Navigating Growth: Lessons from SkyQuest on People, Pilots, and Planes with Corey Head

In this episode of Struggles, host Chris Inman sits down with Corey Head, founder of SkyQuest, to discuss the journey of turning a passion for aviation into a thriving business. Corey shares how his unique approach to customer service in corporate aviation sets SkyQuest apart from traditional airlines, focusing on delivering memorable, efficient, and flexible travel experiences for clients. He opens up about the challenges of scaling the business, especially when it comes to hiring and managing a diverse team—from pilots to mechanics to dispatchers.

Corey reveals the lessons he’s learned along the way, including the importance of workplace culture, empowering employees, and creating a “triple win” for clients, team members, and aircraft owners. Hear inspiring stories, like how a passionate busboy from Corey’s favorite restaurant grew into a key member of the SkyQuest team, and insights into Corey's leadership philosophy, hands-on management style, and vision for the future of the company.

Join us for a candid exploration of the ups and downs of entrepreneurship, the value of investing in people, and the ongoing journey of building a business that puts both clients and employees first.

Chapters

• 0:00 Challenges of Hiring and Management
• 6:46 Defining SkyQuest Core Values
• 7:55 Expanding Aircraft Management Services

Transcript

0:00

We have a mechanic that works for us now that I pulled out of a restaurant that was a busboy. But he was so incredible at one of my favorite restaurants at bussing tables, and so passionate about it. I just said, hey, you should come clean airplanes. He's like, wait, what? I can work on airplanes. Welcome to another episode of Struggles, presented by ncbi, the podcast where we navigate challenges together. Hey, everyone. Welcome to another episode of ncbi. I'm Chris Inman with Idea Cleveland, and. Joining me today is Corey Hudd from SkyQuest. All right, Corey, you have a very unique business, Skyquest. You help take corporate clients and all these people around to little local regional airports and business meetings and get you home to have dinner. And as a unique business model, how did you come up with it? Well, you know, I am a pilot, so I guess I started to see it firsthand. I was the person in the front that just got the task, go from A to B, wait two days and come back, or maybe just drop these people off at their house in Naples and. And sit around for a couple of days or airline home, whatever the task was. But, yeah, I mean, I started to really fall in love, you know, with both the customer service side and the business side of this, versus just being the pilot, you know, So I really would go the extra mile on my own to just kind of like, make the flight a little bit better. Whether that was providing catering that wasn't required, or if it was somebody's birthday, we would put a couple balloons in the plane or throw confetti on the floor, things like that. Just really trying to spruce it up for next level. So it was really something. It was an experience for the client and something that they would remember and something that they would potentially tell their friends or their business colleagues about and really help us grow the business. And you're actually selling these experiences, whereas the rest of us, the fly commercial, it's just getting. It's a different experience, not it. Yeah, it's not an experience. It's a cattle call to get us to our location. Right, Right. Yeah. So, yeah, there's a big difference. Right. A lot of times when we go sell something like, well, geez, I can fly on the airlines for 400 a ticket. And I'm like, okay, well, you know, we don't necessarily compete with the airlines. You know, if you. If you try it once, I think you'd agree with us, you know, so, yeah, I mean, there's. It's different. I mean, in a bunch of different ways. Right. The safety, security, the time, the efficiency. Right. That's what we're providing to these people as a way to extend your vacation or your meeting if you need to. You can come home early if you need to. We'll have people that are on vacation somewhere and supposed to pour the whole next day, and they're just like, well, it's nice back at home. Can we just go home a day early? We're like, sure, leave whatever the heck you want. So it gives a whole new level of efficiency and time to the. To the overall experience. That's what we enjoy doing. And then when you started off with Skyquest, you basically created yourself a job like some of us do as business owners. How was it to take that next level and start hiring pilots to come on board with you? Yeah, very, very difficult. Probably hiring the pilots, I think, was one of the easier aspects, because I could maybe judge, you know, a pilot, but when it came to hiring the right mechanics, I'm like, geez, what makes somebody a great mechanic? Or hiring the right dispatcher, scheduler or whatever and keeping them engaged and what makes them great? Yeah, that, you know, if I had to say the, you know, the learning on the job, you know, you know, there was just a lot of treat people the way I want to be treated. There was a lot of common sense, at least in my opinion, that went into just growing this company. And it's funny, because you become a pilot, because I don't really want to sit at a desk or in a cubicle all day, and now I find myself sitting at a desk all day, you know. But what's become rewarding to me is I'm still a pilot. I love doing that. But what I really love now is watching other people succeed, providing them with the opportunity, whether it's one of my managers, one of my pilots, a new hire. I mean, we have some incredible stories. We have a mechanic that works for us now that I pulled out of a restaurant that was a busboy. But he was so incredible at one of my favorite restaurants at busing tables, and so passionate about it. I just said, hey, you should come clean airplanes. He's like, wait, what? I could work on airplanes. And I go, yeah, you want to? You want to come clean airplanes? He's like, this is amazing. So he started cleaning airplanes for a couple of years for me, and he's hanging out with the mechanics down there every day. He had a passion for working on cars with his dad and stuff. And I said, I'm paying. I'm going to pay for your schooling. So completely changing this person's life. And that's the stuff that's just amazing to me now and really brings me a lot of joy. That is great. And did you ever go