1605 – Success Leaves Clues with Jess Stewart

In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks to the Business Coach, Speaker & Founder of Jess Stewart LLC, Jess Stewart.


Jess Stewart, a strategic business guide based in Texas, talked about her mission to help leadership teams and companies achieve their full potential. Jess offers valuable insights and practical tips on scaling and executing business strategies.

But Jess doesn't just identify the problem; she also offers a solution. She conducts intensive and engaging sessions with the leadership team when working with clients. These sessions involve breaking down the company, identifying gaps, and creating a customized approach based on best business practices. Jess also holds quarterly sessions to ensure accountability and progress toward the annual plan.

In addition to her work with leadership teams, Jess has expanded her offers. She now provides a “climb” program, where she closely collaborates with leadership teams. She has also started mastermind programs for ascending leaders not part of her teams. These programs involve monthly Zoom meetings, where Jess leads content and facilitates discussions among participants across the United States.


About Jessica Stewart:

Jess is a fearless and highly accomplished leadership team coach, strategic advisor, and business guide with a lifetime of hard-won successes under her belt.

Raised by a Marine Corps pilot on a cattle operation in the mountains, Jess learned the keys to running an entrepreneurial company. Grit, hard work, and no complaining infused a work ethic in Jess that she lives and breathes today.

After college, Jess became a teacher. After a relocation with her husband to a city with no teaching jobs, Jess decided to start a medical billing business from her kitchen table with two young children under her feet. Though she knew nothing about medical billing, the lessons learned from her dad “stuck.” Failure has never been an option for Jess. Jess worked every job inside her company, grew it to two US locations, and an international division.

The story was not all roses. Hitting the ceiling was not an unfamiliar feeling for Jess. These painful times taught her to assemble a leadership team and company that operated on world-class systems and processes. When the unexpected opportunity for exit came, she could say yes!

Today, Jess is devoted to helping other entrepreneurs, leadership teams and companies run better businesses and live better lives.

Jess lives in Texas with her husband Murt, and two children Cora and Murt V.


About Jess Stewart LLC:

Jess Stewart LLC is a firm that believes in the potential of companies to reach their biggest goals and focuses on equipping top leadership with the necessary guidance to steer growth. Leveraging first-hand experience, the firm provides professional consulting services designed to help navigate the complexities of business expansion.

It acknowledges the importance of experienced leadership in company development and tailors its approach to ensure client success. Jess Stewart LLC embodies the entrepreneurial spirit and commitment to business excellence, making it a go-to resource for companies aiming to excel in their industry.

The ultimate mission is to facilitate growth and transformation for its clients through strategic leadership support.


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Josh (00:00:05) - Hey there, thoughtful listener. Would you like consistent and predictable sales activity with no spam and no ads? I'll teach you step by step how to do this, particularly if you're an agency owner, consultant, coach or B2B service provider. What I teach has worked for me for more than 15 years and has helped me create more than $10 million in revenue. Just head to up my influence and watch my free class on how to create endless high ticket sales appointments. You can even chat with me live and I'll see and reply to your messages. Also, don't forget the thoughtful entrepreneur is always looking for guests. Go to up my influence com and click on podcast. We'd love to have you. With us right now. It's Jess Stuart. Jess you are the your strategic business guide your found on the web at Jess thank you for joining us.

Jess (00:01:10) - Thank you for having me Glad to be here.

Josh (00:01:12) - And you're based in Texas. And tell me what you do as a strategic business guide.

Jess (00:01:17) - Yeah, So I'm based out of Fort Worth and love the city of Fort Worth, but I'm a strategic business guide.

Jess (00:01:22) - And what I do is I help leadership teams and companies scale and execute on strategy. So what I have identified is that us visionaries, me being one of them, really struggle with articulating our vision down to our team, to the ability for us to actually execute and scale. And so being that I've been there and I've sat in every seat of my own company before I sold it, it was really, really hard until I discovered how to do it. And that's when life became bliss for me. And I lived the last four years of my career making more money professionally and personally than I ever had. And it was by implementing a program that similar to what I do today. So I summarize it with this, Josh, is that I struggled, I succeeded, and now I want to be significant in other people's lives. And I do it through working with leadership teams and organizations where I rope in with them and help them execute on and scale.

