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Men Leading the Family Business | Mastermind | Sider Road
M

Mastermind · Men Only · Family Business Leadership

Men Leading
the Family
Business.

A peer advisory mastermind exclusively for men who own, lead, or operate family businesses — and want a room where they can think out loud, sharpen strategy, and solve the hard problems with other men who actually get it.

Apply for the Next Cohort See How It Works
8
Men Max
7
Weeks
90
Min / Session
Men Only Family Business Leaders Peer Advisory Format Facilitated by Jocelyn Greenky, MBA 8 Members Maximum Zoom or In Person Confidential Apply Now · 2026 Cohorts Open

Why This Mastermind Exists

Some conversations
are better had
among men.

Family business is unlike any other business. The stakes are personal. The org chart is also the family tree. And the decisions you make at work follow you home — every single night.

There's a real and growing demand from men who lead family businesses for a space that's exclusively theirs — where they can speak frankly about succession, authority, sibling dynamics, financial pressure, and the weight of legacy without self-editing.

This mastermind was built for exactly that. No mixed-format peer groups. No corporate jargon. Just a tight room of men navigating the same terrain, led by one of the most respected advisors to family enterprises in the country.

"The hardest part of running a family business isn't the business. It's knowing when you're the founder, when you're the son, and when you're the boss — sometimes in the same hour."
01 Family businesses generate 70% of global GDP — and most leadership transitions fail due to relationship breakdown, not business failure.
02 Men in family businesses consistently report feeling isolated in their leadership role — too close to the family to confide in them, and too embedded to outsource decisions.
03 The most effective leaders aren't the ones with the best ideas — they're the ones who have a room they can think in before the decision has to be made.

Is This For You

You belong here if...

🏗
You own or lead a family business Whether you're the founder, a second-generation operator, or a son stepping into leadership — you're running something real, with real stakes and real family relationships in the room.
🔒
You want a confidential space You can't have this conversation with your CFO. You can't fully have it with your father. You need a room where what's said stays said — with men who understand what you're carrying.
⚖️
You're navigating authority and relationships simultaneously You're a leader, a family member, a partner in the business — and the lines between those roles blur constantly. You want to lead with more clarity and less tension.
📈
You want sharper business strategy, not just venting This isn't a support group. It's a peer advisory room. You want actionable frameworks, real feedback, and the kind of strategic thinking that changes how you run the business Monday morning.
🧭
You're thinking about succession, transition, or growth Whether you're planning to pass the torch, bring in the next generation, or scale beyond the family structure — you need a smart room to think it through before it happens to you.
🤝
You want to be around men who get it You've been in rooms where nobody understands what it actually means to work with family. This is the room where everyone does — and the conversations are different because of it.

The Format

Built for leaders,
not lecture halls.

01
The Room
Capped at 8 men. That's not an accident — it's the number that allows everyone to get real airtime, real feedback, and a genuine relationship with every other member. No one gets lost in the group. No one gets to hide.
8 Members Maximum · Private Cohort
02
The Sessions
7 weeks. Bi-weekly. 90 minutes per session. Each meeting includes structured teaching, hot-seat problem-solving, and live Q&A with expert guests. Available via Zoom or in person — designed to fit your schedule without excuses.
7 Weeks · Bi-Weekly · 90 Min · Zoom or In Person
03
The Outcomes
You leave with sharper strategy, a clearer leadership identity, and tools you can use the morning after every session — not in six months when things have shifted again. Members regularly continue after the initial cohort ends.
Actionable Takeaways · Ongoing Community

What We Cover

The conversations you haven't
had anywhere else.

Every session is structured but never scripted. The agenda is built around what the room needs. These are the core territories we cover — and the conversations that tend to go the deepest.

