Many founders start a business for freedom. You want control of your time, income, and impact. But somewhere along the way, that freedom can turn into something else - dependence.

You depend on your business for your lifestyle.
Your team depends on you for every decision.
And when the time comes to sell, you realize: no one can buy you.

Lifestyle vs. Legacy

A lifestyle business pays for today.

A legacy asset pays for tomorrow.

In a lifestyle business, your name is the brand, your hands touch every process, and revenue rises or falls on your energy. In a legacy asset, the business runs on systems, leadership, and repeatable value that outlives you.

When I sat down with Karl Sigerist from the Shaughnessy Group, on The Cash Rich Exit Podcast we talked about what makes that shift possible. He works with founders in the $5 million to $50 million revenue range - owners who’ve built something meaningful, but not always transferable.

Karl reminded us that selling a business isn’t like selling a house. You can’t just put it on the market when you’re ready to move. A buyer isn’t only buying revenue. They’re buying structure, predictability, and potential.

How do you prepare for that?

Step 1: Separate yourself from the business

The biggest obstacle to transferability?

You.

If every client, supplier, or key employee relies on you personally, there’s no business to buy. You’ve built a great job, not an enterprise.

Start by documenting processes, training your leadership bench, and creating accountability systems that don’t depend on your daily presence.

Think of it like teaching your business to walk without you holding its hand.

It might wobble at first, but every step builds strength.

Step 2: Build professional infrastructure

Buyers and investors look for evidence of discipline - in finances, governance, and communication.

That means clean, timely financials.

Regular management meetings.

KPIs that are tracked and understood.

Contracts that are current and compliant.

When these pieces are in place, you’re not only preparing for an eventual exit. You’re also freeing yourself to focus on growth and innovation now.

Karl says it well: preparing for sale makes every part of your business better. You’ll lead with more clarity, your team will perform with more confidence, and your valuation will rise naturally.

Step 3: Replace emotion with strategy

Most founders are emotionally tied to their business. It’s natural - this company likely represents your greatest achievement. But emotion can cloud judgment when it’s time to transition.

The shift comes when you start to view your business as a wealth-building vehicle, not a reflection of your identity.

Ask yourself:

• If I were buying this company, what would I want to see?
• Is my business dependent on a few key clients?
• Could it survive a year without me?

If any of those answers make you uneasy, that’s not failure - that’s your opportunity to build value before an eventual exit.

Step 4: Think legacy, not just liquidity

A cash-rich exit isn’t only about the money.

It’s about continuity.

The people who’ve grown with you.

The customers who trust you.

The impact your business makes in the community.

Planning for legacy ensures that when you do sell, you pass on a thriving enterprise - one that continues to create value and employment long after you’ve moved on.

Your next step

If you’re a founder earning between $5 million and $50 million, it’s time to ask a different question: Is my business sellable, or just successful?

Building transferability takes time, but it’s one of the most powerful investments you can make.

Start by assessing your wealth gap - the space between what your business is worth today and what you’ll need to fund the next chapter of your life.

You don’t have to do it alone.

Connect with me on LinkedIn or visit colleenoconnellcampbell.com to begin building a legacy that’s both profitable and purposeful.

TTFN - ta-ta for now!

Colleen

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