Kevin "Mr. Wonderful" O'Leary's Fine Wines
Momtrepreneurs, listen up.
Happy new years everyone. My festivities were foiled by finding out that I am, in true Jewish fashion, violently lactose intolerant. Call it Monty Zuma’s revenge.
Kevin O’Leary, aka Mr. Wonderful, is the brash businessman/Canadian on Shark Tank.
Oh Shark Tank. Shark Tank is the show your mother watches, lying prone, 6 crushed Miller Lite cans on either side of her, room completely dark except for the flicker of the TV screen. “Don’t take Robert’s deal…” she slurs and passes out. Left tit exposed. It is 4 PM. We can all relate, right?
The show’s panel of baby boomer businesspeople is so horny. Barbara Corcoran wants to jump the bones of any man with a pulse. Foxy “Queen of QVC” Lori Grenier has definitely given Mark Cuban a handy in his dressing room. Robert watched.
Shark Tank isn’t how business works — I’m guessing — but its ability to give venture capitalism any amount of narrative tension is compelling. Tank Watchers regularly find themselves caring about the freezer aisle shelf space at four partnering Walmarts in central Missouri. It’s fun watching husband and wife teams sob about selling everything because they believe so deeply in their product (flip flops for brunettes).
Mr. Wonderful is the most eccentric of the bunch. His deals are always the most predatory. But I think he’s the most discerning. He’s not going to invest in just ANY truffle hot sauce brand.
Kevin O’Leary made his fortune in the 1980s from a limited term, multi-capital ETF share fund reverse mortgage acquisition dividend blah blah blah buy buy buy, sell sell sell.
All of that is to say he is rich. Rich enough that he and his wife killed someone with their boat in 2019 and got away with it. A classic oopsies situation.
But this is not to say he’s just some dry hedge fund technocrat who devours small businesses like the suckling pig he’s about to eat. Nor is he a maniacal techno-futurist on his way to Mars.
He’s somewhere in the middle. Kevin has an old-school air of backroom dealings, cigar smoke and casual sexual harassment I find so fascinating. He definitely only hires female assistants and calls them secretaries.
He’s but a silly boy! He loves doing photoshoots with his objects like he’s a bald Barbie. Here he is strumming Carlos Santana’s guitar:
Here he is wearing a little chef’s hat and munching on a carrot like a cigar:
I find it all incredibly adorable. He is a man-child, wealthy enough to afford nonsensical purchases but not wealthy enough to be above bragging about them.
And that type of showmanship is the reason he has become a compelling business personality. Even he will tell you business is mostly about acting. But in reality, this may just be hiding the fact he’s a huckster.
Exhibit A: he’s big into crypto. In August of 2021, Kevin was paid $15 million to be an ambassador for the crypto company FTX. That’s right: the one Sam Bankman-Fried is currently facing 115 years in prison over for allegedly defrauding customers. Another classic case of: oopsies!
It’s all a bit pyramid scheme-y: Follow these steps and you too can lead the good life. But unlike other quasi business scammers, his idea of the good life actually sounds good. It’s not just owning a McMansion outside San Antonio. He collects pens. He knows how to pronounce Gstaad. And then there is the wine…
Mr. Wonderful is a bonafide wine aficionado. He talks about wine with an ease and elegance that seems like the only authentic thing about him.
He is part of the secret fraternity Confrérie des Chevaliers du Tastevin, an international association of Burgundy wine enthusiasts. The Confrérie is his baby. In publicity photos with his wine, he is always wearing a beret, jean jacket and, around his neck, a tastevin: the silver drinking vessel mandated by the organization. I mean always. Again, adorable.
The model for O’Leary Fine Wines is quite different than what we’ve seen from other celebrity ventures. In addition to his own label, his website essentially acts as an aggregator of other Mr. Wonderful-approved bottles. Basically it is his own Bevmo, partnering with Vintage Wine Estates for use of their catalogue. He makes videos for each wine explaining their significance, an honestly brilliant way of giving customers context for what they are drinking. As he told Wine Spectator, “This is not me slapping my name on a brand. This is me.”
Despite belonging to a French wine/sex cult, Kevin chooses all of his wines from California. His motto of “affordable luxury” feels accurate: despite the low(ish) price, he uses nonsensical wine words like “palate-roping” to describe $17 Malbecs. That is no small feat, making shitty wines feel expensive, exclusive. Like he does on Shark Tank, Kevin democratizes a strata of wealth off-limits to most. But like he also does in business, he might just be Madoff-ing us: pawning off over-priced wines on the back of his larger-than-life persona.
It worked on me. Looking at the promotional material, I was excited to try these wines. But I have to be honest, I would not give a 30% stake for $100,000 for any of the wines I tried this week.
I started with the B.R. Cohn Sauvignon Blanc ($17). There was nothing interesting about this wine. It had none of the crispness, none of the vibrant grassiness, of an easy-drinking sauvignon blanc. It was just dull.
Then there was the Cigar Cabernet Sauvignon ($22) which Mr. Wonderful says is “the essence of America.” Bald eagle is shaking! The wine is aged in bourbon barrels, giving it a really charred and heavy taste that blew out the personality of the grape.
Then there was the Cherry Pie Pinot Noir ($20), which Mr. Wonderful says is “legendary for its barnyard insult.” There was a waxy quality to this wine, like play-doh. But by the end of the video, Kevin starts choking up. “There’s nothing better on earth than a pinot noir,” he says, crying. I can no longer tell if it is adorable or not.
To quote Shark Tank — for that reason: I’m out.