2 Minutes for Instigating
If you’re a hockey fan (and let’s be honest, if you’re reading this post there’s a good chance that you are), then you know what an instigator is. An instigator is the player who started a fight.
Or, at least, that’s what the rule book says:
An instigator is defined as a player who, by their demeanour or physical or verbal actions, is responsible for starting or causing a fight based on any one or more of the following criteria:
i. Throwing or attempting to throw the first punch, thus forcing their opponent to defend themselves by engaging in an otherwise undesired fight.
ii. Verbal invitation, instigation or threat, thus forcing their opponent to defend themselves by engaging in an otherwise undesired fight.
iii. First player to remove gloves and throw a punch without their opponent’s compliance.
Are you looking at me?
But if you’re a real hockey fan (or a fan of any sport), then you understand that being an instigator isn’t just about starting a fight. It’s about altering the momentum of a game. A physical play at the right time — whether a bodycheck in hockey, a sack in football or a block in basketball — can rile up the home crowd and literally change the game.
Ask any hockey fan of a certain age who the man pictured above is and they won’t just tell you his name, they’ll recite it as though part of a crowd of 20,000 fans chanting it in unison. Haaaaaaaaaaaaroooooooooooold.
But instigators aren’t only found in sports. They play a crucial role in changing the momentum of many aspects of our lives.
In our personal lives, almost everyone has that friend. The one who always proposes plans. The one who you can rely on to take the initiative to “start the ball rolling.”
The same is true in startup ecosystems. In his seminal book, Startup Communities, Brad Feld defined instigators thusly:
Instigators are the proactive individuals or organizations that initiate and drive activities, events, or programs to promote engagement, learning, and collaboration within the startup community. They act as catalysts that bring together different stakeholders, fostering a sense of unity and shared purpose in the ecosystem.
Hi. My name is Chris. And I’m an instigator.
The One About Food
Fifteen years ago, my long-time co-conspirator, fellow foodie and occasional co-founder, Gail Yui, and I had an idea: what if we hosted a dinner where the menu was made up entirely of lavish, cholesterol-rich foods (we were about to turn 30 and figured it was all downhill from there 🤣). We regularly hosted dinner parties together and were excited by the idea, but it came with a challenge: how would we pick which of our friends to invite?
We figured that we’d end up with angry friends if we didn’t invite everyone but we also knew that we could only reasonably cook for 8 - 10 people. So we stumbled upon what we thought was an ingenious solution: we would host the dinner on Valentine’s Day. All of our friends were in their late-20s or early-30s (which meant lots of dating and over-the-top courtship), so we figured that only our single friends would show up. A few days later, we sent out the invite for our “Heart-stopping Valentine’s Day Dinner” and patted ourselves on the back.
Then 35 people RSVPd.
Both Gail and I are, at our core, problem-solvers. So after the initial shock wore off, we got to work. We only had about 3 weeks until Valentine’s Day, so we came up with a checklist and started knocking down as many of our obstacles as we could:
Venue: I lived in a condo in SoMa, which allowed us to shift the location from my place to the building’s “party room” downstairs at a minimal cost.
Preparation/Logistics: We revisited our menu and spent time planning how exactly we could prepare in advance to minimize our day-of cook time. Several of our friends offered to help (as prep cooks, waiters, etc.) and we gladly took them up on their offers.
Budget: We swapped out some items in order to reduce the per-person cost (e.g. instead of a few bottles of really expensive wine, we got a couple of cases of solid but cheaper wine).
After weeks of preparation, Valentine’s Day 2010 arrived.
And it was an unmitigated disaster.
We had an (admittedly-ambitious) 10-course menu with a goal of serving one dish every 15 minutes. Instead, we served one every 30-40 minutes. The oven in the party room struggled to maintain temperature and, by 11:00pm, we still hadn’t served the main courses. At the same time, building management was eager to kick us out (the party room was only to be used until 10:30pm).
But as we looked around the room in our shared moment of defeat, we realized that absolutely nobody cared.
In fact, our friends were having an incredible time and were entirely oblivious to our struggles. Because to them, it was never about the food (not really). Sure, they were all curious about what we were going to make, but at the end of the day 35 people RSVPd to our dinner so that they could hang out and share a unique experience with the other 34.
As an instigator, there were three key lessons that I took away from that day:
If the core value proposition of an event is delivered, people will tolerate things going wrong in almost every other area.
