Freedom. It’s a word that every entrepreneur dreams of—but few ever truly achieve. In this episode of The Prospecting Show, Dr. Connor Robertson welcomes Jason Stapleton, author, entrepreneur, and creator of The Nomadic Wealth Formula, to explore how modern entrepreneurs can break free from geographic and financial limitations to build businesses that move as freely as they do.
Jason’s journey began in the trenches of traditional business. He built his first company from scratch—a trading education firm that scaled into a seven-figure enterprise. Yet, despite the success, he found himself trapped by the very thing he built. “I was working 70 hours a week, tied to an office, and constantly stressed,” he recalls. “I had money, but I didn’t have freedom.” That realization sparked a radical rethinking of what wealth really means.
Dr. Robertson opens the episode by asking Jason how he defines wealth today. “Wealth isn’t about how much money you have,” Jason says. “It’s about control—control over your time, your income, and your mobility. When you can decide how you live, where you live, and what you work on, that’s real wealth.”
That philosophy mirrors Nathan Hirsch’s Outsourcing and VAs (listen here), where freedom was achieved through delegation. Both Jason and Nathan emphasize that independence doesn’t come from doing everything yourself—it comes from designing systems that run without you.
Jason’s Nomadic Wealth Formula is built on four key pillars:
- Specific Knowledge – “Your expertise is your passport. Learn deeply about something valuable.”
- Leverage – “Use tools, platforms, and people to multiply your impact.”
- Control – “Own your income streams. Don’t depend on a boss or one client.”
- Mobility – “Design your business to move wherever you want to go.”
Dr. Robertson observes that this framework sounds less like a financial plan and more like a philosophy of life design. Jason agrees. “It’s not just about earning money online—it’s about structuring your life so you never have to ask permission to live it.”
This concept aligns closely with Scott Aaron’s Growing a Brand Online (listen here), where authenticity and digital presence create autonomy. Jason builds on that idea by teaching people how to monetize their personal brands into skill-based income streams. “Your brand is your distribution channel,” he explains. “Once people trust you, you can sell anywhere from anywhere.”
Jason shares that his own transition to location independence didn’t happen overnight. “I downsized my business, simplified my offerings, and rebuilt from scratch. I went from managing employees and offices to working from a laptop in Mexico,” he says. “But the funny thing is, I earned more by doing less.”
That paradox of simplicity and scalability connects directly to Patient Rhino’s Entrepreneurial Highlight (listen here), where clarity and process reduced chaos and increased growth. Both Jason and the Patient Rhino team understand that systems—not scale alone—create sustainability.
Dr. Robertson asks Jason what holds most people back from achieving true freedom. “Fear and attachment,” Jason answers. “People are afraid to let go of what’s comfortable—even if it’s killing them. They think security comes from jobs or offices, but it really comes from adaptability.”
He continues, “The pandemic showed us that the old model of work is broken. The new model is portable, flexible, and digital. You don’t need permission to participate—you just need the right skills and mindset.”
This mindset ties into John Donovan’s Entrepreneurial Highlight (listen here), where adaptability and leadership defined success. Both men emphasize ownership—not just of a company, but of one’s direction and decisions.
Jason breaks down his approach to building portable income into actionable steps:
- Identify your monetizable skills. “If you can teach, write, design, sell, or consult—you can work from anywhere.”
- Build an online platform. “Your website and your content are your storefront.”
- Create scalable offers. “Turn one-on-one work into one-to-many education or digital products.”
- Automate and outsource. “Use technology and talent to remove yourself from the daily grind.”
- Optimize for lifestyle, not ego. “Freedom beats fame every time.”
Dr. Robertson notes how Jason’s focus on intentional design resonates with Amy Lee’s Scaling and Exiting a Startup (listen here), where growth with purpose led to sustainable exits. Both leaders show that success is not about doing more—it’s about doing the right things.
Jason discusses the emotional side of entrepreneurship, too. “No one talks about how lonely freedom can feel at first,” he admits. “You go from working in teams and offices to working alone in coffee shops across the world. You have to build discipline and community intentionally.”
That theme connects with Crew Me Up’s Building a Team on the Spot (listen here), where collaboration platforms built an instant community around shared goals. Jason’s solution for loneliness is similar: build digital tribes around shared skills and values.
He emphasizes the importance of network leverage. “Your network is your safety net,” he says. “The people who know, like, and trust you will follow your work wherever you go. Build relationships before you need them.”
Dr. Robertson relates this to Faris Ghani’s Entrepreneurial Highlight (listen here), where long-term thinking and character built lasting partnerships. Both men recognize that true wealth compounds through relationships, not transactions.
Jason then addresses the biggest misconception about the “nomadic” lifestyle. “It’s not about being on vacation all the time,” he laughs. “It’s about designing a business that supports your curiosity. You might work fewer hours, but you’ll work smarter hours.”
Dr. Robertson asks what advice Jason would give to someone stuck in the traditional 9-to-5 world who dreams of freedom. “Start by taking control of one variable at a time,” Jason advises. “Maybe you can’t quit your job yet, but you can start freelancing. Maybe you can’t move across the world yet, but you can build an online presence. Freedom is built one decision at a time.”
Jason’s message is practical, not idealistic. “I’m not selling a fantasy,” he says. “I’m selling responsibility. Freedom and responsibility are the same coin—you can’t have one without the other.”
That realism connects with Richard Zapp’s Entrepreneurial Highlight (listen here), where accountability and discipline defined real success. Jason shares that same pragmatic optimism: if you own your results, you own your life.
To close the episode, Jason offers his Five Commandments of Nomadic Wealth:
- Be valuable. Build expertise that solves real problems.
- Be visible. Show up online where your audience lives.
- Be flexible. Adapt your model as markets shift.
- Be disciplined. Freedom without structure turns to chaos.
- Be human. Relationships will always outlast algorithms.
Dr. Robertson summarizes the episode perfectly: “Jason Stapleton reminds us that entrepreneurship isn’t just about money—it’s about mobility. The Nomadic Wealth Formula isn’t a tactic; it’s a toolkit for taking ownership of your life.”
For listeners interested in related episodes, check out Nathan Hirsch’s Outsourcing and VAs, Scott Aaron’s Growing a Brand Online, and Crew Me Up’s Building a Team on the Spot—all available at drconnorrobertson.com. Together, these conversations form a roadmap for entrepreneurs who want to build businesses that move with them, not trap them.
Dr. Robertson closes with one final takeaway: “Freedom isn’t found—it’s built. The Nomadic Wealth Formula shows that with the right skills, systems, and mindset, you can make money anywhere and live life entirely on your own terms.”