#276: Connor Steinbrook — 4X World Series of Poker Champion Builds a Real Estate Empire
Release Date: 11/17/2025
MIKE'D UP!
In this powerful episode, Mike welcomes , former corporate VP, resilience alchemist, author, and endometriosis advocate, for a conversation centered on transforming pain into purpose. Originally from Moldova and educated at UCLA and University College London, Katya spent 15 years in global talent management before a life-altering health journey redirected her calling. During the pandemic, Katya confronted chronic pain, anxiety, and body dysmorphia, eventually receiving a long-overdue diagnosis of endometriosis, a condition affecting millions of women worldwide yet still widely...
info_outlineMIKE'D UP!
In this episode, Mike takes listeners behind the scenes of a few of MIKE’D UP’s most impactful moments of 2025—a year defined by resilience, truth, healing, courage, and unapologetic self-belief. From life-altering diagnoses to near-death experiences, from entrepreneurship’s darkest days to moments of profound clarity, this episode stitches together the stories that didn’t only inspire—but changed lives. You’ll hear from guests who refused to accept limits, questioned what they were told was “impossible,” and chose purpose over fear. These conversations aren’t motivational...
info_outlineMIKE'D UP!
This week Mike sits down with entrepreneur —a man who transformed a life-altering setback into a multimillion-dollar comeback. Chuck’s journey begins with a single decision that landed him in prison after he refused to testify against friends in an illegal sports-betting case. But it was in a prison cell on Thanksgiving Day where he experienced the wake-up call that reshaped his entire life. From that moment, accountability became his superpower. Chuck rebuilt everything from the ground up. He went on to close over $200 million in commercial real estate deals, mastering the...
info_outlineMIKE'D UP!
In this inspiring episode, Mike sits down with , co-founder of , to explore how real national healing starts with one simple idea: choose positivity, then pass it on. After leaving a 20-year private equity career, Adam dedicated himself to bridging America’s divides through service, storytelling, and connection. He shares how the Sheriff Unity Network, now active in over 100 counties, is quietly strengthening communities by addressing issues like mental health, addiction, homelessness, and everyday public trust—often in ways most people never see. Adam brings this mission to life...
info_outlineMIKE'D UP!
This week, Mike is joined by , CEO and Founder of , for a sharp, energizing look at what it really takes to lead in today’s tech world. With more than 20 years of software experience and over $30 million raised across five startups, Ben brings the hard-earned lessons only a seasoned builder can offer. Ben breaks down the traits of effective tech leadership—setting a clear vision, empowering teams, and avoiding micromanagement. He shares candid stories from his early days as a founder, including a memorable misunderstanding of “burn rate.” He explains why learning to speak the...
info_outlineMIKE'D UP!
In this powerful episode, Mike welcomes back —author, storyteller, and transformation strategist—to explore the ideas behind her latest book, Through honest conversation and deep insights, Laura reveals why reinvention isn’t a destination but a lived journey shaped by every experience, every pivot, and every scar earned along the way. Together, Mike and Laura unpack the beauty of our personal origin stories and the quiet, unseen moments that shape who we become. Laura invites listeners to look beyond the myth of perfection and instead embrace the raw, unfiltered truth of their...
info_outlineMIKE'D UP!
Note: Connor was a 3X World Series of Poker champion when this episode was recorded, and hours before his birthday earlier this month, he won his 4th World Series of Poker circuit championship! When life dealt him a losing hand, didn’t fold. He went all-in and stormed back. In this episode, Mike welcomes back four-time World Series of Poker champion turned real estate powerhouse to uncover how one man went from the chaos of online poker shutdowns to leading one of eXp Realty’s most dominant teams— Connor’s story plays out like a classic comeback movie: a sudden crash, a crisis of...
info_outlineMIKE'D UP!
