Beyond the Game: Wealth Mastery for Athletes Kris Benson & Alec Ogletree

Join Kris Benson and Alec Ogletree as they interview former NFL offensive tackle Winston Justice who opens up about his journey from an 8-year playing career to financial advising. 
Winston discusses lessons from his NFL days, entrepreneurial experiences starting a coffee shop, and feeling unprepared transitioning to finance. Winston also shares advice on relationships. Don’t miss his insights on serving clients as an advisor today on managing life after the game!
Here are some power takeaways from today’s conversation:
[02:53] The importance of being present - both in family and career
[10:29] Pursuing off-field opportunities through entrepreneurship
[12:37] Starting a coffee shop business with his brother-in-law while still playing
[14:07] Lessons learned from his experience in venture capital investing
[28:45] The sacred bond of trust in financial advising
[31:37] Facing imposter syndrome in finance
[34:51] Building community beyond the game
Episode Highlights:
[10:29] Pursuing Off-Field Opportunities Through Entrepreneurship
Winston became interested in pursuing opportunities off the field due to the uncertainty of an NFL career. He shares how starting a coffee shop business with his brother-in-law while still playing gave him enjoyment in working with family. It also provided a learning experience in entrepreneurship, such as figuring out operations without prior knowledge. Winston then discusses his experience partnering with former NBA player Jamal Mashburn in a venture capital fund focused on healthcare and education. He learned that to truly add value as an investor, he needed experience operating a business to understand management teams beyond initial pitches. This experience informed his decision to later pursue public market investing.
[28:45] The Sacred Bond of Trust in Financial Advising
Winston gets that advising people on their money is deep. While folks talk freely about other stuff, finances are sensitive. Doesn't matter how much money someone's got - they stay guarded about it. He knows gaining clients' trust to help plan their future means really listening without judgment. Winston sees being a part of people's lives through this financial advising bond.
[31:37] Facing Imposter Syndrome in Finance
Winston reflects on feeling unprepared when he began his career in finance at Wells Fargo despite his accomplishments in football. He emphasizes feeling like an "imposter" when walking into rooms of highly educated professionals. However, he persisted because he knew what he wanted to do. Winston also emphasizes the importance of building relationships with teammates while playing to maintain community after retiring, when it can be harder due to life changes like family and location. Now as a financial advisor, Winston focuses on understanding his clients' goals and risk tolerance to create tailored portfolios.
[34:51] Building Community Beyond the Game
Winston understands the power of community both during and after an athletic career. Winston recognizes it can be difficult to recreate that same sense of belonging once sports are over. The business world doesn't provide the same built-in community that sports did. However, maintaining connections with former teammates and intentionally joining new communities, such as through his children's activities, has helped Winston feel less isolated in his post-playing life. He sees the importance of having a strong support system, especially when facing new challenges.
Resources Mentioned:
https://www.bernstein.com/our-team/locations/nashville/winston-justice.html 

In this episode, Kris Benson and Alec Ogletree are joined by former MLB pitchers Edwin Jackson and Brandon Beachy where they dish out some major league advice. 
With over 20 seasons of playing ball between them, EJ and Beachy share their experiences transitioning to the business world of franchising after hanging up their cleats. They've got some great advice on evaluating opportunities as franchising pros.
Tune in as they break down their transitions from baseball champs to owning franchises and consulting brands. You won't want to miss these players turning their game-winning skills into franchising success. 
Here are some power takeaways from today’s conversation:
[03:46] - The power of networking
[07:15] - Brandon’s career background
[10:19] - Limiting beliefs around investing in franchise
[20:08] - Mentorship, challenges in franchising, and the importance of asking for help
[24:26] - Franchising and evaluating financial viability
[29:46] - Evaluating franchise investments
[37:21] - Mitigating risks and applying due diligence
[41:34] - Franchising, brand selection, and relationship-building
 
