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.
Playbooks and Portfolios: The Kurt Benkert Experience
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.
Chapters
00:00 Kurt Benkert's Journey to the NFL
03:33 The Transfer Portal and Its Implications
08:55 Navigating the NFL Landscape
15:00 Learning from Legends: Aaron Rodgers
19:55 The Rise of Content Creation
23:38 From NFL to Entrepreneurial Journey
26:00 Navigating Life After Football
36:09 Building a Brand with Dime Lab
39:52 Future Aspirations and Goals
45:50 Leadership and Team Dynamics
1 Oct 2026
Playbooks and Portfolios: Sports Media, Alternate Markets, and Protect College Sports
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.
Takeaways
Sports broadcasting salaries skyrocketing
Private equity reshaping team valuations NIL deals are transforming college sports
Athlete representation is crucial
Chapters
00:00 The Rise of Sports Broadcasting Salaries
12:03 Private Equity's Influence on Sports
25:26 The Boom of Sports Betting and Its Implications
33:39 NIL and the Future of College Sports
34:08 The Impact of NIL Deals
36:44 Transfer Portal Dynamics
39:57 The Value of Scholarships
44:38 Athlete Representation in Decision-Making
51:43 Key Conversations for College Athletes
24 Sept 2026
Playbooks and Portfolios: Super Bowl Champion Bernie Kosar!
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
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
2 ratings
Spotify
5.0 / 5
7 ratings
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