Waking Up To Win
Annie Callaway and Chad Elledge
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.
Episodes
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.
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.
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.
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
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.
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:731-225-4918https://www.facebook.com/sherry.ruylehttps://www.instagram.com/sherryruylerealestate/
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.
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.
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.
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.
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.
E20: "Realtors, Do Better: Marketing, Lawsuits, and Industry Reality"
In this episode of Waking Up to Win, Annie Callaway and Chad Elledge bring their signature mix of real estate coaching, market commentary, and unfiltered opinions to the headlines agents are actually dealing with right now. From snowmageddon showings and why first impressions still make or break a sale, to agents needing to “do better” when it comes to vacant listings, marketing follow-through, and client experience, this conversation is equal parts practical and opinionated. Annie and Chad dig into major industry news, including RESPA lawsuits involving Rocket Mortgage and Zillow, referral fee confusion, informed consent, and what agents legally, and ethically, need to understand about settlement providers. They also debate AI integration in real estate, MLS leadership hiring chief AI officers, and where technology should support agents without replacing human judgment. If you’re a real estate agent who wants clarity on current headlines, better business habits, and straight-talk coaching that challenges you to raise your standards, this episode will sharpen your perspective and your practices. Listen in, share this episode with an agent who needs the reminder, subscribe to Waking Up to Win, and keep building your business with intention, professionalism, and confidence.
E19: "Real Estate News, Strong Opinions, and No Sugarcoating"
In this episode of Waking Up to Win, Annie Callaway and Chad Elledge blend real estate coaching, mindset, and unfiltered industry conversation to help agents focus on what actually moves the needle. From task prioritization, efficiency versus effectiveness, and identifying true “must-dos,” to real-world coaching around SOI marketing, paid lead generation, ROI, and budgeting time versus money, this episode delivers practical clarity for agents who feel busy but not productive. Annie and Chad break down how to choose lead sources wisely, why working your sphere of influence builds the most sustainable business, and how buying leads is really just paying to expand your network when done correctly. The conversation also covers major real estate headlines, including housing reform discussions, corporate home buying, mortgage-backed securities, affordability challenges, new construction shortages, and why first-time homebuyers are being priced out. Along the way, they keep things real with relatable stories, market debates, and a classic “what the floop” moment that every agent who’s shown homes can laugh at. If you’re a real estate agent looking for motivation, market perspective, smarter lead strategy, and coaching that helps you work on your business instead of spinning your wheels, this episode will give you both insight and encouragement. Listen in, share this episode with a fellow agent who needs direction, subscribe to Waking Up to Win, and keep building your business with intention, clarity, and confidence.
E18: “First-Time Buyers, Lifestyle Renters, and Market Reality”
In this episode of Waking Up to Win, Annie Callaway and Chad Elledge kick off the new year with real estate insight, mindset coaching, and unfiltered industry commentary agents actually need to hear. From practical education around PMI removal, loan-to-value rules, and mortgage myths, to big-picture conversations about first-time homebuyers, generational wealth transfer, lifestyle renters, and affordability challenges, this episode blends tactical knowledge with honest perspective. Annie and Chad also break down major real estate headlines, including commission lawsuit updates, Zillow and brokerage liability, buyer agent compensation, and what today’s market means for agents trying to build sustainable businesses. Along the way, they tackle common agent struggles like waiting for the phone to ring, misunderstanding commissions as paychecks, side hustles versus prospecting, and why working on your business matters more than ever. If you’re a real estate agent looking for market clarity, motivation, prospecting ideas, and straight-talk coaching that cuts through the noise, this episode will leave you better informed and ready to take action. Listen in, share this episode with a fellow agent who needs a reality check, subscribe to Waking Up to Win, and keep showing up ready to build momentum, confidence, and a business that actually works.
