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- The Unexpected Story of How I Ended Up Selling a Business to Mark Cuban
The Unexpected Story of How I Ended Up Selling a Business to Mark Cuban
It sure wasn't what we had planned!

As you know, what we love to do in this newsletter is share the little-known story of an entrepreneur’s breakthrough - that moment everything changed, when they figured something out. Sometimes famous, but not always, these entrepreneurs have stories that surprise and - hopefully! - entertain and inspire.
Well, I’ve been asked about this story enough times that I finally decided I should share it here. Enjoy!
(This was my first “One Person Empire” but not my last. If creating your own - with my help - is of interest, I am launching my 4-week One Person Empire cohort again next week. It won’t be offered again until maybe sometime next year. I invite you to check it out.)
People often want to know how I ended up selling a business to Mark Cuban. Well, it wasn't planned, that's for sure.
About a decade ago, a large Fortune 500 company came to me and essentially said, "Hey Steve, we think our next big market is the self-employed - the freelancer - and we think that you can help us get in front of them. Do you have any ideas?"
I didn't, but I would!
After some brainstorming together, I suggested we create a website just for that market. There were tons of "small business" websites at the time - heck, I created content for many of them - but none specifically for the self-employed.
In fact, "TheSelfEmployed.com" seemed like a perfect name. Only problem was that URL was owned by a band in Norway of the same name.
We bought it from them. Problem solved.
Onward
Then my trusty tech sidekick Abby and I got to work. I had the content, she has the mad tech skills, my Fortune 500 partner had the budget, and together we created a fantastic site.
So much so, that before long, we attracted great sponsors like Microsoft, Staples, FedEx, SCORE, and many others.
We ran that site for several years and it became a content hub for all things self-employed. So much so, that many of the articles became super valuable because of their SEO longevity.
We never really had an exit plan, we were all just happy to have a successful, valuable site with content that people really seemed to like.
And that's where Mark Cuban comes in.
Enter Mark Cuban
He is the part-owner of a small business hub called Zen Business; an impressive, robust site. Well, they wanted to capture more of the small business market and he knew that owning legacy SEO small business articles was a good way to jump to the front of the line, content marketing being such a great way to get attention and all.
So, one day, I got an email proposing a sale of my site and all of its content. The offer was fair, but being my wont as an ex-lawyer, I negotiated. Natch!
In the end, we agreed, I sold the site, everyone was happy, and I have a great story to tell!
The Takeaway
And there’s a lesson here too: We followed the market, saw a gap, and created something useful. The audience came, the sponsors came, and eventually, a buyer came too. We hadn’t planned the exit, but we had built something worth buying, and fortunately, someone did.
Steal This Strategy
🛠️ Tool - My One Person Empire Accelerator: If I did it (and two other times) you can too. Work with me directly and let’s build your idea or business together.
📖 Book - How to Win at the Sport of Business. Learn it from the master, Mark himself.
🌐 Website - Mark Cuban’s Best Shark Tank Deals. Wow!
About Steve
Steve Strauss is the best-selling author of The Small Business Bible (and 17 other books), Inc.’s small business columnist, a lawyer and entrepreneur. He sold his last venture, TheSelfEmployed.com to Mark Cuban & Zen Business. Contact Steve!
“Be bold! For boldness has genius, magic, and power in it.”
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