Waking Up To Win

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...

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 wan...

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 es...

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 developm...

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 a...

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...

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 al...

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 extraordina...

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 cycle...

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...

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 w...

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, a...

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, thi...

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 af...

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 traditi...

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...

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 frustrati...

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 Sim...

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...

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 insig...

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...

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 rea...

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...

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 t...

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 perfect...