Three generations and 300 family members in a holdco

Hey folks,

Multi-generational operators like the Dolans bring decades of perspective to HoldCo conversations.

Today's story comes from Charlie and James Dolan's presentation at HoldCo Conference 2025. They’re a father-son duo managing a holding company that spans three generations and nearly 300 family members.

Most families can't agree on where to go for dinner. The Dolans built a business empire that keeps everyone aligned across decades.

Here's how they did it.

How Three Generations Stay Aligned Through One Holding Company 

From Charlie and James Dolan's talk at HoldCo Conference 2025

"We don't usually talk about this stuff," Charlie Dolan warned the HoldCo Conference audience before diving into the most candid family business discussion of the weekend.

What followed was a master class in multi-generational wealth building from a father-son team managing nearly 300 family members across three generations of holding company structures.

The Dolans' thesis cuts against conventional wisdom: holding companies can actually bring your family closer together.

"That doesn't mean it needs to be perpetual across three or four or five generations," Charlie explains. "It could just be iterations for each one and letting people get the space to do their own move."

The Dolan family empire operates across three distinct levels, each serving different generations and goals:

Level 1: The Foundation - James Dolan's generation built the initial wealth through a mutual fund company that went public twice. "My whole goal over my years was to build businesses, create them and monetize them," James reflects.

Level 2: Voyager Holdings - The diversification vehicle James created for his six sons. Today it operates timber and natural resource businesses, fiber optic companies in Montana, and data center operations on the East Coast.

Level 3: SEQ Holdings - Charlie's "digital garbageman" business, spun out from the family's waste brokerage sale. This level focuses on the next generation, with shares distributed to grandchildren through family trusts.

The scale is staggering: between James's father-in-law's side and their own kids, they're managing the interests and expectations of almost 300 people.

How do you manage family dynamics when business disagreements could ruin Thanksgiving dinner?

"I've been fortunate enough to have those family values run alongside the company values to where we do tend to all get along, even when there's disagreements," Charlie explains. "Had a family wedding this weekend—I get people that write spicy emails to me about stuff and we'll still be able to hang out at the same table and get along."

It’s all about compartmentalization.

"While it can seem a little obscure, it's a very useful skill being able to separate those things."

This isn't just emotional intelligence; it's structural. Each generation operates with clear boundaries and decision-making authority, preventing the chaos that typically destroys family enterprises.

The Dolans solved one of family business's thorniest problems with an elegant structure: A/B share classes.

"The A shares vote and the B shares have equity but don't have votes," James explains. "Your advisors will tell you nobody will like it. But it doesn't make any difference. I would do it, I did it and I would do it again."

James and his wife own the A shares (voting control). The family owns B shares (economic upside) at a 70% allocation. Over the next five years, James is transferring voting control to Charlie's generation while maintaining clear succession planning.

"There's value in separating the voting control versus the equity," he notes. Even with minority discount issues for tax purposes, this structure provides comfort for the controlling generation while setting clear expectations for wealth transfer.

Despite having longer time horizons than typical operators, the Dolans prioritize cash generation over growth.

"The thesis I have is to try and have it be cash flow positive quickly," Charlie explains. "No one likes a money pit. I think it's a good indication of product-market fit if you're able to get revenue in the door in the first couple of months."

James agrees: "I think if I had to do it again, I would focus on a slightly different balance. I was focused on growing the equity, and I wasn't as focused on the cash flow as I might have wanted to be."

The lesson: Even with generational thinking, cash flow discipline matters.

The Dolans represent something rare in American business: true multi-generational thinking that actually works.

Their approach isn't about control or preservation—it's about creating structures that allow each generation to build on the last while maintaining family cohesion.

"Holding companies can help bring your family closer together," Charlie concludes. But only if you architect them correctly from the start.

For operators thinking beyond their own lifetime, the Dolan model offers a blueprint for building wealth that strengthens rather than fractures family bonds.

3 Takeaways for Your Business

The best investment strategies are measured in decades, not quarters. HoldCo Conference 2026 (Feb 9-12) brings together operators thinking beyond the next exit.

Tomorrow: Peter Lehrman breaks down what's actually working in today's M&A market.

Thanks,
The HoldCo Conference Team

P.S. Discounted spouse tickets are available at checkout. Get yours today.