E17: "Candid Convos: Tammy Mueller"
In this special bonus feature episode of Waking Up to Win, Annie Callaway and Chad Elledge sit down with real estate powerhouse Tammy Mueller for a candid conversation about mentorship, real estate coaching, and what it really takes to succeed as a new agent. As the leader of the Realty ONE Group mentor program, Tammy shares why mentoring agents is a calling, how mentorship fills the gaps traditional real estate classes leave behind, and what new agents actually struggle with once they’re licensed. From working on your business versus working in it, to business planning, accountability, time management, and setting realistic expectations about freedom, income, and growth, this episode offers real-world insight every agent needs to hear. Tammy breaks down what makes a great mentee, how confidence is built through education and action, and why relationships, consistency, and intentional planning are the foundation of a sustainable real estate career. If you’re a new agent looking for training and support, an experienced agent considering mentorship, or someone curious about starting a career in real estate, this bonus episode delivers clarity, encouragement, and practical direction. Listen in, share this episode with an agent who needs guidance, subscribe to Waking Up to Win, and reach out to learn more about the mentorship opportunities available through Realty ONE Group.
E16: “What’s Meant for You Won’t Miss You: Real Estate Mindset for 2026”
In this episode of Waking Up to Win, Annie Callaway and Chad Elledge kick off the new year with a mix of real estate motivation, market insight, and the kind of unfiltered conversation agents secretly love. From the reminder that what’s meant for you will never miss you to real client stories where “failed” deals turned into dream homes, they break down why settling in real estate—whether it’s a house, a deal, or a strategy—never leads to long-term success. The conversation moves into what’s actually happening in today’s real estate market, including Google’s growing role in home search, shifting power away from Zillow, the rise of all-cash buyers, refinancing trends, and major upcoming FinCEN reporting changes that will impact cash and entity purchases in 2026. Along the way, Annie and Chad tackle buyer anxiety, inspection realities, pricing myths, AI in real estate, and the hilarious but painfully real misconceptions clients have about home values. If you’re a real estate agent looking for mindset, coaching, market clarity, and practical talking points you can use with clients right now, this episode delivers insight, reassurance, and a reminder that you don’t need to panic to win. Listen in, share this episode with another agent who needs perspective, subscribe for weekly real estate coaching, and keep showing up ready to build a business that lasts.
E15: "Laugh With Us: Waking Up to Win Bloopers"
To kick off the new year, Waking Up to Win is doing something a little different, and a lot more honest. This New Year’s Day bloopers reel pulls back the curtain on what really happens before, during, and between takes as Annie Callaway and Chad Elledge record the podcast. From forgotten segments, hot mic moments, awkward transitions, technical hiccups, and unfiltered banter to real-time frustration, laughter, and chaos, this episode is proof that even the most polished real estate podcasts are built on imperfect moments. Along the way, you’ll get a behind-the-scenes look at the personalities, chemistry, and humor that power the show, reminding agents that success doesn’t require perfection, just consistency, authenticity, and the willingness to keep showing up. If you’re a real estate agent who’s ever stumbled through content creation, second-guessed yourself on camera, or needed a reminder that everyone starts messy, this episode is for you. Laugh with us, share this with a real estate friend who needs the reminder, hit subscribe, leave a review, and follow Waking Up to Win for weekly real estate motivation, mindset, coaching, and real conversations that help you keep winning, chaos and all.
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.
E13: "Why Relationships Still Win In Real Estate"
In this episode of Waking Up to Win, Annie Callaway and Chad Elledge dive into what it really takes to build a sustainable, relationship-driven real estate business in today’s shifting market. From mindset, affirmations, and the psychology behind law of attraction, to practical real estate strategies like pop-bys, client follow-up, pricing conversations, and managing difficult family dynamics at the closing table, this episode blends motivation with real-world coaching. Annie and Chad break down why staying top of mind matters more than ever, how great agents win business through consistency and relationships, and why boundaries with clients, parents, technology, and even AI are critical to long-term success. They also unpack current real estate headlines, including pricing challenges, market shifts, AI tools in real estate, and why authenticity will always outperform automation. If you’re a real estate agent looking to grow your business, sharpen your mindset, improve client relationships, and head into the new year with clarity and confidence, this episode will help you refocus, simplify your strategy, and remember what actually drives results. Listen in, apply what resonates, share this episode with another agent who needs it, and follow Waking Up to Win for weekly real estate motivation, coaching, and honest conversations about how to win in this business.
