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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

What if one strategy could transform your coaching business from stuck to scaling?

That’s exactly what happened to Dustin Riechmann, who went from engineer to marriage ministry to selling meat sticks...and finally cracked the code on building a $1M+ coaching business through podcast guesting.

In this episode, Dustin shares how he discovered his “boring” marketing method was actually a goldmine, why collaboration beats cold pitching every time, and how he’s built a thriving community of coaches around his unique flywheel model.

You’ll hear the behind-the-scenes story of how he crafted his irresistible offer, how he's built his business so big with just one full-time employee, and what’s next for his seven-figure business.

If you’re a coach looking for leads, clarity, and freedom, this conversation is packed with insights you don’t want to miss.

In This Episode:

0:00 Intro

1:34 From engineering to coaching

6:45 Winning with Referrals & Partnerships

9:50 How to find your niche (Identity vs Intent)

14:29 Where Dustin gets his leads

18:19 Being a normal, kind dude in the market

22:18 Nurturing leads

24:40 How Dustin uses HIS podcast

30:06 Why Dustin's offer is so good

34:45 The power of community

44:25 Scaling with simplicity

Resources:

FREE Podcast Guesting Playbook: https://7figureleap.com/start

Dustin's LinkedIn: https://www.linkedin.com/in/dustinriechmann/

Buy Back Your Time by Dan Martell: https://amzn.to/4pR7Hc3

Love Every Day ebook: https://www.scribd.com/document/26484217/Love-Every-Day

LAUNCH YOUR PODCAST: https://calendly.com/proclaimpodcasting/podcast-discovery-call

What happens when a recovering project manager accidentally becomes a prison coach?

That’s exactly the story of Jacqueline (Mama J) Hollows, who went from volunteering with recovering addicts to transforming lives behind bars.

In this episode, she shares her powerful journey from burnout and money wounds to building a coaching business that empowers socially conscious coaches.

You’ll hear how she bridged authenticity with business, why charging for transformation matters, and the surprising world of government contracts and funding.

If you’ve ever wondered how to truly get paid to do the work you love while making a difference, this conversation will open your eyes.

In This Episode:

0:00 Intro

1:06 Accidentally Becoming a Coach

4:31 Going from "helping" to running a coaching business

8:28 Coaching in prisons and addiction recovery

16:36 Money wounds and being able to charge for your work

23:44 The hidden world of government funding

28:32 What kind of coaches could look for funding?

35:10 Shifting into private coaching

40:45 Leads from your network

50:02 Program design

Resources:

From Passion To Profit Crash Course: https://jbhollows.kit.com/impacttoincome

LinkedIn: https://www.linkedin.com/in/jacqueline-hollows/

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

Email: [email protected]

Grow your business by hosting your own podcast: https://calendly.com/proclaimpodcasting/podcast-discovery-call

Starting a business rarely goes the way you expect - and the same is true for coaching.

Ben Larzabal, coach and entrepreneur who’s learned the hard way what really works (and what doesn’t), shares his 5 most impactful lessons for coaches.

From scraping together his first thousand dollars in a cramped apartment to scaling a business past $1.5M ARR, Ben distills his journey into five hard-won lessons every coach needs to hear.

These aren’t abstract theories - they’re raw stories of failure, clarity, and breakthrough that will help you avoid costly mistakes and speed up your growth.

If you’re serious about building a coaching business that actually lasts, this episode is for you.

In this episode:

0:00 Intro

1:26 Lesson 1: Show, Don't Tell

11:40 Lesson 2: Solve To Sell

18:45 Lesson 3: Gifts Over Skills

33:14 Lesson 4: Your Business Model Is Your Product

44:12 Interlude: The 5 Levels of Awareness for Marketing

59:47 Lesson 5: Look for Felt Problems

Resource:

Ben's LinkedIn: https://www.linkedin.com/in/ben-larzabal/

Rocky Garza: https://www.rockygarza.com/

Buy Back Your Time by Dan Martell: https://www.amazon.com/dp/059342297X

Simple Marketing for Smart People by Billy Broas: https://www.amazon.com/dp/B0D66H733H/

The Prosperous Coach by Chandler and Litvin: https://www.amazon.com/dp/1600250300/

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Book a call with me to see if a podcast could grow your business: https://calendly.com/proclaimpodcasting/podcast-discovery-call

Ben Harris is a fear coach.

After losing $40K in a crypto scam right after quitting his job to start his own business, he got to flex the "doing scary things" muscle big time.

He ended up turning this weird skill into a successful coaching business.

