Waking Up To Win
Annie Callaway and Chad Elledge
Publishing Details
About This Podcast
Explore Statistics
Recent Episodes
S1E27 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…
S1E24 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…
S1E25 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…
S1E24 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…
S1E23 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…
S1E22 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…
S1E21 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…
S1E20 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…
S1E19 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.…
S1E18 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.…
S1E16 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…
S1E14 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…
S1E15 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,…
S1E14 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…
S1E13 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…
S1E12 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…
S1E11 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…
S1E10 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…
S1E9 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…
S1E8 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…
Frequently Asked Questions
Waking Up To Win has published 27 episodes since September 2025, covering topics in Business, Entrepreneurship.
Waking Up To Win is currently highly active with new episodes weekly. Average episode length is 36m.
Similar Podcasts
The School of Greatness
Lewis Howes
1,946 episodes
The Tim Ferriss Show
Tim Ferriss: Bestselling Author, Human Guinea Pig
873 episodes
THE ED MYLETT SHOW
Ed Mylett
685 episodes
Craig Groeschel Leadership Podcast
Life.Church
194 episodes
All-In with Chamath, Jason, Sacks & Friedberg
All-In Podcast, LLC
390 episodes
Earn Your Leisure
iHeartPodcasts
1,483 episodes