Beyond the Money: What Selling My Business Taught Me About Human Nature

Or... Why you should get excited about people blocking your way.

Oct 28, 2024

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In 2015, I sold my business. I’d started the business from scratch in late 2006 with $500 of inventory, a book called “How to Build a Yahoo Store,” and a lot of unearned, unexplainable confidence. In the seven-plus years since I started, the company had ballooned into a multi-million dollar monster. I loved my employees, my products, and the breadth of relationships I had built with my customers and suppliers. However, growing the company was no longer an aligned desire. And it wasn’t about to stop growing.

Before I even started, I was clear on my objectives. I wanted to build a business to support my life rather than wasting a life supporting a business. I wanted to replace my salary so I could stay home with my daughter. I wanted location independence - a business I could run from anywhere with a Wi-Fi connection so our family could travel the world. These were my Ultimate Whys - my aligned desires.

The business thrived on both fronts. I was home for my daughter from the day she entered first grade. We could move to an ocean-front home in The Bahamas for a few years, and when my daughter was in ninth grade, we home-schooled and spent a year traveling through Europe. Then, we could move back to Florida so my daughter could attend the school she wanted. But now, the business was more than I’d bargained for. Now, I had eight worldwide employees, ten Chinese factories (that I had to visit annually), and a massive warehouse in Kentucky. Now, I had to take an extra annual mortgage on my house every year to fund the millions of dollars of inventory we had to pay for in January that didn’t sell until the window between Thanksgiving and Christmas. The weight of responsibility felt like a boulder, perched and wobbling on my shoulders. Although the business was on the cusp of significant mind-bending revenue numbers, I’d had enough.

I listed the business through a broker on a Tuesday afternoon, and by Wednesday morning, I had more than one full-priced offer. I chose the best one and signed the sales contract. This began three months of a period called “due diligence.” During due diligence, the buyer (I’ll call him Frank, but you and I both know that wasn’t his name) had the opportunity to dig deep into the company’s history and financials to ensure he was getting what he paid for and, trust me, Frank brought a forklift along for the job. The problem was that Frank had only one Ultimate Why… Money.

Frank’s Ultimate Why was so all-encompassing he couldn’t imagine the possibility that anyone would have any other. Why would I sell a robust and healthy business that was taking off? The company generated significant revenue for very little work because of the processes and systems I had painstakingly implemented and was poised for growth. What was wrong with it? There must be something wrong with it.

Frank was what we heroines call a Threshold Guardian. In the world of story, a Threshold Guardian is a character archetype representing a significant challenge for our heroine. These archetypes try to prevent our heroine from getting what they want. They guard the door that leads to the secrets of life revealed on the other side and are meant to test our heroine’s strength and courage. The Threshold Guardian ultimately decides whether the heroine is worthy.

You have a Threshold Guardian in your life, right? It’s the manager who won’t recommend you for that promotion. Or the friend telling you that going back to school at your age would be embarrassing. When you see your Threshold Guardian, does your stomach drop into your shoes and the hair rise on the back of your neck?

Frank was determined to break me. According to Frank, this was too good to be true. There was something I was hiding. There was something very wrong with the company, and he would find out what it was. The stress! Holy moly. It was like I had a thousand metal threads inside my chest cavity, and every few minutes, one of them shattered. Ping! When all the strings pinged, I knew I’d probably die.

I could see life without the business on the other side of his guarded door, but I couldn’t reach it without Frank’s approval. I was absolutely terrified he’d back out of the sale. If he backed out, his withdrawal and condemnation would be the ultimate symbol of my failure. I would let everyone down.

Frank’s voice thundered over the speakerphone with disparaging words about the financials and my decision-making. He claimed I was overpaying my Operations Manager (Yes, I was. On purpose. I trusted her and wanted to replace her corporate salary.) He said I didn’t understand the accounting (not my forte; I’d learned to hire out my weaknesses and had a savvy accountant who is still with me today).

He said a lot more.

I hate to admit that Frank intimated me, but he did. Because, really, who did I think I was having a million-dollar business in the first place? Frank’s right. It’s a fluke. There’s something wrong with it that I’m too dumb to understand. Imposter syndrome and self-doubt made me weepy and emotional (I hereby apologize to my husband and daughter for my behavior during this period.)

Then I was angry. How dare he? After all, he hadn’t built a successful business from the ground up. I had done that - and he was buying it!

But the more emotional and angry I became (Why oh why do I cry when I’m angry!), the more he judged my ability to run a business and questioned its authenticity. Which sent me down a spiral to Despondent Land (You’ve been there, right? You know it’s not pretty.)

So here’s the thing I have since discovered about Threshold Guardians... they are NOT your enemy. I mean, did Anna hate her sister Elsa in Frozen? Did Harry Potter despise the Sorting Hat? These people, places, or things have a purpose. Yes, the Guardian can even be a thing - think of the doorknob in Alice in Wonderland. Anyhoo, you should celebrate the appearance of a Threshold Guardian in your life because it means something is about to change. All you need to do now is make some choices because choice creates change, and change creates opportunity. So, what choices do you make? How do you defeat the Threshold Guardian and make him open the door to let you through to the special world you know is on the other side?

Accept there is something the Threshold Guardian has to teach you. Frank taught me to live by my Ultimate Whys.

Once I stopped crying, I focused on my Ultimate Why of empathy. The man could think of nothing but money, so of course he didn’t understand my drive to give up a successful company on the rise to spend more time with my daughter and do something more creative. He couldn’t understand that money wasn’t a driver for me. And he was afraid. He was scared of making a terrible mistake.

Accept you can’t beat a Threshold Guardian without courage and faith. Frank taught me confidence.

Once I stopped quivering behind my business broker, I chose to take stock and recognize the gift I was giving him. I had built this company from nothing by myself. I was handing over a growing concern. I could stand up to the bully and have confidence in my creations.

Accept one of the essential elements of the Heroine’s Code: Humility. Frank taught me to be humble.

Frank didn’t know me from Adam. He didn’t know what a hard worker I was. He didn’t know the blood, sweat, and tears that had gone into the business. He didn’t know if it would be everything my broker promised. That’s why due diligence is a thing. It was okay if he thought I was a ditzy, female loser who had just lucked out this one time. That’s what he was supposed to think. That was his job! I made the choice to let him think whatever he wanted to think of me. I stopped getting insulted. I stopped fighting back. I stepped into his role and understood.

After making all these choices, due diligence resumed, and I waited for the change. I approached Frank with more patience and understanding. I answered his constant questions even if I didn’t think they were important, ignored all his painful jabs, and held on to my courage. I kept my eyes on that view of the special world that I could barely glimpse through the door behind him. The stress still lingered like the aftertaste of a collagen shot (Seriously. Can’t they make those things taste better?), but everything went faster and more smoothly. There were fewer tears and hours-long therapy sessions with my business broker (Boy, that man deserves a medal). And on the last day, when Frank signed that big fat check and handed it over, I stepped through that door to the next journey.

I remember the moment I got the call to inform me the money had hit our bank account. My husband was driving, crossing over a wide river. The sun broke through the clouds as we hit the other side of the bridge, and my broker said, “Congratulations.”

I guess there was nothing wrong with my business.

JOURNAL PROMPT

This is a tough one. I want you to spot a Threshold Guardian in your life and write them down. They are not your enemy. You need empathy, courage, faith, and humility. Use your journal to explore how you could apply some choices in these categories to befriend, or at least move, your Threshold Guardian so you can get at what’s behind that door!

Do you have a story about your own Threshold Guardian? I’d love to hear it. Please comment!

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