Leonard Goldberg | Flying Private Jets, Palm Beach Billionaires, and Scaling Up a Charter Plane Company
Smart Business Revolution

Leonard Goldberg is a commercial pilot, flight instructor, and the Owner and President of Gold Aviation Services. He is an aeronautical entrepreneur who owns an aircraft charter management, maintenance, sales, and acquisition company. He also appears in various videos and programs about selling jets and has several YouTube appearances on Flying Doodles and Sailing Doodles for Bahamian hurricane relief. Leonard is also involved in philanthropy where he and his wife actively support the Gilda’s Club of South Florida. 

In this episode of the Smart Business Revolution Podcast, John Corcoran is joined by Leonard Goldberg, the Owner and President of Gold Aviation Services, to talk about growing a business in the airline charter industry. Leonard also talks about the challenges he has faced building the business, explains how he uses employee training to retain top talent, and talks about changes in charter bookings over the years. Stay tuned.

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Here’s a Glimpse of What You’ll Hear:

  • Leonard Goldberg’s background working as a dispatcher for a charter plane and how he started his own brokerage company
  • How Leonard used to network with potential customers and what he learned about growing and scaling a business to over $10 million
  • How the 2008 economic crisis affected Leonard’s business
  • Leonard explains how the Eclipse jet and financial forecasting have impacted his business
  • The business owners and associations that have helped Leonard grow — and how previous business experience helped him prepare for the COVID-19 pandemic
  • How aviation companies use training to attract and retain pilots 
  • How bookings in the charter industry have evolved over the years
  • Does Leonard still love flying?
  • The peers Leonard respects, how being on EO’s board helped his business, and how to get in touch with him

Resources Mentioned In This Episode

Sponsor: Rise25

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Episode Transcript

Intro 0:10

Welcome to the revolution, the Smart Business Revolution Podcast, where we ask today’s most successful entrepreneurs to share the tools and strategies they use to build relationships and connections to grow their revenue. Now, your host for the revolution, John Corcoran.

John Corcoran 0:40

Hey, welcome, everyone. John Corcoran here. I’m the host of this show. And you know, every week I get to talk to smart CEOs, founders and entrepreneurs of all kinds of companies. Check out the archives we’ve got interviews with the CEOs or founders of Netflix and Kinkos’ and YPO, EO, Activision Blizzard, LendingTree, OpenTable, go check them out. Lots of great episodes there lots of great wisdom to share. I’m also the Co-founder of Rise25, where we help connect b2b business owners so their ideal prospects. My guest this week is Leonard Goldberg. He is an aeronautical entrepreneur, you probably don’t hear that every day. He owns an aircraft charter management, maintenance, sales and acquisition company. He also appears in various different videos and programs including selling jets on a wealth of entertainment network and several YouTube appearances on flying and sailing doodles for Bahamian hurricane relief. He also is involved in philanthropy including his wife actively support the Gilda’s Club of South Florida. He’s also a commercial pilot and a flight instructor. And we’re going to talk about a unusual air type of business you don’t hear about very often, how do you start a business where you do charter management, maintenance, sales of planes. And so we’re going to get into in a second. 

Of course, this episode is brought to you by Rise25, where we help b2b businesses get their clients referrals and strategic partnerships with done for you podcasts and content marketing. And if you want to learn about how you can do that, go to rise25media.com and we will tell you all about it. Alright, Leonard, pleasure to have you here today. So, take me back to the very beginning. You’re young, you’re working for a charter company, and you get fired. You hear the story so often with different entrepreneurs and founders. And it’s like two roads splitting the wood in, in the woods, right? And there’s two different ways you can go with this. Well, do I go get another job? Go work for another company? Or do I start my own thing? You and starting humblest of roots, one plane with little flights over the Bahamas? Maybe that maybe I’m even getting ahead. And that wasn’t the very beginning. But take me back. What was that very beginning. Like you get fired? Like, and you decide what Alright,

Leonard Goldberg 2:38

I’m going to start my own company. Yeah, so it was interesting. I was a flight instructor. And a friend of mine was a dispatcher at a charter company in Palm Beach, Florida. And the session was, you did that dispatch position. So you can move into the fight line when a co pilot position opened up. So that was kind of the route we were gonna go on. So he went to the copilot seat and said you wanted to be a dispatcher here at this charter company. So I went up Palm Beach and did that and really fell in love with that segment of our industry, the general aviation part, flying private jets, that was a whole new world for me. The first quote I did to someone I couldn’t believe that they could afford to fly to New York on a private jet and spend almost $10,000

John Corcoran 3:25

is a dispatcher helped me with that as a dispatcher. You’d like doing sales? Are you talking to the customers that we’re doing? Okay,

Leonard Goldberg 3:32

back then you kind of did it all you did customer call, they we actually use phones back then not just the internet. They would call it’d be a personal relationship, you give a quote? If they booked the trip, they work through you to book the trip, then you would you know dispatch the trip to the crew and decide what airplanes to use what crew to use. So we’ve been pivotal to doing all that.

