MMasters in Business
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09 July 2026

Insuring Rare and Collectible Cars and Boats with McKeel Hagerty

4Frameworks
15Insights

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Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 2

Myth Buster37:55

Young People Still Love Cars—Just Not Their Parents' Cars

Hagerty rejects the claim that younger generations have abandoned car enthusiasm. Younger collectors gravitate toward BMWs, Audis, Japanese performance cars, trucks, Jeeps, Broncos, vintage SUVs, and vehicles connected to their own formative years.

  • Car enthusiasm persists across younger generations
  • Each cohort tends to value different formative vehicles
  • Vintage SUVs and trucks are major entry points
  • Modification culture remains part of the appeal

“the next generations are absolutely into cars.”

McKeel Hagerty · 38:02

“They're just into different kind of cars than our parents were.”

McKeel Hagerty · 38:10
#generations#collecting#trucks#car-culture
Myth Buster49:29

Collector Cars Are Not Just a Multimillion-Dollar Hobby

Record-setting auctions dominate media attention, but Hagerty's data depicts a much broader hobby spanning price points, vehicle types, and owner demographics. Pickup trucks and affordable sports cars provide accessible entry points, while participation among women is increasing.

  • Headline auctions distort perceptions of the typical market
  • Enthusiast vehicles exist at many price and reliability levels
  • Trucks and common sports cars create affordable entry points
  • More young women are joining the collector community

“it's a very broad based hobby.”

McKeel Hagerty · 50:16

“There's a really rising cohort of young women and you know, women who want to have these cars and have it be part of their…”

McKeel Hagerty · 50:28
#accessibility#collector-cars#women#market-data

Hot Take· 1

Hot Take54:22

Garage Queens Are Sad Cars—and Storage Does Not Stop Aging

Hagerty argues that collectible cars should generally be driven rather than preserved indefinitely in garages. Tires, belts, hoses, and other components deteriorate with time, while some 1990s and 2000s vehicles age particularly badly when left unused.

  • Low mileage does not prevent age-related deterioration
  • Later collectibles can suffer heavily from prolonged inactivity
  • A higher-mileage car may be easier to enjoy without anxiety
  • Exceptional preservation pieces are a deliberate but narrow exception

“I think those are really sad cars, right.”

McKeel Hagerty · 54:29

“there's not a single generation of cars that fares well when it sits around for a long period of time.”

McKeel Hagerty · 54:37
#maintenance#garage-queens#driving#preservation

Explainer· 7

Explainer12:58

Why Collector-Car Insurance Can Cost a Fraction of Regular Coverage

Collector vehicles often present lower risk because owners care for them carefully and drive them relatively little. Liability exposure is also constrained because one person can only drive one vehicle at a time, even when that person owns a large collection.

  • Careful ownership behavior lowers insurance risk
  • Collector vehicles typically accumulate limited annual mileage
  • Liability follows the driver rather than multiplying equally with every vehicle
  • Large collections can therefore be priced differently from fleets of daily-use vehicles

“wherever there is care, there is better insurance risk.”

McKeel Hagerty · 13:30

“You can only drive one car at a time. Liability follows the person, not the car.”

McKeel Hagerty · 14:24
#insurance#risk#pricing#collector-cars
Explainer17:21

Why Hagerty Evolved from Agency to Risk-Bearing Insurer

Hagerty initially operated as an agency selling policies backed by another company. Beginning in 2017, it pursued the decade-long transition to taking insurance risk itself, increasing the revenue it could capture from the same customer base and supporting its 2021 public listing.

  • An agency can enter insurance more simply than a risk-bearing carrier
  • Owning underwriting risk can capture more economics from existing demand
  • The transition required a multiyear operational journey
  • The risk-bearing model became important to Hagerty's public-company story

“if we actually started taking real risk and became the insurance company itself, not just an agency selling policies for somebody yeltse, it would be…”

McKeel Hagerty · 17:50
#insurance#underwriting#business-model#public-markets
Explainer24:29

Why More Auction Listings Can Make a Marketplace Worse

Digital auction growth depends on balancing inventory with an active bidder pool. Flooding a marketplace with vehicles can disperse buyer attention, weaken results, and ultimately discourage sellers, so Hagerty favors fast but steady expansion.

