Leveling Up with Gary and Jill

Gary Kusin
  • 5.0 (2)
  • ENTREPRENEURSHIP
  • UPDATED MONTHLY

Dive into the stories, challenges, and breakthroughs of entrepreneurs at pivotal moments in their journey on the Leveling Up with Gary & Jill podcast. Gary Kusin is a mentor, investor, and entrepreneur known for co-founding GameStop, and for the turnaround and transformation of Kinko’s, today operating as FedEx Office. Jill Louis is an attorney and C-suite advisor to businesses from startup to Fortune 50. Together, they delve into the critical aspects of business growth, from assessing strategic plans to diving deep into P&Ls, guiding entrepreneurs towards profitability and success.

  1. 05/08/2025

    Ready, Fire, Aim: Reflections on the Entrepreneurial Mindset

    In this special Season 2 finale of "Leveling Up with Gary & Jill," hosts Gary and Jill reflect on their journey mentoring entrepreneurs throughout the season. They dive deep into the entrepreneurial mindset, discussing what separates successful founders from those who struggle, the psychology of taking the leap into uncharted territory, and how to recognize when it's time to pivot or wind down a business. Drawing from their combined decades of experience, Gary and Jill share candid insights about team building, the importance of honest self-assessment, and the delicate art of delivering difficult truths to passionate entrepreneurs. Whether you're a seasoned business owner or just beginning your entrepreneurial journey, this reflective conversation offers valuable wisdom about the realities of building a business and the courage it takes to both start and, when necessary, gracefully exit.

    25 min

  2. 04/10/2025

    Beyond One-to-One: Transforming a Lactation Consulting Practice into a Scalable Business

    When registered nurse Tiffani Dickerson turned her own breastfeeding struggles into a thriving lactation consulting business, she never imagined she'd hit a ceiling at 583 clients a year. In this game-changing episode, Tiffani reveals the journey of The Breast Choice Lactation Services while Gary and Jill uncover her untapped potential to build an empire. From discovering the "one unit" mindset shift that could multiply her reach, to exploring untapped revenue streams in corporate wellness and certification programs, this conversation is a masterclass in transforming specialized expertise into scalable success. For anyone in a service-based business feeling maxed out, this episode will teach you how to nourish your business model beyond the one-to-one approach that keeps your growth on a restricted feeding schedule. Find out why the motherhood market might be the perfect place to apply fundamental business principles that turn passion into prosperity.

    37 min

  3. 03/28/2025

    Financial Literacy Takes Flight

    Dive into the classroom revolution as Shelby Patrice transforms financial literacy education from old school lectures to an engaging cross-disciplinary experience. Shelby shares how her background as a flight attendant, Miss Texas, and her experience being adopted led her to create a different approach to teaching financial literacy that spans from K-12 to adult education. Gary and Jill help Shelby recognize the need to evolve from founder to CEO, refine her pitch to investors, and expand her team with complementary skill sets. This episode highlights how Budget University's unique curriculum integrates financial concepts into traditional subjects like history, science, and math, making financial literacy relevant and engaging for students of all ages. Learn more: https://budgetuniversityonline.com/

    40 min

  4. 03/13/2025

    Rock & Roll Entrepreneurship: The Dave Furano Story

    Not many people have helicoptered into a football stadium with $100,000 cash in a briefcase, but that was just another day in the extraordinary career of Dave Furano. In this special episode, Gary sits down with the man who turned a Hard Rock Cafe connection into a $100 million business opportunity, convinced the Rolling Stones to partner on a handshake deal that lasted 30 years, and transformed concert merchandise from afterthought to multi-million-dollar industry. Dave reveals how he went from mortuary student to rock royalty, sharing insider tales like challenging Harvard MBAs on ticket pricing, to managing legends like Neil Diamond and Bob Dylan (who peer-pressured him into smoking his first joint 💨 ) Dave drops business wisdom throughout: his method for turning rejections into opportunities, his philosophy that helped Rock & Brews transform casino dining and entertainment, and his uncanny ability to spot value where others saw none. This is entrepreneurship on steroids—a masterclass in persistence, relationship-building, and staying two steps ahead in the wildest business environment imaginable. Get ready for the backstage pass to success. Check out Dave’s latest enterprise, Rock & Brews: https://www.rockandbrews.com

