I Bought a Car and Started Driving for Sidecar

Sometimes opportunities arise from the strangest circumstances. The story behind how I ended up buying a car could fill an entire post on its own, but I think I’ll save that for another day – or for some catch-up conversation if you haven’t heard about it yet! What’s important is that I recently bought an excellent condition used car from Craigslist, and after a lot of research and deliberation, I decided to become a part-time Sidecar driver.

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The Story

A little over a year ago, I sold my beloved Baxter after moving into the city and coming to terms with the ridiculous parking situation in downtown San Francisco. It was either $350 a month for a public garage or circling the block for nearly non-existent street parking, not to mention very active meter maids and 7 am street cleaning days. So with a heavy heart I sold the Eclipse and never looked back, using plenty of other transportation options to easily get around in the city.

Several months ago, an idea formed in my head. It was a crazy one, for sure, but I was curious about the feasibility of driving for a ridesharing company, since they’re all the rage these days. After some number-crunching and weeks of Craigslist hunting, I pulled the trigger and purchased a very clean and well-taken-care-of black 2002 BMW 330i (E46 generation). It was a steal for the amount of work the previous owner put into it (he was a BMW enthusiast and mechanic), so I was more confident I’d be able to get a good amount of miles out of the twelve-year-old car.

And then I decided to drive for Sidecar. After some paperwork, an interview, and vehicle inspection, I made my first pickup two weeks ago on a Thursday night in the Mission district. Read on for my experience so far!

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What is Sidecar?

Sidecar is a rideshare app similar to Lyft and Uber. It’s been around since 2012 and has been consistently the number three of the popular rideshare apps. With all the hullabaloo going on between the two dominant players in the market, Sidecar has had a hard time getting a lot of love.

Using it is simple – you open the app, the app detects your exact location, and you enter the address of your destination. Sidecar then searches for nearby drivers and generates a list of available drivers as well as the flat rate each driver offers based on vehicle, reviews, and extra features. This sets Sidecar apart from the other rideshare apps, which don’t provide the option of picking your driver or price.

Once you choose your driver and the driver picks you up and drops you off at your location, the payment is taken care of through the app (linked to your credit card, no fumbling for cash). It’s simple, reduces car usage and accidents, and has proven useful time and again (especially after happy hours). There’s no need to flag down a taxi, deal with “broken” credit card machines, or get rejected because you live in the Sunset.

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Why Sidecar?

I like to think of Sidecar as the nerdy sibling of the bunch (with a terrible fashion sense), constantly overshadowed by the pretty eldest sibling and the social middle sibling but secretly very smart and talented. Sidecar has consistently been the most impressive to me in terms of the technology it uses, the features it constantly rolls out, and its propensity (so far) to shy away from drama and shady tactics.

As a regular user of all three ridesharing apps (plus a slew of other promising transportation apps), as well as a life-long lover of anything car-related, I knew I had to go with Sidecar because of its flexibility for both riders and drivers. As a driver, I’d be able to turn on the app and immediately start picking up passengers. And that’s exactly what I did a couple weeks ago, and now I have a side hustle and have been a happy Sidecar driver since!

My Experience So Far

It was a Thursday evening when I finally decided to turn on the Sidecar driver app. It had been a little over a week since I’d been onboarded and I’d already watched the intro and instructional videos. I felt far from ready but took a deep breath before tapping the “Go Online” button. After about a minute, my first ride request came in. My heart beat a bit faster as I accepted it, opened the pickup location on Google Maps, and drove over to a bar in the Mission.

There’s no getting around it – that first ride was awkward about 75% of the trip. I didn’t know whether I should make conversation, turn on the AC, crack the windows open, or play any music. So I just drove in silence for a while, being extra careful not to speed or make sudden stops or turns. But my passenger helped me out by making small talk, and we ended up chatting about beaches in NorCal, SoCal, and Barcelona, where she’s originally from. I dropped her off and she thanked me for the ride, something I definitely wasn’t expecting. Just doing my job, ma’am!

After that, things settled down and I grew much more comfortable. Over the course of several hours, I picked up a group leaving Nightlife at the California Academy of Sciences, chatted with a Google engineer about his job and what it’s like to commute on the Google buses, met a Filipina who confirmed Daly City as the NorCal version of West Covina (woot woot 626!), and ended the evening dropping off a passenger in the beautiful forested area of the Presidio.

The next week, I continued my adventure, picking up my roommate Ryan from work (thanks for the support!), chatting with a couple who were visiting the city, meeting some college students, and discussing clean water solutions in third-world countries, law office stories, hypothetical party situations, and good ol’ Los Angeles weather, to highlight a few of the many interesting conversations I’ve had with really cool people.

Apart from one scary moment when I picked up a drunk person from a bar and lost GPS signal along the way, all my trips were pretty smooth, and even with the GPS issue I eventually found my way to the destination and had a fun conversation about music festivals and concerts with that passenger.

All in all, it’s been an absolute blast to be driving for Sidecar, and despite the tiredness that inevitably comes with driving for long periods of time, it’s the wonderful feeling of finishing the last drop-off of the evening and driving peacefully along the Great Highway next to the ocean that makes me want to go back for more.

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What I Hope to Accomplish

  1. Make $$$ – I’m not going to hide the fact that a large part of this gig is for some extra spending money – I even mentioned this during my interview, and I’m sure it’s the biggest reason why drivers choose to drive for rideshare companies. While I don’t expect to recoup my initial car purchase cost, I hope that this side hustle will help me earn enough to afford owning a car in the city (parking, gas, insurance, maintenance, repairs) as well as some pocket money for future trips or projects.
  2. Meet People – It’s tough meeting people in a big city. People tend to stick within their own established circles, which is a shame since everyone has an amazing story. I’m hoping to meet different people, learn more about life through others, and talk about interesting topics, in a chill, low-pressure setting. Seriously, I love talking to people while I’m driving because there’s no expectation to make eye contact or read body language, which I’m terrible at. Plus I’ll get to practice my patience in the case of meeting drunk passengers.
  3. Get to Know the City – After living in SF for over a year I’m pretty comfortable in my general sense of direction and knowing where a lot of landmarks and neighborhoods are. But these past couple of weeks have shown me just how much more of the city there is left to explore. I’ve brushed up on my knowledge especially in the western parts of SF, which I rarely venture out to, as well as refreshed my memories of popular spots in the Mission, Financial District, and SoMa.
  4. Drive – “I drive” is one of my favorite movie quotes (also what an amazing movie) and defines my life. Driving is one of the most fun and most relaxing things I can do (other than riding my motorcycle). Since high school, I drove my friends around, and now I get paid for it. I’m hoping to spend some more time enjoying my E46 in the years to come!

Drive or Ride with Sidecar!

Now for my (not-so) shameless plug. If you own a 2000 or newer car and any of what I covered in this post interests you, talk to me about driving for Sidecar. Sign up with my driver referral link to get a $50 sign-up bonus and up to $200 if you complete a set amount of rides. It’s no obligation so you can stop driving any time.

If you haven’t used Sidecar before, it’s a pretty awesome and useful app. There’s no surge pricing and the community of drivers and riders is pretty great. Use my rider referral link for $15 to get you started!

In the meantime, I’ll continue driving for a few hours a week, and there may even be additional driving-related projects I plan to take on in the very near future. Stayed tuned for my updates!


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