Investing Episodes

Baseball Entrepreneurship Investing Venture Capital Hockey Olympics Basketball Soccer

Season 1 Finale — The Game Plan: Greatest Hits

Be sure to tune into the final episode of Season 1 of "The Game Plan" as Jay and Tim take a look back and highlight some of their favorite moments from the past year including audio clips from Super Bowl Champions, Olympic Gold Medalists, All-NBA team honorees and Hall of Famers. Listeners new and old will enjoy listening to these highlights, as well as the color commentary of The Game Plan hosts Jay Kapoor and Tim Katt. We explore why these moments really stood out in a season full of insight, authenticity, and emotion. Featured guests include: Hall of Fame inductee, Olympic Gold Medalist and Sports Innovation Lab Co-Founder Angela Ruggiero USWNT member, FIFA Women's World Cup Champion, and Co-Founder of Re-Inc Meghan Klingenberg Former All-NBA Shooting Guard, Team USA Olympic Gold Medalist, and Founder of Twenty-Two Ventures Michael Redd 3x Super Bowl Champion, media personality, and Co-founder of "Mark's All-Pros" Mark “Stink” Schlereth Super Bowl Champion and founder of The Wine MVP Will Blackmon Former Major League Baseball player and Co-founder of Players for the Planet Chris Dickerson Jay and Tim also wrap the episode with key takeaways from Season 1 of The Game Plan including: ✍🏿 Athletes-Investor strategy 🔌 The power of humility and authenticity 🗣 Dispelling the "Broke Athlete" narrative 🤸🏼‍♀️ The exciting future for women's sports Special thanks to Will Richardson and Meghan Roxas for all of their help in producing and promoting Season 1 of The Game Plan. Be sure to follow co-hosts Jay Kapoor ( @JayKapoorNYC ) and Tim Katt ( @Tim_Katt ) for all things sports, media, tech, and venture capital. Follow The Game Plan on Twitter ( @thegameplanshow ) and Instagram ( @gameplanshow ) for show news and updates, to recommend guests, and for bonus content!

Basketball Investing Venture Capital

Matthew Dellavedova — Lessons from Investing in Venture Capital, Angel Syndicates, and Trading Cards

NBA World Champion and host of "The Delly Podcast" Matthew Dellavedova joins The Game Plan to discuss his off-court leap into tech investing and podcasting including: 😇Forming his own investment syndicate on Angel List 🎴 Investing in store-of-value assets like cryptocurrency and trading cards 🇦🇺 Australia as a hotbed for sport science innovation 💸The one thing he wishes he had done differently at the start of his investment career Dellavedova shares with Tim and Jay how he first started to learn about venture investing in Milwaukee of all places (while playing for the Milwaukee Bucks), and how his Aussie roots have influenced his investment interest areas in sport science and biometrics. We also discuss why trading cards have skyrocketed in value over the past year, and the influence the Covid pandemic has played on asset values. In this episode, Dellavedova gets candid about the investment lessons he has learned over the years including one key thing he wishes he had done differently when he first started writing venture capital checks. We go deep on the things our guest looks for in a company when making an investment, and how important it is to align with the right people both on and off the court. On the court, Matthew Dellavedova is best known as the point guard for the NBA's Cleveland Cavaliers where he won an NBA World Championship with LeBron James and Kyrie Irving in 2016. Dellavedova has been in the NBA since 2013, and prior to that, he played college basketball for Saint Mary's College where his number 4 was retired. He is a proud Aussie who has appeared for the Australian National Team in both the 2012 London Olympics and the 2016 Rio Olympics, as well as multiple World Cups. You can follow Matthew Dellavedova on Twitter and Instagram (@matthewdelly), and subscribe to "The Delly Podcast" wherever you listen to The Game Plan! Follow co-hosts Jay Kapoor ( @JayKapoorNYC ) and Tim Katt ( @Tim_Katt ) for all things sports, media, tech, and venture capital. Follow The Game Plan on Twitter ( @thegameplanshow ) and Instagram ( @gameplanshow ) for show news and updates, to recommend guests, and for bonus content!

