Stop Drifting. Start Living on Purpose. Dana Gentry on TheUPside

Stop Drifting. Start Living on Purpose. Dana Gentry on TheUPside

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 to live an intentional life and why most of us are closer to a breakthrough than we think. In this conversation, Dana shares how she went from feeling semi-successful and unfulfilled to building a life with real direction and momentum. She talks about the number one thing she had to get a grip on first, why saying yes to everything nearly cost her everything, and the momentum equation she has lived by for years. You will also hear the story behind the five yard line versus the fifty yard line and why that one idea might be exactly what you need to keep going right now. This one is for anyone who is in the gradually and wondering if the suddenly is ever going to show up.

Lessons from Middle School: An Interview with Jett Flood

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. They talk about friendship seasons and finding your real people, what confidence actually looks like from the inside, how Jett handled drama and hard moments without losing herself, and what growing up with a lot of injuries taught her about mental toughness. Jett also tells the story of a science project that nearly broke her, a decision to not cut corners when she easily could have, and what it felt like on the other side of doing the hard thing the right way. There is wisdom in this conversation that a lot of adults are still working on. If you are raising a teenager, navigating your own hard season, or just need a reminder of what it looks like to grow from the inside out, this episode is for you.

Victim Language: The Sneaky Words That Keep You Stuck

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 power over to someone or something else. And the tricky part? It does not always sound like complaining. Sometimes it sounds like honesty. Sometimes it even sounds like humility. Theresa walks through the most common forms of victim language, from "they made me" to "that's just how I am," and explains why even high-achieving, accountable people fall into these patterns without realizing it. She also shares a personal story about returning to work after having her daughters and how one language shift changed everything about how she felt about that decision. This episode is a reset. It is practical, honest, and exactly the kind of inside-out thinking that TheUPside is built on. Catch yourself this week, and start writing your own story again. Subscribe at theresaflood.com to receive the free weekly teaching guide.

The Uncaged Leader: An Interview with Lucas Sherradan

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 Leadership. Lucas unpacks the difference between leaders who are led by vision and leaders who are led by preference, programming, and fear. He walks through why 95% of people believe they are self-aware while only 10% actually are, and what that gap is costing in real estate businesses, marriages, and leadership pipelines every day. He introduces his Five O'Clock Formula — a single curiosity question that interrupts judgment before it hardens into story — and explains why authority does not need volume to lead. Lucas also opens up about the personal story that shaped the book: his mother, a Korean immigrant who fought ovarian cancer with extraordinary courage, and the deathbed promise that became the heart of his mission. 100% of the profits from The Uncaged Leader go to fighting human trafficking. You can join the wait list and pre-order at theuncagedleader.com. If you have been leading from autopilot, getting results that look good on paper but feel hollow, or wondering why the same patterns keep showing up in your team and your life, this conversation is the reset. Subscribe at theresaflood.com for weekly training guides and tools.

The Accountability Equation: How to Get More Freedom in Your Life

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 as a framework, Theresa walks through what it actually means to give account for what has been entrusted to you, whether that is your time, your money, your relationships, your leadership, or your God-given gifts. She unpacks why playing it safe out of fear is just as costly as making a bad decision, and why blaming others always comes at the expense of your own authority. If you have been coasting, playing small, or waiting for someone else to hand you a roadmap, this episode is a direct and honest reset. Theresa gives you three practical steps for becoming a truly accountable person and explains why that is the only path to the freedom you are actually after. Subscribe at theresaflood.com for weekly training guides and tools.