Erin Lowry from Broke Millennial learned early on about investing. As someone who’s VERY conservative and not excited about losses, she didn’t want much to do with investing. But, she’ll tell us the story today about how she got started and about how you can make it easy. We’ll talk about the types of funds to simplify your investment choices, how to add money, and what to do if the market isn’t your friend (things start to fall apart).

Plus, in our headlines segment, one man who called the last two market downturns says there’s another on the way. Should we be preparing for choppy waters?

Later on, we’ll throw out the Haven Life Line to Larry, whose emergency fund has been drained after a few back-to-back expenses. Should Larry get his emergency fund back to capacity over time, or look towards his Roth IRA contributions to speed up the process? And in our letters segment, Brian has took a side gig delivering food for Uber Eats. After talking to some of his fellow drivers Brain is suspicious that they’re defrauding the IRS by not paying any taxes on their earnings. Should Brian steer clear of their advice, or is he just missing out on easy money?

As always, we’ll still save some time for Doug’s trivia…which today is exceptionally epic.

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<6:02> Headlines

• Man credited with calling the 2008 crisis says the next 20 years in the stock market will ‘break a lot of hearts’ (MarketWatch)
• How To Use The “Scaling Method” To Make Your Money & Fitness Goals Work For You (The Financial Diet)

<20:18> Erin Lowry

<39:03> Doug’s Trivia

• The Greek goddess Iris was associated with what?

<44:12> Haven Life Line

• Larry had a nice emergency fund built up, but a few different expenses has drained his account. Should he drop his contributions to his 401k to the company match (from 10% to 6%) and slowly build back up his fund, or maybe take his Roth IRA contributions and use that cash instead? Thoughts?

<49:55> Letter

Brian took a side-job delivering food for Uber Eats to help pay down his debt. He’s heard some other drivers claim they pay close to nothing in taxes each year. Are they scamming the IRS? You can read Brian’s letter in full below:

Hey guys, I’m a fan of the show even though much of what you talk about is irrelevant to me at this point in my financial journey due to the amount of debt that I am in. As of about 3-4 months ago, I was $8,500 in credit card debt, $7,500 in auto loan debt, and $7,500 in student loan debt.

I decided to do something about it and at this point I have knocked down the credit card debt to about $2,500 (auto loan and student loan are next!). At this point, I am an HVAC technician and I deliver food with Uber Eats after my shift. I have been working somewhere between 60-80 hours a week for the past few months in my efforts to pay down my debt…it is exhausting. Anyways, my question is this…I have spoken with several other Uber drivers that claim to pay essentially zero dollars in taxes each year, while I always end up paying somewhere between 10-15% (after deducting my mileage from the year).

I’m fairly certain that these drivers are scamming the IRS, but I just wanted to make sure that I am not missing anything. From what I understand, you are able to EITHER deduct your mileage (along with a few minor expenses such as part of your cell phone bill, interest paid on a car loan, parking, tolls, etc.) OR your actual expenses from the year (gas, repairs, maintenance, etc.).

I have spoken to at least one driver that deducts both and he said that his accountant instructed him to do so, but I’m not looking to get into trouble with the IRS.

And yes, I realize I could just pay an accountant to answer this question for me, but I thought you guys might be cheaper! Thanks for always keeping things entertaining while I deliver meal after meal…after meal after meal. But seriously, thanks for the motivation!

Join us Friday!