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

John Corcoran 11:40

so many hits. So the financial meltdown. It’s interesting, we’ll get into comparing that period to what happened during the pandemic, but a different type of definite different era, a different type of response. Did your business dry up at that point? What was it like in 2008?

Leonard Goldberg 11:57

Yeah, we took the ride down. You know, people didn’t charter planes or buying airplanes, you know, especially in the private sector. And, you know, if you remember in Washington, the three big bang automotive company, yeah. went to Washington to ask for money. They flew on their private

John Corcoran 12:20

planes. Yes, sir, did not go over so well, separately.

Leonard Goldberg 12:24

Yeah. And, you know, it showed how disconnected they were to their fight department, because they couldn’t have said, well, they should have said, well, everyone here on this bench flies privately on tax dollars. Why is that? Because you need the privacy, you need the efficiency, the effectiveness of flying private, there’s a real value to it. When you’re when you have hundreds of 1000s of people employed, depending on your company succeed, you need to be in a private jet not flying southwest. Yeah. You know, so, but they didn’t, they didn’t

John Corcoran 12:55

have a great response. They didn’t have a great

Leonard Goldberg 12:57

response. So they all went home, drove three days back in their cheapest car they had. So yeah, it didn’t go well. So everybody

John Corcoran 13:06

in that affect your business when that happened, that’s kind of

Leonard Goldberg 13:09

reset. You know, immediately thereafter, every corporation was selling their jets, they weren’t flying privately. So it that was part of it, you know, we had activity, so to adjust the activity and ride the wave down. I did liquidate everything I had to keep everyone employed. I did have to cut salaries across the board, thinking everyone would buy into that to stay employed. But the folks that were I think, you know, at their limit left. They didn’t want to take a pay cut. And I had no choice. How did that

John Corcoran 13:45

Oh, you’re liquidating things. So I assume you mean you’re selling off assets, selling planes? I don’t know if you’re selling No, there’s nothing.

Leonard Goldberg 13:51

You couldn’t sell anytime. But I actually liquidated my 401k any savings I had had anything I personally built up cash wise to that point. I liquidated

John Corcoran 14:02

all that he doing all that and then he asked people to take a pay cut for the period of time and then people leave

Leonard Goldberg 14:08

the original people that I think 2006 When When I became an asshole because I wanted to hire next level bagger those minutes.

John Corcoran 14:16

So they left. So when did you hire the next level management?

Leonard Goldberg 14:22

So we rode the wave down to you know, 2008 910 and then we kind of bottomed out in 2010.

John Corcoran 14:29

How, in terms of rally, you said you were over 10 million. Can you can you share what you got down to?

Leonard Goldberg 14:35

We went down to 6 million, less than 6 million in 2010 which was still manageable, you know, because I only owned a couple of airplanes that we operated, you know, and then we had managed airplanes, so I didn’t have a lot of risks with them. But yeah, we bought out to down 10 And we really took a nice uptick in 2011 So things coming back and I had I actually was part of Embraer, when they did their clean. I was part of the advisory board when they were developing the Jets they have today and their executive jets. So I bought a fleet of Embraer executive jets, if not 103, hundreds in 2006, putting in, you know, a deposit to do that. Unfortunately, we were able to sell enough planes of our positions into our management charter programs to really help us in a nice trajectory in 2011. I did have a huge setback in 2011, as we were starting to go up and go into your question about, you know, did you hire the management is my wife was diagnosed with cancer. So I had to really focus on working, you know, managing the business, not working in the business. And I always worked in the business, I just was one of those people that couldn’t get out of my own way. Yeah. And being part of EO they teach you how to, you know, what you have to do to get that level and having the resources of people to talk to and having just a wonderful forum that I’ve been involved with for 20 years now.

John Corcoran 16:09

And we’re so so while your wife was sick, then were you able to? Did you hire enough people that you were able to step away from the business? Or was that a difficult process?

