Business and exit planning
Your company is probably your income, your largest asset, and a big part of your identity in one place. Exit planning gets all three ready for a sale, a succession, or simply more freedom, years before you need it.
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For years the smartest move was feeding the business. Every spare dollar went back in, the business rewarded it, and the rules felt simple: the company first. The habit that built the company, though, can leave its owner with a net worth that is one asset deep and a retirement that depends entirely on a future sale going well.
Exit planning is the discipline of getting you ready alongside the business. That means wealth building that doesn't wait for a buyer, books and operations a buyer will believe, and an answer to the question owners underestimate: what your income, your days, and your identity look like after the handoff.
I hold the Certified Exit Planning Advisor (CEPA) designation, and I went independent in 2025 to build this practice, so I've lived the owner's version of these questions: uneven income, everything reinvested, the company as the plan. That's the seat I take at your table.
They should, even while the business funds them. We build a personal balance sheet that could survive a rough year at the company: retirement accounts in your name, an emergency reserve outside the business, insurance that doesn't end if the company does. Coordinated is the goal. Tangled is the risk.
You have better tools than employees do, and nobody will set them up for you. Depending on your income and headcount, that might be a SEP IRA, a solo 401(k), or a full plan with profit sharing. The right structure shelters more of your income and builds wealth the business can't touch. We design it around the company's cash flow.
Years before a sale, ideally three to five, because the things that raise a company's value take time: books a buyer trusts, a team that runs without you, revenue that isn't all in one relationship. Owners who start early sell from strength. Owners who start at the offer take what's on the table.
Most of my exit work happens in that early window, well before a broker is hired. The CEPA framework calls it building value and readiness together: the company becomes worth more, and you become ready to leave it.
Your CPA on tax structure, an attorney on the agreement, often a broker or banker to run the sale itself. My job is making sure they're all working from one plan: your number, your timeline, your life afterward. The coordination is half the value, because these advisors rarely compare notes unless someone makes them.
A portfolio with a job description. The business paid you a salary, distributions, and plenty of perks, and the sale proceeds have to take over that payroll. We map your actual spending, build an income plan from the proceeds, and invest the rest for the decades ahead. The paycheck changes source. The life it funds doesn't have to.
This is also where the emotional plan lives. The business gave you somewhere to be and a scoreboard that updated daily. Deciding what replaces those deserves the same attention as the portfolio, and we give it that attention on purpose.
Four professionals, one deal. The value shows up when they're pointed at the same plan instead of meeting each other at closing.
| Professional | What they handle | What they don't |
|---|---|---|
| Financial advisor (CEPA) | Your personal side: what the sale must fund, retirement savings before the exit, investing and income after it, and keeping the whole team on one plan. | Marketing the company or negotiating the deal itself. |
| Business broker or investment banker | The transaction: valuing the company for market, finding buyers, running the process, negotiating price and terms. | What the proceeds mean for your life, or any planning after closing. |
| CPA | Tax structure of the deal, entity questions, and the returns in the year of sale. | Long-term investment strategy or retirement income design. |
| Attorney | Purchase agreements, contracts, and the estate documents a sale should trigger updating. | The financial plan those documents are meant to serve. |
Jesse Plunkett, CEPA®, CRPC®
Financial advisor in Sanford, FL, serving clients across the country virtually. Meet your advisor, or check my record on 
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A quick, useful starting point
1. Named beneficiaries override your will Beneficiary listings on investment accounts override your will entirely. Named an ex-spouse or a late parent? They still inherit, no matter what your will says…
A short call, owner to owner. Tell me where the business stands and what you'd want life to look like on the other side, and we'll go from there.
It's the best time, because the biggest planning wins happen while you still own the company: retirement accounts funded from business cash flow, a personal safety net that doesn't depend on a sale, and years of tax planning ahead of a liquidity event. After the sale, we can only arrange what's left. Before it, we can shape what happens.
Three to five years, and more is better. That window is long enough to clean up the books, reduce how much the company depends on you personally, and get your own finances ready to live without it. A few months is enough time to react. It isn't enough to prepare.
A broker sells the company: finding buyers, running the process, negotiating price. I plan around the sale: what the proceeds need to fund, the tax picture across years, retirement income afterward, and how your family's finances change. You'll likely want both, doing different jobs. The broker's engagement ends at closing. That's roughly when the planning gets busiest.
Waiting until an offer arrives to start planning, so the tax structure is locked before anyone thoughtful sees it. Anchoring to a number a friend got rather than what your life requires. Underestimating how much identity and routine the business provided. And leaving the proceeds parked for years because nobody built a plan for the money to move into.
Usually, very little at first. There's rarely a penalty for letting the adrenaline fade before making decisions you can't undo. From there, most post-sale plans cover the same ground: an income plan to replace what the business paid you, a portfolio built to carry the decades ahead, and the conversations about second ventures, big gifts, and what comes next. The order depends on your deal structure and your tax year.
Start by measuring what the business actually paid you, which is usually more than the salary line: distributions, vehicles, insurance, travel. Then we build income from the proceeds: cash reserves for the near years, a portfolio designed to pay you monthly, and Social Security timed well. The goal is a paycheck you don't have to earn twice.
It depends on how the deal is structured: asset sale versus stock sale, cash at closing versus payments over time, and how the price gets allocated. Each choice shifts how much is taxed as capital gain versus ordinary income. I model the planning side across years; your CPA prices the specifics. Bring us both in before the letter of intent.
Almost always. Everything is handled virtually, so where you live is rarely a barrier. The only exception is a handful of states where I'm not registered yet, and if that's you, I'll tell you on our first call.