186: How to Lose Money by Starting a Marketing Agency with John Crestani

186: How to Lose Money by Starting a Marketing Agency with John Crestani

Author: Paul Moore and Josh Thomas November 18, 2019 Duration: 41:30

Born in 1987, John Crestani has accomplished a lot in his 32 years. In 2009, Crestani, 21, traveled to Thailand to figure out his direction in life and find himself. During this time, he read a number of spiritual works, such as The Alchemist, that would later influence his life, but his saving grace turned out to be a business book. John was sitting on a beach in Thailand, poor and lost in life, when he opened a book that helped transform him into becoming a motivated and successful internet entrepreneur. This book was The 4-Hour Workweek by Timothy Ferriss, the now classic manual for breaking free from the 9 to 5 workweek desk job by building an online business. After a number of years of trial and error building his internet business, Crestani finally managed to create a multimillion dollar business. He met his wife and traveled the world. He went from deep in debt to having a successful cash flow positive business that supports his life, his wife and their 3-year-old child. As of late, he's gone on to build an education empire, and now he's taken it upon himself to teach a handful of aspiring entrepreneurs how they too can transition to the new entrepreneurial economy and be their own boss.


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
155: How to Lose Money by Chasing the Wrong Dream with Ellie Perlman [not-audio_url] [/not-audio_url]

Duration: 38:25
Ellie Perlman is a real estate investor who owns 2,000 units across the U.S., worth over $250 million. Ellie is the founder and CEO of Blue Lake Capital, a real estate investing firm specializing in multifamily investmen…
154: How to Lose Money by Signing Bad Contracts with AJ Osborne [not-audio_url] [/not-audio_url]

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 b…
148: How to Lose Money by Not Having Boundaries with Michael Levitt [not-audio_url] [/not-audio_url]

Duration: 38:40
Michael Levitt, with Breakfast Leadership and published author of 369 Days: How to Survive a Year of Worst-Case Scenarios, brings people back to life. He's focused on helping individuals and leaders within corporations l…