I should know. I lost a $100 million portfolio. Yes, you read that correctly—$100 million. Gone. And yet, people still seek my business advice constantly. In fact, I’d confidently put money down that few people have screwed up more dramatically than I have in business.
The Hidden Value of Spectacular Failures
Why would anyone want advice from someone who lost $100 million? The answer is simple: experience. Real, hard-earned, painful experience.
When you’ve been through the fire of massive failure and survived, you gain insights that can’t be taught in business school. You develop:
- A realistic understanding of risk and reward
- The ability to spot warning signs others miss
- Emotional resilience when facing setbacks
- Practical knowledge of what actually works (and what doesn’t)
These qualities are invaluable in business, and they’re almost impossible to develop without experiencing significant failure firsthand.
View this post on Instagram
Reframing Your Relationship with Failure
The problem isn’t that you’ve failed—it’s that you’re letting those failures define you instead of refine you. When I reflect on losing that $100 million portfolio, I don’t see it as proof of my incompetence. I see it as the most expensive business education anyone could receive.
What if you viewed your failures the same way? Not as evidence of your limitations, but as investments in your future success?
Every setback contains the seeds of an equal or greater comeback—if you have the courage to plant them.
I’ve coached countless entrepreneurs through their darkest moments. The ones who ultimately succeed aren’t those who avoid failure—they’re the ones who extract every lesson from it and apply those insights to their next venture.
Turning Failure Into Your Competitive Advantage
Your failures give you something your competition may lack: perspective. When you’ve experienced rock bottom, you develop a certain fearlessness. You realize the worst has already happened, and you survived. This creates a freedom to take calculated risks others might avoid.
Consider these practical ways to leverage your failures:
- Document the specific lessons from each failure
- Share your experiences to establish credibility and authenticity
- Use past mistakes as a filter for evaluating new opportunities
- Build systems that prevent repeating the same errors
Your failures aren’t just learning experiences—they’re credentials that qualify you to solve problems others haven’t yet encountered.
The Path Forward
So where do you go from here? First, forgive yourself. Whatever mistakes you’ve made, they don’t define your future unless you let them.
Second, extract every possible lesson from your failures. What specifically went wrong? What assumptions proved incorrect? What would you do differently with the benefit of hindsight?
Finally, use these insights as fuel for your next venture. Your experience—especially the painful parts—is your most valuable asset. Don’t hide from it. Leverage it.
The next time you find yourself dwelling on past mistakes, remember: those failures aren’t evidence that you don’t belong in the game. They’re proof that you’ve paid the entry fee that many others haven’t.
I lost $100 million and built myself back up. Whatever you’re facing, you can overcome it too. Your comeback story is waiting to be written.
Frequently Asked Questions
Q: How do you mentally recover from a massive business failure?
Mental recovery starts with acceptance. I had to acknowledge what happened without making excuses, while also refusing to let that failure become my identity. Surrounding yourself with supportive people who see your potential rather than your past mistakes is crucial. Finally, setting small, achievable goals helps rebuild confidence and momentum.
Q: What was the most important lesson from losing your $100 million portfolio?
The most valuable lesson was learning to separate my self-worth from my net worth. When you tie your identity to financial outcomes, you’re setting yourself up for emotional disaster. I also learned the importance of diversification and not to confuse a bull market with personal genius—something many entrepreneurs discover the hard way.
Q: How do you know when to persist through failure versus when to pivot to something new?
This requires honest self-assessment. Ask yourself: Is the core business model fundamentally flawed, or is it just the execution? Are you still passionate about solving this problem? Would additional resources or a modified approach address the issues? Sometimes persistence is courage, and sometimes it’s delusion—the difference often lies in whether you’re learning and adapting from each setback.
Q: Can you share specific strategies for turning business failures into future opportunities?
First, conduct a thorough post-mortem analysis without blame. Second, identify transferable skills and relationships you developed. Third, be transparent about your failures when building new partnerships—it builds trust and sets realistic expectations. Finally, look for adjacent markets where your hard-earned insights give you an edge that competitors lack.
Q: How do you explain past business failures to potential investors or partners?
Frame failures as investments in your education and development. Be specific about what went wrong, what you learned, and how those lessons inform your current approach. Smart investors value entrepreneurs who have weathered storms—they know that naive optimism is far more dangerous than battle-tested wisdom. When I discuss my losses, I focus on how that experience makes me uniquely qualified to identify and avoid similar pitfalls.