If attendees know (and can see) that you’re genuinely trying your best, they will tolerate a lot of things going wrong.
If attendees feel a connection to the organizers and to the community at large, many of them will step in to help.
This is very much the mantra of the “build in public” philosophy. Deliver something of value, try your best and listen to the community.
Over the years, I’ve instigated events both big and small. These three lessons have proved to be critical to the success (or failure) of every single one of them.
The One About Founders
My most recent exercise in instigating, like many, started off with a chance encounter. In this case, it was with a LinkedIn post from Boris Wertz of Version One Ventures:
That post — and my reply — led to a flurry of text messages and phone calls over the next few days. Everyone I spoke to was seeing the same thing, at least in the Vancouver ecosystem:
A desire for connection, manifested in an increasing number of grass-roots communities popping up (developer communities, founder communities, design communities, AI communities, etc.)
Relatively little connectivity amongst those communities
Virtually no connectivity between those communities and the experienced founders and communities of past generations
Which begged the question: how could we harness the expertise and experience of Vancouver's previous generations of tech founders to help accelerate the next generation?
At that point, it was the last week of July. Everyone I spoke with suggested that we plan something for the fall. But I’ve always been a believer that velocity is the one metric that matters most. If we really wanted to inject some energy into the Vancouver ecosystem, we needed to do it before the busy fall season when founders are pulled in 30 different directions.
So I started sending text messages and emails to some of the “OG” founders I know:
To my amazement, every single person I emailed responded almost immediately, with one of two answers:
“Absolutely!”
“I wish I could, but I’m out of town that week.”
Next, I turned my attention to sponsors. Vancouver, like most startup ecosystems, has plenty of corporates that are eager to support community activities. Would they be willing to sponsor an event like this?
Again, almost everyone I spoke with responded instantly, “Absolutely!”
With speakers, mentors and money lined up, all we needed was a venue. I figured that if we got 100 - 150 founders to attend, that would be a rousing success, so I reached out to a handful of venues that I knew could accommodate 150 - 200 people. We quickly landed on one that would be a perfect fit.
On July 31st — 5 days after sending the initial emails to potential speakers — I posted this announcement on LinkedIn:
In less than 4 hours, we reached our capacity. By the end of the day, more than 350 people had registered. By the end of the week, we were at nearly 500.
It was clear that we had hit a nerve with the value proposition. Now, it was time to deliver. Together with the team at Panache, our partners (Fasken, Google, Boast and Web Summit) and others from the community, we got to work.
Destination Vancouver stepped in and helped us to get a new, larger venue for our daytime activities that we would never have otherwise had access to: none other than the Vancouver Convention Centre.
Nice place for a tech meetup, eh?
Fasken helped us to secure a new, larger afternoon venue that could accommodate the founder office hours and cocktail party: GoodCo.
Office hours and pinball machines, who could ask for more?
And each of our partners not only doubled-down on their financial commitment, but they came to the table in countless other ways (everything from lanyards, name tag printing and signage to staff for the registration desk and even my co-host — thanks Casey!). Not only that, but many more people from the community pitched in, from William Johnson helping with mic duties to J. Ryan Williams as the event videographer.
As a result, in only 3 weeks we went from a LinkedIn post to an event hosted at the Vancouver Convention Centre with nearly 800 registered attendees!
And guess what else?
Plenty of things went wrong:
We ran out of lanyards and sleeves to hold all of the name tags, so had to order them from Amazon the day before.
The sleeves we got from Amazon were the wrong size, so we had to cut hundreds of name tags minutes before registration opened to make them fit.
I forgot to email the final agenda to all of the attendees, so nobody had any idea who was on what panel (or what time they were at).
There was no event manager coordinating the speakers, so a couple of speakers completely missed their panels (thankfully, nobody had a schedule so none of the attendees realized 🤣).
The use of multiple venues wasn’t clear on the event registration page, so many people got confused around where to go for office hours.
…and many more!
But despite all of the challenges, we delivered on our core value proposition: bringing Vancouver founders from across generators together in a welcoming, inclusive, collaborative manner.
I want to thank everyone who helped make Vancouver Founders Day a success, starting with Vancouver’s many amazing founders past, present and future.
And stay tuned. I have a feeling we’re just getting started.
From our 10th annual Valentine's Day dinner ("Hold My Beer")
🚀🇨🇦️🔥