Hi, I'm Brian Alkerton. I worked at a pretty cool startup called Shopify for a few years. I write here about purpose, politics, culture, and anything else that catches my eye.

One Secret To My Success - Posted November 11, 2015

I'm lucky to have read a couple books this year that have seriously impacted my way of thinking: Nassim Nicholas Taleb's Antifragile is probably the heaviest read I've ever taken on a vacation, but ideas like optionality, iatrogenics, and black swan events have had a big influence on me. Another that I recently finished was Superforecasting by Philip Tetlock and Dan Gardner. One impact that the latter book has immediately had on me is that I talk way more in probabilities.

I'm thinking about working on Parliament Hill now that I've put in the work to get an MP elected. I think it'd be fun, I think it'd be a feather in my cap, and I think I'd be good at handling anything thrown my way. I believe the odds of me getting an offer are fairly high, but I've been really hesitant to say it's a sure thing, because I don't have enough information to know for sure. Maybe there are so many better qualified people applying that bringing me in would actually be a negative. I know that the party's looking to hire about 1,000 people and has received around 12,000 applications. Being able to move to Ottawa immediately, my experience both on the campaign trail and in the private sector, etc., all works in my favour, and probably puts me in the top 10% of candidates, but looking at the openings and the applications, it's clear that only about 8% of applicants are going to end up with jobs. So when people have asked "are you working on the Hill now?" my go-to response has been "I think it's got about an 80% likelihood of happening, but it's not yet certain."

Another thing that's been asked of me a fair bit is how I came to the decision to work with Marco Mendicino in Eglinton-Lawrence. I don't live in the riding. I had strong candidates running on either side of my street (Chrystia Freeland to the north, Adam Vaughn to the south), and both had pretty solid chances of winning. So why would I spend the money on a TTC pass and the time on a commute to volunteer so far from home?

The answer involves the application of a process I used extensively when I was working at Shopify. I call it The Graph.

At the start of the election every single riding had projections and polling aggregations that suggested the likelihood of a given riding going Liberal. If we took the percentage odds of a Liberal win in every riding and turned them into a bar graph, it'd look something like this.

That's one column for each of the 121 ridings in Ontario. If we sort that distribution, we get a graph like this.

This isn't representative of the actual distribution of odds in Ontario at the start of the campaign because I just used a random number generator, but for illustrative purposes, it works. Ranking all the ridings like this lets us split them into three categories.

  1. Sure Things. Ridings that are sufficiently likely to go Liberal that short of a massive scandal or screwup, the Liberal candidate's going to win.
  2. Lost Causes. Ridings that are only going Liberal if we come close to a sweep.
  3. Coin Tosses. Ridings that we will lose if we sit around instead of campaigning, but which we can win if we're out hustling and knocking doors every single day.

You can think of anything over 70% as a Sure Thing, anything under 30% as a Lost Cause, and anything in the middle as a Coin Toss. What I wanted to do on the campaign was find a Coin Toss between the Conservatives and Liberals that was on a Subway line, and the closest viable option was Eglinton-Lawrence. It certainly didn't hurt that Marco's a fantastic guy who's going to be a great MP, but that was my thought process. It's a process I wound up reusing over and over again over the campaign.

Every time I'm at the door giving my spiel, I'm doing my best to read the person I'm talking to. If the first words out of their mouth are "Marco's got my vote!" then they're probably a Sure Thing. If they say "The Liberals are a bunch of pederasts, teaching sex-ed to children, and forcing 6 year olds to have anal sex!" which is an actual thing someone said to me, they're a Lost Cause. In either case, I really just want to get out of the conversation as quickly as possible. Coin Tosses might say something like "Marco's a great guy, but I'm terrified by the idea of Justin being Prime Minister." and they're the most fun, because they're the ones I can really work on persuading by making the case for our platform. When I'm out knocking doors with Marco, one of my objectives was making sure Marco spent as much time as possible speaking to Coin Tosses. This didn't always jibe with the broader goal of getting Marco to speak to as many people as possible, but you do your best to strike a balance based on the time of day, how likely people are to be home, and so on.

This is the exact same approach I took at Shopify in the days when I was onboarding new merchants. A merchant replying to me to say it was their third Shopify account and they knew what they were doing would get a quick "Sounds great, XXX - let me know if you have any questions or need assistance!" while someone saying they wanted to launch a business but had no idea what they would sell or what distinct value they'd bring to the table would get a copy-pasted list of resources on starting a business. Someone who had the value prop down but needed help with implementation... that's the kind of person I wouldn't hesitate to schedule a half-hour call with in order to get them up and running. Of course, we don't have data when a person signs up on the odds of them converting to a paid customer, but one of the skills I developed in my time at Shopify was the ability to make those predictions. I never tracked my success, but I remember feeling like I was pretty good at it by the time I had been there for a year or two. Spending as little time on the Sure Things as I spent on the Lost Causes meant I could speed through tickets, and I set more than a couple productivity records in those days.

