Legends N Leaders

Hosted by Ben Weiss

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679

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Oct 2026

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About the show

Our goal is to breakdown how legends and leaders achieved their success so you can become the greatest version of yourself! The path of each individual will be discussed highlighting the steps taken towards their achievement. We desire to simplify success, making it relatable, for you to take one step forward towards achievement.

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60 recent

October 17, 202628 min

From Pioneering Online Gaming to Building and Selling Tech Startups | Eric Marcoullier

What does it take to help build one of the internet's most recognizable gaming platforms and go on to launch multiple successful technology companies? On this episode of LegendsNLeaders, we sit down with Eric Marcoullier, Co-Founder of IGN Entertainment, MyBlogLog, and Gnip, to explore his entrepreneurial journey from the early days of the internet to building, scaling, and exiting technology businesses. Eric shares how he got his start in the technology industry, helping launch IGN in 1996 and turning a growing interest in online gaming into one of the internet's most influential gaming media platforms. IGN would eventually be acquired by News Corporation for approximately $650 million. Eric discusses the lessons learned from building companies, navigating failures, recognizing opportunities, and transitioning into coaching and advising startup founders.From the early internet boom to entrepreneurship, acquisitions, and helping the next generation of founders, this episode offers insights into building successful businesses and learning from the challenges along the way.

October 17, 202629 min

The Business Behind Pompa Program and the Future of Wellness | Daniel Pompa

What does it take to turn a family vision into a growing health and wellness business while building a legacy of your own? On this episode of LegendsNLeaders, we sit down with Daniel Pompa, CEO of Pompa Program and son of renowned health and wellness educator Dr. Daniel Pompa, to explore his entrepreneurial journey, the growth of Pompa Program, and his vision for the future of wellness. Daniel shares his experience stepping into a leadership role, building upon his father's work, and navigating the challenges of growing a business in the competitive health and wellness industry. The conversation explores the business behind Pompa Program, the importance of leadership and building a strong team, and how technology, marketing, and innovation are changing the way wellness companies connect with consumers. Daniel also discusses the lessons he's learned from his father, the challenges of creating his own identity as an entrepreneur, and what it takes to build a company with a lasting impact. From entrepreneurship and scaling a business to family legacy and the future of wellness, this episode offers insights into building a brand, leading a company, and pursuing a vision for long-term growth.

October 17, 202637 min

Building Hint Water: Disrupting the Beverage Industry Without Sugar | Kara Goldin

What does it take to challenge the beverage industry and build a brand that changes how people think about drinking water? On this episode of LegendsNLeaders, we sit down with Kara Goldin, founder of Hint Water, bestselling author, and entrepreneur, to explore her remarkable journey from a successful career in technology to creating one of America's most recognizable flavored water brands. After holding leadership roles at AOL and other technology companies, Kara found herself frustrated by the lack of healthy, great-tasting beverage options. Rather than accepting the status quo, she decided to create her own solution: water infused with fruit flavors, without sugar or artificial sweeteners. What started as an idea in her kitchen grew into Hint, a nationally recognized beverage brand that challenged traditional thinking about the bottled water industry. Kara shares the obstacles she faced as a first-time beverage entrepreneur, the challenges of competing against established industry giants, and the persistence required to turn a simple idea into a successful consumer business. From challenging the beverage industry to inspiring the next generation of entrepreneurs, Kara's story offers lessons in resilience, creativity, and building a brand with purpose. #LegendsNLeaders #KaraGoldin #HintWater #Entrepreneurship #BeverageIndustry #BrandBuilding #Leadership #Undaunted

October 17, 202627 min

Coaching the World's Top CEOs & Reinventing Leadership with AI | Dr. Marshall Goldsmith