Venture Capital Football Investing

Eric Winston — Blocking & Tackling of Negotiating the CBA as NFLPA President

This week former NFLPA President, Eric Winston , joins The Game Plan to give listeners a peek behind the curtain on the most recent NFL CBA negotiation. Winston is an 11-year NFL veteran where he is best known on the field for his role as an offensive tackle for the Houston Texans, Kansas City Chiefs, Arizona Cardinals, and Cincinnati Bengals. Winston served as President of the NFLPA from 2014-2020 where he played a critical role in negotiations with the NFL around player health and safety, financial literacy, and workplace conditions, especially in the locker room. Most recently, Winston wrapped up his role as President of the NFLPA with the successful negotiation of a new collective bargaining agreement that is set to run through 2030. Our guest now holds the role of Chief Partnerships Officer at OneTeam, a group jointly founded by the NFLPA, MLBPA, and RedBird Capital Partners. OneTeam manages the commercial licensing rights of athletes across a diverse cross-section of properties, creates new marketing opportunities through its Athlete Marketing business, and generates unique deal flow and investment opportunities through its Venture Investment capabilities. In this episode, we explore what went into developing the recently agreed upon CBA, and how our guest was able to manage the voices and needs of over 2,000 players to help bring labor peace to the NFL for the next decade. Our guest also shares the key things from his playing career that have made the biggest impact on his work off the field, and helps us understand the things OneTeam is doing to help empower professional athletes around the world. Listeners won't want to miss our discussion around the early visibility the NFLPA and OneTeam had to Unicorns like Uber, Slack, and DocuSign You can follow Eric Winston on Twitter @EricWinston and visit https://joinoneteam.com/ to learn more about OneTeam Partners. Follow co-hosts Jay Kapoor ( @JayKapoorNYC ) and Tim Katt ( @Tim_Katt ) for all things sports, media, tech, and venture capital. Follow The Game Plan on Twitter ( @thegameplanshow ) and Instagram ( @gameplanshow ) for show news and updates, to recommend guests, and for bonus content!

Baseball Investing

Brendan Harris — Tapping into Major League Players' Full Earning Potential with X10 Capital

Tapping into Major League Players' Full Earning Potential with X10 Capital

Soccer Real Estate Investing

Dan Kennedy — Breaking down MLS' Expansion Strategy & Driven Capital Partners Commercial Real Estate Empire

This episode of The Game Plan features Dan Kennedy , former Major League Soccer goalkeeper turned real estate investor. Dan is now Managing Partner at Driven Capital Partners in Long Beach, CA where he focuses on commercial real estate development and property management, working with other professional athletes to help them generate a passive income that will pay off well beyond the prime of their career. We start this episode by exploring the evolution of Major League Soccer and the role that rapid league expansion has played over the years. Dan shares his perspective as a player in the pivotal years of MLS, including tense moments as a member of the executive board of the MLS Player’s Association. Dan also talks about his transition from a career as a professional soccer player into a business professional, and the role business school played in helping him find his way in life beyond the pitch. We discuss his front office role with the LA Galaxy, and why he ultimately decided to change things up and pursue a career in commercial real estate development. Listeners won’t want to miss Dan’s candid point of view on what every professional athlete should be doing with their money (that most aren’t doing today). Special thanks to Tim’s former colleague Andrew Hayes for making the introduction to our guest. Be sure to follow Dan on Twitter and Instagram ( @1DanKennedy ) to keep up with everything he is doing today, as well as his investment group’s website: https://www.drivencap.com . If there is a guest you’d like to see join us on a future episode of The Game Plan please follow and reach out to co-hosts Jay Kapoor ( @JayKapoorNYC ) and Tim Katt ( @Tim_Katt ) on Twitter! Follow The Game Plan on Twitter ( @thegameplanshow ) and Instagram ( @gameplanshow ) for show news & updates, as well as bonus content!

Football Venture Capital Investing

Stewart Bradley — NFL Linebacker turned B2B-Investor Shares Alternatives to Venture Capital

