Authentic Connections In The Air With Nik Tarascio

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Nik Tarascio was born into the family aviation business.

While we were probably picking our noses, Nik was working on airplanes by the age of four. He received his pilot’s license by the age of 16, was flying Lear jets by the age of 19 and, today, is the CEO of Ventura Aviation.

Nik is responsible for his multimillion dollar family charter company. He is an excellent musician and is still a practicing pilot himself.

Despite his history of social anxiety, Nik is also now building a YouTube and social media community sharing amazing flight adventures and documenting it for the world to see.

Today, we’ll be discussing what it’s like running a tight-knit family business. Nik shares how to make aviation more accessible and how he gets out of his comfort zone.  And he also shares how he is able to leverage his unique talents to cultivate meaningful relationships miles up in the air.

Take a listen!


Key Points From This Episode:

  • How working on airplanes cultivated Nik’s entrepreneurship.
  • Why Nik didn’t care about school or college.
  • Getting a pilot’s license at age 16.
  • How Nik accidentally became CEO.
  • The epic fail Nik is still paying for.
  • Navigating family dynamics in business.
  • Why Nik and his family love to teach.
  • When the engine cuts in the cockpit.
  • How Hamptons chic lead to Summit.
  • Overcoming the awkwardness of being awkward.
  • Nik’s no-more-than-24-hours trip.
  • Making authentic connections.
  • Is aviation as expensive as we think?
  • And much more!














Links Mentioned in Today’s Episode:

Venture Air Website –

Nik on Twitter –

Nik on LinkedIn –

Nik on Facebook –

Pilot Nik YouTube Channel –

Nik on –

Transcript Below:

Read Full Transcript


“NT: You know what? I learned how to overcome fear in a cockpit, and so I really want to do something with that. I’ve thought a lot about taking a lot of that learning from the cockpit, a lot of that high-performance thinking and creating something where I could teach people about the best learning from the cockpit without them having to be a pilot to do it.”


[0:00:21.6] ANNOUNCER: Welcome to The Fail on Podcast where we explore the hardships and obstacles today’s industry leaders faced on their journey to the top of their fields, through careful insight and thoughtful conversation. By embracing failure, we’ll show you how to build momentum without being consumed by the result.

Now please welcome your host, Rob Nunnery.


[0:00:47.4] RN: Hey there, and welcome to show that believes failing in a hyper-focused way is the only way to achieve your dreams. In a world that only likes to share successes, we dissect the struggle by talking to honest and vulnerable entrepreneurs, and this is a platform for their stories.

Today’s story is of Nik Tarascio. He was born into the family aviation business and was even working on airplanes by the age of four. As the CEO of Ventura Aviation, Nik runs a multimillion dollar charter company and is also a pilot himself. He got his private pilot’s license at the age of 16 and was even flying Lear jets by the age of 19. He’s also now building a YouTube and social media community sharing amazing flight adventures and documenting it for the world to see, and it’s just extremely well done.

We’ll be discussing what it’s like running a family business along with the challenges of actually working with people you have personal relationships with. We’ll talk about how Nik is able to leverage his unique talents that cultivate deep relationships and what he constantly does to make sure he is growing and getting out of his comfort zone on a regular basis.

First, I’ve been traveling a lot as is and I have even more travel coming up, and luckily all I need to travel with is a backpack for one reason only, it’s a shirt from a sweet Toronto apparel company called Unbound Merino. They have clothes made out of merino wool and, get this, you can wear it for months on end without ever needing to have it washed. I don’t know if that’s recommended, but you can do it.

Just talk about an absolute traveler’s dream, never check a bag again. Just please check it at the show notes page at for an exclusive Fail On discount that you won’t be able to get anywhere else.

Of course, if you’d like to stay up-to-date on all the Fail On podcast interviews and key takeaways from each guest, simply go to and sign up for our newsletter at the bottom of the page. That’s


[0:02:32.5] RN: How did you get started on entrepreneurship and when was this?

[0:02:37.0] NT: I don’t have a defining moment where it shifted. I grew up in a family business and I think it was a slow progression. I think it was really more of just — I tried to copy everything my dad did and try to master every skill he had.

[0:02:53.6] RN: What was he doing?

[0:02:55.0] NT: Early memories were things like we would go out and fix airplanes. We’d take an engine in our basement and rebuild an engine in our basement. I remember 8 years old literally building engines in our basement. We carry it up the stairs, put it in a wood panel, the Grand Caravan, to drive it out to the airport and put it on an engine. I mean put the engine on the front of an airplane.

I really don’t think I was in entrepreneurship until really well into my 20s actually. I think I thought I was. I was like, “Oh, I’m running a business or I’m involved in the management of a business.” Really, I was acting more just a mirror of my father.

[0:03:28.1] RN: How early were you actually working in the business with your dad though? Were you doing stuff at 10 years old to help out? What was that like?

[0:03:35.5] NT: Here’s the way to think about it. Airplanes are tiny. The ones we work on are small and we were tiny kids, so my dad being an entrepreneur was like, “I see opportunity here,” climbing the tail of that airplane and buck some rivets. We could fit in way better. Literally, from the time I was five or six, I was working on airplanes.

I’d say I started playing a more major role when I was 13 and I was doing aircraft sales form. Again, it was more of like, “What does he need to do the calls for?” I have these — At the time, it was like classified ads that I would call and try to negotiate airplane deals. It was funny because I’d be —

[0:04:10.1] RN: At 13?

[0:04:11.0] NT: Yeah. At 13.

[0:04:12.0] RN: That’s awesome.

[0:04:12.2] NT: I’m negotiating a hundred thousand dollar discount on an airplane and I made $7 an hour. I have no concept of money. It was either, “How about 1.1 instead of 1.3 million?” Versus, “Can I make $8 an hour dad? That would be really nice.” Again, I think I was just more of like — I was just a good worker.

[0:04:30.6] RN: Was that at 13? I mean did that just come from your dad — You were watching your dad just bust his ass all the time? How did that from? Where do that come from?

[0:04:39.3] NT: Yeah, I think so. My grandfather was that way. My dad was that way. He just gets it done and he never complained about the amount of work. He was just, “I’m going to do whatever it takes to make it happen.” He would take stuff and be like, “Hey if something is not right, take it apart and put it back together again.”

Very early on he instilled this idea of like understand the fundamentals of what you’re doing. Look at all the core parts, put it back together, you’ll have a greater understanding. Always very mechanical. I actually started the business when I was 13, but I didn’t start it to make money, because I didn’t know anything about sales and marketing. What I knew is that I buy musical instruments, because I’m a musician and if I’m a company that sells musical instruments, I get to buy them at wholesale price.

[0:05:16.7] RN: Yeah, you get discounts.

[0:05:17.7] NT: That’s all I did. I just bought my own stuff at discount. Again, it’s just actually goes to show, I was a thrifty ops guy. I was not a sales and marketing guy.

[0:05:26.6] RN: Gosh! Did you actually end up selling any of those instruments?

[0:05:30.5] NT: I think I sold to my high school some stuff. My friend was like, “Oh, I’ll buy through you what I need to buy for a stage crew.” I was like, “Okay. Cool.” I think, all in all, I probably made a thousand dollars. It was a joke. Everyone else we meet in our networks is like, “When I was selling candy, I made $450,000 at 11 years old.” I’m like, “I made a thousand dollars.”

[0:05:50.3] RN: Yeah. I was telling you when we’re eating Indian food, I didn’t even know what entrepreneurship was until I was out of college. I’m right there with you. I was not born bring lemonade and building a lemonade franchise in my neighborhood like Gary Vaynerchuck always talks about.

You’re 13 years old doing sales. You’re 5, 6 years old crawling into the back of little airplanes. I don’t know what you said. Buck a rivet? I don’t even know what that means. I’m guess you’re screwing something or hammering something.

[0:06:19.3] NT: Sort of. A rivet is a piece of metal that you hit with an impact gun and it flattens it. It flattens the rivet.

[0:06:26.4] RN: I’ve seen them on airplanes.

[0:06:28.0] NT: Trains have them. Yeah, exactly. On the side of an airplanes, those aren’t screws, those are actually pieces of metal that are formed to hold the skin together.

[0:06:33.5] RN: Got it. So you’re doing that?

[0:06:34.5] NT: Yeah.

[0:06:36.0] RN: At five?

[0:06:36.9] NT: Yeah.

[0:06:38.9] RN: Were you not playing with friends? Did you not have friends? That’s not a normal childhood. You’re negotiating a hundred thousand dollar deals and bucking rivets.

[0:06:47.2] NT: Yeah. I was kind of a nerdy, socially awkward kid. I used to get the crap kicked out of me when I was little. I never really liked people in my school. I wanted to be around my school. Instead, I had friends that were 40-year-old pilots. I would sit around and talk to pilots all the time. That was my group really at the end of the day and they would talk to me in ways that you don’t talk to a 13-year-old, like, “Alright. Tell me about the crazy stuff you get into?”

