Salesmen rarely make good managers or business owners. But that doesn’t stop them from trying.

It used to be a hallmark of American business that successful salesmen were promoted. The logic is obvious. Whatever makes Joe or Amy great at selling the company wares should be emulated by others, thereby making the company more successful.

But selling and managing require very different skills, much like playing a sport and coaching are different.

Sometimes good salesmen, people with great interpersonal skills who grasp what’s important to other parties in conversation, can successfully transition to running a business. But more often than not, they lack the attention to detail and ability to switch between focusing on the big picture and mastering the nuances of daily operations to succeed.

In the end, everyone is frustrated, and the company hasn’t prospered as expected.

The same thing happens in our personal lives. We achieve success in one area, and assume that it’ll happen in other areas. For too many people, myself included, the result is frustration. In my case, I get the added bonus of losing money.

I started my Wall Street career trading bonds. I know the interest rate market inside and out. I can discuss Liquid Yield Option Notes (LYONs), inverse floaters, and repurchase option agreements, and I know the ins and outs of collateralized debt obligations (CDOs) as well as derivatives on debt. I understood the financial crisis at a level that made me sick.

I’ve also spent many years investing in equities and options, and I use a proven strategy to run my Triple Play service. All of this makes me well educated in the world of finance.

None of this makes me an astute investor of early-stage businesses. But that doesn’t stop me from trying.

My History in Angel Investing

The siren song of 1,000% gains lures me in. And I’m swayed by the idea of bypassing all the noise on Wall Street. So from time to time, I open my checkbook and break one of my investing rules. I get involved in something that’s not my expertise. The outcome is predictable.