My Chat with an Entrepreneur Revealed That Even Successful People Have Fears About Money

For business owners, it’s essential to know one’s wealth gap in order to gain this confidence

Brent Rupnow
Jul 9, 2020 · 6 min read

“They’ll probably take me out of here in a pine box.” Evelyn prefers a blunt tone in conversation and this time was no different. I had asked her if she ever thought about post-work life and she brushed it off with a shrug and the pine box comment. I smiled.

We didn’t know each other really well. We had been introduced by a mutual friend and had some brief conversations. She reached out to me. She said she needed my help. But every time the discussion got to her personal vision, the guard came up.

The entrepreneur who knows she needs help but is afraid to let someone help her. Even when the person doing the helping comes from the recommendation of a close friend.

Sharing the details of one’s business is personal.

Whoever came up with “it’s business, not personal” really doesn’t get it.

Evelyn started her orthodontist practice 27 years ago. She told me that she didn’t think she was going to make it. The mountain of student loan debt. The inability to afford full-time office staff. The rent. The warnings from her dad about a young woman in the office by herself in early evenings when the part-time staff went home.

But she made it. And big.

Evelyn’s practice had grown to 3 offices and 13 team members including 3 other orthodontists. She owns her locations. No rent. At least to someone else. She owns a historic mansion on the most exclusive street in her city. Her three kids all made it through college without debt. She lost her husband a few years ago to cancer but in every other way, Evelyn was flying high and feeling youthful at age 63.

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Photo by Geo Days on Unsplash

So maybe the “pine box” comment is more about loving what she is doing and a lack of desire to see herself doing anything else. Many planners don’t like to meet with clients at their business but I do because I can see them in their element. Sure, there are more distractions. I like to see the business owner with their creation at least some of the time. Seeing Evelyn with her creation that day convinced me that her passion for her practice was real.

Part of the sense came from the experience of having worked with entrepreneurs for so long. I trod carefully with the financial detail questions. I didn’t want to pry but needed to get a picture in order to help. The details slowly emerged.

Despite Evelyn’s high net worth and strong cash flow, she didn’t have a lot in liquid, investable assets. Everything was either in the business or in real estate. Her retirement accounts were less than someone with far less than her annual income might have.

I think that, in a sense, Evelyn feared being told that her retirement savings were grossly inadequate.

If you’ve ever watched sports on television, you no doubt have seen commercials explaining that you need to ‘know your number’.


How much money you need to have saved in order to retire.

It’s repetitive and ubiquitous.

To many business owners, ‘know your number’ presents an insurmountable problem.

The entrepreneur made sacrifices to build the business. Making sure that everyone else was paid…sometimes meaning no paycheck for the owner.

Time sacrifices. Not having vacations. Loss of family time.

And often minimal retirement funding in lieu of reinvesting dollars in the business itself.

The business owner sees their retirement account balances and sees no way for them to transition out of working and into something else. I was convinced that this was the case for Evelyn and the cause of her pessimistic tone.

I decided to change her focus. “Do you know your wealth gap?”, I asked. I knew she didn’t know what this meant.

“Wealth what?” I got a puzzled and annoyed look.

I chuckled and hoped what I’d say next would help Evelyn to open up.

She wasn’t confessing her fears. I took a chance and hoped I had guessed correctly about what they were.

“If you look at your total net worth now”, I explained, “and look at the amount you’ll need to make work optional…it’s the difference between the two.”

“How do I know how much I’ll need?” she asked sarcastically. “I like nice things and there’s no way I can ever put enough in retirement savings to catch up to what I spend.”


Evelyn’s vision was stuck in comparing her current retirement savings to her current lifestyle. Without doing any type of calculating, she knew there was a gap. She just feared that it was so large as to be ridiculous to even consider filling it.

“Evelyn, this is why you have me here!”

I explained that for successful entrepreneurs like her, we need to look beyond the retirement account balances. We need to understand the value of her business and real estate.

Her ability to make work optional at some point was going to hinge on making her business transferable and attractive to a third-party buyer.

It’s not that retirement balances are meaningless. But if there is a gap between what she wants and what she has, the business is very likely going to play the biggest role in closing it.

“I’m not selling my practice,” she said. “What if one of my kids wants to take over?”

Whether she was going to sell, expand, or transition to one of her kids, she was going to need to make her practice able to be sold. None of us are going to live forever so in some way, shape, or form, the business is going to be transitioned eventually.

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Photo by Chris Lawton on Unsplash

“Why not prepare?”, I said.

“Well, how do I know how much I need?”

The first thing we needed to do is get really clear about what it is that Evelyn really wants.

I was pretty sure that what she really wanted was not to be carried out of her business in a pine box.

If she was going to maintain her mansion, travel the world, and open up a charitable foundation, that was going to require a lot of money.

If all she wanted to do was sit on the front porch of a smaller home, spend time with her grandchildren, and garden, it would require a lot less.

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Photo by Robert Anasch on Unsplash

Everyone thinks that because entrepreneurs are visionaries and dreamers that they know what they want. Maybe in the business.

Not so much in planning their next act of life.

This is why we need to spend so much time in the beginning on the vision of what that next act will really look like. We need to ask a lot of questions and stay in those questions until the vision becomes clear and the path forward is defined.

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Photo by Kevin Oetiker on Unsplash

We set up a time to get together and set forth Evelyn’s vision. We mapped out the things that were important. From there, we could put a price on the various parts of the vision and truly figure out what the amount of wealth that was needed to accomplish her vision.

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Photo by Kyle Glenn on Unsplash

In Evelyn’s case, the gap was a lot smaller than she thought. We focused on improving the transferability of her business and didn’t have to do any long-term strategic growth. She still didn’t want to sell.

But she is ready.

For whatever comes next.

Brent Rupnow blog

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Brent Rupnow

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Keep moving forward every day! Certified Financial Planner, Certified Exit Planning Advisor, Christian, adventure lover, aesthetic

ExtendNode’s Blogs for Entrepreneurs

We share educational know-how and inspirational stories written for and by founders, business leaders, and investors.

Brent Rupnow

Written by

Keep moving forward every day! Certified Financial Planner, Certified Exit Planning Advisor, Christian, adventure lover, aesthetic

ExtendNode’s Blogs for Entrepreneurs

We share educational know-how and inspirational stories written for and by founders, business leaders, and investors.

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