The story
From the deal table to the other side of it.
A recovering attorney who has been on both sides of enough deals to know which side most founders do not realize they are on.
The ascent
Roland started young. By his mid twenties he had done his first commercial real estate deal, his first public offering, and his first company purchase. Over the next four decades he built and sold businesses across medical billing, direct response, manufacturing, ecommerce, legal services, supplements, and software. He was never only an operator. He learned how capital, multiples, and deal structure really work, from inside real transactions.
The collapse
Then it fell apart. A funding source disappeared. The dot com bust hit. There was a theft, a tax dispute, serious legal exposure, and a divorce, along with time he does not pretend away. He had all the deal knowledge in the world and still nearly lost everything. Not because the deals were wrong, but because the foundation underneath them was never built to carry what he kept stacking on top.
The rebuild
What came out of that was a different way of building. Protect the downside first. Stop optimizing for income and start optimizing for enterprise value. Build businesses the way a buyer would want to buy them, not the way a founder likes to run them. He stopped asking how do I grow this and started asking what would a buyer pay for this, and why. Those are different questions, and they lead to very different companies.
Where he is now
A portfolio, a podcast, and a life off the org chart.
Today Roland has closed more than 1,000 acquisitions and exits, holds stakes in a portfolio of 17 verticals generating over $1B a year, and has been a principal of six Inc. 5000 companies. He serves on Stanford advisory boards, hosts the Business Lunch podcast, and wrote Zero Down and Business Wealth Without Risk. He now works with a small group of founders through Consulting for Equity.
