You've spent 20, 30, maybe 40 years building this business. It's generated good income, supported your family, maybe put kids through college. Now you're thinking about retirement. You want to travel, pursue hobbies, spend time with grandkids. Maybe move somewhere warm. The problem: your retirement account is your business. No pension, modest 401(k), maybe some investments. The company is your wealth.
When you think about selling, the questions pile up. Is the business actually worth enough to fund retirement? Can you afford to retire at 62, or do you need to work until 67? What if the sale falls through? What if you're bored six months after selling? And the biggest question: how do you make sure you're not dependent on the business's ongoing performance after you exit?
Retirement exit planning isn't just about selling a business. It's about converting decades of work into financial security that supports the lifestyle you want for the rest of your life. The timeline matters. The structure matters. And getting it right means starting years before you actually want to retire.
The math for retirement exits is unforgiving. The sale proceeds from your business need to fund 20 to 30 years of living expenses. That's a fundamentally different calculation than extracting capital for a specific purchase or settling a divorce. If you sell for $3M and plan to retire for 25 years, you need that money to generate reliable income for a quarter century. The structure of the sale, the tax treatment, and how proceeds get invested matter as much as the headline number.
The timeline has more flexibility than health-driven or divorce exits, which is both an advantage and a trap. You could retire at 62, 65, or 67. Each year you wait potentially increases business value, but also costs you a year of retirement. At some point the trade-off tips: another year of grinding doesn't generate enough additional value to justify delaying the life you want to live. The trick is knowing when you've hit that point.
Emotional attachment creates a different kind of challenge. This isn't a business you're being forced out of. It's a business you chose to build and could theoretically keep running. The identity question hits hard: who are you without your business? For 30 years, when someone asked what you do, the answer was your business. In retirement, you need a new answer. Founders who don't prepare for that identity shift often sabotage their own exits, finding reasons to delay or pull back from deals because leaving feels like losing part of themselves.
Coordination with the rest of your financial life adds complexity. Social Security timing, Medicare eligibility, pension distributions if you have them, your spouse's retirement timeline, existing investments and real estate. The business exit needs to fit into this larger puzzle, not stand alone. And your spouse may have very different ideas about when retirement starts and what it looks like, which means alignment conversations need to happen before you commit to a sale timeline.
The Three-Legged Stool applies perfectly here: business transition (sell or transfer the company), personal transition (retirement lifestyle and identity), and financial transition (converting business equity to retirement income stream). All three need attention. Most people focus entirely on the business sale and then discover too late that they haven't planned for the other two.
Retirement exits have a luxury most other exit scenarios don't: time. If you're 60 and want to retire at 65, you have 5 years to build transferable value. That's enough time to move every driver significantly. The Value Builder System becomes a multi-year roadmap rather than a triage tool.
Financial Performance is where you start. Optimize profitability in the 3 years before sale. Buyers pay multiples of EBITDA, so increasing profit by 20% increases sale price by 20% or more depending on the multiple. Cut unnecessary expenses. Improve pricing. Streamline operations. Every dollar of additional annual profit multiplies in exit value, often by 3x to 6x depending on your industry.
Hub and Spoke gets addressed systematically over time rather than in a panic. Year 1: delegate operational decisions. Year 2: transition customer relationships. Year 3: step back to strategic oversight only. By the time you're ready to sell, you're already semi-retired. This proves to buyers that the business runs without you and makes the actual transition dramatically easier. It also gives you a preview of what retirement feels like, which helps you decide if you're really ready.
Growth Potential matters because buyers pay premiums for momentum. Show them the business has trajectory beyond your involvement. Build sales systems, marketing processes, a product development pipeline. Even if you won't be there to execute, demonstrating that growth infrastructure exists commands higher multiples than a flat or declining business.
Recurring Revenue directly impacts your retirement security. Converting customers to contracts or retainers increases both business value and predictability. Your retirement income from sale proceeds is more secure when the business you sold has predictable cash flow supporting its valuation, because buyers are less likely to come back with claims that you misrepresented value.
Switzerland Structure, Customer Satisfaction, Monopoly Control, and Cash Flow all support higher valuation. With the time advantage of retirement planning, you can address all 8 Drivers rather than triaging the worst ones. That comprehensive improvement is what separates a $3M exit from a $5M exit.
The Love It or List It decision in retirement context usually resolves to List It. But some founders discover through the value-building process that they can effectively "retire" from day-to-day operations while keeping ownership. Hire a CEO, step into a chairman role, collect distributions. That's actually the Love It path, and it works better than many people expect.
