Entrepreneur Perspectives

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 business owners about how t...

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 the question 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 years of fieldwork, 22 boxes o...

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 models and real-time police cal...

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 narrowing focus, embracing content ...

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 what it takes to build som...

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 service — and why betting eve...

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 education.

Inside This Episo...

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 his kids not to go to coll...

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 former FDNY firefighter and me...

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, working with high-profil...

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 Financial Advisory Industry”

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 the publishing process and...

“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 military families. Insp...

"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 in college, and the future ...

"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 building real leverage through ...

"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 meaningful connections.

We explore:

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 ever. He dives deep into the...

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:

1. Youth Sports Development: Gordon shares his concerns about early specialization and the emphasis on games over skill development
2. From NBA to entrepreneurship: His...