Friday, January 24, 2025

My Most Regretted Decision - Lessons Learned

My Most Regretted Decision - Lessons Learned

This is Episode 15 of the ongoing Lessons Learned series. For all the information, and an index of Lessons Learned episodes, go to the Lessons Learned Page

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Today's topic:  My Most Regretted Decision


We all have regrets. To be honest, we all regret that we didn't learn our hard lessons sooner. That's one of the advantages of reading books and blogs, and taking classes. If you can learn from others, you can skip a lot of mistakes.

When I started my IT consulting business (1995), two trends were in full force: 

1) The "Dot Com Bubble" was growing fast. You usually don't recognize a bubble when you're in it - especially if you're heavily invested.

2) The mad rush to get on the Internet. This was directly related to all that .com activity.

When people tell you that the rush to AI feels a lot like the .com bubble, it's true. People rushed to the Internet even though they had absolutely no idea what they were doing. It was irrational for most of them.

In my last real job (see the early episodes of this series), I worked in company that put information onto computer systems and sold that information to dial-up subscribers for a fee. We went through a long, complicated process to get connected to the government-funded Internet in 1993, before "anyone" could be on it.

In 1994, the Internet was opened to public and commercial use. Those who had a good reason to be on it (those with lots of data to share/sell) rushed in. Those who had no idea what it was jumped on the bandwagon.

I knew early on that I could make money connecting companies to the Internet. After all, a tiny fraction of one percent were connected. That left basically every company on earth who would be connected as soon as they could! Talk about a "blue ocean" strategy. Everyone on earth needed what I knew how to do. Sounds like a business plan!

Early on in my business (circa 1995), I made two big decisions. Sometimes you have to clearly define what you will NOT DO as well as who you will do.

First, I decided that I would not work free or cheap in exchange for ownership in other peoples' companies. The big deal at the time was to promise stock options in exchange for a piece of the pie when the big money hit. The trade magazines and emerging web sites were filled with stories of tiny companies making millions of dollars - and all their employees getting rich.

Instead, I got paid to sit at the table and have those discussions about buying and selling. And it was crystal clear that the early hard workers' share were being watered down again and again with every round of funding. You might have ten thousand mythical shares. But when the next round of funding comes, the total number of shares will go from one million to ten million. And your ten thousand will be a tiny piece of the eventual pie.

So I made my money in the C-suite and in selling labor to connect companies to the Internet - at full price. You want investors? Talk to someone else.

I think, overall, that was a great decision on my part. And I don't regret it.


What I DO regret is my second early decision:

Second, I decided that I was not going to be in the business of selling connectivity. I didn't want to selling telephone lines. I didn't want to sell Internet connections. I didn't want to sell the ever-emerging technologies of T-1, Fiber, and cable Internet.

Eventually, I did end up selling some telephony and connectivity. And I still get checks every month for the lines I sold. I just had a conversation with a woman I sold a telephone system to in 2011. She still pays here bill. And I still get a check for my commission every month.

We did eventually sell several phone systems and collects some good commissions. But I never went all-in and sold connectivity as a significant part of my business.

I regret that. I regret that I didn't jump in when a 56K line went for $3,000/month. Or $1,000/month. Or $150/month. 

I regret that we didn't build an entire business unit selling and supporting the phone and connectivity of our clients. We had many opportunities. And we dabbled it in. But we committed to it. And yet, after all these years, the Channel Partners conference (very telecom-focused) is the one annual conference I have attended more consistently than any other. Connectivity is literally everywhere and never stops evolving.

I was always doing something else, trying something else, and perfecting the already-profitable business we had. And, to be honest, my early bias held me back a little. I wish it had not.

All businesses have regrets. There's always the path not taken.

In the big picture, I can't complain about my journey. Making big early decisions - right or wrong - put me on the path to regular monthly maintenance and managed services. So it turned out just fine.

One of the best things about telephony and connectivity is the never-ending nature of the service. In the next episode, I tell how I learned about the beauty of perpetual contracts.

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