160: How to Lose Money by Losing All Your Customers with Ian Ippolito

160: How to Lose Money by Losing All Your Customers with Ian Ippolito

Author: Paul Moore and Josh Thomas May 13, 2019 Duration: 36:16

Ian Ippolito is a serial entrepreneur and the creator of the investment analysis website called therealestatecrowdfundingreview.com. The site has over 12,000 visitors per month and has been featured in USA Today, Bloomberg News, Realtor.com, Curbed and more. Ippolito is also the founder of a private investor club for alternative investing, with over 1,300 members and over 1.35 billion in investable assets. In 2001, Ippolito created one of the first remote work websites from an extra bedroom in his house, rentacoder.com, which was later renamed vworker.com. Ippolito grew it to 450,000 users, 15 employees, and 11.1 million in revenue before selling it to freelancer.com for an undisclosed price in the millions. Before that, he created one of the first open-source websites for programmers, planitsourcecode.com. At its peak, the site had 1.5 million visitors per month. Ippolito has been awarded the Inc. 5000 Fastest-Growing Private Company Award four years in a row, and named to the 100 Most Innovative and Brilliant Companies by Entrepreneur Magazine. Ippolito has been interviewed by the Wall Street Journal, Business Week, Forbes, Time, Fast Company, Tech Crunch, CBS News, Fox News and many more.


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…