From Underdog to Entrepreneur: Building Dreams with Pat Miller

What if success wasn't about closing deals—but about eliminating the option to quit?
In this episode, real estate coach, investor, and author Josh Cadillac joins host Pat Miller to break down what it really means to build a business that lasts. From being raised in entrepreneurship at age nine, to losing everything in the 2008 crash, Josh shares how underdogs win—by outworking, outlasting, and outthinking the competition. Together, Pat and Josh unpack the mindset shifts, discipline, and systems required to turn clients into lifelong relationships and chaos into momentum.
Key takeaways include:
Why underdogs must burn the ships and remove failure as an option
How "closing customers for life" creates sustainable, compounding success
Practical systems for time management, CRM discipline, and ruthless efficiency


If you're building something from the ground up—and refusing to take the off-ramp—this conversation will remind you why underdogs win more often than anyone expects.
 
✨ Connect with Host Pat Miller
Instagram   thepatmiller11
Website     patmiller.net

What if the setback you're facing right now is actually your greatest opportunity?
In this episode, host Pat Miller sits down with entrepreneur, manufacturer, and mentor Rosemary Cescolini to unpack a powerful journey that began in teaching and evolved into building a multi-generation construction and manufacturing legacy. From learning the shop floor in a male-dominated industry to growing over 200 product designs and mentoring the next wave of entrepreneurs, Rosemary shares what it really takes to pivot, lead, and endure.
Key themes include:
Turning adversity and uncertainty into long-term advantage
Why mentorship, skilled trades, and adaptability matter more than ever
Empowering women to lead, build, and thrive without waiting for permission
If you're standing at a crossroads in your career—or wondering how to turn experience into impact—this conversation will challenge you to lift your head, stay ready, and move when opportunity shows up.
 
Connect with Rosemary:
🌐 onlywomenentrepreneurs.com
Instagram: @rosemarycescolini
@onlywomenentrepreneurs  
Tiktok only.women.entrep
FB Only Women Entrepreneurs
LinkedIn Rosemary Cescolini
LinkedIN OWE
✨ Connect with Host Pat Miller
Instagram   thepatmiller11
Website     patmiller.net

What happens when a lawyer stops thinking like a prosecutor—and starts thinking like a business owner?
In this episode, Pat Miller sits down with Damian Conforti, a former prosecutor turned trusted corporate counsel, to unpack what it really means to practice the business of law. Damian shares how relearning law through an entrepreneurial lens transformed the way he advises CEOs, founders, and leadership teams facing real-world operational and governance challenges.
Rather than just reacting to legal problems, Damian explains why the most valuable counsel anticipates risk, understands the business inside and out, and empowers leaders to make smarter decisions—before issues ever reach the courtroom.
In this conversation, you'll hear about:
Why effective legal counsel requires an entrepreneurial mindset
The difference between practicing law for businesses vs. with business leaders
How CEOs can leverage lawyers as strategic partners—not just problem solvers


If you're a founder, executive, or advisor navigating high-stakes decisions, this episode will change how you think about law, leadership, and long-term strategy. Press play and start thinking like both an owner and a lawyer.
 
 
✨ Connect with Host Pat Miller
Instagram   thepatmiller11
Website     patmiller.net

A heart attack, a bankruptcy, and a lifetime of grit pushed Dan Sachkowsky to rebuild himself—and redefine what success really means.
In this powerful conversation, Dan ("Big D") opens up about humble beginnings, multimillion-dollar wins, losing everything, and the wake-up call that turned pain into purpose. He and host Pat Miller dive deep into what it really takes to grow a business, lead with integrity, and build a life that actually matters.
In this episode, you'll learn:
How to turn adversity, setbacks, and heartbreak into fuel
Why most business owners stay stuck—and how to rise into the CEO role
The mindset shifts that create wealth, freedom, and long-term resilience


Dan's journey is a reminder that success isn't what you have—it's who you become. Lean in, get inspired, and let this episode push you toward the life you know you're meant to build.
 
Connect with Dan Sachkowsky
Website: DanSachkowsky.com
Instagram: big_dan_official
Podcast: Big D Podcast
LinkedIn: Dan Sachkowsky
Connect with Host Pat Miller
Instagram: thepatmiller11
Website: patmiller.net

What happens when life forces you to reinvent yourself?
In this episode, Pat sits down with Chris Graffagnino — Army Veteran, Purple Heart Recipient, and Founder of Graff Global — to talk about how an unexpected injury and an unshakable instinct led him from law enforcement to building an international risk management enterprise. Chris opens up about betting on himself, navigating unknowns, losing friends along the way, and why complacency is the enemy of progress.
Key Themes:
Turning adversity into opportunity
The difference between owning a business and being an entrepreneur
Reinvention, risk, and following your gut
Legacy, parenting, and building something that matters


Chris's journey is proof that the underdog can win — if they're willing to leap, learn, and keep climbing. Tune in and get inspired to take your next step.
 
 
✨ Connect with Chris Graffagnino
LinkedIn: Chris Graffagnino
✨ Connect with Pat Miller
Instagram: @thepatmiller11
Website: patmiller.net