
The Sweaty Startup · 2026-07-12 · 16 min
Key moments - from our scoring
Substance score
61 / 100
Five dimensions, 20 points each
This episode challenges the Silicon Valley mythology of entrepreneurship by revealing who actually owns private jets. Speaker A, an entrepreneur and author, argues that real wealth comes not from venture-backed tech ideas but from execution-focused "boring" businesses: waste management companies, HVAC operations, regional restaurant chains, siding businesses, mortgage broking, and asphalting. These business owners don't raise capital; they build operational excellence, sales skills, and management discipline. The conversation covers Speaker A's purchase of a 1/4 share in a Vision jet for roughly $925,000 with additional monthly costs of about $2,000 (hangar split four ways at $5,000/month, plus pilot fees at $1,250/day). Speaker A describes the practical freedom a jet provides - responding to family emergencies across a seven-hour distance in 12 hours total, attending business meetings same-day, and maintaining work-life balance by dropping kids at school before boarding. The episode also covers his pilot training journey, including a harrowing moment in a 1964 Cessna 172 that convinced him to hire professional pilots rather than become one himself, given his operational demands. For B2B operators, this episode reframes what "success" actually looks like and how unglamorous business models generate the cash flow to sustain premium assets.
Owners of regional waste management, HVAC, siding, mortgage broking, asphalting, and similar operational businesses - not venture-backed tech founders. They built wealth through execution, leadership, and scaling operations rather than novel ideas.
A 1/4 share costs approximately $925,000 at purchase, plus roughly $2,000/month in fixed costs (hangar split four ways at $5,000/month total, pilot fees at $1,250/day when flying), and hourly wing-to-wing maintenance costs around $540/hour.
For time-sensitive operators, private aviation converts multi-day trips into single eight-hour work shifts: you can drop kids at school, attend a meeting in another city, and be home by dinner - something impossible with commercial airlines and TSA delays.
Although interested in aviation, he decided the operational burden of maintaining currency (VFR requirements, weather delays, mechanical risks) was incompatible with his busy schedule managing multiple growing businesses, making it more efficient to pay professional pilots.
Being a good salesperson, leader, and decision-maker; hiring and delegating effectively; solving problems consistently; and maintaining humility balanced with confidence - not the business idea itself.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode delivers some genuinely useful ideas - particularly the thesis that sustainable wealth comes from boring, executable businesses rather than venture-backed startups, and the specific operational lessons (delegation, hiring, sales, problem-solving) that matter more than the initial idea. However, execution is thin on depth; most insights are restated variations of the same core point repeated across multiple examples (siding business, mortgage broker, tree service, etc.). The practical details on jet ownership costs and management structure add value, but the conversation doesn't dig into *how* these founders actually scaled or what specific decisions made the difference.
Their idea is not what got them where they are. Their execution Is they were good salespeople, they were good leaders. They're charismatic. They could make good decisions, um, they could hire, they could fire, they could delegate.
The people flying private jets are the ones who own a regional waste management company. They own an H vac business, they own six branches of a quick service restaurant.
The core theme - that ordinary service businesses build more wealth than VC-backed startups - is not new and has been articulated in various corners of entrepreneurship writing for years. The guest's book appears to be a systematic treatment of this idea, which has merit, but the podcast conversation itself doesn't generate novel angles or first-principles thinking. The framing is contrarian relative to media narrative but not relative to practitioner wisdom. The jet-as-status-symbol reframing (toward boring businesses) is slightly fresher than typical startup discourse but still familiar.
But those aren't the people flying private jets. Uh, the people flying private jets are the ones who own a regional waste management company.
you want to make money. There's two ways to go. There's the social media way, there's the Shark Tank way, there's the sexy way, Silicon Valley walking around sweatpants. Or there's the, uh, hey, let's look at what real normal people in my town who have the nicest houses.