Now, he helps creators share their authentic voice with confidence, so they can actually build community, relationships, and make sales.

Listen in to hear how he got his start, how creators can start using their voices authentically, and how to make sales easier.

In This Episode:

0:00 Intro

1:25 The Fear Coach

6:32 $40K Crypto Scam

10:09 Potential catastrophic identity issues as a coach

15:51 Leads

21:47 Content and LIKING sales

30:11 Delivery

35:37 Challenges

40:31 Getting over the fear of posting

42:31 Coaching challenge: authentic content

Mentioned:

Ben Harris on LinkedIn: https://www.linkedin.com/in/the-fear-guy/

Authentic Voice Accelerator: https://www.feeling-free.com/authentic-voice-accelerator

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

Scott is a crazy impressive dude, and I have actually known about him for like 10 years...but only just met him.

He hosted a successful podcast (300-400k downloads/month) about building an Amazon FBA business.

That turned into a $1.7M business that he eventually walked away from (we get into WHY in this episode).

After a few more 6 figure at-bats that ultimately didn't excite him enough to keep going, he joined forces with his son to start Live Video School...and within 12 months, his brand new YT channel made him $115,000 and counting, AND built him an 11,000 person email list.

And he used none of his existing contacts/lists.

This is an insanely valuable episode where you'll get to see what it can look like to start a fun lifestyle coaching biz, all the way up to building a 7 figure empire.

In This Episode:

0:00 Intro

1:53 Why Scott left his 7 figure business

11:39 How to build a coaching business with an ORGANIC audience

17:07 How to build an audience (without going viral)

23:48 Scott's elite creator energy

27:47 Speed of implementation

31:22 Being a GUIDE not a GURU

34:33 Finding Your Offer

40:30 What to do once someone gives you their email

44:15 Sales process

46:22 Coaching Deliverables

48:39 Consistency and Content Strategy

Resources:

Live Video School: https://www.livevideoschool.com/

StoryBrand by Donald Miller: https://www.amazon.com/dp/B0CWTNCZCH/

Grow Your Business By Hosting Your Own Podcast (Free 45 Min Coaching Call): https://proclaimpodcasting.com/coach/

Caleb Whittle goes hard.

He quit his job as a CMO to become...

A fitness coach?

On LinkedIn?!

Seriously. And he's thriving.

He quit cold turkey without building this on the side a few months ago.

Now he's booking 4 figure clients with LinkedIn posts.

We talk about how he made the transition, nuts and bolts of his business, and get tactical on what it takes to be a great coach.

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Free 45 Minute Coaching Call: Learn how a podcast can help you make more sales and supercharge your authority (and network): ⁠https://proclaimpodcasting.com/coach/⁠

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In this episode:

0:00 Intro

0:56 CMO to Coach

4:10 How to quit your job and become a coach

6:41 Growing a fitness business on LinkedIn

13:45 Caleb's Launch Offer

19:00 Growing Without Being Overwhelmed

22:00 Lead gen

30:37 Sales process

34:31 The difference between a trainer versus a coach

37:41 The biggest challenge

39:45 Coaching through resistance and building discipline

48:26 The benefit of coming from the corporate world

Mentioned:

Caleb Whittle on LinkedIn: https://www.linkedin.com/in/calebwhittle/

This is exactly the type of episode I dreamed of when I launched The Real Coach Show.

Totally raw, full of numbers and details, and DEEP on the often unseen mental game of being a coach when life throws your haymakers.

Dylan Roos shares about navigating life with a super famous dad, selling a high-ticket program when he was terrified to charge that much, revamping the program and increasing the price to over $14,000, the entire breakdown of his business, and his unfiltered thoughts on what it's like to run a coaching business (including when your life is crumbling).

Insane value in this one. All coaches can benefit.

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Free 45 Minute Coaching Call: Learn how a podcast can help you make more sales and supercharge your authority (and network): https://proclaimpodcasting.com/coach/

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In this episode:

0:00 Intro

1:43 Coaching teens?!

5:07 Challenges of having a famous dad

11:44 Showing up when your personal life is rocked

15:47 How Dylan's selling to young men

24:29 Systematizing Leads and Sales

33:33 Organic

39:40 Dylan's Program

41:33 Hiring and Working on Your Own Stuff

58:17 How Dylan's rebuilding to $300K

Resources:

Dylan Roos on IG: https://www.instagram.com/dylan.roos

Dylan's Program: https://www.dylanrooscoaching.com/

Community for Parents: https://www.skool.com/sons-rise-community-5960/about

Community for Teens: https://www.skool.com/the-brotherhood-7732/about