How to Succeed as an Outsider in Your Industry with Rich Thomson

16 Jun 2025 · 22 min

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Entrepreneurs on Fire Podcast Episode Summary

Episode Details

  • Podcast Title: Entrepreneurs on Fire
  • Episode Title: How to Succeed as an Outsider in Your Industry with Rich Thomson
  • Host: John Lee Dumas (JLD)
  • Guest: Rich Thomson, Founder and CEO of Dreamliner Luxury Coaches
  • Release Date: [Insert Release Date Here]

Episode Overview In this episode, JLD engages with Rich Thomson, who transformed Dreamliner Luxury Coaches from a small fleet of 12 buses into the nation’s largest entertainment logistics company, serving high-profile artists like Taylor Swift and Beyoncé. The discussion focuses on the unique advantages of being an outsider in the industry, the significance of team dynamics, and strategies for growth and innovation.

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Key Concepts Discussed

  1. The Advantage of Being an Outsider
  2. Perspective Shift: Rich emphasizes that not being entrenched in the traditional methods of the industry can provide fresh insights and opportunities.
  3. Personal Experience: Before entering the transportation business, Rich had significant experience in finance, which allowed him to view the logistics sector differently.
  1. Building Relationships
  2. Importance of Trust: Rich stresses the need to build relationships with key stakeholders and leaders within the industry.
  3. Acquisition Strategy: He shares insights on acquiring legacy truck companies, highlighting the value of rapport with founders.
  1. The Significance of Team Dynamics
  2. Right People, Right Places: Having the right team in place is crucial for success; Rich focuses on identifying leaders within his organization to ensure effective operations.
  3. Employee Well-being: Rich discusses the importance of treating employees fairly and ensuring they feel valued, as they spend a significant portion of their lives at work.
  1. Seizing Opportunities
  2. Jumping on Opportunities: The narrative emphasizes the importance of recognizing and acting on opportunities, particularly during pivotal moments like the COVID-19 pandemic.
  3. Innovation and Growth Plans: Rich envisions expanding Dreamliner’s market beyond just music to areas such as corporate events and sports logistics.

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Top 3 Value Bombs

  1. Build Relationships: Trust and credibility are vital for success; find the right leaders and invest in those relationships.
  2. Team Importance: Focus on having the right people in the right roles and support them in their professional and personal lives.
  3. Go All In: When pursuing entrepreneurial ventures, avoid backup plans and commit fully to your endeavors.

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Key Takeaways

  • Take Risks: Rich urges entrepreneurs to take leaps of faith and not let fear of failure hold them back.
  • Start with Relationships: Building trust is essential not only for acquisitions but also for overall business success.
  • Embrace Change: Being an outsider can lead to innovation and differentiation in a saturated market.

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Call to Action For those interested in learning more about Dreamliner Luxury Coaches or connecting with Rich Thomson, visit their [website](https://dreamlinercoaches.com) or reach out through social media channels. Additionally, listeners are encouraged to explore resources provided by the episode's sponsors, including Franocity for franchising opportunities and NetSuite for business management solutions.

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Final Thoughts This enlightening episode provides valuable insights into how outsiders can leverage their unique perspectives to succeed in established industries. Rich’s journey serves as an inspiration for entrepreneurs to embrace risks, prioritize relationships, and innovate continually.

For more episodes and insights, visit [EOFIRE](https://eofire.com) and search for "Rich" to access this episode's show notes.

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Transcript

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0:02Who's ready to rock today, Fire Nation? JLD here and welcome to Entrepreneurs on Fire, the only daily show interviewing the world's top entrepreneurs seven days a week. Today, we'll be breaking down how to succeed as an outsider in your industry. To drop these value bombs, I brought Rich Thompson into EO Fire Studios. Rich is the founder and CEO of Dreamliner Luxury Coaches, expanded from 12 buses to the nation's largest entertainment logistics company, serving A-list artists like Taylor Swift, Beyonce, Drake, and more. And today, Fire Nation, we're going to talk about evolving. We'll talk about how being an outsider is actually an advantage.

