Field Notes from 20 Years of NYC Startups

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.Chapters(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 burnoutConnect with Keith or DennisFollow 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-592cdc1f1704Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowingJoin the Executives Unplugged Inner Circle for free coaching via email: https://execs.tvSubscribe to the show:YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcMSpotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKNApple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263