Ex NFL Player Turned a Real Estate Superstar with Dean Rogers

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Are you curious about how a former NFL player turned the tables and found extraordinary success in the real estate investing world? With so many professional athletes facing financial challenges after their careers, Dean’s story is a refreshing departure from the norm. He not only managed to avoid the pitfalls but soared to new heights by flipping and wholesaling over 500 houses and amassing an eight-figure rental portfolio. If you want to hear the secrets of Dean’s spectacular transformation and gain insights into real estate investing, this episode is an absolute must-listen! Get ready to be inspired and empowered as we explore the game-changing moves of an NFL star in the world of property investment. 

Guest: Dean Rogers is a former NFL player who made a bold decision to shift from the football field to the dynamic world of real estate. With a successful business in California, Dean has flipped and wholesaled over 500 houses, amassing an impressive eight-figure rental portfolio. Beyond his achievements, Dean’s true passion lies in helping others learn the secrets of building wealth and gaining financial freedom through real estate. Prepare to be inspired as he shares his journey, wisdom, and dedication to transforming lives in the lucrative world of property investment. 

[00:00] In this episode, Dean shares his remarkable journey and reveals how he’s helping others build wealth and freedom through real estate. 

[02:00] Self-Discovery After NFL: 

  • The passion and dedication that drive athletes to achieve greatness in their respective sports are unparalleled.

  • They invest years of hard work, discipline, and consistent effort to reach the pinnacle of success, and it becomes a dream life that many can only imagine. However, all good things eventually come to an end, and for athletes, that can be a daunting reality.
  • When their sports career reaches its conclusion, athletes face a profound identity crisis.  Suddenly, they find themselves without the game that defined them for so long. This transition is emotionally and mentally challenging. They must redefine themselves and find a new vehicle to support their lifestyle and passion.
  • It’s essential to recognize that athletes possess valuable qualities like hard work, discipline, and leadership, but they may lack the tangible skills necessary to venture into new domains.
  • Learning new skills and understanding aspects of business, such as sales, finances, and entrepreneurship, becomes crucial for a successful transition.

  • Navigating this post-athletic journey requires support, education, and mentorship. Athletes who seek guidance and actively develop new skills are more likely to succeed beyond their sports careers.

  • It’s crucial to help athletes understand that their potential extends beyond the field and that they can channel their passion and dedication into different avenues for continued success. 

[05:41] Helpful Lessons Learnt As An Athlete:

  • The lessons learned from sports are invaluable and can shape one’s character and success in various aspects of life, including entrepreneurship.

  • Sports teach us to deal with adversity, handle pressure, and persevere when faced with challenges. The experiences of pushing through tough situations, receiving criticism, and working collaboratively with others build resilience and mental fortitude.
  • Entrepreneurs often encounter setbacks and failures in their journey, but the ability to face these difficulties head-on and take responsibility for their decisions is essential.

  • The mental toughness developed through sports enables entrepreneurs to look themselves in the mirror, acknowledge the hardships, and find the determination to push through.
  • Translating these skills to real-life scenarios helps entrepreneurs stay composed and execute their plans even when facing distractions and challenges.
  • Incorporating the teachings of sports into everyday life is a powerful way to nurture a resilient and determined mindset, fostering the traits necessary for success in entrepreneurship and beyond. 

[09:08] The Ideal Way Of Parenting:

  • It’s essential to strike that fine balance between encouraging and supporting your children’s interests without forcing them into something they don’t enjoy.

  • The key is to observe and understand what truly motivates and excites them. When children are genuinely passionate about something, they become more engaged and self-motivated to pursue it.
  • As a parent, you can expose your children to various activities and sports to see what resonates with them. By providing opportunities for exploration, they can discover their interests and passions on their own terms.

  • It’s crucial to listen to their feedback and take note of what they enjoy most. It allows you to bond with them, share their achievements, and witness their growth firsthand. At the same time, it’s vital to respect their autonomy and let them explore their interests independently.
  • When children discover their own passions and feel supported in pursuing them, they are more likely to develop self-confidence and motivation. As parents, your role is to be their cheerleader, guiding and supporting them on their journey of exploration and growth.

