TRANSCRIPT
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#72 - Exit Planning for Business Owners: Preparing Financially, Personally, and for Legacy
Introduction
Eric Blake: We are in the beginning stages of one of the largest wealth shifts in history. It is being called the Great Wealth Transfer, and a growing share of that wealth is being generated by women business owners. Whether you are leading a company now or preparing for the day that you will sell, the decisions you make before that transition can determine not only your financial future, but also your legacy.
Welcome to another episode of the Simply Retirement Podcast, where we want to empower and educate women to live your retirement on your terms. I am your host, Eric Blake, practicing retirement planner with over 25 years of experience, and founder of Blake Wealth Management. I would not be the man I am today without the women in my life.
We have talked about the Great Wealth Transfer in the past, and we are seeing more women than ever not just inheriting wealth, but actually creating it—often through the building and selling of successful businesses. The wealth from those ventures does not just disappear when the business changes hands. It becomes the fuel for the next chapter of life.
For some women, that means a well-earned retirement. For others, it might be the launchpad of a new venture, more time with family, or a focus on philanthropy. That is why today’s conversation is so important. Joining me is Renita Wolf, founder and CEO of Pole Wolf Partners, a boutique exit planning advisory firm that helps middle-market business owners prepare for and navigate business exits, aligning financial outcomes with personal and legacy goals.
Renita, welcome to the Simply Retirement Podcast.
Renita Wolf: Thank you, Eric. I am excited to be here and I am looking forward to our conversation.
Renita’s Background
Eric Blake: Renita, can you start by telling us a little bit about your background and what led you to start Pole Wolf Partners?
Renita Wolf: I had a successful corporate career for over 30 years. In those roles, I was a senior finance manager for Fortune 50 companies and also a chief financial officer for a smaller company. One of the things I did in my work was mergers and acquisitions.
I wanted to continue working, but I wanted to do something different than corporate. I wanted to have a bigger impact. Based on what I had learned at corporate about mergers and acquisitions—where we would acquire smaller companies to consolidate them into a larger organization—I saw that many times the founders were not pleased with the transaction once it was complete.
Because of my experience with transactions and the technical side, I understood that part well. I wanted to bring that to business owners and help them exit their businesses while being prepared when that time comes for them.
Would you like me to continue in this cleaned-up, formatted style and move through the entire transcript section by section (e.g., Emotions of Selling, Financial Planning, Mistakes, Preparing for What’s Next, Key Takeaways)? This way, you’ll have the whole transcript polished and structured.
Emotions of Selling a Business
Eric Blake: One of the things I have always been fascinated by—and what we focus on in this podcast—is the emotional preparation of retirement. That can be even more important than the financial preparation. I cannot imagine that selling a business is not very much along those same lines.
Can you talk about the emotions that come with selling a business, preparing to sell, or even just thinking about the stress of what life might look like after? How do the emotions of retirement compare to the emotions of selling a business?
Renita Wolf: I would not really compare them because I think they are many of the same things, as I said when I left my corporate career. What I would say is that many times people are unprepared because they never think about it. They do not know what to expect or what to do next, particularly when they are looking at eventually exiting their businesses.
They are totally unprepared, and that is unfortunate. So I help them get ready.
The Importance of a Team
Eric Blake: I know one of the other things you stressed before we started our conversation today was how important it is to have the right people working together. A lot of people think, “My financial advisor will handle my money.”
But how important do you think it is for someone like yourself, an exit planning professional, to be in communication with their financial planner when going through this process?
Renita Wolf: When I talk to business owners, it is very common for them to have accumulated some wealth. They usually have a wealth and financial advisor, which is very good practice. Often, the financial advisor has placed an estimated value of what the business might be worth if the owner were to exit.
So when you look at a total roll-up of the net worth of an owner, it includes an estimate of the value of their business. The surprising part for business owners—and this is a statistic that is commonly cited—is that more than 80% of businesses never sell.
Most owners who have a business value reflected on their personal balance sheet have never had that value validated. They may think it is worth more or less than it really is. So they may think they are prepared for retirement when, in fact, they are not.
That is one of the first things I ask clients about when I start working with them.
The second thing I ask—and this is another surprising area—is not about them. It is: Who would you want to buy your company?
Most people never think about that. They think, “Oh, I want the most money and I want to get out as quickly as I can.” But as it gets closer to the transaction, I see some owners back out because they do not like the buyer, the package, or the earnout that may require them to stay on for a while.
So there are a lot of surprises. It is not as straightforward as people might think.
Exit Planning vs. Financial Planning
Eric Blake: When you think about exit planning and what you do, how is that different from traditional financial planning? What goes into it?
Renita Wolf: How an exit planner works with a business owner is different. A financial advisor is part of the team that supports the business owner. When someone is looking at exiting their company, it becomes a transaction where somebody wants to buy it.
Once you have your ideal buyer in place, who is that person? The financial advisor is part of the team, but other members include their CPA, their attorney, and then also a broker if it is a smaller company or an investment banker if it is a larger company. For example, something that is over $10 million.
Most of those people are totally focused on the transaction. I work with business owners before they get to the point of taking their business to market.
The first thing I ask is, “Who ideally would you want to buy your company?” Then I ask, “What would you like your life to look like after you sell your business?”
After that, we do a preliminary valuation to see what it is worth and if it is close to the number they have on their personal balance sheet. That shows if it is money they could potentially retire on once they leave the company.
Because I worked in corporate and have transaction experience, I also help them get things cleaned up before they go to market. It is more than window dressing. It is making sure their financial statements are compliant with generally accepted accounting principles.
