How do you build a business that serves your life instead of running it? In this episode, Theresa sits down with Jason Phillips, the award-winning entrepreneur behind Phillips Home Improvement and Contractor Freedom, for a masterclass in building a business from the ground up.

Jason shares his incredible story of starting a painting company with just a few dollars, driven by a desire to do better for customers and employees. He reveals the pivotal moment that transformed his entire approach to business—a moment that led him from being bankrupt on time to designing a life of freedom.

Discover Jason's powerful "SOS" framework—Self, Others, Systems—a practical guide for any business owner feeling stuck. You'll learn the importance of starting with your own leadership, building a team that carries the vision (not just the workload), and implementing systems that create predictability and profit. Jason also opens up about how his faith shapes his people-first business philosophy and why doing the right thing is always the most profitable path.

If you're an entrepreneur, leader, or anyone feeling trapped in the "messy middle" of your business, this conversation is packed with wisdom to help you build a company that fuels your life's purpose.

Topics Covered:

• From Broke to Blessed: The Entrepreneurial Journey
• The "SOS" Framework: Self, Others, Systems
• Building an Oak Tree Team vs. a Weeping Willow
• The Power of DISC in Hiring and Leadership
• Balancing People and Profits for Sustainable Growth
• Designing Your Business as a "Freedom Machine"

Connect with Jason:
Facebook: Contractor Freedom
Instagram: @contractorfreedomlive
Website: phillipshomeimprovement.com

Subscribe to The UPside Podcast:
Don't miss an episode! Subscribe for your weekly dose of inspiration to get unstuck and elevate your thinking.

Connect with Theresa:
Website: theresaflood.com

Are you ready to stop the cycle of starting strong and burning out? In this episode of TheUPside Podcast, host Theresa Flood is joined by life and business coach Michelle Ozymy to discuss the real secret to achieving your goals: mastering your habits.

Forget about intense, short-lived efforts. Theresa and Michelle dive into the psychology behind why we stick to bad habits and how to build good ones that last. Discover practical strategies like "habit stacking" from the bestselling book Atomic Habits and learn why consistency will always beat intensity. This conversation is packed with actionable advice on how to shift your identity, overcome complacency, and become the person who keeps promises to themselves. Whether you're an entrepreneur or just someone aiming for personal growth, you’ll learn how small, consistent changes lead to massive results.

Welcome back to TheUPside for 2026! If you have big goals for the new year but feel stuck, this episode is for you. True success is an inside job, and achieving something different requires becoming someone different.

In this episode, I share the five essential identities you must adopt to become a goal crusher in 2026. We'll explore how to build unshakeable confidence, embrace change as the price of growth, and keep the promises you make to yourself. This is your guide to moving past perfectionism and learning to see the upside in every situation. Discover the mindset shifts necessary for profound personal growth and leadership.

TheUPside is designed to help you get unstuck in your life and business by elevating your thinking from the inside out.

Subscribe and tune in every Tuesday for new episodes that will provoke meaningful change and help you achieve your maximum potential.

In this year end episode of TheUPside, Theresa and her husband Tommy Flood sit down to review the books that most shaped their thinking, leadership, business and faith this year. They talk about why leaders must be readers, how AI can be a true thought partner rather than just a shortcut, and why your digital reputation might be one of your most important assets heading into 2026.

Together they unpack big ideas from books like The AI Driven Leader by Jeff Woods, The Science of Scaling by Dr Benjamin Hardy and Blake Erickson, Wealthy and Well Known by Rory and AJ Vaden, Endless Customers by Marcus Sheridan, Build a Business You Love by Dave Ramsey, Beyond the Leader by Dr Tony Bridwell, The Benefit of Doubt by Craig Groeschel plus Theresa’s experience reading the Bible cover to cover this year.

You will hear practical takeaways on

• how to think more strategically with AI
• why impossible goals and short timelines can change who you become
• how to build a trustworthy personal brand that both people and AI can recommend
• what it really means to build a business you actually love
• how doubt can be an honest part of a growing faith

They wrap with encouragement to uplevel your reading by just one percent in 2026 and an invitation to share your own favorite reads for Theresa’s upcoming reading list.

Tune in and get inspired to build a book list and a life that keeps you living on TheUPside.

In this Thanksgiving week episode, Theresa invites you to pause and reflect on the power of gratitude. Whether this season feels full of blessings or heavy with struggle, she reminds us that gratitude is not about pretending everything is perfect. It is about recognizing the undeserved favor, the grace, and the goodness that still exist even in hard moments.

Theresa shares the surprising Latin root of the word gratitude and its deep connection to grace. She walks through four ways that practicing gratitude reshapes us from the inside out. Gratitude keeps us humble by reminding us that no one succeeds alone. It strengthens our relationships when we express appreciation to the people who matter most. It makes us more gracious and compassionate toward others. And it increases our happiness by shifting our focus from what is missing to what is present.

She also calls out the biggest enemies of gratitude including entitlement, self pity, and comparison and shows how choosing gratitude becomes the antidote that changes everything.

As you gather with family and friends this week, Theresa encourages you to slow down, reflect, pray, and speak your gratitude out loud. A grateful heart will always expand your joy.

Keep Living on TheUPside.

Clarity, Vision, and Momentum: Your End-of-Year Reset

Description:
The final months of the year aren’t just for finishing strong—they’re for creating clarity, vision, and momentum for what’s next. In this solo episode, Theresa Flood shares 10 powerful reflection questions to help you celebrate wins, learn from challenges, and reset your focus heading into 2026.

You’ll learn:

• Why sitting with questions can be more powerful than rushing to answers
  
  
  
• How to celebrate and double down on your biggest strengths
  
  
  
• What unfinished goals reveal—and which ones to release
  
  
  
• How to identify the habits, relationships, and bold moves that will shape your next year
  
  
  
• The one question that determines who you must become to reach your goals
  
  
  

Take time with these questions. Let them recharge your vision and prepare you to step into 2026 with clarity and momentum.

Smokey Garrett—founder of The GO Network and owner of the largest Keller Williams franchise brokerage in the U.S.—joins Theresa for a candid conversation on leading through disruption, building a culture that competes and cares, and why speed is a core leadership value. They cover Smokey’s unconventional path (yes, cutting horses 🐴), rookie year lessons, rebuilding a failing market center into #1, and how agents and leaders can adapt faster than the market. You’ll learn: Why orgs “start to look like their leader”—and how to make that a good thing The two real reasons people change (and how to lead both) How to translate vision into culture, momentum, and results What will actually matter for agents over the next 5–10 years (AI, service, communication)

What happens when your confidence takes a hit? Whether it’s a job loss, a hard year in business, or just that quiet self-doubt that creeps in when things get tough—confidence loss can leave you feeling unsure and stuck.

In this episode of TheUPside, Theresa shares 7 truths to help you rebuild your confidence from the inside out. You’ll learn how to:

• Keep the promises you make to yourself
  
  
  
• Stop comparing your insides to everyone else’s outsides
  
  
  
• Do hard things on purpose
  
  
  
• Step out with courage (even before you feel confident)
  
  
  
• Borrow someone else’s belief in you until yours returns
  
  
  

Confidence isn’t something you’re born with—it’s something you build. And if yours has been shaken lately, this episode will help you start rebuilding today.