I had a really strange life where I felt more like I was in my 20s and 30s when I was a teenager. I knew I never really belonged in school.

[0:07:19.8] RN: You didn’t belong in school, but you graduated high school?

[0:07:22.5] NT: Yeah. I graduated high school. I went to college. Again, I was like this super nerd.

[0:07:26.8] RN: You got good grades. You really cared or you didn’t care?

[0:07:28.7] NT: I was in like number 8 in my school graduating. I got a scholarship to college. The thing is that I didn’t give a shit. I was one of those guys that like I was in some talented program, like talented kids, gifted kids, whatever the hell they call it and they were like, “Oh! You have to write a book report every year,” and I’d quit right before the book report every year. I was like I don’t care. I don’t see what this does for me. I knew I had good raw materials, I just didn’t have anything to do. However, flying was really sexy and cool, so I mastered aviation in a very, very young age.

[0:07:58.3] RN: When did you get your pilot’s license?

[0:07:59.8] NT: My 16th birthday.

[0:08:01.6] RN: At 16. Okay. So you’re still in high school. That’s — You’re doing crazy stuff. I played tennis growing up, but I wasn’t like bucking rivets and negotiating a hundred thousand dollar deals and getting my pilot’s license. That’s awesome.

You got a scholarship for college. Did you go to college and graduate?

[0:08:20.6] NT: No. I did about a year and a half. Went to Polytechnic University, which is now NYU Poly. The thing is I was really good at math and science, physics, computer stuff.

[0:08:30.3] RN: All the stuff necessary to be a pilot basically.

[0:08:33.3] NT: Kind of. Yeah. Actually, avionics, I use it all the time. I use all the stuff I learned there. I was one of those guys that never went to class, and then would just get an A.

[0:08:42.9] RN: A on the test, on the exam.

[0:08:44.8] NT: Until in my second year I started having classes where the teacher said they were grading me on my attendance, and that’s when I was like, “I’m already not digging this.” My parents wanted me to go and I wanted to be a dick, so I was like, “Alright. I’ll keep going.” At some point I was like, “Look. It’s my money, because it’s my scholarship and I don’t want to be here and I don’t want to live this lifestyle.” No offense to people that went to computer engineering schools, but it wasn’t exactly the culture of people that I wanted to be around.

[0:09:07.8] RN: Would you have gone if you didn’t have a scholarship?

[0:09:09.9] NT: No.

[0:09:11.4] RN: Just for financial reasons.

[0:09:13.5] NT: I just didn’t care enough. I went because it was easy, and that’s why like as long as I was getting good grades and I didn’t have to go to class. I was in. As soon as they were like, “No. You actually have to work at it and it’s going to cost you something.” I’m like, “No. No freaking way. I’m not doing it.”

[0:09:27.1] RN: What were you hoping to get out of your pilot’s license at 16? Did you want to be a fulltime pilot, fly charter jets or fly the airlines? Why did you get it? Just because you grew up around it?

[0:09:37.0] NT: Yeah. I think it’s one of those cases of when you’re a kid growing up with a dad who flies and fixes airplanes, talk about some Superman shit, right? If the plane was broken he’d be like, “Hold on. Get out. Take the [inaudible 0:09:49.9] off. Fix the engine. Get back in the plane.” I’m like, “That guy is a bad ass, huh?”

I think there was — Really, when I think about it, it was probably like a desire to validate myself in his eyes of like, “I just want to master everything he mastered because I appreciate that and I admire it.” Like I said it wasn’t — I think it was — Whatever I said. 19, 21, 22, when I realized like I’m actually really good at all the things he does and I’m not fulfilled, like it just doesn’t matter.

[0:10:18.5] RN: Yeah. At this point, you leave school. Are you working fulltime in the business with your family?

[0:10:22.2] NT: Yeah.

[0:10:23.1] RN: Okay.

[0:10:23.2] NT: I left, like I said, about a year and a half, two years in. I quit. I was done. I had no desire, and then I just went to work fulltime with the business.

[0:10:29.9] RN: What were you doing with the business when you went fulltime?

[0:10:31.8] NT: At the time I was a mechanic and an avionics guy and I was flying Lear jets, so it’s both of those. At 19 I started flying Lear jets.

[0:10:39.4] RN: Like a charter jet. For charter clients that needed to go from New York to —

[0:10:44.5] NT: Wherever. You name it, I’ve been there. I’ve been all over the country. I’ve got over 1,500 hours flying jets. The thing was that my mom wanted me to be a captain because she’s like, “Well, we need — When you get to be 23, which is the age that I had to be at the time. She said, “I want you to be a captain, because it’s hard to get captains. They’re short supply.” I refused. I refused, because I said, “I see where this goes.” Now that I’m clear on the fact that isn’t the thing I want, this isn’t the part of the business that I want to put myself in, I knew that if I did that, if I got my captain’s license I couldn’t overcome her guilt. She’d be like, “Come on. We need you to fly this trip.” I’m like, “Uhhh —”

[0:11:17.9] RN: Yeah. You have to do it.

[0:11:19.1] NT: Yeah. I got really clear on the fact that —

[0:11:22.5] RN: You’re a business need — like, “we’re going to groom our son to fulfill a business need for us.”

[0:11:29.8] NT: My dad built an army. He built this little army of kids. My brother was working on airplanes, my little brother was doing other stuff. Now, he runs our maintenance department. My sister was working in the admin stuff with my mom. Our friends moms worked in the office with my mom too — It was like —

[0:11:45.1] RN: Full team effort.

[0:11:45.3] NT: Yeah. All the kids were basically the hiring team.

[0:11:49.9] RN: That’s awesome.

[0:11:50.0] NT: Yeah. It was interesting, because I love flying. I love aviation, but I think I just always had this burning feeling that was like, “Hey man, I don’t think your greatest value is going to be flying an airplane, though I love it. I just said, “There’s something that — It doesn’t make sense.” The company needs something else from me, and I never knew what it was until I was in my mid-20s, maybe later 20s.

[0:12:12.5] RN: You had that feeling and then what did that compel you to do?

[0:12:16.8] NT: What I would do is I would master every one of the skills. I was like, “Okay. I’m going to be a master mechanic.” Then I was like, “Cool. Now, I’m just going to like manage the mechanics.” I’m like, “Let’s not do it. Let me master avionics. Build avionic systems.” Then it was like, “Oh, now I’m going to master the flying thing and I’ll try to develop other pilots.” I really didn’t go too much down that road.

I just saw more like I always want to fire myself. If I could just keep firing myself, everything is cool. It was this really like slow progression. Again, it wasn’t until I accidentally became CEO that things started to make a little bit more sense. I was at a networking event with my mom and my entire family, none of us are like really super social people. In fact, I think we’re all like a little shy and insecure in that setting. We were at the Bethpage Black Golf Course or whatever, and this guy comes over and he’s like, “Oh! There’s this event in the city, the CEO Trust.” He saw us like wallflowers on the wall. “This event the CEO Trust. I think it’d be great for you guys. I see you’re in the jet business. That might be a great place to meet some CEOs.” He’s like, “Would you want to go?” We’re like, “Yeah, we’d go.” He’s like, “No. Which one of you is the CEO?” I like just paused and my mom goes, “He is.”

[0:13:21.7] RN: Pointing to you?

[0:13:21.9] NT: Yeah. That was it. I became the CEO. I went to work the next day and I was like, “I’m the CEO.” My dad goes, “It’s just a title. Don’t get excited.” Then I was like, “What the hell is a CEO?” I’ve heard that term. You hear about it in the news. Everyone said CEO’s are overpaid and blah-blah-blah.

[0:13:38.0] RN: You said you’re in your mid-20s. Is this 25 or –

[0:13:39.8] NT: 27.

[0:13:40.4] RN: 27. Okay. You’ve been in this business the whole time. Have you guys had a structure like that from the beginning where you have CEO, a CFO, or it was just a family just kind of mishmash, let’s make this business happen?

[0:13:53.4] NT: Yes. It was just — You do what you need to do when you need to do it. We had an accountant. We had mechanics that would help out, but there was no real corporate structure. There was no org chart. There was really no delineation of who even the manager was. It was just like, “I guess my dad is in charge of everything. I don’t know how any of these works.”

My method was he’s so busy doing maintenance and flying airplanes. If I just do stuff really — If I’m moving really quickly, no one can even keep up with me. It’s not like anyone could tell me no to anything, because I’m just moving so fast.

At that point I started to really try to dig in to what is the CEO do and how would that look in a small business, because clearly I’m not a guy that sits at a big desk and all that kind of stuff. It wasn’t until — Actually, I accidentally ended up at Summit Series, which was kind of just a total fluke. When I went there I actually met one of the attendees and asked them —

[0:14:42.8] RN: What year is this? Sorry.