Leonard Goldberg 16:20

Yeah, it was never easy. But yes, so few people internally stepped up. And then we brought some people in that that allowed me to take care of my wife and my two young children at the time. My daughters were five and two. Wow. Yeah. So luckily, you know, they caught it early. And, you know, we didn’t expect to have to chemo because they thought they caught it early enough, but they misdiagnosed it. It was a little more advanced. But with chemo treatment, she was able to beat it. And the kicker was 30 days after she finished chemo, my mother was diagnosed with stage four lung cancer. Yeah, so, you know, we’ve not perpetuated the, the running the business well, so I could take care of my family. Yeah.

John Corcoran 17:07

Yeah. So hard. And, and just, this happens just in 2011, just as things are seems like kind of coming back for you.

Leonard Goldberg 17:14

Right. So and it did come back and I was able to still, you know, participate in the business but running it, you know, and managing the business instead of working in it. So we actually grew and was fortunate enough to have the vision in 2006 to buy those Embraer products so that that kept coming. And it perpetuated more business because we were very unique very early to that aircraft and the Phenom 300 Round Up. Today is nine years in a row has been the best selling jet light jet in the industry to

John Corcoran 17:46

being ahead of the market with that product. help set you apart differentiate you

Leonard Goldberg 17:54

correct. And turned out the jet was the perfect jet for the funnel 300 specifically was the best jet right now for the charter market. And then the light jet category. Hmm.

John Corcoran 18:08

Before there was one other one, you mentioned the Eclipse jet. Hmm. That was another one that you said when that came out, you realize that that was gonna have a big impact on the industry and kind of the economics worked out better for you. So talk a little bit about the impact that had

Leonard Goldberg 18:26

Yes, so when the traditional Jordan market was to buy a private jet back then Hawker the Lear jets, you know, Gulf streams had a huge acquisition cost. But they didn’t design planes like airlines were they gonna run a lot so you can only run them viably 300 hours a year, 500 hours a year six was was a busy busy year. So if you’re going to buy a plane that was that expensive new, and then run it 500 hours a year the economics don’t let you buy it yourself and just run it on charter, right? So you have to manage other people’s airplanes, or buy older airplanes. So the airplanes I’ll own the Navajo the king years were older 20 years old. Then you had an acquisition costs you can afford. So your operating costs were a little higher, so an older airplane. But when the clips that came out, I said here’s an acquisition cost and an operating costs that that coincide where you can buy this thing and run it viably and make a profit make a business out of it. Um, so I got that they called the lighthouse program which was a kind of advisory board for Eclipse jet. So I got to learn a lot about the company. And that gave me an education that really helped me go into the advisory board for Embraer but but the eclipse that didn’t come out quite at the level they expect. It didn’t have avionics working well enough. So it was what you know, and then obviously they went bankrupt. So it was a lesson learned but it really focused me to look at the next Generation of flight for the company to survive, right? Because everything I was I was involved in 20 years or 20-year-old airplanes. But I knew that wasn’t going to get me where I needed to go 20 years later, right, which is where we are today. So today, those planes would be 40 and 50 years old. That wasn’t that’s not a viable company.

John Corcoran 20:20

You know, you had a background in training in flight, you had your your pilot’s license, what you’re describing now to me is like, sophisticated financial modeling. So, tell me a little bit about, you know, how you’ve adapted over the years and learn to do these types of projections. I’m sure you have experts around you, but still, like, this is complex financial modeling that you had to get really comfortable with? Yeah.

Leonard Goldberg 20:47

So if I had to know it, I had to learn it, right? So I resourced and figured out how to learn it. And, you know, to go back to EO, I mean, they just have the resources available. They have, you know, you know, our chapters grown tremendously, you know, I think we’re one of the biggest chapters in the world. So we just have access to people, and then the resources and the educational events we’ve had. So that’s what that’s always been a consistent resource for me. But you know, I, and now with the internet, if I need to know something, I research it, if I figure it out.

