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.
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.
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:
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
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
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/
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
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/
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. In this enlightening conversation, Gary and Jill help Tammy explore scaling strategies as she transitions from hands-on practitioner to full-time CEO. The discussion reveals how authentic leadership, strategic thinking about revenue streams, and maintaining high standards while scaling can transform both healthcare delivery and business success. Tammy's journey showcases how combining mission-driven purpose with smart business acumen can create meaningful impact while building a sustainable enterprise.
Learn More
https://lalueurhw.com
https://www.instagram.com/la_lueur_hw
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 innovative oral care products that bridge the gap between health and beauty.
In this enlightening conversation, Dr. Lewis shares her vision of making the smile the centerpiece of beauty routines, backed by her development of a patented flossing disc and a chemical-conscious whitening wand. Gary and Jill guide her through crucial strategic considerations, from positioning Lewie as a premium beauty brand to exploring mass market opportunities. The discussion reveals important insights about distribution challenges, the power of strategic partnerships, and the delicate balance between maintaining a premium image and achieving necessary scale.
Watch as our hosts help Dr. Lewis uncover potentially game-changing perspectives about her go-to-market strategy, including innovative approaches to hotel amenities, travel retail, and the possibility of dual-brand strategies. This episode offers valuable lessons for entrepreneurs navigating the complex landscape of consumer packaged goods, especially those trying to disrupt established markets with innovative products.
Learn more about Lewie:
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 paradox of superior returns from female-founded companies despite receiving only 2% of venture capital. Through probing questions from Gary and Jill, the conversation evolves into a strategic discussion about transforming fundraising approaches - shifting from individual investor cultivation to pursuing major institutional commitments. The episode offers unique insights into how traditional fundraising models might be reimagined to better serve both investors and female entrepreneurs, while highlighting the untapped potential in the intersection of retail technology and female leadership.
Learn more about RevTech Ventures and Golden Seeds
https://revtechventures.com/
https://goldenseeds.com/
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."
The discussion reveals how Limpiar pivoted from individual contractors to small business partnerships, transformed their customer acquisition strategy, and leveraged HOA relationships to build a more sustainable business model. Through their platform, Limpiar is bringing transparency and trust to an industry traditionally plagued by uncertainty and inconsistency. Demi's candid insights about battling "shiny object syndrome" and the importance of establishing clear priorities resonate with entrepreneurs at any stage.
As the conversation unfolds, Gary and Jill guide Demi through crucial strategic considerations, from managing customer trust to scaling operations efficiently. The episode showcases how focusing on core customer segments and building strong relationships with property managers and HOAs can create a path to sustainable growth. Demi's innovative approach to lean operations and smart outsourcing provides a blueprint for entrepreneurs looking to build scalable businesses without overextending resources.
Whether you're running a marketplace business or struggling with strategic focus, this episode offers valuable lessons on the art of building a focused, scalable business model while maintaining the discipline to stay true to your core mission.
Learn more about Limpiar
https://limpiar.online/
https://instagram.com/Limpiaronline
https://www.linkedin.com/company/limpiaronline/
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 inspired by Dawn's candid account of bootstrapping her company, including selling her house and liquidating her 401k to fund early prototypes. She openly discusses the unique hurdles she encountered as a Black woman in the tech and manufacturing world, offering valuable insights into navigating these spaces as an underrepresented founder.
This episode is a must-listen for aspiring entrepreneurs, especially those from underrepresented backgrounds, looking to make waves in their industries. Dawn's journey with Richualist not only highlights the potential for innovation in the beauty tech space but also provides a roadmap for turning a personal pain point into a market-disrupting solution. Tune in for an inspiring conversation that will challenge you to think differently about entrepreneurship, funding, and the power of perseverance.
Learn More about Richualist:
https://richualist.com/
https://instagram.com/getrichualist
https://www.tiktok.com/@get.richualist
https://www.linkedin.com/company/getrichualist/about/
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 business, protecting intellectual property, and preparing for potential interest from major industry players. The conversation delves into the challenges of disrupting the global auto market and the importance of strategic thinking as the company grows.