Episode Highlights:
[03:46] The Power of Networking
Despite not knowing each other, Edwin connected with Raining Berries founder Bimal Bhojani at a wealth summit, where they discussed their acai bowl concept, Raining Berries. Intrigued, Edwin saw potential in franchising the brand through his fund LCP Concessions. His chance encounter led to an unexpected partnership, showing how industry events foster valuable connections.
[07:15] Brandon Beachy's Transition from Baseball to Business Ownership
After retiring from baseball, Brandon Beachy sought the entrepreneurial freedom and control over his schedule that playing sports lacked. However, with no business experience, he found franchising provided a proven system. A friend introduced Brandon to a home insulation franchise, allowing him to apply his strong work ethic. He now owns a thriving insulation franchise while also consulting others on franchise opportunities through his company What's Next Franchising. Brandon proves how franchising can smoothly help athletes transition into their next career chapter.
[10:19] Limiting Beliefs Around Investing in Franchise
One common limiting belief that prevents people from getting more involved in franchising is a lack of knowledge or understanding about what opportunities exist. Not being familiar with franchising as an option can act as a hurdle. Some may feel they aren't knowledgeable enough or don't have the right background, so they don't even consider it as a path. A fear of the unknown or not being an "expert" deters many from exploring franchising further. A lack of education about the industry and the support available is often the core reason this belief becomes a barrier.
[37:21] Doing Your Homework
Due diligence is key when evaluating any franchise opportunity in order to fully understand the risks involved. Edwin and Brandon stressed the importance of thorough research, including speaking with multiple existing franchise owners to learn about their experiences. While established franchise systems may have worked out many kinks, there are still adjustments to be made as brands evolve. Both emphasized the need for prospective franchisees to be prepared for potential bumps in the road and ensure the business model fits their goals, demographic focus and risk tolerance. Diligent upfront analysis is vital to making an informed investment decision.
Resources Mentioned:
https://www.rainingberries.com/franchising

Are you ready for an all-access pass into the high-stakes world of NFL player representation? This latest episode of Beyond the Game gives you a seat at the table with veteran agent David Canter. 
A 29-year NFL agent veteran, David has built superstar careers and negotiated contracts worth hundreds of millions. Listen in as he shares recruiting strategies and how agencies are courting prospects straight out of high school. David also opens up about the ups and downs of counseling clients through their NFL journeys and the importance he places on financial education and planning for life after football.
From negotiating big contracts to counseling players on their finances, David has seen and done it all in his time in the league. Tune in to hear his best stories and most valuable advice!
Here are some power takeaways from today’s conversation:
[06:30] David's unconventional path to becoming an agent
[15:00] Insider recruiting strategies for signing top prospects
[26:00] Challenges of financial literacy for young NFL players
[38:00] The importance of mentorship between veteran and rookie players
[49:00] David's advice for maximizing NFL career earnings
[1:01:00] Life after football and planning for long-term financial stability
 
Episode Highlights:
[15:00] The Evolving Landscape of Recruiting Top High School Prospects
With new rules allowing players to hire agents straight out of high school, David has seen a shift in how agencies scout and woo young talent. He explains that it has become almost like a full-time job to stay on top of the newest up-and-coming stars. David details some of the new tactics being used, like following top recruits on social media from a young age and then traveling to all of their games and events. Agencies are also increasingly relying on recruiters in key areas to build local connections and influence. It's become a highly competitive process to sign the best young players even before they step on a college campus.
[26:00] Challenges of Financial Literacy For Young NFL Players
David recounts having to teach a veteran player how to write a check, despite being in the league for several years. Many players come into the NFL without ever having managed large sums of money. Simple tasks like paying bills and understanding tax documentation can be foreign concepts. While knowledge has increased over time, David still finds that financial education is needed throughout a player's career. He stresses that agents must make sure clients understand basic financial matters in order to set them up for long-term success beyond football.
[49:00] David's Advice for Maximizing NFL Career Earnings
Avoid distractions and live below your means. Treat every season like it's your last chance to cash in on their football skills. Immerse yourself fully in your training to stand out to teams. Negotiate smart contracts that provide security upfront rather than gambling on future earning potential. Finally, take care of your mental and physical health so you can have as long of a career as possible in the league.
Resources Mentioned:
Football GSE Worldwide
Follow David on Instagram and X

