The Exit Playbook: How to Sell a Business the Right Way

Every business owner expects the exit to be the finish line. But for most, it's the moment they're least prepared for. In the third and final episode of the ATL Alts Business Owner Masterclass, host Andres Sandate and Brad Gunter (Founder & CEO, High Point Advisory Group) go deep into the sell-side playbook -- covering everything RIAs need to know to help their business owner clients navigate the most consequential financial event of their lives.

Brad and Andres break down the critical mindset shift from 'I'm ready to sell' to truly 'exit ready,' the timeline reality that surprises most owners (three years is the minimum; five if you want full tax optimization), and why showing up to a deal without a sell-side QOE is like going to court without a lawyer. They map the full buyer universe -- from SBA-backed search funds to independent sponsors, private equity, strategics, and family offices -- and explain what each type of buyer actually wants, how they operate, and which seller profile fits each best.

The conversation then turns to deal mechanics that can make or break the net economics: equity rollovers and the second bite at the apple, seller notes, earnouts, escrows, holdbacks, working capital adjustments, and reps and warranties. They also cover the tax planning conversation that most advisors wait too long to have -- QSBS, short vs. long-term capital gains, qualified opportunity zones, deferred sales trusts, and charitable structures. And they close with what happens after the wire hits: how to help a liquid entrepreneur think about generational wealth, alternatives, and the next chapter.

This episode is for every RIA with a business owner client considering a sale in the next three to five years.

Episode Overview

The series culmination. Brad and Andres cover the full exit arc -- mindset, timing, sell-side diligence, buyer selection, deal mechanics, tax strategy, and post-liquidity wealth deployment. This episode is the most immediately actionable for RIAs: every section maps to a specific conversation they should be having with business owner clients right now.

Timestamps

0:00 Series recap -- buying (Ep 1), operating (Ep 2) -- and why the exit is the 'peak of the trilogy'

3:37 The critical mindset shift: 'I'm ready to sell' vs. 'exit ready' -- and why most owners confuse the two

5:08 The Rolls-Royce vs. deal-hunter spectrum: how to identify which buyer profile fits your client's business

6:45 The clean test for exit readiness: could a QOE team, lawyers, and a lender go through the business without substantial issues?

8:18 The wealth event and why it's underestimated: 75-80% of net worth in a single transaction, often for the first and only time

10:00 Why owners resist outside advisors: 'I've been successful at everything else -- why would this be different?'

11:37 The surgeon analogy: why you want a specialist, not a generalist, for every lane of the exit

13:30 The continuum of wealth: from OpCo cash flow to family office -- and where the RIA fits throughout

16:28 Sell-side timeline reality: start the day you launch; buyers look at 3 years of financials; QSBS takes 5 years

18:31 What to do if you have 18 months: sell-side assessment, retroactive cleanup, quick-hit fixes

19:41 The RIA's call to action: ask 'what's the five-year strategy?' not 'when are you selling?' -- and listen for alarm bells

21:40 The sell-side QOE: why the seller should pay for one, how it shifts negotiating leverage, and when it's required by M&A advisors

24:28 War story: $50M deal collapses to $3M cash at close -- seller note the rest, life's work nearly gone

25:33 The buyer universe from bottom to top: SBA/search funds, independent sponsors, private equity, strategics, family offices

29:00 What each buyer type actually wants: SBA timeline (90+ days), IS deal-first capital-second, PE's return clock, strategics overpaying for a gap-fill, family offices holding forever

33:00 It's not just price -- employees, community reputation, business continuity, and legacy all matter to sellers

33:33 The second bite at the apple: equity rollover mechanics -- 80/20 split, capital stack math, betting on PE to grow EBITDA 50%+

36:52 Deal terms that determine net economics: seller notes, earnouts, escrows, holdbacks, working capital pegs, reps and warranties

40:00 Time value of money in deal terms: why buyers beat the headline number by spreading payments -- and how the RIA can model this

41:05 Tax planning at exit: short vs. long-term capital gains, QSBS (5 years, first $10M tax-free), QOZs, deferred sales trusts, charitable structures

44:35 The three forces converging in alternatives: clients asking for alts, asset managers targeting wealth, and underserved investors -- and how EnduranceX addresses all three

48:00 The advisor coordination problem: 5-6 parties at the exit table, and who plays quarterback

49:14 The full exit advisory team: M&A advisor, wealth advisor, tax advisor, accountant, fractional CFO, legal

51:11 Post-liquidity: liquid entrepreneurs who want to redeploy, the non-compete reality, and why most shouldn't go all-in like Elon

54:00 The generational wealth conversation: 80-year time horizons, compounding capital, and why multigenerational clients belong in alternatives

56:30 Brad's one mindset shift for every RIA: stop assuming you'll get the money one day -- start maximizing it by bringing in the right experts now

