Michael J. Frank sits down with Sunny Ray to trace an unlikely path from the trading pits of the Philadelphia Stock Exchange to building a community that supports startup founders worldwide. Frank recounts starting on the floor in 1980 as a young market maker, drawn in after watching his brother out earn their father, and describes the discipline, risk management, and split second decision making that defined life as a specialist. He explains how his firm built proprietary software, including RoboClerk and the Gateway Trading System, to automate trade reconciliation and manage portfolio risk, culminating in a 2001 sale to Knight Capital Group. Frank then shares how a shared accelerator collapse led him to co found Gilder with Brian and Tiger, a low cost, equity free community offering founders mentorship, tools, and events. He closes with a candid take on AI, urging founders and workers alike to adopt these tools quickly or risk being left behind. It is a story of reinvention, resilience, and giving back to the founder community.
A Wall Street floor trader turned tech builder explains how he sold a trading firm and now builds community for startup founders.
What drew you into trading on the floor as a young guy instead of a traditional corporate path?
My brother started trading on the floor in the late 1970s and made about 80k his first year, double what my dad made after 25 years at his job. I saw that gap and thought if my brother could do it, I probably could too, so that pulled me into learning about the trading floor and options and equity trading.
What did a typical trading day look like, and what got baked into who you are today?
You'd show up at least an hour early to check your sheets and the news, then trade from open to close. It's not enough to know the math behind options like volatility pricing, you also have to execute in the crowd, hedge fast, and absorb losses when a hedge disappears and the stock moves against you.
How did building RoboClerk shape how you think about technology and efficiency?
Every morning we had to manually reconcile thousands of trades against Goldman's sheets, which took five clerks for hours. My tech guy built software that automated the matching so one person could do it in minutes, freeing three full timers to become specialist clerks instead.
What was going through your mind the day the deal with Knight Capital closed?
It was a good deal for us. We'd made a lot of money in 2000, but decimalization and multi listing in 2001 made the market unwinnable for a while, with fake quotes everywhere. I realized I couldn't fight that war for the year or two it would take to fix, so selling made sense.
What gap in the startup ecosystem led you to start Gilder?
I met my co-founders Brian and Tiger while mentoring at an accelerator called Newchip that later went bankrupt. We all lost our mentor shares. Rather than build another accelerator, we built Gilder as a community offering mentorship, tools, and events without taking equity.
How does Gilder match founders with the right mentors?
Our top plan is 350 dollars a month, cheap compared to giving up equity to an accelerator. We pair founders with mentors who've solved their exact problem, whether it's product market fit or building a funnel, and we swap mentors as the founder's needs change.
Five years from now, what does success look like for Gilder?
More people on the platform, more in-person events alongside our weekly online ones, and a growing page of founders who've gone through Gilder to successful exits or IPOs. We're not chasing a unicorn, we just want to help a lot of founders at low cost.
Any final thoughts you wanted to leave listeners with?
We're in a moment more significant than electricity or the computer, AI is going to change everything. You won't lose your job to AI, you'll lose it to someone using AI tools better than you. Go learn, there are free courses everywhere, and companies that don't adopt will get leapfrogged.
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