Uber Comes to Boston, Getting Started As a Driver

Uber App Showing Surge Priced Area

Uber arrived in Boston around 2011. This was two years after the company originally began as “UberCab” back in 2009.  The company got started because one of the original founders, Garrett Camp, paid $800 for a private car service and was pissed.  He wanted to do better.  You can read the Uber history on Wikipedia.

As noted in a previous post, I got my own start with Uber back in 2014.  Actually, it was around Thanksgiving of 2013, five years ago.  Browsing Facebook, I saw an ad that said I could make $25/hr. driving part-time for Uber.  "What the heck?" I thought.

Driving for Uber and later Lyft has been a social experiment of sorts.  It’s been one of the most unique jobs I’ve ever experienced.   No supervisor.  Work when you want.  And you can take self-imposed breaks where you determine the length.  You can do this between each and every ride you give.  You get paid daily.  These days, you can get paid up to five times a day.   And all I do is sit around talking to people all day, while driving them around, of course.

It was not so easy when I got started.  It took me a long time to get used to doing this.  Only now, five years later, can I say it’s duck soup—or should I say clam chowder?   Being an Uber driver is a job that requires a lot of hard work and concentration.  You are doing many things at once. Your job is to be totally responsible for another person’s life. At the same time, you are in Boston, where you have to deal with one of the worst systems of roads in the country. There are some of the worst / most dangerous intersections in the country as well. Plus we host one of the angriest and most aggressive collections of drivers too. Even for a college man like me (with half a master's degree and 20+ years of work experience to boot) this was a tall order.  All this weighed heavily upon me when I first started. It doesn't weigh any less heavily now. But after 6,000 rides, without incident, I feel confident in my ability to protect my passengers, and to have fun at the same time.

While I had heard of Uber in 2013, I didn’t really know what it was all about. On September 19, 2012, The Boston Business Journal reported: “Uber to launch taxi service in Boston today.”  The article noted that service had also started in New York City early that month.  (Wikipedia notes that it was in 35 cities by 2013.   Somewhere else it is referenced that Uber came to Boston in 2011.  So, I'm not 100% on when they actually launched here.)   The company was originally called “UberCab” but the name was shortened in 2012.   One rider told me she once had a ride with the third-ever Uber-driver in Boston.  In the summer of 2017, I met the second-ever Uber driver here.

At first, I was thinking that driving a cab wasn’t something I envisioned as a career.  I was 47 at the time and I was thinking part-time gig.  The ad was certainly intriguing: $25/hr for a part-time job where I would be in control of my hours, driving my own car.  I’ve since learned many things about the cab business that have changed my attitude about all this.  I’ve read that some London cab drivers are making the equivalent of $150,000/yr. I've also learned this is decidedly not a low-brow pursuit.  It is one of the most interesting and thought-filled avocations I've ever undertaken.

When I told all this to a cousin, he noted, “This reminds me of the old lines by Al McGuire : 'I think everyone should go to college and get a degree, then spend six months as a bartender and six months as a cab driver. Then they'd really be educated.'"  Truth from the legendary Marquette basketball coach.

It took me a couple of months to get started.  After I clicked the ad and signed up, I was told I needed to submit several documents such as my driver’s license, registration, etc.  All this bureaucratic crap struck me as too much effort and I went sour on the fantasy of the cab-driving life.  I didn’t want to do this.  So I ended the experiment.

The next day Uber did something that changed my mind. Something clever.  And intrusive.  They began texting me three times a day.  All I needed to do was send in the remaining documents and I’d be good to go, they said.

At first this pissed me off. I had not given them permission to do this.  (Or maybe I did since I didn’t read the fine print of whatever I had signed/submitted on the registration form).  But someone in the Uber business development office was sharp on this one.  They were intent on hooking me, and they prodded me daily in order to keep me going.

Oddly, after a few days of this I became less angered and sort of began to look forward to these texts.  It’s that feeling you get when you are texted by someone.  It makes you perk up for a moment, wondering who it is.  They had succeeded.

Early Uber App ca. 2014. Note: areas in red are "surge priced".

Early Uber App ca. 2014. Note: areas in red are "surge priced".

After a few weeks of this I finally got up the nerve to submit a copy of my driver’s license.  But, once again, I thought I couldn’t go through with it.  Too much work.  I won’t be good at it.  Again, I decided not to pursue it.

But the texts kept coming.  And I didn’t have the nerve or the energy to figure out how to stop them.  Finally, a month later, maybe around January 2014, I got around to scanning and uploading my car registration.  But again, I thought I couldn’t do this.  Something kept dragging me down to make me feel this was going to be way too much work.  I was going to fail. It just seemed so overwhelmingly difficult and daunting. But by sheer will, I kept going despite the seesaw of yes's/no's.

It took until February before I finally got all the documents submitted.  Then in short order Uber notified me that I should come down to their offices downtown for an interview.  On a Sunday, as I recall.

When the time came I drove down to the Financial District to try to find them. I bounced around a couple of streets where I thought the address was, but couldn’t find the office.  Frustrated again, and feeling they were not making this easy for me, I drove home and told myself, again, “Screw this. I don’t want this BS!”

What happened next?  I got an email a day or two later: “Congratulations! You’re hired! ” I’m not kidding. This is how it began.  They were apparently desperate for drivers back then.  They still are today actually.  But they then notified me they were sending a special phone with their app installed which I could use to start driving.  Not to worry--they did do a background check on me.

Wow.  If only all employers could be like this.

In a week or two they sent me a brand new iPhone.  I think I put a deposit down on a credit card for this.  But this was cool.  I opened it up and played with the app.  Seemed complex.  So, I let another week or two pass.  They had some training videos that I dutifully watched.  It was finally starting to seem easy enough. I was a programmer, tech savvy guy.

Costco GPS

Costco GPS

At last, one day I got up the nerve to go out and see how this thing worked.  I bought one of those dashboard cellphone holders, and plunked down $100 on a dashboard GPS at Costco (I later realized I didn’t need it, and ultimately gave it away).  It was snowing heavily, late January 2014, when I drove down to the parking lot at MicroCenter in Cambridge.   I figured this might be a good spot, near Harvard and MIT.  There would probably be people wanting to hail a cab around there.

I nervously turned on the phone, not really knowing what to expect.  I had watched the training video so I had some idea.  But there was still an overwhelming sense that I would seriously screw this up, despite my many years of successful work experience.  It was nerve wracking and it took a leap of faith to actually do this for the first time. 

I turned on the app and took a video of this experience with my own cell phone to record the moment.  I still wasn't really sure what I was looking at or how this worked, but here it is:


One (ping) if by land. Two if by (the) Sea(port). The Millennials are coming!

Paul Revere should have had it so good.