Planning Ahead: Tax Strategy for Founder-Led Exits episode artwork

EPISODE · May 7, 2026 · 1 MIN

Planning Ahead: Tax Strategy for Founder-Led Exits

from Insights by Candor Advisors · host Mike Simpson

Selling a business is not just a valuation exercise. It is also a tax planning event that can dramatically affect how much money a founder actually keeps after closing. In this episode, Kirk Michie walks through the role CPAs, investment bankers, and estate planning professionals play during founder-led exits. The discussion covers capital gains taxes, rollover equity, transaction timing, state tax exposure, and why founders should avoid making assumptions too early in the process.

Episode metadata supplied by the publisher feed · Published May 7, 2026

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Most founders think about taxes too late in the sale process. In this video, Kirk Michie explains why exit tax planning should start earlier, how deal structure changes tax exposure, and why moving states right before a sale usually does not work the way founders expect. In this short video, I break down exactly when an appraisal is actually required—like for an ESOP or legal dispute—and when you can rely on transaction advisors to give you a clear, accurate sense of your business's value instead.

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Planning Ahead: Tax Strategy for Founder-Led Exits

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This episode was published on May 7, 2026.

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