Every company reaches moments where the textbook answer doesn’t apply — where strategy, technology, and execution collide, and someone has to make a call with incomplete information and real consequences. I’ve spent my career in those moments: as a Navy engineer responsible for a nuclear reactor’s control systems, as a founder deciding whether to sell a company for $105M or hold out for a billion-dollar outcome, as an executive walking into companies that needed someone to build the first version of everything.
What I bring isn’t a framework. It’s judgment, earned by having actually been on the hook for the outcome — as founder, as operator, as board member, and as advisor.
A Few Things I Believe
The worst-case scenario is usually survivable.
When I was deciding whether to leave AT&T to start what became Ribbit, I spent months agonizing over the downside. My wife finally asked me to actually describe the worst case — no savings, no house, back to renting. Then she pointed out: that’s just where we were three years earlier. Reframing risk in concrete terms, rather than abstract fear, is often the difference between a decision and a stall.
There are two easy times to start a company — and most people aren’t in either one.
A mentor once told me the ideal times to found a company are when you’re young with nothing to lose, or late in your career with resources and grown children. Everything in between is hard by design. I started Ribbit in the “everything in between” phase, with two young kids and no income. It’s still possible — it’s just honest to say it’s harder.
An offer is always worth entertaining, even when your board hates the idea.
When BT first approached Ribbit, our board was frustrated we’d even taken the meeting — we’d just closed a strong round and were, by their read, headed toward a much bigger outcome. But you owe it to your investors, your team, and yourself to actually run the math on a “buy-it-now” price rather than dismiss an offer on principle.
Hire the insurance policy, even if you never use it.
During the BT negotiation, our board insisted we retain an investment bank — not to run a formal process, but to be ready to move immediately if the deal fell apart. We never needed them. Having them in the wings kept everyone at the table honest and focused on closing.
Relationships compound in ways you can’t plan for.
Ribbit’s first funding traced back to a family breakfast I almost skipped. The BT acquisition traced back to a chance conversation with a stranger at an airport bar, years before either side knew it mattered. I don’t believe in forcing networking — I believe in showing up, being genuinely useful to people, and letting time do the rest.
Build what you’d want to use, then learn what you don’t know.
At EasyNDA, I taught myself HTML, CSS, and JavaScript to build the product myself while recruiting a technical co-founder. I’ve never believed you need to already know how to do something to start doing it.
Advice is worth more than a check, and it’s worth even less the moment it becomes leverage.
When I meet a founder, I start with an exploratory, get-to-know-you conversation: what they’re actually stuck on, not what I assume they need. From there I offer advice based on what I’ve actually lived through, not theory. In some cases that grows into a formal advisory role or a retainer, but only if the founder wants it to. And if the relationship crosses into something more direct — an investment, a board seat, a hire — I step back from any position that could be mistaken as leverage or pressure. A founder should never feel like taking my advice is the price of staying on good terms with me.