I regret that I haven’t kept a record of my progress (or regress as it has been at times) in my journey to finally launch a successful online business.

They say that “The best time to plant a tree was 20 years ago. The second best time is now.” And so I begin now.

I am an entrepreneur at heart, but my path to success has so many twists and turns it’s embarrasing.

Over 20 years ago, a writer for a small business news magazine interviewed me when I was at the height of my success as the owner of Akron-Canton Connection (a phone company of sorts). After I explained my entrepreneurial journey up to that point, he decided to title his story “The Accidental Entrepreneur”.

At time I was honored to have my photograph on the cover of the magazine, but as I have reflected back upon this incident over the ensuing years I have tended to focus more on that title than the fact that I was the feature story.

The title implies that that my rise to success was not only entirely unplanned, but achieved without any effort. While the former may be true, the latter certainly was not. I think I can say without hesitation that I have always put enormous amounts of effort into the many and varied business ventures that I have delved into, but unfortunately 99.9% of that effort has been for nought — at least in a financial sense.

While have had a couple of semi-successes over the years, I’ve largely been quite unsuccessful. And now at age 69, most people would say it’s too late. Nevertheless, I have not — and can not — give up my quest to achieve the elusive “American Dream”.

I say I “can not” partly because of an unquenchable desire to succeed, but also out of necessity. I have reached at a point in my life where I am growing poorer faster than I’m growing older which is somewhat frightening. And I have my dear wife to think about as well!

My perspective of “old” people has continually changed over the years. I used to assume that by age 50 you would have gained about all the wisdom you’d ever need, would have solidified your opinions and view of life, and stopped worrying about what other people thought of you.

By age 60, I presumed you would be less concerned with achieving success and more concerned with what you’re going to do when you retire, (and, frankly, also begin the slow descent into dementia).

By age 70, you should be financially secure and spend most of your time reminiscing about the good old days with your retired buddies and enjoying time with your grandchildren. I also assumed that by then you wouldn’t have the same cravings and desires of your youth (such as need for acceptance or the desire for sex).

Well, I’m almost there, and nothing has turned out like I expected — and frankly it’s a little scary. The good news is that I’m pretty sure my mind is almost as sharp as it was in 30’s and 40’s (although I guess my mind could also be tricking me into thinking that). My physical health is also pretty good except for the 30 lbs I’ve added since I was 30 years old.

But the bad news is that I’m not ready to be old from a financial perspective — not even close. Sometimes I feel like we’re heading for a train wreck. Oh, we’re good at faking prosperity and pretending we have our act together. We even try to fool ourselves, but deep down we know it can’t last. There’s this fear of being discovered or uncovered — like being caught naked — and having to admit how desperate and out of control our lives really are.

Okay so I’m being a little overly dramatic.

During those rare times when I had a regular job with a good company, I was good at saving money. But when I’ve worked for myself (which is most of life), I’ve felt that the real key to success and wealth is to invest money into myself and the right business model. Unfortunately, that hasn’t paid off.

I would say that after about age 40, I pretty much gave up (or ignored) the notion that I could generate wealth through saving and investing in things like stocks and bonds. Instead I became convinced that the best (and only) way I could achieve financial independence is by creating my own wealth through entrepreneurship.

Unfortunately, that’s much easier said than done. And in my case, it’s further complicated by the fact that I seem to have this incurable desire to invent my own way of doing things. I’m eminently unteachable and insist on turning everything into something totally unique and stamped with my personal touch.

So, instead of doing something sensible like purchasing an existing business or following a proven business model, I have to create something totally new and unique, and often end trying to solve problems that don’t even exist.

That’s how I ended up starting the phone business. That worked out pretty well for a while — but I failed to turn it into something that was sustainable for more than a dozen years.

Oh I have tried a couple businesses that had fairly solid business models – like opening a shipping & copy store, investing in a call center, and distributing candy, pepper spray, and discount insurance cards (not all at the same time lol), and could have succeeded at those, but I had other issues including lack of confidence and interest.

I have long had a very strong interest in computers and software (including programming or “coding” as they say now) so I have kept coming back that. And of course, we’ve had the internet for 25+ years now which has been a blessing and a curse — both because there are so/too many opportunities.

I don’t have time or room to list all of the things I’ve tried that involved computers, software, and the Internet, but one theme that’s I’ve come back to over and over is “digital marketing” for small “brick & mortar” business (there was a time when it was known as “online marketing for offline businesses”).

A person or business that helps small businesses in this way is called a digital marketing agency.

I love the idea of helping business owners market their businesses on the Internet, but there’s one big problem with this model — it typically means that you’re spending a lot of time with each client — building their website, setting up sales funnels, posting content for them, managing their social media and advertising, etc.

This business model is very difficult to scale and it’s often more like a job instead of business. I don’t like that, and I’ve liked it less and less as I’ve grown older and reached the so-called “retirement age”. My goal now, more than ever, is to have a business that makes money round the clock regardless of what I’m doing or where I am.

But that’s a tall order to fill. At the very least you’ll typically find yourself working like crazy before you eventually reach a point where you’re business can run that well.

I have investigated and tried many things in an effort to find such a business model. And as I mentioned, the need for a business that doesn’t consume too much time has become more and more important as I’ve aged. This is partly because I would like to act like I’m retired even though I’m not. And I’m concerned about my ability to put in long hours as well.

Although I’ve been fortunate to still have the ability to work pretty hard, I know it won’t last. At my age, I can’t realistically expect to be very productive more than another 10 years tops. So the pressure to find something that will work in my situation has continued to intensify over the past several years.

I have to thank my wife here because she has shared some of my same frustrations, and has every right to be frustrated with me over my many failed attempts to get something off the ground. I’ve been promising success for our entire 12 years of marriage and have virtually nothing to show for it. Thankfully she’s been extremely patient and still believes in our ultimate success.

Having said all that, I think I’m finally ready to talk more specifically about the business model I am currently pursuing. I’ll discuss that in some detail in my next post.

PS: The photo is me with my wife, Susan.

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