0:36Having the right team is key. How do you do that? And oh, so much more. And a big thank you for sponsoring today's episode goes to Rich and our sponsors. Franocity has helped hundreds of people leave unfulfilling jobs, invest in recession-resilient businesses, and create legacy income for their families through franchising. Visit franocity.com, that's F-R-A-N-O-C-I-T-Y.com to book a free consultation and start your franchising journey with expert guidance. These days, your business needs total visibility from global shipments to tariff impacts to real-time cashflow. That's NetSuite by Oracle, your AI-powered business management suite trusted by over 41 ,000 businesses.

1:15Download the free ebook, Navigating Global Trade, Three Insights for Leaders at netsuite.com slash fire. Rich, say what's up to Fire Nation and share something that you believe about becoming successful that most people disagree with. First, what's up, Fire Nation? You know, I think it's the backup plan. People always, people want to have a backup plan when they're going to go take a big risk. And I was told from a guy I trust and stay close to that don't have a backup plan. If you're going to take the leap and you're going to go give something a shot, don't have a backup plan. If you have a backup plan, you'll always be willing to fail.

1:53So don't be willing to fail. Don't have a backup plan. Go all in and just find a way to make it work. So listen, in the introduction, we talked a little bit about your company, Dreamliner. And my audience knows for a fact that if you're going to be a successful entrepreneur, you need to become the number one solution to a real problem in a growing industry. How did you do that with Dreamliner? Well, listen, I was very fortunate to, you know, to start with 12 newer coaches. Not many people can jump into this industry and have 12 nice new built coaches. And so when I saw opportunity during COVID to acquire these coaches, I think, I took the leap and gave it a shot.

2:34And from there, it's been a focus since then of being kind of the nicest, newest, high-quality fleet. And although it started with a small, let's just be small and be the nicest, newest fleet, and these small opportunities have continued to arise that were things you can't say no to. You've got to jump on opportunities and seize the moment when it's there. What was one of those inflection points? What was one of those opportunities that really took you from just these 12 coaches to what now is the nation's largest entertainment logistics company in America? Relationships and relationships been how, I mean, my whole life, that's kind of how, you know, how I've gotten where I'm at today is relationships.

3:22But for Dreamliner specifically, you know, I had spent a lot of time with Kylie, Kylie Irvin, who was the founder of Diamond Coaches, you know, 20 year founder, built a great business reputation and had relationships across the industry. And so I, you know, leveraged her a lot, starting the business and spent a lot of time with her. And when she decided it was time for her, she said, you know, just, I think it's just time for me to move on. Um, and she said, why don't you just, why don't you buy me? We had kind of teased about it for a while, but she said, why don't you buy me? And I said, let's do it.

3:53Let's make it happen. And so, um, you know, uh, that's when the game really changed because we went from 12 coaches and we had, you know, we were opportunistically buying a bunch from Prevost. Um, but we are at the time probably, you know, 22, 23 coaches. And so all of a sudden by a a real player in the space and have a headquarter facility in Nashville and all of a sudden become 60 plus coaches and become a top, you know, three, four, top five for sure. Bus company was, oh, wow, this is, this is not a cool side hustle anymore or a nice little boutique business. We're a real player. Um, so that was the real, that was the real game changer for me when I also had to look at my, myself in the mirror and look at my wife in the eyes and say, we got to move where The Manhattan Beach in California is awesome, but this business is more awesome and we need to go get closer to this and be more involved.

4:46Now, was there a moment? I mean, you've served Taylor Swift, Beyonce, Drake. Was there a moment when something happened as you were growing that just really amplified that growth, that just really sped that success up? Was there one story that you can share with us? I think the continued focus on it being this business being a real business, a real product and a real service has been what's really, I think, differentiated us from some of the other companies and the other leasing companies out there. if you think about this business as not just hey you go lease a bus and you you know you hire a driver and you lease a bus which is the way the industry was for a lot of years and you look at and say actually no i'm actually creating like this whether you want to look at as a private jet or a four seasons you could say hey this is actually like a you know a fancy hotel room a house on wheels and it's got to be high quality from the products in it to the cabinets to everything, that high end experience is what these guys want.

