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.

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.

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.

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.

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.

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. 

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.

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.

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.

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.