Sider Road · Private Mastermind
The Trusted Advisor
Mastermind
For wealth managers and financial advisors who work with business and family wealth across generations.
"The real problems in a client's life aren't on the balance sheet. They're in the room."
— Jocelyn Greenky, MBA
Why this room exists
Your clients aren't just managing money. They're managing families.
With all the conflict, silence, and history that entails. When the money moves to the next generation, everything you've built moves with it — or doesn't.
This mastermind is for the advisor who understands that the hardest part of this work is rarely financial.
Why masterminds work
The data, for the skeptics.
Benjamin Franklin didn't have the data when he started his in 1727. He just knew it worked. Now we have both.
Is this a fit?
Who it's for — and what we work on.
Who this is for
- Wealth managers with multigenerational client relationships
- Financial advisors navigating family dynamics alongside financial ones
- RIAs building a referral-based practice
- Advisors managing estate and succession transitions
- Those who want to be indispensable — not replaceable
What we work on
- Retaining clients through generational wealth transfer
- Navigating family conflict without losing your trusted role
- Reputation management in a referral-driven business
- The conversations your clients are avoiding — and how to lead them
- Positioning yourself when the next generation takes over
How it works
The structure.
Twelve 90-minute sessions, every other week over six months, live on Zoom. Each session, one member brings a real situation they're navigating — a client relationship at risk, a transition going sideways, a conversation they don't know how to have. The group works it together.
The week before your hot seat, you and I meet 1:1. We identify the real issue, sharpen the framing, and I coach alongside — so you come into the room ready.
The agenda always belongs to whoever is in the chair.
Let's be clear
What this is — and what it isn't.
This is not
- A course with videos you'll watch at 1.5× speed and forget by Thursday
- A webinar you half-watch on mute while eating lunch
- Networking — you're not here to collect business cards
- Generic practice-management advice that applies to everyone and therefore no one
This is
- A peer advisory board — small, curated, confidential
- Real situations from real practices, worked in real time
- A place to say what you can't say inside your own firm
- Honest feedback from peers who have nothing to gain from steering you wrong
What gets worked on
Sample hot seat topics.
These aren't a fixed curriculum — they're examples of what members have brought to the chair. Every session is driven by the member whose turn it is.
The program
What's included.
The outcomes
What you walk away with.
- A retention strategy for your most important multigenerational relationships — before the wealth transfer, not after
- The language and framing to lead the conversations your clients keep avoiding
- A clear way to position yourself with the next generation as their advisor, not their parents'
- A referral and reputation plan for a business that runs on trust
- Seven peers who know your practice, your blind spots, and your goals — and will hold you to them
- A facilitator who has seen this movie before — and knows how it ends both ways
From the room
What members say.
"I'd been the founder's advisor for nineteen years and had never had a real conversation with his daughter. The room wouldn't let me leave that alone. That relationship is now the strongest one in my book."
Wealth Manager · 2025 cohort
"The 1:1 prep before my hot seat changed what I brought to the room. I thought my problem was a referral source going quiet. It wasn't. Jocelyn saw that in twenty minutes."
RIA Principal · 2025 cohort
"Seven other advisors who have no stake in my answer and no reason to flatter me. I don't have that anywhere else — not at my firm, not at conferences. That alone is worth the seat."
Financial Advisor · 2025 cohort
Names withheld — every member signs a mutual NDA. References available in conversation.
Your facilitator
Why I run this group.
I've spent 40+ years advising businesses — including family-owned ones — through succession, conflict, and transition.
I run my own advisory practice, Sider Road, alongside my daughter. I don't just study the multigenerational model. I live inside one every day.
I've seen what happens when the money moves and the advisor doesn't. I built this group for the ones who are determined not to let that happen.
Before you inquire
Frequently asked questions.
Is everything confidential?
Will my competitors be in the room?
How is pricing handled?
What is the 1:1 prep coaching?
What if I can't make a session?
Do I need a certain book size to join?
What happens after the six months?
Also available
Other mastermind tracks.
Not the right room? One of these might be.
8 seats · 2026–2027
Be the advisor the next generation keeps.
Every inquiry is reviewed personally. Investment details are shared in conversation, alongside discussion of your practice, your clients, and your goals.
Inquire for Investment Details →Or email info@siderroad.com