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Playbooks & Portfolios

Author: Sean and Liam Clifford

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This podcast is a real-time look at what happens when two NFL athletes build beyond football.

Hosted by brothers Sean and Liam Clifford, the show documents the journey from locker rooms to boardrooms — covering football, business, investing, relationships, and the lessons learned along the way.

You’ll hear:

  • behind-the-scenes of NFL life
  • building a venture fund and athlete investment network
  • conversations around deals, failures, and opportunities
  • how athletes are becoming operators, investors, and founders

Nothing scripted. Nothing polished. Just the real process of building while still in the game.

25 Episodes
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In this episode, we welcome on Bengals Center Ted Karras who shares his journey from a football career to impactful community initiatives through his Cincy Hat foundation. He discusses the importance of teamwork, advocacy for adults with disabilities, and his aspirations for the future.Chapters00:00 The Hat That Changed Lives10:50 From Football to Philanthropy18:00 Scaling Success with Cincy Hat19:01 Recognition and Advocacy: Walter Payton Man of the Year23:35 Future Aspirations Beyond FootballFollow us on Instagram, X, Tiktok, and YouTube!@Playbooks_Portfolios
The conversation features Kurt Benkert, a former NFL quarterback, discussing his journey from high school football to the NFL, his experiences with various teams, and his transition into content creation and gaming. He shares insights on the evolving landscape of college football, the importance of NIL, and the lessons learned from playing alongside legends like Aaron Rodgers. In this conversation, Kurt Benkert shares his journey from being an NFL quarterback to becoming a successful entrepreneur, emphasizing the importance of social media and personal branding in his transition. He discusses the challenges of leaving football behind, the growth of his business Dime Lab, and his vision for the future.Chapters00:00 Kurt Benkert's Journey to the NFL03:33 The Transfer Portal and Its Implications08:55 Navigating the NFL Landscape15:00 Learning from Legends: Aaron Rodgers19:55 The Rise of Content Creation23:38 From NFL to Entrepreneurial Journey26:00 Navigating Life After Football36:09 Building a Brand with Dime Lab39:52 Future Aspirations and Goals45:50 Leadership and Team Dynamics
The conversation explores the evolving landscape of sports broadcasting, private equity in sports, and the impact of sports betting on team valuations. The hosts discuss the financial implications of these trends and their potential future developments. The conversation delves into the evolving landscape of college sports, particularly focusing on NIL deals, player transfers, and the need for athlete representation in decision-making processes. We also take a dive down memory lane as Sean and Liam talk their journey to Penn State. TakeawaysSports broadcasting salaries skyrocketingPrivate equity reshaping team valuations NIL deals are transforming college sportsAthlete representation is crucialChapters00:00 The Rise of Sports Broadcasting Salaries12:03 Private Equity's Influence on Sports25:26 The Boom of Sports Betting and Its Implications33:39 NIL and the Future of College Sports34:08 The Impact of NIL Deals36:44 Transfer Portal Dynamics39:57 The Value of Scholarships44:38 Athlete Representation in Decision-Making51:43 Key Conversations for College Athletes
We want to give a HUGE thank you to Bernie Kosar joins to share his remarkable journey from exploiting an NFL loophole to navigating investments and business ventures. He delves into his health and wellness journey, emphasizing the importance of resilience and the #UMatter movement.Please like, subscribe, repost and follow us on all our socials!@Playbooks_Portfolios
The Clifford Brothers cover the topics of NFL's venture fund, Robinhood's partnership with crypto.com, and NFL viewership trends. The conversation covers the evolution of sports broadcasting, the future of sports anchored mixed use districts, their impact on college campuses, Akron's innovative fan engagement in sports, and game strategy and ownership in sports.Please like, subscribe, and repost!Follow us on social media @Playbooks_Portfolios
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