Entrepreneur Perspectives

Brando Babini started a company at 16 because the thing he needed didn't exist. Five years later he's running it from a train seat between Brown and Brooklyn — 1,000 players, a Nike partnership, and 30 million views he shot and edited himself. This one's about how he actually does it. Brando is 21, still finishing his degree, and building Youth 4 Youth FC into one of the largest player-led soccer...

Why NIL needs data, why athlete brands matter, and how college sports is becoming a marketing business. College sports is moving fast. NIL, revenue sharing, transfer rules, donor fatigue, social media, compliance, brand deals, and athlete value are all colliding at once. Brent Wall, founder and CEO of Student Athlete Score, joins Eric Kasimov to talk through what is actually happening in the NIL m...

Why youth sports are chaotic, why parents carry the load, and how Onsides is trying to make it easier. Youth sports is not just practices, games, and tournaments anymore. It is schedules, apps, travel, training, equipment, group chats, recruiting pressure, and a lot of parents trying to keep up. Dave Yoo, founder and CEO of Onsides, joins Eric Kasimov to talk about the problem his company is tryin...

When NIL opened up, everyone rushed to build the marketplace — collectives, payment vehicles, deal flow. Nobody asked who the athlete actually was or what they'd do when the money hit. Stephen Bienko, former Air Force Academy and Villanova athlete and founder of 42U, has been inside college athletics long enough to see what got left behind. This conversation covers the transfer portal, soft skills...

Zero tolerance for compromise doesn't mean being harsh — it means being clear. Dave Selinger explains how military mentors shaped his leadership philosophy, why "left of bang" became the foundation of Deep Sentinel's approach to crime prevention, and how you can hold absolute standards while still managing people like human beings. Key Takeaways "Left of bang" — the military concept of intervening...

What 50 years in insurance teaches about relationships, change, and why the basics still matter. In Episode 1 of The Long Game, Mitch Long sits down with Wes Connor to talk about how he got into insurance, what kept him in it, and what 50 years in the business has taught him. They get into family business, remote selling, hiring challenges, commercial and personal lines, and why life insurance sti...

Why stories beat pitches, why showing up still matters, and what this series is about. Eric Kasimov sits down with Mitch Long to kick off The Long Game. Mitch has been in the insurance business for over 30 years. He started with a pager and a roll of quarters. He built his book by showing up every Tuesday until people just started handing him the business. Now he's here to have conversations with...

The Truth About Admissions, Debt & AI’s Role in the Future of Higher Ed College costs are soaring, mental health struggles are rising, and the path to success looks more uncertain than ever. In this conversation, Eric Kasimov talks with Senan Khawaja, Co-founder and CEO of Kollegio, an AI-powered platform helping students and universities rethink the college admissions process. They explore th...

Bob Knakal is a legendary figure in New York commercial real estate, known for his data-driven territory model, massive deal volume, and unapologetically old-school work ethic. As the founder of Massey Knakal Realty Services (sold for $100M) and now Chairman at BKREA, Bob has shaped both the skyline of NYC and the next generation of real estate professionals. In this episode, Bob shares how 40 yea...

David Selinger (aka “Selly”) is the founder and CEO of Deep Sentinel, a security company blending AI with live human monitoring to stop crime in real time. From Amazon to Redfin to AI security, Dave Selinger has built a real-time protection system now scaling fast with $15M in Series B funding from top investors. In this episode, Selly breaks down how Deep Sentinel works—from crime prediction mode...

Blake Harris is the founder of Blake Harris Law, the largest exclusively offshore asset protection law firm in the United States. With a team spread across four continents, Blake has built a niche global practice helping high-net-worth individuals legally protect their assets through Cook Islands trusts and other offshore strategies. In this episode, Blake breaks down how his firm grew by narrowin...

Senan Khawaja is the Co-founder and CEO of Kollegio, a startup using AI to bring personalized college and career guidance to every student, not just those who can afford it. He’s also a recent Stanford grad who’s thinking hard about how higher ed needs to change. In this episode, we talk about the messy reality of the college application process, the future of mentorship in an AI-driven world, and...