E12: "Real Estate Without Shortcuts: Growth, Referrals, and Industry Reality"
In this episode of Waking Up to Win, Annie Callaway and Chad Elledge dig into what it really means to grow as a real estate agent, personally, professionally, and financially, by stepping outside your comfort zone. From mindset shifts and business planning to knowing when to stay in your sandbox and when to refer business out, this conversation blends real-world coaching with honest industry insight. They talk through why growth never happens in comfort, how smart referral strategies can protect your clients and add significant income, and why many Realtors leave money on the table by trying to do everything themselves. The episode also unpacks current real estate headlines and trends, including changes coming from the National Association of Realtors, MLS policy updates, housing affordability forecasts, cash buyer reporting requirements, and Zillow’s climate data controversy, all with a practical lens for agents navigating today’s market. You’ll walk away reminded that working on your business, not just in it, means being intentional, building strong agent relationships, understanding your market expertise, and staying adaptable in an evolving industry. If you’re a Realtor who wants motivation, clearer strategy, and honest conversation about what it takes to win in real estate, this episode will challenge how you think about growth, referrals, and long-term success. Be sure to subscribe on YouTube and Spotify, leave a review if this episode resonates, and share it with a fellow agent who needs a reminder that growth lives just outside the comfort zone.
E11: “Buffini, NAR Updates & Realtor Reality Checks”
In this episode of Waking Up to Win, Annie and Chad dive into real-estate motivation, mindset, and the unfiltered realities of today’s shifting market, opening with a hilarious recap of late-night calls and the inspirational reminder that “everything seems impossible until it’s done.” They break down what’s happening inside the real estate industry, from getting certified in Buffini’s 100 Days to Greatness referral-based program, to how accountability and consistent systems help real estate agents become top producers. They also share why referral marketing, coaching, and proper mentorship are more critical than ever. They unpack the latest NAR updates, MLS access changes, and policy shifts affecting Realtors nationwide, plus how government shutdowns impact FHA, VA, and USDA loans and why some agents still struggle to navigate post-settlement rules. The episode also covers market predictions for 2026, pricing trends, commission conversations, and why buyer’s agents are asking for higher fees than in years past. Annie and Chad explain how Realty One Group is evolving its training, how mentors and coaches should support new agents, and why real estate professionals must stay educated as the industry transforms. They also tackle the wild “what the floop” story of the week, an agent being taken to small claims court over a broken fireplace, and discuss whether a home feature has value if it doesn’t actually work. Make sure to subscribe, leave a quick review, follow us on social media, and send in your own chaotic or unhinged real estate stories. We might share them on the next episode. Keep learning, keep building your business, and keep waking up to win.
E10: "Your Buyer Deserves Better Info"
This week on Waking Up to Win, Annie and Chad break down the real conversations every Realtor needs today including business planning, market shifts, HOA surprises, agent mistakes, legal updates, and the mindset required to succeed. After a chaotic, funny intro (sick dogs, husbands, and the McRib), they dig into why “If you fail to plan, you’re planning to fail” is the most important truth in real estate. You’ll hear how simple weekly planning and clear goals can transform an agent’s entire business.They share real stories from their brokerage, clients blindsided by HOA rules, agents skipping research, buyers confused about lake rights, zoning, chickens, and ordinances. They show how quickly misinformation spreads and why great Realtors protect clients by digging into bylaws, restrictions, and development changes before problems arise.The episode also covers major industry news: the Zillow lawsuit involving alleged RESPA violations, big brokerage mergers (Century 21, Coldwell Banker, Compass, Remax, Anywhere), and the shifting culture agents need to be paying attention to. Annie and Chad also unpack the debate around a 50-year mortgage and how affordability challenges are changing the path to homeownership.Key message: agents need real business plans, clients need informed advisors, and professionalism matters now more than ever. They wrap with a “What the Floop” moment about a viral agent bragging about 1% listings—and why discounting your value only hurts your brand.If you’re a Realtor looking to grow, stay informed, avoid legal missteps, and run your business with intention, this episode brings humor, clarity, and practical coaching. If it resonated, hit Follow/Subscribe, drop a review, and share it with another agent who needs the real talk.
E9: "From Miami to Mayhem: Realtor Lessons & Laughs"
In this episode of Waking Up to Win, hosts Annie Callaway and Chad Elledge return from Miami with big energy, plenty of laughs, and a fresh dose of real-estate insight. From their trip to Realty ONE Group’s Summit and what’s next for the company with ONE Talks and regional conferences, to hilarious stories about attics gone wrong, buyers falling through ceilings, and the latest industry headlines, this episode is a blend of chaos and clarity every Realtor will relate to. Annie and Chad dive into the week’s top real-estate news, including Fannie Mae’s new credit-score changes, Zillow’s private-listing ban, and Anywhere & Compass’s merger, breaking it all down in plain language for agents who want to stay ahead of market trends. They also share lessons on agent ethics, client communication, and why staying adaptable is key in 2025’s fast-changing market. If this episode made you laugh, think, or text your real-estate bestie “this is so us,” do us a favor and subscribe, leave a review, or share with someone who needs a reminder that even in real estate chaos, you can still wake up to win.
