26. I Built My Business to “Fail,” Now It’s Worth Hundreds of Millions
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Jul 10, 2025
Discover why the most successful businesses are those built with failure in mind. Learn how entrepreneurs often fail due to an overly optimistic approach. Embrace failure as a necessary part of growth and resilience. Explore how to navigate turbulent economic waters while managing investments wisely. Understand the unique challenges millennials face in this landscape and why a growth mindset can turn setbacks into opportunities. It's all about building systems that can weather any storm!
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insights INSIGHT
Success Can Trigger Failure
Many companies fail because their own success overwhelms their capacity.
Growth can kill a company if systems and capital don't scale properly.
insights INSIGHT
Build Business to Fail
Failure is guaranteed in business and investing; it must be integrated, not avoided.
You should invest and build systems that allow for manageable failures, not expect unbroken success.
insights INSIGHT
Millennials' Unique Wealth Story
Millennials became the richest generation through investing in the longest bull market.
Economic timing and government spending fueled historic wealth for early millennials.
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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.
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