57:15 Series close and what's next for the EnduranceX / High Point partnership

Key Takeaways

• 'I'm ready to sell' is a feeling. 'Exit ready' is a score. Can a QOE team, lawyers, and a lender go through your business without substantial issues and re-adjustments? That's the real test.
• Three years is the minimum prep timeline. Five years is ideal for full tax optimization (QSBS, QOZ, charitable structures). If a client says 'I want to sell next year,' alarm bells should be ringing.
• A sell-side QOE is not optional for serious transactions. It shifts negotiating leverage from the buyer's table to yours, surfaces skeletons before they surface in diligence, and is increasingly required by sophisticated M&A advisors and investment banks.
• The buyer universe is wider than most owners realize: SBA/search funds (sub-$5M-$10M), independent sponsors (deal-first, capital-second), private equity (return clock, operational pressure), strategics (willing to overpay for a gap-fill), and family offices (no horizon, hold forever). Each requires a different seller profile and prep strategy.
• Deal mechanics determine net economics more than headline price. Seller notes, earnouts, escrows, holdbacks, working capital pegs, reps and warranties -- these are the terms sophisticated buyers use to spread cost over time and transfer risk back to the seller.
• The second bite at the apple is one of the most underutilized exit structures in the lower middle market. Roll 20%, take 80% cash, and bet that a PE firm grows your EBITDA 50%+ in five years. That 20% can be worth more than the 80% you sold.
• QSBS is the single most powerful tax tool for business sellers -- but only if the clock started at least five years before the exit. The first $10M in gains is tax-free on a qualifying C-corp. RIAs who don't surface this early are leaving potentially millions on the table.
• The exit advisory team needs a quarterback. Five or six parties (M&A advisor, wealth advisor, tax advisor, accountant, fractional CFO, legal) each operate in their own lane. The RIA is the best-positioned to quarterback the whole process -- but only if they're in the room years before the sale.
• Post-liquidity, most business owners are liquid entrepreneurs who want to redeploy. The job of the RIA is to help them take chips off the table, diversify intelligently (including into alternatives), and protect generational wealth from being redeployed too aggressively too fast.
• Brad's one mindset shift for every RIA: stop assuming you'll get the assets someday and start maximizing today by bringing in the right specialists now. That operating business is your client's largest asset. Treat it like one.

The Full Exit Advisory Team -- Who Plays What Role

M&A Advisor / Investment Bank

Runs the sale process -- buyer outreach, marketing, negotiation, LOI management, closing coordination

Wealth Advisor (RIA)

Quarterback of the overall process; post-liquidity asset deployment, tax-aware structuring, portfolio construction, long-term wealth planning

Tax Advisor

Pre-exit planning (QSBS, QOZ, deferred sales trust, charitable structures, F-reorg); entity election optimization; post-close tax filing

Accountant / CPA

Historical financial statements, tax return prep, coordination with QOE team; data room population

Fractional CFO (e.g., High Point)

Runs internal financial process; coordinates data room; interfaces with buy-side QOE team; financial modeling of deal terms

QOE Provider (Sell-Side)

Normalizes and verifies EBITDA; surfaces issues before they hit diligence; provides negotiating leverage; may be required by M&A advisor

Legal Counsel

LOI review, purchase agreement, reps and warranties, indemnification, escrow structure, non-compete, employment agreements

RIA EXIT READINESS CHECKLIST -- QUESTIONS TO ASK BUSINESS OWNER CLIENTS

Use these questions to assess where a business owner-client stands on the exit-readiness spectrum -- and to identify where High Point Advisory Group can step in.

Timing and Mindset

• What does your five-year plan look like for the business?
• Have you had a professional assessment of what the business is worth today?
• If you had to sell in the next 12 months, what would break down first?
• Is the business sellable without you in it today?

Financial and Operational Readiness

• Do you have three years of clean, accrual-based financials ready to share with a buyer?
• Is there a data room prepared, or could one be assembled quickly?
• Have you had a sell-side QOE done -- or any third-party assessment of your EBITDA?
• Are there any material issues a buyer would find in diligence that you're aware of?

Tax Planning

• Has your tax advisor evaluated your eligibility for QSBS -- and when did you start the clock?
• Have you explored qualified opportunity zones, deferred sales trusts, or charitable structures?
• Is the business currently structured in a way that maximizes post-tax proceeds at exit?
• Are you currently running personal expenses through the business?

Deal Mechanics Awareness

• Do you understand the difference between a seller note, an earnout, and an equity rollover?
• Have you modeled what different deal structures mean for your actual cash at close?
• Do you have a wealth advisor who's already part of your exit planning team?
• Who is your quarterback for the exit process -- or have you identified who that will be?

Post-Liquidity

• When this business sells, what do you want the proceeds to do for you and your family?
• Do you have a non-compete clause that would restrict your next move -- and for how long?
• Have we talked about what multigenerational wealth building looks like on the other side of this?
• Are you familiar with alternatives as an asset class, and how they fit into a post-liquidity portfolio?

GUEST BIO -- BRAD GUNTER, Founder and CEO, High Point Advisory Group

brad.gunter@highpointadvisorygroup.com

(770) 280-7348

Atlanta, GA

highpointadvisorygroup.com

Brad Gunter is the Founder and CEO of High Point Advisory Group, a lower middle market advisory firm delivering transaction advisory (buy-side and sell-side Quality of Earnings), fractional CFO and accounting services, strategic exit preparation, and capital advisory. Brad built High Point to fill the institutional advisory gap for businesses in the $5M-$100M range -- a space where those services are historically unavailable or unaffordable. Prior to founding the firm in early 2024, Brad held roles at Deloitte's strategy and M&A group and served as Head of Strategy at a private equity platform. He earned his MBA from Georgia Tech. High Point works alongside RIAs and family offices as a non-competing partner, covering the operating and transactional dimensions of a client's financial life that traditional wealth management doesn't touch.

Companies mentioned in this episode:

• High Point Advisory Group
• GPWA
• Gramercy Park Wealth Advisors
• EnduranceX

Mentioned in this episode:

Brad Gunter Masterclass Post Script

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