Waking Up To Win25 Des 2025

E14: “Real Estate Business Planning That Actually Works”

In this episode of Waking Up to Win, Annie Callaway and Chad Elledge blend real estate motivation, mindset coaching, and practical business planning to help agents move from busy to intentional. From choosing joy during the holidays to building a business rooted in purpose, they unpack why identifying your “why” is the foundation of sustainable success in real estate.

Drawing inspiration from Simon Sinek’s framework, they walk through how understanding your personal and business why shapes client relationships, decision-making, resilience during tough deals, and long-term growth. The conversation expands into real estate business planning done differently, breaking the business into core pillars like marketing, operations, and sales, setting SMART goals, and aligning daily, weekly, and monthly actions with those goals instead of chasing commission checks.

Annie and Chad also tackle industry headlines, AI and Google entering MLS listings, commercial real estate predictions, and unfiltered takes on Rocket Mortgage, portal wars, and why local expertise still matters.

If you’re a real estate agent looking for clarity, motivation, mindset shifts, and a smarter way to plan your year without burnout, this episode will help you refocus, work on your business, and build something that lasts.

Listen now, subscribe, leave a review, share this episode with another agent who needs direction, and follow Waking Up to Win for weekly coaching, real talk, and strategies to help you keep winning.

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Episoder(31)

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 Mai 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 Mai 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 Mai 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 Apr 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 Apr 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 Mar 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 Mar 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 Mar 25min