High Stakes With Steve Rozenberg

Steven Rozenberg
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  • ENTREPRENEURSHIP
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Steve Rozenberg sits down with top entrepreneurs, industry experts, and high-level thinkers to uncover what really drives business success. From growth strategies to leadership insights, every episode delivers real-world advice you can apply immediately. No fluff—just practical solutions from people who’ve been in the trenches.

  1. 4D AGO

    In this High Stakes conversation, Saahil Mehta breaks down what most leaders get wrong about success

    In this High Stakes conversation, Saahil Mehta breaks down what most leaders get wrong about success. Saahil is a global entrepreneur, bestselling author, and elite leadership coach who works with founders and CEOs across 25+ countries — many running multi-million-dollar enterprises. His mission is simple but uncommon: scale without sacrifice. In this episode, we go beyond tactics and talk about the real game of leadership — clarity, decision-making under pressure, and building power without burnout. Saahil shares how navigating business across continents and summiting mountains like Kilimanjaro and Elbrus shaped his approach to peak performance and conscious leadership. We also dive into his book BREAK FREE, where he exposes the internal limits — fear, self-sabotage, and identity traps — that quietly cap most leaders long before the market does. If you’re a CEO, founder, or operator who refuses to choose between growth and fulfillment, this episode will challenge how you think, lead, and scale. 🎧 High stakes. Real leadership. Zero regrets.

    42 min

  2. JAN 14

    Today on the High Stakes Podcast, I’m joined by Brett Swarts,

    Today on the High Stakes Podcast, I’m joined by Brett Swarts, founder of Capital Gains Tax Solutions., Brett helps business owners and real estate investors defer capital gains taxes when selling highly appreciated assets. He’s the best-selling author of Building a Capital Gains Tax Exit Plan and host of the Build It to Billions and Capital Gains Tax Solutions podcasts. Brett is one of the few professionals in the world who has closed Deferred Sales Trusts, Delaware Statutory Trusts, and 1031 Exchanges. He’s closed over half a billion dollars in real estate transactions and was the first to help Bitcoin investors defer millions in capital gains taxes. Today, we’re talking about how to maximize wealth through smart real estate exit strategies.”

    40 min

  3. JAN 7

    🎙️ High Stakes with Steve Rozenberg and Mikey Taylor 🎙️

    🎙️ High Stakes with Steve Rozenberg 🎙️ Every person has a story—you just have to be willing to listen. In this episode, I sit down with Mikey Taylor to talk about failure, reinvention, leadership, and what it really takes to pivot through life’s toughest seasons. From pro skateboarder to entrepreneur, investor, and mayor, Mikey breaks down why success is built on discipline, belief, and staying in the game when things get hard. Hours of failure. Moments of doubt. One powerful mindset shift. This conversation is a reminder that failure is normal, persistence is rare, and purpose changes everything. 👉 Tune in to High Stakes and hear the full story.

    49 min

  4. 12/24/2025

    🎙️ NEW EPISODE | High Stakes with Steve Rosenberg and Jim Madrid.

    🎙️ NEW EPISODE | High Stakes with Steve Rosenberg Everyone has a story — but not everyone takes the time to truly hear it. In this powerful episode of High Stakes, Steve Rosenberg sits down with Jim Madrid, elite mental performance coach to NFL, NBA, MLS athletes and Fortune 500 companies, to unpack a life shaped by grit, belief, setbacks, and purpose. Jim shares: • Growing up in a tough Seattle neighborhood and breaking limiting beliefs • The mental fitness required to overcome massive personal and financial setbacks • How mindset shaped his work with elite athletes and top organizations • His diagnosis with stage four cancer — and the mental tools that helped him defy the odds • Why confidence, belief, and identity are the real game-changers in life and business This conversation goes far beyond sports or success — it’s about resilience, perspective, and what it truly means to live with purpose. 📘 Jim also introduces his book Meatballs & Mindset: Recipes for a Positive Life, blending mindset, culture, and life lessons in a way you won’t forget. 👉 Watch now and be reminded that anything is possible — but mindset is everything. 🔔 Don’t forget to like, subscribe, and share this episode with someone who needs this message today. ⸻ If you want, I can also: • Shorten this for YouTube Shorts • Rewrite it in a more emotional / hook-driven style • Adapt it for LinkedIn, Instagram, or podcast platforms Just tell me 👍

    44 min

  5. 12/17/2025

    Today on the podcast, Steve Rozenberg sits down with Rich Holland

    🎙️ New Podcast Episode — LIVE Today Every person you pass has a story. A past. A present. A future. Today on the podcast, Steve Rozenberg sits down with Rich Holland — a seasoned entrepreneur who’s lived through massive shifts in business and technology, from punch cards to AI, startups to exits, and reinvention after retirement. This conversation dives into: 🔥 Life lessons earned the hard way 🔥 What decades in business really teach you 🔥 Reinventing yourself when most people slow down 🔥 The stories we all carry but rarely share If you love real conversations, real journeys, and lessons that actually matter — this episode is for you. ▶️ Watch the full episode today on YouTube.

