Insights From The Great Lakes

This post originally appeared in TECH Cocktail.

I attended the Great Lakes Entrepreneur Bash which was a panel event in Chicago that brought together successful entrepreneurs highlighted in Bob Jordan’s new book How They Did It: Billion Dollar Insights from the Heart of America. The stellar panelists included:

  • Bill Deville: Co-founder & CEO of Health Carousel, previously co-founder Health Personnel Options
  • Jim Dolan: CEO of The Dolan Company, previously was EVP of the Jordan Group Inc.
  • Tim Krauskopf: Principal at Round Lake Designs LLC, co-founder of Spyglass whose version of Mosaic became Microsoft IE
  • Chris Moffitt: Co-founded Rubicon Technology and previously co-founded Diamond Management and Technology Consultants and Technology Solutions Company
  • Vince Pettinelli: Founder of PeopleServe which was acquired by ResCare
  • Michael Polsky: Founder & CEO of Invenergy, previously founder of SkyGen Energy
  • Mark Tebbe: Co-founder & lead director of, previously founder of Lante Corporation
  • Robert Jordan: Author and owner of two companies, RedFlash and interimCEOinterimCFO

The vision for the event was to provide the audience with the “secret sauce” of going from a solo startup founder to thousands of employees and millions in profit. As only an hour-long event, it couldn’t fully deliver on its promise, but there were some fascinating peeks into the Chicago-land tech scene and insights from its successful entrepreneurs.

1. The only way to do it is to do it your own way. From exit “numbers” to building for the long run, recurring revenue to living for the next deal and public vs. private companies, every panelist had their own unique take on the different entrepreneurial angles. Michael Polsky summed it up best when he said, “Everybody will do it their own way, you really can’t do it any other way.”

2. Love what you do, be good at it and have fun with it. If not, get out quickly. The passion and conviction leapt out from every single entrepreneur on stage. It was clear as daylight that they loved what they did. And if they weren’t having fun they didn’t hesitate to sell like Mark Tebbe with Lante Corporation. Mark then went on to co-founder and stressed the importance of “doing what’s important to you and doing it well.” Jim Dolan waxed poetic about “the magic of inventing a future that’s more fun than yesterday.”

3. The only thing you should count on is persistence. The media generally paints out a tidy story for successful entrepreneurs that show them headed to great things the moment they start out on their own. The reality couldn’t be further away from it. More than one panelist talked about their weakest moments – Jim Dolan mentioned going into bankruptcy twice and Mark Tebbe jokingly said that he still hadn’t recovered from financial mishaps. The only thing they all agreed on unanimously was resilience. Chris Moffitt said “when there’s a tragedy, stand up, dust yourself and move on.” And move on they eventually did to bigger and brighter things. Jim Dolan hearteningly pointed out that if you do pick yourself back up, you’ll find that the people who invested in you will be willing to back you again.

4. Entrepreneurship requires a higher risk profile. The key message that all the panelists hammered home was that if you’re brave, courageous and willing to take chances, albeit calculated, then the world is yours for the taking. Chris Moffitt said that entrepreneurs should have the appetite to shake up the business even if and especially if the opportunity was within a billion dollar market. He also mentioned that things may not work out exactly how you imagine but if you’re willing to take a chance, then you can find a way to make it happen.

5. Entrepreneurs love it so much they end up being serial entrepreneurs. Bob Jordan, who moderated asked what the panelists did when they had financial market fluctuations and Chris Moffit readily quipped, “Start another company.” The fun of making a startup work seems so addictive that all the speakers went on to found multiple companies.

Other fun and insightful quotes from the event include:

  • “Making a bad sale is like building a dream home, taking your time to decorate it and then selling it. The buyer moves in and says you can keep living there but asks you to move to the basement. Then they proceed to undo all the things that made the house special in the first place.” Chris Moffitt
  • “If you celebrate your ignorance, you’ll surround yourself with people who are smarter than you are.” Vince Pettinelli
  • “If you can find a way to make money while you & your team are sleeping, that’s a great day!” Mark Tebbe
  • “Dissect your mistakes, analyze them but definitely don’t bury them.” Jim Dolan
  • “Do I wish my company had sold for more? Yeah, but I also wish I was taller and many other things.” Mark Tebbe

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