I've never brought on an advisor for equity. I've also been an advisor many times and regret it. The disconnect between what advisors expect and what founders need creates a relationship that rarely works for either side.

Expectations Gap

Advisors think they'll meet a few times per year and earn free equity for their advice. The founders, on the other hand, have an unreasonable expectation for hands-on execution, unlimited responsiveness, and tons of intros.

The founder ultimately gets annoyed but doesn't want to fire the advisor as they'll burn the relationship so the advisor keeps on vesting.

Serial Advisors

This is so common that there are literally serial advisors who make a career out of this. They stack multiple roles over the years (like 20-50) anticipating a power law outcome.

Better Alternative

Most tech advisory roles should actually be consulting roles. This means a clear scope, short duration, and either an hourly or fixed fee (doesn't matter if paid by cash or equity).

When Advisors Work

There are only a few rare instances where bringing on an advisor makes sense otherwise it's expensive and scopeless:

  • You want to hire them full-time in the near term
  • You want them to join as an independent board member
  • You need credibility in your industry (serial advisors love this)
  • You are giving extra upside to an investor as part of a fundraising negotiation (sneaky)

CEO Advice

I also believe tech CEOs should never advise other companies. If you truly want to help, then join as an independent board member.

Understanding how to become a better CEO means knowing where your time creates the most value.

Conclusion

The lesson here is simple: if you're a founder, think twice before giving away equity for advice. If you're considering an advisory role, understand the real expectations. Most of the time, a consulting arrangement with clear scope and deliverables serves everyone better than an open-ended equity deal.

Founders who are building their next company should learn from others who turned challenging situations into major exits. The right structure for every relationship matters.

Before you bring on your next advisor, ask yourself: would a consulting agreement accomplish the same thing?