Kevin O'Leary Watch Collection & Starter Watch Recommendations

Kevin O’Leary joins us for another episode of Watch Talk to discuss the best watch investments. Shop our collection of pre-owned Rolex watches: www.bobswatches.com/rolex/
NAVIGATE THIS VIDEO
00:00 INTRO
00:24 Starter Watches
01:59 Colored Dials
03:26 F.P. Journe
05:47 Paul Newman
07:40 Couch Watch
09:37 Red Watch Bands
11:52 The Purchase
13:20 Outro
At Bob’s Watches, we boast the largest inventory of certified pre-owned luxury watches on the secondary market. Click here now to shop the brands discussed in this video and much more: www.bobswatches.com/luxury-wa...
Kevin O’Leary is no stranger to making smart investments. He’s one of the world’s most successful businessmen and entrepreneurs, having founded and invested in numerous multi-million dollar businesses.
He’s also a published author, a fixture on the smash-hit television show Shark Tank and has even entered politics with a run for Prime Minister in Canada. He’s a busy man, and we’re honored to sit down with him for our latest installment of On the Clock.
STARTER WATCHES
First, Kevin and Paul review some of the best entry-level watches. They’re great investments, affordable, and look great on the wrist.
The top brand for many introductory collectors is Rolex, with a price of between $5k - $10k.Rolex might seem out of reach for novice collectors but compared to other top brands like Patek Philippe and Audemars Piguet, Rolex is relatively affordable, especially if you shop pre-owned. There are several very attractive options to consider.
THE DATEJUST 36
The Datejust is one of the most iconic and legendary Rolex watches ever made. It’s instantly recognizable with the jump date mechanism at the 3-hour marker and the famous Rolex logo at 12 o’clock. It’s a bold power move to wear a Datejust. Still, it doesn’t command a top-tier price and is very obtainable by the average collector.
The stainless steel edition is versatile and will appeal to men and women of all lifestyles and professions. You can wear it to work with a tie or around town in jeans. The options are endless.
COLORED DIALS - OYSTER PERPETUAL
Vibrant dial colors are quickly gaining steam. While the newest lineup of colorful Oyster Perpetuals wasn’t particularly popular when it came to market just a few years ago, it’s quickly becoming one of the most sought-after Rolex models on the market.
The Stella-inspired dial colors include black, pink, silver, turquoise blue, yellow, blue, coral red, and even green. From there, the OP collection is available in 41mm, 36mm, and 31mm.
Prices on the secondary market fall under $12k. Brand-new, prices are significantly lower. However, the Oyster Perpetual with its more colorful dial options is becoming harder to find on the retail level.
F.P. JOURNE
Looking at Kevin’s watch roll, he’s traveling with a handsome example of the F.P. Journe Bleu. When it sold at retail, the watch was considered entry-level with a price range of around $18k and $28k. Limited production and sightings of the watch on some high-profile wrists have since boosted its value to at least $100k. An excellent investment, to say the least.
PAUL NEWMAN
One of the most expensive watches ever sold was Paul Newman’s personal Daytona, which fetched over $17 million at auction. Considering his wife, who gifted the watch to him decades ago, probably only paid a few hundred dollars, it is easily one of the best watch investments ever made.
COUCH WATCH
At Bob’s Watches, we hear some rather fascinating stories of how our customers come into possession of the watches they sell us. Perhaps one of the best investments any of our customers have ever made was the famous couch watch.
As the story goes, the customer found a famous Paul Newman Rolex 6241 Daytona in a couch that she bought at a swap meet for $25. She didn’t discover the watch until years later. Today, that Daytona trades hands for at least $200k. It’s an investment that changed her life.
RED WATCH BANDS
Kevin has an affinity for red watch bands. In fact, if you watch Shark Tank, you might have seen a colorful red watch strap peeking out from under his sleeve.
Although he tried to switch to a different strap color a few seasons in, he eventually stuck to the red option to maintain continuity between seasons. It is now his signature watch strap color.
THE PURCHASE
To conclude our video, Kevin discusses the Patek Philippe 175th anniversary Worldtimer that he purchased from us here at Bob’s Watches. Check out the upcoming season of Shark Tank to see it on his wrist, complete with a red strap, of course.

[@MDchaz]

$12,000 for a green Oyster Perpetual is very affordable???? First off, their website has the watch listed at 20k. Crazy world we’re living in. There are a lot of great brands out there people. Be original.

[@codys5727]

I like the setup of this channel but they gargle Rolex' balls. It wouls be nice if they could actually promote the Tudor, Longines, Oris and other companies who make great quality watches for a more attainable price point.

