Founder Mode Episode 26 - How Not to Run a Startup with Bobby Evans

In this episode, we flipped the script. We didn’t just ask, “What works?” Instead, we focused on what breaks startups. We looked at what stops momentum and which smart choices can fail.

As I put it at the start of the show:

“Today's episode is a little different. We're not talking about what to do. We're going Munger style and learning through inversion.”

Bobby Evans, a fast riser in crypto and sports betting, joined us. He shared his mistakes and the traps founders often face. Along the way, Jason and I added our own scars and stories from years of building.

Mistakes That Sneak Up on Founders

Over-Hiring Too Early

As Bobby shared, one of the fastest ways to sink a young startup is over-hiring. It feels right at the time, but you end up with high burn, slow decision-making, and painful layoffs later.

His advice: start lean, use contractors, and hire carefully.

Bonus Wars and the Race to the Bottom

In competitive markets, companies try to outdo each other with incentives. Bobby admitted his team once offered 50% cashback, only to realize it destroyed margins.

Incentives need a clear strategy. Without it, they cause churn instead of loyalty.

Building Features Nobody Wants

Bobby spent six months on user profiles. In the end, he found that customers didn’t care. By the time it launched, it was irrelevant.

“What's maybe a product feature that you once thought was brilliant, but then turned out to be a complete waste of time?”

Shiny features aren’t always valuable. Ship fast, test with users, and move on.

Vanity Metrics Are Dangerous

Big numbers can look great on paper—like 12,000 weekly players for a free-to-play app. But when zero turned into paying users, those numbers didn’t matter.

“Ignore those vanity metrics. Focus on conversion and like what's the real ROI of the value.”

Founders Need Thinking Time

Even with lean teams, founders often try to be everywhere at once. Packed calendars create busywork, not strategy.

Bobby said, “Taking time to think and grow is more important than being busy.””

“Delegate and protect thinking time. You can have a packed calendar, but you need to have time to think and relax and really understand strategy.”

5 Key Takeaways

Over-hiring backfires. Keep the team lean; use contractors before going full-time.
Incentives can create churn. Bonus wars are a race to the bottom.
Ship an MVP fast. Don’t waste months polishing features no one wants.
Ignore vanity metrics. Conversion and real ROI matter more than raw numbers.
Protect founder time. Strategy comes from focus, not from filling your calendar.