through any kind of training to actually, like, manage people? Like, that's a whole skill set. It is. It is not anything formally. I mean, we've gone to several different one and two day seminars. You know, we attend, you know, some different business leadership events and things like that, but for the most part, again, you know, treating people the way I wanted to be treated, you know, and a lot of trial and error. I'm not here to tell you that I got it right. Every time there was any business owner said they got it right the first. Time, they're lying to you. No, totally. Yeah, there was a lot of stuff, but those are the lessons. Sometimes you gotta buy them. Right? The bot lessons versus, you know, there's. And that's what we tell people still today. There's stuff that we do well and then there's stuff that we learn from. Right. I mean, if it didn't go well, we learned something. BOM Image appreciates the opportunity to sponsor this podcast. BOM Image provides brand firepower, precision targeted brand messaging and visual identities, empowering small teams in the professional services space to attract their most rewarding and profitable customers. We work hand in hand with our client partners implementing our unique set of processes, focusing on listening, raw objectivity, and accountability to help them present a more impactful brand story. Our passion is inspiring clients to create their bomb image. What was the one thing that you wish you'd known when you started the company where you are now? Gosh, that's a great idea. A good question. I think probably how important culture is to me. I was one of those people that just. You gave me a task. I worked hard. I didn't really worry about all that little extracurricular stuff. I mean, you're working hard and you made yourself a business, so you didn't really think about these things. No. But how important that is and to keep everybody engaged and really learning that it's not money that keeps these people loyal to you or keeps you around every day or whatever. It's. It's driving toward a common goal. It's being aligned. It's basically, it's, you know, it's really being part of a great culture where, yeah, if I work hard, I'm actually happy because I'm helping these other 100 people that work for this company. Like, that's somehow the mentality that you have to Hire for that you have to evaluate against and that you basically have to hold your. Yourself accountable to. And, you know, and I think doing that, it took us years and years and years to realize, you know, what's important, what are our core values? You know, we've gone through a lot of these amazing exercises to kind of reverse engineer, you know, what makes somebody an amazing SkyQuest employee. And we're not talking about pilots. We're talking about the guys that clean the planes, the dispatchers, the. The mechanics, whoever, you know, how come if you say, you know, who's an amazing employee and this person comes to mind, why, you know, and then really using those traits, and we call them traits, and we have basically our core values are mirrored after those and then hiring, you know, establishing, you know, these are the people we want to be with, you know, like number one in traits. And the T is teamwork. I want to be around people that want to be part of the team. If you're not helping our team, then quite frankly, you know, we don't need you on the team. You know, and it's. And it's difficult sometimes, and I really totally underestimated that in the beginning. But it's. It's something that we've, I think, done a great job with now. It's taken us 20 years, but it's. We have just an incredible group of people, and that's how we continue to have success. So you're obviously working on the business. What's something you're working on currently for the future, SkyQuest? Yeah, well, right now, you know, we're focusing on, you know, building the aircraft management side. So that's not even necessarily people that just charter the airplanes two, three, ten times a year or whatever, but people that have the need to own an entire airplane, you know, for whatever reason, you know, maybe they want to control that asset or I want to know that this is an airplane that I know everything about, or I want to know the crew every time that's going to be on it, whatever their reason for owning it, you know, so that's what's really helping us sort of grow in the future. And, you know, a lot of what we do now and, you know, is. Is really just trying to negotiate, you know, stuff down and economies of scale. And, you know, we buy a lot of parts and sell a lot of gas and things like that, and it's really making sure that, you know, the stuff can be efficient. And if it's not efficient for the aircraft owner, then they're probably going to go away eventually, you know, and creating job security for all of us is making sure that it's a win for everybody. You know, we kind of call it the triple win. It's got to be a win for the aircraft owners. It still has to be a win for the charter clients. It's got to be a win for our team, for our employees. You know, if you grind somebody out too much, it's going to affect the other aspects of it. What's the future hold for you? Well, I'm very happy. I mean, I got to say, it's been hard work, but, you know, for me now, I really love being a pilot. I can really pick and choose my schedule instead of somebody telling me where to go for the next three, four, five days. So that's. That's been fun. I want to continue to make good decisions, you know? You know, for this company and help it succeed for sure. And I want to continue to empower the incredibly capable people that work for me. Whether you're a pilot or a mechanic or dispatcher, whatever, these are the job that needs to be done. You know, go do it. Do it better than I ever did. You know, do it better than the person that hired you. And really, let's make this thing more successful tomorrow than it was today. That's my goal. Well, this has been a lot of fun. Thank you so much for coming in. You're welcome, Chris. Thank you. And thank you all for listening. And please tune in to the next episode of Struggles presented by ncbi. Thanks for tuning in to this episode of Struggles presented by ncbi, where we navigate challenges together. Don't forget to subscribe, listen and share this podcast with others who might benefit. We'd love to hear about the struggles you're facing or have overcome, and we'd be thrilled to have you as a guest on a future episode. Let's get continue this journey together.