Great Companies Need to Be Fun—It’s a Serious Signal
Sam Lessin
Context: Over the past few days, a series of conversations, reflections, and readings led me to a simple but powerful filter for evaluating startups: is it fun? In a time when early-stage venture is full of noise, fear, and performative seriousness, maybe the most underrated signal of potential is whether the founder, team, and customers are actually enjoying the ride.
Market Signal: Despite the downturn, successful founders (past and present) seem to share one trait: authentic enjoyment of the chaos. From Barry Piller’s profiles to Adam Neumann’s resilience, the ones who keep going are the ones having fun—not because it’s easy, but because they’re wired to love the grind. Meanwhile, most of the ecosystem feels stuck in un-fun drudgery, driven by FOMO, status anxiety, and meme-chasing.
Takeaways: Fun is a serious signal. It’s a proxy for founder-market fit, resilience, and long-term motivation. So we should be asking:
Does the founder actually love what they’re building?
Will the team enjoy working on it?
Will customers get joy, not just utility?
Is the journey—fundraising, competition, execution—energizing, not soul-sucking?
Fun doesn’t mean easy. But if no one involved is enjoying it, the ceiling is probably low.
Ask: If you’re seeing examples of teams, founders, or products where the fun is real—send them my way. I want to back what people love building.