The Power of Small Groups

Your personal, curated advisory board

The most important decisions I’ve made in my career—hell, in my life—didn’t happen at a conference or over drinks at a networking event. They happened in small rooms, with a handful of people I trusted, talking about things that actually mattered.

Something powerful happens when you bring six, seven, maybe eight people together with one goal: to get better. Not just at business, but at life. That’s the magic of small groups. And it’s a magic I think more people—especially entrepreneurs, leaders, and creators—should tap into.

Where It Started: My First Two Groups

The first real peer group I joined was called HTG (now Connectwise IT Nation Evolve), a group of 10–12 IT company owners that met quarterly. It was hyper-specific—everyone ran an MSP—and the format was highly structured: two full days of business updates, benchmarking via a platform called Service Leadership, and deep dives into everything from operations to hiring to marketing.

That group cracked something open for me. I saw how other businesses were operating, what they were struggling with, and what success actually looked like. And while I was probably the smallest company in the room, I got in because I had a superpower—marketing strategy and lead generation. That became my value to the group. It taught me something important: if you want to be in a room with people who’ve already done what you want to do, show up with something unique that helps them.

Later, I joined EO (Entrepreneurs’ Organization) and was placed in a Forum—a small group within the larger org. Unlike HTG, which focused solely on business, Forum opened up space to talk about family, health, relationships, and personal growth.

The shift was profound. It wasn’t just about quarterly numbers anymore. It was about how I was showing up as a dad, a husband, and a leader. It was also the first time I experienced a structured, consistent space where vulnerability wasn’t just allowed—it was expected.

Why Small Groups Work So Well

1. Everyone Gets Heard
   In a small group, you can’t hide. And that’s a good thing. Everyone gets a turn. Everyone gets space.

2. Group Wisdom + One-on-One Support
   The magic is in the mix: full-group energy plus one-on-one sidebars. You share in the room, then grab coffee with someone a week later to go deeper.

3. High-Level Vulnerability Is the Point
   Here’s the truth: most of us don’t get vulnerable on purpose. We wait until life forces us to. But in a well-run small group, you’re expected to show up and be honest.

“This month has been brutal—revenue’s down, prices are up, I don’t know what I’m doing with my kid’s education, and I need help.”
That’s a normal thing to say in a peer group. And the feedback you get? It’s priceless.

4. Objectivity You Can’t Get Alone
   When you’re in the weeds, you’re emotional. Peer groups offer clarity. I’ve had people in my Forum tell me, kindly and clearly, “You need to end that working relationship.” And they were right. From the outside, it was obvious. I just couldn’t see it from where I stood.

5. Peer Pressure for Growth
   The best peer groups create gentle pressure. Everyone’s doing the work. Everyone’s trying to grow. You want to show up ready—not just for yourself, but because the group is counting on you.

How to Build Real Trust: Becoming Fast Friends

Becoming fast friends isn’t easy. But it’s necessary. Here’s how to accelerate trust in a group:

• Start with icebreakers. I keep a running list here of great ones.

• Do a Lifeline Exercise—a visual timeline of your life’s highs and lows that you share with the group.

• Invite someone to present on a challenge. In some groups, we call it spotting “green tails”—repetitive themes that deserve a deeper dive.

• Reinforce confidentiality at every meeting. Trust is built on safety.

And don’t underestimate the power of time outside the agenda. The best groups also spend time just being friends: grabbing lunch, going to a Heat game, hosting each other’s families, or planning a boat day. That informal time deepens the connection—and that connection deepens the value of the group.

Growth Mindset & Formality

A great small group never stays static. It evolves.

In all of my groups, we regularly ask:

“Are you still getting 10/10 value from this?”
And if not, what would it take to get there?

That kind of reflection is part of a growth mindset. It keeps the group fresh, the topics relevant, and the members engaged. It also encourages self-accountability: if you’re coasting, why? What’s getting in the way?

Some of my groups are highly structured, like EO Forum or HTG. Others, like my Monday Dinners, are casual, salon-style conversations over a meal.

Formal groups have agendas, rules, and trained facilitators.
Informal groups run on curation, consistency, and good conversation.

Both types work. But the key is intentionality. You have to show up with the desire to give and grow.

How to Choose or Start a Group

Before you join or start a group, ask yourself:

• Do I want to focus on business, life, or both?

• Am I looking for people in my industry or people at my life stage?

• Do I want deep accountability, or more of a loose learning circle?

Be selective. Look for:

• Shared values

• Confidentiality

• Diversity of thought

• A culture of openness and preparation\

And remember: you’re not just joining the group. The group is joining you, too.

What No One Tells You About Small Groups

The thing no one tells you is this:

Small groups can transform your life.

If you’ve never had a place to be vulnerable—really vulnerable—they’ll give you that.

If you’ve never had honest feedback from people who care about your growth—they’ll give you that.

If you’ve never been part of a group that made you better just by showing up—you’re in for something special.

It might change how you run your business.

It might make you a better parent or partner.

It might reconnect you with a version of yourself that’s been buried under stress and noise.

That’s the power of small groups.

Want to Join One? Start Here:

• Entrepreneurs' Organization (EO)

• Young Presidents' Organization (YPO)

• Vistage

• Tiger 21

• Hampton

• Or make your own!

P.S. – EO South Florida

If you're a founder, co-founder, or majority owner of a business based in South Florida, and you're looking for a real group of peers to grow with—you should absolutely check out EO South Florida.

Coincidentally, I’m the current Membership Chair—so if you're curious about what it's like, or want help applying, shoot me a note directly. Happy to chat.