John Corcoran 3:54

So we learn all that land all the scenes. Yeah, it

Leonard Goldberg 3:57

was it was a lot of fun. I really enjoyed it. Like the atmosphere like everyone I worked with, and the aircraft that were we were using, and thought I’d found a home for my career. The owner bought three other facilities like that. I mean, they called fixed base operations, basically gas stations for private jets. And he bought other facilities, rebranded it and flipped it to Signature Flight Support, which is probably the biggest FBO chain in the world. But they only do the gas station functions sell gas and provide hangar space, you know, so they actually shut the HR department down, shut the maintenance department down. So I found myself virtually fired. And I had developed a lot of relationships in the two years I was there. Got some job offers and I realized if I went on my own I could produce the same amount of income, potentially having the relationships I had where I’d be a broker. So I had great low overhead start started out brokering and then going the sales of planes. No broke me on the charter. Okay, the charters got it. Okay. Yeah. So you know, and we, you know being in Palm Beach we had the wealthiest people in the world that live there and came through there. So I was doing everything from a Piper Navajo chieftain which is a twin engine piston airplane to the Bahamas. Because the Bahamas is so close to us, we did do a tremendous business there in the Caribbean, two big Gulfstream jets flying to Europe and everything in between. So I said if I could just do a few take a few of these customers that obviously now don’t have a place to call because they shut the charter department down. Um, you know, the margin would be good enough for me to survive. Yeah. So not only did we survive, but I thrived it that that brokerage business,

John Corcoran 5:51

and were you flying also? Or are you just doing the broken? Oh, yeah. So

Leonard Goldberg 5:55

I never got to the fight line. Right. So I, I was doing some flying, you know, some of these flights that they went single pilot and happened the right seat. So I continue to fly. But my primary job was was the person booking the trips? In some

John Corcoran 6:11

ways? That’s a good thing, right? Because you were literally not in the business. You’re kind of overseeing the business working on the business. Yeah, sense. I guess all the sales and things like

Leonard Goldberg 6:22

that. Yeah. If I was out flying, it’d be a lot harder to, you know, do Yeah, talk to the Crips. Right. So, when I got to start my own business in 1995, the intent was to get a managed airplane, I’d fly as the crew and I started charter certificate from scratch. That process is very arduous with FAA, but that was kind of my intent. You know, have the revenue coming in from the brokerage business, and then grow a fleet of airplanes that start with managing someone’s and going from there, and then also flying because of my love of flying. But the brokerage grew quite rapidly. We were doing a very high volume, hired a few people. And then 1997, I bought dolphin Atlantic, which was an operating charter certificate with one airplane, and I’ve never chieftain on it. So now we had the brokerage. Now we had the charter certificate and one airplane. So then we started growing the certificate, from there with more airplanes.

John Corcoran 7:19

Got it. Got it. And where does one network with other potential customers? I’m curious about that. You know, you’re a young guy, you know, you just started your you’re playing, you know, do go and join the palm, palm beach, Yacht Club Country Club, like, you know, you had some network, but you probably wanted to expand it even further. So can you remember in those early days, like how you kind of networked amongst that community?

Leonard Goldberg 7:44

Sure. So well, being at the airport itself is a big help and getting a good reputation. So people will refer you. But one of my clients was Mrs. Scripts. I usually don’t talk about clients. But obviously, this is going back a long time ago. And she did a Red Cross ball. So I would be a sponsor at the Red Cross ball. And the who’s who of Palm Beach was there, huh. So I would do some sponsorships.

John Corcoran 8:13

That’s great. Yeah. So finding the right opportunities to sponsor them. Yeah, right. Yeah. Did you auctions and auction off a flight to the Bahamas or anything like that?

Leonard Goldberg 8:22

I, you know, I couldn’t afford to do that.

John Corcoran 8:25

Too much. But since then you’ve done that? Yes, yeah. You’ve had some cool experiences, and also philanthropy with your planes, which we’ll get to in a second there. But talk a little bit about some of the early growing pains you ended up hiring, your college roommate is director of maintenance, and a couple of other people that you had relationships with, and they kind of helped to get the company off the ground in the early years. 

Leonard Goldberg 8:47

Yeah, so it’s an entrepreneur story where we’re, you know, we worked in the business, I worked 24 hours, seven days a week, I didn’t have a family or anything, you know, my life was was the business, I would be at the airport seven days a week. And I thrived on the environment. And the people that I brought in to help me had the same kind of culture. We were young, and we loved aviation, we’re passionate about it. And we just kept growing and kept working and grew the business, you know, grew that, that that goal of $10 million. And when we got there, I had met Verne Harnish, several years earlier. At that time, it was The Rockefeller Habits now it’s gazelles. And when I first joined EO in 2001, I had met him shortly after he, you know, he says at $10 million, you have to fire your management team and just hire the next level of management. I’m like, this guy doesn’t know he’s talking about these people helped me grow this business. But the reality was in 2006, when we had been doing it for a decade, you know, maybe a little less than a decade. Everyone was, you know, kind of kind of getting a little burnt because we didn’t have the management expertise to keep growing So when we got to that $10 million mark, I, you know, I, with EO and being involved in yo, I knew that we could hire the next management level to keep us growing. Take us to the next level. So we could all make more money and actually work smarter, not harder. But the management team, who I’m very close with, didn’t see that. And basically, I became an asshole for wanting to pay someone more than them to do a job in management that they thought they can just graduate to.

John Corcoran 10:30

They thought you were an asshole. Because you said that you wanted to hire people and pay them more? Well, we

Leonard Goldberg 10:36

would have to it’s the next minute management level. Right? Yeah. So yeah, basically,

John Corcoran 10:41

that’s you have to? Did you have to let any people go that it worked for you for a period of time? Did you have any tough discussions?

Leonard Goldberg 10:47

No, that wasn’t the intent at all. intent was everyone had a position in the company, and for us to continue to grow past that, that level of $10 million, and continue to add things instead of growing, you know, in a frustrated manner, to grow smarter, not harder. We, you know, and then, and I stayed loyal, I didn’t hire the next level management and, you know, bumped everybody up a bit, because we’re all working really hard. And we’d grown to 14 or 14 15, airplane, something like that. And it did, what it normally would do, we stayed at $10 million for a couple of years, we plateaued, we couldn’t get past that. And it was very frustrating, because we didn’t have the measurement talent to really continue to grow and be at that level. And then 2008 hit. Wow,