Watch Shopping With Kevin O'Leary - Building A 5 Watch Collection (Unlimited Budget)

In this video, Kevin and I descend upon Watches Of Switzerland in New York City for a little competitive watch shopping with an unlimited budget. After you watch the video, let us know who you think had the better collection down in the comments!

Videos Mentioned:

[j.burgess]

I think I understand why Kevin was such a winner in business: he has the rare ability to be both likeable and an A-hole at the same time.

[danw]

Fun Fact: the sales associate helping you is Kelly Yoch, who used to be the allocator of the Tiffany dial Patek Philippes, and literally has a fan club of billionaire watch collectors.

[rafidbinsadeque]

In every collab video
Teddy explaining all the ins, outs and details of everything.
Kevin: that's a classic.

[drybrusheverything]

Kevin actually won this one, especially before the swap at the end. The collection is super cohesive, has a family feel and the GP really rounded it off well with a bit of flavour. Well done old boy.
Teddy don't feel too bad, you usually decimate him hahaha.
A great YouTube watch duo with powerfully contrasting perspectives but complementary alignment on the artistic and philosophical side of the hobby. So sick.

[UltraDoug]

Seriously, these collabs need to be created at LEAST once a month, if not biweekly or weekly. So good.

[frederickboulton]

Teddy's watches individually are great picks and I can see myself choosing them too. However, when seeing Mr. Wonderful's final collection side by side by side, my heart fluttered. Mr.W has this win in my book.

[victorl]

Not the biggest O’Leary fan, but Teddy knows how to have fun with Kevin and I love these “shopping” competition videos between these two. Awesome job Teddy.

[cxcookie]

The fun you two have together is so palpable and enjoyable to watch!!!

[philorgneopolotin]

The dynamic duo is back! Gotta say, this is by far one of my favorite series on this channel. If it were up to me we’d be getting one of these on a weekly basis. I just can’t get enough of watching you two banter about watches like an old married couple 😂

[vakuzar]

Usually I like Teddi's collection more, but this time Kevin wiped the floor!

Worst part? You gave him his best piece!

[JoLap]

Good God, these collaborations have always relaxed and de-stressed me more than therapy. Love the appreciation of watches and horological beauty, complexity of the movements and quality of dials, the history and the insight into the economics of the watch market. Thanks Ted!

[dotcomma]

It was really a close one. Kevin is right it looks like a family, it’s cohesive and feels more of a capsule collection. Though I’ve always preferred Teddy’s collection but this time Kevin has that marginal lead. Great video Teddy! Always a pleasure to see both of you.

[funkdebris]

Met Teddy the day before this shoot at Watches of Switzerland SoHo (Kelly was there too!)… he was such a nice guy. Stopped what he was doing and took 10 min to talk to me and give his perspective on my collection and what I might consider next. Thanks for the great content and your passion for the hobby!

[dshindo]

I think Kevin’s collection is a more fashionable selection, while Teddy’s is a well rounded collection. That being said I could see myself with Kevin’s picks. In reality you can’t go wrong with either. Its my birthday today so I bought what my wallet would let me . I purchased a Longines HydroConquest black on black ceramic 😊. Thanks for the fun content you make quite a team

[moemotors]

I love Kevin's reaction whenever he sees Grand Seiko! Goes to show his love and affinity to such a stellar brand. 10:15

[jessemitchell]

Amazing series. Love you both. Would love to see an episode where you both make your choices independently. Neither seeing the other's choices until the end.

[MarkFenimore]

I actually like the cohesion of Kevin's collection after the last minute swap! I'm giving the W to Mr. W. Great show guys much love to you both for indulging us!

[BC-jsrp]

When Kevin picked the Oris, I looked down at my own wrist and swelled up with pride. I literally yelled, “yes!” I proudly wear a Roberto Clemente BCPD as my everyday watch. Such a romantic piece. I’m sorry, Teddy, Kevin knocked this one out of the park 🏟️⚾️🧢

[jmrriver]

Kevin definitely won this battle: the Omega black and gold combination it’s a killer, the ORIS Roberto Clemente edition is unique, and the JLC it’s so classic beautiful and complex at the same time. In my opinion, these three pieces moved the balance into Kevin‘s favor. That Grand Seiko is such a beautiful piece.

[aaronnikolai]

Love when Kevin picks a watch that’s on your wrist while you watch the video, love this Seamaster! Great video as always