What if the wisdom of one of the world's most influential executive coaches could be available to anyone through artificial intelligence? On this episode of LegendsNLeaders, we sit down with Dr. Marshall Goldsmith, world-renowned executive coach and bestselling author of What Got You Here Won't Get You There, to explore his remarkable journey, the secrets behind great leadership, and how he's bringing decades of experience into the age of AI. Having coached more than 150 major CEOs and their leadership teams, Marshall shares the lessons he's learned working with some of the world's most accomplished business leaders. He discusses what it takes to achieve lasting personal and professional growth. The conversation also explores Marshall's AI coaching tool, designed to make his knowledge, leadership principles, and coaching insights accessible to a much wider audience. Marshall discusses the potential of artificial intelligence to transform personal development and make world-class coaching available beyond the executive boardroom. From his early career and bestselling books to coaching global business leaders and embracing AI, Marshall shares his perspective on leadership, success, happiness, and building a meaningful legacy.

October 17, 202621 min

How Redbubble Changed the Way Artists Sell Their Work Online | Martin Hosking

How do you turn a simple idea into a global marketplace that empowers independent artists around the world? On this episode of LegendsNLeaders, we sit down with Martin Hosking, co-founder and former CEO of Redbubble, to explore his entrepreneurial journey, the challenges of building a global technology company, and the lessons he's learned over decades in business. Founded in 2006, Redbubble set out to give independent artists a platform to sell their designs on products ranging from clothing and accessories to home decor. What began as an ambitious startup grew into an international e-commerce marketplace, eventually becoming a publicly traded company. From navigating the challenges of scaling a two-sided marketplace to building a business that connects creativity with commerce, Martin offers insights into entrepreneurship, innovation, and long-term leadership. #LegendsNLeaders #MartinHosking #Redbubble #Entrepreneurship #Ecommerce #Startups #Leadership #Business

October 17, 202642 min

Building Tapout: From Selling T-Shirts to Creating an MMA Empire | Dan Caldwell

How do you turn a small T-shirt business into one of the most recognizable brands in mixed martial arts? On this episode of LegendsNLeaders, we sit down with Dan Caldwell, co-founder of Tapout, to explore his entrepreneurial journey, the rise of one of MMA's most iconic brands, and the lessons he learned building a business alongside the explosive growth of the UFC. Starting with a passion for mixed martial arts and a belief in a sport that had yet to reach mainstream popularity, Dan and his partners built Tapout from a grassroots apparel company into a globally recognized brand. Long before MMA became a mainstream phenomenon, Tapout was supporting fighters, attending events, and building a community around the sport. Through unconventional marketing, bold branding, and an authentic connection with athletes and fans, the company became synonymous with the rise of mixed martial arts. Dan shares the challenges of building a company from the ground up, the risks of betting on an emerging industry, and the experiences that shaped his approach to entrepreneurship and leadership. From selling shirts at MMA events to building a brand recognized around the world, Dan's story offers insights into identifying opportunities, creating a loyal following, and turning passion into a successful business. #LegendsNLeaders #DanCaldwell #Tapout #UFC #MMA #Entrepreneurship #SportsBusiness #BrandBuilding

October 17, 202634 min

The Real Story Behind War Dogs, $300M Arms Deal & Reinventing His Life | David Packouz

What happens when a 25-year-old lands a nearly $300 million government arms contract, becomes the inspiration for a Hollywood movie, and then has to completely reinvent his life? On this episode of LegendsNLeaders, we sit down with David Packouz, the real-life inspiration behind the hit movie War Dogs, entrepreneur, inventor, and Founder & CEO of Singular Sound, to explore one of the most extraordinary entrepreneurial journeys. David shares how he got his start in business, entered the world of international arms dealing, and helped secure a massive U.S. government contract that ultimately led to a federal investigation, criminal charges, and the events portrayed in War Dogs, where Miles Teller played him. The conversation goes beyond the movie, exploring how David rebuilt his life and transitioned into entrepreneurship and product innovation. He discusses creating BeatBuddy, the innovative drum machine pedal that allows musicians to control beats hands-free, and building Singular Sound into a music technology business. David also discusses War Dogs Academy, his educational venture focused on teaching entrepreneurs about government contracting, along with the lessons he's learned about identifying opportunities, taking risks, developing products, and navigating failure. From multimillion-dollar government contracts and Hollywood to inventing products and launching new businesses, this episode explores resilience, reinvention, and the entrepreneurial mindset behind David Packouz's remarkable journey.