E8: "Be Kind, Follow the Rules, and Don't Pull the Sign Early"
In this episode of Waking Up to Win, hosts Annie Callaway and Chad Elledge bring their signature mix of humor, honesty, and real estate wisdom to another week of chaos, closings, and lessons learned the hard way. From weather woes and wedding weekends to unpacked boxes and hilarious sayings passed down from Grandma Gladys, this conversation proves that life, and business, are all about learning to let go and laugh through it. The hosts dive into an outrageous real estate story involving a buyer’s agent gone rogue, a premature walkthrough, and a “contractor cameo” before the deal was even funded. Along the way, they share key takeaways every Realtor needs to remember: don’t be an ass, be kind, follow the rules, and for heaven’s sake, never pull the yard sign before funding clears. As always, the duo blends humor and hard-earned lessons, weaving in the week’s biggest real estate headlines, from falling mortgage rates and rising inventory to the latest NAR reform discussions and the importance of pricing homes correctly in a changing market. You’ll also hear their unfiltered thoughts on professionalism, lazy agents, and why soft skills like kindness and patience can make or break your business in 2025. Tune in for the laughs, stay for the lessons, and walk away ready to sell smarter, lead better, and keep waking up to win. Don’t forget to subscribe, leave a review, and share this episode with your favorite real estate bestie, because every deal deserves a good story, and every agent could use a reminder to chill, communicate, and close with class.
E7: "The Episode That Had Everything: Lien Waivers, Laughs, and Lessons"
In this hilarious and insight-packed episode of Waking Up to Win, hosts Annie Callaway and Chad Elledge, alongside producer Erin, dive into the real stories, real lessons, and real laughs behind life in real estate. From Annie’s unforgettable “fall heard around the parking lot” to Chad’s over-the-top sound system purchase, this episode reminds us that mindset and momentum matter more than perfection. You’ll hear how the team turned a simple “One License, One Future” event into an inspiring opportunity for new agents to rethink their futures, and how they mix motivation with practical education to help people escape the corporate grind. Chad and Annie also break down key real estate insights: what to know about mechanic’s lien waivers, signing separately at closing, rising builder confidence, and the latest industry headlines. They also dug into Zillow pulling Matterport 3D tours to new AI tools for realtors, falling mortgage rates, and the Road to Housing Act shaking up affordable housing. With equal parts comedy, coaching, and chaos, Annie and Chad prove that success in real estate takes more than contracts. It takes confidence, adaptability, and a sense of humor. You’ll walk away with motivation to “challenge your limits, not limit your challenges,” and maybe a new appreciation for staying upright during showings. Tune in, subscribe, and share this episode with your favorite agent who needs a reminder that even the best fall down sometimes—but winners always get back up.
E6: "Hope Is Not A Method"
In this week’s episode of Waking Up to Win, hosts Annie Callaway and Chad Elledge tackle one of the hardest truths in real estate — hope is not a strategy. From pricing homes realistically to communicating with clients who don’t always want to hear the truth, this episode is a masterclass in what it means to lead with honesty, confidence, and kindness.Annie shares how her affirmation of the week — “I have the courage to speak my truth and the heart to serve it with kindness” — applies to agents who struggle to have hard conversations with sellers, while Chad dives into how misplaced optimism and poor communication can cause listings to sit far longer than they should. Together, they explore how real estate professionals can stay grounded when the market feels shaky, offering unfiltered insight into what’s really happening behind the headlines.From pricing strategies and staging advice to managing seller expectations, the duo breaks down what’s working, what’s not, and how to help clients make smarter, faster decisions — even when mortgage rates are pushing 8%. Plus, they discuss the latest housing market headlines: rising interest rates, record-low home sales, foreclosures ticking upward, and the continued pressure on agents to adapt in an unpredictable market.But it’s not all doom and gloom. Annie and Chad remind listeners that mindset always matters more than market conditions. Whether you’re a new agent learning how to price your first listing or a seasoned pro trying to keep clients calm, this episode will challenge you to be bold, stay honest, and stop relying on hope to close the deal.Tune in now for unfiltered real estate talk, practical coaching, and a few laughs along the way.Subscribe to Waking Up to Win on Spotify, YouTube, or Apple Podcasts for weekly real estate motivation and actionable strategy.Follow @WakingUpToWinPodcast and share how you’re “speaking your truth with kindness” this week — because it’s always a good time to grow your business and your mindset.
