Leadership Lessons from a Serial Entrepreneur | Dennis Crowley, Co-Founder at Hopscotch, Foursquare & Dodgeball

Earlier this week we were thrilled to welcome serial entrepreneur Dennis Crowley to Enrich for a fireside chat. While Dennis is most well-known for co-founding Foursquare, he’s someone who is always exploring new ideas and endeavors. Right now, that looks like building a soccer club and leading his current startup, Hopscotch Labs.

With Hopscotch, Dennis is returning to consumer-first innovation, building BeBot, an audio-based AI assistant designed to surface real-world serendipity through AirPods. Unlike apps that trap users in screens, BeBot interrupts you in the moment (“there’s a vintage skateboard shop downstairs — go check it out”) — intentionally proactive, even if sometimes imperfect.

If you’d been there, here’s what you’d still be thinking about:

• Start consumer-first if that’s your DNA. Dennis admitted he’s no “enterprise visionary.” His instinct is to build playful consumer experiences first, and let opportunities for scale (like APIs and data) emerge later. If your natural inclination is to build for humans and not businesses, don’t fight it — we need both.

• Culture shifts when business models shift. When the business was forced to pivot, Dennis has to shift all of Foursquare from being oriented around a "“shiny” consuer app to an enterprise business. As a result, there was attrition, as talent who were there for the consumer app moved on. Leaders must over-communicate the vision and be intentional about culture during pivots.

• Leadership requires honesty about burnout. Dennis’s turning point at Foursquare was admitting to investors, “this job is hard, I don’t like it, and I feel like I’m failing.” That openness paved the way for redefined roles and longevity — and focusing on finding the right leadership role for that particular stage of the company and moment in time.

For the complete event notes and a recording, apply to join Enrich.