SaaS investor and former NFL linebacker Stewart Bradley joins The Game Plan to share his life journey and evolution from football player to sophisticated tech investor. Shortly after his seven-year career with the Philadelphia Eagles, Arizona Cardinals, and Denver Broncos came to an end, our guest chose a different path; joining Goldman Sachs as an investment banking analyst in their esteemed technology media and telecom (TMT) group. Stew shares with us his decision process in choosing this path, and why he ultimately opted to go into banking versus pursuing an MBA. Today, our guest is General Partner and Co-Founder of El Cap holdings where he is carving a unique path in the crowed software investment landscape. Stew shares with us the currency, beyond capital, with which he is building the fund. We also explore his investment thesis and the types of companies he looks to back. Seasoned investors familiar with enterprise software and the SaaS landscape will especially appreciate what Stewart has to say about investing in "opinionated software products". We also discuss the power of effort and focus and how these two attributes over the long term have helped lead our guest to success both on and off the football field. Learn more about Stewart Bradley's investment approach by visiting El Cap Holding's website at https://www.elcapholdings.com/ or emailing info@elcapholdings.com . Follow The Game Plan on Twitter ( @thegameplanshow ) and Instagram ( @gameplanshow ) for show news and updates, to recommend guests, and for bonus content! You can also follow co-hosts Jay Kapoor ( @JayKapoorNYC ) and Tim Katt ( @Tim_Katt ) for all things sports, media, tech, and venture capital.

Football Investing Entrepreneurship

Dhani Jones — The Art of Storytelling in Entrepreneurship, Investing, Media and the NFL

TV personality and NFL alum Dhani Jones joins The Game Plan to share his perspective on all things media, technology, and storytelling. Dhani Jones played 11 years as a linebacker in the NFL, including time with the New York Giants, Philadelphia Eagles, and Cincinnati Bengals. During his NFL career, Dhani became the first active player to be featured on the NFL Network as an analyst. Dhani details those early days of the NFL Network where he did everything from interviewing players on the sideline of playoff games to helping pack up the cable truck after games. In addition to his work as a football player and football analyst, our guest became a household name through his television work as the host of the Travel Channel's "Dhani Tackles the Globe" and CNBC's "Adventure Capitalists". Dhani shares the story of what it was like to work for two well-known companies in Cincinnati (the Cincinnati Bengals and Scripps Networks) at the same time, and how a run-in with Bengal's owner Mike Brown in the team cafeteria led Dhani to play some of the best football of his career. Other topics included on this episode include how a Montessori education as a kid helped fuel Dhani's curiosity today, and how the desire to go out and do something is the most important attribute someone can have on their way to becoming an entrepreneur. Today, Dhani is Chairman of QEY Capital, an investment group he founded with fellow University of Michigan alum and Goldman Sachs veteran Ebow Ivory Vroom. You can follow Dhani Jones on Twitter and Instagram for all of his latest interests and activities off the field. Visit https://qeycapital.com/ to find out more about Dhani's approach to investing. Follow co-hosts Jay Kapoor ( @JayKapoorNYC ) and Tim Katt ( @Tim_Katt ) for all things sports, media, tech, and venture capital. Follow The Game Plan on Twitter ( @thegameplanshow ) and Instagram ( @gameplanshow ) for show news and updates, to recommend guests, and for bonus content!

Basketball Investing Venture Capital

Mason Plumlee — Succeeding in Healthcare Investing as an Active NBA Player

From buying custom oversized mattresses for his Brooklyn Nets teammates to launching a tech-focused interview series during a global pandemic, we cover it all on this episode of The Game Plan . Mason Plumlee of the NBA's Denver Nuggets joins us to share his perspective on investing, and how his hometown of Warsaw, Indiana played a key role in why he likes to focus on healthcare for his alternative asset exposure. In this episode, we talk to our guest about the NBA hiatus and its upcoming return. This includes learning more about what has drawn him to start an online show of his own, "Founders Series", on FB Live. At the end of the show, Tim and Jay also introduce a new segment called "Partner Rundown" where we each take a turn giving our 1-minute perspective on five topics covered in the conversation with our guest. This Partner Rundown includes: Oversized Mattresses Investing in Healthcare Sport as a Venture Asset Mason's Founders Series Leveraging Access as a Pro Athlete Make sure to follow Mason Plumlee on Twitter and LinkedIn to catch everything he's up to on and off the hardwood. Listeners can also check out the "Founders Series" on Mason's Facebook page . Follow co-hosts Jay Kapoor ( @JayKapoorNYC ) and Tim Katt ( @Tim_Katt ) for all things sports, media, tech, and venture capital. Follow The Game Plan on Twitter ( @thegameplanshow ) and Instagram ( @gameplanshow ) for show news and updates, to recommend guests, and for bonus content!

