Exiting Your Business: Succession, Strategy, & Letting Go with Andrea Steinbrenner

On this episode of Adventures in Business, Amani and Mandi sit down with Andrea Steinbrenner, CEO of Exit Consulting Group, to chat about exit strategy for businesses. While most people focus on the financial side of exiting, Andrea makes it clear: there’s much more to a successful exit, and it doesn’t have to be scary. Andrea shares why every business should be exit planning at all times, her Canopy Method, and the one piece of advice she’d give her younger self. Whether you’re transitioning, selling, or preparing to retire, this episode is full of wisdom you won’t want to miss!

The Exit Triangle Most Business Owners Get Backwards

When people talk about exiting, the first question is usually: “What’s your number?” Andrea says liquidity matters – but at Exit Consulting Group, they think of exit planning as a triangle made of liquidity, relevancy, and legacy. And too often, owners put liquidity at the top.

Here’s the truth: you can structure the perfect deal – perfect price, perfect terms – and still not close it. Why? Because you haven’t untangled the emotional ball of yarn wrapped around your business.

Who are you when you’re not the CEO? How do you introduce yourself? What happens to your purpose? How do your relationships change?

Andrea puts it plainly: “We can always solve for liquidity. What we can’t solve for is relevancy and legacy.”

How Far Away Are You From Exiting Your Business?

One of the most fascinating patterns Andrea sees? Ask a room of business owners how far they are from exiting. The answer, almost across the board: five years.

Ask them again the next year? Five years. And the next? Still five years.

Five years feels safe. It’s close enough to see, far enough to avoid action. Exit planning is one of the top topics business owners want to talk about, and the top topic they avoid doing anything about. The solution? Do something today!

The Three Disciplines of Exit Readiness

Andrea and her team break exit planning into three core disciplines:

1. Owner Readiness

This is the “hard work that’s actually the hard work.” What motivates you? What’s your purpose beyond the business? What does life look like after? You don’t solve this in one meeting, but over time.

2. Business Readiness

Is your company viable without you at the center? If you’re the top rainmaker and decision-maker, you don’t have an exit-ready business. The goal is to move from owner-operated to professionally run without you.

3. Market Readiness

What’s your valuation today? Can you live with that number? What needs to move to change it?

What’s happening in your industry and the broader economy? 

The Family Business Dilemma

Then the conversation turned to something happening across the country: family businesses with no next-generation taker. Maybe the kids aren’t interested, or they’re not ready.

Andrea explains that generational gaps are widening. Parents are older when they have kids. That means when they’re ready to exit, their children may be 25 – not 45. That creates a capability gap.

Some possible solutions might include hiring interim leadership, creating or joining a family office structure, or leveraging multi-family office models for shared resources. And one particularly exciting development: Entrepreneurship Through Acquisition (ETA) programs at universities. These programs train young leaders to acquire and operate businesses, creating a bridge between aging owners and emerging talent.

The Hardest Part of Succession: Letting Go

Many founders say they’re stepping back… but don’t. They give the title away, but not the authority. Andrea sees this daily, and it usually comes down to two things:

Owners aren’t getting honest feedback, because employees don’t want to upset the person who signs their paycheck… and the owner hasn’t fully done their own internal work.

Solving this requires transparency, direct conversations, and often a third party willing to mirror back what’s actually happening.

The Most Successful Exits Have This in Common

When Amani asked what the best exits share, Andrea didn’t hesitate: they start early, take their time, surround themselves with the right advisors, and treat transition work as seriously as transaction work.

The owner keeps running the company as if they’re never going to exit – while professionals handle the deal mechanics.

The Canopy Method: Be the Tarzan

One of the most memorable moments of the episode was Andrea explaining her “Canopy Method.” Picture a rainforest. The forest floor is dark, dense, and gritty. The middle layers have filtered light. The canopy sees more sun. The treetops look like fluffy green from above.

Each layer has its own ecosystem, its own rules, its own reality. A frog on the forest floor doesn’t understand life above the canopy. A toucan at the top couldn’t survive below.

Businesses are the same way. Factory floor workers, middle managers, executives – each layer sees a different version of the company. Great leaders are like Tarzan. They understand every layer, can move between them, and can translate across them.

Being your “best Tarzan” means developing the mindset and skillset to understand the entire ecosystem – not just your corner of it.

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