. Enough presence to feel connected, and a day without 2x subway rides 😉

As someone who lived through the dot-com era, mobile, SaaS, crypto – being ringside for AI is a privilege. Every week something shifts. Every meeting I’m learning something I didn’t know the week before. That part I’d do for free.

So yes – still fun (mostly). But it’s a different kind of fun than it was a decade ago. Less about the chase, more about the depth. More Brooks second half than first.