TheUPside Podcast

Linda McKissack has been in real estate for forty years, but her story does not start with success. It starts with a $600,000 loss, a failing business and a marriage under more pressure than either she or her husband Jimmy had ever faced. In this episode, Theresa sits down with Linda, a former mega agent, two region owner within Keller Williams, market center owner and bestselling author, to talk...

We are halfway through 2026, which means it is time to stop and do an honest assessment of where you actually are versus where you said you wanted to be. In this episode, Theresa walks you through what she calls the Halftime Huddle, a practical and honest reflection process for the midpoint of the year. Whether you are crushing it and want to build more momentum, or you are behind and wondering if...

Somewhere along the way, morning routines became a competition. Who gets up earliest, who journals longest, who has the most intense morning ritual. And in all of that, a lot of us either burned out trying to keep up or tuned out because it felt like something that was not for us. In this episode, Theresa reframes the whole conversation. A morning routine is not about how much you can fit in befor...

Have you ever felt like you are just drifting through life, even when things look good on the outside? That was exactly where today's guest, Dana Gentry, found herself before everything changed. Dana is a former mega agent, Keller Williams operating partner, senior culture advisor for Keller Williams, and now a bestselling author. She sat down with Theresa to talk about what it actually means...

This one is a little different, and it might just be one of the best episodes yet. Theresa has been trying to get today's guest on the podcast for over a year, and she finally said yes. That guest is Juliette Joy Flood, better known as Jett, Theresa's daughter, who just graduated eighth grade. In this conversation, Jett shares what she actually learned over three years of middle school....

Have you ever said "I didn't have a choice" and genuinely believed it? Most of us have. But in this episode, Theresa breaks down why that phrase, and others like it, might be one of the most costly things you say on a regular basis. Victim language is not about whether something hard happened to you. It is about the subtle ways your words remove you from the equation and hand your p...

What if the cage keeping you stuck as a leader isn't your circumstances, your team, or your market — but your own autopilot thinking? In this episode, Theresa sits down with Lucas Sherradan, longtime Keller Williams leader, host of the Built Out Podcast, keynote speaker, and author of the forthcoming book The Uncaged Leader: Surprisingly Simple Shifts in Curiosity and Awareness That Empower L...

Freedom is one of the most powerful core values a person can have, and for most entrepreneurs it is the whole reason they got into business in the first place. But here is the tension nobody talks about: real freedom requires accountability. In this episode, Theresa breaks down the direct relationship between the two and why you cannot have one without the other. Using the Parable of the Talents a...

Have you been waiting to feel confident before you start? Here is the truth nobody wants to hear: confidence is not the starting point. It is the end result. And if you keep waiting for it to show up before you take action, you will be waiting a very long time. In this episode, Theresa breaks down a simple but powerful formula that will shift how you think about confidence entirely. It starts with...

It's Mother's Day week, and Theresa is joined by two of her favorite moms for a conversation that is as honest as it is encouraging. Michelle Ozymi is officially launched into the empty nest season with three grown kids living their best lives in New York, Seattle, and Indiana. Macy has two kids in elementary school and is deep in the thick of it. And Theresa is somewhere in the middle,...

What happens when a father stands in a hospital room watching his five-year-old son fight for his life and makes a vow to God right then and there? For Coach Lawrence Mann, that moment did not just change his family. It launched a 30-year movement. In this episode, Theresa sits down with the founder of Top Achievers Foundation, a nonprofit serving kids in the Dallas area since 1996. Coach Mann sha...

Have you ever felt stuck between the weight of your past and the uncertainty of your future? In this episode of TheUPside, Theresa unpacks one of the most thought-provoking concepts she has encountered in her personal growth journey: the difference between linear time and holistic time. Most of us move through life thinking time works like a row of dominoes. Yesterday leads to today, today leads t...

