There are people in every great story who were there before the story became great. Before the stages, before the social media following, before the seminars that sell out and the YouTube channel that launched a movement. Jessy is one of those people.

I sat down with Jessy Castillo Cruz recently on my show, and what unfolded was less of a standard business interview and more of a living archive. Jessy knew Andy and Jackie Elliott when they were all selling cars together at a sprawling dealership in Oklahoma. She saw Andy post on Craigslist before anyone else thought it was a sales tool. She watched him drag a folding lawn chair to the front of the used car lot just to greet customers before they even had a chance to park.

“He was selling 60, 70 cars a month,” Jessy told me. “He was a wizard at it back then. He always was.”

I had to laugh because I remember those credit card numbers we used to write on legal notepads. I had a notebook for every year. If I signed up a dealer or sold a seminar ticket, I would flip to last year’s notebook to find the card. We were building something real before we even had the systems to hold it. Jessy was there for all of it.

The Oklahoma Days

Long before the Elliott Group became what it is today, it was a group of people grinding together under the Oklahoma sun at a mile-long dealership that housed Toyota, Honda, GMC, and more. Jessy was on the Toyota side. Andy worked the used car lot next door. Jackie came in as the BDC manager when internet sales were just beginning to be taken seriously as a business driver.

The three of them became friends in the natural way, through proximity, shared hustle, and the kind of honest connection that forms when people are working hard toward something without knowing exactly what it will become.

What I love about Jessy is that she was there for all of it, including things even I did not know about until this conversation. She watched Andy pursue Jackie. She was present for the whole chase. “I was there when he asked her out,” she told me, laughing. “Andy started pursuing her, and he got her.”

And I have to be honest, I also heard a story in that conversation that had me in tears laughing. Apparently, before Jackie, Andy was dating three women at the same time. All three of them compared notes, figured it out, and drove to the dealership lot together to confront him. Jackie witnessed the whole thing and apparently thought to herself, I am absolutely not dating that man. And then she did. And the rest is history.

Life eventually scattered them. Jessy moved to Florida, then Arizona. Andy and Jackie followed their own path. But the friendship never actually ended; it just paused between conversations. When Jessy told Jackie she was moving to Arizona, Jackie’s response was simple: “Well, I’m starting this company.”

Cleaning Toilets and Being Seen

Jessy was one of the first people Jackie ever sent the Elliott YouTube channel link to. She subscribed immediately. She watched it grow. And when the opportunity came to be part of what Andy and Jackie were building, she offered to start anywhere.

“I offered to clean the toilets,” she told me, without a trace of irony. “I just wanted to be involved. I just wanted to be a part of it.”

What happened next is the kind of moment that defines a person’s trajectory. Andy sat her down and told her he saw more in her than she was asking for. Instead of assigning her janitorial duty, he began training her himself, sitting with her at night while he and Jackie recorded videos, giving her specific direction, building her role from the ground up.

Jessy had spent ten years in the auto industry and another ten in mortgage. She knew the dealership world from the inside. She understood what it felt like to be a salesperson excited about a six figure opportunity, selling someone else’s inventory for a fat commission, working a floor that could make or break your month. That experience became the foundation for one of her most important roles at the Elliott Group: leading the dealer division.

“I love my dealers,” she said. “I come from cars. I understand them.”

Military Roots and a Gumball Machine Philosophy

Jessy comes from a military background, and she draws a direct line between that experience and the discipline, structure, and values she brings to her work today. My own parents served, so this part of our conversation felt personal to me, too.

“I loved being part of something bigger than myself,” she said. “In the military, you’re choosing to sacrifice your own life for the life of others. Here, we’re choosing that same spirit but to empower others to fight in a different form.”

She described the Elliott Group’s culture as having a similar structure to military life, clear values, high standards, and a sense of purpose that extends beyond any individual. But where military service is about protecting lives, this work is about transforming them.

I have my own metaphor for what our team looks like from the inside. I describe it as a bag of gumballs. Pink ones, white ones, licorice ones, purple ones, all different flavors in the same bag, all on the same mission. When I asked Jessy what makes her different from everyone else in that bag, her answer came right back to her roots. She is the person who understands the dealers because she has lived that life. She is the person who cares not just about the result but about the human behind the result.

And she has always wanted to be part of a gumball machine rather than operating alone. “I’m such a big, loud, vibrant person,” she told me, “but I know that if I could be in a gumball machine, I would be so much better.”

Auntie Jessy and the Stability of Presence

One of the things I appreciate most about Jessy, and I said this to her directly during our conversation, is her gift for showing up for people. Not just professionally, but personally. I have gone to her when I could not talk to the guys on the team because they just did not get it. She gets it. She has always gotten it.

Jessy’s way of describing her role in our organization is one of my favorite things she said during the whole conversation. She sees Andy and Jackie as the mom and dad of the Elliott Group. That makes her the aunt.

“I like to be the aunt stability,” she said. “If you got mom and dad as Andy and Jackie, I’m your aunt that you can come to and trust and believe. Mom and dad will hear about it, and if not, we’ll resolve it.”

That warmth is not performative. I have felt it firsthand. I remember her being kind to me in a season of my life when I was going through something hard, offering to take a photo of me at the whiteboard, inviting people in, just being present. Four years later, that same energy is woven into the culture we have all built together.

And if you ever need a party setup that stops the room, Jessy also runs a balloon and events business called “Pop of Joy AZ”. The backdrop she did for a recent bridal shower was genuinely stunning. I am putting that in the description so you can find her.

What She Wants to Be Known For

When I asked Jessy what she wants to be known for in the lineup of Elliott Group voices, the answer came with quiet conviction: total recreation.

Jessy attended a seminar where she made a decision to lose weight and fully reinvent herself. She followed through. And now she wants to hold that torch as the living proof that full female transformation is real and available, especially for women who might feel like the window has passed.

“I’m gonna be one of the oldest at the group, and I’m gonna be the female OG,” she told me. “I love that it gives older women hope.”

She is 45, navigating hormonal changes, raising a teenager, running a business, and showing up every day with the kind of energy that makes people forget all of that is happening simultaneously. She told me she is not competing with anyone else’s physique or anyone else’s timeline. She is competing with life itself, and she is winning.

I believe her. I have watched her.

The Advice She Leaves You With

At the close of our conversation, I asked Jessy what she would say to anyone listening, whether they are a stay-at-home mom looking to find her identity again, a business owner questioning the next move, or someone ready to walk away from corporate America and try something that actually feels alive.

Her answer was rooted in faith and stripped of complication.

“The stone has been rolled away,” she said. “There is nothing stopping you other than you. Just let God take it one day at a time. Dream really, really big.”

She has lived that. From Oklahoma car lots to Arizona culture building, from offering to clean toilets to leading a dealer division, from watching something great being built to becoming irreplaceable inside it. Jessy’s story is proof that showing up fully, across years and seasons and cities, is its own kind of superpower.

I am grateful she let me tell it.

Shoot for the moon. Land with the stars. And when you find your gumball machine, get in it.

About me:

I am currently a Master Facilitator for The Elliott Group in addition to being on the board of advisors for our Cultural Transformation Department in ELLIOTT ARMY.

With over 14 years of client service experience, I have held substantial leadership roles in the automotive industry. I’m also an accredited coach, a writer, a speaker, and a triathlon finisher. To contact me for engagements, you can reach me at [email protected].

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