October 17, 202631 min

From Startup to Basketball Icon: The Rise of AND1 | Tom Austin

How do you turn a startup basketball brand into a cultural phenomenon that challenges the biggest names in sportswear? On this episode of LegendsNLeaders, we sit down with Tom Austin, co-founder of AND1, to discuss the journey behind building one of the most influential brands in basketball history. Starting in 1993, AND1 set out to do something different. Rather than following the traditional playbook of major sportswear companies, the brand embraced the attitude, creativity, and authenticity of street basketball. What began as a small business grew into a global name, capturing the attention of players and fans through its distinctive products, unconventional marketing, and connection to basketball culture. Tom takes us behind the scenes of AND1's rise, from the early challenges of entrepreneurship to competing with industry giants and helping build a brand that extended far beyond the basketball court. He reflects on the decisions, risks, and lessons that shaped his career, the importance of understanding your audience, and what it takes to create a brand that people genuinely connect with. In this episode: - The entrepreneurial journey behind AND1 - How a small startup challenged the biggest brands in basketball - Building a brand that connected with an entire generation - The power of unconventional marketing and streetball culture - The challenges of scaling a sportswear company - Lessons learned from building a globally recognized brand - The lasting impact of AND1 on basketball and sneaker culture From disrupting the sportswear industry to influencing how brands connect with athletes and fans, Tom's story offers lessons in entrepreneurship, creativity, and building something that lasts. #LegendsNLeaders #AND1 #TomAustin #Basketball #Entrepreneurship #SportsBusiness #BrandBuilding #SneakerCulture

October 17, 202629 min

Building Tile, a $205M Exit & the Next Generation of Restaurant AI | Nick Evans

What does it take to build a leading technology company and then start over in an entirely different industry? On this episode of LegendsNLeaders, we sit down with Nick Evans, co-founder of Tile and co-founder and CEO of Avocado, to explore his entrepreneurial journey, the story behind creating one of the world's most recognizable Bluetooth tracking devices, and his latest venture using artificial intelligence to transform the restaurant industry. Nick helped launch Tile in 2012 with a simple mission: make it easier for people to find their lost belongings. What started as an innovative hardware startup grew into a widely recognized consumer technology brand, eventually acquired by Life360 in a deal valued at $205 million. Today, Nick is tackling a completely different challenge as the co-founder and CEO of Avocado, a restaurant technology company developing an AI-powered point-of-sale platform designed to simplify restaurant operations and help businesses run more efficiently. Nick shares the lessons he learned building Tile, the challenges of bringing physical technology products to market, and how his experience as an entrepreneur has shaped his approach to building Avocado. #LegendsNLeaders #NickEvans #Tile #Avocado #ArtificialIntelligence #Entrepreneurship #RestaurantTechnology #Startups

October 17, 202659 min

How He Founded Zappos & Revolutionized Online Shoe Shopping | Nick Swinmurn

What if one frustrating shopping experience could lead to a billion-dollar company that changed how the world buys shoes? On this episode of LegendsNLeaders, we sit down with Nick Swinmurn, Founder of Zappos, to explore the entrepreneurial journey behind one of the most influential companies in e-commerce history. Nick shares how his frustration with finding the right pair of shoes inspired him to launch Zappos in 1999, at a time when many believed consumers would never buy footwear online. The conversation explores how he got started, the challenges of convincing investors to believe in his vision, his experience building the company alongside Tony Hsieh, and the journey of turning an unconventional idea into a business that would eventually be acquired by Amazon for approximately $1.2 billion. Nick also discusses his entrepreneurial journey beyond Zappos, his involvement in sports investing, and the lessons he's learned about recognizing opportunities, building businesses, and challenging traditional industries. From entrepreneurship and e-commerce to investing and innovation, this episode offers a behind-the-scenes look at the founder who helped change the way the world shops.