July 12, 2019

My Journey From F-16 Pilot To Successful SaaS Entrepreneur

Founder Stories
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For five years, I had the amazing experience of living my childhood dream. As a mission qualified F-16 pilot for the U.S. Air Force, I logged nearly 1,000 hours of flight time as wing man, flight lead, mission commander and instructor.

In 2007, a slipped disc in my lower back forced me to take a break from flying. I had surgery and waited for my back to heal so I could return to the job I loved. Then I reinjured the same disc, and two surgeons gave me the same opinion: a second surgery would be more likely to put me in a wheelchair than back in the cockpit. Just like that, the whole trajectory of my life changed. My childhood dream was crushed.

And I had no idea what I was going to do next.

After spending a total of 14 months in medical limbo — meaning I couldn’t fly but also couldn’t work for anyone else — I was medically retired from the Air Force. But that in-between period turned out to be an opportunity, because I turned to my laptop and tried to figure out how I could make money online.

I knew I didn’t want a regular 9-to-5 job. I also knew I wanted to control my own income — that is, I wanted to take calculated risks and receive calculated rewards, with no ceiling on how much revenue I could earn.

Even though I had no business experience, I started dabbling in online and affiliate marketing and trying to solve problems in that space. By the end of my medical leave, I’d started making money and felt confident that I could generate a sustainable income. Within a year or two my goal had become more specific: I wanted to start an online business that could help other small businesses.

When I first crossed paths with Zach Anderson in 2012, I had already started two SaaS businesses: Localizer Leads Tool, which helped digital agencies generate leads, and Web Weaver Elite, which built and hosted websites for small businesses.

Zach owned a digital agency. He had an idea for a reputation marketing platform and developed it under his agency. He then invited me to help launch and grow the platform. We launched Reputation Loop in February 2014 and sold more than 250 units — giving us a Monthly Recurring Revenue of about $25k — within the first 10 days. 

Five years later, after bootstrapping our way to a market-leading position within our vertical, we sold the business to ASG. Zach and I had laid out our exit strategy early on and so when the right buyer surfaced, it was easy to say yes. Not only did the deal meet our financial requirements for a 100 percent equity buyout, but we were confident that ASG would take great care of our customers.

Looking back on the surprising arc of my life thus far, I can see that my Air Force experience prepared me in specific ways for my second career as a SaaS entrepreneur. One thing I learned in the Air Force was not to get emotionally attached to a particular approach or outcome. In a SaaS context, this means I have a strong emotional commitment to my customers, but I’m not attached to a specific product or feature. If something isn’t working, I change it and move on to solving the next problem.

Another thing I developed as a military pilot was an obsessive focus on processes and procedures. In the Air Force, we would set our watches to the second each morning. That attention to detail — in an environment where sloppy execution could be fatal — set me up to be fanatically focused on delivering value to Reputation Loop’s customers. Zach had a similar mindset, and building strong processes allowed us to grow our business with minimal staff.

My advice to SaaS founders who are trying to bootstrap their way to a successful exit begins with those two items and includes a few other things I learned in my second career.

  1. Don’t get emotionally attached to products or features.
  2. Put detailed processes in place from the very beginning and refine them as you go along. Otherwise, you’ll waste time and make mistakes by doing things on an ad hoc basis.
  3. Know what you want and what you’re willing to accept for your exit.
  4. Create a workspace that gives you some physical separation between your work and the rest of your life. If you can’t do this, you’ll never be productive at work and you’ll never be present at home.
  5. Choose your business partner carefully — that relationship is like a marriage. (Zach and I had life insurance on each other.)
  6. Roll with the punches. You’ll have some days that are huge, but don’t expect everything to be peaches and roses all the time.
  7. Bringing in customers is great, but then you have to support them.
  8. As a bootstrapped founder, you’re wearing multiple hats. Know when to hire people to take over those various roles.
  9. A lot of people will tell you what to do based on their perceptions and needs. You know your business better than anyone else. Pay attention, but take advice with a grain of salt and weigh it against your end goal.

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