Episode 1: Why We Started Hustle Humbly

Welcome to the very first episode of Hustle Humbly! In this episode, we break down why we started Hustle Humbly—a podcast created to build connection, encourage authenticity, and cut through the noise in the real estate industry. As two successful but very different real estate agents in Baton Rouge, we share how choosing community over competition shaped our careers and our friendship. If you’re a new agent, struggling with burnout, or wondering if you’re cut out for real estate, this episode is for you.

Who We Are

Meet your hosts: Alyssa Jenkins and Katie Caldwell. Katie began her real estate career in 2005 after leaving retail management, while Alyssa jumped in after completing her MBA in 2012. Both of us found real estate appealing because we wanted control over our income and careers. As full-time agents in different brokerages, we chose collaboration over rivalry and found strength in our shared experiences.

How the Podcast Idea Began

Why we started Hustle Humbly stemmed from Alyssa’s overflowing calendar of coffee dates with new agents. After her first year in real estate—where she sold 12 homes for $4.4 million in volume—agents began reaching out constantly for advice. These coffee dates became so frequent that she started grouping them together. Eventually, with limited time and growing demand, a podcast became the perfect way to share insight at scale.

The Power of the Coffee Date

Our real estate journeys led us to each other through one of Alyssa’s educational webinars. Katie, impressed by Alyssa’s willingness to help other agents, reached out and scheduled her own coffee date. That one meeting led to a meaningful friendship and now a co-hosted podcast. Coffee dates became the foundation of our mentorship mindset and inspired the mission behind Hustle Humbly.

Common Struggles of New Agents

Many agents Alyssa met were on teams or following strict sales scripts that didn’t fit their personalities. They felt lost, unsure of what to do, or worse—afraid to admit they were struggling. Often, agents asked that their meetings remain confidential. This told us that the real estate culture wasn’t fostering openness or support. We wanted to change that.

There Is No Secret Sauce

What most new agents really want is a shortcut. But the truth is, there’s no secret. Real estate success comes from consistency, authentic relationships, and a willingness to experiment and grow. Many agents feel discouraged to hear that, but others feel relieved. If you’re not great at cold calling, that’s okay. You just need to find your way—not copy someone else’s.

Lessons from Mentorship and Early Wins

Alyssa shares how mentors and coffee conversations shaped her career. From early recognition in her brokerage to rising through the ranks without fully realizing how well she was doing, every step added clarity and confidence. Katie recalls how shadowing her broker and immersing herself in every training opportunity helped her build the foundation for a thriving career.

A Real Talk About Year One

We won’t sugarcoat it: the first year in real estate is hard. You face rejection, inconsistent income, and emotional ups and downs. But it’s also where you learn the most—about yourself, your work ethic, and what kind of business you want to build. If you’re in year one through three, or considering real estate as a career, this podcast is your new home for honest advice and practical encouragement.

Coming Up Next…

In the next episode, we’ll dig into real estate culture and how it affects new agents. After that, we’ll cover the “mindset meltdown” and offer tools to navigate those tough first years. We’ll also be inviting guests in and out of the industry to share their own unique experiences.

Our Weekly Toast: Cheers to Our Mentors

At the end of every episode, we toast to someone who has helped us along the way. This week we toast:

• Geoffrey Welsh – Alyssa’s early mentor who encouraged her to lead in the industry.

• Martha Chauvin – Katie’s broker and mentor who gave her the tools and confidence to grow her career.

Cheers to those who lift others up and lead with generosity!

Subscribe, Share, and Send Us Your Wins

Follow us on Instagram and Facebook @hustlehumblypodcast. If you have a question or a topic idea, send it to hustlehumblypodcast@gmail.com. Be sure to subscribe and leave a review so others can find us. Don’t forget to send in your wins—we want to celebrate with you!