The ideal timeline is to start exit planning 5 to 7 years before your target retirement age. This gives you two full business cycles, since most businesses operate on 1 to 2 year operational cycles, to prove that improvements are sustainable and not just one-time spikes. A buyer who sees 3 consecutive years of growth pays more than one who sees a single year of improvement.
The minimum effective timeline is 3 years. That's enough time to move key Value Builder drivers, build management depth, and transition critical relationships. It's not enough to transform a business fundamentally, but it's enough to make meaningful changes that show up in valuation.
An aggressive timeline of 18 months works if you're already close. If the business scores 65 or above on Value Builder, the management team is solid, and you just need positioning and market preparation, 18 months gets it done. But this is rare. Most businesses have more work to do than their owners realize.
The right time to start is the moment you think "I might want to retire in the next 10 years." Not when you're burnt out and ready to quit tomorrow. Early planning creates options. Late planning creates compromises.
Financial planning integration is critical. Meet with your financial advisor at the same time you start exit planning. Model different scenarios together. A $3M sale at age 65 funds a very different lifestyle than a $2M sale at 62. Know the trade-offs before you decide on a timeline, not after you've already committed to one.
The Reality Check for retirement starts with the money question: how much do you need from the sale to retire comfortably? Not theory. An actual number, worked out with your financial advisor. We need to know what the business needs to sell for before we can build a plan to get it there.
Then we assess where you are today. The Value Builder Assessment score tells us what the business is worth now. More importantly, it tells us what it could be worth in 3 years if we address the gaps. Does that projected number support your retirement plan? If you need $4M to retire and the business is worth $2.5M today, we need significant improvement. That's realistic over 5 years. Over 18 months? Probably not. Knowing the gap early lets you adjust either the retirement plan or the exit timeline.
The gap analysis creates your roadmap. We focus on the drivers that matter most for your specific business type and timeline. Manufacturing company? Operational independence and financial performance move the needle most. Service business? Customer relationship transition and recurring revenue are the priorities. No two plans look the same because no two businesses have the same value gaps.
Simultaneously, we address the personal transition. You've been working 60-hour weeks for decades. Retirement isn't just stopping work. It's starting something new. We help you think through what post-exit life actually looks like. What will you do with your time? How will you find purpose and structure? The founders who plan this in advance are the ones who thrive in retirement. The ones who don't are the ones who try to buy their business back 18 months later.
The goal is clear: exit on your terms, with enough capital to support your retirement lifestyle, with a business that successfully transitions and protects the team you built, and with a plan for post-exit life that gives you purpose. We've worked with founders who retired at 58 and founders who kept going until 72. There's no universal right answer. The right answer is: financially secure, emotionally ready, and business positioned for successful transition.
"Kevin's knowledge put us in a position to reach markets that we hadn't ever reached before. He was worth 10 times what we paid him..."
— Dave & Jacci Brattin, Exited Owners of Armstrong-Citywide Hardwood Flooring
"Beyond business insight, Kevin provides the grounding you need when entrepreneurship gets turbulent. Every major decision he's guided has led to profitability. Not by accident, but by design."
— Mark DeGrasse, Founder of AI Branding Academy
Start at 60 at minimum, or 58 if you want optimal results. Five years gives you time to build real transferable value, not just position what you have. Three years is minimum to make meaningful changes. Starting at 64 leaves you scrambling or accepting lower value than the business could have commanded with preparation.
Depends on sale proceeds and retirement costs. If business sells for $4M and you need $3M to retire at 62 using a conservative withdrawal rate, yes. If business sells for $2M and you need $3M, no. This is why financial planning and exit planning must happen together. We help you model scenarios so you know the trade-offs before committing to a timeline.
Common fear, rarely reality. Most retirement exit regret comes from poor post-exit planning, not from selling itself. If you build a post-exit life with hobbies, travel, volunteering, part-time consulting, board seats, or angel investing, you fill the void the business left. If you retire to emptiness, you'll miss it. Plan the retirement, not just the exit.
Not immediately. If you're 5 years out, no need. If you're 18 months out, key leadership should know because you'll need them to help with transition. If you're 6 months out, tell anyone you'd want to give the opportunity to buy the business. Timing depends on your business and relationships.
Usually yes, if structured right. Buyers often want the founder to stick around 6 to 12 months for transition. Some deals include consulting agreements. But don't sell thinking you'll stay forever. Buyers want transition, not permanent employment of the previous owner. Build that expectation into your planning.
Wherever you're located in the Kansas City metro, whether that's Overland Park, Leawood, Olathe, Lenexa, Shawnee, Prairie Village, Lee's Summit, Blue Springs, Liberty, Gladstone, Independence, Parkville, Brookside, Waldo, or the Plaza, retirement exit planning gives you the timeline to maximize business value and ensure financial security for the next chapter.