[0:14:43.7] NT: This must have been 2009. Yeah, 2009 was when I first connected with the summit guys. I had met one of the other attendees and I asked him, “What’s been the most profound thing for you?” He said, “Entrepreneurs Organization.” I think something [inaudible 0:15:01.6]. I never got involved with [inaudible 0:15:02.6], but I joined it and I was like, “What the hell is this?” Talk about imposter syndrome, I was like —

[0:15:09.8] RN: Why am I here?

[0:15:11.7] NT: I’m just a kid that grew up in aviation that plays with all these toys, but that was kind of the big turning point.

[0:15:17.2] RN: From there, what were your biggest struggles in terms of — You’re now CEO. I know your dad said it was just a title, but you actually took the responsibility upon yourself to actually act that title, right?

[0:15:30.0] NT: Yeah.

[0:15:30.4] RN: What were the biggest struggles in terms of — Was it tough getting staff at the time? I know we talked earlier. You said you have 36 employees now. What was the employee count then and was it tough getting them to buy in to you as the technical CEO?

[0:15:45.1] NT: Those are two good questions. I don’t remember the staff count. Maybe we were — we probably weren’t that much smaller, to be honest. We’re probably almost the same size, just unstructured. It was like the wheels were coming off the bus, because there’s just no real leadership or structure in the place.

Regarding some of the stuff, a lot of the staff were my friends at the time. They were kids that I went to high school with. They’re like new through my town and they’re not there anymore. I think that there was some resentment at times of even some of the employees that were in other roles, like some of the pilots were like, “Hey, this kid was a copilot for me. Why am I going to listen to him?” Of course there the entitlement stuff, like, “Oh, he’s just Mike’s son. What the hell does he know?”

I had to overcome a little bit of that. However, my family never felt that way. My family was always like, “Nik is capable. He’s smart. He’s committed and he does a really good job.” We’re one of those rare family businesses where we don’t have family business issues in that way, which has been really unique.

Actually, it’s the opposite, because I said to my dad at one point, I’m like — we had these executive team meetings where we’re trying to figure out like, “I think that’s what we need to do. You have an executive team meeting, you talk about strategy behind a closed door.” He was just like checked out. I was like, “You know what? Don’t come to these anymore.” He’s like, “Oh, awesome! I don’t like this.”

He was clear on “I want to fix and fly airplanes” and my mom wants to do what she does, which is more the selling the charter side. Actually, it was just this really beautiful circumstance. Everyone was really clear in what they wanted to do. Then they started to see the value of what I was focused on, of like, “How do we get ops manuals and structure and procedures and really start to find efficiencies?” I still feel like I got a long ways to go. It is a hard business to play in.

[0:17:21.1] RN: Going from there to now, what’s been really the biggest struggle? Have you had any epic failures where you maybe didn’t have enough experience there and you’ve made the wrong call and cost your company money. Or maybe you made a bad hire? What’s been the toughest learning curve to come over?

[0:17:39.0] NT: There’s one we’re paying for still. 2007, December, we decided that we wanted to buy another Lear jet and —

[0:17:50.3] RN: You had how many at this point?

[0:17:51.3] NT: We had two, I think. Yeah, I think we had two at the time. We decided we wanted to add another one. It was just like — I think my mom said it the other day. She’s like, “We should have known then that buying your own airplane is a stupid thing to do.”

We’re actually in a decent position. We bought this airplane in 2007 in the end of the year. Within six months the market had crashed in 2008 and the value of the plane plummeted, and we’re still paying off — We’re still paying down all that debt. We still have this loan that — These are long term loans we took for like 15 or 20 years. We’ve still got the debt of this plane that cost a fortune at the time and is really not competitive. It’s not that —

[0:18:31.7] RN: Not many people want to fly on Lears anymore?

[0:18:33.6] NT: The thing is that there’s a lot of companies that are operating those airplanes, but the difference is that many of them bought the plane after 2008, so their note payment is a fraction of our note payment. It was one of those things where I was like, “Man, I really wish we had thought that out a little bit better and figured out what the timing was.” Never in my mind did it even become like, “Let’s do like a SWAT analysis of this. Let’s look at like what could go wrong.” Right? There was none of that stuff. It was just like, “Yeah, another Lear jet.”

[0:18:59.0] RN: Let’s buy it.

[0:18:59.6] NT: “That sounds awesome. I like growth.” It was just this very emotionally-driven — I was like an excited idiot. I was like, “Yeah, let’s get that new plane.”

I think that having that rounded perspective of like if thing went wrong, what would that look like to the company? If things go right what would that look like, and let’s look at both extremes and make sure that, one, the upside is worth it. Two, the downside wouldn’t kill us.

Look, we’ve made it through. We’ve persevered, but we’re instead of taking a bunch of money home every year, we’re just basically paying this particular plane, this flat that’s not really making any money.

[0:19:33.3] RN: Got it. I know you mentioned earlier that — You obviously grew up in the family business and you kind of stepped into a CEO role after learning the entire business from the ground up, because that’s the environment you were raised in. I know we’ve talked a little bit about you looking at other opportunities, obviously, within aviation but also stuff outside of aviation. What else are you looking at in terms of being purely an entrepreneur?

[0:20:01.7] NT: There’s a piece of the business that it was — we actually had like a family session with — like a family dynamics coach, which is really interesting and the question came up of like what do we all care about? Actually, every one of my family all said that we cared about teaching.

[0:20:16.1] RN: What made you get a family dynamics coach?

[0:20:17.6] NT: I just thought I’d be interesting.

[0:20:19.4] RN: It was your idea to —

[0:20:21.2] NT: Yeah. I’m that guy. I’m that guy that’s like, “This sounds cool man, like self-development, family development. Let’s get more development.”

[0:20:25.8] RN: Got it. Everybody was there, like your brothers, sisters, parents.

[0:20:28.3] NT: Yeah. We had everyone there. At the time —

[0:20:32.0] RN: Was it related to business or was it just personal family stuff that you wanted to get sorted, or all of it?

[0:20:36.5] NT: It was partly related to business. It was partly of like getting clear on. Again, it’s a little difficult because in some cases my parents are the employees and in some cases they’re the owners of the company.

[0:20:46.4] RN: Yeah, I was going to ask you about that. Sorry. Just to interject. What was — You just jogged my memory. What’s that dynamic like? Obviously, your dad didn’t want to be on those meetings. He didn’t sound like that guy that really cares about the business management side. He just likes aviation, right?

[0:21:03.2] NT: Yeah, he loves it.

[0:21:04.1] RN: What’s it like, that relationship, in terms of — Do you boss him around or tell him what to do? What’s that like?

[0:21:11.3] NT: No. One of my styles is not being bossy especially not with him, because I’ll lose. But I think, again, it’s just this weird circumstance of I would — If it really was a point where like we had a real — Like we’re butting heads on something or even when my mom we’re butting heads on something, it was typically just a discussion. Maybe there’ll be a little bit of yelling because we’re Italians. Yelling is just part for the course, but it was never like a bigger, like, “Oh! We’re damaged and that we can’t be friends outside of this.”

Like I said, for the most part, it would just be like, “Hey, this is what I need from you.” Again, I’m just fortunate the way that they’ve been very vocal about the fact they appreciate me and they appreciate what I think and they trust me. They trust my judgment.

Really, it is a unique circumstance. I know the more I’ve talked to other family businesses, they’re like, “My dad won’t relinquish control, and he tries to set me up for success, but then he’s constantly stepping on my leadership and it’s breaks down the chain of command.” I don’t have that.

[0:22:04.2] RN: Yes. I think that’s pretty common within those types of business where it’s tough for the older generation to relinquish some of that control.

[0:22:11.9] NT: There’s times where sometimes their attitude, my parents’ attitude would be more of like, “I appreciate what you’re doing, but I’m not going to participate in it. You can do it, but that’s not my thing.”

I’ve had that happen from time to time where there has to be some sort of understanding. Actually, a friend of mine said, he’s like, “Instead of complaining about your family members and your business,” as a general statement he said, “Always just optimize around them as a creative constraint.” I actually like that thinking.

[0:22:39.2] RN: Yeah, it’s interesting. Back to the family dynamics coach, what were you hoping to get out of it and what did you actually get out of it?

[0:22:45.6] NT: I think the biggest thing I was trying to get out of it was just to make sure that there was a healthy understanding what everyone’s role is.

[0:22:52.7] RN: Within the business.

[0:22:52.8] NT: Within the business, and even within the family. It’s very hard for anyone to know what everyone else is thinking, right?

[0:23:00.7] RN: Is that just because you guys are — Are you a quieter family communication-wise? Obviously, you’re Italians, you can get loud. You can buttheads. Was it open communication typically or would you hold stuff in as an introvert and not express yourself like you should?

[0:23:15.2] NT: Yeah. I probably wouldn’t fully express. I don’t think any of us would fully express. Also, we were always talking about business. Rarely will we talk about the feelings behind that. I think in general we all wanted the same thing. We all wanted to take care of each other, and there was also like complaining wasn’t looked upon as a positive thing. We’re all just going to suck it up for the benefit of the family. We all kind of had a little bit of that.

