Legends N Leaders

Hosted by Ben Weiss

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601

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Aug 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

August 22, 202618 min

Natraj “Raj” Balasubramanian: From Fighter Pilot to Public-Market AI CEO

Natraj “Raj” Balasubramanian, Founder & CEO of Braiin Limited, joins LegendsNLeaders to share an extraordinary journey spanning military aviation, entrepreneurship, drones, enterprise software, and artificial intelligence. Raj began his career as a fighter pilot in India, flying MiG-21s and MiG-27s before surviving an ejection from a MiG-27—an experience that ultimately helped set him on an entirely new path in the United States. After transitioning into enterprise software, he built and scaled an ERP company to approximately $35 million in revenue before exiting in 2011. From there, Raj moved into commercial drones, exploring applications across agriculture, search and rescue, delivery, and infrastructure in emerging markets throughout Asia and Africa. He later expanded into generative AI, ultimately building Braiin into a multi-sector AI platform company applying machine learning and automation across agriculture, customer experience, real estate, and other traditional industries. In this conversation, we discuss surviving high-stakes environments, reinventing yourself as an entrepreneur, building and exiting companies, taking Braiin public, and Raj’s perspective on where AI and automation can create the greatest real-world impact.

August 22, 202624 min

Eric Girouard: Building BRUNT Workwear Into a $300M+ Challenger Brand

Eric Girouard, Founder & CEO of BRUNT Workwear , joins LegendsNLeaders to share how he built one of the fastest-growing brands in workwear by focusing on a customer he believed legacy companies had overlooked: America’s tradespeople. Growing up in a blue-collar household, Eric started roofing at 14 and running a landscaping business at 15 before eventually building a career in e-commerce and footwear. Years later, conversations with his childhood friends in the trades sparked the idea for BRUNT—a modern workwear company built around direct feedback from the people actually wearing its products. In this conversation, Eric breaks down the journey from leaving his job and launching BRUNT in 2020 to scaling the company across work boots, apparel, direct-to-consumer, wholesale, and physical retail. We discuss product development, community-driven branding, customer obsession, competing against heritage companies, and why listening to workers instead of industry insiders became one of BRUNT’s biggest advantages. Eric also shares the lessons behind building a brand that has, since recording this episode, grown to hundreds of millions of dollars in sales, the mistakes and failures along the way, and what it takes to turn an underserved customer base into a powerful community and category-defining business.

August 22, 202624 min

Darren Prince: Representing Legends, Building an Empire & Overcoming Addiction

Darren Prince, Founder & CEO of Prince Marketing Group, joins LegendsNLeaders to share his remarkable journey from teenage entrepreneur to one of the most connected sports and celebrity agents in the business. Darren started selling baseball cards at just 14 years old and became a self-made millionaire by 20 before building Prince Marketing Group. Over his career, he has represented and worked with some of the biggest names in sports and entertainment, including Magic Johnson, Muhammad Ali, Joe Frazier, Hulk Hogan, Ric Flair, Dennis Rodman, Larry Bird, and many others. His agency says it has negotiated more than $500 million in deals over its history. In this conversation, Darren breaks down how he built relationships with global icons, what separates great agents from everyone else, the business behind celebrity endorsements and licensing, and the lessons he has learned from decades of negotiating deals at the highest levels of sports and entertainment. We also dive into the deeply personal side of Darren’s story—his battle with addiction while operating at the height of his career, his path to recovery, and why he now uses his platform to help others struggling with addiction and mental health. From working alongside legends to hitting rock bottom and rebuilding his life, Darren shares a powerful perspective on relationships, resilience, success, and what truly matters when the deals and celebrity names are stripped away.

August 22, 202622 min

Nik Shevchenko: Selling Two Startups, Becoming a Thiel Fellow & Building the Future of AI

Nik Shevchenko joins LegendsNLeaders to share his unconventional journey from mining cryptocurrency as a teenager to becoming a serial entrepreneur, Thiel Fellow, and founder working at the forefront of AI and wearable technology. Nik started his first company at 16 and sold it by 18. At 19, he joined 500 Startups and went on to build WeLoveNoCode, which he later sold to Toptal. Today, he’s working on Omi, an AI wearable designed to bring artificial intelligence into everyday life. In this conversation, Nik breaks down what he learned from building and selling companies at such a young age, raising capital, moving quickly as a founder, and recognizing emerging technology trends before they become mainstream. We also dive into the future of AI hardware, robotics, wearables, entrepreneurship, and Nik’s ambitious view of how technology could fundamentally change the way we work and live.

