154: How to Lose Money by Signing Bad Contracts with AJ Osborne

154: How to Lose Money by Signing Bad Contracts with AJ Osborne

Author: Paul Moore and Josh Thomas April 1, 2019 Duration: 43:54

AJ Osborne has been in real estate since the early 2000s. He created Bitterroot Holdings, a self-storage company that has a $100 million asset holding portfolio. He got his start in insurance running one of the largest brokerage firms in the northwest.


Paul Moore and Josh Thomas host How to Lose Money, but don't let the title fool you. This is a wealth-building conversation built on a simple, powerful premise: the most valuable lessons often come from what went wrong, not what went right. Each episode delves into the honest, sometimes gut-wrenching stories behind business failures and costly missteps. You'll hear from entrepreneurs in the thick of a tough season and executives analyzing strategic errors, all sharing the hard-won insights they gained in the process. The focus isn't on the failure itself, but on the clarity and resilience forged in those moments. For anyone building a business, leading a team, or simply fascinated by the real, unvarnished path to success, this podcast offers a unique and compelling perspective. New conversations arrive every Monday, providing a regular dose of practical wisdom earned the hard way. Tune in for a refreshingly candid look at how the road to financial and professional growth is often paved with lessons learned from losing.
Author: Language: English Episodes: 100

How to Lose Money
Podcast Episodes
204: How to Lose Money by Making Instant Coffee with Josh Zloof [not-audio_url] [/not-audio_url]

Duration: 30:05
Josh Zloof is the co-founder and CEO of Sudden Coffee, the creators of the first specialty instant coffee. Sudden Coffee works with 30 coffee roasters worldwide, companies like Equator Coffee, Intelligentsia Coffee and R…
203: How to Lose Money by Staying in the Closet with David Hancock [not-audio_url] [/not-audio_url]

Duration: 35:22
David Hancock is the founder of Morgan James Publishing and has co-authored 12 books, including Performance Driven Thinking, Guerilla Marketing for Mortgage Brokers, and The Entrepreneurial Author. Nasdaq sights David as…
200: How to Lose Money by Being in a Coma with Nick Prefontaine [not-audio_url] [/not-audio_url]

Duration: 43:10
In 2003, Nick Prefontaine was in a snowboarding accident that left him in a coma for over 3 weeks. The doctors told his parents he probably wouldn't walk, talk, or eat on his own again, but he actually ran out of the hos…