With the family dynamics coaching, the thing — I actually remembered. The main reason why we had started with that. We ended up not hiring that one. We ended up using a different coach, but the main driver at the time was like where are we going with this business? Because that’s something we didn’t have clarity on. I knew how to maintain the existing structure of the business. That wasn’t that hard. I was like, “Okay. I see what we do. I’m just going to be in maintenance mode and be an editor.”

At the point when I brought that woman and I said, “You know, what do you guys want?” Because that’s where I’m stuck. If my parents own the business and I’m running it at the time, I was saying, “What do you want me to do? Because I can run it, but what for? Where are we going with this?”

[0:24:15.0] RN: You didn’t actually own any of the business at that time.

[0:24:17.0] NT: No, not yet. It was challenging because I was like, “I just need to know what you want. What do you want this business to be? That’s what I realized, that they don’t think on that level, and it was okay. My dad was like, “I like flying airplanes, so I got a plane.”

[0:24:29.5] RN: But he didn’t have a strategic vision for the business that we’re going to go from this to this and it’s going to be amazing big thing. It was just day-to-day.

[0:24:36.3] NT: Yeah. The most vision I could get out of them was a bigger version of what we’re doing. I’m like, “That’s not really very clear.” I had no direction and I didn’t have any vision for it. I don’t know what the hell I want to do. I was always like, “Wait a minute. I’ve gotten so accustomed to just trying to put the fires out.”

When the business got to the point where you didn’t need to put the fires out anymore, that’s when I got lost. That’s when I got screwed up. I was going, “Wait a minute. I’ve been a freaking fireman my entire life.” I’m like, “Oh, that’s broken. I’ll fix it.” “Oh, that’s screwed up. I’ll fix that too.” Now the company stabilize and everything is profitable and I’m going, “Shit! I don’t know what to do, because —”

[0:25:10.5] RN: Because you’re just reactive all the time.

[0:25:12.6] NT: 100%

[0:25:13.7] RN: Once there is nothing to be reactive about you’re just like, “Now what?”

[0:25:17.5] NT: Yeah. What the hell do I do? Do we make a bigger version of this? I realized that that’s — That’s why we ended up bringing this woman in and she said, “What do you guys ultimately want to do?” What everyone had said was that they all had the desire to teach. All of us love the idea of the teaching side, which is very much the flight school, not so much our charter domain.

[0:25:33.9] RN: Just for context. You have three primary business models, right? You have the jet charters, you’ve got the flight school and you’ve got the maintenance where you charge people to fix planes essentially.

[0:25:44.6] NT: Exactly.

[0:25:44.9] RN: Got it. Okay.

[0:25:45.3] NT: Exactly. With that, I got really clear on that. This is a very long winding answer to get to the point that, I know I want to do more around teaching and I know I want to do around coaching. I’ve done a little bit of coaching through Entrepreneurs Organization and some of the other groups I’ve been a part of and I just find that to be extremely — It’s fulfilling. It really gives you that deep sense of like in my belly I’m like, “This is where I can actually have an impact.”

I’ve thought about doing more stuff around that of either personal development using aviation as kind of a lens. I could talk quickly about an experience I had was, I was flying a single engineer plane, the engine quit. It was my selling moment.

[0:26:25.2] RN: How high up were you?

[0:26:27.7] NT: 3,500 feet, maybe 2,500 feet. Not very high.

[0:26:30.9] RN: High enough.

[0:26:32.3] NT: High enough. I’m here. It’s like the Titanic. It’s like, “I know how this story ends.” Actually, my dad was sleeping in the right seat because it was just single engineer plane. I’m flying, he’s sleeping on the way home from an event we were at. I wake him up. I’m like, “Hey, look. We got some interesting stuff to deal with.”

It was actually amazing because we were both so calm. There was just this moment of like — I didn’t argue with reality at all. I was like, “This is real now. Engine quit. There’s only one way out of this. We’re going to either land in a field or on a road.”

[0:27:00.4] RN: You’ve trained for this forever.

[0:27:01.9] NT: Yeah. It was like actually a no big deal. Then I was thinking like around the same time I had a string of pretty terrible relationships and extremely volatile. I’d wasn’t — I’d be like, “Oh! Why me? How did I end up like this bullshit?” It was like, “How is it that when I’m in a pilot’s seat I don’t argue with reality, but in real life I do?” It was years later than I thought about it. I said, “You know what? I learned how to overcome fear in a cockpit.” I really want to do something with that. I’ve thought a lot about taking a lot of that learning from the cockpit, a lot of that high-performance thinking and creating something where I could teach people about the best learning from the cockpit without them having to be a pilot to do it.

[0:27:37.7] RN: Very cool. Just based on that — I find that interesting that you’re able to be in that situation and just not freak out. What was it that — was it just literally the reputation and the hours of training that you’ve gone through simulators and you’ve flown that often? I guess when was the last time that you actually had to go through a simulation dealing with that kind of problem or you have engine failure? Because not probably not often, right?

[0:28:07.4] NT: We go to a sim every year.

[0:28:09.9] RN: Once a year?

[0:28:10.3] NT: Once a year we’d be in a simulator, but it’s from my youth too. It’s like just so deeply engrained in me. There are also different fear responses that people have. People have a natural tendency, like if someone pulled a gun on you, you just pee yourself. That does happen.

Other people, the gun gets pulled on, they’re just hyper-focused. I just happen to be one of those people that my stress response is like hyper-focus and no emotionality whatsoever. My dad is the same way. We’re like, “Let’s just go to solution. Stay in solution and not argue with the situation, because we’re just giving up precious time.” Obviously, it’s nice that I can logically say that, but that really was my fear response. It was just like, “No. Be focused.”

[0:28:52.7] RN: Could we do something cool?

[0:28:53.6] NT: Yeah. You want to pull a gun and put it on me?

[0:28:56.7] RN: I want to see you pee yourself.

[0:28:58.2] NT: Yeah.

[0:28:58.7] RN: No. Obviously, this is the Fail on Podcast. The whole idea is to push people to get outside their comfort zone and actually take action. You just gave me a beautiful laid out eloquent idea that you have that you want to implement, because you have a passion for it, right? For creating something, taking lessons from your life in aviation, being a pilot. I’d love to see you actually put something into action.

[0:29:27.2] NT: Yeah. It’s funny, I’ve started and I followed through. I actually spent — I’ve got all the content. I did a test run.

[0:29:32.2] RN: What? It’s not even like a conceptual theoretical thing. You’ve got content.

[0:29:38.2] NT: Yeah. I’ve got all the content. I’m at the point where I could write a book on it.

[0:29:41.5] RN: Let’s do the challenge. Let’s do a Fail On challenge where we’ll check back in and you actually launch this thing and then we can follow up and we can talk about it together. Are you in?

[0:29:50.2] NT: My stomach is twisting as you’re saying that, but sure let’s do it.

[0:29:52.7] RN: You’re in?

[0:29:52.8] NT: Yeah. it’s would be a good thing. It would be great to have.

[0:29:54.5] RN: Awesome. I love it. That’s the whole point of this whole thing is to make people have that pain in their stomach. Trust me, I got it before I interviewed James Altucher. I was like, “Aggh! I know if I can do this.” Just lean into it and you do the best, right? After I did it I was like, “I’m glad I leaned into that fear versus like ran from it.”

You’re in?

[0:30:18.8] NT: Yeah.

[0:30:19.5] RN: We can check back in, or do we want to give a time on this?

[0:30:22.8] NT: I’m going to go super long time horizon. No. I would say, realistically, I’d like to do it by the end of the summer probably because I’m launching a different program in the meantime and I want to try to use that as a template for launching my program. Yeah, by the end of the summer.

[0:30:35.4] RN: We’ll say end of August.

[0:30:37.7] NT: End of August.

[0:30:39.1] RN: Done. I love it.

[0:30:40.1] NT: Alright.

[0:30:40.9] RN: That’s how you do it. That is how you do it.

[0:30:44.3] NT: Man, I’m glad we did this.

[0:30:46.6] RN: You’ve had a lot of experience obviously within the family business and it sounds like you’re finally pushing yourself to do stuff outside of just that core business. I know we talked before this and you want to do a lot of innovative stuff within the current business, but out of all of the, I guess, struggles along your journey dealing with kind of the family stuff, dealing with the urge to do stuff that’s also more fulfilling. What’s been the biggest struggle along the journey just in terms of, I guess, struggles that you’ve had to deal with?

[0:31:22.0] NT: You’re talking about as far as balancing fulfillment, staying in the current business and figuring out what other places I want to play in?

[0:31:26.9] RN: Anything really. I mean, like you said, you just had that feeling in the pit of your stomach where it’s like, “Errr.” What else has caused you pain in terms of the business journey that’s been the most difficult to deal with?

