Waking Up To Win - The Podcast

Waking Up To Win - The Podcast Hosted by Annie Callaway & Chad Elledge, this podcast brings real talk, real strategy and no fluff.

Just bold motivation + unfiltered truth for real estate agents ready to build businesses that actually work. Waking Up to Win is the bold, unfiltered podcast for real estate agents who are done with fluff and ready to build businesses that actually work. Hosted by Annie Callaway and Chad Elledge, co-owners of Realty ONE Group Trifecta in O'Fallon, MO, this podcast delivers real talk, real strategy

, and real results. We’re here to elevate and empower ambitious agents through honest conversations, tactical coaching, and motivating mindset shifts. Whether you're just getting started or scaling to the next level, you’ll find the truth, tools, and energy you need to win, your way.

🎧 New episodes dropping 2x per week
🔥 Unapologetically bold. Always real.
📍 Based in O’Fallon, MO
👉 Listen now wherever you get your podcasts

05/07/2026

Your life doesn’t need another “catch up” day… it needs an Ultimate Admin Day. ✅🔥

In Episode 29 of the Waking Up To Win - The Podcast, we’re talking about the powerful concept from Mel Robbins that can help you reset, refocus, and finally tackle the things you’ve been putting off.
Sometimes winning starts with organizing the chaos. 👏

🎧 Episode 29 is out now — watch the full conversation and start building momentum.

03/31/2026

Some houses are just special…IYKYK! 😆👏

03/30/2026

Working in your real estate business is the day-to-day hustle. Working on your business is the strategy behind the success.

You need both, but knowing when to shift is the game changer!

Thanks again to our guest, Sherry Ruyle for a great conversation! Listen to the full episode (26) of Waking Up To Win now! 👏🎧

03/24/2026

Welcome top producing STL Realtor, Sherry Ruyle to Waking Up To Win!! This was a great conversation between Chad and Sherry that you don’t want to miss.

Listen now to hear Sherry’s journey through real estate and her amazing advice to Realtors everywhere!

03/18/2026

Stop looking for "vendors" and start building partnerships. 🤝

In this clip from Candid Convos, Drew Q. with USA Mortgage breaks down why a personal connection is the secret sauce to surviving the high-stress world of real estate. When things get transactional, the stress goes up. When you're peers, the win is shared. 🏆

Are your partners just vendors, or are they in the trenches with you? 👇

03/18/2026

What do people say about you when you're not in the room? 🗣️

That’s the ultimate metric of leadership. Drew Q., a St. Louis loan officer with USA Mortgage, stops by the studio to challenge us on how we show up for our teams and ourselves.

Don't miss the newest Waking Up to Win: Candid Convos episode! It's SO good! 🎙️✨

03/16/2026

When I remember I’m THAT Realtor! 😆👏

03/06/2026

Raise your hand if you’re a Realtor that gets it. 🙋

03/06/2026

The ONE Thing we can't get right 😅

If rescheduling was an Olympic sport, Chad and Annie would have the Gold. 🥇 Finding a window between the brokerage, being agents themselves, and the 'last-minute' fires is a 1,000,000% struggle. Drop a '🙋‍♂️' if your calendar looks like a game of Jenga right now!

03/05/2026

The secret ingredient to success? 🤫 Show up.

This week, we’re flipping the mic on our very own producer! She’s seen firsthand the direct correlation between showing up consistently and seeing those business wins stack up. Success isn’t just about what you do, it’s about where you show up. 🚀

Link to the full epsidoe in the comments!👇

Address

2307 State Highway K
O'Fallon, MO
63368

Telephone

+13143916789

Website

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