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$250,000 AI Coaching Business

This episode is a double whammy...

Not only will you get a behind the scenes look at a $250,000+/year coaching business, you'll learn 4 insanely actionable ways to utilize AI as a coach (without the endless revision cycles that take you down an endless rabbit hole).

Dan Cumberland joins me today, and he shares a TON of amazing insights both on the business front AND on the AI front. Dan ran a venture studio, which included a 7 figure exit, and now consults with some of the top brands, and a ton of creators, to help them actually put AI into action in such a way that it works for them.

This episode is a MUST listen if you've been intimidated by AI.

In This Episode:

0:00 Intro

1:00 From venture studio to AI Coaching

8:05 Dan's business at 30,000 feet

13:44 Leads

21:21 Marketing and sales systems

28:58 The morality of AI

36:17 Mining sessions for marketing content with AI

46:26 Using AI as an Assistant Coach

49:20 Summarizing sessions to mark transformations

51:26 Duplicate yourself as an AI Coach

Resources:

FREE AI Training Guide: https://aitrainingguide.com/

Dan Website: https://dancumberlandlabs.com/

AI Audit: https://dancumberlandlabs.com/ai-flow-audit/

Book A Call With Dan: https://book.dancumberland.com/ai-strategy

Dan on LinkedIn: https://www.linkedin.com/in/dancumberland/

How would you like to make half a million dollars/year, charging $3750/month for 2 coaching sessions?

If that's the kind of business you'd like to run, this is a conversation you can't miss, because that's exactly what Barrett Brooks has built.

Barrett coaches 7-figure creators and founders. Most of them come to him to hit specific revenue numbers, and they often do that, but the secret is that it's not usually a tactic or external thing holding them back.

It's usually internal, and they'd never have found out their own emotional or psychological block before working with Barrett.

This is why he can charge what he does, and why he gets the results he does.

We talk business, but we also test out something crazy...

Barrett coaches me live for the last half of the call, and I think you'll find it incredibly relatable and helpful.

(Also, on a meta level, seeing someone coach, live, is one of the best ways to "prove" your value to potential clients, so as coaches, try to find a way to do this. Barrett does it here, but also gives another way he's done this to get his first clients.)

In This Episode:

0:00 Intro

0:41 Barrett's entry into coaching

2:59 From COO to Coach

6:15 Why Barrett coaches 7 figure creators

13:17 How Barrett Makes $45000/month Charges $3750/month

17:37 First clients with LinkedIn

22:37 Barrett coaches me LIVE

44:29 Coaching review

47:08 Integration

Resources:

Little Leadership Lessons Newsletter: https://barrettbrooks.com/

Coaching with Barrett: https://barrettbrooks.com/coaching/

Barrett Brooks on LinkedIn: https://www.linkedin.com/in/barrettabrooks/

Internal Family Systems: https://ifs-institute.com/

Ever wonder why your group coaching program doesn’t feel right, even after endless tweaks?

In this episode I sit down with design strategist turned coach, Jake Wysocki, who reveals how to build a world-class group coaching experience that’s actually fun, flexible, and human-centered.

From leaving corporate design workshops to helping coaches create transformational group programs, Jake shares the real-life lessons that shaped his unique 10/50/99 framework.

They unpack how to design sessions just in time, engage clients with vulnerability, and avoid the perfection trap that kills momentum.

If you’ve ever built a program the hard way, this conversation will change how you think about coaching forever.

In This Episode:

00:00 Intro

02:38 Jake’s Journey from Corporate to Coaching

06:38 Finding His Niche in Group Program Design

12:25 Relationships for Business

16:26 The 10-50-99 Framework for Program Design

33:05 Starting with Hopes and Fears Exercise

38:54 Tips for Program Structure and Iteration

45:59 Success Story: Doubling Prices Through Relationships

50:26 Where to Learn More

Resources:

Jake's Crash Course - https://course.intentioncraft.com/

The Art of Gathering by Priya Parker: https://amzn.to/48yxboi

John Meese Episode: https://www.youtube.com/watch?v=P4iY5bf2oBY