185: How to Lose Money by Spreading Yourself Too Thin with Shawn Yesner

185: How to Lose Money by Spreading Yourself Too Thin with Shawn Yesner

Author: Paul Moore and Josh Thomas November 11, 2019 Duration: 37:40

Shawn Yesner is a Florida native, born in Tampa and raised in Miami. After graduating from Florida State University with a B.S. degree in accounting, Shawn enrolled in the Cumberland School of Law at Samford University, graduating with a Juris Doctor degree in 1998. Since our last interview, Shawn's podcast, the "Crushing Debt Podcast", has continued to grow and now is in its fourth year. Shawn estimates that he's helped his clients eliminate a collective amount of over $10 million. In September 2018, Shawn published his first book titled, Crushing Debt: 9 Strategies to Eliminate Financial Bullies. The book is available right now on Amazon.


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
198: How to Lose Money by Paying a 44% Tax Rate with Andrew Henderson [not-audio_url] [/not-audio_url]

Duration: 29:38
Andrew Henderson founded Nomad Capitalist to help people increase their personal freedom and to help them improve their financial situations and intelligently diversify their lives. Helping people save $280,000 a year in…
197: How to Lose Money by Being Overconfident with Antoine Martel [not-audio_url] [/not-audio_url]

Duration: 35:09
Antoine Martel is a 24-year-old real estate entrepreneur. He started investing in real estate while at university and has since bought and sold over 150 homes and multiple apartment buildings. He currently lives in LA wh…
195: How to Lose Money by Taking Venture Capital with Bob Fraser [not-audio_url] [/not-audio_url]

Duration: 39:03
Bob Fraser is co-founder and CFO of Aspen Funds, a fund management company focused on mortgage investments. He has 20+ years' experience as a finance and technology executive, and he is a magna cum laude UC Berkley compu…
194: How to Lose Money by Not Signing Contracts with Todd Dexheimer [not-audio_url] [/not-audio_url]

Duration: 41:03
Todd Dexheimer is CEO of Venture D Properties LLC. He started investing in real estate in 2008. Since then he has purchased and renovated roughly 800 units. Todd has completed over 150 flips, including a 20-unit mobile h…
189: How to Lose Money by Drowning in Dumb Debt with Brett Swarts [not-audio_url] [/not-audio_url]

Duration: 32:09
Brett Swarts is the CEO of Capital Gains Tax Solutions, and each year he equips hundreds of business professionals with a deferred sales trust tool to help their high net worth clients solve capital gains tax deferral li…