5:48And they want to know that it's, it's a, it's a newer bus, it's maintained mechanically, you know, they want to know that it's being serviced. The driver's professional and the driver has experience doing what they do, and they're going to stay out of their way and just be a driver and not try to get involved. So I think just the real, the real differentiation has been thinking about this as a true business. And I don't think that it's not a knock to anybody, but the industry has kind of evolved over the years. And a lot of times most, some companies still do this where your driver's not even an employee of the company.

6:20Um, they just hire a driver and someone lets the, the, you know, the coach go out there. Um, so that's not how I want to run the business. And I don't think that's how the, the, the big tours. And, uh, if I'm an artist, I want to have a company that's, you know, that's doing things by the book and has the right insurance levels and, you know, does things from a regulatory standpoint, make sure the drivers have enough rest, have enough experience and are doing things they need to be doing. So sometimes jumping into an industry as an outsider can be an advantage. How is this the case for you? I do think it was an advantage because a prior to this, I, you know, I was starting and building my own private credit fund and I've been working with founder entrepreneurs my whole career on the finance side.

7:05So I got to hear stories and underwrite and invest in a lend money to a lot of different founder entrepreneurs and how they They built their businesses, what they did good, what they did bad. And I'm no smarter than any one of them. But when you see that much, you know, that many different types of stories, situations, you do learn things that worked and things that need to be done. People that didn't want to do it a certain way. So I think it gave me a fresh perspective on maybe how this, a certain business diamond coach specifically, or hemp pill before we bought that one. And just kind of building a business on things that are important, you know, from customer service to infrastructure, to making sure your finance accounting team's there, making sure that, you know, your employees have, you know, healthcare benefits and that they're happy and they have the things they need.

7:48So I think that brought a fresh perspective to me coming into the industry as not a bus guy, but a business guy that says, I understand, I can learn this business and I've learned the business pretty well now, but that fresh perspective, I think really, really is, you know, something that, although there's probably a little bit of, you know, reaction from the industry saying, well, who is this guy? Like he's getting all large corporate on us. They're getting too big. I'm still just the same guy that owns a bus company, right? You know, we're just trying to build a business. We want to have, want to provide a product and provide a service to our clients.

8:21Fire Nation, we have so much more to talk about around this topic. When we get back from thinking our sponsors, starting your own business can feel intimidating. Where do you start? How do you grow? When will you start generating revenue? All valid questions. If you love the idea of creating wealth and freedom, but you're not sure if starting from scratch is the way to go, then I'm excited to tell you about Franocity. Franocity has helped hundreds of people leave unfulfilling jobs, invest in recession-resilient businesses, and create legacy income for their families through franchising. Their clients come from all walks of life, executive veterans, first-time buyers, and multi-unit investors, and their mission is simple, to remove the guesswork, reduce the risk, and help everyday people become business owners through franchising.

9:01Don't know anything about franchising? That's the beauty of it. Franocity provides personalized one-on-one coaching at no cost to you, and they have access to over 600 franchise brands. And Franocity doesn't just help you pick a franchise, they help you understand the business model, investment risk, scalability, and operational reality. Ready to explore business ownership through franchising? Visit Franocity.com, that's F-R-A-N-O-C-I-T-Y.com to book a free consultation and start your journey with expert guidance. I think we can all agree that it's an interesting time for business. Tariff and trade policies are shifting.

9:33which affects supply chains, cashflow, and more. And if your business can't adapt in real time, that's a big concern. You need total visibility from global shipments to tariff impacts to real-time cashflow. And for that, there's NetSuite by Oracle, your AI-powered business management suite trusted by over 41 ,000 businesses. NetSuite is the number one cloud ERP bringing accounting, financial management, inventory, and HR into one suite, giving you one source of truth and the visibility and control to make quick decisions with real-time forecasting, you're peering into the future, allowing you to know what's stuck, what it's costing you, and how to pivot fast.

