Lyft Cash Chase Adventure Begins

This is the first post on the Lyft side hustle adventure. The question is always, can you really make extra cash with this gig? I have no fucking clue so let’s find out together.

Damon will put his ass in the seat to find out what reality is and if the cash you can make is worth the experience and hassle of doing it.

Starting from absolute scratch, we will follow Damon on this adventure by coming to the PennyStupid website and subscribing to the free email updates. Find out if Damon will fall on his ass or make good side hustle cash.

Is Making Good Money With Lyft, Fact or Fiction?

Like many things in life, you’ll be disappointed if your expectations are too high. But if you have the correct expectations, it can roll out without much trouble or disappointment. That’s our goal here. Smooth and rewarding is the target.

Damon will help us all to learn what to expect by being the guinea pig for us all.

My mental picture of Damon as the guinea pig getting Lyft ready. LOL.

I’ll give this a 50-50 chance of being equal to the Lyft hype and Damon’s expectations.

I can’t wait to follow Damon and discover where all the irritated motherfucker swearing will be released.

We will write about and share all those pain points with you.

Damon’s video teaches you how to apply and what Lyft expects you to drive. A background check is required. Commonsense says you shouldn’t be an accident-prone criminal so that you can pass a background check, and you’ll need to have a halfway decent ride.

However, judging by the Lyft rides I’ve done in the past, halfway descent is not well defined. I once had a Lyft ride in an old Crown Victoria police car. Unfortunately, that one was none of the way decent.

You Don’t Even Need Your Own Car to Start

But the great news is Lyft offers a car rental program that has advantages and makes it Penny Stupid easy to start if you need a car to use without keeping yours clean or beating it up.

They call this the Lyft Express Drive program. Cars are available through Flexdrive and Hertz at the time of this post.

Express Drive Insurance and Maintenance are Included – Hooray!


Like everything else in life, the delicate print matters on what is included for coverage, and local and state rules will apply. When Damon gets a copy of the teeny-tiny print, I’ll read through it and see what surprises it might contain. I’ll post about what I find, so subscribe to the damn site emails to get notified. For more direct details about Lyft Insurance with Express Drive, click here.


If your Express Drive rental car needs maintenance, the rental partner, Hertz, will send you a notice and ask you to get the required maintenance done as soon as possible. If you don’t get the maintenance done, you may have to return the car, so pay attention. You will not be charged for maintenance at an approved vendor. For more details, click here.

Let’s Not Overcomplicate This

The advertised side hustle opportunity with the Lyft Express Drive program and making money with Lyft is, even without a car you can use, you can get started in the next week by giving the car rental partner cash, they hand you a car, and you start driving. Is it really that easy?

Swinging for the Lyft $3,500 Guarantee

Damon has his silvering beard sights set on completing 180 rides in the first 30 days to earn the $3,500 new driver bonus. Will he be able to do it? I can’t wait to find out.

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