Multi-year exit planning, deal structuring, after-tax proceeds modeling, and seller-side diligence — for owners 3–5 years from sale who want to walk away with the right number.
A reactive sale leaves 15–30% on the table. An engineered exit lands the number you actually want.
Books cleaned to investor standards. Tax structure optimized. Add-backs identified. Customer concentration reduced. The work that lifts the multiple.
Explore Category →Asset vs. stock sale modeling, earnout structuring, rollover equity strategy, QSBS positioning. Every dollar of after-tax proceeds engineered.
Explore Category →Quality-of-earnings prep, working capital calculations, post-close true-ups, escrow structuring. The technical heavy lifting that closes deals.
Explore Category →Multi-state work across all 50 states.
Price scoped upfront. No hourly meter.
Answers within one business day.
Available beyond tax season. Quarterly check-ins.
Every engagement follows the same disciplined path. You always know what is next, and you always know who is doing it.
A complimentary 30 minutes. We scope what you actually need — and tell you straight if we are not the right fit.
Clear scope, deliverables, and a flat fee quoted upfront. No surprises. No hourly meter spinning in the background.
Exit readiness assessment: financials, ownership, tax structure, customer concentration, contracts. Roadmap memo within 30 days mapping the 24-36 month path.
Quarterly working sessions through the exit window — KPI tracking, structural moves, buyer-readiness items closed one at a time.
Three years before the sale, Milestone built our exit roadmap and made me feel ridiculous for the half-baked thinking I had been doing. The structural changes alone — entity restructure, QSBS positioning, customer concentration work — added $2.1M to the final price. The deal closed at 6.8x adjusted EBITDA where my industry comp was 4.5x.
— Former CEO, Bay Area B2B Services Company
Closed sale Q3 2025 · Milestone exit client 2022-2025
Ideally 3–5 years before sale. Most structural moves (entity changes, customer diversification, key-person reduction, financial cleanup) take 18+ months to bear fruit at closing. Less than 18 months out, you are negotiating, not planning.
Bankers find buyers, run the auction, and negotiate price. We design the structure, optimize the tax outcome, and ensure your numbers withstand diligence. Most clients use both — we work alongside the banker, focused on the financial engineering they cannot do.
Quarterly retainer for the prep years ($5–15K/quarter depending on complexity), then transaction-stage fees during active deal work. Total commitment over 3 years typically $80–250K — recovered many times over in deal proceeds.
Yes — we prepare sell-side QoE in-house, which buyers respect because we are CPAs, not just brokers. About 70% of our exit engagements include QoE prep.
If you are a C-corp held 5+ years with under $50M in assets at issuance, possibly yes — up to $10M (or 10x basis) of capital gains can be federally excluded. We assess QSBS eligibility in the first 60 days of every exit engagement.
It almost always does. The roadmap is a plan, not a contract. If you accelerate, we accelerate. If a buyer comes early, we activate transaction mode. If you decide to keep it 10 more years, the financial cleanup work still pays for itself in tax savings.
A complimentary 30-minute call. Tell us where the business is and where you want it to land — we will tell you straight whether 3 years of prep would actually move the needle and what it would look like.
Entity Selection
Pick the entity that matches how you actually make money - not the one the lawyer who filed it last suggested.

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