Leveling Up with Gary and Jill

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 pivo...

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&qu...

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 Shelb...

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 c...

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...

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 log...

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 mod...

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 footb...

Meet Tammy Marshall, founder and CEO of La Lueur Health & Wellness, who's revolutionizing healthcare delivery in minority communities through a unique blend of primary care and med spa services. Her 45-foot medical bus nicknamed "Lady Bird" brings healthcare directly to underserved areas, while her brick-and-mortar location offers a welcoming environment that makes patients feel truly valued....

Join us as we sit down with Dr. Amanda Lewis, founder and CEO of Lewie, who's on a mission to transform oral care from a health necessity into a beauty essential. After 20 years as a practicing dentist, Dr. Lewis noticed a striking pattern: patients consistently prioritized cosmetic dental procedures over health-related ones. This observation sparked her entrepreneurial journey to create innovativ...

In this compelling episode, Laura Baldwin, Managing Partner of RevTech Ventures, brings her extensive investment experience to a candid discussion about the stark realities and real opportunities in funding female founders. Drawing from her decade-plus experience as an angel investor and her current role leading a $10 million fund focused on women-led retail technology ventures, Laura explores the...

Demi Oloyede, founder and CEO of Limpiar, shares her journey of building a tech-enabled cleaning services platform. What starts as a conversation about connecting cleaners with customers evolves into a masterclass on strategic focus and business model refinement. Gary and Jill help Demi navigate the challenges of managing a two-sided marketplace while avoiding the temptation to "boil the ocean." T...

Dawn Myers, the visionary founder and CEO of Richualist, takes us on her extraordinary journey of creating a revolutionary hair styling device for textured hair, sharing the triumphs and challenges she faced along the way. From her early days of sketching ideas on legal pads to appearing on Shark Tank, Dawn's story is a testament to the power of perseverance and innovation. Listeners will be inspi...

Gary Kusin sits down with Johannes Luckemeier, the innovative mind behind Glydsphere. Johannes shares his journey from working in the German automotive industry to developing a groundbreaking aftermarket product that allows electric car owners to customize their vehicle's sound. As Johannes stands at a critical juncture in his entrepreneurial journey, Gary offers invaluable insights on scaling the...

The Season 2 premiere of Leveling Up with Gary & Jill features Randy Bowman, CEO of At Last! - a pioneering educational initiative transforming the lives of underprivileged children. Randy's remarkable journey sets the stage for a riveting discussion on how business acumen can be leveraged to address educational inequality. Randy shares the inspiration behind At Last's innovative &quot...

Gary and Jill reflect on the key takeaways from their inaugural season of "Leveling Up with Gary and Jill." They discuss the common challenges faced by entrepreneurs, including turning a mission into a viable business model, understanding market dynamics, and the importance of financial planning. They also share insights on what makes a successful entrepreneur, such as the importance of...

PloomSocial is an innovative fundraising platform revolutionizing donor engagement through episodic video storytelling. We welcome founder Cary Carlton as he shares his entrepreneurial journey, exploring PloomSocial's unique approach to tackling donor retention issues, leveraging AI, and incorporating influencer partnerships. The conversation delves into the challenges of entrepreneurship, inc...

In this episode of Leveling Up with Gary & Jill, we sit down with Lynn Wilford Scarborough, CEO of Cheeza Pleeza, a unique keto-friendly cheese brand. Lynn shares her unexpected journey from caring for her mother to becoming an accidental food entrepreneur. Gary and Jill dive deep into the challenges of scaling a food business, exploring topics such as product development, distribution channel...

In this episode, we sit down with Leon Jacobson, founder of Nerveli, a startup aiming to transform the landscape of chronic pain management. Leon shares his personal journey through a maze of medical consultations that ultimately inspired his innovative approach to pain diagnosis and treatment. Nerveli’s mobile app combines medical science with AI to provide personalized pain management strategies...

Neiman Carlyle is the founder of Surrealty Locating, a real estate brokerage disrupting the rental and leasing industry. Leveraging the untapped power of social media and influencer marketing, Carlyle has transformed the traditional real estate landscape by catering to the underserved Gen Z market. As the conversation unfolds, Carlyle's entrepreneurial epiphany emerges: his company is not mere...

In this energizing episode of Leveling Up with Gary and Jill, we sit down with Sebastian Vera, the founder and CEO of BioGroundz, a coffee recycling company that's brewing up a storm in the world of sustainable entrepreneurship. Sebastian takes us on a journey through his passion project, which began with a simple idea during his time as a coffee shop owner: transforming spent coffee grounds i...

In the second part of our conversation with Bill Chinn, we move from the tumultuous world of GameStop to entrepreneurship. As the president of The DEC Network, Bill now dedicates his time and expertise to driving innovation and economic impact by helping entrepreneurs start, build, and grow their businesses. We delve into The DEC Network's mission and the valuable lessons Bill has carried with...

In the first installment of this captivating two-part special, ‘Leveling Up’ takes you on an exclusive journey through the turbulent history of GameStop, one of the most iconic companies in the gaming industry. Join us as we sit down with Bill Chinn, a veteran of the early days of Babbages and GameStop, and Gary Kusin, former CEO of GameStop, for an insider's perspective on the company's r...

In this illuminating episode of Leveling Up with Gary and Jill, we delve into the captivating world of art with Eboni Boyd, founder of Museum Advocate. As an entrepreneur on a mission to expand the art market through innovative technological solutions, Eboni shares her winding path from academia to politics and, ultimately, to the heart of the art world. Throughout the conversation, Eboni grapples...

Brian Hart is a visionary entrepreneur who is shaking up the beverage industry with his creation, Vitam. This innovative drink combines the power of hemp-derived THC and CBD with a carefully crafted blend of vitamins and minerals, offering a refreshing and healthier alternative to alcohol. Brian shares his incredible journey of bringing Vitam to life, from navigating the complex world of distribut...