    40 min

  6. 12/17/2025

    Shift From Reactive to Intentional Ownership With Steve Rozenberg of The Rozenberg Group

    After losing his airline job in the wake of 9-11, Steve Rozenberg learned that career stability can disappear overnight. That loss fueled his drive to build a highly successful property management business that scaled to 1,000 properties and was later sold to a venture backed company. In this episode, Steve explains why many contractors are stuck in a chaotic reactive mode without clearly defined systems and processes. He also shares why proactive leadership and in person connection matter when building a company that can withstand disruption. In this episode you will learn: - What a sale date reveals about long term direction - How the dash line connects vision to ownership - Why reactive patterns quietly limit progress - What proactive leadership changes inside a company - Why in person meetings create deeper impact than online sessions Learn more about The Rozenberg Group steverozenberg.com --- 00:00 Welcome to JobTread Headquarters 01:23 Steve Rozenberg's Journey to Becoming a Coach 04:00 Building a Property Management Empire 06:53 The Importance of Vision and Leadership 10:29 Challenges and Solutions for Entrepreneurs 16:00 Reactive vs. Proactive Business Management 29:02 Common Pitfalls in Construction Businesses 32:12 The Reality of Priorities 33:11 Overcoming Fear and Doubt 33:47 The Journey of an Entrepreneur 34:21 The Importance of Systems and Processes 36:28 The Value of Coaching and Investment 39:04 Success Stories and Community Impact 49:30 The Power of Human Interaction 01:01:38 Final Advice and Contact Information --- Welcome to Builder Stories, the podcast where builders, remodelers, and contractors share their personal and business journeys. Many small to mid-sized construction businesses are great at their trades but not always equally business savvy. Come learn from the stories of successful entrepreneurs who share how they got started, how they found success, and the lessons learned along the way. Meet Your Host, Eric Fortenberry Eric is a voice and leader in the construction industry delivering education and technology solutions that are helping thousands of businesses grow and scale. He is the Founder and CEO of JobTread Software, a construction estimating and project management platform that has helped thousands of builders and contractors sell and manage over $1 billion in construction jobs. Prior to JobTread, he successfully built two other businesses, one in software and one in construction. Eric’s goal for the Builder Stories Podcast is to contribute education to the industry by sharing success stories that can help construction leaders learn and develop their businesses. Learn more about Builder Stories: BuilderStories.com

    1h 5m

  7. 12/10/2025

    🎙️ New Episode of High Stakes — and this one will move you ! Today’s guest, Bill Blankschaen

    One of the greatest gifts of this show is the reminder that every person you meet carries an extraordinary story — often one shaped by battles you never saw and victories they fought hard to earn. Today, I sit down with Bill Blankschaen — bestselling author and founder of StoryBuilders — and we open up about the chapters of life that shape us, refine us, and sometimes break us before they build us. This episode is about resilience, purpose, and finding meaning in the moments that test you the most. If you’re in a season of uncertainty… if you’re rebuilding… if you’re trying to remember why you started… This conversation is for you. Tune in. Let it remind you: your story isn’t over — you’re just entering your next chapter. ✨

    45 min

  8. 12/03/2025

    🎙️ NEW EPISODE: High Stakes with Steve Rozenberg and Lance Mortlock

    One of the reasons I love hosting this show is simple — it allows me to meet fascinating people, hear their stories, and learn from their experiences without traveling the world to do it. Technology gives us access to brilliant minds we’d never cross paths with otherwise. Today’s guest is Dr. Lance Mortlock — a professor, managing partner at EY, bestselling author, mountaineer, and proud husband and dad. But what stood out most wasn’t the résumé… it was the journey behind it. 👉 As a kid, his teachers told his parents he’d “never amount to anything.” 👉 He failed repeatedly — including climbing a major peak FIVE times before reaching the summit. 👉 He built a career around strategy, resilience, curiosity, and doing the hard things most people avoid. We talked about: • How small daily wins can pull you out of the hardest seasons • Why failure teaches more than success ever will • How strategy differs from tactics (and why most entrepreneurs confuse the two) • How AI is reshaping business models faster than leaders can adapt • Why businesses that execute relentlessly will win the future If you’re building a business, navigating uncertain times, or searching for motivation to keep going, this episode is packed with insights you’ll want to hear. 🎧 Tune in — this conversation might be the shift you need today.

    41 min
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4.9
out of 5
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About

Steve Rozenberg sits down with top entrepreneurs, industry experts, and high-level thinkers to uncover what really drives business success. From growth strategies to leadership insights, every episode delivers real-world advice you can apply immediately. No fluff—just practical solutions from people who’ve been in the trenches.

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