100 Cups Mastermind

A Small Room Built for Leaders Who Are Playing the Long Game.

Weekly live conversations, real-time strategy, and a tight-knit group of business owners who understand that the best growth comes from intentional relationships and consistent momentum.

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Weekly Sessions

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Day

Every Thursday

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Time

Noon CST

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Format

Live Zoom

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Size

Small Group, Intentionally Limited

$99 / month

What It Is

Not a Webinar. Not a Course. A Real Conversation.

The 100 Cups Mastermind is a small strategy room for leaders who are serious about building relationships that grow their business. Every week, the same tight-knit group shows up, sharpens their thinking, and holds each other accountable.

This isn't passive learning. It's active, practical, and built around the people in the room. Jason facilitates every session, brings in guests a couple times a month, and keeps the focus squarely on what actually moves the needle.

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Weekly Live Sessions

Every Thursday at noon CST, no exceptions

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Small Group by Design

Kept intentionally small so every voice gets heard

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Guest Speakers (By Design, Not Default)

We invite guest speakers occasionally, only when it adds real value to the conversation

What You Get

Everything You Need to Stay Sharp and Keep Moving.

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Weekly Live Conversations

Every Thursday at noon CST, the group gathers on Zoom for an hour of focused coaching, strategy, and real talk about what's working and what isn't.

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Real-Time Strategy and Feedback

Bring your actual challenges and get direct input from Jason and the group. No theoretical frameworks, just practical guidance on the situations in front of you right now.

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Accountability That Sticks

Showing up every week with the same group creates the kind of accountability that keeps momentum going even when things get busy. The group holds you to what you said you'd do.

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Guest Speakers (Used Intentionally)

We bring in guest speakers when it adds real value, not just to fill space. The truth is, the most powerful insights in this group often come from within. Members are encouraged to share their expertise, lead conversations, and support one another with their ideas, products, and services.

Who This Is For

Built for Business Owners Who Are Done Going It Alone.

The Mastermind is a small room and it's meant to stay that way. It's for the right people at the right time.

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You're a business owner or sales leader who relies on relationships to grow and you want to keep getting better at it

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You want a consistent weekly touchpoint that sharpens your thinking and keeps you accountable

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You're tired of consuming content and ready to be in an active conversation with people who are actually doing the work

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You value learning from other people's experiences as much as your own

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You show up, contribute, and take the group seriously, not just when it's convenient

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You want access to outside voices and fresh perspective on a regular basis without hunting for it yourself

From the Room

What Members Are Saying.

★★★★★

"Thursday at noon has become the most valuable hour of my week. The group keeps me honest and Jason has a way of getting to the root of what's actually holding you back."

- Brian K., Insurance Agency Owner

★★★★★

"Jason is the heart of the group. He's a great thought-provoker and listener, which has helped me be better as a leader. I've learned that it's hard to know what's important to someone if you're doing all the talking. I leave feeling heard, valued, and on occasion, inspired."

- John Henderson, CEO, Morphe Consulting

★★★★★

"I've been part of this group for 3 to 4 years. What surprised me most is the consistency and quality of people Jason attracts. This isn't just networking, it's connection. Jason is intentional, relational, and consistent, and that shift toward relationships over transactions has changed how I approach everything."

- Brandon Hamilton, Sonshine Sovereign Solutions

Common Questions

Everything You Need to Know.

What exactly happens on the Thursday calls?

Each week is a live Zoom session at noon CST. Jason facilitates the conversation, the group shares what they're working through, and everyone gets real-time input and feedback. Some weeks have a specific topic, others are open coaching. Either way, you leave with something useful.

How many people are in the group?

The group is kept intentionally small. The whole point is that every person in the room gets heard and contributes. When the room gets too big that stops happening, so membership is limited.

What if I miss a session?

Life happens. Sessions are recorded so you can catch up. That said, the value of this group comes from consistent presence, so the expectation is that you show up most weeks.

How often do guest speakers come in?

A couple times a month. Jason is always looking for people who have real experience and something genuine to contribute to the group. It's not about big names, it's about good conversations.

Can I cancel anytime?

Yes. Membership is month to month and you can cancel anytime. The goal is to keep people because it's worth it, not because they're locked in.

Ready to Join the Room?