10:06And with AI tools, you can automate everyday tasks, allowing your teams to stay strategic. If our business needed this type of software, I'd use NetSuite in a heartbeat. It's one system, full control, tame the chaos with NetSuite. If your revenues are at least in the seven figures, download the free ebook, Navigating Global Trade, three insights for leaders at netsuite.com slash fire. That's netsuite.com slash fire. Summer is here, and that means beach trips, vacations, and summer camps are here too. And with these activities come seasonal jobs, everything from camp instructors to tour guides and more.

10:38This means that people with these specific skills are on high demand and not easy to find. Whether you're hiring for one of these roles or any other role, how do you find top talent before the competition gets them? Zip Recruiter. And right now you can try Zip Recruiter for free at ziprecruiter.com slash fire. How does it work? First, Zip Recruiter's powerful matching technology immediately goes to work, identifying top talent for your roles. Then once you see a candidate who really shines, you can use ZipRecruiter's pre-written invite to apply message to personally connect with your favorite candidates.

11:09Gear up for summer with ZipRecruiter's high-speed hiring tools. See why four out of five employers who post on ZipRecruiter get a quality candidate within the first day. Just go to this exclusive web address right now to try ZipRecruiter for free. ZipRecruiter.com slash fire. Again, that's ZipRecruiter.com slash fire. ZipRecruiter, the smartest way to hire. Rich, we're back and having the right team is so key. So talk about the strategies that you employed with your team to keep everybody happy and just the team fully functioning in the way that you knew needed to happen. Team's important. And this is where my lack of experience has been a lot of adjustments for me.

11:52Because in the finance world, you deal with a very different type of education, experienced people that you work with and that I employ there. And so here you have a lot of different people with different skill sets. You've got, you know, you've got a guy that, a carpenter that works in there, an electrician, a plumber. You have all sorts of guys that are working in the build shop manufacturing these buses. You have, you know, interior guys that are just doing typical repairs, day-to-day repairs. You have housekeeping, you know, you have grease mechanics, you have body paint. So you have a lot of different types of employees, right?

12:25So very important that you have the right people in the right places, which has been the biggest focus of mine, especially since acquiring hemp pill and kind of, you know, doubling, tripling in size. So how do you find the right people? I think you find, you find the right leader in, in each group or find the right kind of key guy in each group department and you build that trust. And so, you know, you build the trust with them and then you rely on them and you put, you know, and trust them to help find the other right people and make sure you have the right people on board. And those people might be the right people.

12:59They might be great at the job, but they may not believe in me or they may not believe in kind of our mission and what we're trying to do as Dreamliner. And you're either, you know, you're either on the team and you're all in for Dreamliner and you want to be part of that team or you're not. And if you're not, you should go somewhere else and that's okay. Like I hate losing employees or people leaving, but if you don't want to, if you don't really want to be here, then I'd rather you not be here. Like, don't come here and be miserable. That's not great. So find people that like their job, that love their job, and that want to be there for a reason, and that respect you and respect what you're trying to build, and treat them fair.

13:33Treat them like people, right? I mean, again, I don't care. It doesn't matter what group you're in. Like, I can walk around our facility, any one of them, and walk, you know, walk, talk to each one of them, no matter what role, how low, how high you are up in the company. Say hi, how you doing, what's happening, learn about things that are happening. You know, we've got guys in our office that have had cancer, you know, and so what can we do to help them? What can we do to be there for them or their family or help them while they're going through radiation or what things like that are happening?

13:59You know, you can do like, how do we build a team? How do you build the reputation with the group? You support those people. You do anything and everything you can to make people feel like you understand that although this is a job and they have a job to do, like it's their life. They spend their life working. We all spend more time working in our life than we do doing other stuff. So make sure that you're, you know, they feel like they have good support. They have, they're getting paid fairly. They have good healthcare. They have good benefits, you know, and that there's real opportunity for them if they want to do more to do more.

