How to Operate a $100M+ Holding Company | Michael Girdley on Holdco, Businesses and Success

“If you have good people and the right person in the seat, they're going to have a better hit rate than you. Which, may be jarring to people who are like, “I'm really good at business.” Well, it turns out, you, with limited information and partial focus, is not better than somebody else.”

— Michael Girdley

This week Sachit (@sachitgupta) chats with Michael Girdley (@girdley), business entrepreneur and investor. Michael is Chairman and co-founder of Dura Software, the second-largest software company in San Antonio, Texas. His Holding Company includes a variety of businesses including Codeup, Effectual Ventures (a venture studio), Red Runner Coffee, Near (a talent platform), and others.

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(0:00) - Introduction (02:15) - The difference between a CEO, an operator, and an idea guy (03:30) - The transition from being an operating CEO to a holding company’s CEO (08:47) - Describing the HoldCo model and why he switched to it (13:46) - Advantages & disadvantages of the HoldCo structure Vs one company model (21:08) - How he quick started the HoldCo model of operating (26:45) - What he has learned about hiring and retaining top performers (34:02) - The process of finding & hiring CEOs, with some examples (39:20) - Tests or questions you ask a candidate to check if they’re a good fit (46:52) - How do you separate yourself from being a HoldCo’s CEO from a company’s CEO? (51:21) - The day-to-day differences between being an operating CEO Vs a HoldCo CEO (53:43) - The moment when Michael realized he don't know everything (57:12) - What the operations of HoldCo actually looks like (1:04:57) - Some of the early mistakes in the HoldCo model and how to avoid them (1:10:33) - Rapid fire questions with Girdley  (1:17:35) - Closing remarks