EP04: Exit Strategy for Your Health & Wealth: How to Prepare for the One Transition You Can’t Avoid

“Exit planning isn’t just about numbers. It’s about purpose, identity, and ensuring the business doesn’t die the day you walk away.” —Kelli Olsheski

Kelli works with entrepreneurs through Merrill Lynch’s Olsheski Kozisek Group in Fort Collins, Colorado. She’s not just a numbers person—she’s a legacy architect. Her work helps business owners turn decades of sweat equity into lasting financial independence… without sacrificing their health, marriage, or identity in the process.

According to Kelli, most founders fall into one of three traps:

• They believe they’ll “never” exit.

• They assume they can sell whenever they’re ready.

• They plan the financials but ignore the emotional toll.
  
  

But here's the truth: Every business owner exits—voluntarily or not.

And when you're not ready, that exit can come at a heavy cost: lost valuation, burnout, family stress, or personal health breakdown.

Kelli calls them the 5 D’s—and they account for most forced exits:

• Death

• Disability

• Divorce

• Disease

• Disaster
  
  

You might plan to exit at 75… but a single diagnosis or economic shift could pull the plug at 62.

That’s why proactive planning isn’t optional—it’s urgent.

Let’s talk valuation.

You may have $5M in revenue, a team of 20, and a full client roster—but if you are the business, then your business isn’t worth what you think.

Here’s the hard truth:

“If you're the best salesperson, the operations lead, and the face of the company… your business has no transferable value.” —Kelli Olsheski

Buyers—especially private equity—want businesses that can function without the founder. That’s where the concept of transferable value comes in.

You don’t just want a profitable business.
You want a sellable business.

Kelli breaks down business value into four key areas. Ignore these, and you leave money (and peace of mind) on the table:

1. Human Capital

Who’s on your team? Can they run the show without you?

Strong teams attract higher multiples. Founder-dependent teams don’t.

2. Structural Capital

Do you have SOPs, CRM systems, contracts, legal protections, and documented workflows?

A business with systems sells. A business run from your head doesn’t.

3. Customer Capital

How diverse is your client base? Do any clients make up over 25% of your revenue?

Too much reliance on a few accounts = risk for buyers.

4. Cultural Capital

What’s your employee retention rate? How aligned are your values?

A healthy company culture signals long-term viability to investors.

If you want a higher EBITDA multiple (and less deal friction), these four areas need to be audit-ready 3–5 years before your exit.

Let’s say you have sold the business. Now you’re sitting on liquidity, but something’s off.

• You’re restless.

• Your energy is inconsistent.

• Your purpose feels foggy.

• Your body is sending you new (and confusing) signals.
  
  

That’s not failure—it’s a natural identity transition. But if you don’t address it, it can lead to regret, depression, or chronic health issues.

“You can golf for 4 hours a day… but after 6 months, that gets old fast.” —Kelli

The solution?

Plan your life post-exit just as seriously as you planned your liquidity.

1. Rebuild Your Identity Outside the Business

Men who led companies often struggle to redefine success outside their professional identity. Legacy-minded men must ask:

• What am I building now?

• What wakes me up in the morning?

• Who benefits from the next decade of my strength?

2. Prepare for the Real Cost of Retirement

Most business owners underestimate their future expenses.

Why? Because they’ve run personal expenses through the business for decades—cars, health insurance, travel.

“You may be living a $250K lifestyle off $45K in reported income. That changes overnight when the business is gone.” —Kelli

Factor in unexpected medical costs, home repairs, and market volatility—and suddenly your “nest egg” might need to be 30–50% bigger than you thought.

3. Optimize Your Health Now—Not Later

Here’s what few wealth advisors will tell you:

You can’t enjoy your wealth if you don’t have the health to match.

Many post-exit men feel exhausted, foggy, or emotionally flat—and traditional medicine tells them it’s “just aging.”

Tiger Medical disagrees.

We believe what you feel is real—and fixable. Brain fog, fatigue, sleep issues, or hormone imbalances aren’t a new normal. They’re signs to take action.

Kelli’s framework for exit planning includes aligning:

• ✅ Personal financial readiness

• ✅ Business valuation and transferability

• ✅ Lifestyle design and legacy planning
  
  

But here’s what Tiger adds:

• ✅ Metabolic & hormonal optimization

• ✅ Personalized longevity strategy

• ✅ Data-driven vitality tracking
  
  

“You didn’t exit to decline. You exited to thrive.”

If you don’t know where your energy, inflammation, stress resilience, or cognitive function stand today—how can you plan to stay vital for the next 20 years?

Let’s make it tangible.

If your EBITDA is $2M and you exit at a 5x multiple, you sell for $10M.
If you improve your business structure, team, and customer capital—and get a 12x multiple—you exit at $24M.

Same business.
Very different outcome.

This is what value planning does.

Now… imagine if your health is treated the same way.
What if you invested today and added 10+ vibrant years of clarity, energy, and presence?

What would that be worth?

Legacy-driven men aren’t wired to “sit back.” You want impact. You want clarity. You want to feel good while doing what matters.

That requires intentional reinvention:

• Coaching.

• Data.

• Structure.

• Purpose.
  
  

As Kelli puts it:

“A good exit strategy is just a good business strategy. A good retirement is a well-run life—with you at the helm.”

And we’d add:

A strong body is the foundation for everything else.

If this conversation opened your eyes… don’t just think about change—take action.

Start with the Tiger Health Assessment:

🔬 70+ biomarker lab panel
🧑‍⚕️ 1:1 consult with a Tiger-trained physician
📈 Personalized roadmap to optimize your next decade

It’s the most strategic $497 you can spend right now.

🟡 Don’t normalize decline. Optimize instead.

👉 Start Your Tiger Health Assessment Today »

You mastered your business.
Now master your biology.

Whether you're 6 months or 6 years from your exit, the time to align your business value, your health, and your legacy… is now.

Because wealth without health is regret.
And retirement without purpose is decay.

But when you combine strategic exit planning and personalized health optimization?

That’s when you go from success… to significance.