Bet On Yourself, But Hedge Your Bets

Many first-time entrepreneurs dream of quitting unfulfilling jobs to start their own ventures. Over the years, I've learned the key isn't just taking the leap, but doing it with a strategic backup plan.
Bet On Yourself, But Hedge Your Bets

Prior to starting my first business I was working for a defense contractor as a software engineer.

I enjoyed my coworkers but the job was miserable and I quickly realized I couldn’t continue building military systems for the US Army in a windowless facility in Clifton, New Jersey for any length of time.

I knew absolutely nothing about business and, in those days, being an entrepreneur usually meant you sold weed, pills, or other “black market” goods.

Still, I was self-aware enough to realize that I would never be happy unless I forged a path forward on my own.

I hung around the W2 long enough to save up a little money to take a risk and jump into my first business venture, an all ages punk rock music club.

While we were successful, I quickly realized that I was one bad stage dive or fight away from being unemployed and out of business.

I needed to hedge my bets.

My roommate and best friend had started a very successful web design and development shop during college and, by this this point, he had a pretty healthy pipeline of clients and projects.

He also had been working 16 hour days for several years and was completely burned out.

At the end of our lease he decided to pick up and relocate to Los Angeles to chase his interests in film production. He made the tough decision to wind down his business where he was making almost $200,000/year for an $8/hour production assistant job.

He had saved up a healthy reserve but still needed some income while he transitioned into this new career.

I offered to “buy” his biggest and most steady client, a publicly traded sensor manufacturing company.

In those days, it was rare for any business to have an “IT department” and the “experts” were often young kids like us who had been experimenting and building fun, mostly useless projects on the web.

As a contractor, he helped them take their business from a paper catalog to online e-commerce.

I “purchased” this client via a 1 year revenue share agreement and while the details are cloudy two decades later, I’m fairly certain it was executed via handshake.

The work was straightforward and steady but it gave us both what we needed.

Within months his talent shined through and he quickly moved past being a PA and onto bigger and better paying things.

I was able to use this client to not only bring in some extra income and stability at a time it was very much appreciated, but as the backbone for launching my web development shop.

Sadly, I’ve largely lost touch with my old roommate and Measurement Specialties Inc was long ago acquired and absorbed into a much larger organization but I’m eternally grateful to both of them for the path it unlocked.

As for the punk club, my instincts unfortunately came to fruition. On January 10th, 2007 we were shut down permanently by the Fire Marshal.

This seemingly tragic blow was actually a blessing — by that time the building had fallen into serious disrepair and would require significantly more capital than I would be able to generate.

I realized that the business had run it’s course and I closed up shop.

It was sad to end that chapter of my life but, by this point, I had built up a healthy web development business of my own.

I had hedged my bets.

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