After 20 years in medical sales, Josh embraced creative real estate for freedom and financial growth. This interview covers his journey from skepticism to success, sharing lessons on avoiding mistakes, closing deals, and reaching $500K in net profits. His story proves how taking action can change your future!

In this inspiring interview, you'll discover:

• How Josh transitioned from a 20-year career in medical sales to real estate investing.
• The personal and professional growth he gained through his journey.
• The flexibility and freedom that came with his new career.
• The invaluable support from the Freedom Mentor team.
• The importance of taking risks and problem-solving in real estate.
• How having a supportive spouse can impact success.
• Why stepping out of your comfort zone can lead to life-changing opportunities.

Career Shift: From Medical Sales to Entrepreneurship

Josh’s transition from medical sales to real estate investing was not a straightforward path. After spending 20 years in medical sales, he found himself consulting for a friend’s business. That initial step into entrepreneurship sparked something within him. His first attempt—selling products on Amazon—quickly failed, but it gave him a taste of the freedom that comes with building something on your own. From that moment, he knew a traditional 9-to-5 job was no longer an option. Real estate had always intrigued him, but until that point, it had never been more than an interest. Now, he was ready to make a move. That decision ultimately led him to discover Freedom Mentor and embark on a life-changing journey in creative real estate.

Finding the Right Mentorship

Years ago, Josh had read a Robert Kiyosaki book about real estate, but at the time, he hadn't pursued it further. With renewed curiosity, he researched online and came across Phil’s videos, which resonated with him instantly. Unlike other self-proclaimed “gurus” in the real estate space, Phil’s approach felt genuine, and the authenticity of Freedom Mentor stood out. Josh decided to take action, reaching out via the website to explore the program. However, coming from a sales background, he remained skeptical—was this too good to be true?

Overcoming Skepticism

One of Josh’s concerns when joining Freedom Mentor was whether it was just a well-crafted sales pitch. Having worked in sales for two decades, he knew how to spot a scripted approach versus a real opportunity. However, his doubts quickly faded when he experienced real-time engagement with Phil, Brian, and the Freedom Mentor team. Instead of being sold something, he was mentored in an authentic way. The personalized one-on-one feedback, direct communication, and structured guidance made all the difference in helping him move forward with confidence.

Experiencing the Program: Genuine Support

Josh had a major hesitation when joining Freedom Mentor—his risk-averse nature. While creative real estate seemed exciting, the reality of talking to sellers, signing contracts, and committing to deals was daunting. As he put it, "People often think, ‘Oh, this sounds great! I’m going to learn real estate and how to do it. But when it comes to the rubber meeting the road, and you actually have to go out there and actually execute on a property, it helps to have the best team possible".

What made the difference for Josh was the real-time support available in those critical moments. Having access to mentors who could provide immediate guidance ensured that he wasn’t left to navigate challenges alone. "Having the right team behind you—the best possible mentorship—is critical," Josh emphasized. "And that support doesn’t come from just watching videos. It comes from talking to someone in real time, being able to reach out and say, ‘Hey, I'm dealing with this—what do I do?’"

Building Confidence Through Support

Josh quickly realized that the most valuable part of the program wasn’t just the knowledge—it was the people behind it. The Freedom Mentor team was hands-on, and he experienced firsthand how vital direct mentorship was in building confidence as an investor. "You don’t realize how scary it is until your first deal is in front of you, and suddenly, it’s time to apply everything you’ve learned," he shared. At that moment, having the Freedom Mentor team behind him made all the difference. He wasn’t just taught real estate principles—he was guided through the process in a way that allowed him to make decisions he felt confident about.

The Power of Patience and Understanding

Beyond technical knowledge, Josh deeply appreciated the patience and understanding of the mentors. During high-stress moments, having someone offer calm, level-headed advice made a huge impact. "One thing I appreciated was the patience and understanding of the mentors, especially Brian—who, honestly, has the most comforting ‘late-night radio voice’ I’ve ever heard," he joked. "When you're stressed, having someone calmly say, ‘Hey, it’s going to be okay. I know they tried to take you for five grand—here’s what to do next,’ really makes a difference." That kind of personalized support turned nerve-wracking situations into manageable experiences.

