Why Uber symbolizes everything wrong with tech today

Note: the views expressed here are my own opinions and do not reflect my employers, past or present. Also, yes – the title is clickbait. 😛

I have a problem I need to confront. When I need to get somewhere in a hurry, I will almost never use a ridesharing service – particularly Uber. Even if it’s 2am and I’m far from home after a night out on the town. Even if 6 of my friends all get in one, I will be the one hold-out that opts to find some other means of transportation. Even if it means that it takes me twice as long to get where I’m going. Even if it means I’m late to my own birthday party. 😛 I’m just that stubborn.

Why is this? I believe I’ve developed something akin to an allergic reaction to ridesharing services – and I believe that actions by Uber throughout its ascent have played a major part in this.

I’ll admit this strikes many people as peculiar. After all, I live and work in cities where Uber is hugely popular with my peers. I also work as a product manager in the tech sector and Uber is universally praised as a true “disruptor” here – being one of those standout companies that identified real problems with taxis and delivered a true innovation to market, decimating incumbents in the process. Travis Kalanick is certainly a hero to many, and his company’s success is not completely undeserved.

However, a great product does not exclusively define a great company. Other factors play into my mindset around this. Here I attempt to explain – both to myself and friends who wonder – each of my concerns with Uber. But first, in each case, noting that my concerns are actually systemic problems across the tech industry – which again, I’m part of!

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Musings in Montréal

I had the pleasure of swinging by Montréal recently and a thought dawned on me: it had been quite a while since I visited a city that was truly new to me. I had gotten stuck in a routine of repeat visits to cities and countries I’ve been to before (all which I loved) – but I had forgotten what it was like to dive into a place where I had no idea what to expect and no pre-conceived notion of its history or culture.

I have to admit, the prospect of a whole new playground to explore gave me quite the rush. And not just because it was in Canada. 😉

As is tradition when I visit major destinations for the first time, I present this documentation of my exploration in superlative form. Locals may not agree and this list is definitely not comprehensive, but it is what I’ll remember from this latest trailblazing effort in Montréal, the “Paris of the North”.

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Notable quotes from The 4-Hour Workweek

People sometimes tell me that I should follow in the footsteps of author Tim Ferriss, given my penchant for travel and remote work. I have a couple of qualms with this:

  1. In my opinion, Tim Ferriss often comes off as a douche – in both speaking engagements and in writing. I’m sure he has good intentions to help people – but his delivery of advice is a mix of humblebragging (look at all this cool shit I’m doing) and light condescension of people living “normal lives” (what you can’t pull this off?). I was looking for a clip of him speaking that exemplifies this, but I think this will do:



    I know I can be pretentious at times, too – but at least I try to catch myself and would hope I never get to Tim Ferriss’ level of aggrandizement.
  2. Tim Ferriss advocates for a world where no one actively works on building or maintaining anything. He would have you create something once and passively sell it forever, thinking as little as possible about improving it or creating new products. All while outsourcing your tedious tasks to some poor folks in India.

    This bothers me mostly because I am a product manager – and no half-decent PM would release a v1 without some sort of long-term vision or roadmap for where the product should go. I am also a very hands-on PM, so the idea of letting someone else manage my inbox makes me nervous.

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