Waking Up To Win

Annie Callaway and Chad Elledge
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Waking Up to Win is the no-fluff, all-fire podcast for real estate agents who are ready to stop playing small and start building a business that actually works. Hosted by Annie Callaway and Chad Elledge, top-producing agents, brokerage owners, and your new favorite truth-telling duo, this show dishes out bold strategy, unapologetic motivation, and the realest real estate conversations you won’t hear anywhere else. From tactical advice that gets results to mindset shifts that move mountains, Waking Up to Win is where chaos meets clarity, humor meets hustle, and nothing is off-limits.

  1. E21: "Market Reality, Myths, and Momentum"

    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 The conversation takes a sharp turn into real estate investing myths, including the outdated one-percent rule, cap rates, corporate buyers, and why mom-and-pop investors are struggling to compete in a market dominated by long-term institutional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
  2. E20: "Realtors, Do Better: Marketing, Lawsuits, and Industry Reality"

    FEB 5

    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.

    36 min
  3. E19: "Real Estate News, Strong Opinions, and No Sugarcoating"

    JAN 22

    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.

    45 min
  4. E18: “First-Time Buyers, Lifestyle Renters, and Market Reality”

    JAN 15

    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.

    30 min
  5. E17: "Candid Convos: Tammy Mueller"

    JAN 12

    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.

    18 min
  6. E16: “What’s Meant for You Won’t Miss You: Real Estate Mindset for 2026”

    JAN 8

    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.

    34 min
  7. E15: "Laugh With Us: Waking Up to Win Bloopers"

    JAN 2

    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.

    5 min
  8. E14: “Real Estate Business Planning That Actually Works”

    12/25/2025

    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.

    36 min
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About

Waking Up to Win is the no-fluff, all-fire podcast for real estate agents who are ready to stop playing small and start building a business that actually works. Hosted by Annie Callaway and Chad Elledge, top-producing agents, brokerage owners, and your new favorite truth-telling duo, this show dishes out bold strategy, unapologetic motivation, and the realest real estate conversations you won’t hear anywhere else. From tactical advice that gets results to mindset shifts that move mountains, Waking Up to Win is where chaos meets clarity, humor meets hustle, and nothing is off-limits.

Information

  • Creator
    Annie Callaway and Chad Elledge
  • Years Active
    2025 - 2026
  • Episodes
    21
  • Rating
    Explicit
  • Copyright
    © Annie Callaway and Chad Elledge
  • Show Website
    Waking Up To Win