202: How to Lose Money by Buying Underpriced Properties at a Tax Sale with Jack Gibson

202: How to Lose Money by Buying Underpriced Properties at a Tax Sale with Jack Gibson

Author: Paul Moore and Josh Thomas March 9, 2020 Duration: 45:53

Jack Gibson began his entrepreneurial journey at 19 and founded his first company at the age of 21. Operating a successful nutrition consulting and distribution company, Jack had built a multimillion dollar venture before he was old enough to rent a car. Soon after that, he bought his first home as an investment. One quickly became five, and then the bug hit. He became obsessed with learning everything he could about real estate investing and soon had over 50 investment properties generating passive income. Today Jack spends his time mentoring other entrepreneurs, building his real estate investment portfolio, and helping other investors build a brighter future through the power of turnkey real estate income.


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
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…