Craig Vodnik: Wise Words from Chicago’s Bootstrapping Guru

Casey Gordon | June 9, 2016

Sometimes nuclear engineering just isn’t cool enough.

Craig Vodnik is unique among entrepreneurs, and it’s not because he has both a bachelor’s and a master’s degree in a subject that to many may as well be science fiction. Nor is it for his expansive record collection, which includes everything from Man on the Moon: The Flight of Apollo 11 to Milli Vanilli’s Girl You Know It’s True.

So what is it then? Craig co-founded and bootstrapped a company to profitability in a measly two years. That company is cleverbridge, a full-service billing solutions platform for software and subscription businesses.

Back when it first turned a profit in 2007, Craig was the only employee in America (his three co-founders were all former colleagues headquartered in Cologne, Germany). Today, cleverbridge boasts offices in Chicago, San Francisco, Cologne, and Tokyo. Craig’s Chicago team is over 100 strong.

For Craig, bootstrapping is a way of life.

Take for example the impressive 1965 Grundig KS620 stereo console in his office. When you co-found a company that enjoys a casual half billion in annual global sales, you can probably afford a state-of-the-art sound system for your workspace, but where’s the fun in that? Craig found this rundown Grundig on craigslist* and craftily refurbished it.

And somehow, Craig still finds plenty of time to be a champion for the next generation of bootstrappers and entrepreneurs. He mentors at 1871, Catapult Chicago, the Junto Institute, and Techstars Chicago. He also co-chairs the Digital Media & Technology subgroup at Hyde Park Angels, where he evaluates and recommends companies for presenting to the broader membership.

Craig is quite obviously someone you should take a few minutes to listen to.

If you’d like to actually meet Craig you can reach out to him for an invite to Deck Tech, a monthly gathering of Chicago’s tech scene on the amazing cleverbridge rooftop.

Craig shares 5 lessons he’s learned bootstrapping cleverbridge:

1. Necessity is the mother of invention. When you don’t have cash to burn you have to find creative solutions to business growth.

2. Don’t be someone you’re not. If you’re really good at sales, do sales. Don’t be a programmer. Hire people with the skills you lack.

3. Hire skill sets, not degrees. It’s tough to compete with the bigger players who want in on the elite university talent pool.

4. Look for talent in unusual places. cleverbridge scored a bunch of its original Chicago talent on craigslist.* Many of them are key players today.

5. Forget PR. You simply don’t have the money on Day 1. You might not have it on Day 800 either. It will come. Build your business first.

* Not the same Craig!

Watch another FIVEinSIXTY bootstrapper: ContextMedia Co-Founder Shradha Agarwal

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