[0:31:42.1] NT: I think I suffer from — It’s actually a blessing and a curse. I’ve been fortunate enough despite being a kid with massive social anxiety and fear of people, I’ve somehow managed to land in this incredible network of friends and just business relationships.

[0:31:59.1] RN: It’s not random though? We’re in the same community with Mastermind Talks. That’s a concerted effort. You must have had a part of you that’s like, “Okay.” You’re aware enough to know that you want to be surrounded by people that are doing cool things, right?

[0:32:13.7] NT: Yeah.

[0:32:14.5] RN: Have you always had that or was that something that —

[0:32:18.5] NT: No. That started in 2009.

[0:32:21.4] RN: Was that when Summit was?

[0:32:22.6] NT: Yeah. Summit kicked that off for me, and that was a total fluke.

[0:32:26.9] RN: Yeah, I don’t think you got to how you ended up at Summit.

[0:32:30.0] NT: Yeah. Let’s see.

[0:32:33.0] RN: Let’s hear it!

[0:32:34.0] NT: Alright. Fine. I had a friend that she was like, “Hey, there’s this program called Guest of a Guest.” It’s actually funny. Have you ever heard of Guest of a Guest? It’s like a website where they have people go to parties and they take a picture and it’s just like showing off, like cool people doing cool shit at events that I don’t get invited to.

[0:32:52.2] RN: You’re the guest.

[0:32:52.9] NT: No. No, I was not. Actually, someone just said, “You should check out this website. It would probably really good for you to promote your service on.” Because it’s a lot of like the high-end Hamptons crowd and all that kind of stuff. Actually, I meant to send a Facebook message to the founder of this because ultimately I sent an email just saying, “I’ll give you a helicopter ride to the Hamptons for free if you would broadcast on your platform that you did it with us.” She was like, “Yeah. Sure.” I’m like, “Alright. Cool. Let’s see what happens.”

I think they just felt bad when I greeted them out in the Hamptons. I actually flew myself out there to greet them when they got there and I think they felt bad like, “Oh, shit. Now we got to invite this guy the same thing.” They were like, “Oh, we’re going to this party tomorrow night. You should come to it.” I was like, “Okay. That sounds great.”

Again, I’m socially anxious. I still am. I still hate going to parties, but I get invited to this random Hamptons party. I don’t know anything about what’s going on. I’m told to dress Hamptons chic.

[0:33:44.5] RN: Oh, Hamptons chic. Of course.

[0:33:46.7] NT: What the fuck does that mean? I started having a panic attack over, “I don’t have nice clothes. I wear jeans and t-shirts.” I’m calling all the girls I know, I’m like, “Hey, what does this even mean?” They’re like, “Over-dress. Just over dress if you’re not sure.” I get dressed up in a freaking suit thinking like what else was I supposed to do? I drive all the way out to the Hamptons and I get out there and the guy who’s — He was the right hand of the founder. He doesn’t respond to me. I’m like sitting in a gas station for a half hour, like they never give me the address. They never give me anything. It was just brutal.

Finally, I’m starting to drive home with my tail between my legs. I just drove for an hour and a half. What an asshole I am. He’s like, “Oh, no. Come to this thing. It’s at the College Humor House. I didn’t know what College Humor was. I didn’t know any of that stuff. I get there and I’m talking to a dude at the party. First of all, everyone’s in t-shirts and jeans. I’m there and I’m freaking sitting like a dickhead. Like, I thought this was a Hamptons party? I don’t know.

I just looked for anybody that would talk to me, because again I’m like, “I don’t know. What’s going on here?”

[0:34:41.0] RN: And already social anxiety. It was just the worst situation. I’m the same way. If I go into a situation where I don’t know many people and there’s a big group of — Everybody knows each other. Oh, it’s painful.

[0:34:53.6] NT: Painful. Yeah. I talked to one dude and he’s like, “Oh, are you the helicopter guy.” We started nerding out about helicopters. I’m like, “I need to keep him the conversation, because I don’t want to talk to anybody else. Hold on to me buddy.” I’m like, “Hey, you want to go flying in Nantucket? You want to go to wherever?” Just anything to keep him in the conversation. “Yeah, I would totally do that. That sounds great.”

It turns out it was Josh from College Humor. I ended up taking him out, and actually, Ricky, went along for the flight and they took some people with them. It was awesome. We had this great time and I connected and I ended up catching up with Josh from time to time and ask him advice on stuff. He was like —

[0:35:27.5] RN: Josh is the founder of College Humor?

[0:35:30.0] NT: Yeah. He was the cofounder of College Humor. He’s like, “Hey man, you’re kind of a not like adventure type guy.” You should meet this dude, Elliot, who’s got this thing called Summit going on.” I’m like, “Whatever man. Sure.”

I meet Elliot and Elliot invites me to some stuff. I don’t know anything about networking —

[0:35:45.4] RN: Summit is not big at this point?

[0:35:47.0] NT: No. They haven’t done D.C. It was like a very —

[0:35:49.3] RN: This is early.

[0:35:49.8] NT: This is pre-D.C. time. This was like 2009. I get invited to meet Robin Hood, which I didn’t know what Robin Hood was and I’m meeting like Tiki Barber and all these people at this thing. I’m like, “I don’t know why I’m meeting these people. This has no relevance.” I said to Elliot, which hopefully he won’t mind that I’m sharing this. I said, “Look, dude. That’s great you got all these stuff going on. Just find two hot girls and come out to the airport and I’ll take you flying somewhere.”

That was it, man. He brought these two beautiful blondes out and we went to the Olive Garden in Connecticut. I was just trying to be ironic. I was like, “Let’s go fly to the Olive Garden.” From that he just kept inviting me to stuff and I would just visit them when they got the house in San Diego. I went and stayed out there. When they’re in Miami, I went and stayed with them.

For whatever reason, I just asked Elliot advice. He was a great leader as a young guy. It was unbelievable at that age to be so profound. They knew how to build a culture and build a group of people to follow him. I just asked him, “How do I be more like you,” which was weird because I’m significantly older than him. He was happy to give the advice and he would bring me to the events, and that was it, man. Once I was like in the Summit world I started to see, “Wait. This is what I need more. I need to be around people that are doing things that think more like I do that won’t just accept things as they are.”

I mean you want to talk about fear and failure? I was the most awkward dude. I still get weird around that crowd.

[0:37:05.4] RN: What’s the reason though? Because we could sit here and shoot this shit and have a good conversation, right? Is it just when you’re around people that are really successful or is it more about the big crowds where you don’t have any in or connection?

[0:37:20.2] NT: That’s part of it. Let’s be real for a second. I have a really hard time with the approach on hot girls. I never was good at that. I just had such a fear of rejection. Then I had a really hard time with super successful men. I was always like, “Why would they want to talk to me?” There was always that.

[0:37:36.4] RN: We talked about imposter syndrome a little bit, like, “Why am I here?”

[0:37:37.9] NT: Yes. There’s always a little bit of that imposter syndrome, which is why I think EO was so valuable for me, because I get to EO, and I’m like, “Oh, I don’t belong here.” Then I realized no one has a fucking clue what they’re doing. It doesn’t matter how many zeroes. You got people running billion dollar companies, like we don’t want to do next. We’re getting taken down by small startups that have this really innovative stuff and 17-year-old kids have figured things out.

It actually was more of like once I got that clear —

[0:38:00.2] RN: It’s like a grounding thing? These people are no different than me, right? Honestly.

[0:38:07.1] NT: It took me a while to get that. Even now though I still have remnants of that where I’m kind of like — I’m at Summit, but I’m not one of the cool guys at Summit. I’ll play the guitar so people like me.

[0:38:17.9] RN: I’m ready to goof around. Yeah.

[0:38:19.5] NT: What do I got to do to be cool? I think I just always kind of have a little bit of that baggage, but that’s actually been the hardest journey for me I think is the social side and realizing that I’m not weird. I just think I’m weird and I think I’m being awkward, which then makes me act awkward and be like, “Dude. What is your deal? Why are you being so strange?”

I don’t know where to go. See? Now it’s awkward. Now it just got fucking awkward. I got nothing else to say.

[0:38:44.7] RN: You want to know what’s awkward, is — this is brutal, because I told you I was really nervous going to talk to James Altucher for whatever reason. I don’t even know why. I just built it up my head. It was a normal — I think he’s a nerdy dude. He’s a nice guy and very approachable. I don’t know why I built it up my head, but I started off the interview. We’re going along and he’s like, “That’s a great point, Ron.”

[0:39:13.4] NT: Did you correct him?

[0:39:14.8] RN: I’m like, “Who is Ron?” No I didn’t correct him, because I would have —

[0:39:19.5] NT: You would have felt like an asshole.

[0:39:20.3] RN: I would have felt like an asshole. He keeps doing it, right? It’s once. It’s like throughout the whole interview. He just keeps calling me Ron. Talk about awkward. At the end I was like, James, it’s Rob. He felt really bad. I get it.

[0:39:36.8] NT: You probably felt worse than he did.