[@kevinc1001]

Yes $12k is affordable if your making millions lol

[@bdg5593]

@@codys5727 FACTS

[@davidm4099]

I feel omegas look way better than Rolexes

[@f5garage401]

Rolex at retail is relatively affordable. On the secondary market no way.

[@Storm762x39]

Affordability is a matter of perspective.

[@gregentwistle5105]

Great episode guys!

[@512TXSDIY]

Good video. Each section was a bit rushed to me and could have transitioned better. I personally worked my way to a Rolex eventually. I will say, it is probably one of the only brands that actually retains and increases in value. ORIS is awesome too!

[@sylinmino]

A starter watch is sub-300, maybe sub-500, maaaaaybe sub-1000. Not sub-10k lol.

[@Storm762x39]

Agreed! This is crazy.

[@joshuamclaren7529]

Lol right? Obviously affordability is subjective but to the average person sub 10k is nowhere near “affordable”

[@stoneriverwatches]

Kevin I love you but c’mon, let the man talk

[@jimlittle5769]

Rolex is entry level? Yeah, okay. Most fellow collectors I chat with say 1K or less are starter watches. IMO, it's a huge stretch to say a watch even at 5k is entry level so Rolex OPs (the least expensive Rolex) aren't even 5k or less at MSRP and way more in grey/used market. This is what happens when you get an ultra-rich watch investor on the show. His concept of things like entry level are outside reality.

[@Storm762x39]

Yeah it's so out of touch and ridiculous! Rolex is "affordable".

[@sootherelax2802]

If you get them at retail they are decently priced!

[@jimlittle5769]

@@sootherelax2802 No one said otherwise, still doesn't mean that any of their pieces are entry-level into the hobby.

[@sootherelax2802]

@@jimlittle5769 agreed. I just buy what I like. People are getting into investments. Buy what you like don't treat it as an investment. That's my rule

[@kahuhipajae4088]

Another great interview, best part was no Uhh.. and uhms.

[@bobswatches]

Thanks for watching!

[@Audi_All_Day]

Did the video transitions scare any other headphone users 😂

[@aovermont]

Anything Kevin says is super cool. I'm listening! Thanks for this amazing vid

[@bobswatches]

Thanks for the support! We're glad you liked it 😊

[@pomposso_typer]

What are these watches an entry to? I feel like I'm missing a context for this.

[@minibus1351]

$10,000 for yellow dial OP?! Is this an ancient video or is he misinformed. I'll take 5 if its $10,000

[@WatchFlares]

Can't stand that guy. Mr wonderful? Give me a break. At least he didn't say Maison ;)

[@boomdaus]

I hate this entry level rolex is tudor by definition. Longiness, used omega, tudor, tissot prx, hamilton field khaki. I have stated brands primarily in the swatch group as they are good buys used or new due to the serviceabilty but oris heritage is also fantastic shout. These brands stated have the history, quilty and most of them have the dail or are built for purpose. I am looking for my first automatic to either be a used blackbay, or a cotton candy on a leather strap. I love the fact that Oris is a independent and I would be able to pull of the blue cotton candy, I also love the blackbay representing early subs while having a modern movement inside.

[@bobswatches]

Thank you for sharing and for tuning in!

[@throwawaybruh7518]

Just buy what you like and enjoy looking at everyday. Don't worry about the brand.

[@jodysilvia2]

Kevin would you be willing to collaborate with Teddy on another rap song about watches.?

[@omarfassifihri288]

Lebron who worr the coral AP not JayZ

[@Heater-lk7fc]

Hahahaha. Starter ?

[@anthonyferretti737]

What’s on his right wrist

[@gautam9]

what's on Kevin's right wrist?

[@f1shf1ngers24]

a G-Shock

[@TRUYORK718]

Orient Bambino

[@LAbigsnoopac]

Explorer is the best Rolex and it’s affordable

[@MultiTictock]

bob get someone who can hold a room and good on camera.

[@Alexxtooraw]

Is Bobs watches Legit ?

[@kevinc1001]

I guess their definition of affordable only applies to the rich. I can't afford a Rolex regardless of Price.

[@Thankyou_3]

😂 Two used car salesperson trying to get into the horology game.

[@allosaurusfragilis7782]

Sorry, I don't care who you are, two watches is just silly. I don't know why but it bugs me.

[@stevieglasgowttlreem]

Every watch Kevin brought apart from the Rolex looked cheap and horrible