High Stakes With Steve Rozenberg

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 pro...

🎙️ 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...

🎙️ 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 n...

🎙️ 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 🔥...

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...

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...

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 a...

a serial entrepreneur, husband, father of four, and someone who’s taken some of life’s hardest hits — and turned them into fuel. We talked about: 💥 The “stories behind the strangers” we walk past every day 💥 The dark + light side of the entrepreneurial mind 💥 How distraction destroys potential 💥 The pivotal moments that completely redirected Justin’s life 💥 Addiction, rock bottom, and the roa...

Podcasting isn’t just content — it’s the ultimate networking cheat code. 🎙️🔥 Steve Rozenberg sat down with creative agency founder Jake Isham to talk about why podcasting has become the most powerful way to build authority, create authentic connections, and open doors you didn’t even know existed. From branding to authenticity to the real journey behind entrepreneurship, this episode dives deep i...

We walk past thousands of people every day — but do you ever wonder about their story? In this episode, I sit down with Kevin Hubschmann, founder of Laughed Out Events, to talk about how laughter, authenticity, and self-awareness can transform company culture — and your life. From stand-up stages to boardrooms, Kevin shares how humor builds trust, boosts performance, and helps leaders connect on a...

bold decisions fueled his journey to success! Steve Rozenberg sits down with Dave Seymour — a private equity entrepreneur whose journey from firefighter to real estate success will inspire anyone chasing transformation. 🔥 From financial struggle to freedom, Dave shares powerful insights on: • Turning pain into pivotal moments for growth • Making life-changing decisions with courage and faith • Re...

This week on High Stakes with Steve Rozenberg: I sat down with @matthewteifke — 16+ years in real estate, partnered on huge deals, worked with Cardone… and he tells the truth most people hide. We talked about: • Losing $4M of his own money • Almost breaking mentally, financially, and as a husband/father • Tying your identity to money — and what happens when it’s gone • Why entrepreneurs can’t stop...

🎙️ New Podcast Episode Alert! Today, we’re thrilled to welcome Phil Kornachuk — a true leader, coach, and former U.S. Army veteran — to our podcast! 🇺🇸 Phil shares powerful lessons on leadership, discipline, and mental resilience, drawing from his real-world experience leading teams under pressure and helping others unlock their potential. If you’re ready to level up your mindset and lead with pur...

From selling gumballs in 8th grade to owning 48 rental properties, running multiple businesses, and employing 65+ people, Sam’s journey is pure grit, hustle, and heart. 💥 In this powerful conversation, Sam opens up about: • His early drive as a young entrepreneur • Lessons from the military and law enforcement that shaped his work ethic • How he flipped his first duplex with a Home Depot book bef...

🎙️ New Episode Alert! In this week’s episode of The High Stakes Podcast with Steve Rozenberg, we sit down with Alex Osenenko — a serial entrepreneur, systems builder, and co-founder of ArchIT, a specialized IT services firm helping design and construction companies grow without tech headaches. Alex is also the founder of Catch Happy, a lifestyle brand celebrating outdoor life, resilience, and the...

🌟 Authentic Leadership & Human Connection 🌟 What truly matters in business and in life? Not the titles, not the slides, not the noise. It’s the moments when you bring your real self to the table—whether that’s showing vulnerability, pushing through challenges, or refusing to quit when things get tough. Joe Davis shares powerful lessons from decades of leadership: 💡 Success isn’t just about...

🌍 Whatever business we’re in, we’re truly in the relationship business. 🤝 It’s all about connecting, conversating, and solving real problems. In this week’s episode, Steve sits down with Connor Doyle, a marketer living in Bali who helps contractors level up their online presence. From law school to digital nomad, Connor’s journey is one you don’t want to miss. 🎧 Tune in on Apple Podcasts and Sp...

🚀 New Episode of High Stakes with Steve Rozenberg 🎙️ This week, Steve sits down with Adam Charlton, Senior Direct Marketing Coach at REI Printmail. From conferences to powerful conversations, this connection sparked ideas on data-driven direct mail, AI-powered targeting, and the art of creating campaigns that actually work. 📬 Why does direct mail still matter in 2025? 🤝 How to know your ideal c...

🔥 From selling RVs 80+ hours a week to building million-dollar sales teams — Adam McCombes shares his journey of sacrifice, faith, and transformation. ➡️ Tune in to hear how he went from burnout at a dealership to thriving in marketing and sales, helping businesses scale with real impact. 🎧 Don’t miss this inspiring episode!

Sales expert Tony Varga shares how to build high-performing sales teams that actually close! Don’t miss it. At Mach 5, Tony Varga will dive deep into the art of sales—how to frame conversations, handle objections effectively, and build scalable sales teams that thrive. His approach isn’t about pressure or manipulation, but about serving, guiding, and helping clients make confident decisions. Don’t...

🔥 NEW EPISODE OUT NOW! This week we’re joined by Tony Flattum—a powerhouse in roofing and real estate. From: 👉 Knocking doors To: 👉 Owning doors & building wealth This episode is packed with gold for anyone serious about building a business AND a legacy. 💰 🎧 Listen now. #PodcastDrop #TonyFlattum #BusinessAndWealth #EntrepreneurLife

From surviving adversity to achieving entrepreneurial mastery, Jason has built, scaled, and exited 26 businesses—not by accident, but by design. As the founder of the Built to Exit (B2X) system, Jason helps business owners design their exit—on their terms, for top dollar, and with freedom intact. He’s also deeply committed to making a difference: tackling domestic violence, human trafficking, and...

Ashley Wilson has worn many hats: 👩‍⚕️ Director in Big Pharma 🏠 High-end real estate investor 💼 Commercial developer 📚 Author & national speaker 💻 Tech founder What looks like a zigzag career on the outside is actually a strategic path fueled by self-awareness, grit, and purpose. In this episode, Ashley dives deep into: 🔹 Why she left a top role in corporate pharma 🔹 The mindset shift f...

With 25+ years in the building materials industry, Grady Ashley knows what it means to lead from the front — in business and in life. From building culture-driven teams to raising a family of five, Grady brings real leadership lessons from the trenches. In this episode, we dive into: 🧠 The mindset it takes to truly lead 💬 Why listening is your most powerful leadership tool ⚡️ How to motivate ev...

Host Steve: "You're not gambling money, but you're gambling the most valuable asset you have, which is your time." How do you make sure you're not just creating a job for yourself, but building a real business? Our guest Eric Fortenberry (@ericfortenberry) is obsessed with this question. After selling his first software company, he saw brilliant contractors stuck in chaos, unable to scale past a c...