How to Choose a Wealth Advisor for Your Startup Exit

Why this is a harder question than it looks

Founders searching for a wealth advisor before an exit usually start by looking for someone with a good reputation or a big-name background. That's not wrong, but it's not the filter that matters most. I'd rather a founder ask three narrower questions than one broad one, because the broad question - "who's the best advisor" - doesn't actually predict whether the advisor will help you keep more of what you built.

What should I actually ask before hiring an advisor for my exit?

How are they paid, specifically? Fee-only means an advisor is paid directly by you and nothing else - no commissions, no revenue sharing, no incentive to put you into a particular product. Ask directly: "does any part of your compensation change based on what I invest in?" If the answer is anything other than no, you're not getting fee-only advice, whatever the marketing says.

Have they actually worked a QSBS analysis, not just heard of it? Section 1202 of the tax code can exclude up to $10 million, or 10 times your basis, of capital gain on qualifying stock - but eligibility depends on details most generalist advisors never encounter: how and when the shares were acquired, the company's assets at issuance, and the holding period. Ask for a specific example of how they've confirmed eligibility for a past client. A vague answer here is the biggest red flag I know of.

Will they actually coordinate with your attorney and accountant, or work around them? A liquidity event touches deal counsel, your accountant, and your wealth advisor at the same time. The good outcomes I've seen involve all three actually talking to each other before the transaction structure is finalized - not three separate professionals each optimizing their own piece in isolation.

Does it matter if the advisor specializes in founders specifically?

I think it matters more than most founders assume going in. A generalist wealth manager might handle a handful of liquidity events across an entire career. An advisor who lives in this space regularly sees the range of deal structures, the timing traps, and the mistakes that are expensive to make once. That's not a knock on generalist advisors - most of what they do for most clients doesn't require this specialization. It's just that a liquidity event is a specific, high-stakes, time-limited event, and specialization matters more when the stakes and the deadline are both real.

When should I start this search?

Twelve to twenty-four months before a transaction is likely to close, if you can. Some of the most valuable planning - QSBS structuring, charitable vehicles, income timing - needs to be in place before a term sheet is signed, not after. If you're already past that window, it's still worth a conversation; there's usually something that can still be done, just fewer options than there would have been earlier.

If you want to see how this works in practice, a 30-minute discovery call costs nothing and will tell you quickly whether there's a fit.