Basketball Investing Venture Capital

Michael Redd — How Venture Capital & Private Equity Can "Empower Through Economics"

Former All-NBA Shooting Guard and Team USA Olympic Gold Medalist Michael Redd joins The Game Plan to discuss his approach to venture investing and to share with us what he's doing to make a lasting difference in his hometown of Columbus, OH. In this episode, we discuss with our guest how today's game differs to the NBA of the early 2000s. Listeners will appreciate Redd's humility as he shares his perspective after being removed from the NBA for over 8 years. Today our guest is an active venture investor which includes his own fund, Twenty-Two Ventures, as well as his involvement with leAD Sports, an early-stage venture capital fund backed by the Adi Dassler family. We discuss how Redd was attracted to the idea of ownership over endorsement early in his career, and how that led him to a retirement-focused on alternative investments. We also dig in on the idea that pro athletes are becoming more aware of their value and the power dynamics at play, both on the court and off it. This episode of The Game Plan includes a very open and honest conversation that shines on light on the Black Lives Matter movement through the lens of our guest, a former pro athlete who has dedicated his life to helping others and making a difference in his local community. Make sure to follow Michael Redd on Twitter and Instagram to keep up with his latest efforts. Listeners should also check out his " Betting on Yourself " podcast on iTunes. Follow co-hosts Jay Kapoor ( @JayKapoorNYC ) and Tim Katt ( @Tim_Katt ) for all things sports, media, tech, and venture capital. Follow The Game Plan on Twitter ( @thegameplanshow ) and Instagram ( @gameplanshow ) for show news and updates, to recommend guests, and for bonus content!

Basketball Entrepreneurship Investing

Jerome "Junkyard Dog" Williams — Creating and Monetizing Intellectual Property as a Retired Player

JYD! The "Junkyard Dog" Jerome Williams joins The Game Plan to share how the hard work and hustle he demonstrated during his 9-year NBA career with the Detroit Pistons, Toronto Raptors, Chicago Bulls, and New York Knicks has translated to the many successes he has had off the court.

Basketball Entrepreneurship Venture Capital Investing

Baron Davis — NBA All-Star on Power of Athletes Owning Their Own Media Brands

Former NBA All-Star Baron Davis joins The Game Plan to discuss his success both on and off the court, including his development as an investor long before it became in vogue to see athletes playing that role.

Investing Football Venture Capital

Cliff Avril - Building a Winning Team Around You As Both a Pass Rusher and Private Equity Investor

This week's episode of The Game Plan features Cliff Avril, Super Bowl XLVIII Champion with the Seattle Seahawks. Cliff Avril is a 10-year NFL vet and is best known for his role as a Defensive End on the "Legion of Boom". During his football career, Cliff was also recognized as a nominee of both the Walter Payton Man of the Year award and Art Rooney Sportsmanship Award. In this episode, Cliff talks about what it was like transitioning from his rookie year as part of one of the worst team seasons in NFL history (0-16 Detroit Lions) to later in his career when he joined an experienced Seahawks' locker room led by Richard Sherman, Marshawn Lynch, and Michael Bennett. Off the field, Cliff is busy with the Cliff Avril Family Foundation which focuses primarily on bringing attention to the risks associated with juvenile diabetes, as well as providing educational opportunities and housing in his native country of Haiti. In addition to his philanthropic efforts, Cliff discusses his interest in media and what it means to provide an athlete's perspective behind the microphone for Seattle sports talk radio. Make sure to follow Cliff on Twitter and Instagram for even more regular updates on everything he's up to. Follow co-hosts Jay Kapoor (@JayKapoorNYC) and Tim Katt (@Tim_Katt) for all things sports, media, tech, and venture capital. Follow The Game Plan on Twitter (@thegameplanshow) and Instagram (@gameplanshow) for show news & updates, to recommend guests, & for bonus content!

Basketball Investing Venture Capital

Spencer Hawes — Evolving NBA Playing Styles While Learning VC Investing Playbook

NBA journeyman and proud Seattleite Spencer Hawes joins The Game Plan to discuss his interests on and off the basketball court, and life today as he contemplates retirement during the uncertainty of a global pandemic.

Investing Basketball

Detlef Schrempf — Seattle Supersonic Legend on Finding Success in VC & Wealth Management

16-year NBA veteran, cult favorite, and former Seattle Supersonic Detlef Schrempf joins The Game Plan to discuss life after basketball and his role leading Business Development at Coldstream Wealth Management.

Investing Basketball

Trevor Booker — NBA Veteran's Reflections on Retirement Day and his Next Career as an Investor

NBA veteran and Clemson alum Trevor Booker joins The Game Plan to share his perspective on investing, and the importance of surrounding yourself with a team you can count on.