2D AGO

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

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

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

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

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

MAR 12

E23: "Fire Horse Energy and Winning in Real Estate"

In this episode of Waking Up to Win, Annie Callaway and Chad Elledge return to the studio with a conversation that blends real estate strategy, market insight, business mindset, and a little unexpected inspiration from the Chinese zodiac Year of the Fire Horse. Annie explains how a late-night research rabbit hole about the Chinese lunar calendar led to a surprising realization about business cycles and the real estate market. The pair discuss how recent years in the housing industry mirror the phases of vision, strategy, and execution described in the zodiac cycle, suggesting that 2026 may be a “sprint year” for real estate professionals ready to move fast, take action, and capitalize on opportunities in the market. The conversation then shifts into practical advice for real estate agents, including a surprising MLS rule many agents still misunderstand about listing photos and the importance of choosing the right “hero image” for real estate marketing on Zillow, Realtor.com, Redfin, and MLS platforms. Chad and Annie also break down current real estate headlines, including rising mortgage delinquencies, housing affordability challenges caused by property taxes and insurance increases, and the impact of AI tools and coaching apps in the real estate industry. They explore how artificial intelligence can make real estate agents more efficient without replacing the human relationship skills that define great service professionals. The episode also touches on legal developments affecting the housing industry, including lawsuits involving mortgage companies and the broader conversation around steering, RESPA regulations, and fair housing compliance. By the end of the conversation, listeners gain insight into real estate market cycles, business mindset for agents, modern real estate marketing strategies, and how to think strategically about growth during uncertain market conditions. If you are a real estate agent, team leader, broker, or entrepreneur navigating today’s housing market, this episode offers practical perspective, industry commentary, and motivation to move forward with confidence. Be sure to subscribe to Waking Up to Win, leave a review, and share the episode with another real estate professional who wants to grow their business, stay ahead of industry trends, and win in today’s market.

46 min

MAR 5

E22: "Producer To Co-Host: Erin Prosperi Steps In"

In this episode of Waking Up to Win, host Chad Elledge flips the script and brings someone from behind the camera to the mic. Joining him is Erin Prosperi, the producer of Waking Up to Win -The Podcast and the Executive Coordinator for Realty ONE Group Trifecta. Erin usually keeps everything running smoothly behind the scenes, but in this episode she steps into the spotlight to share what it takes to support a high-performing real estate brokerage and the people inside it. Chad and Erin talk about the often unseen work that keeps a real estate team operating at a high level, from coordinating operations and managing details to maintaining the culture and energy inside a growing brokerage. Erin shares her perspective on supporting leadership, helping agents succeed, and why strong operational support can make a massive difference in the productivity and experience of real estate professionals. The conversation highlights how behind-the-scenes leadership, organization, and teamwork help create an environment where real estate agents can focus on building their business and serving their clients. Listeners will gain insight into brokerage culture, real estate team dynamics, and the importance of having the right people supporting the mission of a growing real estate company. If you're a real estate agent, team leader, or brokerage owner looking to grow your business, build a stronger culture, and understand the operations that help agents succeed, this episode offers valuable perspective from someone who helps make it all happen behind the scenes. Be sure to subscribe to Waking Up to Win for more conversations about real estate success, leadership, agent growth, mindset, and building a thriving real estate career, and share this episode with another agent who wants to level up their business.

42 min

FEB 12

E21: "Market Reality, Myths, and Momentum"

In this episode of Waking Up to Win, Annie Callaway and Chad Elledge dive into real estate headlines, agent confidence, and the behind-the-scenes realities shaping today’s housing market, while delivering the kind of candid coaching and opinions agents don’t always hear out loud. From rising agent optimism and what a “healthier” market actually means, to price reductions, negotiation norms, and why nearly two-thirds of buyers are paying under list price, Annie and Chad break down what these trends mean for realtors working with buyers, sellers, and investors right now. The conversation takes a sharp turn into real estate investing myths, including the outdated one-percent rule, cap rates, corporate buyers, and why mom-and-pop investors are struggling to compete in a market dominated by long-term institutional strategies. They also unpack a powerful business lesson around ownership, control, and value, challenging agents to think of their contacts, CRM, and sphere of influence as the true “gold” of their business, and to ask who really owns that asset. If you’re a real estate agent looking for market clarity, smarter conversations with clients, stronger business fundamentals, and honest perspective on industry noise, this episode will help you think more strategically and act with intention. Listen in, share this episode with an agent who needs the reality check, subscribe to Waking Up to Win, and keep building a business you actually own.

44 min

Waking Up To Win

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

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

E26: “Candid Convos: Sherry Ruyle”

E25: “Real Estate Conversations That Will Change How You Sell Homes”

E24: “Candid Convos: Drew Quinones”

E23: "Fire Horse Energy and Winning in Real Estate"

E22: "Producer To Co-Host: Erin Prosperi Steps In"

E21: "Market Reality, Myths, and Momentum"

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Waking Up To Win

Episodes

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

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

E26: “Candid Convos: Sherry Ruyle”

E25: “Real Estate Conversations That Will Change How You Sell Homes”

E24: “Candid Convos: Drew Quinones”

E23: "Fire Horse Energy and Winning in Real Estate"

E22: "Producer To Co-Host: Erin Prosperi Steps In"

E21: "Market Reality, Myths, and Momentum"

About

Information