[12:31] Dean’s NFL Journey:

  • My journey to the NFL was a mix of uncertainty and determination. Although I always believed it was attainable, I faced challenges due to being under-recruited during my high school years.

  • Despite setting records as a running back, I didn’t receive as much attention from colleges as I had hoped. Eventually, I ended up at UC Davis, a smaller football school in California known for producing NFL quarterbacks and tight ends.
  • Playing as a tight end, I continued to excel and gained recognition, catching the attention of NFL scouts. Still, I felt like I wasn’t at a big-name school and didn’t receive the same level of attention as some other players. However, one day, everything changed. I received the call I had been dreaming of – an opportunity to join the Chargers.
  • Overnight, my life transformed. From living at my parents’ house to signing a three-year, seven-figure contract with the team, it was like a movie. Stepping into the Chargers’ world, I was welcomed into the company of football superstars like Philip Rivers and Antonio Gates. The experience was surreal and thrilling.
  • Practices were intense, like something straight out of the TV shows “Ballers” and “Hard Knocks.” The competitiveness among players was fierce, and every moment counted. Yet, there was also the glamorous side, where fans screamed our names, seeking autographs and attention.

[19:27] Putting His Health Before His Passion:

  • As a fullback, the collisions were brutal, and I knew that my life expectancy was at risk if I continued in that position. It was like running at full speed into a brick wall repeatedly, with no reprieve.

  • The pressure to be effective in my role required going all out, and the narrow gaps between giant linemen meant using my head for blocking. This continuous strain was taking a toll on my brain cells, and I realized that I needed to make a difficult decision for my long-term well-being.
  • Ultimately, the immense physical toll and potential consequences on my health led me to choose a different path.

  • Though my NFL career was shorter than anticipated, the experience taught me valuable life lessons about perseverance, sacrifice, and making the right choices for one’s future.

  • While the NFL experience brought incredible moments, it also demanded tough decisions about one’s future and well-being. The physical and mental toll that comes with playing professional sports is not always apparent to those on the outside, and it’s crucial for athletes to prioritize their health and make informed choices about their careers.

[28:00] Getting Into Real Estate:

  • After my first year in the NFL, I realized that the money wasn’t going to sustain the lifestyle I had envisioned. I received a mere $2,000 pay raise, which left me feeling discouraged and unsure about my financial future.

  • Back in my small 424-square-foot studio in San Francisco, I started to reflect on what other career paths I might enjoy. I remembered my interest in real estate from watching HGTV shows with my parents, so I decided to explore that avenue.
  • I learned about wholesaling, a strategy where you find motivated sellers who need to sell their property quickly, get the property under contract, and then sell it to another investor for a profit.

  • I didn’t let self-doubt hold me back; I took action and completed my first deal in just three months. This success gave me the confidence that real estate could be the vehicle to achieve the dream life I had envisioned during my time in the NFL.
  • From that point on, I embraced the real estate journey with unwavering determination. Sure, there were failures along the way, mostly due to my eagerness to rush into deals and force success. But my persistence paid off, and I’ve now been involved in nearly 600 deals, including fixing and flipping houses, wholesaling properties, and building a rental portfolio worth around $10 million.
  • Today, I run my real estate business virtually from San Diego, while my team of eight operates in central California, where I grew up.

[36:46] The Definition Of Success:

  • While the philosophy of being obsessed to achieve greatness has merit, it’s crucial to avoid neglecting important life moments with family. Having a support system that encourages balance is essential, and delegating tasks to build a reliable team is key to achieving real success and freedom as a business owner.
  • For me, a perfect day involves starting with some work-related tasks, ensuring the team is motivated and on track. After that, I prioritize exercise and a healthy diet to keep my body feeling good. Spending quality time with my kids, enjoying outdoor activities like playing sports or exploring new adventures, and traveling the world are what real success looks like to me.
  • Regarding my real estate ventures, my active business includes wholesaling and fix-and-flips, and we’re achieving exciting goals, completing about 100 deals annually. 
  • I’m always eager to connect with others, as I believe in the power of relationships and the opportunities they bring. 

[40:36] Learn More About Dean Rogers:



Igor Kheifets is an amazon best-selling author of the List Building Lifestyle: Confessions of an Email Millionaire.

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