Private Coaching is Currently Full
Stephen only works with a select group of business owners at this level.
Our coaches built themselves out of full-time jobs so they could help others do the same—without filling up their own calendars again.
Why There Are Limited Spots
Stephen spends 45 minutes a week on his 88-franchise business. Andrew built and led companies to billion-dollar scale, then stepped away. They didn't build themselves out of full-time jobs just to create new ones coaching.
The philosophy is simple:
Lifestyle first. Business second. Build something that funds the life you want, then enjoy that life.
Quality over quantity
Each client gets Stephen's full attention. Most business coaches will take on 50, 100, even 200 clients. That's a business model, not a lifestyle.
Lifestyle protection
Stephen won't sacrifice his freedom to scale coaching. What good is building a $10M coaching business if you're trapped working 80-hour weeks again?
Results matter more than revenue
Better outcomes come from focused attention. The demand speaks for itself: 47 applications for the last opening.
What This Means for You: When a spot opens up (usually 2-3 times per year), you get access to someone who's actually living the life you're trying to build.
When a Spot Opens, Here's What You Get
Private Coaching Package
For the handful of dedicated business owners serious about building freedom, not just more revenue
Everything in Elite Program
- Weekly education sessions and Q&A with the group
- Full Black Diamond System implementation
- Community of 100+ business owners
- Quarterly strategic and social events
Plus Your Private Benefits:
2-4 Private Strategy Sessions Monthly
- 60-minute sessions focused entirely on your business
- Direct access to Stephen's 20+ years of experience
- Custom solutions, not generic advice
Between-Session Access
- Priority response to urgent questions
- Strategic guidance when opportunities arise
- Support for time-sensitive decisions
Custom Business Roadmap
- Personalized plan based on your specific goals
- Industry-specific strategies and network introductions
- Accelerated timeline designed around your lifestyle goals
The Philosophy: This isn't about scaling coaching revenue. It's about helping a select group of business owners build the freedom Stephen and Andrew have achieved—then protecting that freedom by not over-committing.
Who You're Working With
Stephen O'Sullivan
Started with a failing driving school in 2011. Built it into 88 franchises across 3 states. More importantly: appointed a general manager and stepped back completely.
Now spends 45 minutes a week on a multi-million dollar business. The rest of his time? Fishing on Sydney Harbour, skiing worldwide, actually taking holidays.
Stephen's Week
What This Means for You
- He's built exactly what you want to build
- He understands the psychology of letting go
- He knows how to structure teams for independence
- He's navigated every growth challenge you'll face
The Network Effect
20+ years building businesses means Stephen knows everyone. Investors, advisors, potential partners, acquisition opportunities—access matters at your level.
Here's What Your Runway Might Look Like
Remember: 1-on-1 coaching is bespoke and tailored specifically to you. This is just an example of how we typically structure the journey.
Month 1: Strategic Assessment
- Deep dive into your business, goals, and challenges
- Custom implementation plan development
- Priority area identification and timeline
Month 2-3: Rapid Implementation
- 2-4 calls per month focused on execution
- Real-time strategy adjustments
- Priority access for urgent decisions
Month 4-6: Scale and Optimize
- Growth strategy refinement
- Advanced systems implementation
- Leadership development and team building
Month 6+: Strategic Partnership
- Ongoing strategic advisor relationship
- High-level business decisions support
- Network introductions and opportunities
While You Wait: Elite is Available Now
Since private coaching is full, most business owners join Elite and get 80% of the value immediately.
Elite Program: $400/week
- Weekly sessions with Stephen and the group
- Complete Black Diamond System implementation
- Community of 100+ business owners
- Quarterly events and full system access
The Math
Elite costs $1,600/month vs Private at $5,000/month.
For most business owners, Elite delivers the transformation they need. Private coaching is for the handful who want Stephen's undivided attention and have complex strategic challenges that require it.
Consider This
Many of our most successful members started with Elite. Kane went from overwhelmed and overworked to clear plan and golf every week. Leeza won Entrepreneur of the Year in 8 months.
The truth? The system works whether you're in Elite or Private. The difference is speed and personal attention, not results.
This Isn't for Everyone
Who We Work With
- Established businesses ready for strategic growth
- Owners who implement quickly and decisively
- Leaders who value expert guidance
- Businesses with systems foundation in place
Who This Isn't For
- Startups or businesses under $1M revenue
- Owners looking for basic business education
- Those wanting to DIY everything
- Businesses without foundation systems
The Application Process
Application Form
Tell us about your business and goals
Strategy Call
30-minute discussion with Stephen
Mutual Fit Assessment
Ensure we're right for each other
Onboarding
Custom plan development and kickoff
Frequently Asked Questions
Elite is group coaching with proven systems. Private coaching is custom strategy with direct access to Stephen. Think of it as having a strategic advisor vs attending business school.
6 months. Real transformation takes time, and we want to ensure you get results.
Yes, though most private clients prefer to continue the relationship due to the strategic value.
Usually within 2 weeks of application approval. Stephen only works with a limited number of private clients.
That's exactly why private coaching exists. Stephen has worked across dozens of industries and business models.
Just monthly fees. Stephen may discuss partnership opportunities separately if there's mutual interest.
Stephen has facilitated multiple successful exits and can guide the process or make introductions to qualified buyers/advisors.
Your Move
Quick Reality Check
Stephen's last private coaching opening had 47 business owners apply for 1 spot. The wait can be 6-18 months.
Elite is available now, delivers real results, and costs 70% less. Most business owners get everything they need from Elite.