  • Marketplace supply cannot grow independently of buyer demand
  • Excess listings can drive bidders away
  • Weak bidding then makes sellers reluctant to list
  • Reputation requires honest descriptions and realistic valuations

“if you flood a digital marketplace with too much supply, then the bidders go away,”

McKeel Hagerty · 24:47

“we're not selling it for a million because it's our reputation too.”

McKeel Hagerty · 25:55
#auctions#marketplaces#liquidity#reputation
Explainer27:51

Bringing Magazine-Level Automotive Storytelling to YouTube

As automotive attention migrated from magazines and cable television to YouTube, Hagerty retained professional production standards rather than defaulting to inexpensive creator formats. Its programming spans model histories, barn finds, and time-lapse engine rebuilds designed to entertain enthusiasts.

  • YouTube became the default entry platform for automotive video
  • Hagerty transferred magazine-quality standards to digital production
  • Distinctive formats include Barn Find Hunter and Redline Rebuild
  • Transformation and discovery narratives create broad viewer fascination

“what I wanted to do was do it like as the same high quality like we were doing in the magazine,”

McKeel Hagerty · 28:36

“it was mesmerizing.”

McKeel Hagerty · 30:32
#youtube#automotive-media#content#production
Explainer41:23

Auction Premiums Are Pulling Manual Transmissions Back

Manufacturers once expected electronic transmissions to replace manuals, but collector demand and auction premiums have changed the economics. Some brands now offer expensive manual variants, while owners convert automatic supercars to manual operation as part of a wider return to analog, slower hobbies.

  • Manual versions can command substantial auction premiums
  • Manufacturers have introduced additional manual configurations
  • Manual conversions are appearing in high-end collectible cars
  • Collectors increasingly value engagement over maximum track speed

“suddenly the manual version of something huge, absolute premium.”

McKeel Hagerty · 42:46

“I think it's the return of the analog people more, you know, interested in driving.”

McKeel Hagerty · 43:07
#manual#analog#auctions#driving
Explainer44:04

The Coming Transfer of 12 Million Enthusiast Vehicles

Hagerty estimates that roughly 12–13 million enthusiast vehicles, currently worth about $570 billion, will move between generations over fifteen years. The next owners may favor younger cars, sports models, and trucks, creating both a market transition and a need for skills such as manual-transmission driving.

  • Baby boomers currently hold much of the enthusiast-vehicle value
  • About one-third of the market may change hands within fifteen years
  • Successor generations enter through different vehicle categories
  • Education can help preserve participation in analog vehicles

“twelve thirteen million vehicles, it's about five hundred and seventy billion dollars worth of car value.”

McKeel Hagerty · 44:45

“we need to teach the next generation how to drive manuals.”

McKeel Hagerty · 45:52
#inheritance#wealth-transfer#collector-cars#generations
Explainer47:24

Why the Collector-Car Bull Market Is Shifting Toward the 2000s

Demand for 1990s and 2000s cars comes from both younger buyers with new wealth and established collectors who do not want to miss the next culturally important category. Older, wealthier bidders can amplify a generational trend by outbidding the cohort that first made those vehicles fashionable.

  • Younger buyers are entering with nostalgia for newer vehicles
  • Established collectors also pursue newly fashionable categories
  • Cross-generational bidding can accelerate price appreciation
  • Some buyers choose cars that their grandchildren will recognize as cool

“it was also the older generation of collectors who liked earlier cars saying like, well, maybe those are cool and I want one too, and…”

McKeel Hagerty · 48:36

“I want to have a car that my grandkids thinks is cool.”