This week, Mike sits down with , the founder and President of , a thriving $5 million e-commerce company that powers over 1,000 online swag stores for brands like DoorDash, Crocs, and Penn Entertainment. Jay opens up about his turbulent journey—from explosive early success and devastating loss to rebuilding his life and business from the ground up. The conversation explores Jay’s struggle with gambling addiction, the painful collapse of his first ventures, and how entering recovery became the foundation for lasting personal and professional transformation. He shares how humility,...
info_outlineMIKE'D UP!
This week, Mike sits down with , an Emmy-winning journalist who spent nearly three decades at NBC New York. From her humble beginnings in a small Minnesota town to becoming a prominent voice in television journalism, Jane reflects on a career filled with powerful storytelling, resilience, and transformation. Jane opens up about covering pivotal events like 9/11, the emotional weight of live reporting, and the moment she realized it was time to pivot from broadcasting to coaching. Today, she empowers entrepreneurs, executives, and women to master the art of authentic...
info_outlineMIKE'D UP!
In this moving and eye-opening conversation, Mike sits down with Kurt Avery, the visionary founder and president of , to explore how one man’s faith, resilience, and entrepreneurial drive sparked a movement that’s transforming global health. After leaving the corporate comfort of Fortune 500 marketing, Kurt took a leap of faith to create a company focused on a single, world-changing mission—to provide safe, clean water to every person who needs it. In this episode, we journey through the challenges and triumphs that shaped Sawyer’s path—from early financial hardships and failed...
info_outlineNote: Connor was a 3X World Series of Poker champion when this episode was recorded, and hours before his birthday earlier this month, he won his 4th World Series of Poker circuit championship!
When life dealt him a losing hand, Connor Steinbrook didn’t fold. He went all-in and stormed back.
In this episode, Mike welcomes back four-time World Series of Poker champion turned real estate powerhouse to uncover how one man went from the chaos of online poker shutdowns to leading one of eXp Realty’s most dominant teams—The Wolf Pack.
Connor’s story plays out like a classic comeback movie: a sudden crash, a crisis of identity, and a rediscovery of faith, discipline, and purpose that sparked an empire. He reveals how the skills that made him elite at the poker table—emotional control, precision under pressure, and relentless focus—became the foundation for scaling one of the largest and fastest-growing real estate groups in North America.
But this episode isn’t only about business, it’s about the inner game. Connor breaks down his signature 10-45-45 Rule of Communication, showing why energy and emotion speak louder than words. He opens up about building mental clarity through visualization, solitude, and faith, and why mastering your mindset is the ultimate key to success.
IN THIS EPISODE:
💥 All In on Faith: How Connor Turned Collapse Into a Multi-Million Dollar Comeback
🧠 The Inner Game of Success: The Poker Mindset That Built One of eXp’s Fastest-Growing Teams
🛠️ From Rock Bottom to Wolf Pack: Rebuilding Life and Business Through Discipline and Belief
🚀 The 10-45-45 Rule: How Energy, Emotion, and Focus Drive Elite-Level Communication and Leadership
📘 BONUS TAKEAWAY:
Connor’s greatest win isn’t measured in chips or commissions—it’s in mastering himself. His story is a powerful reminder that the real game is played within. When you learn to control your thoughts, guard your faith, and stay disciplined through the losses, you create a foundation that no setback can shake. Success, as Connor proves, begins long before the results show—it starts the moment you decide to go all in on yourself.
🚀 PERFECT FOR:
Entrepreneurs, real estate pros, poker fans, and anyone who’s ever wondered how to turn failure into fuel. If you’ve ever been knocked down and dreamed of a comeback—this episode is your playbook.
Resources Mentioned in This Episode:
Napoleon Hill’s 17 Principles of Personal Achievement
Connect with Connor:
Connect with Mike:
SPONSORS:
Social Chameleon | Transform Your Podcast
AFFILIATES:
Libsyn: First Month FREE with Promo Code BEGREAT
Riverside | This interview was recorded on Riverside
Want to become a show sponsor or affiliate? Email mike@socialchameleon.us
Copyright © 2025 Mike’D Up! with Mike DiCioccio | For permission to use this content in any way, please email mike@socialchameleon.us