[0:39:37.7] RN: Yeah. I was like, “Dude, I couldn’t even be memorable enough for him to remember my name at the beginning. I don’t know. I put it on myself a bit.

[0:39:46.5] NT: I have a funny story about him specifically. Remember when I told you that my wife is the most confidence human being on this planet? We’re out at Mastermind Talks and she sees James sitting there and she knows him from this — She gets his emails or whatever. She’s like, “Oh, James.” And she goes and sits with him and has an hour-long conversation with him. I’m like, “I couldn’t even approach him. I couldn’t even approach him to say, “Hey, dude. It would be great to know you.” She’s like, “Oh, James Altucher. I’m going to go sit and talk to him for an hour.” Like, “Holy shit!”

[0:40:12.6] RN: That’s like one of the craziest super powers to for people is like that they could just do that seamlessly and not blink, because it seems like we’re cut from the same cloth where we had a lot of mental issues to overcome that you can have a freaking conversation with somebody. Which is good for me doing this podcast, because it pushes me outside my comfort zone which embodies a whole damn thing I’m trying to do with Fail On is embrace fear and embrace failure.

[0:40:36.8] NT: I’m curious how this works out for my brand, my personal brand, like, “Oh, I didn’t know Nik was so fucked up.” “It’s going really well guys.”

[0:40:46.0] RN: Yeah. This definitely won’t be the promo for your personal brand. I’m going to have to burry this in the podcast archives so nobody sees this.

[0:40:54.1] NT: Exactly.

[0:40:56.2] RN: I saw you post on Facebook, it was about this adventure trip. I was like, “Oh my God! This is like my dream come true trip,” is you just — You threw out an invitation, “Hey, who wants to hop in my airplane? We’re going to hit 5, 6 different cities, stay for a couple of days.” What was it? No more than 24 hours, no more than 48 hours or something?

[0:41:16.4] NT: Yeah, you don’t’ stay more than 24 hours, and you can’t plan 24 hours in advance where you’re going next.

[0:41:22.2] RN: I love airplanes. I love spontaneity. That intersection of those two is my dream come true. Why don’t you tell us more about this and what made you come up with it? Is it a business society? Is it something you do for fun? What’s the driver behind it?

[0:41:39.4] NT: I’m torn on whether it’s really a business. I’m working on building a small version of it. We actually launched it as a test last fall. The origin was this, mastered flying at a very young age. Got super bored and I was like, “Alright. I’m doing stunt flying now. I’m basically trying to rip the wings off the airplane to give myself any kind of thrill.”

Then later what it became was maybe I just need to share the experience a little bit. I’ve always heard someone, they say when you give back that’s when you really get [inaudible 0:42:07.3] I feel fulfilled. I just started inviting random friends to come on flights and what I noticed is when I would take off I’d look to the right and I’d see this face of awe and just total wonder.

[0:42:16.9] RN: So true. That was my face.

[0:42:18.9] NT: [inaudible 0:42:19.2] fired and I was like, “Wow! I’m happy again.” I’m so glad to be able to share this people. Then I said, “Let me take this to the extreme. Let me go on Facebook and just crowd source to go on trips that I don’t know well.” I’m a Facebook whore. I’ve got friends that I — Friends, I just met them once. I was like, “What’s your name? Cool! You’re my Facebook friend now.”

[0:42:36.2] RN: It’s part of that insecurity, right? It’s like, “Yeah, I got more friends.”

[0:42:38.1] NT: Yeah, exactly. I may not really have friends in lie, but thank God I have 3,500 people on Facebook. Yeah. Whatever. No one is buying it. I actually have great friends. Just in case they’re listening, they’d be like, “What a dick! What the fuck? Do I not count?” No. I love my friends. They’re really great.

What ended up happening was that I crowd sourced and just put a random message that was like, “Hey, who wants in, doing a nine day adventure? Don’t know what’s going on?” I got like the host of the bachelor from Australia, or Australian bachelor. However you say that. I got my friend who is —

[0:43:10.3] RN: How did he —

[0:43:11.5] NT: I met him at Summit once.

[0:43:12.8] RN: Okay. You knew him.

[0:43:13.7] NT: Not really.

[0:43:14.5] RN: He was a Facebook friend.

[0:43:16.1] NT: Yeah, it was like a one-time thing. Yeah, it was like people I didn’t know well.

[0:43:17.9] RN: He’s like that dude.

[0:43:18.7] NT: I’m like other people invite other people along. I had a couple of friends that I was close to, but it was really this pretty profound experience where I would do stuff like that and realize, “Here’s six of us on an airplane.” You got to check your ego at the door because everyone else is like, “I’ve got no control of what’s going on. I’m going negative. They’re floating off the seats.” They’re like, “Shit! This is pretty real.”

By the end of the trip I noticed that there was this crazy acceleration of relationship building, because you’re like, “You ever heard like in like Pick Up Artist, they talk about, “Take a girl to three locations over the course of a night. It feels like she knows you more.”

[0:43:48.9] RN: I don’t read Pick up Artist. Sorry, Nik.

[0:43:51.4] NT: Come on. Everybody read The Game. Did you not read The Game?

[0:43:54.3] RN: I think I probably I did. I probably glanced at it.

[0:43:55.2] NT: Yeah, everyone likes Neil’s book, right? I think they were talking about it and they’re like you move people to different locations. I never did that in dating, but I did it in the airplane, because I was like, “Let me take some over three days or whatever and move them through three different cities.”

You end up having these crazy, like this crazy memory of like, “Oh, that person have been to Boston and Bermuda and North Carolina.” You suddenly feel like, “I know you better than I thought I did,” and the only constant is the people on the plane. Everything else is changing constantly. People are holding on to each other, really embracing each other for the experience. I was like, “Wow! For a guy that’s socially awkward, the highest currency I can think of it is connection,” right? Like real depth of connection. I was like, “Wow! This is like a drug to me. I love the idea of having this kind of vulnerable connection with people and true friendships coming out of these things.” I just kept on doing that, I kept doing that. I was like, “Wait, maybe this is a business.”

I ran a test — sometimes I just think I’m an idiot. I’m really like — For a smart guy, I’m often stupid. I’m like, “Well, I’d love to scale this,” and for years I said I’d scale it. Then it wasn’t until last fall that I was like, “Oh, wait a minute. I have a flight school and renters and maintenance customers that own airplanes and fly.”

[0:45:03.7] RN: All the ingredients you needed, right?

[0:45:04.2] NT: I have everything I need to build this damn thing. Why did I completely just disregard all that? In November I actually built an experience and got a bunch of people to come on it and said, “Hey, look. If any of my entrepreneurs friends want to go, they can connect with any of the pilots that are going and legally you can share the cost with the pilot, because that’s on charter.”

We did it and, again, one day, we had a one day adventure. It was awesome. It was super accelerated and by the end of it my customers — two of my customers that went — By the way, only two customers that went [inaudible 0:45:35.6] were the ones that were like, “This sounds like bullshit, and I like flying to fly. I don’t need all these bullshit on the ground.” I’m like, “Oh, this is giving me a nightmare.”

By the end they were like, “I haven’t felt that kind of connection. I haven’t had an experience like that since I was in college.” One guy was like — these are lifelong friendships that came out. You could really feel that connection. It’s so authentic. I want that to be something. I have a dream of doing some bigger stuff that I won’t mention yet, because then you’re going to make me do it in three months or some shit.

[0:46:03.5] RN: Yeah, you got to be careful. Your business side is around here.

[0:46:06.5] NT: Yeah.

[0:46:07.4] RN: That one day adventure, what was it? You didn’t say overnight anywhere, but did you go to three locations or multiple locations in like one day?

[0:46:12.9] NT: For this one, no. We flew to New Hampshire, to Lebanon, New Hampshire which is right near — I’ll tell you the itinerary. We flew up there. We had — Five planes went. We think we had a total of like 12 people. Immediately, we went to Simon Pearce Restaurant, which is this really cool restaurant, perched on the top of a waterfall. They have a glass blowing studio in the basement. Everything is locally, organically, crazy good ingredients. Already, people were like, “What the hell is this?” There’s a unicorn flying by the window or something. It’s just magical.”

Then we went over to a Raptor Park, which is like eagles and hawks and falcons and they actually were recover these birds. One of our guys called the headset, “We got a bunch of pilots coming to Raptor Park.” It’s like, “Oh, we’re going to do special stuff for the pilots.”
We get there and there are like flying hawks over our heads, like the wings are touching our head and stuff. It was amazing.

[0:46:59.6] RN: It’s like a sanctuary for —

[0:47:00.5] NT: Yeah, it’s like a sanctuary for these birds and owls and all that kind of stuff. Then they were like, “Oh, for the pilot group only. We’re actually going to go release an owl back into nature. We’re going to drive you guys down to a field and we’re going to release it.” I was like, “That was awesome.” Then we went to a gorge and took a view of this beautiful gorge that they have. Then we went to this old town. Actually the Rockefellers are actually pretty influential in this community and the Billings family, which were like big banking in the 1800s.