In smaller businesses, it is not uncommon to see owners who have worked with their CPA to minimize taxes by running expenses through their personal income statement. That reduces reported income, which is fine if that is their motivation. But it is different when selling a business because a buyer wants to know what profit they could realistically achieve.
So, while the deductions are legitimate, the perspective has to change.
Why Start Early
Eric Blake: You talk about why it is important to start early. If you need to clean things up, that takes time. Can you share the benefits of beginning exit planning well before you want to sell?
Renita Wolf: Yes. Cleaning up the financial statements and making sure they are GAAP compliant is one benefit. Sometimes we even go back and restate statements to reflect a buyer’s perspective rather than just tax minimization.
Another key is ensuring the business does not depend solely on the owner. Most buyers want to take over directly without the owner staying on. If success depends on the owner, the business is less attractive.
So what has the owner done to transition themselves out of day-to-day operations? Have they hired a chief operating officer or a CEO for a larger company so the owner does not need to stay?
Other examples include digging into contracts to make sure they are transferable to a buyer and putting in incentives to keep employees after the sale. Buyers want to know the team will stay if they plan to continue the business as-is.
These steps take time. They are doable, but they require effort. And this is where the emotional part becomes very real. Many owners struggle to let go. They believe no one can take care of customers or vendors the way they can. That mindset can create problems during a sale.
From my role, I come in and work for the owner. I do not get a commission on the transaction. I am not siloed like an attorney or CPA. I look at the total picture and serve as a confidant to the owner.
Recently, I worked with an owner who had a buyer and even brought in an investment banker, but he was not ready. The deal fell through because the business and the owner were not prepared.
It was not just the tactical side but the emotional side. Buyers focus purely on the transaction. They use language that can feel disrespectful to an owner who has spent decades building their company. It is not intended that way, but it feels that way. I help owners prepare for that dynamic so they do not walk away unprepared or overwhelmed.
Preparing for Life After Business Ownership
Eric Blake: We did an episode recently on the “Thousand Hours of Retirement,” which was basically saying if someone has worked for 30 years and retires, they need to come up with about four hours a day of activities. But for business owners, it might be eight to twelve hours a day they now need to fill, since their lives were centered on the business.
How important is preparing for the time management aspect of leaving a business, and what might life look like on the other side?
Renita Wolf: We all have different things we enjoy doing, so it is an individual question. But I remember one owner I worked with who confided, “I don’t know what I’m going to do when this is over.”
I was not trying to solve his problem, but I started listing things: hobbies, travel, moving, or spending more time with family. I do not recommend major life changes in the first year after selling, but some travel or family time can be great.
The idea that really lit him up was when I said, “You could take some of the money from your sale and invest in other companies, serving as an advisor or board member without running the day-to-day business.” His whole perspective changed. He could see a meaningful path forward after selling.
Common Mistakes in Exit Planning
Eric Blake: That’s powerful. From your perspective, what are the bigger mistakes people make when preparing for an exit?
Renita Wolf: The first mistake is not even thinking about it or preparing ahead of time.
I also want to mention spouses and families. This applies to men and women alike. Often, it is the spouse or children encouraging the business owner to exit—sometimes because of health concerns. Many owners are in their sixties, and health starts to decline.
If they have not prepared, there may be no way out of the business. That puts the family in a difficult spot.
It can start with a simple question: What would you like to be doing in five years? That gets the owner thinking.
But if they delay too long, unexpected events like illness or accidents can devastate both the family and the business. I once worked for a small tech company where the founder was killed in a car accident. Without preparation, the family and company were left extremely vulnerable.
Even if someone says, “I never want to retire; I love what I’m doing,” they still need to prepare. Having things in order—qualified staff, organized books, transferable contracts—means the business runs better now and the owner can take time away without worry.
It is like having a life insurance policy. You hope you don’t need it, but the security is invaluable.
Defining a Successful Exit
Eric Blake: Beyond the sale price, what do you think defines a successful exit?
Renita Wolf: To me, success is being in a position to do what you want, when you want, and with who you want.
That was why I started my own company after corporate life. It’s about freedom and choice. Business owners and their families being prepared to reach that point—that’s true success.
Recommended Resources
Eric Blake: For those who want to learn more, are there books or resources you recommend?
Renita Wolf: There are many good books on exit planning. You can find them easily on Amazon. They help you understand what to expect and the value of preparing.
The important thing is not to focus only on the transaction or ask, “What’s the multiple? What could I get for my business?” That is not the place to start. Your income statements need to be normalized and compliant with GAAP before you can think about multiples or EBITDA. Buyers care about cash flow, but you need to ensure the numbers tell the right story.
How to Connect with Renita
Eric Blake: How can listeners connect with you and learn more about your work?
Renita Wolf: People can find me on LinkedIn, or visit my website at polewolfpartners.com.
I also offer a free 30-minute call. It’s not a sales call—I’m not a salesperson. I love hearing about people’s businesses, offering some insight, and pointing them in the right direction, even if they aren’t ready yet.
Eric Blake: That’s excellent. We’ll include links to your website, your free assessment, and your LinkedIn profile in the episode summary. Renita, thank you so much for joining me today.
Renita Wolf: Thank you, Eric. I’ve enjoyed our conversation.
Eric Blake: And thank you to our audience for tuning in as well. If you are a business owner, remember—a successful exit doesn’t happen by accident. It takes planning, the right team, and a clear vision for what comes next. I encourage you to reach out to Renita, find her free resource, go through that questionnaire, and see what direction it takes you.
That’s it for today’s episode. For all the links and resources, you can visit thesimplyretirementpodcast.com.
Until next time, please remember—retirement is not the end of the road. It is the start of a new journey.
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