E5: "Renters, Realtors, and Ridiculous Rules"
In this episode of Waking Up to Win, hosts Annie Callaway and Chad Elledge dive into what every real estate agent is talking about, the reality behind today’s housing market, the truth about buyer representation, and the future of the real estate industry as interest rates climb and inventory shifts. Annie and Chad bring their signature mix of humor, insight, and unfiltered coaching to hot topics like rising mortgage rates, AI-powered tools like Zillow’s new ChatGPT integration, and why so many buyers are still renting instead of building equity. They challenge agents to stop waiting for the “perfect market” and start taking action, because real success in real estate is built on mindset, not market conditions. From the 7.5% interest rate headlines to the surprising new legislation shaking up directional signs in Wentzville, Missouri, this episode breaks down what’s changing, what’s staying the same, and what every agent needs to do to stay relevant, resilient, and profitable in 2025.Chad gets fired up about agent accountability and buyer education, while Annie calls out the myths that keep buyers stuck, reminding everyone that the best time to buy or sell a home isn’t when the headlines say it is, but when you’re ready. Together they unpack everything from rental trends and affordability myths to the importance of integrity, consistency, and following through on what you say you’ll do, both in business and life.If you’re ready to stop making excuses and start building momentum, this episode will give you the motivation and strategy to do exactly that. You’ll laugh, you’ll learn, and you’ll probably rethink the way you talk about commissions, signs, and what really drives this business forward.Listen now on Spotify, YouTube, Apple Podcasts, or wherever you get your podcasts.Follow Waking Up to Win for more unfiltered real estate talk, business strategy, and next-level motivation every week.Tag @WakingUpToWinPodcast and share your biggest takeaway. What are YOU committing to this week to grow your business and your mindset?
E4: “Market Shifts, Lawsuits & As-Is Chaos: Real Talk for Real Estate Agents”
Welcome back to Waking Up to Win with Annie and Chad — your go-to podcast for real estate motivation, high-performance mindset shifts, and practical coaching that moves you from stuck to top producer. This week’s episode is packed with powerful conversations around taking action now instead of waiting for “one day,” how to find clients anywhere, market headlines every agent needs to know, and some unfiltered real talk about the realities of contracts, inspections, and industry best practices.From wedding season networking to unexpected client wins at the phone store, Annie and Chad remind us that today can be Day One. They break down the latest housing market trends — including interest rate updates from the Federal Reserve, rising mortgage rates, the impact of CoStar Group acquiring Matterport, leadership shakeups at realtor.com, and the lawsuit against Zillow by the Federal Trade Commission. Plus, they dive into how AI is shaping the future of real estate and what agents can do to stay ahead of the curve.Key takeaways include the mindset shift of turning “one day” into “Day One,” why you can find leads anywhere with the right attitude, what steady interest rates really mean for buyers and sellers, why vague “as-is” language can be a legal landmine, and how careless feedback can land agents in serious trouble. Annie and Chad don’t hold back — they give agents the clarity, strategy, and motivation to build a sustainable business and dominate their market.If you’re a real estate agent, team leader, or industry professional looking to grow your business, this episode is a must-listen.Subscribe, rate, and review Waking Up to Win on your favorite podcast platform.Follow us on social media for daily motivation, training tips, and behind-the-scenes conversations.Share your own wild real estate stories — we might feature them in a future episode!Don’t just survive the week. Build your business, own your mindset, and keep waking up to win.
