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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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. 

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.