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E7: "The Episode That Had Everything: Lien Waivers, Laughs, and Lessons"
In this hilarious and insight-packed episode of Waking Up to Win, hosts Annie Callaway and Chad Elledge, alongside producer Erin, dive into the real stories, real lessons, and real laughs behind life in real estate. From Annie’s unforgettable “fall heard around the parking lot” to Chad’s over-the-top sound system purchase, this episode reminds us that mindset and momentum matter more than perfection.
You’ll hear how the team turned a simple “One License, One Future” event into an inspiring opportunity for new agents to rethink their futures, and how they mix motivation with practical education to help people escape the corporate grind. Chad and Annie also break down key real estate insights: what to know about mechanic’s lien waivers, signing separately at closing, rising builder confidence, and the latest industry headlines. They also dug into Zillow pulling Matterport 3D tours to new AI tools for realtors, falling mortgage rates, and the Road to Housing Act shaking up affordable housing.
E6: "Hope Is Not A Method"
In this week’s episode of Waking Up to Win, hosts Annie Callaway and Chad Elledge tackle one of the hardest truths in real estate — hope is not a strategy. From pricing homes realistically to communicating with clients who don’t always want to hear the truth, this episode is a masterclass in what it means to lead with honesty, confidence, and kindness.
Annie shares how her affirmation of the week — “I have the courage to speak my truth and the heart to serve it with kindness” — applies to agents who struggle to have hard conversations with sellers, while Chad dives into how misplaced optimism and poor communication can cause listings to sit far longer than they should. Together, they explore how real estate professionals can stay grounded when the market feels shaky, offering unfiltered insight into what’s really happening behind the headlines.
E5: "Renters, Realtors, and Ridiculous Rules"
In this episode of Waking Up to Win, hosts Annie Callaway and Chad Elledge dive into what every real estate agent is talking about, the reality behind today’s housing market, the truth about buyer representation, and the future of the real estate industry as interest rates climb and inventory shifts. Annie and Chad bring their signature mix of humor, insight, and unfiltered coaching to hot topics like rising mortgage rates, AI-powered tools like Zillow’s new ChatGPT integration, and why so many buyers are still renting instead of building equity.
E4: “Market Shifts, Lawsuits & As-Is Chaos: Real Talk for Real Estate Agents”
Welcome back to Waking Up to Win with Annie and Chad, your go-to podcast for real estate motivation, high-performance mindset shifts, and practical coaching that moves you from stuck to top producer. This week’s episode is packed with powerful conversations around taking action now instead of waiting for “one day,” how to find clients anywhere, market headlines every agent needs to know, and some unfiltered real talk about the realities of contracts, inspections, and industry best practices.
From wedding season networking to unexpected client wins at the phone store, Annie and Chad remind us that today can be Day One. They break down the latest housing market trends — including interest rate updates from the Federal Reserve, rising mortgage rates, the impact of CoStar Group acquiring Matterport, leadership shakeups at realtor.com, and the lawsuit against Zillow by the Federal Trade Commission. Plus, they dive into how AI is shaping the future of real estate and what agents can do to stay ahead of the curve.
E3: "Real Estate Under Pressure: Compassion Acquisitions, Client Families, and Realtor Resilience"
On this episode of Waking Up to Win, Annie and Chad dive into the realities of being a real estate agent in today’s market, where patience and grace aren’t just affirmations, they’re survival skills. From handling first-time homebuyers with helicopter parents to navigating tricky negotiations, they share real stories that every Realtor canrelate to. They also unpack the breaking industry news about Compass acquiring Anywhere Real Estate for $1.6 billion, making it the largest brokerage in the world, and what that means for agents, clients, and the future of the realestate market.
With unfiltered honesty, they explore how to maintain professionalism when family dynamics complicate transactions, the importance of remembering who yourclient really is, and how big brokerage moves could reshape the way agents do business. Along the way, they sprinkle in humor, candid moments, and even a wild real estate headline that has to be heard to be believed (yes, 159,000 text messages).
E2: "Soda Wars, Zillow Lawsuits & Solving Client Problems"
Welcome back to Waking Up to Win with Annie and Chad, the unapologetically real podcast where real estate, mindset, and motivation collide. This week’s episode is packed with laughter, raw truths, and real-world coaching for agents who want to stop running ragged and start building a business that actually wins.
From hilarious soda-stealing stories to the serious realities of rising mortgage rates, housing affordability challenges, and messy brokerage promises, Annie and Chad pull back the curtain on what’s really happening in real estate right now. You’ll hear why selling homes isn’t about selling at all, it’s about solving problems, and how to stay focused when the headlines scream chaos. We even dive into Zillow vs. Compass lawsuits, home seller concessions, shady listing agent practices, and whether brokers should really be promising leads in the first place.
The big takeaway? Real estate isn’t about waiting on perfect market conditions, magical leads, or the right brokerage pitch. It’s about taking ownership of your business, staying solutions-focused, and refusing to let the noise distract you from your goals.
E1: "Lawsuits, Listings That Won’t Sell, and Owning Your Success in Real Estate"
Welcome to the very first episode of Waking Up to Win with Annie and Chad, your go-to podcast for real estate motivation, mindset shifts, and the kind of coaching that helps agents stop running ragged and start building intentional success.
In this debut episode, we dive into the current Compass vs. Zillow lawsuit, what MLS changes mean for real estate agents, and why transparency in listings truly matters for clients. We also share real stories from the field, including the challenges of selling a house that smells like cigarette smoke, what agents can really do to help their sellers, and how buyers actually react when strong odors or poor curb appeal get in the way.
Along the way, Annie and Chad unpack the truth about creating success one intentional move at a time, why excuses don’t sell houses, and how to keep your focus on clients instead of industry noise. From navigating smoke remediation costs to understanding seller options in today’s changing market, this episode is full of practical lessons and unfiltered real estate talk that every agent needs to hear.