(0:00) Jerry Colonna joins Jason (1:14) Jason's early internet days and first taste of money/power (10:08) Corient - Speak with one of Corient's wealth management advisors today at http://corient.com/ (11:08) Jerry's journey as a venture capitalist during the peak Dot-com era to founder coach (18:32) What pushed Jerry to his limits, and how did Jerry overcome his depression (23:36) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (24:56) Jerry's Book "Reboot" and what Jerry sees drives founders (28:54) How to transition from a founder to a CEO (38:31) Coda - Get started for free at https://coda.io/twist (40:03) Finding the right motivation and the steps to being an enlightened leader (57:01) Acute issues that founders contact Jerry about Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Check out Reboot: https://www.reboot.io/reboot-leadership-and-the-art-of-growing-up Check out reunion: https://www.reboot.io/reunion-leadership-and-the-longing-to-belong X: https://twitter.com/Jason https://twitter.com/jerrycolonna LinkedIn: https://www.linkedin.com/in/jasoncalacanis https://www.linkedin.com/in/jerry-colonna-reboot Thanks to our partners: (10:08) Corient - Speak with one of Corient's wealth management advisors today at http://corient.com/ (23:36) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (38:31) Coda - Get started for free at https://coda.io/twist Listen here: Apple: https://podcasts.apple.com/us/podcast/this-week-in-startups-audio/id315114957 Spotify: https://open.spotify.com/show/6ULQ0ewYf5zmsDgBchlkr9 Overcast: https://overcast.fm/itunes315114957/this-week-in-startups-audio More from us: Twitter: https://twitter.com/twistartups Instagram: https://www.instagram.com/thisweekinstartups Official site: https://thisweekinstartups.com/ Subscribe to our YouTube to watch all full episodes: https://www.youtube.com/channel/UCkkhmBWfS7pILYIk0izkc3A Subscribe to TWiST Clips for all the best moments: https://www.youtube.com/channel/UCS7tJlcUA6PzVHEMo-X7ddg #startups #entrepreneurship #investing #angelinvesting #tech #news #business