Scott Sheridan is the CEO of Tastytrade, a trading platform and brokerage he co-founded with longtime partner Tom Sosnoff. Together with their amazing team, they’ve built a trading and media empire using a counterintuitive strategy: giving away their best content for free. In this episode, Scott explains how their “goodwill model” works — from free education on Tastylive to transparent customer se...

Dr. Shalabh Gupta is the founder of Unicycive, a biotech company working to simplify treatment for dialysis patients. He’s also a physician, former Genentech executive, and someone who thinks deeply about careers, leadership, and the role of AI in healthcare. In this episode, we cover the problem of pill burden, how to reverse engineer your career, and what most people misunderstand about medical...

Conifer co-founder Ankit Somani left Google to build something with more heart — and fewer rare-earth magnets. Backed by a $20M seed round, Conifer is making electric motors that are clean, compact, and don’t rely on China-controlled materials. In this conversation, Ankit talks about the problem they’re solving, what it’s like building real hardware in a software-driven world, and why he’s telling...

Two men talking about fatherhood, presence, and managing expectations. This isn’t a blueprint. It’s a conversation. Vin Infante has strong views — on work, fatherhood, therapy, homeschooling, entrepreneurship, and what it means to show up as a man. You might not agree with all of it, but that’s the point. These are the kind of conversations that surface things many won’t say out loud. Vin is a for...

With early backing from OpenAI CEO Sam Altman and a $40M Series A led by Framework Ventures and Polychain Capital, Meanwhile is revolutionizing life insurance with Bitcoin-denominated policies. Co-Founder Zac Townsend explains how digital currency and modern tech are making life insurance more accessible — while solving the industry’s legacy system problems. Zac also shares insights on fundraising...

In this episode, Eric talks with Joe Cantanucci, CEO and Founding Partner of AdvisorLink, about today’s rapidly changing financial advisory industry. With 25 years of experience, Joe shares practical insights on how remote work is reshaping productivity, mentorship, and client relationships in a field that is about to experience the Great Wealth Transfer. What We Cover in “Remote Work in Today’s F...

In this episode, Eric talks with Yehuda Niv, Founder & CEO of Spines, an Israel-based AI-based book publishing platform that’s transforming how authors publish their work. From his early recognition of AI’s potential to his mission of helping one million authors get published, Yehuda shares his vision for democratizing the publishing industry. What We Cover: How Spines uses AI to streamline th...

“I don’t think military spouses want charity. I think they just want the opportunity to provide for their families or stay connected to something consistent.” – Lisa Bradley When Lisa Bradley and her co-founder Cameron Cruse, both military spouses, started R.Riveter in 2011, it wasn’t just about making handbags—it was about creating opportunity, community, and a way to honor the resilience of mili...

"AI is awesome, and it provides many opportunities for advancement in different sectors. Where I find it gets tricky is where a lot of people, especially when it comes to content creation, leverage AI to replace the humanness of content." - Madeleine Lambert Madeleine Lambert, Director of Marketing and Sales at Originality.ai, shares insights on AI content detection, digital ethics, essay writing...

"The tools of learning are abundant. Desire to learn is scarce." - Naval Ravikant When Eric Jorgenson discovered Naval Ravikant's work as a young entrepreneur, it changed his life. Years later, he's turned that inspiration into tangible impact — writing a book that's helped millions understand Naval's principles, running a global publishing company that's changing how people create books, and buil...

"I think art saved my life." - Jodie King In this episode, Eric talks with professional artist and educator Jodie King about discovering the healing power of art, building an authentic creative practice, and helping others reconnect with their artistic spirit. With 20 years of experience as an artist and entrepreneur, Jodie shares insights on using creativity to process emotions and build meaningf...

Eric chats with Robin Daniels, Chief Business and Product Officer at Zensai. An episode on developing soft skills and working with AI. Robin brings incredible energy and wisdom to this engaging conversation. Drawing from his 20+ years of executive experience at companies like Salesforce, LinkedIn, and Box, Robin explores how AI is reshaping the workplace while making soft skills more vital than ev...

In this episode, Eric chats with NBA All-Star Gordon Hayward about his transition from professional basketball, his thoughts on youth sports in America, and his new ventures, including Form (a basketball training tool) and his movie "Notice to Quit." We go over: Youth Sports Development: Gordon shares his concerns about early specialization and the emphasis on games over skill development From NBA...