How Craig Dickman Used Entrepreneurship To Solve Real Problems

Jan 22, 2019

Craig Dickman got his first computer, a Radio Shack TRS-80, in 1977. That purchase, a few coding classes and a lot of self-teaching (combined with two business degrees), sparked a career that landed Craig a job at Schneider National Inc., one of Wisconsin's biggest companies.

For some, that might have been enough. But never afraid of taking a risk, Craig left his job as Vice President of Information Technology at Schneider after just a year, to run Paper Transport Inc., a then-$10 million trucking company. Three years later in 2004, after listening to a customer describe a specific problem, Dickman agreed to hire and train his own replacement so he could spin out a startup called Breakthrough Fuel to solve that problem.

Under Craig's leadership, Breakthrough has grown to have nearly 100 employees, customers representing many of the world's best-known brands that transport goods in 46 countries, and the largest repository of real-time product movement data in the country. Paper Transport, which Craig stayed involved with as a board member, has grown to more than $200 million of revenue.

In early 2018, Craig turned over day-to-day leadership of Breakthrough to a colleague. Later in the year Craig was named managing director of Titletown Tech, a joint venture between the Green Bay Packers and Microsoft that's aimed at spurring economic expansion in Northeast Wisconsin by building and investing in early-stage and existing businesses.

Here are some tips Craig has for other entrepreneurs:

  • Look to solve real problems. When you are ‘in the market’ you will hear challenges and opportunities if you listen. Focus on solving those problems.
  • Become an expert. Become an expert in the area you are looking to change and make sure you are the best informed person related to your solution.
  • Enter and listen. Get into the market as fast as is reasonable with your solution and listen to the market. The market/customer reaction will tell you how close you are to the best solution.
  • Build connections. Work the marketplace and build connections across all segments that will benefit from or be affected by your solution. You will be surprised how often an existing and honest connection can support your journey.
  • Focus on building culture. When you build your team, focus on the culture you want to build and not just the jobs you want to fill.