John Corcoran 21:25

But during this time period, you know, there’s there’s EO which is wrapped around entrepreneurship, but there’s industry knowledge, that’s helpful, too. Did you have, were there other charter company owners that you looked up to or that you knew or you befriended during this period of time? That was helpful for you? Yeah.

Leonard Goldberg 21:43

So back then, Florida, jet Hapa. Jet. Were some of the companies that I used a lot, learned a lot from, you know, that there was a lot, the National Business Aircraft Association, and B double A, is a resource I’ve used throughout my career as well. They have they support our industry, right? They’re kind of our, our, our advocate is, what would you call it their advocates? Yeah. So they also do educational programs. So when I first started my company, for the first seven years, I went to Nell Sanders PAC seminar, just so I knew, the taxes that apply, how to apply them to the Manage aircraft, the own aircraft, the federal excise tax, that that’s omnipresent in my business that we have to pay. So I knew that fundamentally, early on I, when I was three employees, I hired a payroll service, because I, you know, I didn’t want to do that. I want to make sure that that was done right. Taxes has always been, you know, early on, I knew I had to make sure I was paying taxes or structuring everything correctly around taxes. So I reached out the NBAA Nell Sanders tax seminars for seven straight years. And anyone that works for me that has anything to do with running our books, I go to they go to those same, some seminars. And the NBAA just has other structure I follow when I was building the business growing the business.

John Corcoran 23:14

Yeah. So let’s flash forward to 2020 COVID hits when did that? When did that hit your radar? And also, in retrospect, looking back now? Do you feel like you were prepared for it in any special way, given what you lived through previously?

Leonard Goldberg 23:33

Yeah, I think as you grow a business, you get tougher, right? And you get smarter. In 2016 into 17, I did my last pivot the business where we were, we had many different types of airplanes. And the industry has grown to a point you know, with insurance with pilots, the pilot shortages, omnipresent, since you know 2015. Just streamlining everything, getting anywhere, everyone culturally into fit into your business making things easier. So we really streamline the business and phase out a lot of different types and focused on on the MBO products. Not that that’s the only type of manage. But as far as Charter goes, the Embraer product is what we focused on. That really helped us when COVID hit because we’re

John Corcoran 24:27

all on here focused on one type of product primarily. Yeah,

Leonard Goldberg 24:31

primarily, you know, we still manage other different types of airplanes under but we don’t charter them out, right. They’re not run commercially. But what happened was, we were able to get very focused as a management team, we made an immediate cut. And I learned a lot from 2006, seven and eight, especially 2008, riding the wave down. You know, we had to we had to make the tough decisions, and we had to make the right decisions to be here in a few years. So that guide the management team, we were on the phone every morning on a zoom call, you know, and of course, technology helped a lot, this last go around as well. And we made you know, we made tough decisions, right decisions. We actually were very busy in March. So it hit in February, you know, and then really hit March. But in March, we were, you know, our industry was getting everybody where they wanted to sequester. Hmm. So then April,

John Corcoran 25:25

people were we really lucked out. People are fleeing and going to remote spots. Yes. Or leaving the cities leaving? Yeah. You know, wherever

Leonard Goldberg 25:35

they had their resort hands or wherever they wanted to go to be requested. And then

John Corcoran 25:40

in a New York to Jackson Hole route must have been pretty heavily or

Leonard Goldberg 25:43

Jackson Hole in New York, Miami. Yeah. Then we really, you know, in April, we I think we flew 32 charter hours from, you know, 250 bucks a month, a month, down to? Yeah, so yeah, that was a big hit. Fortunately, a couple years earlier, a friend of mine came to me that used to work for the cruise lines. And we got as an approved vendor for SIBO and cruises. Well, in April in May, they needed to get all their passengers off the ships and home. And then the crew. So So in April, and May, when we were very slow flying charter. We were brokering trips for them flying people all over the world. Wow. That helped us. So we just looked at every two weeks because we do payroll every two weeks. So we just focused how do we make payroll two weeks, and after that two week segment. So we just in March, you know, March, we were busy enough to get us to mid April, then these fights were good enough to get us to, you know, yeah, keep going. Now, when

John Corcoran 26:47

you and I first spoke, I remember you kind of jokingly said that your mindset at this period of time was, well, I’ve been at this for 25 years. And I guess this is how it ends.

