Founder's Story - The Future of Flying: What Elite Travelers Want (And How JET365 Delivers) | Ep 216 with Alessandro Figliano Founder of Jet 365

Episode Date: May 9, 2025

Alessandro Figliano, Founder & CEO of Jet 365, shares how he turned a love for flying into a luxury aviation brand trusted by F1 and high-net-worth clients. From flying school to building a white-glove charter service, Alessandro breaks down how Jet 365 blends safety, personalization, and tech into an experience the new generation of elite travelers demands—while maintaining the service standards legacy brands lost.Key Discussion PointsPilot to Founder: How Alessandro funded flying school through his first business, then transitioned from hobbyist to charter operator.Seeing the Gap: Why a fragmented broker space inspired Jet 365’s concierge model—tailored for both tech-savvy users and traditional luxury clients.F1-Level Partnerships: How a personal network led to Jet 365 becoming the aviation provider for a Formula One team.Luxury that Listens: The power of referrals, retention, and saying yes—even when a plane breaks down hours before takeoff.High-Touch Meets High-Tech: How Jet 365 is building a new platform to serve both automated and white-glove clientele.Custom Over Scale: Why Alessandro rejects fast growth in favor of sustainable, service-first expansion.Key TakeawaysSolve before you scale: High-end clients don’t care about volume—they care about flawless delivery.White-glove wins: Luxury is less about cost and more about care. Every detail matters.Two types of clients, one standard: Whether booking online or via concierge, experience must exceed expectations.Build in public (quietly): Real partnerships and growth happen behind the scenes, not on Instagram.Sustainability > speed: Growth that protects service levels will outlast shortcuts every time.Our Sponsors:* Check out Indeed: https://indeed.com/FOUNDERSSTORY* Check out Northwest Registered Agent and use my code FOUNDERS for a great deal: https://northwestregisteredagent.com* Check out Notion: https://notion.com/founders* Check out Plus500: https://plus500.com* Check out Rosetta Stone and use my code TODAY for a great deal: https://www.rosettastone.com* Check out Square: https://square.com/go/founderAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

If you're anything like me, your inbox is a mess. I used to spend hours sorting through emails trying to find that one thread or task buried under a mountain of newsletters and noise. I can't stand it. That's why I started using Notion Mail. And honestly, it's been one of the most game-changing things that we have done.

Notion Mail is the inbox that thinks like you, automated, personalized, and flexible to finally work the way you work. With AI that learns what matters to you, it can organize your inbox, label messages, draft replies, and even schedule meetings. No manual sorting required. It actually connects with the rest of my workspace, so my messages, tasks, and notes are all in sync. I've never felt more on top of communication. Get Notion Mail for free right now at Notion.com slash founders and try the inbox that thinks like you. That's all lowercase letters Notion.com

slash founders to get Notion Mail for free right now. When you use our link, you're supporting our show Notion.com slash founders. Welcome to It Takes Energy presented by Energy Transfer, where we talk all things oil and natural gas. Oil and gas drive our economy, ensure our country's security, and open pathways to brighter futures. Did you know that the majority of progress the U.S. has made in reducing emissions over the past decade has come from the oil and gas industry,

with more electrical power generation now coming from natural gas versus coal, the air we breathe today is cleaner than it has been since the 90s, according to a report from the EPA. Clean burning natural gas is also a reliable source of power for more than just our electrical grids. It is also used to power data centers, hospitals, schools, and so much more.

Look around, and you'll see the essential role oil and gas plays in our lives. Our world needs oil and gas, and people rely on us to deliver it. To learn more, visit energytransfer.com. Hey, everyone. Welcome back to Founder's Story. Today we have Alessandro Filiano, the CEO and founder of Jet365. And Alessandro, I'm very interested to learn about the luxury aviation space, how you're

disrupting this whole industry and all the things. I know you got some crazy partnerships coming up. We were just talking you were at F1, I mean this is gonna be jam packed today, but 365 is a global luxury aviation company based in the US, dedicated to transforming private air travel, which a lot of the people I know are going to that versus the normal commercial,

but Alessandro, what was the spark for entrepreneurship and why this industry? Yeah, I'll tell you, I've always been like an entrepreneurial spirit. I always had a passion for private aviation, never had the money to do it. My first company did pretty well. Put myself through flying school

and I became like a fully licensed commercial pilot all in one year. I was, I got introduced to, it was a flying club and we would fly all around the world and I got a lot of experience and connections and what happened was I had a lot of people asking me, hey, can you fly me for money for this and that? I said, guys, I don't have any AOC. I can't just fly you for cash. So I started facilitating a lot of charter ops and sending business to a lot of other brokerages. So eventually I said, you know what?

Let's become the brokerage, let's do this. And then that's how the business got started. So kind of just fell into it, but we've been off to the races. Let's go back to that in the beginning. So you get going, you create this, you know, the official company and then what? How do you gain, you know, the first 100 customers?

