What if AI made you more present, not more addicted?
Dennis Crowley (founder of Foursquare) shares field-tested lessons from 20+ years building in NYC, why he prefers NYC to SF, and the thesis behind Hopscotch Labs and Beebot: ambient, context-aware experiences designed to push you into the real world instead of into a feed. We also get tactical: notebooks, hiring, early-stage chaos, and how to stay in the game when you feel burned out.
(00:00) Intro — A founder’s field notes from NYC
(03:05) Why writing things down changes your brain
(09:10) “You fall to the level of your systems”
(14:45) From Dodgeball → Foursquare → Hopscotch Labs
(19:35) BeeBot — proactive, wearable AI and why it’s hard
(27:15) Hiring for uncertainty: side projects, skill, and resilience
(34:30) NYC tech evolution — capital, talent, and density
(41:10) How to battle burnout
Follow Dennis Crowley on LinkedIn: https://www.linkedin.com/in/dpstyles/
Follow Dennis Crowley on Substack: https://teendrama.substack.com/
Hopscotch Labs: https://hopscotchlabs.co/
BeeBot: https://dens.medium.com/say-hello-to-dj-beebot-592cdc1f1704
Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing
Join the Executives Unplugged Inner Circle for free coaching via email: https://execs.tv
Subscribe to the show:
YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM
Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN
Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263
