Founder Mode Episode 34 - When Founders Show Up

In this episode of Founder Mode, Jason and I explored a topic that many startup builders miss: events.

Should founders stay heads-down and build?

Or show up, sponsor booths, and pitch live?

We just got back from a big healthcare AI conference in Nashville, and we learned a lot. Our team went all-in, and it changed how I think about events forever.

“Founder mode events mean this: Don’t just attend—activate.”

— Kevin Henrikson

Here’s what worked, what didn’t, and how you can turn events into real business wins.

5 Key Takeaways

1. Treat Events as High-Leverage, Not Distractions

Events can feel like a waste until they’re not. But you have to treat them like product launches. Plan ahead, invest deeply, and show up with purpose.

“You’re sacrificing the team’s time. So go big enough to make it count.”

2. Pick Conferences Where You Serve 100% of Attendees

It’s not about being everywhere. It’s about being in the right room. At this event, every single attendee could be a Pretty Good AI customer. That’s rare and powerful.

3. Go All-In on Presence and Brand

We didn’t just show up. We secured the largest booth. We created a golf theme around our “Pretty Good AI” name. Plus, we brought the whole team. The result? 10–20% of the conference attendees came by and remembered us.

“At the very least, it’s a good all-hands meeting for the team.”

4. Pre-Work and Follow-Up Matter More Than the Event Itself

You can’t just show up cold. We hosted webinars, made materials, set up our CRM, and booked meetings in advance. We tracked every touchpoint during the event. This helped us with proper follow-up.

“Don’t just tell me what it does, show me. Then let people experience it.”

5. Owner Mentality Wins

Other booths shut down early. Some offered $100 gift cards to get attention. But our team was first in, last out every day. And they’re engineers, not sales reps.

“They weren’t acting like owners. That hurts your brand.”