The guest is a credible operator: he owns multiple businesses, is actively building a real estate private equity company, has bought a $52M business, and owns a fractional jet with real skin in the game. He's not a consultant or pure thought-leader. However, the specifics of his operational scale and portfolio are somewhat murky (multiple businesses mentioned but not deeply explored), and it's unclear which business generated the majority of wealth. He's substantive but not exceptionally specific about his own journey's details.
I just bought the company I, um, had, you know, still involved in these businesses, having a blast.
I'm not buying a, you know, $52 million business and raising $20 million and, you know, running a real estate private equity company and also growing a real estate services firm that's exploding.
The episode includes concrete numbers on jet costs ($3.65M purchase, $900k for 25% stake, $1,250/day pilot cost, $5k/month hangar split by 4, $540/hour wing-to-wing), which is valuable. Business examples are named but not deeply detailed (siding, mortgage, asphalting, steel tubes). The tree-trimming example ($12k quote) is specific but anecdotal. Missing: actual revenue figures for any of the 'boring businesses,' growth timelines, profit margins, or data on how these founders scaled. The stories feel illustrative rather than evidential.
It was 3.65 out the door and then we bought 300 hours of the wing to wing for $540 an hour. So that was another 150k.
My 1/4 share, 25%. I wired 900, let's say $925,000 at closing.
Host shows genuine curiosity and follows up on interesting threads (the pilot story, cost structure, becoming a pilot himself), but questioning lacks sharpness. Most follow-ups are soft enablers ('Yeah, tell me more about...') rather than probing deeper into *why* these businesses work or challenging the guest's assumptions. When the guest mentions buying a $52M business and raising $20M, Host doesn't ask what that business does or how it connects to the jet economics. Questions are warm and conversational but don't push for the kind of specificity that would unlock richer insights.
Tell me a little bit about, um, kind of like how having the jets kind of transformed your approach to business travel. Has it made you do it more?
Yeah, I will say in my pilot group, uh, we've got about 10 ah, of us in a kind of, you know, text group and we fly together a lot
Computed from the transcript - who did the talking, and the words that came up most.
In this episode, I break down the reality behind private jets and why the people who own them aren't who you think. It's not tech founders or venture backed startups. It's operators running simple, "boring" businesses like HVAC, storage, and local services. I share how those businesses create real wealth, and how that wealth translates into true freedom like being with family when it matters and turning full day trips into a few productive hours. I also walk through exactly what it costs to own a jet, how I structured the deal, and how the management works behind the scenes. And I get into my own journey of learning to fly, what changed my perspective, and why I ultimately decided to focus on building instead of being in the cockpit. Grow your business: Book: Newsletter: My Companies: Offshore recruiting - Cost segregation - Self storage - RE development - Brokerage - Paid ads - SEO - Insurance - Pest control - Sell a business: Buy a business: Invest with me: Social Profiles: X - Instagram - TikTok - LinkedIn - Podcasts: The Sweaty Startup & The Nick Huber Show Free PDF - How to analyze a self-storage deal:
Transcribed and scored by The B2B Podcast Index.
Speaker A: So my book is really kind of a call out on what entrepreneurship is painted to the media. Because you walk around town and on the streets you say, hey, what does an entrepreneur mean to you? Just to a random person, they're going to say Shark Tank. They're going to say new ideas. They're going to say raising venture capital. They're going to talk about Mark Zuckerberg, Elon Musk, Steve Jobs, Bill Gates. Um, but those aren't the people flying private jets. Uh, the people flying private jets are the ones who own a regional waste management company. They own an H vac business, they own six branches of a quick service restaurant. They own two Honda dealerships, they own four or five oil wells.
Speaker B: Um,
Speaker A: I tell this all the time, like, okay, you're an entrepreneur, you want to make money. There's two ways to go. There's the social media way, there's the Shark Tank way, there's the sexy way, Silicon Valley walking around sweatpants. Or there's the, uh, hey, let's look at what real normal people in my town who have the nicest houses, go to the nice country club, have the nice beach house in Hilton Head, and have a PC12 sitting in Athens. None of them raise venture capital.
