The Sports Umbrella

Kelly Okun

The Sports Umbrella podcast presented by GalwayPlus covers all things sports. Soak in all the knowledge from our guests, who range from pro athletes playing up a storm to industry experts making it rain. Host Kelly Okun is a former pro golfer and founder and CEO of Fairway to Green, an equitable sports media company.

Episodes

  1. FEB 25

    Jadan Randolph | Vanguard Maven Group | Athlete Branding & Community Building

    In this episode of The Sports Umbrella presented by GalwayPlus, host Kelly Okun interviews Jadan Randolph, co-founder of Vanguard Maven Group.  VMG is a marketing and strategy consultancy that helps teams, leagues and athletes build communities through resonant storytelling, new IP, shows and events across the sports, media and entertainment industries.  Jadan discusses differences in women’s sports fandom, Gen Z’s desire for digital-first access and the impact of experiential events. Kelly and Jadan even debate the pros and cons of sports betting They go on to discuss the strategy behind building community and driving fandom for products like the hit TV show, Love Island, and end with Jadan's take on what streaming and online communities will look like in five years. The Sports Umbrella is a Fairway to Green podcast sponsored by GalwayPlus. Learn more about GalwayPlus at www.galwayplus.com.

    21 min

  2. FEB 11

    Shannon Bahrke and Doug Lewis | Champions Advantage | The Olympic Experience

    In this episode of The Sports Umbrella presented by GalwayPlus, host Kelly Okun is joined by former Olympians Shannon Bahrke and Doug Lewis. Shannon is a three-time Olympian and two-time medalist in freestyle skiing and Doug is a two-time Olympian and World Championship medalist in downhill skiing.  Doug and Shannon share their journeys from making the U.S. Ski Team to competing in the Winter Games, emphasizing the importance of mental toughness as a competitive advantage.  They discuss the 2026 Milano Cortina Winter Games and highlight what to expect in their sports. They also delve into their personal experiences, including the thrill of their Olympic moments and the challenges they faced while retiring from their sports. Shannon and Doug shed light on their continued passion for giving back through mentoring and have teamed up to form Champions Advantage, a mental skills training program geared toward young athletes. The Sports Umbrella is a Fairway to Green podcast sponsored by GalwayPlus. Learn more about GalwayPlus at www.galwayplus.com.

    55 min

  3. JAN 28

    Isaiah Kacyvenski | Will Ventures | Sports Investing

    In this episode of The Sports Umbrella presented by GalwayPlus, host Kelly Okun speaks with Isaiah Kacyvenski, a former NFL player and double Harvard graduate, who shares his journey from growing up in poverty to becoming a prominent venture capitalist. Isaiah opens up about sports and academics helping him escape poverty, his experiences playing in the NFL and his venturing into the investment landscape. His investment philosophy is one to be studied, and he has a keen eye for trends in sports investing. He also discusses the founding of Will Ventures, a venture capital firm focused on sports, media, entertainment and tech-enabled businesses. Lastly, Isaiah offers advice for aspiring athletes and sports investors. The Sports Umbrella is a Fairway to Green podcast sponsored by GalwayPlus. Learn more about GalwayPlus at www.galwayplus.com.

    27 min

  4. JAN 14

    Drew Sheinman | Brand Velocity Group | Profit With Purpose

    In this episode of The Sports Umbrella presented by GalwayPlus, host Kelly Okun speaks with Drew Sheinman, a founding partner of Brand Velocity Group, about his unique take on private equity and sports investing. Drew discusses Brand Velocity Group's mission of combining profit with purpose, focusing on corporate culture and ensuring employee alignment. He elaborates on their Share the Gains program and how the firm integrates ethical values into their investment strategies.  The conversation also delves into the evolution of sports as an asset class, the role of relationships in private equity, and the emergence of opportunities in sports media, technology and women's sports as new avenues for investment. If you're interested in breaking into the sports investment industry, Drew also shares some advice on how to open those doors. The Sports Umbrella is a Fairway to Green podcast sponsored by GalwayPlus. Learn more about GalwayPlus at www.galwayplus.com.

    21 min

  5. 12/17/2025

    Jimmy Roberts | NBC Sports | Golf

    In this episode of The Sports Umbrella presented by GalwayPlus, host Kelly Okun speaks with Jimmy Roberts, a legendary sportscaster for NBC Sports and, most recently, co-founder and COO of Big Swing Media. Jimmy and Kelly immediately dive into the significance of storytelling in sports, particularly in golf, and how it engages younger and more diverse audiences. Jimmy emphasizes the necessity of keeping personal stories at the forefront. Their conversation then touches on the challenges faced by traditional golf tours in light of emerging leagues like LIV Golf and the necessity for the PGA Tour to evolve.  On the women's side, new leadership at the LPGA Tour is poised to potentially shake things up while still maintaining a focus on mental health and star athletes. The discussion concludes with Jimmy sharing about his new platform, Big Swing Media, which aims to explore the business side of golf through various mediums like a podcast, a newsletter and conferences. The Sports Umbrella is a Fairway to Green podcast sponsored by GalwayPlus. Learn more about GalwayPlus at www.galwayplus.com.

    32 min

  6. 12/03/2025

    Dmitry Popov | WurQ | Health and Wellness Tech

    In this episode of The Sports Umbrella, host Kelly Okun speaks with Dmitry Popov, Co-founder and CEO of WurQ, a wearable tech startup focused on movement tracking for athletes.  Dmitry shares his impressive background and the inspiration behind creating WurQ, emphasizing the unique capabilities of their wearable technology. He discusses the implementation of AI in their system, the diverse applications of their technology beyond fitness, the importance of user feedback in their product development and the future of wearable tech. If you're interested in health and wellness and/or tech startups, this episode is for you! The Sports Umbrella is a Fairway to Green podcast sponsored by GalwayPlus. Learn more about GalwayPlus at www.galwayplus.com.

    18 min

  7. 11/04/2025

    Craig Brown | Galway Family Office | NIL

    Welcome to the first episode of The Sports Umbrella, where host Kelly Okun interviews Craig Brown about NIL, athlete wealth management and more. Craig is the Managing Principal and Founder of the Galway Family Office and a former baseball player. Craig shares insights from his own athletic career and transition to wealth management, emphasizing the importance of financial literacy, planning for early retirement and the intricacies of NIL deals. The discussion also delves into the critical role of regulatory oversight in protecting young athletes' financial futures. If you're an athlete going into the collegiate or professional ranks and want to avoid the typical financial pitfalls - especially in NIL - or you are simply interested in learning more about how wealth management for athletes differs from that of high-net-worth individuals, this episode is for you! The Sports Umbrella is a Fairway to Green podcast sponsored by GalwayPlus. Learn more about GalwayPlus at www.galwayplus.com.

    24 min
  • 7 Episodes

Ratings & Reviews

5
out of 5
3 Ratings

About

The Sports Umbrella podcast presented by GalwayPlus covers all things sports. Soak in all the knowledge from our guests, who range from pro athletes playing up a storm to industry experts making it rain. Host Kelly Okun is a former pro golfer and founder and CEO of Fairway to Green, an equitable sports media company.

Information

  • Creator
    Kelly Okun
  • Years Active
    2025 - 2026
  • Episodes
    7
  • Rating
    Explicit
  • Copyright
    © 2026 The Sports Umbrella
  • Show Website
    The Sports Umbrella