01
Authority Without War
How to claim and hold leadership authority in a family setting without igniting resentment — across generations and across roles.
02
Succession Strategy
Planning transitions that protect both the business and the family. When to pass the torch, how to structure the handover, and how to stay involved without undermining what you built.
03
Family Governance & Structure
Building the agreements, roles, and decision-making frameworks that keep business and family relationships from colliding in the worst moments.
04
Communication Under Pressure
How to have the hard conversations — compensation, equity, underperformance, exits — with family members, without permanently damaging the relationship.
05
Leadership Identity
Defining yourself as a leader — separate from your role as son, father, or brother — and building the executive presence and reputation that earns real respect inside and outside the business.
06
Generational Dynamics
Navigating the gap between how things were done and how they need to evolve — without dismissing legacy or being paralyzed by it.
07
Operational Clarity
Cutting through the noise to build systems, accountability, and workflows that actually function — even when your team is also your family.
08
Conflict Navigation
What to do when business disputes become personal, when alliances form, when resentment builds quietly. Real strategies for real family business conflict — not corporate HR frameworks.

2026 Schedule

Current cohort
availability.

Format
7 weeks, bi-weekly · 90 minutes per session
Cohort A
Tuesdays · 12:00–1:30 PM EST
Starting January 20, 2026
Cohort B
Tuesdays · 4:00–5:30 PM EST
Cohort C
Fridays · 11:00 AM–12:30 PM EST Sold Out
Cohort D
Mondays · 12:00–1:30 PM EST
Delivery
Zoom or In Person (your preference)
Group Size
8 men maximum — apply early
Facilitator
Jocelyn Greenky, MBA

Investment

Ready to
apply?

Membership is by application. Seats are limited.

The group stays at 8 for a reason. Every member is vetted to ensure the right fit — for you and for them. A brief call with Jocelyn's team is the first step. Investment details are shared during that conversation.

Ongoing peer advisory — group continuity discussed at enrollment
Confidentiality is foundational — what happens in the room stays there
Members are active family business owners and operators
Each cohort is curated for complementary dynamics, not identical situations
Schedule Your Application Call

Your Facilitator

Jocelyn Greenky, MBA

Jocelyn Greenky is a business transformation strategist and one of the most trusted advisors to family enterprises in the country. With 40+ years inside boardrooms, family businesses, and leadership teams across North America, South America, Mexico, and Europe, she has seen — and helped navigate — every iteration of what it means to lead when it's personal.

She has spoken at the United Nations, Fortune 500 companies, and MBA programs worldwide. Her thought leadership has been featured in The New York Times, Forbes, Fortune, Wall Street Journal, Washington Post, Entrepreneur, Business Insider, and more. She is an adjunct professor at NYU Tisch School of the Arts and the author of a nationally recognized book on business and relationships.

She facilitates this group because she understands that the most important conversations family business leaders need to have — they can't have anywhere else.

MBA — Columbia University
40+ years advising family enterprises
Speaker: United Nations, Fortune 500, MBA Programs globally
Adjunct Professor, NYU Tisch School of the Arts
Featured: NYT, Forbes, Fortune, WSJ, Washington Post
"Men in family businesses are often the most isolated leaders in the room. They can't fully talk to their family. They can't fully talk to their team. This mastermind exists to give them a room that's actually theirs."

Jocelyn doesn't just facilitate — she challenges. She's been inside enough family businesses to know when a story is real and when it's the version someone tells themselves. The room she creates is safe, but it's not soft.

Learn More About Jocelyn

From the Room

What members say.

"I've been in mastermind groups before. This is the first one where I actually said what I meant. Being in a room with men who are in the same situation — you stop translating. You just talk."

Darius Miller
Family Business Operator

"I came in thinking I needed better systems. What I actually needed was a clearer sense of my own authority — where it starts and where it ends. This group helped me find that."

Tom Wenceslao
Second-Generation Business Leader

"The hot-seat format is uncomfortable in exactly the right way. You can't hide. And when six other men who run family businesses are giving you feedback, you listen differently than you would anywhere else."

Member, 2025 Cohort
Family Business Owner

"Jocelyn doesn't let you off the hook. She's seen too many family businesses to accept the comfortable version of the story. That's exactly what I needed — someone who could see around the corner."

Member, 2025 Cohort
Founder & Family Business Operator

Limited Cohorts · Men Only

The room is waiting.
Apply now.

8 men. 7 weeks. The conversations you've needed to have for years — in a space built for exactly this.

Apply for the Next Cohort What Is a Mastermind?

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