Speaker B: Yeah, I will say in my pilot group, uh, we've got about 10 ah, of us in a kind of, you know, text group and we fly together a lot and stuff like that. Uh, none of them are tech entrepreneurs. Most, um, of them run the most boring, you know, businesses. One sells siding, um, for houses, um, and has one of the most successful siding businesses here in, in Oklahoma. And he's like, I'm redneck rich. You know, he's, he's come from like, absolutely nothing and he's got four planes and that sort of thing. Another one's a mortgage broker who's just very good at running his mortgage broking business. And it's very simple. Like he's like, I don't do anything special other than just pick up the phone and get the deals closed for my clients and that's it. And then we've got another one who runs an asphalting company, you know, just lay driveways all day. Um, another one who manufactures steel tubes. Just really boring kind of stuff. Um, but they all fly.
Speaker A: This is what my book is. It's how to find an opportunity like that, how to think about business, how to manage, how to hire, how to delegate. The key, the unique thing about all of the people you just mentioned. Their idea is not what got them where they are. Their execution Is they were good salespeople, they were good leaders. They're charismatic. They could make good decisions, um, they could hire, they could fire, they could delegate. They got better at solving problems. They weren't too anxious, but they weren't too arrogant either. They had that balance of humility and confidence. Um, these are all the things that I talk about in my book and I tell, you know, 40, 50 stories just like the ones you mentioned.
Speaker B: Yeah, I love to, uh, to hear that. And that's actually something, you know, one of the inspirations to start this podcast and, and another business in aviation that I'm working on is exactly those stories that you, you talk about is there's so many people that just have figured out how to take a very simple thing, do it well, do it often get better and better over a period of time. And they've made a very successful, uh, business, you know, out of it. And you don't have to over complicate it. A, um, lot of people, again, think that, you know, you have to go build a Facebook or I have to go have some really, really novel idea. But, you know, there's some guys chopping a tree down at my house this afternoon, and he's charging $12,000 to take a tree down, and that's it. And it's like, that was the cheapest quote that we had. I mean, it's a complicated.
Speaker A: And if that guy is good at, uh, you know, delegating, he can get people, he can find people who can cut the tree down, then he can find people to manage the person to cut the tree down. Then he can have five crews, six crews, and then he's in two cities. Um, then three or four years later, he's got a Phenom 300 sitting at the airport.
Speaker B: You kindly, uh, sent me the book that you've been working on, and, uh, from the amount that I've read, it's an awesome story and gives, uh, some really, really amazing, uh, insight and, um, guidance to people that probably would have never thought about starting a business, running a business, building a great business, even from a place like Athens, um, and just the freedom that, that ultimately gives you if you're able to generate success and wealth. And I guess on that, um, kind of line of thinking, how do you think about freedom when it comes to using the jet and flying? I mean, having a PJ is probably like the ultimate, uh, sense of true freedom and, uh, sign of success. But maybe talk to me about the freedom that it gives you.
Speaker A: Yeah, I mean, there is, there is nothing Better than like, so we had a bit of death in the family. For example, I'm seven hour drive away because we also chose to live in an area that's great to live in, but not close to family. A lot of people struggle with that. Um, I text my pilot the next morning at 8am, the plane is sitting there, we're in the plane and we're in my parents kitchen with them 12 hours after my grandmother passed away. And it was absolutely zero stress. Like leave the house, leave the house at 7:30am, walk in the kitchen, seven hour drive away at 10, you know, 10:00am um, that's just an, that's an, it's a time machine really. Like I literally would have had to either drive to Atlanta, which is two hours, wait an hour, get on the plane, fly for an hour, get off the plane, drive an hour and a half to my, to my home farm in southern Indiana to be with my family. So yeah, it's totally, totally unbelievable. Same goes for business. Like we need to see a property to make a deal with an owner. We're there, we can be there like right away. We, we need to close an executive hire and they're in Houston and our team's in Houston. We can get on the plane and we can be there by not like 2pm but or get up at 4am like we get up at our normal time, take our kids to school and we're walking in the board meeting in Houston at 10:00am Unbelievable. Um, freedom.
