Episode
26. I Built My Business to “Fail,” Now It’s Worth Hundreds of Millions
- Podcast
- AJ Osborne Podcast
- Published
- Jul 10, 2025
- Duration seconds
- 2046
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Summary
Sign Up for My Newsletter Here: https://ajosborne.com/newsletter Markets are volatile. Whispers of a recession are getting louder. Some industries—like commercial real estate—are already in recession. This has been one of the most difficult market cycles for business owners and self storage investors to navigate. Want to know how to start a business that thrives in any economic environment? I break it down in today’s episode! We’re coming off arguably the greatest bull market in history. The problem? People start businesses expecting success, which is exactly why they fail. Their systems, models, and contracts aren’t designed for the worst-case scenario. The truth is, if you want to succeed long-term, you can’t build to succeed. You must build to fail. It sounds backwards, but it’s the only way to survive the storms. Make no mistake—you will fail. But how you fail makes all the difference. You don’t need to be fearless, just aware of the risks and prepared for the valleys. In this episode, I show you how to fail the right way—small, fast, and forward! Insights from today’s episode: Why “building to succeed” is a fatal flaw in this economy (and what to do instead) The biggest mistake entrepreneurs make when starting a new business How to create “asymmetric failure” that your business can weather The number one reason businesses go under during tough market cycles Why you must treat every new investment opportunity like a business. 🎙️ Do you have a great story to share on the SSI or AJ Osborne podcasts? You can now apply here! https://form.asana.com/?k=TGU88eU0bFTFW1iHcckuTA&d=1203571084143207 📉 Take advantage of today’s market conditions and invest with us: https://cedar.cc/invest