Interesting people, places, conversations, experiences & insights brought to you by a guy, who took some time off from corporate enterprise sales to take an Uber sabbatical... and that sabbatical continues 4 years later! ...Please note: Unless a person of fame, I do change the names and all vital particulars that might identify the people I write about (for their privacy).


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KENYA, ORGANIC FARMING & NEWBURY STREET

By
on
April 9, 2018

If you are like me, you would probably wonder, What do Kenya, organic farming and Newbury Street have in common? It feels like one of those questions from standardized testing where you must choose the outlier.  One of the reasons I prefer Uber over Lyft is because unlike Lyft,…


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3 GUYS, 3 ISSUES… ALL WOMEN

By
on
March 29, 2018

It was Friday, my favorite day of the week. I mean, can anything ever go wrong when it’s the day before the weekend?  I usually shut down my Ubering and head home around 2pm, but for some reason after 27 rides that day I decided to pick up one…


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WORD… WHAT DOES IT ALL MEAN?

By
on
March 19, 2018

There I was, recently on a Saturday night, sitting with my adult son and his girlfriend; let’s call them Z & B. Engaged in conversation, Z went and did it, rather he said it… you know, that term that I have been trying to come to peace with for…


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JANICE, OVERCOMING THE ODDS

By
on
March 5, 2018

One of Boston’s major business sectors is in healthcare.  Patients come from all over the world to be treated by the best in this burgeoning industry.  You never really know who you might be picking up at these great hospitals & clinics, and I often wonder are they a…


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BOSTON’S BIGGEST PR PROBLEM…

By
on
February 26, 2018

I am sure you are trying to figure out, what is Boston’s biggest PR problem?  Is it that old stereotype of Boston being racist due to the anti-busing issues of the 70s?  Could it be that Boston is the 4thmost expensive city to live in the USA (and why…


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GRATUITY OF THE BEST KIND!

By
on
February 18, 2018

As soon as Ned (not his real name) got in the car I got this vibe that something was off… way off!  Ned seemed like a normal guy, he was a millennial, kind of hip… he was off to his job as a web developer. We started out with…


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UBER DATING?

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on
February 13, 2018

With Valentine’s Day now here, I felt it was time to discuss an idea I have had floating around in my head for a while… UBER dating! Hey, why not? Uber has moved into other experimental service areas like food & package delivery, transportation by water & air, automated cars, ice cream…


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BERLIN INVASION

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on
February 6, 2018

Sometimes things happen that are so coincidental, you think, Is it just the roll of the dice, or simply fate?  I would have to say that probably 50% of my rides are people from other countries.  People from China & India rank 1 & 2, followed by Europeans, South…


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CONNECTIONS…

By
on
January 30, 2018

Delivering 20-30 passengers a day can lead to many variations of engagement. Here are 3 random rides from last Friday:

1) A POOL CONNECTION

A pool ride or shared ride involves 1 to 4 people going in the same direction.  Many times people will not strike up conversations amongst each…


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DEFENDING UBER

By
on
January 16, 2018

Let’s face it… Uber gets its fare share of bad press!  I am not saying it’s not newsworthy, but it is out of proportion and it sometimes just unjustified.  I often have riders ask me… “Do you also drive for Lyft?”  I reply, “No, why do you ask?”  Many…

Jim
Greater Boston, MA

Long story short: I started with Lyft (4) years ago as a sabbatical from enterprise B2B sales. I did not like Lyft for some of their policies and the way they ran their business so, I switched to Uber which I prefer for many reasons. I have found driving for Uber in Boston to be one of the most engaging gigs I have ever experienced.

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