14:29And if they don't, then you support, you know, them doing their job day to day. So many of my listeners, Rich, they're looking to acquire other businesses, but in those scenarios, a lot of times those other businesses are resistant to being acquired for any number of reasons. And as we've talked about already, you decided to acquire legacy trucking companies into Dreamliner, but you were very successful doing this. How did you get them to say yes? Spending a lot of time with these guys, you don't go out and say, hey, I'm going to buy you and I want to buy you and talk valuation. I think you've got to go back to relationships.

15:04You've got to build credibility. You've got to build trust. You got to look a guy in the eye and spend a lot of time, whether it's, whether it's talking on the phone, whether it's meetings in person, dinners, drinks, whatever it is, spend a lot of time and you got to build trust and build a real relationship with the founders. You know, I wouldn't have bought either one of these trucking companies without the founders of those companies staying on board and becoming a part of it. I recognize that no matter how much I think I could take their business and maybe we can build it and do more, like I can't do any of it without them.

15:33So I think, I think the answer to your question, I'd say recognize that, you know, you need those people, those people that built it, no matter what you think you can do, no matter how much more you think you can do with it, or how smart you are as a person trying to make an acquisition, recognize those people built something from scratch. They got it where they got it and lean on them, build them, build, get, gain trust from them. And then if you have their trust, then everyone that they bring over that works for them, they're going to fall in line at some level, maybe not all of them, but majority of them are going to say, if I've been working, you know, for Mike or for Curtis for 10 years, I trust him with everything.

16:13And I want to stay working with him. If Curtis says, you know, is a great guy. I trust him. He's going to take care of me. He's done everything he's ever said he would do. He's going to live up to his word. Him and his team and the rest of the team there and the other people that they talk to, they're going to say, I want to work for Rich and I will work for Rich. And so it's going to make that that much easier for someone to say, you know what, this is a good guy that could take over my company that I could trust with these employees and the families that work for me. Now, DreamLeners had a lot of success, but you know the kind of person that's just going to sit on your laurels and just kind of watch it drift off into the sunset.

16:49What's next for Dreamliner when it comes to innovation, when it comes to growth? Right now it's well-oiled machine, right? It is, let's make sure that 210 plus buses, 70 trucks, 220 trailers, let's make sure those are well-oiled machine and that everything we do with our clients is just perfect. Let's just get it going that way. I think there are a lot of opportunities outside of music that we're going to start tapping into. So I would say think of things like a NASCAR, think of the PGA, think of the NBA, you know, other other racing sports teams, think corporate events. I think there's a lot of that out there.

17:31People just don't know that if you look at what we do in the music side and because of the shortage and lack of supply in this industry, everyone, every coach goes to music. but if you could actually start building and focusing a little more on, you know, something between a music star, you know, a star coach that we do at a marathon, um, think of how many families would be like, I would love to take that coach for, you know, a week or two week trip, um, hire a driver and do that. There's a lot of people that can afford that, but don't even, don't even know it exists. So I think there's a lot of opportunity there to do that.

18:00And if you think about relationships with, with a NASCAR, with a Indy car, with a PGA, things like that, I think we can start diversifying into there. so diversification would be great and I think it opens the doors to a more of the consumer channel which would be I think great because I think most people look at the world and say I either have to spend three million dollars on a really fancy marathon which I don't want to do and even the people that can afford them they do it and they realize why did I do that you know I just sits around you need someone to manage it so if you find out that someone like a dreamliner could could lease you one of those, um, or build you one and lease it to you for a month for a 12 month lease, you know, a month, 12 months, three years, five years, and manage all aspects of it for you and make sure you have a driver and that the thing's set up everywhere, everywhere, anytime you want it.

18:53You know, I've been teasing lately. I, I'd like to see us be the net jets of buses when you need it, where you need it. You know exactly what you're going to get. You want your catering. You want this, you want that professional, professional pilots, drivers. That's where I see us going. That's a great vision. And Fire Nation, you can see that Rich has a plan to get there. Rich, if you could just share one key takeaway from our conversation today. We talked about a lot of great stuff. What would you want our listeners to walk away with, that one takeaway? People ask me all the time. They say, what is one thing you wish you would have done or you wish you would have done or wouldn't have done?

