I guess it took some degree of courage on my part to take the leap and leave my steady 6-figured salaried job with health benefits to start my own marketing agency business back in January of 2006.

Back then, My Space was the social media platform of choice, Facebook didn’t exist yet (it would launch in September of that year) and Google was only 8 years old, and YouTube was barely a year old.  LinkedIn was only four. 

I had been dabbling with HTML since the late 90’s and as a side-hustle, I had built an online pet store called Lucy the Wonder Dog (named after my dog) on the Yahoo! Shopping ecommerce platform.

My side hustle — an ecommerce pet store

After commuting back and forth into New York City as the VP of Production for West Glen Communications, a video-public relations company (now defunct) I still had a full evening of work ahead of me.  I would pack orders when I got home to ship out the next day and visited a warehouse where I stored products on the weekend.  I was also a father of an 8-year-old boy, a home owner with a mortgage and husband to a wife who also worked fulltime.   

While exhausting, I found entrepreneurship very fulfilling.   I enjoyed using my skills and experience to practice online marketing for my own business, creating landing pages, building an email marketing list of over 10,000 names, and practicing early SEO.   Within a couple of years I decided to pivot from selling pet supplies with thin profit margins to selling services like email marketing and website development for much higher margins.

With the support of my wife and having the good fortune to be covered by her health plan, I took the plunge and resigned my job to devote myself full time to my new venture — Samson Media, named after my son.  The mission — online marketing and all its various permutations, some, which hadn’t even been invented yet, such as location-based marketing, smart phones, mobile websites and online videos.

The first Samson Media website in 2006.

Did it take courage to quit my job and take the plunge into the uncertainty of starting and building a business?  I think it did.   I was scared stiff. 

Unlike many entrepreneurs who start a business out of financial necessity, my reasons had more to do with lifestyle (no more commuting) and my genuine interest and fascination with harnessing the power of this global phenomenon known as “The Internet.”

But walking away from a high-paying management job that I actually enjoyed a lot, with a nice office, title, 20+ year reputation, while basically starting over from zero, was a calculated risk that I could only hope would succeed.

Fast forward to 2021.

I had grown Samson Media into a profitable enterprise that checked all the boxes for me:  complete autonomy, creative problem solving, growing profitability, an ongoing client base, word of mouth referrals, working from my home office (I was Zooming before many people reading this had even heard of Zoom) and working with a dedicated group of website developers, social media marketers, writers and graphic designers.  I never thought of selling my business until it came up as a topic at a peer networking group I belonged to.

At a particular meeting, one thing led to another and I was eventually introduced to a business broker who specialized in selling digital agencies like mine.

After some exploratory calls with the broker and parsing my financials, I was pleasantly amazed at how much my business —- a virtual company with no real estate, patents, or proprietary services — was worth.

But could I part with my baby, my company, that grew from nothing more than a concept and idea in my head to a business serving over 20 clients that supported my family and gave me the freedom to live my life on my terms?

In a word:  yes.

Did that take courage?  

Some.

More than just getting a large payout I worried about what I would do with myself.   I also worried about my clients as well as the people that worked for me and their futures.

In my case (and every situation will be different) I was able to negotiate an ongoing deal with the buyer to continue working for Samon Media, focusing on new business and client relations.   All the folks who worked for me retained their jobs and all the clients stayed on.

Yes, change is hard.   And scary.  But trusting my gut and consulting with my wife, colleagues, and friends whose opinions I trusted, helped me tip the scales in favor of selling at a time when I was weighing the pros and cons while wanting to move on and work less.  The money also definitely helped when it quickly became clear that there was a huge demand for buying profitable agencies like mine. 

I now firmly believe that businesses are meant to be created and sold like a horse breeder selling a prized stallion.  You raise it, tend it, guide it, and maybe even love it.  And then send it on its way and wish it well. 

In many ways, I gave my business an entirely new life!