After his NFL dreams were dashed by injury, former Purdue football star Joe Holland chose to channel his competitive spirit into building a thriving dental practice. In this episode, Joe opens up about his pivot from medicine to dentistry in pursuit of practice ownership and learning to lead employees with no business experience. 
Now the owner of multiple offices, Joe shares his story of turning adversity into success through strategic marketing moves worthy of a game day playbook. Learn from how Joe's grit and determination helped him overcome obstacles to build his own "dental dynasty."
Here are some power takeaways from today’s conversation:
[00:41] Joe’s road to football and dentistry
[15:22] Leveraging athletic career for professional success
[21:59] How athletic background can lead to business success
[25:27] Why dentists make attractive lenders 
[26:44] Buying a dental practice and transitioning ownership 
[31:15] Buying and selling dental practices and competition from private equity
[45:44] Leadership and management in a dental practice
[56:17] Dentistry, growth, and future plans
[58:21] Financial literacy and investment principles for former NFL players
 
Episode Highlights:
[21:59] How Athletic Background Can Lead to Business Success
Joe believes his athletic background helped set him up for business success. Playing college and pro football built his resilience, work ethic, and confidence. Being voted captain his senior year taught leadership skills. Sports fostered determination and competitiveness, giving him the mindset to take risks like purchasing a dental practice. His athletic experiences developed qualities that translated well to his post-football professional career.
[25:27] Why Dentists Make Attractive Lenders
Joe leveraged one aspect of being a dentist to his advantage when purchasing his first dental practice - he realized that dentists make very attractive lenders. As a low-risk profession with stable incomes, dentists have low default rates on loans. Joe was able to use this knowledge of how appealing dentists are to lenders in order to secure financing for his practice purchase, recognizing it as one of the benefits of entering this particular career field.
[26:44] Buying a Dental Practice and Transitioning Ownership
Joe took an unconventional approach to buying his first dental practice: sending notes to elderly patients resembling retired players. This connected him with a selling dentist. However, the shortened transition period caused patient confusion, as Joe realized he needed longer overlap to smoothly hand over the established but declining business. It was a valuable learning experience for effectively transitioning practice ownership.
[45:44] Leadership and Management in a Dental Practice
Joe realized he overestimated how his leadership skills from football would directly apply to managing a dental practice team. He learned it was important to get to know employees personally outside of work to understand their individual communication preferences and learning styles. Only then could Joe tailor his leadership approach and set clear expectations to effectively motivate each person. Developing personal relationships with staff helped Joe build cohesion and improved his ability to lead the team towards shared goals.

Get your game plan from a true Beyond the Game master!
Today, Kris Benson and Alec Ogletree sit down with former NFL star Cliff Avril to discuss his journey from football to real estate investing. Over the course of his career, Cliff learned valuable lessons about financial literacy, accountability, and team building - skills he now applies to growing his real estate business. 
Tune in to hear Cliff share lessons from the gridiron and insights into his multifamily and luxury spec home ventures.
Here are some power takeaways from today’s conversation:
[02:35] Excuses are monuments of nothingness.
[08:42] The importance of financial literacy
[16:22] Translating your lessons and skills from football to business
[19:17] Paying for convenience
[28:50] Networking, ego, and time management for athletes and entrepreneurs
[36:05] Cliff’s real estate journey
[39:48] Understanding value add real estate investing
[44:35] Cliff’s business structure and diving into the luxury market
[51:41] Cliff Avril Family Foundation
 
