The Playbook in Action

See the Playbook in Action

Every situation below is based on the kinds of challenges our clients actually face. Different starting points, different goals — same process. Here’s how the Playbook works.

Case Study

The Concentrated Stock Problem

$1.8M vested in one stock - 74% of net worth - No exit Plan
The capital gains bill felt paralyzing ,so they did nothing. We modeled a collar strategy with tax-loss harvesting via a long/short SMA. Protected the downside, started diversifying systematically, no surprise tax event.
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Case Study

The Business Owner Planning an Exit

$3.5M valuation · S-Corp · No succession plan · Selling in 5 years
A lump sum sale would have meant a devastating tax bill. We structured an installment sale to spread the gains, layered in pre-sale loss harvesting, and used donor-advised fund contributions to offset a chunk of the hit. He kept significantly more than he would have on his own.
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Case Study

The Landlord Who is Done Being a Landlord

$3.2M in rental properties · Near-zero cost basis · Tired of managing tenants
Thought a 1031 exchange was his only option. We explored alternatives that didn’t just kick the can down the road. Used tax-loss harvesting to build an offset, donor-advised fund contributions to address depreciation recapture, and an installment sale to spread the gains. Real exit. Real diversification. No more 3am plumbing calls.
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Case Study

The Business Launcher

Executive planning a business launch while trying to build accessible capital
Good savings habits, but all of it locked up. We restructured around a business launch window, building flexibility without sacrificing the long-term plan.
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