Is a Vintage Ride a Solid Investment or Just a Money Pit?

By Tyler Grant February 9, 2026
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Is a Vintage Ride a Solid Investment or Just a Money Pit? @ Men's Journal

A thin-blade key, a relic in today’s world of keyless entries and push-button starts, turns in the ignition. The torque of the V12 engine—a direct descendant of the monster powerplants built for the 24 Hours of Le Mans—rocks the body of the Daimler Majestic Insignia. We begin to cruise through the underground parking garage. For now, this is the only way to drive it; the latest addition to the collection of fintech entrepreneur Philipp Ilyin-Adaev hasn't received its plates yet.

Through the heavy soundproofing, the velvety purr of the Jaguar Double Six filters into the cabin, which is finished in matte gray leather and Mineral Green wood trim. As we carve circles to the accompaniment of that V12, there’s time to pick Philipp’s brain about his collection.

A "Youngtimer"—or what we in the States call a modern classic—is an informal term for a car usually between 20 and 30 years old that shows clear potential to become a full-fledged classic car once it hits the three-decade mark. It’s that sweet spot of stealth wealth and analog soul.

"The hardest part of this hobby is building a business successful enough to sell, just so you can use the proceeds to start buying cars," Philipp jokes.

But seriously, his journey into car collecting started like many others. In the early 2000s, he went to a local used car lot looking for an upgrade from his basic Lada (the Soviet equivalent of a beat-up Chevy Nova). He was hunting for a Mercedes C-Class, but ended up with a BMW E39 because the Benz felt too cramped. Later, a 530i occupied his garage, followed by the ultimate iteration of that chassis—the legendary M5. However, he didn't truly feel like a collector until he acquired his first Jaguar.

Philipp spotted the XJ-SC cabriolet in a film—it was the ride of choice for a high-profile character. "I didn't even know this model existed," Ilyin-Adaev recalls. "When I found one for sale, it turned out to belong to a leader of the Jaguar enthusiast community. After talking to him, I knew I had to pull the trigger—it was in concours condition."

Shortly after the XJ-SC, the collection grew with an Alpina B12 (based on the BMW E38 7-Series), a rare beast even by global standards. "At some point, I realized it made sense to collect the whole lineage," Philipp explains. "I have the E38, so naturally, I need the E32, then the E23, and so on." When he sold his major tech business late last year, the opportunity to scale the collection finally arrived.

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BMW cars from the collection of Philipp Ilyin-Adaev. Photo: Sergey Domushchy

Today, this auto enthusiast’s soul has plenty of room to breathe in a 30-car private garage, which is already half-full. However, don't expect a massive variety of brands. For a mid-scale collector, the biggest headache is "brand hopping." You don't know the common failure points, you lack a specialized mechanic, and you don't have sources for rare parts.

"I recently picked up a Maserati Quattroporte with only 30,000 miles for about $27,000," Philipp shares. "But I'll need to sink another $27,000 into it just because of its age. I know nothing about the brand yet. If I hadn't found the specific tech who serviced this exact car, ownership would have been a descent into the nine circles of hell."

Anton Sumin, another expert from the modern classic community, illustrates the complexity of owning rare luxury metal: "We're currently working on a 1987 Bentley Eight. It was bought for roughly $7,500 in decent shape. We’ve already spent $5,500 just getting it roadworthy. Based on my experience with the brand, I wouldn't even approach a Bentley without a $35,000 'war chest' for repairs."

It’s clear why novice enthusiasts often shy away from truly exotic machinery. When asked about his "next big thing," Ilyin-Adaev points to the Alfa Romeo Montreal, designed by Marcello Gandini at Bertone, and the BMW E9 coupe.

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Classic BMW E9

Anton Sumin has his own "lotto win" dream: "With an abstractly unlimited budget, I wouldn't just buy street cars. I’d be happy with a BMW M5 E34 in Daytona Violet. With the rest, I’d hunt down a Lola T70 and race the Le Mans Classic in a Sauber."

"A typical car collector is a person with a high level of education and cultural awareness. There are no 'accidental' people in this sphere."

Gleb Rachko, head of OldtimerCars, a boutique firm that sources vehicles for high-net-worth individuals, notes that his clients are typically established, well-read people with a thirst for knowledge. "You have to grow into a retro car. It requires a certain level of cultural 'mileage.' You might not know the technical specs, but you must be able to appreciate the heritage."

According to Rachko, the focus on European cars is largely financial. The golden era of the US market was the 1950s. "America has always dictated the trends," Rachko asserts. "It was the demands of the US market that gave us masterpieces like the Mercedes-Benz 300SL 'Gullwing', the Porsche 356, and the Jaguar E-Type."

