Jennifer Sanasie: Alright, I gotta talk about that background. It just looks so lovely. What? Where? Are you sitting by a pool right now?
Kevin O’Leary: It’s right behind me, it’s the Hamptons. I thought it would celebrate a summertime moment. It’s a great summer we’re having, in particular with crypto policy, so why not enjoy?
JS: Exactly. I am completely with you. Well, honestly, it sounds like you’ve been having a really fun summer. I saw you on stage on Twitter with the Jeff Tuohy band on X just living life, Kevin.
KO: Yeah, I do that every year with Jeff’s band, keeps my chops up. He gets better and better. And of course we celebrate that. I do a lunch every July 5 with Jamie, who started Ring, a very famous Shark Tank deal that got away. He sold it to Amazon for $1.2 billion. We’ve become very close friends. We got our families together and then we went to Cisco Brewery and then I jam on stage. It’s a great time. It’s just a celebration of the 4th.
JS: I’m so happy you brought up Ring because I got to ask you about some of your best and worst investments. Did you invest in Ring?
KO: No, I was the only shark to make him an offer. I thought there’d be a lot of dilution and consequent rounds over and over again. I offered him $600,000 in debt with 2.5% warrants – non-dilutive warrants. He didn’t take that offer. I understand why, but at least he got one. It would have been the biggest outcome in Shark Tank history, but you can’t win them all.
JS: It would have been a good one. When you think back, not only to Shark Tank history, but to your career, what’s the worst investment you’ve ever made?
KO: Well, I’ve made a lot of bad investments, but I’ve gotten better from experience and I’ve learned something interesting. I guess I would call it intuition over time. When you’re writing a check and making an investment and it doesn’t feel right in your stomach, that’s because it isn’t and it’s going to go to zero and it does. And I’ve done that to myself a few times, but now I listen to my innergut on this, which I think is just years of experience. And if it doesn’t feel right, I don’t do it. And it’s, I’ve been very fortunate, you know, I don’t get it right all the time, but I get it right enough that it’s, it’s been an interesting ride. And it’s really your winners that define your success. And I will say one thing about investing to everybody, cause I’ve been doing this a long time. Let’s say I do 10 deals. I’ll do, I’ll probably do 17 deals. The ones I think are gonna be the winners are never the winners. It’s the ones that I think, “that’s a flyer,” that five years later I get 100X, 200X, 300X on. You just don’t know, which is why you need that diversification in your strategy. You need to do more than one, particularly if you’re talking about venture capital. That’s what we’re talking about here. I don’t just do venture, I do private equity, I do debt, I do other things. But on the venture portfolio, it’s high risk and you need diversification.
Source:- yahoo.finance
