Information Technology Dark Side

Struggles of a Self-Taught Coder

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How to sink your lean bootstrap #2: Chasing Dante’s Banner

February 6th, 2012 · 1 Comment

Just to Recap…
Bootstrapped startups are a version of the lean startup with a 37-signals-esque twist, i.e a lean bootstrap. The goal of a lean bootstrap is to run in the black as early as possible, preferably from day 1. Boostrappers don’t need or want outside capital for the most part, and they are always conscious of the need to validate that they can actually make money doing whatever they are doing.

Basically, if you (metaphorically) placed Rework and The Lean Startup in a blender, turned it to high, then ran the puree through a mumbo-jumbo filter (basically the last 1/3 of The Lean Startup would get removed), the remaining juice would be called “The Lean Bootstrap”.

Dante’s Banner
In Dante’s version of hell, the souls of the uncommitted reside somewhere between heaven and hell where they are condemned to chase a banner blown around by the wind, never catching it, forever pursued by a mob of angry hornets.


Dante’s Banner for the Lean Bootstrap
In the lean bootstrap’s version of hell, the soul of the entrepreneur resides somewhere between success and fail where they are condemned to chase a hundred dollar bill blown around on by the wind, never catching it, forever pursued by a mob of demanding users.

Don’t Start a Lean Bootstrap Just to Get Rich Quick
Early on in TroopTrack’s history my partners and I had impossibly naive expectations about growth and profitability. I honestly believed all three of us would be working on TroopTrack full-time within a year of launching. The market was RIPE for a superior product to sweep in and steal a ton of market share before the competition could respond. So we set up an agressive timeline – we would launch a beta product within six months, then sit back and watch the money roll in.

Because we knew we were just a year away from being rich, we worked on TroopTrack in an unsustainable way. We got worn and burned out, stress started to pile up, and we began to have the disagreements typical of people who have sacrificed emotional, physical, and mental health for a “greater good.”

Our launch was a big thud. Our product was buggy and unstable. We didn’t have good ways of keeping track of customer feedback or monitoring exceptions as they occurred within our code. We didn’t know how bad our product was!

During this time, my desperation to generate revenue and prove that we had a “good” product took me down a thorny path. I started chasing deals with sponsoring organizations of multiple troops and tried signing them up en masse at a steep discount. The fact that I was occasionally successful at generating interest and once even closed a deal only made this inclination worse. I chased deals with churches, scouting districts, and charities with programs that are similar to scouting. I even considered a massive pivot to re-tool TroopTrack to support the Air National Guard!

The toll of this constant churning plus the feeble response of the market place was too much for our partnership – roughly eighteen months into it we dissolved and went our separate ways.

Start a Lean Bootstrap to Solve a Problem that You Care About
It took some soul searching and a certain degree of stubbornness, but I didn’t give up on the TroopTrack product after the original founders split up. It’s been years since then, and time has given me a certain amount of perspective about why I continued on alone. I think there is a lesson to be learned from my experience and the differences between why I was involved in TroopTrack and why my partners were.

In hindsight, I think the critical factor was the source of my interest in TroopTrack. It was based on my involvement in Scouting as an adult. I was frustrated by the products that were available – they were total crap and I needed something better. My partners, on the other hand, were recruited (by me) and persuaded to join based on the MARKET POTENTIAL of a superior product. They didn’t have any real experience in scouting but could see what a windfall capturing a corner of the scouting market would be financially.

In other words, I finally realized that I persevere with TroopTrack because, among other things, I am trying to solve a problem I really care about.

Love It or Leave It
Years later, I wish I had approached my partnership in a different way. Nothing against my former partners – they are both fine people and good programmers. But if I could do it all over again I would pick someone else. I think it’s fair to say that if THEY could do it all over again… they wouldn’t.

I believe now that I would have been better off picking a business partner who was motivated by a love of scouting and was also frustrated by the quality of products available to scouters. Even a non-technical partner of this sort would have been a better choice in the long run. Their insight into the way scouters perceived TroopTrack would have been much more meaningful than the acceleration gained by recruiting additional development talent.

I think I also would have been better off if I had just had a different attitude about TroopTrack in the early days. I convinced myself that it was an easy way to get rich doing something I cared about because I didn’t realize that just caring about something is enough justification. There doesn’t have to be an obvious path to wealth to make something worth pursuing. If you’re going to trudge the long road of a lean bootstrap, you better get on that path because you care about solving a problem, not because you want to get rich.

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