Everyone I've ever dated (before my second marriage) was just practice. Telling my second grade crush I was in love with her and getting laughed at - practice. Posing as a psychic on Craigslist to meet women - practice. I could have chosen not to do those things. I could have been too embarrassed or said I don't want to be "that guy." But then I would have been holding myself back. Don't waste time and energy contemplating if you'll be successful. I get it. You're afraid. You don't want to get stuck or let go of a good thing. Recognize, though, that your fear won't generate wealth and freedom. So how do you know what's right financially? My guest today, Kevin O'Leary says, "There's no guarantee. You have to try things." Before becoming a successful entrepreneur, venture capitalist, and millionaire shark, Kevin tried and tested different jobs. He picked up garbage. This wasn't for him. He wasn't invested. Sometimes the key to success is to say no. Not to invest. If you aren't invested, you can keep trying new things. That's what Kevin did. He tried something else, which he talks about in today's interview. He just kept going. The idea is to find something more fulfilling. And even when you find it, keep an open mind. It might still be a test. Kevin has a three-year rule. If something can't survive three years, then "take it behind the barn and shoot it," he says. Dump it. Quit it. Do not invest. "Unless it's a hobby and you don't mind losing money," he says. This rule applies to dating, too. If you don't see a future with someone, why continue? Consider how much you're spending, or "investing," in dating someone. And think of it the other way around. Can you survive it for three years? Or three more years? Kevin waited six before marrying Linda. Now they've been married for 25 years. In his new book, Cold Hard Truth On Men, Women, and Money: 50 Common Money Mistakes and How to Fix Them, and in today's interview, Kevin teaches you how to avoid making bad investments in your life with simple, easy-to-follow tips. Smart investments require time. You need time to find out who and what you're compatible with. And those things change. You change. So when you feel stuck or unfulfilled, don't just cry about it. "There's no room for tears," Mr. Wonderful says. Do something. Listen today to learn the best techniques to test a potential investment. You'll also hear Kevin's advice on how to successfully get people invested in you. ------------What do YOU think of the show? Head to JamesAltucherShow.com/listeners and fill out a short survey that will help us better tailor the podcast to our audience!Are you interested in getting direct answers from James about your question on a podcast? Go to JamesAltucherShow.com/AskAltucher and send in your questions to be answered on the air!------------Visit Notepd.com to read our idea lists & sign up to create your own!My new book, Skip the Line, is out! Make sure you get a copy wherever books are sold!Join the You Should Run for President 2.0 Facebook Group, where we discuss why you should run for President.I write about all my podcasts! Check out the full post and learn what I learned at jamesaltuchershow.com------------Thank you so much for listening! If you like this episode, please rate, review, and subscribe to "The James Altucher Show" wherever you get your podcasts: Apple PodcastsiHeart RadioSpotifyFollow me on social media:YouTubeTwitterFacebookLinkedIn See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.