Oh, I mean, we don't even have 100 hundred, uh, full-time flyers now. I mean, it's very, uh, smaller numbers than that. We deal with like very high net worth individuals and kind of provide a very personalized service, but I mean, we do have one-off clients all the time. Come in. We're very strategic in our approach with providing a very high touch personalized service. And, and yeah, we just want to separate ourselves from the other competition I know there's a lot out there but you know our

main three factors is safety service and flexibility so we want to make sure that we provide you know a different service than the rest and safety is our number one concern and service yeah. So what types of people do you find that are more attracted to this this form of travel versus going to you know your normal like commercial airlines? I mean I think it's the entrepreneurs it's the guys that value their time I mean time is money it's important to get around efficiently and you know these guys they value their time they want to be home with their families after the end of a long workday

and they probably have like multi-location businesses so I mean it's it's really good to get around for them and the service is needed and we're finding it a lot with the Formula One team as you know. We just announced that partnership, very excited about that and they came to us, right? They needed our service so we're excited to be working with them and facilitating all their stuff as well and stream mining stuff. It's amazing in business how sometimes you have someone who is your customer client who has a need and then you build something bigger on top of that. Can you tell us about that partnership? Yeah well the partnership it came through a good friend Oliver Oaks and we they reached out because they needed the service they didn't have an aviation provider and they needed they needed the service to just get around the logistical challenges around F1 are insane. So they just needed someone they can trust and

through the grapevine and they know about my service, they reached out and we were able to put a deal together and you know facilitate that stuff for them yet. So a lot of people would think of this like how the heck do you put all of this together, right? Like you had some experience in the space, but not a huge amount when you started. So I think a lot of people are like, they don't know how to get started. What was something that you did or something early on when you get into a new industry that allows you to get started and then start seeing success? Well, I think we noticed early on that there is a it was heavily fragmented. There was a lot of

disconnection and the way of booking a private jet was completely fragmented So we wanted to streamline that and with a new platform coming out We're gonna be able to do that and that's what the new generation. We're seeing a notice Switch if you will of a user experience where they just want to completely automated They want to see the options they want to book and then we have the old-fashioned client which we have a lot of them where they want everything you know handled through us and a very back and a lot of back and forth and you know it's it's two different customers but I saw a need for it a lot of learning lessons a lot of

mistakes but you know we're we're feeling very comfortable now and we're two years in and we've been off to the races and providing some really good stuff for our clients. So how do you look at this white glove service? I imagine the more the higher net worth individual or higher net worth clients that people have with whatever company, they're going to expect this type of white glove service. How do you ensure that it meets the standards of them? Well we want to start off with the operators, the planes that we put them in we want to make sure they're 100% safe, make sure they're Argus rated, you know, waiver and

then they meet all the safety criteria. You know, we vet the operators ourselves, we know the pilots, we know the aircrafts, we know you know the crew that's gonna be on board, that's a start right there. And then from our standpoint is just making sure we handle the client professionally and making sure everything's in order and safety and security is our number one priority internally as well. So I think it's a great value add

and it's now more than ever, clients, they need an intermediary between the client and the operators because a lot of these bigger corporations are just another number. And you're spending a lot of money to travel in this fashion so I think it's needed now you know more than ever for sure yeah I was recently flying I have to say the service was pretty terrible on the plane that I was flying on and I was shocked it just seemed like all the employees are stressed out this This is like a packed commercial airline.

And I think this is a lot of experiences recently. I don't know if they care so much about their job anymore and providing that service. So how do you see the future of aviation? Do you see like you're like Jet 365 or similar companies or just that type of experience growing more because people are sick of like regular commercial and just how bad the experience has become. Yeah I think there's more aircrafts available it's there's definitely a transition we're seeing

an influx of new flyers all the time. It's definitely still a cost huge cost gap but I mean I think it's going to get more competitive with the EV tools and the new advancements in the space. And there will be a lot of new clients entering the market. But I mean, private is the way to go. The overall time savings and the way of getting around is just it's not even the actual flight time. It's essentially everything in between. You don't have to show up an hour before I go through customs. You don't have to wait for your baggage an hour after.

It takes a full day to travel commercial as opposed to private show up five minutes before getting the plane in your destination. You just hop in the car and go. So yeah. I need that. I'm sick of getting there hours before. Like you said, I saw Newark Airport

just had that disaster with their systems and like it's really not the best experience from start to finish. So I used to use a service and I was super happy when they had that service near me and then I moved. But I'm curious, so when it comes to marketing just in general whether it's jet 365 or other companies you had was there a marketing strategy? That worked for you in terms of of getting brand recognition and getting the name out there. Yeah, this is a good one I mean everyone is looking for that edge that you know that SEO that Google strategy. I mean, I'm just old-fashioned I've done everything referral based. I mean when someone someone flies with me, we have like 100% retention rate.