This basic model of probability and prioritization is not the only thing that's contributed to the successes I've had in life. It probably isn't even the biggest one. But it is one that's fairly easy to grasp and apply to tons of things in your own life. If you do, you might start noticing you can accomplish a lot more in a lot less time.

Yesterday - Posted October 20, 2015

I'm still processing the reality that after 2 months of going out 7 days a week to canvass my fellow Canadians, rain or shine, they collectively chose to trust my Liberal Party of Canada with a majority government. This wasn't expected to happen. Had you said that to me 2 days ago, I'd have told you any expectation on that front was a one-way ticket to complacency and ultimately disappointment. I believed (still do) that we had the best plan for the country, a stellar lineup of candidates, and incredibly dedicated volunteers... but a majority? Pardon my French, but Holy Fucking Shit.

Like I said, I'm still processing. I'll probably be more elegant in how I talk about this in the future (or not). I can say this much - it's difficult to wrap your head around the complexity and organization that goes into a successful election day until you've been through it yourself. Difficult isn't impossible, though, so I'm writing this post to give you a walkthrough of my election day to try and convey just how much is involved. I was one poll out of over 200, in one riding out of 338. Not every riding has that many, but all in, there were over 80,000 volunteers working as hard as I was for the Liberals alone... like I said, it's a massive undertaking. Here we go.

6:30am: My alarm goes off. I didn't have to head uptown for an hour, but I wanted to have time to treat myself to a nice big breakfast. I take advantage of Siri being always on with the latest iPhones and set a new alarm for 7:25am without moving an inch.

7:25am: Snooze button.

7:34am: Get up, shower, run to the subway and head to Eglinton-Lawrence. There are multiple offices open for the day across the riding because traffic isn't something we can waste time on, most operating out of volunteers' homes. I'm assigned to the main campaign office where I've been volunteering for the past couple months.

8:35am: I'm a few minutes late, but it's no big deal as we shouldn't be out pulling votes until 9. I get my marching orders for the day: 3 rounds of pulling votes on two condo towers, plus scrutineering at one of them. Realizing I've skipped breakfast and that I'm going to be out all day talking to people, I have two bran muffins and a coffee. Please, tell me more about how you "like to live dangerously".

9am-11am: Over the campaign, we've been going out every day identifying people who are inclined to vote for us. For obvious reasons Elections Canada provides no information to who people are voting for until polls close. but they do provide all candidates' teams with the list of everyone who voted in the advance polls. We can cross-reference that with our ID'd support so that we're encouraging the people who haven't yet voted while not hassling those who already have. It may be the case that someone who previously said they'd vote for us will vote for someone else, we have no idea how people vote, but we know if they've voted. I'm given stacks of door-hangers with poll information and told to rush through both buildings, leaving one on every door where a supporter lives. I think I'm done Round 1. I am naive.

11:15am: As I begin the several-hour process of regretting those bran muffins, the coil on my e-cigarette burns out, filling my mouth with some pretty acrid stuff. It's one month to the day after I last smoked, but I really don't have time for this today, so I buy a pack of smokes at a gas station. It's not a proud moment, but I'm relieved to realize that cigarettes taste awful to me now. After today, there's no way I'm not sticking with quitting (sure enough, I haven't even been tempted today).

11:30am: I am not done Round 1. Once the door-knockers are out and the polls are open, we start getting hourly data on who's voted from Elections Canada. This makes it sound more advanced than it is. Now I go back to my main building (the one I'm scrutineering), tuck in my red pocket square, put away my campaign button, and collect the paper lists of who's already voted, eliminating all the people I need to vote but who have already voted. My second building is in a different poll, so I'm getting that data from the campaign office as it's returned to them, meaning my rotation for the rest of the day looks like this: Get Updated Voter List, Building 1, Building 2, Home Office, Get Updated Voter List, Building 1, Building 2, Home Office, Get Updated Voter List, Building 1, Building 2, Observe The Vote Counting, Home Office, Victory (or Concession) Party. None of these places are arduously far apart, but I know I've got an unfair advantage in my weekly Fitbit challenges.

12:00pm: Lunch. Swiss Chalet's roast beef is pretty damn good.