E3: "Real Estate Under Pressure: Compassion Acquisitions, Client Families, and Realtor Resilience"
On this episode of Waking Up to Win, Annie and Chad dive into the realities of being a real estate agent in today’s market, where patience and grace aren’t just affirmations, they’re survival skills. From handling first-time homebuyers with helicopter parents to navigating tricky negotiations, they share real stories that every Realtor canrelate to. They also unpack the breaking industry news about Compass acquiring Anywhere Real Estate for $1.6 billion, making it the largest brokerage in the world, and what that means for agents, clients, and the future of the realestate market.With unfiltered honesty, they explore how to maintain professionalism when family dynamics complicate transactions, the importance of remembering who yourclient really is, and how big brokerage moves could reshape the way agents do business. Along the way, they sprinkle in humor, candid moments, and even a wild real estate headline that has to be heard to be believed (yes, 159,000 text messages).At the heart of this conversation are key takeaways every real estate agent needs to hear: the power of effective communication, the necessity of setting boundaries with clients and their families, and the resilience it takes tothrive in a shifting market. Whether you’re navigating your own difficult deal, watching the Compass–Anywhere merger unfold, or just looking for some encouragement to keep pushing forward, this episode delivers insight,motivation, and the kind of truth that helps agents grow stronger businesses.If you’re a Realtor, real estate professional, or simply curious about how the industry is evolving, this episode is packed with lessons, laughs, and leadership strategies you won’t want to miss.Don’t forget to subscribe to Waking Up to Win on Spotify, YouTube, and Apple Podcasts. Share this episode with your fellow agents, leave us a review, and follow along for bold conversations, real strategies, and the unfiltered truth about real estate.
E2: "Soda Wars, Zillow Lawsuits & Solving Client Problems"
Welcome back to Waking Up to Win with Annie and Chad, the unapologetically real podcast where real estate, mindset, and motivation collide. This week’s episode is packed with laughter, raw truths, and real-world coaching for agents who want to stop running ragged and start building a business that actually wins.From hilarious soda-stealing stories to the serious realities of rising mortgage rates, housing affordability challenges, and messy brokerage promises, Annie and Chad pull back the curtain on what’s really happening in real estate right now. You’ll hear why selling homes isn’t about selling at all, it’s about solving problems, and how to stay focused when the headlines scream chaos. We even dive into Zillow vs. Compass lawsuits, home seller concessions, shady listing agent practices, and whether brokers should really be promising leads in the first place.The big takeaway? Real estate isn’t about waiting on perfect market conditions, magical leads, or the right brokerage pitch. It’s about taking ownership of your business, staying solutions-focused, and refusing to let the noise distract you from your goals.If you’re a realtor, broker, or entrepreneur looking for honest insights, sharp strategies, and a good laugh along the way, this episode delivers.Don’t just survive the market, thrive in it. Hit subscribe on YouTube, follow us on Spotify and Apple Podcasts, and drop a quick review so more agents can find this show. Got a wild real estate story? Send it to us by submitting on our podcast - https://www.wakinguptowinpodcast.com/ We might just share it in an upcoming episode. And remember, don’t just wake up…wake up to win.
E1: "Lawsuits, Listings That Won’t Sell, and Owning Your Success in Real Estate"
Welcome to the very first episode of Waking Up to Win with Annie and Chad, your go-to podcast for real estate motivation, mindset shifts, and the kind of coaching that helps agents stop running ragged and start building intentional success. In this debut episode, we dive into the current Compass vs. Zillow lawsuit, what MLS changes mean for real estate agents, and why transparency in listings truly matters for clients. We also share real stories from the field, including the challenges of selling a house that smells like cigarette smoke, what agents can really do to help their sellers, and how buyers actually react when strong odors or poor curb appeal get in the way. Along the way, Annie and Chad unpack the truth about creating success one intentional move at a time, why excuses don’t sell houses, and how to keep your focus on clients instead of industry noise. From navigating smoke remediation costs to understanding seller options in today’s changing market, this episode is full of practical lessons and unfiltered real estate talk that every agent needs to hear. If you’ve ever wondered what these big lawsuits mean for your daily business, how to advise clients when houses won’t move, or whether a realtor needs to own a home to give professional advice, this episode will give you both laughs and clarity. Join us every week as we mix coaching, real talk, and industry news to help you stay motivated and competitive in real estate. If this episode resonated with you, hit subscribe, leave us a review, and share it with your real estate bestie. Follow us on social media for daily tips and send us your own wild or unhinged real estate stories—we may feature them in a future episode. Don’t just survive this week in real estate—wake up to win.