Waking Up To Win30 Loka 2025

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.

With equal parts comedy, coaching, and chaos, Annie and Chad prove that success in real estate takes more than contracts. It takes confidence, adaptability, and a sense of humor. You’ll walk away with motivation to “challenge your limits, not limit your challenges,” and maybe a new appreciation for staying upright during showings.

Tune in, subscribe, and share this episode with your favorite agent who needs a reminder that even the best fall down sometimes—but winners always get back up.

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E31: “The Grossest Real Estate Story We’ve Ever Told”

In this episode of Waking Up to Win, Annie and Chad dive into the chaos, comedy, and real conversations happening inside today’s real estate industry. From the difference between being “busy” versus a...

21 Touko 31min

E30: “Check Your Circle Before You Wreck Your Business”

On this episode of Waking Up to Win, Annie and Chad dive into the mindset shifts every real estate agent needs to survive — and thrive — in today’s market. From failed contracts and emotional rollerco...

17 Touko 39min

E29: “Five Lots, Zero Dollars, One Very Confused Realtor”

In this episode of Waking Up to Win, Annie and Chad dive into the realities of real estate contracts, FHA loans, appraisal issues, lender mistakes, buyer contingencies, and the emotional rollercoaster...

7 Touko 55min

E28: “Don’t Take the Bait: Real Estate Mindset That Wins Deals”

In this episode of Waking Up to Win, Annie and Chad dive into real estate mindset, emotional intelligence, and the internal work required to become a top-producing agent. From navigating difficult neg...

9 Huhti 43min

E27: "Why the Average Homebuyer Is Now 40 (And What It Means)"

In this episode of Waking Up to Win, Annie and Chad dive into real estate mindset, productivity, and what it actually takes to go from feeling stuck to becoming a top-producing agent. From the power o...

2 Huhti 48min

E26: “Candid Convos: Sherry Ruyle”

In this episode of Waking Up to Win, Chad Elledge sits down with Sherry Ruyle of Meyer & Company Real Estate and Auctions for a powerful and honest conversation about what it really takes to build a s...

23 Maalis 52min

E25: “Real Estate Conversations That Will Change How You Sell Homes”

In this episode of Waking Up to Win, Annie and Chad dive into real estate mindset, industry insights, and the kind of behind-the-scenes conversations every agent needs to hear. From a powerful quote b...

19 Maalis 52min

E24: “Candid Convos: Drew Quinones”

In this episode of Waking Up to Win, Chad Elledge sits down with St. Louis loan officer Drew Quinones for an honest, unscripted conversation about what really drives success in the real estate and mor...

16 Maalis 25min