Managing director
TitletownTech | Green Bay
Craig Dickman was among the original architects of TitletownTech, a venture capital firm formed as a partnership between the Green Bay Packers and Microsoft. An inventor with multiple patents, Dickman founded energy information and supply chain management company Breakthrough Fuel, which he scaled to 47 countries and sold to U.S. Venture in 2019. He also served as CEO of Breakthrough Fuel, Paper Transport and Master Fleet and previously held executive positions at Schneider National and SHADE Information Systems. Dickman is chairman and principal owner of the Wisconsin Timber Rattlers, a minor league affiliate of the Milwaukee Brewers, and the Fond du Lac Dock Spiders, a summer collegiate team in the Northwoods League. He also serves on the board of the Green Bay Packers and the Wisconsin Professional Baseball District.
Education: Bachelor’s, University of Wisconsin-Green Bay; MBA, University of Wisconsin-Oshkosh
Favorite movie: “Field of Dreams.”
Highlights of the past 12 months: “We have expanded our partnership with Microsoft with the launch of the new AI Co-Innovation Lab in Wisconsin for Manufacturing, located at UW-Milwaukee.”
Favorite Wisconsin destination: “I am biased, but it is Neuroscience Group Field, where the Wisconsin Timber Rattlers play! “
Thing to learn this year: “It’s all about new technology – AI, Quantum, Autonomy, etc. – and the possibilities of solving big problems.”
2022 Wisconsin 275 Profile
Emerging Industries | Startups
Managing director
TitletownTech | Green Bay
Craig Dickman leads TitletownTech, an innovation fund formed out of a partnership between the Green Bay Packers and Microsoft that builds and funds early-stage high-growth startups. Through its first fund, TitletownTech has invested in 23 startups, three of which have relocated to Wisconsin. It aims to raise $80 million for its second fund. Prior to becoming managing director of TitletownTech, Dickman was chief executive of De Pere-based Paper Transport Inc. and Green Bay-based Breakthrough Fuel, which he founded in 2004, and served as vice president at Green Bay-based Schneider National. He also co-founded the De Pere-based venture capital and accelerator firm N.E.W. Venture Foundry in 2015. Dickman is chairman and owner of the Wisconsin Timber Rattlers, an owner of the Fond du Lac Dock Spiders and a director on the Packers’ board.
Education: Bachelor’s, University of Wisconsin-Green Bay; MBA, University of Wisconsin-Oshkosh
What was your first job and what did you learn from it?
“My first job was in retail – as an ice-cream scooper – at 14. I learned to work with a wide range of people and the value of showing up on time.”
What piece of advice has had the most significant impact on your career?
“When I graduated, I had someone tell me, ‘Never work for someone you don’t respect.’ It’s amazing how much I’ve thought about that advice over the years, and it led me to work for many people I have great respect for and from whom I learned much.”
If you could have dinner with any two business leaders, who would you choose and why?
“Elon Musk and Peter Thiel. They are both incredible entrepreneurs and creators in their own right, have history together as partners – sometimes uneasy partners – as they brought PayPal.com to market and each has had significant creative impact post-PayPal. What also intrigues me is that they appear, in many ways, to be polar opposites in every way except one…they are great entrepreneurs.”
What are some of your favorite destinations/places to visit?
“Key West, Florida, and several places across Alaska. Obviously, for very different reasons.”
What is one book you think everyone should read (or podcast everyone should listen to) and why?
“‘The Innovators,’ by Walter Isaacson. As someone who grew up as the digital age emerged – and whose first computer was a Tandy TRS-80 – the exploration of the people behind the creation of the computer, internet and digital revolution was fascinating.”
What’s your hobby/passion?
“Baseball. I played it when I was young, coached it as my kids were growing up and love visiting ballparks around the country. It led me to acquire two baseball teams – the Wisconsin Timber Rattlers, the class High-A affiliate of the Milwaukee Brewers, and the Fond du Lac Dock Spiders. My passion has evolved from a love of the game to sports as a business.”
What is your favorite Wisconsin restaurant and what do you order there?
“Jake’s Pizza in Green Bay, WI. It’s a single-location, family-owned business that I first found when I was going to college and where I took my wife on our first date. The pizza is always great, and the beer is always cold.”
What would people be surprised to learn about you (fun fact)?
“I spent about three years working as a contractor in the space industry and was able to watch a rocket launch live on a lunar mission, see the first images coming down in real-time from the first Mars rover, Sojourner, and see the first images of the asteroid Mathilde while a spacecraft flew by the asteroid.”
What was your first car? How long did you drive it for?
“My first car was a burgundy 1974 Camaro with a black interior. I kept it for as long as I could afford the maintenance bills, which was, unfortunately, shorter than I wished.”
If you could take a one-year sabbatical, what would you do?
“Write. I would love to take a break and capture what I have learned – and the inspiring people I have learned with – and get it on paper. I always saw romance in the written word.”
What’s the toughest business challenge you’ve had to overcome?
“Disrupting an industry that didn’t want to be disrupted. I had learned about intense competition, but I never really conceptualized how different it is to face intense opposition. I had to learn this new concept in real time and then determine how to manage in an unfamiliar environment. I also learned not to fight the distractors but rather to stay focused on the value we were creating.”
What advice would you give to a young professional?
“Two things. The same advice I was given, ‘Never work for someone you don’t respect,’ and ‘Embrace opportunities and take risks that align with your passions.’
What has been your/your company’s most significant success over the last 12 months?
“Showing that we can be a beacon for innovation and entrepreneurship in Wisconsin and earning the opportunity from our partners, the Green Bay Packers and Microsoft, to launch a second fund to continue building.”
What is one thing you would change about Wisconsin to make it even better?
“Make it easier for new arrivals in to feel at home. Sometimes our greatest strength is our greatest weakness. We are family- and friend-oriented, but that can make it hard for newcomers to break in and feel they belong.”
As you enter your office, what would you choose to be your walk-up or theme song and why?
“‘Growing Older But Not Up,’ by Jimmy Buffett. First, Jimmy (not Warren) Buffett is my favorite artist, and the song begins with baseball and reminds me to think young.”
Is there a nonprofit cause that has special meaning to you?
“My family and I have been active in supporting innovation in education and have helped build and design six studios in educational settings: one while I was still at Breakthrough, a ‘Breakthrough Studio’ at UW-Green Bay, four ‘Solutionist Studios’ in each elementary school and one ‘Solutionist Studio’ in the middle school in our hometown school district. The studios are designed to be places to use creativity and technology to solve problems.”
What is the biggest risk you have ever taken?
“While jumping out of an airplane is a close second, choosing to be a partner, president and CEO of a company, Paper Transport, Inc., on September 18, 2001. There was so much uncertainty in the world right after 9/11, and it felt like so much was out of our control. It was a difficult time to make a major professional change, but it was 100% worth it!”
What’s at the top of your bucket list?
“Visiting Australia. While I have been fortunate to travel to many countries and amazing places, Australia is the one place I have always wanted to visit but have not yet.”
What has you most excited about the future?
“The power of creative minds and technology to solve the world’s biggest problems.”
