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“I know how to run a business. I know how to make money. But when it comes to the financials? I’m completely out of my depth.”
That’s what a founder told us not long ago — someone who built a thriving company from scratch, generated millions in revenue, and is now standing on the brink of a major liquidity event.
She’s sharp, driven, and seasoned in the startup trenches. She’s navigated product pivots, hiring sprees, funding rounds, and sleepless nights. What she hadn’t prepared for? The complexities of selling.
Last year, she paid $700,000 in taxes. That number stopped her cold.
“I’ve never even had that much money sitting in my account at once,” she admitted.
And now, she’s weeks away from a sale that could change her life.
Here’s the part most founders don’t realize until it’s too late:
Without a financial strategy before the sale, the IRS becomes your largest shareholder.
You Built the Business. Don’t Let the System Write the Ending.
Exit events don’t just redistribute ownership; they also redistribute wealth. And without thoughtful planning, that wealth doesn’t go where you expect.
Most founders focus their attention on deal terms, valuation, and post-acquisition roles. Those things matter. But they aren’t the only levers that determine what you walk away with.
What’s far more important — and often overlooked — is what happens before the deal closes.
- The structure.
- The strategy.
- The timing.
- The tax implications.
Miss those, and you’ll leave more on the table than you ever intended.
Here’s What We’re Putting in Place for Her — and What You Should Be Thinking About Too:
Before taking any final actions, consider the following steps:
✅ Pre-Transaction Structuring
This is where it all starts. How your business is legally and financially structured leading up to a sale has a direct impact on what you’ll owe.
Many founders don’t realize how early you need to act — once a Letter of Intent (LOI) is signed, most of your flexibility disappears.
We assess:
- Entity structure (C-Corp vs S-Corp vs LLC)
- Ownership allocations
- Stock basis and timeline
- Rollover or earn-out terms
These details determine whether you walk away taxed at ordinary income rates or long-term capital gains — a difference that could easily equal millions of dollars.
✅ Capital Gains Strategy
Most people assume they’ll pay the standard long-term capital gains rate and consider it a done deal. That’s a mistake.
The real gains come from positioning — especially if you qualify for:
- QSBS (Qualified Small Business Stock) exclusions
- Opportunity Zones
- 1202 exemptions
- Installment sales
- Strategic holding periods
These aren’t automatic. They take proactive, legal structuring well in advance.
✅ Trust & Legacy Planning
Your checking account isn’t a finish line. It’s a transition point.
High-net-worth individuals who hold onto their wealth — and grow it across generations — don’t wait until after the exit to think about trusts. They start early.
We help founders position assets where they can:
- Reduce estate tax exposure
- Maximize privacy and protection
- Enable charitable giving
- Lay foundations for family wealth
This is how you exit the business without resetting your net worth to zero.
✅ Tax-Efficient Wealth Transfer
If you sell before building the right legal and tax infrastructure, your “win” might create a new liability.
We help founders shift wealth strategically — often before it’s even recognized as personal income — so they can:
- Support family without triggering gift taxes
- Invest in future ventures tax-efficiently
- Avoid unnecessary capital erosion
Why It Matters Now — Not Later
Once the deal is signed, most of these opportunities vanish.
Documents are locked. Structures are frozen. The window closes.
That’s why timing is everything. Our founder client still has options. She still has leverage. She can still shape the outcome. So can you — if you start early.
What We Provide
We’re not just advisors. We’re a strategy team for your exit. Here’s how we help founders take control before it’s too late:
✅ Advanced Tax Planning
We go beyond basic CPA advice. We build layered tax strategies that integrate with your business, personal, and legacy goals.
✅ M&A Attorney Referrals
Not all attorneys are created equal. We connect founders with professionals who specialize in complex transactions — and spot the hidden traps in contracts others miss.
✅ Post-Exit Wealth Management
A liquidity event is not the end of the road — it’s the beginning of a new financial life. We guide founders through diversified investing, risk protection, and long-term growth.
✅ Estate & Trust Structuring
The real measure of wealth isn’t what you earn — it’s what endures. We help build generational plans that keep your success working long after the deal closes.
Final Thought: Don’t Let the Exit Catch You Off Guard
If you’re even thinking about selling in the next 12–24 months, start planning today.
Waiting until the LOI is signed or due diligence begins is too late. At that point, your flexibility is gone. Your choices narrow. And you may end up paying far more in taxes than necessary — simply because you didn’t know your options.
You built the business. You should decide how you leave it. Let’s make sure the final chapter is just as smart as the rest of your journey.