Leonard Goldberg 26:56

So yeah, yeah, exactly. When in April, when things got really slow in May, I’m thinking here comes June is gonna be my 25th anniversary in business. And I’m not going to make it really close. You know, I started jogging a lot. So I get my lungs, my runs got a lot longer, so a lot of time to think. And I was like, I gotta figure this out. There’s no way I’m gonna give give up 20 25 years of doing this.

John Corcoran 27:23

Right, right. And fortunately you said by June there was an unusual uptick. What do you think you can attribute that to?

Leonard Goldberg 27:31

Um so I it came down to wealth, right? The wealth, the wealthy people weren’t going to stay sequestered. And we couldn’t go into nationals. So domestic travel picked up for private jets quite a bit. In June, we really saw an uptick in July. And then in August, I realized this looks like it’s, it’s coming back in full force. And, and we started growing, I got had a tremendous amount of people, old customers, customers that didn’t charter anymore, sold their planes come back and say, Okay, I want to buy an airplane. I want to fly charter. I’m not going the airlines anymore. Yeah. So,

John Corcoran 28:14

you know, anyone could afford it avoided the commercial planes.

Leonard Goldberg 28:18

Yeah, so we that was the principal, right? So the principal wasn’t like mercy, and they weren’t gonna let their kids fly commercially, and they weren’t gonna let their parents fly commercially. So it came back in full force.

John Corcoran 28:29

Yeah. Now, since that point, some of the biggest challenges for you like every business out there these days, hiring, talent recruiting, and an unusual thing for you is that you have to pay for a lot of training, you hire a pilot, and they have to go through a whole training program before you even know if they’re going to work out or not. But there’s an unusual thing in your industry where there is a loan agreement for their training if they leave within a year. So tell us a little bit about how that works.

Leonard Goldberg 28:58

Yeah, so there’s a huge investment in the pilots that come in here and their training, especially if they need initial training. So the way we can kind of tie them down to stay for a year, especially since the industry, you know, the pilot shortages, they can get hired almost immediately coming out of training, they go somewhere else. So to try and heads that, first and foremost, we really focus on our culture. You know, we don’t we’re small enough where we can focus on culture and try to make sure we have people that want to be here, right, that’s half the battle. But you don’t always get that. So we do have them signed a loan agreement for the training that they initially do. That’s amortized over the first year.

John Corcoran 29:41

And is that hard to get? Is that just industry standard? So it’s not hard to get people to?

Leonard Goldberg 29:46

Correct Okay,

John Corcoran 29:47

got it, got it. And then what have you found is such a unique skill set the roles you need to hire for so what has worked for you for recruiting and hiring people finding talent these days.

Leonard Goldberg 30:00

So Keith Drake, my Director of Operations does all the pretty much all the interviewing, initial interviewing and hiring, key second careers came into flying. So his original career was an executive for Lowe’s. So he was very involved with upper level management. So he’s one of a skill set to my company that’s been very helpful. And in hiring people. So we have a pretty extensive hiring process, minimum of three interviews with Keith in each interview, but then we also add people to each of those interviews as people go through them. And, you know, we’re looking for more personality and judgment than we are the, the fight skills, you can train people to the fight skills. So we’re not just trying to fill a seat in the cockpit. We’re really looking for people that fit in here in our culture, we don’t always, always hit but we’ve done better than, yeah, better more often than not. Yeah.

John Corcoran 31:04

I want to ask you about how the industry is different today, compared to 25 years ago, you mentioned earlier that it used to be back then people picked up the phone and called I’m curious if you know, do people booking a $50,000 flight just through your website? Sight unseen? They’ve never talked to you before? And that’s where that is correct. The volume of the lease. Wow. That’s pretty phenomenal.

