A CFO's Guide to Understanding Founders.

What I've Learned from Over 25 Years of Working with Founders

In more than two decades as a fractional CFO for privately held companies, I've worked with Founders across industries, company sizes, and growth stages. The experiences have been varied—and not every story is a perfect one. Founders bring energy and innovation, but also risk, blind spots, and emotional complexity. Here’s what experience has taught me:

Me and My Founders, on the best of days.

Vision Without Financial Grounding is Dangerous

Founders are visionaries. They can see opportunities others miss, but too often, they underestimate the importance of financial discipline. I once worked with a Founder of a family owned business who had no working cash flow model. Without basic forecasting, the company nearly ran out of money when its largest client departed. Big ideas are necessary; financial grounding makes them real.

Trust is Earned, Not Given

Founders don't always like hearing bad news, but the best ones respect it. The best ones don't argue with it, want to spin it, or try to make it go away. The best ones accept it and work with you to figure out how to make it right. In one engagement, I had to tell a founder their new expansion plan would overextend the company financially, despite early investor enthusiasm. It was a difficult conversation that temporarily strained our relationship. Six months later, when a downturn hit, that decision probably saved the company. Trust isn’t about always agreeing but consistently telling the truth.

Straightforward Advice Over Flattery

Founders are surrounded by people who depend on or want something from them. I've learned that being another "yes person" helps no one. I once asked if I was a wallflower and nearly fell off my chair. One client’s service model was bleeding margin despite steady sales growth. A blunt conversation about their staffing structure led to a 15% margin improvement within a year. Candor—even when uncomfortable—creates results.

Flexibility > Rigid

You can build a beautiful financial plan, but if a founder can't pivot when needed, the plan becomes irrelevant. I once supported a Founder whose market changed nearly overnight. Because we had modeled flexible scenarios, they were able to adjust pricing, staffing, and marketing within weeks. Rigid operators get run over; agile ones survive.

Emotional Intelligence Isn't Optional

Working with founders isn't just about the numbers—it's about navigating their ambitions, fears, and sometimes unrealistic expectations. It's about knowing when to push, when to listen, and when to step back. One founder told me, "You’re the only person who talks to me like I don't own the place."

Founders are People, Too

Founders can be brilliant, frustrating, inspiring, and maddening—sometimes all in the same meeting. Success in working with them comes down to a mix of strategic rigor, candor, flexibility, and emotional intelligence. You don't need to pander to founders to support them effectively—you need to meet them with expertise, backbone, and a clear-eyed view of the road ahead.