Waking Up To Win

About 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.

Publisher

Annie Callaway and Chad Elledge

Category

business

Language

en

Explicit

No

First episode

18 Sept 2025

Latest episode

21 May 2026

Latest episodes

31 episodes in the feed.

1. 

   21 May 2026

   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 actually productive, to the mindset traps that keep real estate agents stuck in survival mode, this episode blends motivation, leadership, and hilarious storytelling in a way only they can. They unpack how successful Realtors can stop operating like ants on autopilot and start thinking like true business owners. The conversation takes a wild turn into real estate disclosure stories, property cleanup nightmares, and lessons learned from unexpected situations that every Realtor should understand. Annie and Chad also break down major industry headlines, including changes to Fannie Mae and Freddie Mac credit scoring models, how rent and utility payments may help first-time home buyers qualify for mortgages, and what the latest brokerage mergers mean for the future of real estate. From real estate coaching and agent mindset to brokerage culture, leadership, entrepreneurship, and market shifts, this episode is packed with practical insight, motivation, and unforgettable moments. If you’re a real estate agent, broker, entrepreneur, or business owner looking for real talk about growth, mindset, leadership, and the future of the housing market, this episode is for you. Be sure to subscribe, leave a review, and share this episode with another Realtor who needs a laugh and a reset this week.

2. 

   17 May 2026

   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 rollercoasters to client boundaries, leadership, motivation, and the people you surround yourself with, this conversation is packed with relatable Realtor experiences and practical coaching for agents who want to grow their business without losing themselves in the process. They also tackle real estate market trends, historic home debates in Missouri, downtown development conversations, office-to-residential conversions, and the importance of making decisions based on your client’s best interests instead of emotion. If you’re a Realtor, entrepreneur, sales professional, or business owner looking for real estate motivation, real estate coaching, mindset strategies, and honest conversations about the highs and lows of the industry, this episode is for you. Subscribe, leave a review, and share this episode with your real estate bestie — and remember, don’t just survive this week… get out there and build your business.

3. 

   7 May 2026

   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 that agents face during difficult transactions. From unpacking “mental rocks” and boosting productivity to breaking down one chaotic FHA appraisal disaster step-by-step, this episode delivers real estate coaching, mindset advice, and practical industry insight for Realtors, brokers, team leaders, and real estate professionals navigating today’s market. They also unpack major real estate industry headlines, including NAR settlement updates, crypto-backed mortgages, FHA financing rules, earnest money disputes, appraisal contingencies, and how agents can better protect buyers and sellers during complex deals. If you’re a Realtor looking for real estate training, contract education, negotiation strategies, mortgage insights, or motivation to grow your business while staying sane, this episode is packed with real-world lessons and behind-the-scenes stories you won’t want to miss. Subscribe to Waking Up to Win for weekly real estate motivation, real estate coaching, market updates, Realtor education, and honest conversations designed to help agents stop surviving and start winning in business and life.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

1 ratings

Contact Waking Up To Win

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.