12:30pm-2:30pm: Round 1, for real this time. As I work through the building, I can see other canvassers have been through. It's unnerving to see two door knockers on a single door, because it means that one of us called it wrong, and I have no way of knowing if it was us. There's also some pretty shady anti-Trudeau fliers strewn about some floors. One of the rules of campaign advertising is that whoever's putting it out there has to a) register with Elections Canada and b) say who it's from on the flyer (typically it's "Authorized by the campaign agent for ______" in fine print). These don't have that, and while I sincerely believe the Conservative campaign had nothing to do with it, I can't see a scenario where they'd complain about his talking points getting out there in addition to some good old-fashioned hysteria about Ontario's sex-ed curriculum. Personally, I think it was this guy, and you've gotta respect the hustle, you know? The headline on the flier is "Justin Trudeau and Kathleen Wynne are Just The Same." Remember that, because it'll come up later.

2:00pm: An elderly woman tells me it's illegal to canvass on election day. It isn't. I show her the relevant paperwork from Elections Canada (I always keep a copy handy when I'm out). She doesn't buy it, says she's calling the super. I feel zero shame about farting as I walk away after wishing her a good afternoon. The bran muffins seem to have finished unleashing chaos.

2:15pm: The super's a supporter, so I'm knocking on his door too. He says it's all good (which it is), tells me he had just come back from voting, and that he voted Liberal. Huzzah!

3pm-8pm: Rounds 2 and 3. Lorne the poll clerk and I are now on a first name basis! The elderly woman (who, to clarify, has only encountered me in the hallways of the building) sees me again and says "Still breaking the law, eh?" I show her the paperwork again, tell her to have a nice day again, but don't fart as I walk away. The bran muffins have indeed finished unleashing chaos.

8:30pm: I've got a tiny bit of downtime, so I grab a beer at a sports bar called The West Wing which feels inappropriate but it's the only option within a kilometre of my location. The Jays game is on. The election results are not. I see word on Twitter that Atlantic Canada has gone red, but I don't read too much into it... I was expecting as much and it was still super-early.

9:00pm: Back at the polling location, where Jim, another scrutineer, is trying to get into the lobby as well. The building office we'd normally call is closed, but I offer to wait around and call his cell once I get into the lobby and can give him access. I'm fully aware we disagree on politics, but there's no reason to be a dick about it.

9:30pm-10:30pm: Phones off, time for the count. While the votes are being counted, it starts pouring outside, and as we leave, Jim the Conservative scrutineer offers me a ride back to the Campaign Office. We talk about everything except politics. He's a good dude.

10:35pm: At what I'm realizing will almost certainly be a Victory party. It's looking really good for us, better than anyone predicted.

Later, I lost track of time: Marco's speech. Trudeau's speech, none of which is audible over the cheers in the room. People are ecstatic. All the hugs. All the beer. Not enough food (there was plenty, I just didn't eat enough). At least a couple more cigarettes. After hundreds of hours volunteering, the vindication of winning has filled me with a catharsis unlike anything I've ever experienced.

Later, after the subways have closed: I'm drunk, happy, waiting for the Dufferin Night Bus, enjoying my last cigarette for what I expect to be a very long time, and it dawns on me: Kathleen Wynne won a majority in her first campaign as leader too, didn't she?

You're Going To Vote? That's It? You Can Do Better. - Posted October 06, 2015

All right, so you want to send Stephen Harper packing, or maybe you don't! Either way, there's so much more you can do than simply head to the polls on October 19th (or this weekend if you're down with the whole advance voting thing). And if you're in a position where you can do more, you should. Here's a few simple things you can do RIGHT NOW to make a greater impact on the outcome of the election, whatever outcome you're seeking. Me, I think the Liberal plan for infrastructure investment and a modest push to reduce income inequality is the best approach, but everything I'm describing in this post can be applied to any political party. If there's any glaring examples of bias in what follows, let me know. I've tried to keep it pretty neutral.

1) Target your support. There's a lot of very competitive ridings across the country, and just about every possible matchup you can think of is accounted for. Want to see an NDP candidate take down a Liberal incumbent? Want to see the Greens pick up a second seat? Do you live in a riding where there's no chance of a Conservative winning but you want to contribute to them getting another 4 years in charge? You can do any of these things by looking at the riding matchups and finding a riding near you where the party you most want to help/hurt is in a tight race. If you live in downtown Toronto and you really want to send Harper packing to the point where you don't particularly worry about whether Mulcair or Trudeau is in the driver's seat October, keep an eye on your local race, but frankly there's no chance in hell that the Conservatives pick up a seat in downtown Toronto. ThreeHundredEight has done a great job of aggregating polls to try and project how every riding in the country is going to play out, and if you're looking for a source with a more explicit bent, there's also, who deserve special props for open-sourcing the algorithm they use.