Prices for "Oldtimers"—pre-war legends from Duesenberg or Alfa Romeo—are already in the stratosphere, often hitting seven figures. Even serious 50s and 60s European classics require a couple of hundred thousand dollars to get in the game. "That’s why beginners and budget-conscious collectors are looking at modern classics from the 90s and 2000s," Rachko adds.

The Modern Classic as an Investment: Business vs. Nostalgia

Treating a car as a pure investment is tricky. In the US, we have the Bring a Trailer effect where prices can skyrocket, but in other markets, import duties kill the margin. Philipp’s Daimler is a prime example. Bought for €28,000, it cost €30,000 just to clear customs. After restoration, the total investment will hit €90,000 ($97,000). It’s unlikely he’ll be able to flip it for a profit anytime soon.

Ilyin-Adaev shares another story: his Alpina B12—a 1999 Geneva Motor Show car. He "snatched it" for about $22,000, then sank another $55,000 into it. It needed a full glass-out respray, a total interior re-trim, and a complete engine rebuild. For context: a single piston for an Alpina V12 costs about $1,100—and there are twelve of them. "Between taxes and insurance, it costs me $2,200 a year just to keep it. Would anyone buy it for the $85,000 I have into it? I doubt it. But then again, I’m not selling."

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Philipp Ilyin-Adaev with his car

A "star" provenance can drastically change the ROI. "If it’s a BMW owned by a mid-level bureaucrat, nobody cares. But if it was owned by a cultural icon like a famous rock star, you’d buy it in any condition. That’s a blue-chip acquisition," says Philipp.

In most cases, breaking even after enjoying a car for a few years is considered a "win." However, Philipp has one "unicorn" in his garage where passion and profit align: a BMW M5 Touring 'Elekta' (E34). Only 891 M5 wagons were made. Only 20 were 'Elekta' editions for the Italian market—ten in green, ten in silver. Only seven of the green ones are known to survive. Recently, one of these super-wagons sold at auction for $120,000.

"When you invest, you shouldn't choose what you like; you choose what has the most growth potential. But for most collectors, nostalgia always trumps the business plan," says a representative from Vogue's lifestyle circle.

Rachko recommends that those looking for a "buy and hold" should target the 80s and 90s. "Look for a premium sport coupe or cabriolet, like a BMW 850 CSi. It might cost $100,000 now, but in 10 years, that price will likely double or triple."

The Time Capsule: The Ultimate Flex?

"Time Capsules"—cars in original, untouched condition with delivery mileage—are the holy grail. They are incredible investments, but they have one major flaw: every mile you drive deletes value from the odometer. An enthusiast who actually wants to drive their cars will find this agonizing.

"You can restore an oldtimer anytime. But a car is only original once," Rachko explains. "I once imported an Aston Martin DB5. The leather was worn, the paint was faded. But restoring it would have been a crime. It’s like a Rembrandt that has never been taken out of its original frame."

Will We Ever See a "Schlumpf Collection" in the Modern Era?

The Cité de l'Automobile in France houses the world’s largest collection of Bugattis, built by the Schlumpf brothers. While there are massive private collections today, they are rarely turned into public museums. Why? Because the "old money" transparency of the past has been replaced by a desire for privacy.

Ilyin-Adaev once toyed with the idea of opening a BMW Museum in Moscow. But after crunching the numbers, he realized it would be a "charity project." "I can't just buy a building and fill it with 50 rare BMWs when tickets only cost $5. It wouldn't even cover the rent. Unless a brand like BMW officially sponsors it, it’s a pipe dream."

Do Modern Cars Have a Chance to Become Classics?

Looking at today’s plastic-heavy, tech-saturated cars, it’s hard to imagine them becoming collectibles. Our experts believe the future classics will be the "analog outliers"—cars with character and simplicity, like the Toyota GR Yaris (a car we sadly don't get in the US, though the GR Corolla carries the torch).

"Any beautiful, unusual car from a brand with history has potential," Rachko says. "Look at the Isuzu VehiCROSS—it’s a weird Japanese SUV, but it’s unique. Or the Honda S2000. These are future legends that will sit right next to an Alfa Romeo 4C in the halls of fame."

The problem for future collectors is that the "entry fee" is rising. As we move toward a world of EVs and autonomous ride-sharing, the number of unique, soul-stirring cars is shrinking. If you want to own a piece of automotive history, the clock is ticking.

"The best time to buy a vintage car was yesterday; the second best time is today." — Hagerty Insider

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Tyler Grant

Tyler covers a wide spectrum of subjects—from travel and gear to mental health, hobbies, and modern masculinity. His approach is conversational and experience-driven, aimed at making content feel personal and accessible.

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