Scaling a $100M HoldCo with Michael Girdley

Guest:

Michael Girdley

The key to scaling a $100M Holding Company - 4 words:

Right People. Right Structure.

Michael Girdley is one of the most humble, thoughtful entrepreneurs I’ve met. He manages a $100M holding company with 12+ businesses, overseeing companies that employ over 600 people in industries ranging from fireworks sales to SaaS roll-ups to offshore recruiting.

After 30+ years in business, Michael has found a way to build thriving businesses in a sane, sustainable way. 

Managing 12 companies would leave most people with little time for a bike ride, let alone one with a smile this big. But not Michael. From his website:

He describes the key to his success in four words: Right people. Right structure.

What This Means:

Right People

Michael doesn’t hire or partner with people based on a good conversation or a gut feeling. He takes a methodical approach to talent selection. 

He knows you can’t scale anything without the right people. As I’ve studied his approach, it is no surprise that he is as methodical as it gets in terms of people selection.

The bedrock of his hiring philosophy involves two main elements:

1. Understanding Revealed Preferences: The Structured Behavioral Interview

To predict someone's future judgment, choices, and trajectory, Michael relies on understanding someone’s past. There is one kind of conversation that most reveals a candidate’s past behavior, decisions and actions: the structured behavioral interview.

Both Michael and I recommend the book Who for anyone looking to master this interviewing technique. The idea is simple: the best predictor of future behavior is past behavior.

2. Analytics Over Instincts: The Culture Index Assessment

A good interview alone isn’t enough. To go deeper, Michael requires any potential partner or key hire to take the Culture Index assessment. 

The Culture Index assessment tool measures work-related traits using a free-choice adjective checklist, revealing how a candidate aligns with a role’s responsibilities and competencies. Paired with a rigorous interview process, the assessment helps ensure a strong fit for the role in question.

Right Structure

Michael is just as meticulous when it comes to structuring roles and partnerships. For every key role, he ensures all agreements are put in writing. I’ve used his templates myself to outline key terms and avoid misunderstandings down the line.

He boils down the structure of a new company partnership into a clear 1-page Memo of Understanding:

Source: Girdley.com

The clarity of well-defined structure IN WRITING prevents confusion and saves countless headaches, allowing teams to focus on growth and execution.

Building for Scale

Simple and clear isn’t easy. But when you get it right, it scales. Michael’s approach is a brilliant example of these principles in action: by focusing on the right people and the right structure, he’s been able to build a diversified holding company that thrives across multiple industries.

For more from Michael, check out his website here and on X.

Get in touch

Matt acquires or invests in cash-flowing digital businesses with $1-$5M in EBITDA.

Occasionally, he takes on advisory engagements for interesting projects. If this is of interest, feel free to share more.

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