The Jeff Fenster Show

How to Build Unbreakable Discipline & Turn Adversity Into Fuel w/ Preston Caffery

Most people talk about discipline like it’s a trendy habit. But for the best performers in the world — discipline is survival.
 
In this episode, I sit down with Preston Caffery, entrepreneur, speaker, and performance coach, to unpack the raw truth about what it really takes to build something lasting.
 
Preston shares his journey through moments of adversity that would break most people — and how he transformed those challenges into fuel.
 
We dig into:
✅ The difference between playing not to lose vs. playing to win
✅ Why most entrepreneurs fail to build lasting habits (and how to fix it)
✅ The power of environment, community, and accountability
✅ The mindset shift you need to actually do the work when no one is watching
 
This isn’t theory. It’s the blueprint Preston lives every day — and how he coaches others to do the same.
 
If you’re tired of feeling stuck, tired of waiting for the perfect time, or tired of looking for motivation instead of building discipline — listen up.

The Truth About Momentum, Mastery & Million-Dollar Relationships – with Bill Walsh

What separates the business owners who stay stuck in grind mode from those who unlock exponential momentum?
In this episode, I sit down with Rainmaker Bill Walsh — business coach to billionaires, founder of the Rainmaker Summit, and someone I personally consider a mentor — to talk about what it really takes to build wealth, relationships, and long-term success.
 
We dive into:
How to attract the right people into your life and business
The difference between hype and real value in coaching
Why most entrepreneurs stay broke (and how to break out)
The power of playing the long game and leading with service
The parenting lessons that shape how we lead at work
Why your follow-through matters more than your follow-up
 
This isn’t a fluff-filled highlight reel. This is two decades of business wisdom distilled into one hour.
 
🎁 BONUS: Stick around to hear Bill’s free gift offer to all listeners.

From Surviving to Winning: Juju Ballo on Building Unshakable Discipline & Finding Purpose in Pain

Most people want to win.
Very few are willing to become the kind of person who can.
 
In this episode, I sit down with Juju Ballo — a powerhouse of discipline, heart, and raw honesty. His journey is a masterclass in turning pain into purpose.
 
We get real about what it takes to go from survival mode to a life built with intention. No fluff, no filters — just a vulnerable conversation on how to lead yourself before you lead anyone else.
 
We talk about:
• Why most people sabotage themselves before they start
• The difference between confidence and clarity (and why you need both)
• What true discipline looks like behind the scenes
• How to take your past and make it your power
 
If you’ve ever felt stuck between where you are and where you know you’re supposed to be — this one’s for you.

Franchising Reimagined: Alex Smereczniak on Building Franzy and Empowering Entrepreneurs

In this insightful episode, we sit down with Alex Smereczniak, serial entrepreneur and co-founder of Franzy, a platform revolutionizing how aspiring business owners discover and fund franchise opportunities.
 
Alex shares his journey from launching 2ULaundry and LaundroLab—scaling them to over 100 franchise licenses—to identifying a significant gap in the franchise discovery process. This realization led to the creation of Franzy, often dubbed the “Zillow for franchising,” aiming to make franchise ownership more transparent and accessible.
 
Key Takeaways:
The challenges and triumphs of scaling franchise businesses.
How Franzy is transforming franchise discovery with AI-powered matching and transparent data.
The importance of aligning personal goals with franchise opportunities.
Insights into building a mission-driven team and company culture.
 
Whether you’re an aspiring entrepreneur or a seasoned business owner, this episode offers valuable insights into the evolving world of franchising.

Solving Real Problems, Leading Real Teams: A Masterclass with David Tal

In this powerhouse episode, Jeff Fenster sits down with serial entrepreneur and founder David Tal — former CEO of Verse.io — to unpack the real truths behind successful startups, leadership, and the future of AI.
 
From building companies that solve problems you’ve actually lived… to creating company cultures that perform like sports teams, David shares how he scaled, exited, and led with clarity and ownership. They explore the death of five-year business plans, the rise of AI-powered leaders, and what it really takes to build a high-performing company that lasts.
 