2) Volunteer. There is not one candidate in the country who will not accept your help with open arms and many many thanks. If you can spare a few hours between now and election day, the candidate and their team will have work that needs to be done to help them win. Maybe it's door-to-door or phone canvassing, maybe it's putting in lawn signs, maybe it's just whipping up a dinner for the other volunteers. If you call their office and offer to help, you will have opportunities to do so, guaranteed.

3) Donate. Canada has kind of a ridiculous system of tax credits for political donations, in that you get 75% of all donations up to $400 back at tax time. You get less back for greater amounts, up to a cap of $1500 in total donations. I don't know many people who couldn't throw $50 or $100 on the credit card today when they know they're getting 75% back in a few months. So if it matters to you, and you can afford to do it... do it, and target that help to a riding where it has a real opportunity to make a difference. You can help finance ad buys for your party of choice if you give through their main website, but if you want to contribute on a local level? Contact the candidate's office to ask what's most convenient for them. Hang on to the receipt, claim the expense at tax time, get 75% back (or less if you choose to give over $400).

4) Vote on October 19th. All the donations and volunteer hours don't add up to much if you don't get out and vote for the local candidate you want to see representing you in Ottawa. If you're reading this far and you don't vote, seriously... what the hell are you doing? Governments have the exact same amount of power whether you vote for them or not. Yes, first past the post is kinda crappy as an electoral system, but it's the only one we've got, and any changes to that won't happen until a party is elected that wants to change things (to their credit, both the Liberals and NDP have platform planks on this very issue).

Is your voice small? Yes. Is one vote likely to change things? No, it's not. But a surprisingly small number of votes in aggregate absolutely does change things when there are ridings in every election decided by a fraction of a percentage point. By targeting your support, putting everything you can into it, and voting while encouraging others to do the same, one person can make a difference in this election that far exceeds the impact of just their vote.

I sincerely hope that person is you. 

Why I Quit, And What's Next - Posted September 06, 2015

So, tomorrow's the one-month anniversary of me quitting my job at Shopify. It was as amicable as these things can go.

To answer the one question I've heard more than any other since making my decision, why did I leave an amazing company with great perks? To be clear, Shopify is a great company, easily the best I've worked for. I'd be lying if I said I didn't miss the catered lunches, snacks, and camaraderie. But without diving into exact numbers, here's why:

Not the most elegant graph, but I'll try to explain. Joining Shopify in 2011 was a greater risk than joining (or continuing at) Shopify today, so people joining in those days got significantly more stock options, which in my case wound up being worth more than all the salary and bonuses I earned in my entire time at Shopify combined. Post-IPO and with my 2011 options fully vested, the total return on my time became a function of my salary and the day's stock price. I ran the model a few different ways, and whether my salary doubled, halved, or even disappeared didn't really have a huge impact on the total gains. With that in mind, I had to ask myself: what kind of marginal return on my time and energy am I getting by staying at Shopify, and what am I actually doing this for? What's the endgame? Once I realized my reason for being wasn't to work at Shopify forever (as much as I've enjoyed it) and that I'd be financially okay if I left (as nice as the benefits were), the job started to become a grind, and it became really hard to motivate myself. At that point I knew I needed to either shake things up or leave, and when it became clear the former wasn't likely, leaving was the right call.

So: from years of hard work and a lot of luck, I can feed myself and keep paying the bills without needing to work for a while. Not forever, but a while. And given this time, I should probably work on whatever I was put on this earth to do, that one overarching purpose, that thing I can do that no one else can, that thing which will make the world a slightly better place and which simply won't happen unless I step up and do it. What is that thing?

I don't know. I couldn't name it with any certainty if you put a gun to my head. But I read this James Altucher piece recently and through some synthesis of his thoughts and my own, I've drifted towards the following as a central idea that drives a lot of my day-to-day actions:

It's almost impossible for me to become the best stand-up comic in the world. The odds of me being the best programmer, the best politician, the best salesperson... all extremely long. I sure as hell will never be the world's foremost economist, and I'm okay with that. But I can absolutely point to times where some knowledge of economics has made me far better as a salesperson, where knowing how to tell a joke has helped me disarm people who disagree with me on politics, where understanding programming basics has helped me understand bigger systems, even if I couldn't write them from scratch.

