Be the Dragon TourWith great anticipation, I boarded a flight to Toronto for the last stop on our “Be The Dragon” investor tour last Monday morning. Oddly, for a Calgarian, I love visiting the city, having spent much of my career commuting back and forth and I always enjoy returning to my local hangouts when I’m in town. Although I have been on an AirBnB streak for quite some time, I couldn’t seem to find one that was convenient to the financial district so I used one of my favorite apps, Hotel Tonight, to book the Hotel Victoria, a gem of a hotel located at Yonge and King.

The four hour flight gave me time to finish my presentation for the Dragon event and on arrival, I boarded the UP headed to Union Station, then had an easy two block walk to the Hotel Victoria. I walked the short distance to my first meeting, cursing the fact that I had just left a warm and balmy Calgary for a snowy and cool Toronto. After my meeting I ordered up my first Uber ride. My driver, a young entrepreneur that wanted me to convince his wife to move to Calgary as he had just read that the single housing market in Toronto was out of reach for most millennials, took me to a dinner meeting with a client, where I struggled with an “all meat” menu for my pescatarian palette! After a fun night, my client graciously drove me to my hotel and I settled in for the night.

Since my hotel was centrally located in the financial district I set out to take the subway to my first meeting, only to find that the TTC was not running due to an electrical fire, so once again, ordered up an Uber to take me to my meeting. Driver #2 had only been driving for a few weeks, but shared his enthusiasm for the part time gig, allowing him to work on his tech start-up while earning money to pay the bills as he pursues his dream. With the TTC back up and running, I took the subway to my next meeting, quite pleased that I actually emerged near the entrance of the meeting address.

After a great meeting discussing the disruption of fintech in the private capital markets, my host and I set out to walk through the blustery streets to our restaurant reservation at Ki, one of my favorite spots, especially when the host pays (thanks RP)! After dinner, with the snow blowing like crazy, I decide to hire an Uber for my trip home only to realize that I was only a couple of blocks from my hotel so I sucked it up, put my head down and walked through the snow to my hotel.

Spoke Club

The Spoke Club – Toronto

The next morning was the day of the Dragon event. I was concerned that the weather would affect the attendance, but was also secretly hoping it would, as we were incredibly over sold at that time. I hired an Uber and headed across town to the Spoke Club to check out the venue and settle some last minute logistics. Let me tell you, I love the Spoke Club. The entire team was more than accommodating and the vibe was exactly what I was looking for. After a quick check on the space, I ran out to meet with one of Toronto’s leading Angel groups to talk about the blurring lines between investment crowdfunding and other stakeholders like Angel groups and early stage VCs.

The Dragon event attracted a full house of Angels, first time investors, entrepreneurs and even a surprise visit from an old business partner of mine that I hadn’t seen since we sold our company to Pitney Bowes over ten years ago. From there, we moved on to a VIP reception and dinner for the #CCS2016, the 2nd annual crowdfunding summit scheduled for the next day at MaRS Discovery Centre. After a seriously long day, I gathered all of my belongings and hired Uber #4 to take me to the Victoria. Deepak, my driver, was a funky, young, enthusiastic entrepreneur that eagerly listened to me describe my exciting day and delivered me safely to my hotel.

Early the next morning, I grabbed my phone to catch up on overnight activities and saw a recent text that read …

‘Sandi – it’s DPak, your Uber driver from last night. I found your make-up bag and wallet in my car and I want you to know that I am keeping it safe. Unfortunately, I will not be able to get back to the city until 7PM tonight – but I will meet you wherever you are to return it to you safely’

Seriously! Are you kidding me? Has “local taxi company” ever sent you a text message?

I knew this day was going to be great – although my thoughts turned to how to survive a day without any money. Coffee was top of mind, but I soon realized that I could download money to my Starbucks app to get a cup of coffee – morning fix done. My next issue – how to get to the conference – but hey – I had an app for that, so Uber #5 took me to the conference.

CCS2016

Speaking at the #CCS2016 Summit

The #CCS2016 was a huge success – thanks to Craig Asano and the team at NCFA for all they did to make it happen. One of my favourite speakers, Ted Graham, Innovation Leader at PWC presented an engaging speech called “5 things I learned about disruptive innovation as an UberX driver”. Check out his post here.

After a jam packed day, my partner Don, took a few of us for dinner and Deepak and I exchanged text messages to coordinate a “meet” at the Victoria where a very grateful me, met a very gracious Deepak, with my make-up and my money! As it turns out, Deepak was very interested in the SeedUps platform as he is working on his own start-up and wanted to learn more about how to raise capital to take his product to market. Another budding entrepreneur enjoying the flexibility afforded to Uber drivers.

So what is this all about? I just spent a week in a city that is embracing innovation and isn’t scared to disrupt the status quo to create and foster an environment that supports creative entrepreneurship.  Uber is just one part of that. Every one of my Uber drivers was personable and engaged.  Uber encourages customers to rate their drivers, but a little known fact is that drivers can also rate their customers, so being obnoxious or not being ready when your Uber arrives could result in a lower rating. If you notice that it is taking a long time for your Uber to arrive, look in the mirror!

Calgary was built by risk taking entrepreneurs that had the freedom to develop a market driven economy. Now, our city seems to be happy with the status quo, protecting a transportation industry that is not delivering the service Calgarians want and deserve. Competition is at the heart of that customer service. Come on Calgary, it’s time for action. Uber is just a start.