Leonard Goldberg 31:27

Yeah, it’s, it’s hard for me to comprehend. You know, I have my fly corneas, charter coordinators, booking these trips. And they’re, they’re a lot younger than I am. When I did it was late, you know, pick the phone was all relationship based people wanted to meet you talk to you. And it’s not that way. You know, I remember a few years about six years ago, one of my charter grenades is at his desk and hadn’t touched the phone all day. I’m like, I What are you doing? He goes, book seven trips, right here. What What are you talking about? He goes, everything’s on the internet. Like, what? as possible. And then when he keeps going back and forth with someone on questions, you know, texting or emailing. This is after the third one pickup sitting on your desk, that black thing that handle pick it up. And those buttons you call somebody that

John Corcoran 32:16

did? Does he do it? Follow your advice? I say Whatever, man, I’m gonna keep on texting.

Leonard Goldberg 32:22

Yeah, like you text. Yeah.

John Corcoran 32:25

Well, I mean, it’s interesting these days, I mean, like, even 10 15 years ago, that would be considered, you know, faux pas or business to do that. Now. It’s like, if you’re, if you’re not able to text back with a client, even a, you know, high net worth individual probably there’s, there’s an expectation that that’s going to be available to them as a communication channel. I get annoyed. I know, I don’t know about them. But I get annoyed if I like, I can’t text back with this. I want to give them business, but

Leonard Goldberg 32:51

they need to text me back. Yeah. So and you know, even booking your flight now. We send them the flight confirmation know if there was do it click and the payment thing you know, it’s very simple. Yeah. But some of our older clients, you know, absolutely frustrated with it. Yeah, sure. They want to be handheld and talk to, but they’re not many of them left. Right, right.

John Corcoran 33:13

I want to ask you, you got into this because of your love for flying. And sometimes when people go into a line of work, where it combines their love, they kind of lose the love for it. Do you still have the love for it?

Leonard Goldberg 33:26

Yes, absolutely. So you know, I used to fly in the right seat of the Navajos, you know lepsy You know, the nav was King years because they would pop the Bahamas around the Florida and I still work a full day I’m still in touch the flight segments are an hour hour and a half. But when we went to jets, I didn’t have the time to stay current, you know, go to flight school for three weeks you know, take a month out of my calendar to get proficient enough and get hydrated and then fly enough in a jet to really stay current. So I kept saying I’ll get back to that you know one of my main motivations to buy the fleet of ember Jas was so I can go pick them up in Brazil and find to deliver them to United States but I never had the time to really do the training portion of it and stay current with the thought that I could always get back to it. Well fast forward after growing the business it was 15 years later, and when COVID hit and I had some more time I actually went got current again in a Cirrus it’s the airplane with a parachute.

John Corcoran 34:25

Yeah, really big into safety.

Leonard Goldberg 34:29

Yeah, so I went and got currently serious I’ve been flying for a little over a year. Now I just put actually an order in Tuesday for a new Cirrus.

John Corcoran 34:37

That’s the one with also the button the Fly Me Home button. Right.

Leonard Goldberg 34:41

So the jet This is the piston airplane doesn’t have that yet.

John Corcoran 34:44

Can you explain what I’m referring to? Yes.

Leonard Goldberg 34:47

So there’s a button on board the airplane and in their jet that they put out the vision jet. And I call it the Ohshit but, but they call it a return safer, safer turn. Okay,

John Corcoran 34:58

yeah, I’ve watched Any use of it, it’s phenomenal. It’s insane blows your mind.

Leonard Goldberg 35:02

It’s unbelievable. You know, anyone on board can hit it. And basis

John Corcoran 35:06

something happens to the pilot, the people in the backseat instead of freaking out, they hit the Shift button and it flies you home flies you back around to the nearest airplane, right airport,

Leonard Goldberg 35:14

right? The nearest airport with the approaches that the airplane can fly. So it can’t just find any airport, it has to have the approaches that the DPS approaches they are playing fly, but the airplane will actually communicate with air traffic control. electronically, they’ll Squawk 7700 That’s an emergency. And the plane will actually communicate with air traffic control. And it’ll land, it’ll auto land.

