Why Business Owners Regret Selling — And How Exit Planning Prevents It
Exit planning for business owners is one of the most important – and most overlooked parts of running a successful business. In this in-depth interview, business broker Joe Steigman sits down with Austin Coley, Wealth Advisor at McCall & Associates, to talk all things exit planning, wealth strategy, post-sale identity, tax optimization, and how to avoid the most common — and costly — mistakes when exiting your business.
Whether you’re 1 year or 5 years away from selling, this conversation will help you protect your legacy, maximize your enterprise value, and prepare for life after the sale.
For many small business owners, their company is more than a livelihood — it’s a legacy. But despite the emotional and financial weight behind selling a business, over 75% of owners regret their decision just one year after exit.
Why? Because most wait too long to plan — or only focus on the sale, not the life after it.
In a recent interview with Austin Coley, wealth advisor at McCall & Associates, we explored the strategies business owners can use to ensure their exit is intentional, profitable, and fulfilling.
Here are the biggest takeaways from our conversation:
1. Exit Planning Is About More Than the Sale
While brokers like myself focus on maximizing the value of the business asset, Austin takes a broader view: aligning your personal, financial, and business goals so you can thrive post-exit.
“Exit planning isn’t just about selling a business — it’s about building one that’s transferable, ready, and attractive at any time.”
2. Know Your “Golden Number”
Your golden number is the net amount you need to walk away with after taxes, fees, and debt to live the life you want.
Austin’s firm uses financial modeling to help business owners understand what that number is — and what type of sale scenario will get them there.
“It’s not about how much your business is worth — it’s about how much you need to live your life after it.”
3. Start Planning 3–5 Years Out (At Least)
One of the most common — and costly — mistakes is waiting until you’re ready to sell to start preparing.
“If you didn’t start yesterday, the next best time is today.”
- Starting 3–5 years out gives you time to:
- Reduce owner dependency
- Improve financials
- Build a management team
- Execute tax strategies like QSBS or donor-advised funds
4. Prepare for the Buyer’s Perspective
As a business broker, I absorb a lot of the critiques that potential buyers have. Working with advisors like Austin ahead of time allows us to fix red flags before they tank your valuation.
“You want to be defending small formatting issues, not core operational ones.”
5. Plan for Life After the Sale
A major reason sellers regret their exit is loss of identity. They go from being at the center of operations to not knowing what to do Monday morning.
Whether it’s:
- A new hobby or business
- Philanthropic work
- Travel or family time
… planning your purpose is just as important as planning your payout.
“Selling well means stepping into something new, not stepping away from everything.”
6. Taxes Matter — A Lot
With the right planning, business owners can reduce their tax burden by hundreds of thousands or more.
Strategies include:
- Long-term capital gains treatment
- Installment sales to reduce taxable income in a single year
- Donor-advised funds for philanthropic giving
- QSBS structuring for eligible C corps
“It’s not about avoiding taxes. It’s about being intentional with what you’re already doing.”
Working With a Trusted Exit Team
Both Austin and I agree — business owners need a team to guide them through this process: financial advisors, CPAs, attorneys, and brokers working together, not in silos.
“You need good professionals in every lane. One person can’t do it all — but the right team can do everything.”
If you’re even thinking about selling your business in the next 3–5 years, now is the time to get your plan in motion.
Business Resiliency, Valuation, and Exit Success
Exit planning isn’t just for those ready to sell. It’s about making your business more resilient, valuable, and transferable — no matter when the exit happens.
Remember: 50% of all exits are involuntary. The best defense is a proactive strategy that aligns your business and personal life for long-term success.
📞 Need help starting your exit strategy or hiring a general manager to reduce your owner dependency?
Let’s talk.
📩 joe@legacy-eta.com
📱 615-240-7901