Josh (00:02:15) - So what's the disconnect then that you're talking about? So like, if the leader has the vision and it's, you know, it's not being disseminated within the organization, why is that the case?

Jess (00:02:25) - You know, it's unintentional most of the time, right? And I was one of them.

Jess (00:02:30) - So I'll throw myself out there. Is that example? But what I would do is I would go by myself and I would build this vision of where I wanted to take the organization by myself, and then I would bring it back to my team and be like, Here's what we need to do. And I would pound the, you know, the battle rhythm drum and then nothing would happen and we might execute for the next 30 days, 60 days. But nobody really knew how to move the puzzle pieces to get that vision to reality. And so what I identified was that the gap was, is that you build the vision as a team. So you have to build your, you know, your leadership team, your people as a visionary, bring them in and share that vision and say, how do we do this? Right? Because in our head as visionaries, man, we're so good at looking at this big giant mountain and saying, Hey, we're here and I see the finish line there, but we're really bad at describing it all the steps to get there.

Jess (00:03:31) - And that's why we have a leadership team, right? We hire for those weaknesses to come in and help us put that vision to reality.

Josh (00:03:38) - Yeah, and what does that typically look like when you're looking with like, say, someone's listening to us, You know, they've never worked with a consultant in that fashion. What does that end up looking like?

Jess (00:03:48) - It's intense and it's fun, but I rope in with a team, so I literally meet with the team in all day sessions and we break the company apart and find out everything that we kind of do have. And then we put and then identify where our gaps are of what we don't have. And then we put together a customized approach. So I meet the client where they're at, and what I've done is gone out and grabbed. I believe that success leaves clues. Those on top of the mountain didn't fall there. So let's go figure out best business practices that really, really work. And then I go study that and I bring it back and say, man, if I had only known this when I was running my company or I actually did this and it was really, really great, I bring it back to the leadership team and we customize that individualized program for the organization.

Jess (00:04:38) - So after we've spent a couple of days together, kind of architecting that we then set out on the journey and I come back and run quarterly sessions with my leadership teams and in all day sessions where we are never taking our eye off the annual plan, we're constantly looking at what our three-year plan is. But my job is to kind of hold the guardrails up for the leadership team in accountability and just driving forward like what's moving the needle? What aren't we looking for? What hairy, squiggly things under the rock that we need to plop on the table and talk about? It's my job help the team scale. And that's what we do. We produce results.

Josh (00:05:20) - Yeah. What are some of the things that you've observed maybe just on the front end or during the process where you could tell the leaders are a little bit uncomfortable? Like what are some of those points where like, you know, they know they're doing the important work, but they're like, Oh, is there anything that you've observed?

Jess (00:05:38) - Oh, yeah, right.

Jess (00:05:39) - First one is apprehension. And that's just, you know, that apprehension just it's not even because of a lack of confidence, right? Because that confidence is instilled in us as visionaries. But it is a lack of confidence when we don't have that leadership team backing us, saying, hey, yeah, we can do that. We can achieve it, right? So that comes number one is lack of leadership team builds apprehension to is what are you shooting for? Like what's your target? Do you have your vision really, really, really crystallized because a lot of times those visionaries don't and it's okay, right? But until you get that vision crystallized, nobody knows what to chase. That North Star is just kind of gone and you've got people going left. You got people going. Right? And you've just got dysfunction. So that also leads to apprehension and lack of confidence and so it's just about kind of bringing everything together and understanding the visionaries, true vision of the organization and then structuring that in a very structured journey that leads to execution every single time.

Josh (00:06:43) - Yeah.

Jess (00:06:44) - Less repeatability.

Josh (00:06:45) - Yeah. And just we didn't really go too much into your background, but do you mind sharing a little bit about your success because you had a very successful exit.

Jess (00:06:54) - I did. and what happened and where I came from and what happened and what should have happened are two different things. But I'm from a ranching background. Family still runs and operates the ranch today. I grew up in rugged mountains, and I was raised by a marine Corps dad, and I left the ranch at 18 and went on my way through college, ended up graduating college and ended up starting a medical billing company out of my house. I knew nothing of health care. I mean, everything in my world is deeply rooted in agriculture. And I started a medical billing company out of my house and like I said, knew nothing but what I did figure out that I was really good at solving problems. So I started this with the intent of just really kind of making money and raising kids at home.

