How does a guy with a great job at Facebook end up as a standup comedian? Today we talk to Paul Ollinger, host of the new Crazy Money podcast, about chasing your dream...in his case, the dream of becoming a comedian. It's a compelling conversation if you've ever hit the wall with your career, or you've ever made a spur-of-the-moment decision, or you realized that you needed to sharpen the saw to get where you wanted to go. There's something for everyone in today's interview.

During our headlines segment, one recent piece takes to task the age-old idea of dollar-cost averaging. Should you do it? You'll be surprised with the results. Plus, do you think becoming a millionaire is out of your reach? I think you're going to love the great news we have for you. With some sound investment strategies and saving your cash, you could find yourself among that list too.

On the Haven Life line call, we talk to Maddox, who's wondering what he should do better with his money. He's a college student (and actually turning a profit while in school!), and already has a firm base-level investment plan. Should he diversify more? We'll weigh in, and of course, we'll have time for Doug's trivia.

Thanks to Clearbanc for supporting our show. Thanks to Clearbanc for supporting our show. Go to clearbanc.com/SB to sign up today to get $1,000 of additional capital if you are approved as a qualifying company.

Thanks to HoneyBook for supporting Stacking Benjamins. Go to HoneyBook.com/sb for 50% off your first year.

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