It’s like this beautiful old New Englandy town. We go just hang out, grab some food. Went to some hippie restaurant where it’s literally like — It makes me think of like — How is that movie called? I think unicorns are kickass, man. Did you ever see Basketball? Basketball or something?

[0:47:41.9] RN: Long time ago. Yeah.

[0:47:43.1] NT: Yeah. It’s like the tie dye shirts. It’s like, “Yo, bro. It’s like crazy time here.” There’s just like these dudes making the most amazing chicken. I’m like, “I didn’t know you guys are good chefs. I just know you’re a bunch of dirty hippies.” It was just this amazing experience that was really outside the comfort zone of most people. They are Long Island guys that go to nice restaurants. Here we are like it’s a hippie restaurant in Vermont. During the time I’m like listening to the conversations that are coming up and it was like real stuff.

[0:48:09.3] RN: So you’re more of like a curator, right? You’re kind of just putting together — a connector. You brought all these guys together and you’re kind of just — you’re in it, but you’re sitting back a little bit looking from the 30,000 foot view. Just seeing like how it’s all flowing, how the conversations are going.

[0:48:24.6] NT: Yeah. Actually, during the first lunch I thought I’d like need this big plan to create this and I just fueled this basically one question and then everyone just went. I was like, “Say who you are without any external characteristics, whatsoever.”

[0:48:39.1] RN: Like what business you’re on or —

[0:48:41.1] NT: You can’t say what you do. I’m like, “Who are you by essence? What is it?” It was just like no one knew what to say. Then people started to really share with real stuff and that was it. The day was set in motion.

[0:48:52.8] RN: That’s a great ice breaker. Ice breakers are stupid, I think, but I think if you can take away a person’s identity based on what they’ve accomplished or what they do for a living, get to the heart of the matter really quick, don’t you?

[0:49:08.9] NT: Yeah. I’m telling you, people had a hard time answering it at first. Then they just started getting into their feelings and really the deep identity that they have for themselves. It’s very cool. That was it. If the conversation gets off the rails I would just gently kind of steer it back, but it was pretty magical.

[0:49:27.2] RN: That’s awesome. What’s your ultimate goal with it? What’s your vision for it? I know we’ve talked about your dad, didn’t have a vision for your fly company, but what do you — I know you’re different. You have big ideas. You are looking to do cool stuff. What’s your ultimate vision with that?

[0:49:44.4] NT: This is the thing. I do have a great appreciation for aviation and I think that we as industry have done a terrible job of promoting it to people. Even you say, you’re interested in being a pilot but you’re not doing it. It’s like, “How can I get you to want to be a pilot?”

[0:49:59.8] RN: I’m so close to where I would do it.

[0:50:02.0] NT: That’s what I’m saying. How many people —

[0:50:03.0] RN: Nobody is nudging me.

[0:50:04.1] NT: That’s what I’m saying.

[0:50:04.4] RN: If I had somebody like holding a flame to my ass I would do it in a heartbeat.

[0:50:09.4] NT: Alright. Fail On challenge. Let’s do this thing. Let’s do this Fail On challenge.

[0:50:12.9] RN: Hey, you can’t turn the table here.

[0:50:14.5] NT: Okay.

[0:50:16.7] RN: I am close. It wouldn’t even be for your benefit, because I wouldn’t come here to do your flights.

[0:50:22.4] NT: But it is my benefit.

[0:50:23.2] RN: Why? Just because it’s a —

[0:50:24.3] NT: The industry wins, right? I know I shouldn’t — My profit is going to go necessarily, but, shit, if you’re another pilot, maybe I’ll be like, “Hey, we’re doing this flight event right at New York. You’d come rent one of my planes and bring some cool people along.” Everybody wins. Where you’re like, “Nik, I want to buy a plane someday.” You never know.

[0:50:38.3] RN: Yeah. I know we talked — Because I’ve mentioned this when we’re starting to sit down and munch on some chicken tikka masala that I was thinking about it at one point. You made a good point. Would you mind sharing?

[0:50:50.6] NT: Like the reasons to be a pilot?

[0:50:52.4] RN: Just connections.

[0:50:53.8] NT: Yeah. That’s what I’m saying. Actually, I have a book coming out soon so I’ll plug myself. I don’t even know what it’s called.

[0:50:58.9] RN: Shameless plug.

[0:50:59.1] NT: I don’t even know what it’s called yet.

[0:51:00.5] RN: But you’ve already written it?

[0:51:01.2] NT: Pretty much. It’s just in editing right now.

[0:51:02.6] RN: Got it. Cool.

[0:51:03.5] NT: Part of it was I realized like all these people, all these entrepreneurs come to me and they’re like, “Dude, I want a plane.” Like, “Okay. Get one.” “You want one go get one then. What’s the problem?” “It’s so expensive. I’m waiting ‘till I make my millions.” I’m like, “Well, once again, aviation just blew it with the messaging.” Everyone thinks it’s so expensive and it’s just unreachable.

Part of the concept of the book was just debunking – like it’s so cheap to buy a plane. You could buy a little four-sitter for $30,000.

[0:51:34.1] RN: Please release this book.

[0:51:35.5] NT: Yeah. I’m telling you. It’s the whole roadmap for what it means to buy your own plane.

[0:51:37.5] RN: Please release this book.

[0:51:38.6] NT: The whole premise though was like it’s not enough to say you should have your own plane and here’s the numbers.

[0:51:42.3] RN: Back to the book. Stop what you’re saying. Back to the book. When is it being released?

[0:51:47.6] NT: I think I’m like two months out.

[0:51:49.8] RN: Okay. Now, you can continue.

[0:51:50.5] NT: Yeah. That was fun. More of what I wanted to — I started the book out that was really getting to like, “Here’s why you should be a pilot,” because no one tells you that. Everyone thinks you should be a pilot because it’s awesome. Yeah, that means nothing to anybody. What it really comes down to is whatever you care about — airplanes are a multiplier of that. Anybody in business knows that it really is the relationships you have. It is your network. If you want to get someone on your plane, if you want to get an hour with someone, you want to get a committed, dedicated, focused hour with a person that you care about, Then invite them to come to dinner or lunch in another state. You fly them there. Their Wi-Fi doesn’t work, the phone doesn’t work.

[0:52:27.3] RN: You have to talk to me.

[0:52:28.2] NT: They’re sitting upfront with you. You know what? You gave them an experience that they’re probably never going to forget. Again, as long as you’re like good about it.

[0:52:34.1] RN: What kind of plane are you flying? Are you flying like a little single engine? Are you flying — What kind of —

[0:52:38.8] NT: All the above. I typically will fly a small plane, and the reason is this, it’s cool to go on a gulf stream. Again, you’ve done it with Jet Smart and that kind of stuff. It is cool, but it’s not that different from the airlines. It really isn’t.

[0:52:52.6] RN: It’s actually worse, to be honest.

[0:52:54.1] NT: You’re isolated. You don’t really know what’s going on. You could sort of see outside. When you’re in a small plane you have the full panoramic. They can work the controls. They can see what’s going on. It’s a real experience for them. They’re like, “Wow! This is a whole different way of being and living.” That’s what I really wanted people to get is like, “Hey, my —” Part of it is like I want to be friends with people and I want to have real connection. Part of it is like I also want — If someone walks away from the plane going like, “Wow! I don’t actually want to be a pilot, but what else is possible in my life that I’ve been writing off as impossible because of logistics or whatever it is?”

I think that that’s really kind of the underlying thing, is build amazing relationships. Have this — Again, it’s like I could go to little islands that people don’t even know exist. I can get there real fast. If I told you the money you’d be like, “You got to be kidding me.”

[0:53:37.9] RN: What? It’s cheap.

[0:53:38.8] NT: Like Nantucket. Let’s say I want to go to Nantucket and I want to take some friends there for dinner just to really give them a wild experience. My plane, it’s about an hour each way. It’s actually a little bit less. I burn 12 gallons of fuel of each way. The fuel is $5 a gallon, so it’s 60 bucks each way. Parking is $20. What is it? About 140 bucks?

[0:53:58.5] RN: Yeah, transportation.

[0:53:59.8] NT: What’s that?

[0:54:00.4] RN: You said for transportation.

[0:54:01.3] NT: All in.

[0:54:01.9] RN: Yeah, all in.

[0:54:02.4] NT: My cost with fuel and parking, all that stuff is $140 for four people.

[0:54:09.0] RN: Four-seater plane?

[0:54:09.5] NT: Yeah. Again, if you rent a plane, it’s a little more. If you rent a plane, maybe it’s $150 an hour of actual flight time. Still, you’re not talking about a lot of —

[0:54:15.6] RN: You’re saying, because you own the plane.

[0:54:16.6] NT: Yeah. Either way, you’re talking about hundreds of dollars to have what would seem like a million dollar experience. You’re creating like a million dollar lifestyle.

