Humble Beginnings to Big Exit
Lessons From Building and Selling an 8-Figure Business
The fever dream of an ambitious child
As a kid, did you want to be a firefighter or Superman or Barbie when you grow up? Like, were you normal?
I, on the other hand, wanted to be a motivational speaker.. or a businessman.. or maybe a cult leader.
Yes, I was little different.
The problem with the motivational speaker gig, I realized, was that I needed some credibility. How do you get on stage without having anything to say?
So, I decided to start with business.
It was a long, winding road full of ill-advised attempts before landing on the business that finally paid off. I tried freelance web design, graphic design, soap distributorships, an e-commerce jewelry shop, a life insurance business, importing scooters, a film school partnership, and even a lemonade stand as a kid. But, none of it clicked—until one day, after being laid off from a crummy ad agency job, my real opportunity stared me in the face.
That's when I launched Widerfunnel.
And my experience over 15 years of growing the business to exit has taught me an important insight:
Much of the popular advice about entrepreneurship is wrong. Seriously wrong.
I was tempted to buy into the idea that only unicorn businesses matter—that if you're not running a billion-dollar company, you should be embarrassed. The Peter Thiels of the world are out there telling you that lifestyle businesses are for the weak. That belief is harmful.
For years, I questioned whether my company was "good enough." I told people Widerfunnel was my “starter business,” where I’d cut my teeth before launching something "real."
Then, during a lunch with my former customer and friend, Jeff Booth, I got a reality check. I was rambling about how I’d build a “real business” someday. Jeff stopped me and asked, “What about the business you already have?” He pointed out that I had created a profitable company with high margins, no investors, a great leadership team, and plenty of growth potential. It was a business I could maybe sell one day.
That conversation changed my perspective. From then on, I focused on turning Widerfunnel into the best company it could be—and one that was sellable. Ten years later, I sold the company for over 8 figures in cash, which now gives me the freedom to choose where I invest my time. Not only that, but the company is still one of the best quality agencies acquired by its new owners.
Since selling the company, I’ve been on a 3-year-long journey to re-evaluate my priorities and discover where I can make the greatest contribution in the world.
I discovered that I want to share what I learned from 15 years of building a company out of nothing; one that helped me reach financial independence by the age of 45. I’ve discovered counter-intuitive insights that could help you and I’m not afraid to have a strong opinion.
On the other hand, the business has also taught me humility.
I know that I know far less than I used to think I know. The challenge I face continuously is to find out which of my beliefs are true and what works to get the best outcomes.
That awareness extends to this new writing project. Any insight I share may not be true for you, or anyone else. I only know my experience and what I’ve seen work.
One thing I’ve seen clearly is there’s a huge problem in what I’ll call the “motivational entrepreneurship” industry.
So many content creators present their opinions as if it’s the only way to see the world. Hell, I’ll admit to doing much the same thing in my first book, You Should Test That!, which I think was partly driven by the fact that the book was a promotional piece for Widerfunnel’s services. I believed I had to present an over-confident perspective to gain trust. No one buys from an agency that’s unsure of itself, right?
That’s partly why I was always skeptical of business books and talks. Everyone is selling something. That’s why I’ve never paid to go to a conference that I wasn’t speaking at, because I knew they were all sales pitches.
But today, I have nothing to sell you.
I have no financial interest in the outcome of this writing (so far, at least.) And I don’t even care much about building a big personal brand. Sure, I want to earn your respect, but I don’t get a lot of validation from external opinions. Since reflecting on selling my company, my perspective has shifted to asking myself what I can do to be of service to others and enjoy the rest of this short life. More than anything now, I want to be a contribution to others.
I will still have strong opinions, especially when I see blatant injustice and egos running amok. More than ever, I will call out bullshit when I see it.
And I’ll still sometimes be wrong. I advise you to take my opinions just like those of anyone: with a grain of salt, because they reflect my admittedly narrow experiences. On the other hand, you can also trust that I have nothing to sell you from this and I will tell you the unvarnished truth as I see it.
I’m going to start this series with a few months of topics and see where we go from there. If you think something is interesting, helpful, or downright stupid, feel free to add a comment. The more interest there is, the more time I’ll commit to sharing more insights.
I’ll also add a caveat that there’s little I say or write that are original thoughts. There is nothing new under the sun. The best artists steal and I consider myself a collector and curator of the best perspectives I can find. So, if it seems like I’ve adopted others’ ideas as my own, that’s because I have, proudly. Usually, I don’t even recall where they were absorbed from. So, if you see an idea that looks like someone else’s and I haven’t given them credit, feel free to ask me about it and I’ll happily credit the originator.
Thanks for reading this far and I hope to see you around on the next topics. Oh, and please add your email address below to get the latest article in your inbox before anyone else.
Thanks for reading!
