Episode Summary

Bob Brogan shares four decades of operational and strategic consulting experience, from early data warehousing work at IBM subsidiaries to leading turnarounds and exits. He discusses his approach to business transformation through modular design, cash cycle management, and the importance of mentorship—both as an angel investor evaluating founders and through his Legacy Guild charity providing scholarships to students who've lost parents.

Pull Quotes

“I believe in the philosophy of why are phone numbers seven digits long? Because that's as long a span of numbers that you could remember. Well, four and then three. Exactly. My point being, once a company or an organization gets over six or seven core paths both horizontally and vertically in the business and they're still stuck, it's time to change your business model.”

On what he looks for in founders seeking investment

“I need help is a good thing to say to an investor. Those that know it all and present as they know it all don't typically get funded quickly.”

“Bob Brogan has been wrong more than he's been right. All you have to do is call my wife. I tell the story to a lot of people that I was only the fourth smartest person at my own dinner table.”

“If you base everything off a cash to cash cycle and you understand three or four main cost and revenue and collection drivers, just follow the dollar through each function in the business. That works in retail, that works in manufacturing and CPG.”

On preparing a company for exit from day one

“Your journey is ultimately to get to the data room. When I got called, they had turned down two previous offers to sell the business. The reason why was they knew that their financial house was not in order. They said not right now. You got to build out the components of the data room and come back from there.”

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.

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