Chris Redlitz is the Co-Founder and Executive Director of The Last Mile, leading a national movement across our country to provide in-prison technology education and post-incarceration mentorship to justice-involved people across the United States. Chris had previously sold a chain of running stores called Second Sole, founded and sold AdAuction.Com, co-founded Kicklabs, and co-founded Transmedia Capital, a fund and incubator that has helped launch and grow 38 tech companies to massive exits.

After spending his young-adult years on adventures around the world, including a 3-person sailing trip to Hawaii with no digital navigation equipment, Chris followed his passion for ultra-running and founded Second Sole, a retail store in California for high-level running equipment. Chris’ leadership in that space caught the attention of the rapidly growing sportswear giant Reebok, and Chris' meteoric rise in Reebok and his instrumental role in its massive IPO was the first of many profound successes in his life. Sensing the impending dot-com boom, Chris ventured into the digital realm at the perfect moment, leading to multiple successful acquisitions.

Throughout the interview, Chris shares personal stories and anecdotes that shed light on the realities of entrepreneurship. From the pain of a failed IPO to the importance of having a supportive partner, Chris' stories captivate and inspire listeners. Chris' experience and wisdom offer valuable lessons and insights for navigating the challenges and opportunities that come with building a business.

OUTLINE:

(00:00) Intro
(2:00) Early years as a rebel
(6:40) Dropping out college to sail to Hawaii
(13:00) Where my rebellious spirit came from
(16:30) Becoming addicted to running and opening a running store
(19:00) Joining Reebok as they grew from $10M to $4B
(21:41) Why Nike succeeded where Reebok failed
(24:04) Transitioning into the Dot Com Boom with AdAuction.com
(27:00) What the Dot Com Boom was like
(30:00) The mental benefits of running
(37:00) Recovering from the Dot Com crash
(41:30) Starting a VC company that actually cares about their founders
(52:00) Know which moonshot idea to invest into
(56:15) Why are VC funds going dry?
(1:03:25) Why Safenotes killed the VC industry
(1:09:53) The Last Mile - Technology training in prison
(1:13:49) Entrepreneurship in prison
(1:18:00) Building a movement across political lines
(1:20:30) Why previously incarcerated people are the hardest workers
(1:24:40) Building a company by and for incarcerated people

EPISODE LINKS:

The Last Mile: https://thelastmile.org/
The Last Mile WIkipedia Page: https://en.wikipedia.org/wiki/The_Last_Mile_(prison_rehabilitation_program)
Twitter: https://twitter.com/TLM
LinkedIn Page: https://www.linkedin.com/company/the-last-mile/
Youtube: https://www.youtube.com/channel/UCxnslwxnp3acFh13V-uvvJQ
Chris’ Twitter: https://twitter.com/chrisredlitz
Chris’ LinkedIn: https://www.linkedin.com/in/chrisredlitz/
Chris’ Instagram: https://www.instagram.com/credlitz/

PODCAST INFO:

Podcast website: https://forwardobsessed.com/
Apple Podcasts: https://podcasts.apple.com/us/podcast/forward-obsessed/id1615760781
Spotify: https://open.spotify.com/show/2TrkOZ7xL7WSlzc2mrwXuC?si=aa5e7790aca64e05
YouTube Full Episodes: https://youtube.com/playlist?list=PL-ldUUGxQZ5b9WPqVXz_qlfXgK3hHPs4z
YouTube Clips: https://youtube.com/playlist?list=PL-ldUUGxQZ5Yt0LiPml0y6pNUSrqHzWql

SUPPORT & CONNECT:

Digital Surgeons Website: https://digitalsurgeons.com
TikTok: https://www.tiktok.com/@digitalsurgeons
Instagram: https://www.instagram.com/digitalsurgeons
LinkedIn: https://www.linkedin.com/company/210497/

How To End Prison Recidivism With Chris Redlitz

Forward Obsessed