They tell their other friends and other clients and that's how our business has grown. Now we wanted to use F1 as like a global platform and just acquire clients all over the world by also getting our name out and our brand awareness and the credibility that we deserve. So I think it's been all in all win there. And we're excited to do this whole year with them

and acquire clients through them, getting the word out more on a global scale. And yeah, I mean, there's no hidden formula, but we're trying to attack that from all angles, but we're also doing it in a sustainable way. We don't wanna go for like a moonshot where we sacrifice on service. Cause I mean, I can open up Google ads and open the floodgates and have a million

inquiries and get a whole bunch of clients that I can't handle but I'd rather grow it more sustainably and have like a steady growth and just provide a very high touch service where it's needed for these guys so yeah that's where we're at. I'm glad you bring that up because I think sometimes we look at scale in terms of I want to go big or go home yeah but many times it's at the expense of service employees there's there's something you have to give up when you do that too soon or too quick or even just at all like maybe the business has never meant you know to have 10,000 customers maybe it's meant to have less who are paying more anyways

but I'm glad you bring that up So I business for me has always been a roller coaster. There's ups and then the next five minutes there's downs and then there's ups What about you anything that happened in business whether it's now or before that was a significant challenge But you were able to overcome it. Well, I mean, I don't know if you saw the recent statements by Alpine Formula One team the team principal just resigned a couple days after we signed the agreement so I gotta see where that makes our standings between the F1 team and us but I mean there's all kinds of stuff this industry is you know it's like flying a plane you have to figure

out a solution because you gotta land, you know what I mean? When an issue comes up in the cockpit or a navigational thing, you have to work around that and still land the plane and have a successful mission. So it's the same thing in business and entrepreneurial as a whole, you know, doing business, you gotta just find solutions and make it happen, so that.

Really, you're building the plane as you go in entrepreneurship, right? Yeah, yeah. No, I mean, I'm glad, and thank you for showing that about the F1 and just your experience in general, because I think, you know, social media and people in business always putting everything is great, everything is fun, but we know it's a lot of complexities

in five minutes, everything can change, but then in five more minutes, everything changes back. It's always an amazing journey. Did you ever have an experience where, let's say you had to work with somebody, maybe work for a company, but that gave you some skills that you have moved into,

or maybe even some sort of formal education where you learned something there and those skills have moved into or maybe even some sort of formal education where you learn something there and those skills have moved into business. I mean definitely handling the high net worth individuals from my first company. It was focused around like high-end luxury market as well and I mean every client's different, but you kind of want to just put the client first and and really be client focused and I mean things are gonna come up. You just have to move around them. really be client focused and I mean things are going to come up you just have to move around them. I'll tell you there was actually an aircraft that went down for maintenance and I mean we went out of pocket to get him another aircraft that's just you know standard the way we do things you know we don't

ever want to leave a client hanging and I think I learned that in my last business that the second you let someone down is the second you're done you can't say no in this business and you definitely want to just find ways to make things happen. So that's the things I learned in my other businesses and I'm taking towards this one. And yeah. That's the fun part, right? Every day. It's like when you go to a job and you pretty much know your day.

Every day is the same thing. Every day could totally be different than the last day. You get that one phone call, changes everything. So are you finding then that when you're looking at doing business in a luxury market, like you said before, you can't say no to the customer, you really have to go above and beyond. Sometimes that means, you know,

putting out money extra in order to solve a solution. When you say these are some of the things or something else that you learned when you're looking specifically at targeting a luxury market? Yeah, I mean, 100%. These are things you all have to take into consideration. But I mean, there's a big change happening in our industry as opposed to the guys that want it done the old fashioned way to the new generation that wants it completely automated. But I mean, we're dealing with that. Our platform is going to handle the new clientele coming in. We have the old-fashioned ways that are, you know, proven and we've been operating under those, you know,

standards and then yeah, every day you just take it as it comes and it's an ongoing journey. But yeah, we're excited to be here. So when you look at generations like you said younger generation wants automation are you finding that younger generations are also more attracted to the customization versus you know the cookie like a cookie cutter airline is like you buy a ticket like you said you go two hours early you go there's that cookie cutter process are you finding that younger generations are more attracted to your business model and then the more ability to customize things?

