As a CEO and entrepreneur for nearly 25 years, I’ve had my share of successes, including bootstrapping three companies to exits that sold for six, seven, and eight figures.

By my early 30s, I had achieved total financial freedom. But that success came at a cost—a cost I didn’t fully understand until it was too late.

I started my career a solo founder—a choice that, in hindsight, was a reflection of a deeper character flaw: not asking for help. Y Combinator won’t even accept solo founders because the odds of long-term success are so low. Despite this, I pushed my first company to $25 million in revenue. It was a significant milestone, one that led to an 8-figure deal for me personally when I sold the company.

But here’s the kicker—within two years after the sale, the company tripled its revenue to $75 million in ARR. I had burned out. I had sold way too early. And that burnout cost me over $100 million in personal wealth.

After that experience, I knew I needed to recharge and renew myself for the next phase of my entrepreneurial journey. I immersed myself in adjacent fields—psychology, neuroscience, conflict resolution, emotional intelligence, sports, and even theater. I sought out world-class experts, learning directly from them to uncover the insights that could truly unlock potential—not just in business, but in life.

But learning wasn’t enough. I needed to put these principles to the test in the real world of entrepreneurship. So, I kept starting and buying companies, building teams, and applying what I’d learned. This real-world laboratory allowed me to see firsthand which principles worked and which failed. The last 5 years have been a continuous cycle of experimentation, failure, and success, all aimed at refining what truly unlocks potential.

While I started as a solo founder, I’ve discovered it’s WAY more fun to partner with and help others.

I've sifted through countless frameworks and experts to help others find a more direct path to realizing a vision.  I've learned to ask the right questions to get to the answers I don't have.

As I scale my next mountain, I'm committed to sharing what I've learned, both from my own personal entrepreneurial experience and the incredible experts I've been fortunate to learn from.  My goal is to illuminate the path to applying this wisdom within your organization.

As I continue to learn, experiment, fail, and succeed, I’ll share the journey here. My hope is that some of my experience can help you navigate the challenges of turning a vision into something real.

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Matt acquires or invests in cash-flowing digital businesses with $1-$5M in EBITDA.

Occasionally, he takes on advisory engagements for interesting projects. If this is of interest, feel free to share more.

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