Speaker B: Absolutely. And I mean you talk about dropping the kids off and in the book you actually talk a lot about work life balance and how important that is and how, you know, the type of business that you build is very important in enabling that and the location and that sort of thing. Um, talk to me about kind of other experiences where aviation has allowed you to have a much better work life balance.
Speaker A: Uh, you know, work life balance. I'm home by dinner, um, and I get to drop my kids off at school, which wasn't possible before. You know, I'd be getting a driver to pick me up or I'd leave the house at 4:00am um, from Atlanta. Um, it would mess up, you know, a whole night of sleep. I would feel like crap that night, um, and I would not get home until 11pm if it was a day trip. So it's really all about. It turns a full day or two days into one eight hour work shift, which allows me to see my kids and be home and not feel like crap.
Speaker B: Tell me a little bit about, um, kind of like how having the jets kind of transformed your approach to business travel. Has it made you do it more? Talk me through that kind of um, uh, the thoughts when you're kind of going to put together a business trip.
Speaker A: Yeah, so if I was making a little bit more money, I'd be using it a little bit more, I'll say that because it is still like to make a run round trip to New York because it's got to drop me off, it's got to fly back and then I'm there for a couple days. Um, you know it's 15, 15 to $20,000 cost. So that's not, that's not insignificant for one business trip. Um, it's ten grand to go to Houston for the day to meet a CEO. Done that. Um, so the cost is pretty significant. But man, yes it is uh, something that I just look at as a cost of living in Athens and I make it happen when I need to be somewhere for business. And yeah, we have. The great thing is our management company has two visions and three pilots. So when mine's in the shop, I use theirs. Um, there's also three PC 12s in the fleet and those PC 12 owners love using my vision. So if I do need a PC12 if I got extra weight, um, or again my plane is in the shop, they love trading hours with me so it works out really, really, really well. I think having a phenomenal management company to back me and my plane has been amazing. I'm also happy to kind of talk through if people would be interested in the, the breakout of expenses to actually buy it. If you want, if you guys want to hear that.
Speaker B: Yeah, definitely. I mean, let's go through that because a lot of people, you know, try to buy a plane themselves and when you're buying a single engine piston and uh, you know, even a sort of lower cost turbine, you can do it. Um, but it becomes a challenge when you start to run into the jet world or you know, the 10,000 uh, pound sort of PC12 or any of the bigger, bigger uh, turbines. So talk us through, yeah, the dollars and cents when it comes to actually making the purchase and then how that management uh, works for you and maybe carry some of the burden of managing the day to day with the aircraft.
Speaker A: Yeah, so it was 3.65 out the door and then we bought 300 hours of the wing to wing for $540 an hour. So that was another 150k. A couple other random costs make it let's say $4 million out the door. Maybe a little less. Right. I. My 1/4 share, 25%. I wired 900, let's say $925,000 at closing. Um, then the management company takes ownership and they. They charge us. So the wing to wing includes all the maintenance we still have to pay to fly it back and forth to Knoxville to get a service done. Um, but hangar. Hangar is five grand a month split by four guys. Um, and that's about it. Um, so then they. The management company, how do they make their money? The daily, daily pilot rate. Um, they charge me 1250 a day for a pilot. Um, you know, they pay the pilot 4, 500 bucks, whatever it is, and that's their profit. So when the planes are flying, they're making money. Um, it's taken. We've owned the. We've owned the plan a year and three months, and it's taken that long to get our. We're very close, but still not gotten our charter. Uh, which is just the. The speed at which the FAA moves is insane. Um, but, yeah, it's been. So if I'm. If I'm not flying my plane, you know, it's two grand. Two grand out the door a month. But last year, you know, came time to buy another 500 hours of wing to wing, and, you know, you gotta wire 75 grand to the LLC.
