Cover image of show Waking Up To Win

Waking Up To Win

Podcast by Annie Callaway and Chad Elledge

English

Business

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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.

All episodes

31 episodes

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

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.

21 May 2026 - 31 min
episode E30: “Check Your Circle Before You Wreck Your Business” artwork

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.

17 May 2026 - 39 min
episode E29: “Five Lots, Zero Dollars, One Very Confused Realtor” artwork

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.

7 May 2026 - 55 min
episode E28: “Don’t Take the Bait: Real Estate Mindset That Wins Deals” artwork

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 negotiations and handling high-pressure client interactions to mastering personal triggers and building a strong morning routine, this episode blends real estate coaching with powerful personal development insights. They explore the importance of self-awareness, agency, and controlling your internal “vibe” to succeed in business and life. A standout moment in this episode is Chad sharing his go-to morning routine centered around the Affirmation Club playlist on Spotify—a collection of affirmation-based music designed to help you align your mindset, build confidence, and start your day with intention. This powerful tool reinforces the idea that what you consume mentally and emotionally shapes how you show up in your business and your life. The conversation also touches on real estate market trends, housing affordability, HOA fees, and how external factors impact today’s buyers and agents. Annie and Chad break down how emotional reactions can derail deals, why learning to pause and respond logically is a critical skill in real estate, and how identifying your core values can transform both your business and personal life. Whether you’re a new real estate agent, seasoned professional, or entrepreneur looking to level up your mindset, this episode provides actionable strategies to help you stay grounded, think logically under pressure, and grow your business with intention. If you’re ready to elevate your mindset, improve your communication skills, and build a thriving real estate business, subscribe to Waking Up to Win, leave a review, and share this episode with another agent who’s ready to grow. And don’t forget to check out the Affirmation Club playlist linked below to start building your own powerful morning routine. https://open.spotify.com/playlist/37i9dQZF1E4zbd9NrpEFAQ

9 Apr 2026 - 43 min
episode E27: "Why the Average Homebuyer Is Now 40 (And What It Means)" artwork

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 of taking intentional “sabbaticals” to clear mental clutter, to overcoming objections as a newer real estate agent, this conversation is packed with actionable coaching and real-world insights. They also break down major housing market trends, including why the average first-time homebuyer is now 40, how affordability is reshaping the market, and why parents are increasingly helping their kids buy homes. Plus, they unpack a viral story about a homeowner using AI tools like ChatGPT to sell a property, and whether it cost him thousands in missed profit. If you're a real estate agent, investor, or entrepreneur looking for motivation, business growth strategies, and a winning mindset, this episode gives you the tools to level up your career and life. Tune in to learn how to work on your business, build confidence with clients, and stay ahead in today’s competitive real estate market. If you found value in this episode, subscribe, share it with another agent, and start applying these strategies today to create your next breakthrough.

2 Apr 2026 - 48 min
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En fantastisk app med et enormt stort udvalg af spændende podcasts. Podimo formår virkelig at lave godt indhold, der takler de lidt mere svære emner. At der så også er lydbøger oveni til en billig pris, gør at det er blevet min favorit app.
Rigtig god tjeneste med gode eksklusive podcasts og derudover et kæmpe udvalg af podcasts og lydbøger. Kan varmt anbefales, om ikke andet så udelukkende pga Dårligdommerne, Klovn podcast, Hakkedrengene og Han duo 😁 👍
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