Episode Highlights:
[02:37] Beyond Excuses: Achieving Success By Taking Accountability
Cliff lives by the quote: “Excuses are monuments of nothingness.” Those who specialize in them rarely amount to anything. People who rely on excuses to justify their shortcomings or lack of achievement will struggle to accomplish meaningful goals or have lasting success. The quote serves as a reminder to avoid complacency and instead focus our energy on finding solutions rather than making excuses.
[08:42] The Importance of Financial Literacy
When Cliff received his first signing bonus, he was surprised to learn through a conversation with his agent that most of the money went to taxes, a concept he had never been taught. This wake-up call drove Cliff's passion for educating himself and others on financial principles. He now ensures his own children understand these lessons from a young age to avoid the same surprises. Cliff's journey highlights just how critical financial literacy is, especially for athletes receiving large salaries.
[39:48] Understanding Value Add Real Estate Investing
Value add real estate investing is a strategy that focuses on renovating or redeveloping properties in order to increase their value beyond typical market appreciation. Cliff employs this tactic in his real estate business. He looks for distressed properties that he can purchase at a discount, and then completely renovates or rehabs the building to modern, higher-end specifications. This "forces'' appreciation in the property immediately through the renovation work. It allows him to buy a property for one price, put additional money into improvements, and sell or hold it at a much higher value once the project is complete. This value add approach generates outsized returns for Cliff compared to simply buying and holding properties for long-term appreciation.
Resources Mentioned:
Cliff Avril Family Foundation
Rich Dad Poor Dad by Robert Kiyosaki
Integrity By Dr. Henry Cloud

From the pitcher's mound to the boardroom - don't miss Brandon Beachy's story of resilience and reinvention on this latest episode!
Kris Benson and Alec Ogletree sit down with former MLB pitcher Brandon Beachy to discuss his journey from professional baseball to franchise business owner. After nearly a decade at baseball's highest level, multiple injuries forced this former MLB pitcher to face the hard truth that his playing days were over. But Brandon was just getting warmed up. 
Tune in to hear how he took the grit and determination that led to success on the mound and channeled it into building a thriving franchise business from scratch. Brandon shares powerful lessons on overcoming adversity and reinventing your career even when the odds seem stacked against you. 
Here are some power takeaways from today’s conversation:
[03:00] Transferable skills from baseball to business
[11:54] Brandon’s career background
[20:00] Lessons from Chipper Jones
[30:56] Brandon’s injury experience
[37:03] How he got into a franchising business
[46:50] Business growth and scaling
[47:20] Learning how wealthy people leverage debt
[54:20] Finding the right business
Episode Highlights:
[03:00] Transferable Skills from the Ballfield to the Boardroom
Brandon talks about how baseball taught him to be resilient in the face of failure, as even the best hitters fail more often than not. Dealing with injuries and setbacks also helped build his determination to keep working hard no matter the obstacles. Other skills like self-motivation, leadership abilities and teamwork mentality were all attributes that served him well in running a successful franchise business. According to Brandon, these "intangible" traits learned from sports ended up being extremely applicable in the entrepreneurial world.
[20:00] Lessons From Chipper Jones
Chipper Jones helped Brandon realize that as a pitcher, he didn't need to be perfect against every hitter, but there were one or two in each lineup that had the ability to truly anticipate his pitches based on how he was pitching others. Chipper taught Brandon that there were hitters who were studying him and could see what he was doing to other batters in order to get ahead. This insight changed Brandon's approach and mindset on the mound.
[54:20] Working Backwards: Brandon's Methodology for Finding the Right Business Fit
Brandon discusses the methodology he uses in his franchise consulting work. He emphasizes the importance of focusing first on a client's goals, motivations and desired lifestyle or end destination, rather than jumping straight into exploring specific business concepts. By working backwards from where they want to be, he can better find an opportunity that truly "fits" what the client is looking for in both the short and long-term. This intentional approach allows the business to complement their lifestyle vision, rather than forcing the client's priorities to conform to whatever opportunity comes first.
Resources Mentioned:
www.whatsnextfranchising.com