How we Help:
How We've Helped Business Owners Add $3M-$40M+ to Their Exit Proceeds
Strategic planning, tax architecture, and competitive deal processes make the difference between a good exit and a generational wealth event. Here's how we do it.
Real Businesses. Real Results.
Every business exit is unique, but the fundamentals are consistent: minimize taxes, maximize valuation, and structure deals intelligently. These case studies show how coordinating tax planning, M&A strategy, and deal structure created millions in additional value.
Note Box : All case studies use anonymized client data. Specific figures and strategies have been approved for educational purposes.
HVAC Company (Family-Owned)
Case Study 01
the choice to work
Primary Goals:
“You’ve built a valuable company. Let’s keep more of it.” We focused on tax-aware exit design before going to market, then used a managed auction to drive up bids.
Profile
- Entity: S-Corp
- Size: ~$18M enterprise value; ~$4M EBITDA; 75 employees
- Owners: Married couple, early 60s, Utah residents; cost basis ~$2M
- Timeline: Target sale in 12–18 months to retire
Pain Points
- Modeled $5M+ combined federal/NIIT/state taxes on sale
- No estate plan; worried about leaving a large taxable estate to kids
- Single-bid mindset from their long-time broker (risking underpricing)
- Heavy owner dependency; stale financials scared off sophisticated buyers
How We Helped
Think
“You’ve built a valuable company. Let’s keep more of it.” We focused on tax-aware exit design before going to market, then used a managed auction to drive up bids.
Problem
Without planning, they’d overpay taxes, accept a middling offer, and pass a heavily taxed estate to heirs.
Feature (Working with Compound Advisory)
Freeze–Squeeze–Burn blueprint:
- Freeze future appreciation outside the estate with a GRAT + Dynasty Trust.
- Squeeze via a light recapitalization (minority/valuation discounts), better compensation structure, and KPI cleanup to prepare for gifting/sales.
- Burn estate value over time (grantor trust tax burn + strategic gifting).
- Protected themselves with the right types of insurance
Coordinated with IndustryPros to:
- Professionalize reporting (monthly KPI pack, maintenance backlog reduction).
- Reduce owner dependency (documented SOPs, second-in-command hire).
- Run a competitive auction with strategics and financial buyers.
- We quarterbacked the tax/estate/legal team so the plan stayed cohesive.
Benefit
- Taxes: Modeled reduction of ~$3.1M lifetime taxes through trust planning and structure (GRAT/Dynasty + discounts + grantor burn).
- Value: Competitive process lifted the purchase price ~$2.2M above broker’s “quiet” offer.
- Outcome: Higher net at close, multi-decade estate-growth outside the taxable estate, and a smoother handoff.
Your Free Compound Business Valuation Assessment™
A complimentary 3-step process designed to show you what your business is really worth—and how to position it for maximum value when you exit.
You’ll see where you stand today, uncover opportunities to reduce taxes, and learn strategies to turn your life’s work into lasting wealth.
It also gives you a clear way to evaluate our services and decide whether we’re the right partner for your next chapter.
Landscaping & Mosquito Spraying (PE Roll-Up Hotspot)
Case Study 02
the choice to work
Primary Goals:
“Let’s stage the exit to capture today’s hot multiples and set you up for a tax-efficient second bite.”
Profile
- Entity: S-Corp (pre-planning)
- Size: ~$12M EV; ~60% recurring revenue (mosquito routes), 3 locations
- Owners: Couple in their 40s; growth-minded but time constrained
- Market: Private equity paying premium multiples for route-based mosquito control roll-ups right now
Pain Points
- Not positioned to capture current PE premium (messy contracts, seasonality, key-man risk)
- S-Corp meant no QSBS path; owner wanted a staged exit with a second “bite of the apple”
- Limited buyer list; fear of selling too soon/cheap
How We Helped
Think
“Let’s stage the exit to capture today’s hot multiples and set you up for a tax-efficient second bite.”
Problem
A quick sale leaves money on the table and creates unnecessary tax drag. The business also needed polish to command a top-tier multiple.
Feature (Working with Compound Advisory)
- QSBS pathing: Converted to C-Corp and issued new stock to start the 5-year QSBS clock for future equity growth.
- Estate access + protection: Funded a SLAT to remove assets from the estate while preserving indirect access through the beneficiary spouse.
- Operational polish: With IndustryPros, we tightened customer contracts (auto-renew, price-escalators), stabilized seasonal cash flow, and packaged KPIs for investor-grade diligence.
- Protected themselves with the right types of insurance
Two-step approach:
- Minority recap now (liquidity + strategic partner + management depth).
- Majority exit post-QSBS holding period to target tax-advantaged gains on the second sale.
Benefit
- Value: First transaction at a ~20% higher multiple than initial outreach—thanks to better packaging and a broader PE pool.
- Liquidity + Upside: Owners took chips off the table and retained upside with a credible QSBS track for the second bite.
- Estate: SLAT provided potential estate tax mitigation while keeping practical access.
(Note: QSBS applies to C-Corp stock meeting the 5-year/industry rules; we structured the plan so the future sale could qualify.)
Your Free Compound Business Valuation Assessment™
A complimentary 3-step process designed to show you what your business is really worth—and how to position it for maximum value when you exit.
You’ll see where you stand today, uncover opportunities to reduce taxes, and learn strategies to turn your life’s work into lasting wealth.
It also gives you a clear way to evaluate our services and decide whether we’re the right partner for your next chapter.
SaaS Company (Workflow Automation)
Case Study 03
the choice to work
Primary Goals:
“Protect the upside, diversify risk, and make the exit QSBS-smart.”
