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