What Do Your Startup Advisors Say About You?

The most honest thing you can say about a formal advisor relationship is this:

It's a workaround.

When a founder tells me they need an advisor to open doors in an industry they don't know, or to fill in a knowledge gap they don't have, I hear:

“We don’t know the right people.”

A need for an advisor can be a tell that the network they built before starting their company didn't extend to that industry, or that the relationships they cultivated weren't deep enough to call in that favor for free. Unfair? Maybe. Networks take decades to build and most first-time founders don't have enough of them—but can we just be honest that they’re not a flex?

The best founders I've seen operate don't have "advisors" in the formal sense. They have ten to twenty years of real relationships — people who'll take a call on a Sunday because the relationship is genuine, not because they're vesting monthly into 0.5% of your cap table.

That gap — between the relationship you have and the one you need — is what advisors are supposed to bridge. They can, but you should be clear-eyed about what you're buying and how obvious it is to a funder.

I wrote about this dynamic differently in 2016, in a context that had nothing to do with advisor agreements. A panelist at a startup event told a Black female founder that if she wanted to raise funding, she should hire a white guy to be the face of her business. I had seen this play out firsthand — female founders who brought in a finance type to lend credibility to the meeting. In every single case, the guy detracted from it. He dominated the conversation, cut the founder off, and tried to form some imaginary financing-bro bond with me that didn't exist.

The person I wanted to hear from was the founder and the "advisor" only made her look less confident in her own vision.

The same dynamic plays out in advisory boards, just more slowly and with less drama. You bring someone in because you believe their name, their network, or their domain knowledge will compensate for something you don't have. Sometimes it works. More often, the gap you were trying to fill was really a relationship gap — and a formal agreement with a relative stranger doesn't close a relationship gap.

It just puts it on your cap table.

There's a second version of this mistake that's more subtle. Sometimes a founder finds someone who should actually be working with them — not as an advisor but as a full-time hire or a genuine fractional contributor. They can't afford the salary. So they limit the time, limit the cash, call it an advisory relationship, and hand over equity to make it feel like compensation. These are not the same thing. If the honest answer is that this company would be materially better with this person inside it every week, working on real problems, then an advisor structure isn't a clever workaround — it's a way of avoiding the question. Either you find a way to bring them in properly, or you acknowledge that you're not actually at the stage where you can afford what they'd actually cost, which is useful information. Advisors are not fractional hires without the money. They're a different kind of relationship, and conflating the two is how you end up with someone vesting into your cap table while neither of you is quite sure what they're supposed to be doing.

The advisors who actually help are almost always people founders already have a real relationship with. They know the business. They've seen the founder operate. When the call comes at a bad moment, they pick up anyway.

If that description doesn't fit the person you're thinking of formalizing — if what you really have is two good meetings and a lot of mutual optimism — slow down. Have a few more conversations. Ask them for help before you offer them equity. See if they actually show up.

Real relationships don't require a vesting schedule to activate.

Workarounds are fine. Sometimes they're exactly what you need. Just don't confuse the workaround for the thing itself.

Have more questions about advisors and how to bring them on?

Join our upcoming webinar with our friends from Qapita who specialize in cap table management.