Waking Up To Win

Annie Callaway and Chad Elledge
  • 5.0 (1)
  • Entrepreneurship
  • Updated Weekly

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.

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

    May 21

    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.

    31 min
  2. E30: “Check Your Circle Before You Wreck Your Business”

    May 17

    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.

    39 min
  3. E29: “Five Lots, Zero Dollars, One Very Confused Realtor”

    May 7

    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.

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

    Apr 9

    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

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

    Apr 2

    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.

    49 min
  6. E26: “Candid Convos: Sherry Ruyle”

    Mar 23

    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 sustainable and fulfilling career in real estate. With over two decades of experience in the industry, Sherry shares her unique journey from corporate America to real estate leadership, including her early years supporting agents behind the scenes, her transition into sales, and ultimately building a successful team focused on coaching and growth.  Throughout the conversation, Sherry breaks down the importance of systems, strategic planning, and working on your business—not just in it, especially during shifting real estate markets. She shares how agents can weather market changes by focusing on consistency, evaluating what’s working, and collaborating with others instead of operating in isolation. The discussion dives into real estate agent mindset, business growth strategies, leadership development, coaching, and the power of relationships, emphasizing that long-term success in real estate comes from being intentional, relational, and committed to continuous personal growth. Sherry also highlights simple but impactful habits—like sending handwritten notes—that help agents stand out in a digital-first world and build deeper client connections.  If you are a real estate agent feeling stuck, overwhelmed, or unsure how to grow your business in today’s market, this episode will give you both practical strategy and the mindset shift needed to move forward. Follow Waking Up to Win for more real estate coaching, leadership insights, and business growth strategies, and share this episode with another agent who is ready to stop surviving and start building a business that actually works. Connect with Sherry Ruyle: 731-225-4918 https://www.facebook.com/sherry.ruyle https://www.instagram.com/sherryruylerealestate/

    52 min
  7. E25: “Real Estate Conversations That Will Change How You Sell Homes”

    Mar 19

    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 by Eleanor Roosevelt on dreaming big to a deep discussion on insurance, homeownership, and real estate policy, this episode blends motivation with real-world strategy for Realtors and entrepreneurs alike. You’ll hear eye-opening insights from a recent insurance lunch-and-learn, including how your insurance score impacts your rates, why filing small claims can cost you long-term, and how claims follow both you and the property. Annie and Chad also break down a proposed housing bill that could force institutional investors to sell rental homes, sparking a real debate on government regulation, housing supply, and the future of homeownership. Plus, in this week’s “What the Floop” segment, they unpack a surprising stat about for-sale-by-owner listings and what it really means for Realtors looking to grow their business. This episode is packed with actionable takeaways on mindset, client conversations, and navigating today’s evolving real estate market. If you’re a real estate agent, entrepreneur, or anyone looking to level up your business, this conversation will challenge your thinking and give you tools to move from stuck to top producer. Subscribe, leave a review, and share this episode with your real estate bestie. And if you’ve got a wild real estate story, send it in—you might hear it on a future episode.

    53 min
  8. E24: “Candid Convos: Drew Quinones”

    Mar 16

    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 mortgage industry. Drew shares the leadership mindset that has helped him quickly rise as a top-producing loan officer, including the belief that great leaders are simply ordinary people with extraordinary determination. Throughout the episode, Chad and Drew discuss the importance of reputation, character, and what people say about you when you’re not in the room, along with how those values shape long-term success in business. The conversation dives deep into the relationship between real estate agents and loan officers, explaining why the best real estate transactions happen when lenders are treated as true partners instead of vendors. Drew explains how communication, trust, and shared expectations between agents and lenders can dramatically improve the home buying experience for clients. They also explore the psychology of sales in real estate, including how asking better questions can lead to more honest conversations with buyers and help agents better understand a client’s real timeline for purchasing a home. Chad and Drew also break down recent mortgage headlines about interest rates dropping below 6%, explaining why those headlines can be misleading for many buyers and how credit score, loan amount, and down payment actually influence mortgage rates. The discussion provides real insight for real estate agents, loan officers, and home buyers who want to better understand how lending works behind the scenes and how strong partnerships inside a transaction can create better outcomes for everyone involved. If you’re a real estate professional looking to improve your mindset, strengthen your lender relationships, and better understand how mortgage lending impacts your deals, this conversation offers practical insights and real-world experience from professionals working in the industry every day. Be sure to subscribe to Waking Up to Win, follow the podcast for more conversations about real estate success, and share this episode with a real estate agent or loan officer who wants to grow their business and win in today’s market. Find Drew Quinones on Instagram at @drewqhomeloans.

    26 min
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About

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.

Information

  • Creator
    Annie Callaway and Chad Elledge
  • Years Active
    2025 - 2026
  • Episodes
    31
  • Rating
    Explicit
  • Copyright
    © Annie Callaway and Chad Elledge
  • Show Website
    Waking Up To Win