Kevin O'Leary Interview: Debating Watches as Investments, Discussing the Industry & His Collection

Around 3 months ago I noticed Kevin was posting more watch related content online, with his video discussing watches as investments catching my interest the most. After responding to his video with my own thoughts, I reached out if he would be willing to discuss this further along with other watch related topics. I hope you all enjoy!

Kevin O’Leary YouTube Channel:

Head to my store:

My Instagram:

Bob’s Watches & Teddy Baldassarre Shop:

Watch giveaway:


  1. I could not agree more with Kevin about the Apple watch! And I am an Apple shareholder! I wouldn’t be caught dead with one either! (Well maybe in a gym on a treadmill!) To my way of thinking, there are very few acceptable forms of men’s jewelry. A wedding ring. (Or a Service Academy ring or similar in lieu of.) and a watch. In the conservative South, we don’t wear pinky rings, gold chains, and bracelets. We do wear cufflinks, but not with casual clothes or sport coats. We do appreciate nice pens, and the selection of the pen is given some consideration as well. However, why would I wear a nasty computer on my arm, when I can wear a beautiful Rolex, Patek, Cartier, Omega etc? Why would I want another device that has to be charged all the time? One that will be out of date in three yeas? No way! I’m not giving up valuable real estate to a screen that lights up! Consider this. At least with your phone, you have an excuse for ducking a call for a while. When everyone knows you have that device on your wrist, they know that you have seen the call! And the constant interruptions! OMG! But first and foremost, it is a matter of aesthetics and taste. To each’s own. Not me. Not now. Hopefully not ever!. Nice work, and great video guys! Thanks!

  2. I always hated watches, then I bought an Apple Watch. 2 years later, I started getting into automatic watches. Now, I own multiple high end automatic watches, and some micro brands. I’m obsessed, and it all started with that piece of “consumer electronics” on my wrist. With that being said, I only wear the Apple Watch when working out now.

  3. Does this guy realize how cringey he sounds in every video when he says “my collezione”. Its like guy we get it you like nice watches. Please stop. It’s actually cringeworthy.

  4. I hate Kevin with a passion. He's the embodiment of a super capitalist jerk but I do appreciate his non traditional takes on watches. It's good to have some rich prick like him telling all the wannabes to get off their high horse when it comes to what you can and cannot do with a watch. It's refreshing to see one of the big guys being so open to boldness in a hobby that is so annoyingly uptight.

  5. I still Poopoo the AP RO. If I couldn’t sell it or trade it, I wouldn’t take it for free. It’s an ugly watch in all its forms. IMO. Heresy to many, I know. Sue me.

  6. Watch brands that don't make their own movements are the equivalent of firearm brands that don't make their own barrels. They are essentially furniture assemblers.

  7. What a great interview. I'm not a fan of O'Leary at all, but he def knows his stuff. I'm just surprised he didn't keep his collection in a safety deposit box at the time , but it sounds like it was an inside job both times .

  8. "They did not pay Nadal to wear them." – Ummmmm I think it is widely published that Nadal does get paid to wear Richard Miller. Otherwise nice video.

  9. Nice video !! I am convinced that the poor too could be rich , if they invest wisely and diversify their income. Investment isn’t a get rich scheme but key towards financial growth and stability

  10. Kevin is so miserable to listen to. The red band is so tacky, and matching his pens thinking he’s original. The way he says collection and thinks people care about what he’s wearing on shark tank. Teddy’s comment, “I think it’s a blessing in disguise” shows how repulsed he is by the tacky red bands. Everything Kevin says sounds like something he’s heard someone else say. He’s regurgitating other people’s opinion because his are so miserable. For example, the only original thought he had, was putting red bands on every watch. What an unflattering statement to make on well crafted timepieces. Nitrogen escape valve (you mean helium), Beaumont (you mean Bremont). It’s like he’s so disinterested in his own hobby because he’s so god damn boring and pretentious. I love Teddy, but can’t stand Kevin’s commentary on anything. “Here’s my collection of other people’s favorite watches. I added red straps because I’m a classless moron. The only watch I picked out on my own was a used women’s watch. It’s so stupid that the second time I bought it my wife cried. I also match my watch to the vegetables I’m going to cut next week.” I can’t believe Teddy has the stomach to talk to this man.

  11. It's so true to say it is very hard to 'monetize' your watch collection. I have a couple of steel Rolex's I bought as investments but, despite the prices you see online, the platforms take such a huge % that negates the profit of someone choosing to buy from me.
    Watch dealers look for margins around 45-55% (in my experience) and unless you are buying the sort of watches Kevin talks about – you ain't making any money on 10k watches.

  12. My collectsioon is a beat up Hamilton field watch, a Timex Marlin and a Seagull 1963 hand wind chronograph. They give me the same joy as his does for him but nobody is trying to steal mine. : )

  13. Man you guys are so great together, I can't get enough of these videos, both of you look so good together, your personalities mesh quite well, you're both so knowledgeable, I've been BINGE WATCHING THESE VIDEOS and I can't get enough…. Both of you have great taste in timepieces, you guys both seem to have developed a genuine friendship, and let's face it, we've got two powerhouses from two different generations, which is what the world needs MUCH MORE OF…. And I don't mean this in a bad way AT ALL. Kevin isn't "old" and Teddy isn't a "kid" but there is some distance between the two of your ages, and these videos are a FANTASTIC EXAMPLE of how beneficial a friendship is with a person outside of your age group. One of my longest friends is over a decade older than me, and I could not have possibly been more blessed. I think that's part of why I appreciate these videos so much… you guys, I mean, its the internet, its "tv" but you guys seem to GENUINELY enjoy each other's company, and man, I can't get enough of that….. IF ONLY more people would seek out a solid, genuine friendship like this, the world would absolutely be a better place.

  14. I'm going to piggy back exactly what Teddy is mentioning. It's tough for an upper middle class person to go into VC and buy an overseas. I literally ask and ask and ask…

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