Learning to Avoid Bad Deals

Most people focus on finding great deals, but Josh quickly learned that avoiding bad deals was just as valuable. As Phil often says, “Sometimes, it’s the deals you don’t do that matter most.” Through mentorship, Josh developed the ability to analyze a deal before making a costly mistake. Talking through a potential deal helped him recognize flaws, tight margins, and hidden risks. He credits Freedom Mentor with saving him thousands by steering him away from bad investments—something that every new investor needs to learn early.

“I can’t tell you how many heartaches you guys (the Freedom Mentor team) saved me from by just not doing a bad deal.”

Memorable Creative Deals

Josh’s first deal remains his most memorable—not necessarily for the profit but for the experience itself. He can still recall every conversation with the seller, every detail of the house layout, because that moment marked a turning point in his journey. It was the moment when he had to apply everything he learned, take action, and make the deal happen.

The World War II-Era Sewer Problem

Another standout deal involved a property with a unique sewer connection dating back to World War II. Instead of an actual pipe, the sewer was connected with cardboard and tar, a makeshift solution used during wartime due to steel shortages. To make things more complicated, the property sat on a cut-through road, which impacted valuation and buyer appeal. Josh worked with Phil and Brian to navigate these challenges, ultimately turning it into a profitable flip that earned him $65,000. The experience taught him an invaluable lesson—always scope the pipes before investing in a property.

The Biggest Mistake Investors Make

According to Josh, the biggest mistake an investor can make is being too risk-averse to take action. Creative real estate is about problem-solving, and investors must be willing to navigate challenges—whether it’s difficult contractors, unpredictable sellers, or unforeseen issues.

Learning to Manage Risk

If fear paralyzes you from making a move, you’ll miss opportunities. The Freedom Mentor program played a vital role for Josh in mitigating risk, ensuring he had the support and knowledge needed to make smart decisions with confidence.

"Where Freedom Mentor helps is mitigating that risk. Having somebody that's got your back and working through those risk factors."

Graduating with $500,000 in Net Profits

Reaching $500,000 in net profits after all expenses was a surreal moment for Josh. For him, it felt better than graduating college because it proved something incredible—he had successfully transacted $500,000 in real estate, something that once felt out of reach. One of the aspects Josh appreciated about Freedom Mentor was the profit-share model, which kept him focused and motivated. Tracking progress daily made the milestone tangible, and reaching it reinforced that all the work had paid off.

The Role of Family in Real Estate

Early on, Josh made some bold financial moves, including divesting his 401(k) and selling his Myrtle Beach property to fund his transition into real estate. Fortunately, his wife was supportive, which he considers critical for anyone taking a similar path. Phil often emphasizes the importance of having a spouse on board, and Josh echoes that sentiment. The journey wasn't just about making money—it was about personal growth, gaining freedom, and creating a future for his family.

The Freedom of Creative Real Estate Investing

One of the biggest changes in Josh’s life is the freedom he now has. He wakes up each morning and makes breakfast for his kids, something he had always wanted to do but never had the flexibility for. The ability to step away from work for spontaneous moments—like taking his son on a bike ride in the middle of the day—is what defines the success he has achieved. Real estate offers the ability to work as hard as you want while deciding when to take breaks and prioritize family. Josh is no longer tied to someone else’s schedule. He decides how he spends his time, which, to him, is the most valuable part of his journey.

Personal Growth Beyond Creative Real Estate

Creative real estate doesn’t just challenge investors financially—it transforms them personally. The process of learning, adapting, and making critical decisions forces personal growth in ways that extend beyond business. The ability to problem-solve, take risks, and navigate challenges impacts every aspect of life, including relationships, family, and overall mindset. For Josh, this journey has meant more than just making money. The lessons he has learned as a real estate investor have shaped his approach to business, family, and even parenting. The ability to think strategically, remain adaptable, and embrace uncertainty has translated into a broader perspective on life.

"Looking back, it has been life-changing—I can’t imagine not doing this—what a missed opportunity if I had not done it. It's been phenomenal."

Every Successful Creative Real Estate Investor Has a Mentor

If you’re ready to take control of your financial future and build a life of freedom, consider applying to the Freedom Mentor apprentice program. The skills and confidence you’ll gain can become your foundation for success: Freedom Mentor Apprentice Program.

If you have questions for us, text FREEDOM to 305-315-8030 or post a comment below.