100%, yeah, I mean, we're gonna have all kinds of services added onto our platform as well. Like, I mean, catering, car service, that's all gonna be included, but we usually do that manually for our other type of clients. But, clients but I mean yeah people love customizations we've had all kind of crazy requests I don't like to disclose my clients information I know a lot of guys are going on Instagram and saying hey this client's asking for this this client's on there recording the calls if I did that I'd have the

you ever get stuck at checkout and suddenly feel like you're back in 2003? I was in this coffee shop the other day. Their system froze when I went to pay Staff panic. I ended up walking out empty-handed. I was so annoyed. That's why I love businesses that use Square There's a dessert shop that I go to right in Irvine and with Square the checkout is always instant Tap, swipe, done Even if the Wi-Fi down, Square keeps running. Sleek, easy to use, and built to grow with your business. Whether you're selling online, at a pop-up, or managing multiple locations,

which I have done in the past, you need something like Square, and the best thing is it makes it simple. From payments to inventory reporting to customer loyalty, which is everything. Square keeps up so you don't have to slow down. Get everything you need to run and grow your business without any long-term commitments. And why wait?

Right now you can get up to $200 off Square hardware at square.com slash go slash founder. That's N S Q U A R E dot.com slash go slash founder. Run your business smarter with Square. Get started today. One of the best things I've ever done for my personal growth was picking up a new language. Whether you're traveling, leveling up your career, or just love learning, speaking another language

opens up many doors, and Rosetta Stone makes it easier, more immersive, more fun. It's the leading language learning program available right on your desktop or mobile. Rosetta Stone helps you learn naturally just like you picked up your first language through real world context and conversation. Just practical skills you can use right away. What I love most is the true accent speech recognition. It gives you real-time feedback so your pronunciation actually sounds like a native speaker. With 30 years experience, millions of learners in 25 languages choose from like Spanish, also Tagalog, which I'm learning. Rosetta Stone is the go-to for anyone serious about

learning fast and retaining it long-term. Don't wait, unlock your language learning potential now. Founders story listeners can grab Rosetta Stone's lifetime membership for 50% off. That's unlimited access to 25 language courses for life. Visit rosettastone.com slash today to get started and claim your 50% off today. Don't miss out, go to rosettastone.com slash today to get started and claim your 50% off today. Don't miss out. Go to RosettaStone.com slash today and start learning today. Starting your business should be simple.

That's why I love what Northwest registered agent is doing. You can build your entire business identity in just 10 clicks and 10 minutes. Seriously, whether you're launching your first company or your fifth, you get more when you start with Northwest. More privacy, more guidance, and more freedom to run your business from anywhere. They've helped businesses grow for nearly 30 years and they've got your back. For just $39 plus state fees, Northwest will form your business, create a custom website, and set up a local presence anywhere you need it. Want more?

They'll protect your identity by using their address on your formation documents, and their premium mail forwarding gives you a real business address that keeps your home info private, which I have used this service for many years. Don't wait! Protect your privacy, build your brand, and set up your business in just 10 clicks in 10 minutes. Visit NorthwestRegisteredAgent.com slash founders and start building something amazing. Get more with Northwest Registered Agent at NorthwestRegisteredAgent.com slash founders. Craziest stories ever, but I don't want to say anything on air, but yeah,

definitely every situation is different. I've had the craziest requests from in the plane, outside the plane, do this, do that. And we make it work and make sure it's all legal. And yeah, that's it. Alessandro, this has been great. I can't wait to see, you know, what happens with jet 365. You said you're going to send me the hat. So next time we talk I'm wearing the hat maybe even the t-shirt. Oh, but I really really enjoy what you're doing I think it I I

foresee it being the future of travel if someone can afford can afford to do it it makes total sense as to why they would and I can't wait to understand more about Customization and the automation that you'll be you'll be as well So if you want to get in touch with you, they want to find out more information, they want to book, how can they do so? Yeah, you can get us at jet365.io on our website. You can reach out to me personally, af at jet365.io. And I mean, love to answer anyone's questions and talk more about the space.

You know, we're aviation enthusiasts. We love what we do and that's why we do it every day. And you know, just excited to work with people that you know, need the service and love aircrafts as much as I do. And that's it man, growing every day. And thank you so much for the time Daniel, really appreciate it.

I'm not usually good on these like calls, but I hope I did all right and gave the audience what they're looking for. It was great to talk to you. Always like to hear, you know, amazing stories from people who are disrupting industries, like I can tell that you're doing as well. And thank you so much for joining us today

on Founder's Story. Thanks so much. We got a lot coming. Stay tuned. Thanks, Daniel, for the time. The world needs ingenuity. Ingenuity needs accelerators. That's where you come in. Be the tipping point from impossible to impact

at MIT Sloan School of Management. If you're looking for legit ways to make extra money, you've got to check out The Side Hustle Show. With hundreds of actionable episodes to choose from, you'll learn what's working now from real people making real money, like the Utah mom who built a six figure business playing video games, or the guy earning $3,000 a month renting out mobility scooters. Online or offline, from Amazon to your own hometown, from YouTube to vending machines,

The Side Hustle Show has you and your wallet covered. Subscribe to The Side Hustle Show wherever you're listening to this podcast and increase your earning power today.