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The Dot-Com Bubble Burst: Lessons from My First Business Sale

Back in the heady days of the dot-com boom, I was just 21 years old, a wide-eyed entrepreneur ready to make my mark with my very first company. The digital age was dawning, and the buzz around websites and e-commerce was electric. We were inexperienced, but that didn’t matter much because enthusiasm and eager prospects were in abundant supply.

My journey began with a burst of excitement and a rapid learning curve. We were in the business of providing white-glove service in a world where such attention to detail was both rare and revered. However, when it came time to sell, my lack of experience showed. I entered into an earn-out agreement that seemed promising but quickly turned sour. I found myself trying to meet impossible metrics without any control over my team or costs, and my part of the earn out was tied to the performance of the acquiring company, which operated on a completely different business model centered around ticket submissions, clashing with our hands-on approach.

Fast forward 18 months into what was supposed to be a 36-month compensation agreement, and I walked away. I took a financial hit on the earn-out just to get out of what had become a nearly terrible situation. Yet, despite the challenges, this experience was far from a failure. It taught me invaluable lessons about the importance of understanding business metrics and building relationships in ways I had never considered before.

These lessons became particularly poignant after I read the book Built to Sell. It revolutionized the way I thought about business, teaching me to streamline operations and focus on what could be systematized and scaled. This book was a game changer, turning my painful first sale into a stepping stone that paved the way for the successful sale of my second company, which was straightforward and left both parties satisfied.

This transformation also led me to become a Value Builder Advisor, driven by a desire to help other entrepreneurs navigate the tricky waters of business growth and sale. My mission became to ensure that others wouldn’t have to learn things the hard way, as I did. Now, I use the tools and strategies I’ve learned to help business owners maximize their company’s value without settling for less.

The journey from that first tumultuous sale to now has not only shaped my career but also my approach to business. It’s a testament to the power of resilience, the importance of continual learning, and the value of turning even the most challenging experiences into opportunities for growth.


If you ever feel like your business journey is taking a dive, remember that each setback is just setting the stage for a bigger comeback. Keep learning, keep evolving, and most importantly, keep sailing—even when the waters get rough!

Bill Dotson

Bill Dotson

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