Perspectives from the Driver’s Seat of Uber (Part 1 of 3)


Until a few months ago, I had been in the driver’s seat of Boloco, the company I helped start, for almost my entire career.  Not surprisingly, moving to the driver’s seat of an UberX vehicle was a very different experience.  In what will be three separate postings over the next three weeks, I’ll share the story of how I got started, the experiences, and the key takeaways. Don’t get your hopes up… nothing super ground-breaking for most of you. Hopefully interesting enough to read from start to finish.

If you are looking for an abridged version written by a professional, see Scott Kirsner’s story on


The message I had been waiting for finally arrived last Thursday.  Via text, of course… from Uber Partners Boston: “Your Friend Shabih has just earned a reward for referring you to drive with Uber.”  I breathed a sigh of relief; my work is done, I thought.  My commitment to my “friend” is now complete.


I met Shabih on the first day of the rest of my life.  It was the “morning after” and I was in Chicago.  In an apparently typical game of chess between a company Founder/CEO and his/her Private Equity sponsors, the evening before, October 6, was my last stand as the leader of my beloved Boloco.  It was clearly checkmate on me. 

My terms of resignation were accepted and as I left the building of my investors on a chilly autumn Sunday evening I wandered a little aimlessly down North Michigan Ave.  I found a place to eat called Doc B’s, really beautifully built as I recall.


Like the streets, Doc B’s was also quiet, with a giant garage door that opened to the street and the weather was just nice enough to have it open.  I ordered my food with the server, but other than that I spoke to nobody that night, not even my wife.  Digesting the fact that I had just left the company I helped start nearly 17 years earlier wasn’t going to be as easy as that delicious burger I enjoyed that evening.  Many challenging days lay ahead of me.

The next morning I walked a few blocks to grab a bite at Protein Bar.  These quasi-competitors of ours had just secured over $20M from an A+ group of investors, Catterton Partners.  Despite a few pimples on their young brand, their growth prospects were brighter than ever.  We, too, had been on the 1-yard line of a similar investment until a week earlier.  But for a variety of well-documented reasons, it wasn’t meant to be.  I ordered a breakfast Bar-rito (spelling correct) which I found adequate, and then tapped my iPhone for an UberX car to take me to O’Hare.  We found each other quickly.  Time to head home.


“How’s Uber?!” I asked my driver, as we made our way west to the airport.  I always ask the Uber drivers that… I am always genuinely interested.  I love Uber.  I’ve loved it since the night I first used it to take my then 8-year old daughter Tibby to that memorable playoff game between the Pats and the Ravens… the one where the Ravens missed the field goal at the last minute and we went on to win the game (see that epic moment here). 

I’ve not just loved Uber; I’ve been obsessed with it.  And of course, like many other brilliant businesses I’ve fallen for, I always pondered why I hadn’t started it, since of course I had thought of it before!

As proof of my loyalty to Uber, I looked at my Uber rider dashboard recently and was proud and at the same time horrified to learn that I’ve spent $5,581.80 with Uber on exactly 168 trips since January 2012. In the beginning it was all Uber Black because that’s all there was – and it was costly - but now it’s almost all UberX, because it’s so damn cheap – about 20% less than cabs.  When I’m traveling with the whole family we’ll use the Uber SUV option, especially to and from airports, and when I want to feel like a big shot for a minute (burrito guys need superficial boosts in confidence every so often) I’ll still do Uber Black once in a blue moon.  Having now spent an average of $33.22 per trip, I think I’m close to where I would have anyway by taking cabs the whole time.  If it is slightly more, it’s been worth every penny.

 “I love Uber”, replied my driver.  “It’s the very best.  After I drop you at the airport, I’ll head home and grab some breakfast and then go back out and do some more.  It is great.” 

“I should do Uber,” I said.  “I love Uber.”

“If you do Uber, and you let me refer you, I’ll get $250 for referring you”, said the driver, Shabih.  (See the actual conversation here)

Without hesitation, I knew what my first post-Boloco project would be. 

“I’m in.  I’ll do it.  It’s the first day of the rest of my life.  This is a no-brainer,” I replied.  The words and the commitment presented themselves so naturally.  I wanted to do it.  It was totally different.  Not only that, but this, my first day out of work, and boom!  I was on the move again.  I was… “leaning in”?! … Watch out, I thought, Pepper is back! There would be no limits to my exploration of new consumer and consumer tech services.  I was free to explore, to leap.  Before that plane took off for Boston, I was signed up using Shabih’s referral code.  A few simple steps and I’d be driving and Shabih would be $250 richer.


Nearly a month later, after ignoring most of the Uber texts and emails urging me to come in for my “interview”, I finally responded and agreed to an October 30 Uber “open house.”  Not yet having told my wife what I was up to, I told her I was grabbing a drink with the former head honcho of Bertucci’s – a friend and the perfect alibi for my side project.  When I arrived at the Holiday Inn in Dorchester right off I-93, with my perfectly clean 2012 Jeep Wrangler ready for the assumed inspection, at least 50 and maybe 100 nearly all male waited in the lobby.  There were a few other Caucasian guys in the mix, but I was clearly in the minority.  I hate to admit that I felt mildly uncomfortable… and almost left as a result –an entirely different topic, of course.

We finally filed into a conference room (again, see this link for actual footage) where we checked in with one of the hip young Uber team members sporting lap tops and casual wear.  Come to think of it, I think I had my lap top with me and was also pretty casual.  It was a good fit already.  I was all set with my online paperwork, so I took a seat in one of the many chairs laid out in a few rows facing a small projector, portable speakers and a screen.  It took about 20 minutes to get everyone properly registered and seated. 


The training film was adequately professional although the sound quality junior varsity at best.  We were instructed on the basics of being an Uber driver.  The video part lasted about 20 minutes.  What followed was a brilliant 40 minutes of Q&A.  Whatever it is that was actually asked, I came away from that short session with only a few takeaways. 

1)   The customer is always right; and on that note, default to giving them a 5.0 rating.

2)   Expectations and benchmarks for success were made crystal clear. Uber takes its rating system very, very seriously.  Stay above a 4.5 rating and you’re fine.  Fall below and you face removal from the system.  No stories.  No excuses.  No phone calls.  

3)   Never, ever try to call Uber with problems… because they don’t officially have phones and there is very little if any reason to talk to them. Email them if there’s a problem.

As I got ready to leave the “training” program a few minutes early (I had a date with my wife), they snapped my mug shot, issued me my phone, a minute of friendly chit chat, and off I went.


Maggie was having a drink with a good friend when I arrived at the restaurant.  “How was the Bertucci’s guy?” she asked.  I confessed nearly immediately.  Maggie’s friend cheered and wanted to Instagram my Uber portrait on the spot.  But when I looked at Maggie, there were tears in her eyes.  She was quite upset, mostly for fear of random strangers entering my car, safety, etc.  This was not a chapter in her burrito magnate storyline she had ever thought could exist. 

It took me a few more weeks to get the nerve to hit the “go online” button.  I was nervous. It was a Saturday morning after my oldest daughter Tibby’s soccer game had ended and she convinced me that it was time… 





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