[0:54:24.0] RN: I only have mutual friend, with Jason Gaynard.

[0:54:26.8] NT: Yeah.

[0:54:29.0] RN: This is also Mastermind dinners, right? It connects all these super successful, high-level business owners and you’re saying, “Yeah, obviously that’s super valuable,” because what we’re talking about right now is connection and networking. You’re saying take that model. It’s not like a 10 to 12 Mastermind dinner. That’s how many people they usually have at a dinner, but moving it down to four people, putting them in a confined space in a plane and taking them to a dinner in a cool location. I love it.

[0:54:55.4] NT: Yeah. Again, for me it’s not profitable right now because I’m not doing it as a charter flight. I’m really doing it as like, “Let’s just share cost.” I think — My ROI is massive. I’ve got some amazing friends in my life that have given me great business ideas and things like that.

[0:55:08.1] RN: Which brings me along the lines of — You run a jet charter company, right? Who are some of the most amazing people you’ve met just through that? I’d have to imagine. In New York, in the New York area, you’ve got to have some pretty interesting people going through your business.

[0:55:23.1] NT: Yeah. I don’t need to know, because I’m not flying the plane, right? Even if am flying the plane, it’s not that kind of relationship where a lot of the customers don’t want to hang out with their pilots or talk to their pilots. Either way I’ll lose. Either way, it’s like, “I’m the pilot.” They’re like, “Just fly the plane. Let me do my thing.”

I haven’t met that many people through the charter business itself. We do have some great customers that I’ve met that are kind of standout. They really have been just wonderful human beings.

[0:55:46.2] RN: That people would know?

[0:55:47.0] NT: No one I’ll share.

[0:55:48.5] RN: Sure, but people would recognize their name.

[0:55:50.2] NT: Yeah.

[0:55:50.8] RN: Okay.

[0:55:51.1] NT: Yeah.

[0:55:51.6] RN: Why won’t you share them?

[0:55:53.0] NT: It’s out of respect.

[0:55:54.8] RN: Yeah. No, I get it. I get it.

[0:55:55.8] NT: It’s out of respect. From that perspective —

[0:55:58.2] RN: A jet charter company is very high touch and high personalized and their relationship is everything.

[0:56:02.9] NT: Yeah. If you remember there was, I think, on a charter flight someone had filmed Michael Jackson at one point and they released the video of him flying on their jet. It’s like — Man, it’s just death. What are you doing? People pay to not have to deal with this shit and then you’re going to exploit them? It just doesn’t make any sense.

[0:56:18.2] RN: Obviously, you talked about the adventure trips which do you have one planned? When is the next one?

[0:56:24.4] NT: I think I’m going to be doing one in May up to Toronto actually to go visit a lot of the Mastermind Talk’s guys. I’m thinking of doing like a two-day trip for Toronto and then Niagara and back. That’s in the works. I’m just working on dates for it. Because, really, my constraint are the pilot availabilities. I’m looking to see when pilots are going to be available. It’s an interesting model. I’m hoping it turns into something. I don’t know how committed I am to it yet.

[0:56:45.7] RN: Sure. It’s more of like a fun.

[0:56:47.4] NT: Yeah, it’s a passion project and I’m kind of like I don’t want to offset the main business for this.

[0:56:51.1] RN: Even if you could breakeven on that, it’s just is like a passion project. If you bring in people that you don’t necessarily know, like your Facebook friends, like you don’t know who they are. You get thrown off on Facebook, have people reach out that you don’t know basically, but that are interesting.

[0:57:05.4] NT: Yeah.

[0:57:07.1] RN: The ROI on these relationships are huge even if you just breakeven on the actual financial aspect of it.

[0:57:12.6] NT: Yeah. I think more of the challenge is that I don’t feel I’m ready to tie up my company’s resources to run this, so that I do it myself, because I’m like, “Well, there’s big projects going on with Ventura. The last thing I want to do is to like, “Let me pull away my admins and some of the other team to do it.” I do it myself and I don’t like coordinating. I actually don’t like calling people —

[0:57:31.7] RN: You don’t like the logistics.

[0:57:32.5] NT: Yeah. I can’t stand it.

[0:57:33.6] RN: Got you.

[0:57:34.8] NT: I feel that that’s not where I play.

[0:57:36.0] RN: Yeah. Fair enough. What are you most excited about moving forward?

[0:57:41.8] NT: That’s a good question. I think the number one thing right now, it’s not any particular project. What I’m most excited about is — again, we talked a little bit about the fact that I did a Landmark. I think because of the way I grew up in the industry —

[0:57:56.8] RN: Just for context. People don’t know what Landmark is.

[0:58:01.9] NT: It’s like a personal development course that you just get some clarity around how you’re showing up and stuff like that. When I did the Landmark work, what really came out of it for me was the amount of negativity I carried for my industry. I actually went back and looked at it and the reason is I’ve grown up around aviation people. Aviation people —

[0:58:23.6] RN: All jaded or what? What’s the —

[0:58:24.8] NT: Not all jaded, but many. Aviation has this pattern of swallowing people whole and just leaving them with nothing. That’s why like people say you want to make a million in aviation, start with five.

[0:58:34.6] RN: Is that why there’s also that negative connotation around like, “Oh, it’s so unattainable to own a jet or a plane.”

[0:58:40.2] NT: Yeah, because people make — You know what? It’s a passion industry. You make a bunch of money and you’re like, “I don’t know, man. I want to own a jet. I just want to own a jet.” There’s no shortage of people who want to take advantage of that guy with a bunch of money who wants to buy a jet.

I think that those are the stories that get shared or the stories that didn’t go well. I had a lot of negativity. I had this dialogue; “you can’t make money in aviation, you can’t make money in aviation, you can’t make money in aviation.” I believed that at some point I’m like, “It’s true. How the hell am I ever going to do anything?” It kind of became self-defeating.

With the work with Landmark, I really kind of got a clarity around the fact that, actually, I’ve had so many opportunities sitting right in front of me that I just couldn’t see because I was too busy complaining and I was too busy feeling sorry for the circumstance I was in.

I think what I’m most excited about really is actually just looking at my current circumstance in Ventura and the other opportunities that I’m facing with a new set of eyes and with the eyes of like, “Where’s the opportunity here?” Because I actually think it’s good that everyone is complaining. That gives me a room. That gives me a room to maneuver. If I’m the one who sees possibility in everything then I’m going to win in the end. Even if I don’t win, I’m going to learn a lot. Really, at the end of the day we’re all going to die.

[0:59:47.6] RN: That’s the whole idea, right? Yeah.

[0:59:48.1] NT: I just want to have a fun ride, learn a lot. I get to fly airplanes. It doesn’t suck that bad.

[0:59:52.5] RN: Life could be worse.

[0:59:52.9] NT: Exactly.

[0:59:53.6] RN: Cool, man. I don’t want to take any more of your time, but thank you so much for hosting us here in your New York City apartment.

[0:59:59.0] NT: Absolutely.

[1:00:00.2] RN: We’ll have to get some more chicken tikka masalas soon.

[1:00:02.7] NT: Fantastic.

[1:00:04.1] RN: But I’m not letting you off the hook, because you accepted the Fail On challenge, so —

[1:00:10.1] NT: I should make it conditional on you becoming a pilot.

[1:00:12.5] RN: You should, but I’m going to end the podcast too soon for that to happen. Alright. Thanks, man.

[1:00:18.4] NT: Cool.

[1:00:21.9] RN: Alright. You could find Nik @nikterascio on Twitter, that’s @nikterascio. Of course, for that spelling and the links and resources Nik and I discussed including more information on his YouTube channel and aviation company, that will all be found at the page created especially for this episode. That will be at

Next week we’re sitting down with my good friend, Clay Hebert. Clay is a crowd funding genius and the creator of The Six-Word Intro. I spent a fair amount of time with Clay over the past year or so and he’s one of the most absolutely well-liked people I’ve ever met. Everywhere we go people will just love this guy, but he’s endorsed by Tim Ferriss as the crowd funding guy. It’s a great episode, and it teaches you how to start a business with essentially no risk. Don’t miss it.

If the podcast has the wheels turning a bit, please email me at and let me know what your biggest struggle is in getting started or breaking through to the next level. I respond to each email personally and would love to learn more about your business and where you’re at.

As I continue to build Fail On with the goal of helping people embrace failure, share their struggle and decide once and for all to create change in their lives, I’d be really grateful if you could help me out. Subscribing to the podcast takes a single click and helps the show simply get found my more people. When people can find the show it means it can help more people, which in return means you are helping more people by simply subscribing. To subscribe and rate and review the podcast, super simple, just visit or


[1:01:42.1] ANNOUNCER: That’s all for this episode of The Fail On Podcast. For more resources, show notes and action items to help you find success in your failures, sign up for our mailing list at For more actionable inspiration, we’ll catch you next time right here on The Fail On Podcast.


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