How does a guy with a great job at Facebook end up as a standup comedian? Today we talk to Paul Ollinger, the 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 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.

Show Notes:

Clearbanc

Thanks to Clearbanc for supporting our show. If you’re doing over $10,000 a month in revenue, find out how you can receive Clearbanc capital by getting your 20 minute term sheet at clearbanc.com/SB.

Check out Clearbanc

HoneyBook

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

Check out HoneyBook

<> Headlines

• Why It’s Better to Invest Conservatively Now Than to Average-In (Of Dollars And Data)
• What retirement crisis? Number of 401(k) and IRA millionaires hits record high (MarketWatch)

<> Paul Ollinger

You can find more from Paul (and his podcast!) at: PaulOllinger.com

<> Doug’s Trivia

• What is the name of the immensely popular fall drink that netted Starbucks $110 million last in 2018?

<> Haven Life Line

• Maddox wonders what he should do better with his money. He’s a college student that’s actually turning a profit while he’s in school, and already has a firm base-level investment plan. Should he diversify more?

Want the guys to answer your question? You can call into the Haven Life Line and get your question answered on-air HERE.

Join us Wednesday!

We’ll be joined by best-selling author Colleen Bordeaux. Colleen is a fantastic author who’s written a best-selling philosophical guide on how to handle life in the age of overwhelm.