    38 min

  5. 02/27/2025

    Liquid Assets: Turning Hydration Data Into Startup Gold

    Two brothers found ample room for growth in the billion-dollar water bottle industry. John and Jameson Fitzgerald left their finance careers to tackle a gap in the health tech market: hydration tracking. Their startup FLOZ transforms your beloved Stanley, Hydroflask, or Yeti into a smart device with a simple straw attachment. In this episode, Gary and Jill challenge the founders on everything from their IP protection strategy and influencer marketing plans to manufacturing hurdles and fundraising approach. The brothers reveal their impressive preparedness, sharing insider details about athlete partnerships, manufacturing visits to Mexico, and their strategic two-phase capital raise already underway. If you've ever wondered how hardware startups navigate the treacherous path from concept to commercialization – or if you're just curious about the next big thing in health tech – this episode pours out a masterclass in entrepreneurial preparation. Learn more: https://www.flozhydration.com/ https://www.instagram.com/flozhydration/ https://www.linkedin.com/company/floz-hydration

    49 min

  6. 02/13/2025

    Thinking Inside the Box: Building a Global Cultural Experience

    Cultured is an innovative subscription box service that brings global cultural experiences directly to customers' doorsteps. Join us as Charlotte shares her entrepreneurial journey from walking 20 miles a day conducting market research to launching a business that curates authentic cultural items from countries around the world. Gary and Jill help Charlotte tackle crucial challenges around logistics, pricing strategy, and scaling her business while maintaining quality and authenticity. This episode offers valuable insights into bootstrapping a startup, conducting grassroots market research, and the importance of understanding unit economics before scaling. Learn more: https://www.iamcultured.co https://www.linkedin.com/company/iamcultured/ https://www.instagram.com/iamcultured.co/

    53 min

  7. 01/30/2025

    The Value Creation Puzzle: Building a Sellable Business

    When Anita O'Neal walked in with a plan to revolutionize small business budgeting, she didn't expect to walk out with a completely new perspective on her company's future. In this episode, listen as a straightforward financial services business transforms into a potentially scalable tech venture right before your eyes. Gary and Jill dig deep into Powerful People Plan's business model, challenging Anita's assumptions and uncovering hidden opportunities. From a pivot suggestion involving fractional CFOs to an eye-opening discussion about exit strategies, this episode showcases how one conversation can reshape an entrepreneur's entire trajectory. Whether you're wrestling with scaling challenges or plotting your own exit strategy, this episode delivers the wake-up call every founder needs. Learn more: www.linkedin.com/in/anita-oneal www.powerfulpeopleplan.com https://instagram.com/PowerfulPeoplePlan https://www.facebook.com/PowerfulPeoplePlan

    48 min

  8. 01/16/2025

    Beyond the End Zone: Creating Basketball's Next Entertainment Empire

    What happens when a former NFL player sets out to create basketball's answer to Topgolf? Derrick Mayes, who went from catching passes for the Green Bay Packers and Seattle Seahawks to becoming CEO of Jump Shot Live, shares his vision for revolutionizing basketball entertainment. Drawing from lessons learned watching his father's entrepreneurial journey and his own experiences in professional football, Mayes is building a groundbreaking concept that combines proprietary rotating hoop technology, immersive entertainment, and the pure love of basketball. With patent-pending innovations and partnerships with industry veterans from Topgolf, Jump Shot Live aims to transform how people experience the world's second most popular sport. Listen as Mayes reveals crucial insights about scaling a first-of-its-kind venture, the importance of starting small while thinking big, and how to build the right team of "birthers and rearers" to bring an innovative concept to life. Learn More: https://jumpshotlive.com/our-story https://www.instagram.com/jumpshot.live/ https://www.linkedin.com/company/jumpshotinc/

    47 min
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About

Dive into the stories, challenges, and breakthroughs of entrepreneurs at pivotal moments in their journey on the Leveling Up with Gary & Jill podcast. Gary Kusin is a mentor, investor, and entrepreneur known for co-founding GameStop, and for the turnaround and transformation of Kinko’s, today operating as FedEx Office. Jill Louis is an attorney and C-suite advisor to businesses from startup to Fortune 50. Together, they delve into the critical aspects of business growth, from assessing strategic plans to diving deep into P&Ls, guiding entrepreneurs towards profitability and success.

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