August 22, 202620 min

Bryan Smiley: Building the Future of Sports Media With Stephen Curry

Bryan Smiley, CEO of Hard Carry Media and former President & Chief Content Officer of Hartbeat, joins LegendsNLeaders to discuss how the next generation of sports media is being built. Bryan breaks down Hard Carry Media’s new joint venture with Stephen Curry and Erick Peyton’s Unanimous Media, designed to create digital-first sports content around NIL athletes, creators, and the changing way Gen Z consumes sports. We dive into why athlete storytelling is shifting from traditional media to YouTube and social platforms, how NIL is changing fandom, what makes a digital format scalable, and how successful creator-led IP can grow from social content into major streaming and television franchises. Bryan also shares lessons from his career in Hollywood and at Hartbeat and why he believes the future of sports entertainment will be driven as much by personality and format as by what happens on the court.

August 22, 202621 min

Kristine Shine: What It Really Takes to Reach the C-Suite

Kristine Shine, founder and CEO of Shine Talent, joins LegendsNLeaders to share lessons from more than two decades of leadership across some of the biggest names in media and technology. From leadership roles at Microsoft to becoming the founding CRO of POPSUGAR and later President of the San Francisco Chronicle, Kristine has experienced firsthand what it takes to build teams, transform businesses, and lead through periods of rapid change. Now, as the founder of Shine Talent, Kristine helps executives and companies reach their potential. She breaks down the leadership habits that accelerate careers, the mistakes that hold talented people back, and how the expectations of great leaders are changing in the age of AI. Kristine also shares her perspective on: Why talented executives can still get stuck in their careers When taking a strategic risk can change your trajectory What she looks for when evaluating high-potential leaders How the skills required to reach the C-suite differ from those required to succeed once you’re there

August 21, 202623 min

Harry Gestetner: Building the Future of Sleep With AI

Harry Gestetner, founder of Orion Sleep, joins LegendsNLeaders to discuss his journey from building and selling creator platform Fanfix to tackling one of the biggest opportunities in health and longevity: sleep. His latest company, Orion, has developed an AI-powered smart mattress cover that tracks biometrics and automatically regulates temperature throughout the night to improve sleep. Harry shares how his own struggles with sleep and health pushed him toward the longevity space, what he learned from building companies at a young age, and why he believes technology can fundamentally change how we recover and perform. Harry also dives into: Why founders should think about themselves like athletes Going from Fanfix to building a health-tech company Raising $17.5 million to pursue Orion’s vision Why sleep could become one of the biggest consumer health categories

August 21, 202625 min

Eric “ET” Tecosky: Turning a Bartender’s Problem Into Dirty Sue

Eric “ET” Tecosky, founder of Dirty Sue, joins LegendsNLeaders to share how a frustrating problem behind the bar turned into a completely new cocktail product. After years as a Los Angeles bartender, ET asked a simple question: why wasn’t anyone making premium bottled olive juice specifically for dirty martinis? That idea eventually became Dirty Sue. ET breaks down the journey from developing the product and filling early orders out of his apartment to building a recognizable cocktail brand. The conversation dives into spotting opportunities others overlook, creating a category around a niche idea, and the persistence required to turn a simple solution into a lasting business. ET also shares his perspective on: Why some of the best business ideas come from everyday frustrations Building a brand without following the traditional startup playbook The power of owning a specific niche Lessons from years behind the bar and as an entrepreneur Why product quality and consistency have remained central to Dirty Sue

August 21, 202621 min

Eirik Holth: The Change The Coffee Industry Needs

Black Sheep Coffee co-founder Eirik Holth joins LegendsNLeaders to share the journey of building one of the most exciting challenger brands in the global coffee industry. After leaving a career in private equity, Eirik took the leap into entrepreneurship and helped launch Black Sheep Coffee with the ambition of doing things differently in a market dominated by global giants. In this episode, Eirik breaks down the early days of the company, the realities of scaling a consumer brand, expanding internationally, building a strong culture, and the lessons he’s learned from more than a decade of entrepreneurship. Eirik also shares his perspective on: Why being an outsider can be an advantage What founders underestimate about scaling The mindset required to keep building when things don’t go according to plan

August 21, 202621 min

The Factory of the Future Won’t Look Like a Factory | Machina Labs CEO Ed Mehr

What happens when AI, robotics, and manufacturing converge? In this episode of LegendsNLeaders, I sit down with Ed Mehr, Co-Founder & CEO of Machina Labs, to explore his vision for the software-defined factories of the future. A former SpaceX and Relativity Space engineer, Ed is building a radically different approach to manufacturing—using intelligent robots, AI models, and flexible production systems to create complex parts without traditional fixed tooling. We discuss the future of American manufacturing, AI-powered robotics, lessons from SpaceX, and how software-defined factories could transform industries ranging from aerospace and defense to automotive and construction. The next industrial revolution may not be about building bigger factories. It can be about making factories programmable. #AI #Robotics #Manufacturing #MachinaLabs #SpaceX #FutureOfManufacturing #Automation #LegendsNLeaders