This episode is a must-listen for entrepreneurs navigating the complexities of hardware and software development, especially those looking to make waves in established industries. Tune in to hear Gary's advice on transitioning from an engineering mindset to a CEO perspective, and how to plan for long-term success while managing day-to-day operations.
Learn more about Glydsphere:
https://invest.microventures.com/offerings/glydsphere
https://glydsphere.com/
https://www.instagram.com/glydsphere/
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 "boarding experience" model, which is redefining after-school programs by providing a 17-hour immersive learning environment. He delves into the challenges of translating personal adversity into social innovation and applying for-profit strategies to non-profit challenges. The conversation explores the power of data-driven processes in education, the delicate balance between regulatory compliance and program effectiveness, and the ambitious plans for scaling this revolutionary educational model.
This episode offers listeners a masterclass in entrepreneurial thinking applied to social impact. Randy's story illustrates how strategic planning, innovative problem-solving, and a deep understanding of both business and human nature can create transformative change. Whether you're an entrepreneur, educator, or someone passionate about social innovation, this conversation will inspire you to think differently about the challenges facing our education system and the creative solutions that can arise from unexpected places. Join us for an episode that truly embodies the spirit of leveling up, not just in business, but in our approach to solving society's most pressing issues.
Learn more about At Last!
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 customer-facing roles and sales in early-stage businesses, understanding burn rates, and knowing when to pivot or persevere.
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, including navigating financial transactions and implementing content moderation at scale. As PloomSocial stands at a crucial crossroads, our hosts offer valuable insights on scaling the business, emphasizing the importance of infrastructure, strategic partnerships, and maintaining a strong mission-driven focus. They also discuss the complexities of fundraising for startups and the constant need to demonstrate traction to potential investors.
This episode is a must-listen for entrepreneurs aiming to make a social impact while building a sustainable business model in the competitive world of online fundraising. Cary's candid reflections on the startup journey, coupled with Gary and Jill's seasoned advice, provide a wealth of knowledge for anyone looking to level up their entrepreneurial game.
Learn more about PloomSocial
https://www.ploomsocial.com
https://www.instagram.com/ploomsocial/
https://www.facebook.com/profile.php?id=61559422861866&mibextid=LQQJ4d
https://x.com/Ploomsocial
https://www.linkedin.com/company/ploomsocial/
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 channels, and co-packing partnerships. The conversation takes an enlightening turn as they discuss potential growth strategies, including strategic joint ventures and corporate partnerships. This episode offers valuable insights for food entrepreneurs navigating the complex landscape of retail distribution and scaling production while maintaining product quality and brand integrity. Listeners will gain practical advice on when to consider outside partnerships and how to position a niche food product for potential acquisition or investment.
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, while also offering valuable data insights to healthcare providers. The conversation touches on crucial aspects of entrepreneurship, from identifying the right customer base to maintaining focus amidst a sea of opportunities. We explore the challenges of navigating the complex healthcare ecosystem, including partnerships with insurers, employers, and medical professionals. This episode offers valuable insights for entrepreneurs in the health tech space and beyond, highlighting the importance of strategic focus, adaptability, and the power of solving deeply personal problems. Join us for a thoughtful discussion on innovation, resilience, and the potential to make a significant impact in people's lives.
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 merely a brokerage, but a multifaceted enterprise that seamlessly blends cutting-edge marketing strategies with a deep understanding of the evolving needs of the modern renter. Join us as we delve into Carlyle's unconventional approach to scaling his business, forging strategic partnerships, and reimagining the very nature of the real estate industry. In a world where the American Dream is increasingly elusive, Carlyle's Surrealty offers a glimmer of hope.
Connect with Neiman
linkedin.com/in/neiman-carlyle-815482214
instagram.com/surrealtylocating