Whether you’re a startup founder, executive, or rising team member, this is the mindset shift you’ve been waiting for.

AI Agents, Privacy, and the Future of Business: Jeff Fenster x Moudy (Part 2)

In this powerful follow-up episode, Jeff Fenster welcomes back Moudy — former CTO of Shutterfly — for a no-holds-barred deep dive into the most important conversation of our time: the rise of AI and what it means for entrepreneurs, employees, and entire industries.
 
They explore how AI agents are changing the way we work, live, and think. From persistent memory and privacy concerns to risk mitigation, cybersecurity, and the rapidly accelerating pace of innovation, this episode delivers next-level insights on staying ahead in a world being rewritten by machines.
 
Whether you’re a founder, tech leader, or future-focused creative, this conversation will reshape the way you view your future.

The Future of Work: AI, Unlimited Intelligence, and Surviving the Next Revolution

In this groundbreaking episode, Jeff Fenster sits down with former Shutterfly CTO Moudy to unpack the explosive rise of AI and what it means for entrepreneurs, businesses, and everyday people. From the power of prompts and meta-prompts to the existential threat (and opportunity) AI presents, they dive deep into how technology is reshaping work, commerce, and creativity. Learn why adopting AI isn’t optional, how to future-proof your career, and why this could be the golden age for entrepreneurship.

The Truth Every CEO Needs To Hear | Emily Hayden Interview

In this powerful conversation, Jeff Fenster sits down with Emily Hayden — entrepreneur, professional bodybuilder, and transformational coach — to dive deep into personal evolution, unshakable faith, entrepreneurship, and authentic leadership.
Emily shares her journey from athletic discipline to profound spiritual growth, uncovering the keys to emotional intelligence, boundary-setting, and living in full alignment.
If you’re a founder, CEO, leader, or anyone navigating your own journey toward personal mastery, this episode is a must-listen.
 
Topics covered:
Why success isn’t about achievement — it’s about authenticity
How to build unshakable faith (even when life falls apart)
The truth about boundaries, leadership, and emotional intelligence
The secret to sustaining growth as a founder or entrepreneur
Why true coaching is about empowerment, not dependency
 
🎧 Tune in to recalibrate your mindset, realign your heart, and reignite your purpose.

How Vertical Integration Built Everbowl’s Success: The Strategy You Need to Scale

In this episode, Jeff Fenster breaks down one of the most powerful lessons behind the rapid growth of Everbowl: vertical integration.
By taking control over more parts of the supply chain, Jeff unlocked massive efficiencies, reduced risk, and fueled brand expansion.
Whether you’re an entrepreneur, startup founder, or business leader, understanding vertical integration could be the missing key to scaling smarter and faster.
 
📈 Learn:
Why vertical integration gives you unfair advantages
Real-world examples from Everbowl’s journey
How to start applying vertical thinking to your business today
 
If you’re serious about growth, you can’t afford to miss this one.

Unlocking Success, Emotional Mastery & Wealth with Shamina Taylor

What happens when you reach all your goals and still feel empty?
In this powerful conversation, Jeff Fenster sits down with Shamina Taylor—former lawyer turned 7-figure entrepreneur—to unpack the hidden emotional and energetic blocks that keep even the highest achievers stuck.
 
Shamina shares how unresolved trauma fueled her success until it left her feeling lost… and how healing, feminine energy, and self-worth became her path to abundance.
 
Whether you’re a high-performing woman, entrepreneur, or seeking deeper purpose, this episode will shift the way you think about success, money, and emotional mastery.
 
🔑 Topics covered:
Rewiring self-worth for income growth
Why women hit earning ceilings (and how to break them)
Balancing masculine drive with feminine alignment
Emotional intelligence as a business superpower
Building legacy through freedom, not hustle
 
🎁 Bonus: Message “Jeff Fenster” to @shaminataylor on IG for a free resource on increasing income with less time.