Profile
- Entity: C-Corp; founder-held common stock
- Size: ~$25M EV; 92% gross margin; NRR 116%; strong mid-market pipeline
- Founder: Late 30s; most net worth tied up in the company
- Inbound offers from strategics and growth equity
Pain Points
- Concentration risk (single asset dominates net worth)
- No estate structure; founder wants to support family and philanthropy
- Concerned about tax planning if a lucrative offer materializes soon
How We Helped
Think
“Protect the upside, diversify risk, and make the exit QSBS-smart.”
Problem
A straight sale risks a large, immediate tax bill and a missed opportunity to shift appreciation outside the estate.
Feature (Working with Compound Advisory)
- QSBS verification: Confirmed founder’s shares were originally issued C-Corp stock in a qualifying industry—preserving Section 1202 eligibility.
- Estate freeze & diversification: Executed a partial sale to an IDGT on a note (founder receives payments; appreciation shifts out of the estate).
- Charitable planning: Established a DAF for pre/post-liquidity giving and brand halo; aligned with future PR.
- Go-to-market: With IndustryPros, we refined pricing tiers, published cohort KPIs, and staged a targeted process with strategics (integrations) and sponsors.
Benefit
- Taxes: QSBS positioning enabled potential exclusion of a large portion of gains (subject to limits); IDGT moved growth outside the estate while founder retained cash flow from the note.
- Value: Positioning increased indicated enterprise value by ~$4M vs. pre-engagement interest.
- Life: Founder diversified, funded giving goals, and kept optionality for a second act.
Your Free Compound Business Valutation Assessment™
A complimentary 3-step process designed to show you what your business is really worth—and how to position it for maximum value when you exit.
You’ll see where you stand today, uncover opportunities to reduce taxes, and learn strategies to turn your life’s work into lasting wealth.
It also gives you a clear way to evaluate our services and decide whether we’re the right partner for your next chapter.
Consumer Products Brand (Specialty Food & Beverage)
Case Study 04
the choice to work
Primary Goals:
“Turn appreciation into lifetime income, reduce the immediate tax hit, and expand the buyer universe.”
Profile
- Entity: LLC taxed as partnership (pre-planning)
- Size: ~$30M EV; strong DTC + wholesale velocity; retailer expansion pending
- Owner: Early 60s; wants income, a legacy plan, and some ongoing involvement
Pain Points
- Large unrealized gains; projected $8M+ tax bill on sale
- Broker had a limited buyer list; mostly smaller strategics
- Family wanted a long-term legacy and philanthropic arm
How We Helped
Think
“Turn appreciation into lifetime income, reduce the immediate tax hit, and expand the buyer universe.”
Problem
Selling outright means a large tax bill, fewer bidders, and no structure for income or legacy.
Feature (Working with Compound Advisory)
CRT for partial sale: Moved a portion of units into a Charitable Remainder Trust to defer/avoid capital gains on that slice and create a lifetime income stream.
Freeze–Squeeze–Burn:
- Freeze appreciation outside the estate (trust planning).
- Squeeze via a light preferred/common recap and compensation normalization pre-valuation.
- Burn remaining estate value through grantor trust tax burn and annual exclusion gifting.
Market prep: With IndustryPros, elevated packaging/brand story, built a retailer sell-in deck, and ran a broader auction including larger strategics and PE brand aggregators.
Benefit
- Taxes: Modeled ~$5M reduction in immediate tax impact (CRT + estate structure).
- Value: Wider buyer pool and sharper brand positioning drove ~18% higher bids.
- Income + Legacy: Predictable CRT income and a funded giving vehicle; family retained a small stake via trust.
Your Free Compound Business Valuation Assessment™
A complimentary 3-step process designed to show you what your business is really worth—and how to position it for maximum value when you exit.
You’ll see where you stand today, uncover opportunities to reduce taxes, and learn strategies to turn your life’s work into lasting wealth.
It also gives you a clear way to evaluate our services and decide whether we’re the right partner for your next chapter.
Logistics & Distribution (Specialty B2B)
Case Study 05
the choice to work
Primary Goals:
“De-risk the diligence, lift the multiple, and move wealth outside the estate before close.”
Profile
- Entity: C-Corp (post-reorg)
- Size: ~$35M EV; 12 hubs; sticky B2B contracts with penalties/renewals
- Owners: Two siblings (50s); desire clean exit and multigenerational planning
Pain Points
- Estate tax exposure post-liquidity; no unified plan for heirs
- Buyers skeptical of contract quality and margin sustainability
- Prior banker shopping the deal too narrowly
- Heavy owner dependency; stale financials scared off sophisticated buyers
How We Helped
Think
“De-risk the diligence, lift the multiple, and move wealth outside the estate before close.”
Problem
Weak contract terms depress multiples; a full-cash exit without planning invites estate tax drag and family disputes.
Feature (Working with Compound Advisory)
- BDITs for each sibling: Enabled control/access benefits without estate inclusion; paired with IDGT sales to shift appreciation out of the estate.
- Dynasty Trust overlay: To cement multi-generational planning and creditor protection.
- Commercial uplift with IndustryPros: Re-papered key contracts (escalators/assignability), built KPI dashboards, and produced buy-side diligence packs to reduce perceived risk.
- Auction expansion: Broadened to strategics and infra-oriented sponsors comfortable with multi-site roll-ups.
Benefit
- Taxes: Projected $6–$7M in estate/gift tax savings over time through BDIT/IDGT/Dynasty structure and grantor burn.
- Value: Contract upgrades and cleaner data books lifted the indicated multiple ~1x EBITDA.
- Family harmony: Clear trustee governance, distribution rules, and liquidity plan reduced post-sale friction.
Your Free Compound Business Valuation Assessment™
A complimentary 3-step process showing you how to reduce taxes and improve your retirement success.
It also helps you evaluate our services and make an informed decision about working together.