I was brought on to the other company as a CTO, they where a profitable startup but had used contractors and had a bad tech stack due to no internal technical direction. I entered her company as a consultant and interim CTO. While I did do hands on development work, I had a track record of rescuing companies with good business models, but where hampered by their technology and technical debt.

Her entire company was running on a legacy system that the vendor who was a small custom software shop, had abandoned and who was not interested in selling the source code to anyone (think Computer Associates on a small scale), The owner had done well and was just bleeding the contracts he had until they ran out. While he sailed around the world.

So she was locked into a system that had no path to add features. I had to reverse engineer this system to get to the data, get it out of the underlining datastore it was using and into a proper DBMS, as well as architect a solution to synchronize data between the two while we implemented critical features they needed in a new system, while strangling out functionality of the old system. Then hire pretty mush an entire development team from the ground up to do this (fortunately I knew a few developers that had just lost their job due to their company selling). She was looking to sell her company at top dollar and this system was costing her opportunity on that front.

So while I was doing development, I was not just a engineer I was 27 years old, I was in charge of and navigating the technical direction of a multi-million dollar company.

The reality was the other company was an exit north of $50 million dollars. I got a check for $125k and told to have a nice life. Because I did not negotiate an exit package in the event of a sale. I believed the VC's when they said this was a long haul venture, they where not looking to take it public and where not looking to exit. They where not silicon valley VC's and had more of a background in large real estate deals. So most of their ventures where long hold investments. There is a lot more to that story. 911 happened and hit the industry it was in hard and I think they changed that viewpoint at that time, but I did not shield myself from that reality.

The point is, the sale would have never happened had I not joined the company. Had I extracted my real worth I would have walked out of that exit with about 2 million dollars. Like the COO and the VP of Sales did. She saw all of that happen and she knew the reason I did not and it was because even though I was doing well, I still thought like a poor person.

The bottom line is that neither company would have sold for the sticker prices that they did, had I not entered those companies and navigated them out of their bad technical direction. There are certainly other people that could have done it, but I had a proven track record of doing it. I was a sure bet, thinking like a poor man made me price myself on the market by what my hands can do in an hour and not see myself as a product, a product that reduces risk and risk reduction has value.

To get deeper into the story, this company was involved in hotel allotments and was a central hub for them. Think of something akin to a commodities market for hotel rooms. One of the things that they really needed to be able to do was provide their allotments in real time to online vendors, something that they could not do. So they where basically packaging up an ETL every day and sending it to them. Within a month of me being with the company we had the data sync up and running and had web services on top of the new DB to provide real-time allotment. We brought Travelocity and Expedia online first and our revenues skyrocketed. When I signed on with the company she made me an offer that I could get a take of every booking that was done thru the web services we where going to build, if I could get this system up and running, but that would be my compensation. No base salary, just a take of every booking. I declined because I was risk adverse and wanted to hold on to what I had. She said this was the moment she knew that I was holding myself back.

Think of it this way, imagine that I came up with an algorithm that could predict the next lottery numbers. I was calculating my labor of how long it took to create the algorithm as it's value and not the fact that it could net millions in winnings. If I had that magical algorithm I could certainly sell it for 50% of the next purse. I was selling it for the man hours I put into making it and when she said, hey I will buy the ticket and give you a cut, I was like no, I want money now and that is how a poor person thinks.

You are right, I was making great money for my age and the era but even with all that and even though I was doing great my earning potential was being hampered by the the way I thought.

Finally I will leave you with this. I grew up not far from Palm Beach. Many places have the other side of the tracks we have the other side of the bridge. I had very rich friends in High School and I remember they would take me to dinner with their family at really nice restaurants. I remember being at those dinners and thinking one day, I swear I am going to earn enough to take my grandparents to dinners like this because it was so nice. No one having to serve, everybody just getting to sit there and talk and enjoy each others company. That was literally my only goal of wealth in life and that is how a poor person thinks. That was the good life to me, going to a restaurant. That was my measure of made it.