Ep30 Bob Brogan—Road Warrior to Business Architect: 40 Years of Transforming Companies
Episode Summary
Bob Brogan shares four decades of experience transforming companies across operations, IT consulting, and strategy. From early data warehousing in Canada to leading a $100M exit for a 43-year-old online ordering pioneer, he discusses business cycles, modular design principles, and the transition from tactical execution to strategic leadership. Now managing partner at Tech CXO Great Lakes, he emphasizes paying forward through mentorship, angel investing, and community work including founding the Legacy Guild scholarship program.
Key Quotes
"Good deals always get done—it just takes longer in bad liquidity cycles. Design all the due diligence components so you're always ready for the data room."
"The loneliest part of the journey for entrepreneurs is not having somebody whispering in your ear. Figure out what you don't know and find the expert to fill that blank."
"I took outstanding receivables from 138 days to 38 in one summer, just by asking and sending a few letters. We went from running the business out of a checkbook to a $100M exit in 15 months."
Transcript
Hi, welcome to Tales from the Sky Lounge. It's a podcast about business, consulting, and venture investing. We get out there in the world and we talk to people who are making it happen and we get their stories. And today in the Sky Lounge, Bob Broen. Hey, Bob. Welcome to Sky Lounge.
Thanks, Todd. I've spent many a year in the Sky Lounge. I'm a road warrior for more than 20 years working in operations, IT consulting and strategy. I've spent a lot of time in sky lounges especially from a work standpoint. It's allowed me to travel the world and go through exciting adventures and journeys.
Very cool. Well, we're very eager to find out a little bit more about you and what you're working on. Right now you're managing partner at Tech CXO for the Great Lakes region. So I'd love to talk to you about that a little bit, but first I want to understand how does a guy from that's a Packer backer move to Chicago and become a Bears fan?
So I'll do the short bridge version. My grandfather and great uncle were George Halas's best friends and they went to high school together and I guess my grandfather was a high school football star with Halas. After he got out of Illinois, my grandfather and great uncle gave him the money to start the Bears. No kidding. How about that? Yeah, which is crazy. So my grandfather got his 10% of the shares back in the 1930s or 1940s, and my great uncle's kids sold out in 1989 for 28 and a half million somewhere. I don't know the exact number. I didn't get their tax returns. But when I was 5 years old, we moved from Chicago, suburban Chicago to Green Bay, Wisconsin. So my entire schooling from kindergarten through high school was in Green Bay and the rampant Packer fans, it was difficult to remain a Bears fan. But I have a bigger alliance to my mom. So that's how it goes. I love the Bears. I'm tired of them winning the off season and then falling on their face year after year. So anyway, Dub Bears.
Yeah, Dub Bears. Right. So you got it honestly and you grew up deep in enemy territory over there in Green Bay.
Want to go deeper?
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