John Corcoran 35:41

Wow, it just kind of blows your mind, isn’t it?

Leonard Goldberg 35:43

And it has the parachute like the other the Cirrus piston airplane.

John Corcoran 35:48

Wow, amazing. Amazing. Yeah.

Leonard Goldberg 35:51

I was gonna say the parachute has been pulled 107 times. And I think there have been Zero Fatalities in the polls.

John Corcoran 35:58

Oh, wow. Since they installed those

Leonard Goldberg 36:01

120 20 plus years they’ve been on the airplane.

John Corcoran 36:06

Wow. That’s amazing. And I wonder if the Motion button has been used yet?

Leonard Goldberg 36:10

I haven’t heard. I haven’t heard it. I don’t think it has stats are that a couple of years? Maybe they just do it for fun. Like, I want to start

John Corcoran 36:19

this. Yeah, exactly. This has been great letters really enjoyed talking about your trajectory, your journey with the business and everything. I want to wrap things up with the question I was asked, which is a big fan of gratitude. And if you look at your peers and contemporaries, others in your industry, however you want to define that could have your specs, who do you admire that soon? Good work there. I know we chatted a little bit beforehand about it. And you talked about the impact that being part of you and joining the board had for you. And that was one example that you wanted to talk about.

Leonard Goldberg 36:49

Yeah, there’s been so many, you know, everyone in my forum, but really a pivotal time, I think was Oscar DiVeroli came in as president of our chapter. And we were a tight knit chapter at 60-65 members. And he really changed the trajectory of the chapter. And that’s where I really think everything clicked for me as far as running a business and all the things he co teaches and just combining everything that I’ve learned from my industry, and he asked me to be on his board, and just that whole board clicked and then just the change in our chapter change that helped me with my business. So I mean, if I have to pick someone that popped into my head, he has been a parolee.

John Corcoran 37:40

Yeah, I did an interview with Scott Empringham who is in Orange County. And as his business was failing. The president of his chapter asked him to join the board. And he tell told a super funny story about it. He was like, you know, like, desperate, his businesses crumbling all this kind of stuff. And Keith, who I also interviewed, was talking to, in Scotts impression of him was like, And he’s like, this military background guy kind of like listening to like, whatever, you know, go. Yeah, can you join the board. But Scott ended up saying that in having such a big impact for him personally, that focus on something else that focus on someone else, which we hear a lot of times it kind of the caregiver mentality, and helping us fix and heal ourselves. So, for you, you know, being on the board, what did you bring back to your business? How did that help you to with your business?

Leonard Goldberg 38:35

Yeah, and that’s why my business was doing so well, right. 1009 ish tennis. So it led me the big change was work going from working in the business to and really, really understanding what communicating your vision to your businesses, you know, your was really digging deep on your why really establishing a true culture for your business, and then holding people accountable, that work in your business. So it all kind of came together at that time. So I can work on my business, which subsequently, you know, and I think that’s why I was successful when I rolled out of my business just falling with the economy, to bottoming out. And then as we’re starting to grow and really ramp up, back up again. When my wife had cancer mother had cancer. I was able to run the business sort of run into business. Yeah. And I don’t, I think that experience really helped me do that. Where it was successful enough where I’m still here.

John Corcoran 39:40

Yeah. Lennar, this has been great. Where can people go to learn more about you connect with you learn more about your business?

Leonard Goldberg 39:47

Yeah, you guys go to the website www.goldaviation.com. And my contact informationPs on there. I think that’s the best way to do it.

John Corcoran 39:56

Excellent. Leonard, thanks so much.

Leonard Goldberg 39:58

My pleasure. Thank you.

Outro 40:00

Thank you for listening to the Smart Business Revolution Podcast with John Corcoran. Find out more at smartbusinessrevolution.com. And while you’re there, sign up for our email list and join the revolution. And be listening for the next episode of the Smart Business Revolution Podcast.