Speaker B: Now, where it potentially becomes a little bit more cost effective for you to, uh, go fly the jet is you flying it yourself. And, uh, you told me that you've started on your journey of, uh, learning to fly, and one day you'd love to fly the Vision jet, and then maybe the phenom, uh, uh, 300 at some stage. But you told me you also maybe had, uh, a little bit of an interesting experience on the. On your second ever flight. So maybe talk us through your, uh, your thought process on becoming a pilot and then, um. Uh, yeah, what, what the learning experience has been so far.
Speaker A: Yeah, I think the, um. Look, I love aviation. I would love the freedom to be able to go and get in an airplane that's sitting in Athens whenever I want. Um, so I was first interested in the way more approachable planes, the pipers, the bonanzas in the two to $350,000 range. It's crazy because five years ago they were $150,000 planes. But I hired a guy to help me try to find a bonanza. Um, and I started taking lessons, and I realized real quick that I have a shitload going on. And, um, when I need to make a meeting, weather, um, like it's just not feasible for me to worry about, you know, VFR or flying around storms in an airplane that goes 190 miles an hour or, you know, to 2:40 if you're lucky, in a bonanza, depending on winds. So. But I was taking lessons and I was in a 1964 Cessna 172. And first three lessons were amazing. I was into it, I was loving it. Um, I studied it a lot. I was practicing talking to air traffic controller, air traffic control, all these things. But one day there's a 15 knot crosswind and the instructor doesn't tell me. Um, um, it was, it was gusts from 5 to 15 and we take off and August hits and the whole airplane slides to the side. I don't think it was a dangerous situation by any means, but it scared the living out of me. We get up, we get up to, you know, 4,000ft and we're starting to do practice routines and working on stuff. And he, then he tells me a story that the other one in his fleet, the other plane, the throttle cable broke the day before and they landed it. He's like, see that field down there? That's where they landed the other plane yesterday. And I'm like, hold on. What? He's like, yeah, the, the throttle cable broke and they landed it right there. Fixed the throttle cable and he took off out of that field. I'm like, okay, well, that sounds great, but wasn't that plane flying at night home from like, I watched flight radar? That plane was flying home at night yesterday, two days before that from Hilton Head. What happens if that happens at night? You're dead. You're dead. Like, there's. Okay, maybe you can land on a road and somebody else is dead. Maybe, maybe you're okay. Maybe you can find a field. Um, and I just didn't. The pilot just had no. Like, he wouldn't reconcile the fact that, hey, if that happens, the flight earlier, the pilot's dead. So I made the decision right then that it's either going to be a SR22 or I'm going to pay somebody else to do this. And like, over the course of that time, two of my businesses really started to grow a lot. And I started making a lot more money over those four or five months and I decided to do it the right way.
Speaker B: Yeah, I mean, certainly having someone fly you for now is a great way to do it. And then as you get to a point where you, you've got.
Speaker A: And I had a lot going on. Like, I just bought the company I, um, had, you know, still involved in these businesses, having a blast. I think there will be a point in my career, absolutely, when I'm not that busy. Um, I'm not buying a, you know, $52 million business and raising $20 million and, you know, running a real estate private equity company and also growing a real estate services firm that's exploding. And I'm putting a lot of time there. Um, there's going to be a point in time where, because entrepreneurship, it really comes in, in waves, like, I, I, there's, there's years where you really bust it and work your butt off, and then there's years when things are slow, like, frankly, and you just gotta sit back and wait. And time does its thing because you have a good business, you have good people. It's blocking and tackling. Now that time will come, and maybe my son will be interested in aviation, and maybe we'll buy a SR22 and fly, and then it's a really easy trip from an SR22 to a vision, so.
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