The best job I ever had

The best job I ever had is hard to explain in a nutshell. I’ll try, though.

A good friend and I tried to startup a company around a big idea we had. We convinced a friend of ours who had a successful, growing company to hire me and pay me a decent salary (I’ll disclose: it was 50k a year with benefits) to work 50% of my time on a special project for his company. The other 50% of my time, well, that was free for us to work on the startup. In consideration for that 50% “free time”, among other things, we considered it an early angel investment in our startup and wrote up some quick terms.

I loved this job. And it led me to create a very successful company, but not the one you’re thinking.

Jetsetting by seebq on Flickr. 2007!

So let me ask you something first, a test, if you will. Which project has a greater chance of success?

Project 1: Unlimited budget. Unlimited scope. Unlimited time, at least a year or more. Big market. Stakeholders give free reign.

Project 2: Extremely limited budget. Very limited scope. Very specific timeline (3 months). Small amount of customers, in the same building. Stakeholders, too and highly involved: critical and skeptical.

Which one is more successful?

Project 2, hands down. Every time.

Project 1 was the startup. Suddenly, we had unlimited time to figure out an even bigger idea for an even bigger problem to solve in our early startup stage. We had salary for me (unlimited runway)! And lots of time now! So the project expanded. With no customers, we could engage in all sorts of “customer discovery” and fun stuff to setup things The Right Way. Lots of setup. Lots of discussion. I even met with a banker to make sure it was the “right relationship.” This startup failed, for a number of reasons (big idea, too soon), but my main theory I realized later was that it lacked constraints and other factors that constraints breed.

Project 2 was the special project for the company. The need was very specific: a team of 20 field service agents, with a specific budget for the technology to enable them to do their job better: faster, quicker, more efficient. Had to be done in 3 months for the initial roll out, since that was the pilot they had sold (and I had to get back to the startup, of course). The customers were so close, in fact, my office was right outside the warehouse door, where the pallets came in for the first part of the problem we were solving. I even moved my laptop and did some of my best work with it sitting on top of the pallet, turning the screen around to the main users (customers) after watching them fumble through it, and saying to myself: “I’ll have to change that, and that.” And then coding up a change while standing there (my first standing desk), and grabbing the users again, with my laptop still on the pallet, and us both saying: “OK, try again now. Aha, much better!”

I should add that because the stakeholders of the special project were critical and highly involved. The COO was the one who hired us and made the deal, and his CEO was super skeptical that the whole thing wouldn’t work and made for some awkward initial encounters — now we’re great friends. The limitations and skeptical nature led the project (and me) to consistently prove that I was creating value. And in my head, the sooner I created this super valuable thing, the sooner I could get back to the startup. A funny thing happened, in that I got super excited about the special project, and found myself working on it, more than the 50% allotted for the startup. And learned a ton. Not just on the project, but to be fair, our investor wanted both to succeed, so I learned a ton about forming (and running) a successful company.

Project 2 was wildly successful. That company went on to be sold for lots of money, in part due to the unique software and technology we built together.

The startup (Project 1) with unlimited runway failed. But, after realizing that constraints make for better software, I started a software company that took that ethos to heart: constraints make better software. That company still exists today, and the formation stories of how Big Nerd Ranch builds great software (and teaches others to do it) is for another time.

I wish there was yet another company that existed today that would help entrepreneurial minded startup founders connect with businesses that need software, and in exchange for hiring them on to work on projects (for 50% time), they get equity and the chance to start something up. A win-win situation.

If you’re interested in this from either side (a startup or a company that wants to hire an entrepreneurial person), write me. I’m always looking for customers to solve problems with real constraints.

Charles Brian Quinn
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