How Holdco Legend Michael Girdley is Playing Multi-Decade Games (and Winning)

Michael Girdley runs about a dozen businesses from San Antonio, Texas, but he does not call it a portfolio. He has been at this for a decade, and the shape of his operation has shifted sharply in the past four years. While much of the holdco world on Twitter preaches buying existing businesses to skip the painful zero-to-one phase, Girdley has gone the other direction. When assets are expensive, he argues, you create assets. So he has been incubating new companies rather than acquiring them, a contrarian bet that he believes is the right move when everyone is chasing the same deals.

The Baby Boomer Business Myth

Girdley is skeptical of the widely repeated claim that a tsunami of baby boomer businesses will soon be available for pennies on the dollar. He receives pitches about this two to three times a day, but he thinks the math does not hold up. First, many of those businesses are in industries you simply do not want to be in. Second, a huge number of them depend entirely on the owner's personal relationships, knowledge, or credentials — meaning they have no durable value without that person. Third, many boomers have already figured out an exit: they sell to a strategic buyer, pass the business to their kids, or hire a manager. What is left after filtering for all of that is far smaller than the number of buyers chasing it. "It's not a tsunami," he says. "It's something