Waking Up To Win

Waking Up To Win

Waking Up to Win is the no-fluff, all-fire podcast for real estate agents who are ready to stop playing small and start building a business that actually works. Hosted by Annie Callaway and Chad Elledge, top-producing agents, brokerage owners, and your new favorite truth-telling duo, this show dishes out bold strategy, unapologetic motivation, and the realest real estate conversations you won’t hear anywhere else. From tactical advice that gets results to mindset shifts that move mountains, Waking Up to Win is where chaos meets clarity, humor meets hustle, and nothing is off-limits.

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Jaksot(31)

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

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”

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”

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”

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)"

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”

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”

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”

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

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