Jess (00:07:41) - And. Josh It just grew in massive popularity. Hockey stick growth. It wasn't pretty. It was as unsexy as unsexy can be. And it was just disastrous at times. But what we had put together was a structure, an architecture of foundation for these physicians to bring in transparency and cohesiveness in a very disparate world. And what that did is it was a massive differentiator for me, didn't realize it at the time, but as I soon moved out of my house and into my first office and then that office into a national expansion into Denver and then from Denver, internationally, you know, what I realized is those problems that we were solving were real and we were putting ourselves in a very opportunistic position or what I call a blue ocean. And so we were able to host practice management software and EMR when the electronic medical record came out and it just hockey stick growth does. And so after, you know, 11 years of hitting my head and literally about dying 20 times of just doing things wrong, I actually had somebody like me walk into my life and change my life.

Jess (00:09:00) - And it was really just a reflection time for me to, you know, he kind of held up a mirror and said, Here's what you're like as a leader. And so I, Josh, I kind of just basically got my shit together as a leader. And I started running this organization in this structured type journey that I do today. And so the next four years were bliss. Like I said, more money professionally and personally than I ever had. And so when my largest client approached me and said they want to buy me, I was like, I'm not ready. And so when the third letter of intent came in for a multiple over 20 x, I just said, Hey, yeah, got to go. And 60 days later we had an acquisition.

Josh (00:09:43) - That's a really good multiple by the way.

Jess (00:09:48) - Yes. And so this hospital system was, was backed by Apollo and my company is the revenue cycle management engine I guess for life point health today and still is.

Jess (00:10:04) - So I'm very proud I'm very honored with what happened. But I'll tell you what, had I not met somebody like me, I don't think I would have had kind of that success story because it was just clunky until then. And so anyway, I sold we moved to Texas, I bought a beautiful ranch here. I bring my execs out here to my to the ranch. And I realized not having something to do as a serial entrepreneur was incredibly dangerous. And so I kind of got talked back into going into coaching. And so I did. I started studying the art of business. You know, a lot of visionaries and leaders just don't have that time and shouldn't, right? It's just it's almost sometimes impossible. And so I started studying it for the first time in my life, and I was like, oh my gosh, man, had I just known? Had I just known, had I just known? And so I did. I started my program. It's called Advance It and how to advance and scale an organization.

Jess (00:10:59) - So it came back as a strategic business guide and work with leadership teams best and most fulfilling thing I've ever done in my life.

Josh (00:11:05) - Yeah. And what's your vision for the future of this operation now?

Jess (00:11:11) - So great question. I work with a very limited amount of clients in what I call the full service or the climb, and that's where I work with leadership teams because I really rope in with them. So that's a very exclusive bunch of clients. And then I started what I call masterminds, and that allows me to kind of be able to work with the ascending leader. Josh That's not necessarily on one of my leadership teams because I just still have a passion for really helping people get through some of their leadership roadblocks at headwinds. So my mastermind programs are two hours a month on Zoom with me where I lead content and you're with other ascending leaders all over the United States. And then we're working on building some courses. We're kind of just wrestling with that right now as to what that looks like, but doing some self-paced courses that some of my leaders might be able to take.

Jess (00:12:04) - So my vision for this is to be around for the long run and really work with clients that want to grow and achieve. And what's fulfilling to me. I mean, if you want to scale and you want to take your company to that next ten X level, I'm your huckleberry for it. And it's just it's the best thing I've ever done. So I plan on living in this space here for a long time.

Josh (00:12:29) - Sure. Your website is Jess dash Stewart Com What would you recommend someone do now that they've heard our conversation? What's next for them?

Jess (00:12:38) - Yeah so under the contact link or accept invitation there's you know I truly believe what I do as an invitation to change your life. And so contact us for inside of there there's a contact form and there's a dropdown menu of what you might be interested in. But reach out to my operations, admin faith and I and let us know how we can help and we'll be in touch with you. So that's the best way.

Jess (00:13:03) - There's also a link tree on there that has all my social media and LinkedIn where you can find a bunch of information on me too.

Josh (00:13:09) - Yeah, your website again, Jess Stewart dash dot com and Jess Stewart. It's been a pleasure having you on the program. Congratulations on the exit. Congratulations on the great work that you're doing today.

Jess (00:13:21) - Thank you, Josh Glad to be here.

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