How I run 11+ businesses at once

Without being (too) insane.
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Hey folks! 

Hope everybody’s doing well. As a holdco guy, I get this question all the time: 

How do I actually run 11+ businesses at once?

As a guy with a bunch of businesses, I’m all about parallel entrepreneurship. Lots of balls in the air at once.

But when people hear what I do, they always ask: “How do you run that many companies at one time?”

Well, here’s the truth of it:

I work myself out of a job as fast as I can.

When I start a new venture, I only look for scalable ideas — that is, stuff that can grow to 100x without taking 100x more work.

My other favorite practice is to partner with young, hungry people who are early in their careers. That way we can complement each other: they bring ambition, drive, and potential, and I bring experience, resources, and network.

They get to be CEO. I move up to Chairman of the Board, available as an advisor, mentor, whatever they need.

That introduces the next challenge: if my main interaction with my companies is through board meetings, I want that board to be as effective as humanly possible. 

Here’s how I do that:

  • Clear corporate structure
  • The “3 Cs” of an effective board
  • World-class board meetings

It works super well.

Let’s break it down.

Corporate structure in GirdleyWorld

In my HoldCo, each company has a Chief Executive Officer and a Board of Directors.

The CEO runs the business and is responsible for it. 

I believe “real” CEO roles are full-time and all-consuming. Done right, a person can only hold one CEO job at a time.

The Board does 3 things:

  1. Manages and coaches the CEO
  2. Approves plans and budgets
  3. Helps out in tough challenges

By design, the Board has limited responsibilities. So, each board requires just a few hours of my time each week. 

My job is being on the board while not working IN the company. That’s how I scale ownership and supervision beyond a single organization.

I can be on 5, 6, or even more boards. With time left over.

Challenges for the board

Being on the board isn’t as easy as it sounds. There’s some stuff I wouldn’t face if I were in a single business:

  • Removed from day-to-day operations, my info is limited
  • One company could bring down everything
  • My mindset had to change (I’m no longer the ‘man in the arena’... I’m coaching from the sidelines)

But it can work, and it’s how I scale. The key is making the most of every board I’m part of. 

That’s where my framework comes in.

The 3 Cs of An Excellent Board

Every board differs based on the situation. My job is to build the right board for the company. For each business, I fine-tune these three dials to get the best fit:

1) Composition

My rule: keep my board as small as possible. At its core, I can have a board with just me. I might recruit a strategic outsider. Or, if there are other equity holders, they’ll want seats. I keep it an odd number, so no ties are possible.

2) Culture

I define my board’s culture. I put it in front of the deck for every meeting. Here’s the slide from my made-up company Grilldley’s: 

 As chair of the board, I manage the culture by holding people accountable. More than once, I’ve given the “This is unacceptable behavior” speech in board meetings.

3) Meeting Cadence

The heartbeat of a board is the regular meetings.

Most of my companies do quarterly with informal monthly updates. In a distressed company, we might meet for an hour every week. It all depends on the situation. 

I’ve written a whole thread on world-class board meetings here, with a sample slide deck. (Maybe I’ll expand on it for a future newsletter topic?)

I also do regular 1-1s with CEOs as board chair. There is a ton more to this topic.

The upshot? Get the right balance for composition, culture, and cadence, and you’ll find yourself with more time to build. 

Lightning round Qs

Do you pay board members?
Not usually. Maybe a stipend. But the best board members want to invest if they can.

What if you don’t agree with your CEO?
I lean towards trusting them as the person in the trenches. But that has limits.

Do you need to be an expert before joining a board?
Business is mostly a “tastes like chicken” situation. 85% of it is the same everywhere, and that comes from your experience (ideally as a thoughtful operator yourself). You can learn the other 15% easily.

How do I get onto a board?
Bring something the company needs (money, prestige, connections, knowledge, etc.). Or if you just want the experience, lots of volunteer orgs are dying for board members.

Thanks for reading! I love the holding company structure because it lets me scale my impact on the world more than any other. 

Have a great week.

Michael