Unnamed collector quoted by McKeel Hagerty · 49:07
#valuation#nostalgia#supercars#demand

Story· 1

Story04:20

The $500 Porsche That Started a Lifetime of Collecting

At thirteen, Hagerty bought a 1967 Porsche 911 S for $500 and restored it with his father. Lawn mowing and apple sales financed the parts, and the car was ready by the time he could drive; he still owns and drives it.

  • Hagerty grew up restoring vehicles with his father and sisters
  • He financed the restoration through childhood businesses
  • Older performance cars were inexpensive rather than prized collectibles in the 1980s
  • The Porsche remains his first car out and last car stored each season

“I had to mow an awful lot more lawns and to sell a lot more apples out of my orchard to buy the parts to…”

McKeel Hagerty · 05:17

“It's my first car out every season and the last one I put away.”

McKeel Hagerty · 06:27
#porsche#restoration#collecting#family

Q&A· 1

Q&A51:12

The Best Affordable Entry Points for Weekend-Car Buyers

For an inexpensive convertible weekend car, Hagerty recommends a Mustang or Mazda Miata because both are plentiful, affordable, serviceable, and available with manual transmissions. European-car buyers can start with a Porsche Boxster or an older BMW 3 Series before moving to a 911.

  • Miatas offer reliability, track capability, and low purchase prices
  • Mustangs add power while remaining common and serviceable
  • Corvettes provide another widely available American option
  • Boxsters and older BMW 3 Series models are accessible European entries

“If you want to go track driving, they're the great track cars. If you want to just cruise around a weekend, they're inexpensive.”

McKeel Hagerty · 51:40

“you want a nine to eleven, But let's start you in a box star,”

McKeel Hagerty · 52:29
#miata#mustang#boxster#buying

Tool· 1

Tool20:01

The Serial-Number Decoder Behind Accurate Classic-Car Valuations

Model names alone can conceal enormous differences in a collector car's specification and value. Hagerty built a patented pre-1981 serial-number decoder to distinguish variants and combine that classification with insurance, auction, purchase, and sale data.

  • A single model year may contain many materially different variants
  • Visually similar vehicles can have radically different values
  • Serial-number decoding creates more accurate classification
  • Insurance activity supplies data beyond public auction results

“In nineteen sixteen and the Camaro came in one hundred and forty seven different variants, and that year the least expensive one was worth about…”

McKeel Hagerty · 20:59

“we built a patented serial number decoder for all cars pre nineteen eighty one so that we could understand our universe and start providing that…”

McKeel Hagerty · 21:16
#valuation#data#vin#collector-cars

Takeaway· 2

Takeaway1:03:18

Graduates Should Not Overlook Boring, Stable Industries

Asked for career advice, Hagerty argues that established industries such as insurance still offer substantial opportunity. They need capable people who can apply new technology and remake old operating models, even when those fields lack fashionable reputations.

  • AI anxiety dominates current graduate advice
  • Established industries offer stability and room for reinvention
  • Unfashionable sectors may have less competition for ambitious talent
  • A seemingly boring core industry can support an unusually interesting career

“Don't overlook things that you consider boring today,”

McKeel Hagerty · 1:04:09

“They need really smart people who want to work hard and remake what they are”

McKeel Hagerty · 1:04:03
#careers#insurance#graduates#ai
Takeaway1:04:36

Ignore the EV Culture War and Play the Automotive Long Game

Hagerty views arguments between electric and internal-combustion advocates as a distraction from the industry's long history of changing propulsion technologies. He expects more electric vehicles alongside continued demand for strong combustion cars and favors watching the broad market rather than joining partisan debates.

  • Automotive propulsion has never been technologically static
  • Electric, steam, and combustion vehicles have coexisted historically
  • Future growth in EVs does not require the disappearance of combustion cars
  • Long-term strategy should not be driven by short-lived cultural arguments

“I'm very agnostic about all of that stuff, and it's very easy to kind of get sucked into those arguments.”

McKeel Hagerty · 1:04:52

“continue playing the big long game and don't worry about some of the little petty arguments”

McKeel Hagerty · 1:05:16
#electric-vehicles#combustion#strategy#automotive