It's a bit frustrating to say this, because I always believed (and I kinda still do) that someone who says they're a Promoter/DJ/Model/Actor/Web Designer/Social Media Guru/DJ/Writer is almost certainly full of shit and unlikely to offer much value to anyone. They're a failed DJ (you can tell, they mentioned it twice) and they're just flailing to find anything they enjoy that someone will pay them to do. Because if it's just a slash, if all these distinct interests fail to inform and build upon one another, then you're just spreading yourself thin and limiting the upside because in any given domain there's going to be people doing what you do, only better. A full-time DJ will kick your ass if you spend 80% of your time not DJing.

So as I go on through life, what am I doing? I'm telling jokes, I'm keeping up on politics, and I'm noodling around with the latest technology, but none of these things are in any way siloed. That's my intersection, and it's one I can aspire to be the best in the world at. My sales background is how I apply that intersection to the world, and my econ background is how I measure the effectiveness of that application.

I'm someone who can crack jokes backed up by hard data, who knows how to win people over to my way of thinking, and who has the applied skills to not only fit that persuasion into larger business or political objectives, but accurately measure its effectiveness. I'm someone you almost certainly want on your team, and I really didn't mean for this to turn into a "Hire me!" post. But here we are. Could I sit on my ass for a while? Sure, but that's nowhere near as much fun. There are things on the horizon I'm thinking about, none of which I'm anywhere near ready to announce, but I'm keeping my options open and trying new things that complement my existing skill-set.

Along those lines, I attended PAX last weekend, and if you haven't seen the latest VR stuff from Valve or Oculus, you're missing out on the future. The controller interaction and visual fidelity are getting to a point where it's starting to cross the uncanny valley. It was always virtual, but the state of the art no longer feels that way. It just feels right. And knowing that makes you think about potential applications and how big this is going to become in 3-5 years once the cost comes down enough for it to go mass market, which is likely inevitable... knowing that will absolutely impact on decisions I make about my career in the future.

I'm also more politically involved than I've ever been, canvassing a couple times a day with one of the local Liberal candidates in the lead up to the next election. As someone who's observed from the sidelines, following it closely through the media for most of my life, I can tell you that getting elected really isn't anything at all like it's often portrayed. It's much more local and personal, and all the national storylines people try to craft to get more play in the media... don't really hold a candle to making meaningful connections with the constituents you want to represent you.

Suffice to say, I'm keeping busy, I'm happy, life is good. 

Tomorrowland - Posted May 24, 2015

"Where the great would not be constrained by the small!" - Andrew Ryan

I'm not the first to draw parallels between Andrew Ryan, villain of the video game Bioshock, and Walt Disney. The resemblance was intentional, but I don't think it's ever been so clear to me as it was after I saw Tomorrowland this weekend. Spoilers ahead.

It seems awesome at first glance. An alternate dimension where the creative and brilliant among us can go and not be restrained by the system, where anything we imagine can be built! Sure, the world we leave behind might go to hell, but Tomorrowland? Tomorrowland is going to continue being amazing!

And it is amazing. There's a long take when one of the characters first sees Tomorrowland that made my jaw hit the floor. It's beautiful, exciting, fun, a place I'd love to visit. Who wouldn't? There's jetpacks and crazy hover-swimming pools! It's never explained, however, why all these amazing advancements couldn't be brought back to the world we know. Is that sloppy storytelling, or a future-world inhabited entirely by people who feel they have no obligation to give back to the society that got them to where they are? A Planet of the Eduardo Saverins, if you will.

One of Tomorrowland's discoveries is a machine that can predict the future, which it turns out is pretty bleak for us on Earth. In their profound benevolence, Tomorrowland broadcasts our horrible future back to us in the hope of scaring us straight, only to find that we take to it and embrace a future that guarantees our destruction, but which at least asks nothing of us. This is where the film starts taking shots at all the dystopian fiction out there at the moment, and I agree with the central idea that we need to focus on hope and finding solutions to our problems, but the solution proposed by Tomorrowland is for all the smart and creative people to bail out and run away to another dimension. Poverty, bureaucracy, and all the other boring challenges of the Unexotic Underclass are to be ignored in favour of hovercars and rocketships. That's not a solution, it's a setup for dystopia on earth, the one thing the movie rails hardest against. I remember joking as I walked out that Tomorrowland was a prequel for Mad Max, because if all the brilliant, creative, and talented people got Raptured (whether religiously or otherwise), they'd be fine but the world would be in trouble. 

To see a movie with such massive ambition and technical mastery on display fail at making an important point because of well-intended but half-baked ideas... well, it's a disappointment. I can usually forgive plot holes, but thematic holes this big can't be overlooked.

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