You're holding $500K–$5M+ in one ticker. The lockup is expiring or already gone. And the question runs on a loop: hold, sell, or something smarter — and what does each one cost?
The stakes are not abstract. On a large position, the gap between short-term and long-term tax treatment alone can run to six figures. A holding-period decision that moves by three weeks can be worth six figures. And QSBS — the provision that can make a qualifying gain federally tax-free — is the first thing a specialist checks and the last thing most people find out about.
You didn't get here by guessing. The Diagnostic exists so your biggest financial decision isn't a guess either.
Check out below via AdvicePay (card or ACH). You'll immediately receive your secure intake link.
Complete the intake (about 20 minutes), then we spend 90 minutes together on your position, your tax facts, and your constraints.
A 12–18 page written diagnostic with specific recommendations, specific dates, and a 30-day check-in call on the calendar.
✓You hold $500K+ of equity in one company
✓Your lockup is expiring, or already expired
✓You want the analysis, not a pitch — whoever ends up managing the money
✓You'd rather pay a fixed fee than a percentage, forever
✕Your position is under ~$250K — the fee math doesn't favor you yet, and we'll say so
✕You want someone to simply confirm that holding everything is fine
✕You need same-week execution — this is a plan, built carefully
The fastest way to keep this page honest is to occasionally mean that.
Go through the full Diagnostic. Sit through the delivery meeting. If you don't believe it was worth every dollar — say so, and the fee is refunded in full.
No forms, no friction, no hard feelings. We can offer this because the work holds up.
No. The Diagnostic is a standalone product with a fixed scope and a fixed fee. If you want ongoing execution support afterward, a monthly retainer exists — but the Diagnostic is built to be complete on its own, and most of its value lands whether or not we ever speak again.
Keep them. The Diagnostic is a specialized second opinion on the concentrated-equity portion of your picture — many clients hand the deliverable straight to their existing team. Generalist advice is not wrong; it is tuned to the median case, and a concentrated position is not the median case.
You get an email with your secure intake link and a scheduling link for the 90-minute working session. The 10-business-day clock starts when the intake is complete.
Against the problem, not the hours. The gap between short- and long-term treatment on a large position routinely runs to six figures; a single well-timed holding-period decision can be worth more than thirty diagnostics.
Then you don't pay for it. Go through the full Diagnostic, sit through the delivery meeting, and if you don't believe it was worth every dollar, say so — the fee is refunded in full.
To protect the 10-day turnaround, we take a limited number of diagnostics each month. When checkout is open, a slot is available.
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Illustrative figures on this page are hypothetical, depend on individual facts and market conditions, and are not a guarantee of any tax savings or investment outcome. Advisory services are provided on a fee-based, fiduciary basis. Refund applies to the diagnostic fee only.