19:33And I wish I would have started earlier. there. I wish I would have taken the leap sooner. You know, the opportunity may not have been there, but what I'd say to anyone out there is, is go for it. You know, you, you're never going to, you're never going to get it if you don't take the leap. Right. And as scary as it might be, and as tough as it might be, whether you're, you know, you don't have enough cash saved up, whether you've got, you know, you're, I mean, I have my third kid on the way, um, when I jumped out. So it doesn't matter where you're at in the stage. Like you should, I think you should, you got to go for it, right?

20:02This is a life short. And I don't think you ever want to look back and be like, oh, that's great. I got a bunch of money in the bank. Or you want to look back and be like, I'm glad I took that risk. That was really cool. That was a fun experience. Rich, if Fire Nation wants to connect with you, wants to learn more about Dreamliner, what is your call to action for our listeners today? Hit our Instagram, LinkedIn, our website. I am always available to anyone that wants to chat. So feel free to reach out via those channels anytime. Fire Nation, you're the average of the five people you spend the most time with.

20:31You've hanging out with RT and JLD today. So keep up the heat. For links to everything we talked about, visit eofire.com. Type Rich in the search bar and the show notes page will pop right up. And Rich, thank you for sharing your truth, your knowledge, your value with Fire Nation. For that, we salute you and we'll catch you on the flip side. Thanks a lot, JD. Appreciate it. Hey, Fire Nation, a huge thank you to our sponsors and Rich for sponsoring today's episode. And Fire Nation, over the last decade, I've interviewed more than 4 ,000 of the world's most successful entrepreneurs, and I've created a revolutionary 17-step roadmap to your financial freedom and fulfillment.

21:06I put it all into my first traditionally published book, The Common Path to Uncommon Success, personally endorsed by Seth Godin and Gary Vaynerchuk. The Common Path to Uncommon Success is the step-by-step guidance that you need to achieve the lifestyle of your dreams. Visit uncommonsuccessbook.com. I'll catch you there or on the flip side. Franocity has helped hundreds of people leave unfulfilling jobs, invest in recession-resilient businesses, and create legacy income for their families through franchising. Visit Franocity.com, that's F-R-A-N-O-C-I-T-Y.com to book a free consultation and start your franchising journey with expert guidance.

21:46These days, your business needs total visibility from global shipments to tariff impacts to real-time cash flow. That's NetSuite by Oracle, your AI-powered business management suite trusted by over 41 ,000 businesses. Download the free ebook, Navigating Global Trade, Three Insights for Leaders at netsuite.com slash fire.

From the publisher

Rich Thomson, Founder and CEO of Dreamliner Luxury Coaches, expanded from 12 buses to the nation's largest entertainment logistics company, serving A-list artists like Taylor Swift, Beyonce, Drake, and more.

Top 3 Value Bombs

1. You can find the right people by finding the right leader in each group and build trust with them.

2. Team is important so focus on having the right people in the right places.

3. Recognize that you need to build relationships, credibility and trust with the founders and no matter how much you can do with the business you need to lean on the and gain trust from them.

Bringing A Personal and Customized Approach to every project - Dreamliner Luxury Coaches Website

Sponsors

Franocity - Franocity has helped hundreds of people leave unfulfilling jobs and invest in recession-resilient businesses through franchising. Visit Franocity.com to book a free consultation and start your franchising journey with expert guidance.

ZipRecruiter - See why 4 out of 5 employers who post on ZipRecruiter get a quality candidate within the first day. Just go to this exclusive web address to try ZipRecruiter for free. ZipRecruiter.com/fire.

NetSuite - NetSuite, by Oracle, is your AI powered business management suite, trusted by over 41,000 businesses. Download the free e-book, Navigating Global Trade - 3 Insights for Leaders at NetSuite.com/fire.

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