The single best decision I made early in my entrepreneurial career wasn’t about product or market. It was asking smarter, more experienced people to sit beside me.
That’s what an advisory board does. And unlike a formal board of directors — with its governance requirements and legal obligations — an advisory board is a smaller, more agile circle of trusted guides who’ve simply been where you haven’t yet.
As a young CEO, you carry a weight you rarely admit out loud. You’re expected to know things you couldn’t possibly know yet. An advisory board quietly changes that equation.
Here’s what I’ve seen work across five decades of investing and entrepreneurship:
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Keep it small and intentional. Three to six advisors with genuinely complementary expertise — someone who’s scaled past your current stage, someone with deep domain knowledge, someone with investor relationships. Diversity of background matters. They’ll challenge blind spots your team simply can’t see.
Meet regularly, but don’t burden them. Monthly or quarterly video calls work beautifully. Today’s tools have made geography irrelevant. A great advisor in Boston can be just as present as one across town.
Give them skin in the game. Modest equity — something in the range that feels meaningful but protects your cap table — signals you’re serious and keeps them engaged. Advisors who are invested make introductions. Those who aren’t tend to give advice and gradually disappear.
Be honest with them. The moment you start managing your advisors instead of leveling with them, you’ve wasted the relationship.
The best CEOs I know are never truly alone in the room — even when it looks like they are. Build your circle before you need it. You’ll need it sooner than you think.