What does it take to lead for 35 years and still love what you do? Theresa sits down with Wendy Harrelson, Divisional Leader for the Central Division and one of Keller Williams' most decorated leaders, for a conversation that is as honest as it is inspiring. Wendy's journey didn't start with a master plan. It started with a real estate book at an Eckerd's drugstore and a phone...

If you want better relationships stronger leadership and more meaningful results in your life and business it all starts with one overlooked skill listening. In this episode of TheUPside Podcast, Theresa Flood breaks down 7 practical frameworks to help you become a more intentional and impactful listener. Because the truth is most people are not listening to understand. They are listening to respo...

Why do we feel stuck… even when we are doing all the right things? In this episode of The UPside, Theresa breaks down the 3 most common reasons people feel stuck and how to move forward with clarity and confidence. Not all stuck is created equal. And if you do not understand what kind of stuck you are in, you will keep spinning your wheels. Theresa walks through: • Complacent stuck and why comfort...

What does it really take to build a healthy, high performing company? In this episode of TheUPside Podcast, Theresa Flood sits down with John Luke Spitler, Founder and CEO of The Encompass Group and author of The Art of Talent, to talk about leadership, purpose, people optimization, and what separates great leaders from the rest. John Luke shares how leaders can create clarity, build trust, develo...

What does it really mean to feel confident in your own skin? In this episode of TheUPside , Theresa sits down with dermatologist Dr. Mara Dacso for a conversation that goes far beyond beauty trends and skincare products. Together, they explore the powerful connection between skin health, self confidence, stress, wellness, and the way we show up in the world. Dr. Dacso is a recognized leader in der...

Tommy Flood is back on TheUPside and this episode is for leaders! In Part 2 of our Family Reunion 2026 AHA series, we break down three leadership themes we cannot stop thinking about and what we are doing with them now. We build people and people build businesses  Unreasonable hospitality is not just for restaurants. It is a leadership standard. We talk about culture, emotional impact, and why dai...

You are a media brand. Whether you like it or not. That was one of our biggest takeaways from Keller Williams Family Reunion 2026. In this episode, Seth Mills joins me to unpack our top AHAs from Social Con and insights from Gary Vee, Giselle Ugarte, Neil Patel, Donald Miller, and Jay Shetty. Three defining shifts: • You are a media brand and your presence matters.  • AI will replace you if you us...

Are you feeling stressed, anxious, or overwhelmed? In this episode of The Upside Podcast , we dive into the root causes of stress and how to overcome them by focusing on what’s within your control. Drawing inspiration from Stephen Covey’s The 7 Habits of Highly Effective People , we explore the "Circle of Concern," "Circle of Influence," and introduce the "Circle of Direct...

Do you feel like you're constantly running behind, stuck in a cycle that never seems to end? It's time to stop trying to manage time and start managing your relationship with it. This episode of TheUPside Podcast challenges the conventional wisdom around productivity and offers a fresh perspective on getting things done. We expose the common time management myths that contribute to a sta...

Are you ready to take your business and life to the next level? In this follow-up episode of TheUPside , host Theresa Flood is back with Seychelle Van Poole to dive into the tactical strategies for creating both a thriving business and a fulfilling life. If you missed last week’s episode with Seychelle,, be sure to listen to that first for the foundational insights. In this episode, Seychelle shar...

Is it actually possible to build a big business and a big life at the same time, or do you eventually have to choose one? In this episode of The UPside Podcast, Theresa Flood sits down with Seychelle Van Poole for a raw and honest conversation about success, burnout, reinvention, and redefining what it really means to win. Seychelle is the owner of Van Poole Properties Group with Keller Williams,...

Ready to take control of your growth in 2026? In this episode of TheUPside Podcast, host Theresa Flood reveals why mastering change is the key to accomplishing your goals—both in life and business. Discover why we often resist change and how to overcome the obstacles that hold us back. Theresa dives into the common “learner’s trap” of gathering knowledge without putting it into action and shows yo...

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...