Transitioning From An 8 Figure Business To Coaching with Russel Dubree [LNIM230]

What would make someone walk away from an eight-figure business to start over as a coach? In this episode, Mark interviews entrepreneur Russel Dubree about his journey from running a multimillion-dollar service company to launching a coaching practice. If you have ever thought about turning your business experience into a coaching business, this conversation will give you a realistic look at what that transition actually involves.

What You'll Learn in This Episode

• Why an eight-figure entrepreneur decided to sell his business and pivot to coaching
• How to identify your coaching niche based on your actual experience
• The two-step sales process Russel uses to sign coaching clients
• Why getting specific about who you help is the key to building a coaching business
• How to provide value in the sales process before anyone pays you a dollar
• The mindset shift required to go from running a large team to starting fresh

Episode Summary

Russel Dubree came out of the Air Force with an entrepreneurial drive. He and a business partner started building wedding websites, then pivoted to selling websites more broadly. Over the next decade and a half, they built a web design company generating just under ten million dollars in annual revenue with about forty team members.

Then Russel decided to sell the business.

The decision was not about the money or dissatisfaction. Russel had reached a point where he felt he had done everything he could in that space. He did not have a specific trade skill that locked him into web design. What he had was a passion for helping people and a desire for a new challenge. He quotes Ray Dalio: “Imagine that in order to have a great life you have to cross a dangerous jungle. You can stay safe where you are and have an ordinary life, or you can risk crossing the jungle to have a terrific life.”

That quote captures the essence of his pivot. Coaching was the natural next step because Russel had spent years mentoring people inside his own company. He had a long list of things business owners should and should not do, earned through real experience, not theory.

What helped him get traction early was getting specific about his niche. When he focused on people in his industry, he could rattle off insights and value immediately. That specificity also let him build a manageable list of ideal clients he could target directly.

Russel's sales process has two phases. Phase one is a relationship-building conversation, just getting to know each other. Phase two is an alignment session where he digs into the client's business and delivers two or three actionable perspectives. The potential client walks away with real value regardless of whether they hire him. It is a taste of what a long-term coaching relationship would look like.

His advice for anyone starting a coaching business: know exactly who you want to help, determine the specific problem you are uniquely qualified to solve, and remember that great coaching is not just about knowledge. It is about getting the best out of other people.

Key Takeaways

• Your business experience is a coaching asset, but only if you get specific about your niche
• A two-phase sales process (relationship first, alignment session second) builds trust before asking for a commitment
• Deliver genuine value during the sales process so prospects experience your coaching firsthand
• Building a targeted list of ideal clients is more effective than broad marketing when you are starting out
• The transition from operator to coach requires embracing a beginner mindset again
• Great coaching is about drawing the best out of people, not just sharing what you know

What's Changed Since This Episode

Mark recorded this conversation with Russel in early 2022, and the coaching industry has changed dramatically since then. The global coaching market was valued at over $6 billion in 2025, driven largely by the post-pandemic shift to remote work and online business. More people than ever are looking for coaches, and more experienced entrepreneurs are entering the coaching space.

Online coaching platforms have proliferated, making it easier to deliver coaching services at scale. Tools like Kajabi, Circle, Skool, and Mighty Networks let coaches combine courses, community, and one-on-one sessions in a single platform. AI tools are also entering the space. Some coaches use AI for client intake assessments, session notes, and follow-up content, though the human relationship remains the core of effective coaching.

The barrier to entry for coaching is lower than ever, which means differentiation matters more. Russel's advice about niching down is even more relevant in 2026. Generic “business coaching” is a crowded space. Coaches who bring specific industry experience and measurable results stand out. The market is rewarding coaches who can demonstrate real-world credibility, not just certifications.

One notable shift: group coaching and hybrid models (combining group sessions with limited one-on-one access) have become the dominant format for scaling a coaching business. Pure one-on-one coaching limits your income to your available hours, so most successful coaches build a model that includes courses, community, and selective private coaching.

Resources Mentioned

• Ray Dalio's Principles: Life and Work
• Performance Faction — Russel Dubree's coaching practice
• Russel Dubree on LinkedIn

Related Episodes

If you found this episode helpful, you might also enjoy:

• LNIM235 — How To Make Money Fast In 2022
• LNIM211 — Why Affiliate Marketing Is NOT Dead

Listen and Subscribe

Listen to Late Night Internet Marketing on Apple Podcasts, Spotify, or subscribe at latenightim.com/internet-marketing-podcast/. Have a question for Mark? Call the digital recorder at 214-444-8655 or drop a comment below.