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
143: How to Lose Money by Chasing a Deal Too Long with Oren Klaff [not-audio_url] [/not-audio_url]

Duration: 47:49
Oren Klaff is one of the world's leading experts on sales, raising capital and negotiation, having pitched and closed over $500 million of investor capital in recent years. His first book, Pitch Anything, is required rea…
142: How to Lose Money by Mismanaging Your 401k with Mike Kirby [not-audio_url] [/not-audio_url]

Duration: 32:29
Mike was laid off after almost 34 years from the high-tech industry at the age of 55. Instead of grieving, he took his 401k and turned it into a "self-directed IRA LLC" and then turned that LLC into a multi-million dolla…

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