How to Be a Community Instigator
Last week, tens of thousands of people descended on my home town of Vancouver, Canada for the inaugural Web Summit Vancouver conference. Of course, given that I’m an unapologetic instigator, I couldn’t pass up the opportunity to host an event.
Or three 😃.
There was the Web Summit Investor Dinner, where 50 VCs from around the world engaged in conversations about the future of tech. There was the Web Summit Developer Dim Sum, where founders from both small startups and industry leaders like Netlify and Klue connected over dumplings. And, finally, the Celebration of Vancouver Party, where 250 VIPs, including CEOs, investors, conference speakers and the Mayor of Vancouver discussed Vancouver’s tech scene on the top floor of one of the city’s iconic high rises.
As I floated through the buzz of the city, catching up with friends and connecting with visitors from around the world, one question kept coming up:
“How do you do it?”
To many people, the idea of planning a single event — much less three in one week — is overwhelming. So I’m going to show you how to do it.
Here’s how you can be an instigator for your community.
Start with Why
The most important part of planning an effective event is coming up with the “why”. Specifically:
Why do you (the host) want to do this? What is your goal?
Why will the people you want to bring together choose to attend your event over the many other things they have to do in their lives?
Far too many event organizers know their “why”, but fail to develop a compelling “why” for attendees. Instead, they try to use gimmicks. They think that:
People will come to my dinner because it’s at nice restaurant
People will come to my party because it’s at a fancy club
People will come to my conference because it’s in a beautiful city
These gimmicks work on college students and mid-level managers, but not on high-achievers (which, I’m assuming is your target market). High achievers will occasionally go out to a nice restaurant, a fancy club or an out-of-town conference for work, but only if there’s another reason to do so. (Moreover, if they really want to go to that nice restaurant, fancy club or beautiful city, they’ll generally do so on their own terms with their own friends and family.)
In my experience, high achievers gravitate towards events that deliver on one or more of the following four goals:
1. Meeting Other High Achievers
The most ambitious people I know are drawn to other high-achievers. They want to learn from them, connect with them and be surrounded by them. Creating an event focused on the opportunity to meet other high-achievers can be a big draw. The most impactful events often take it a step further by focusing the audience around a specific theme, such as:
A single industry (e.g. founders of developer tool companies vs. all founders)
A job function (e.g. CTOs vs. anyone who works at a startup)
A stage-of-life / career / company (e.g. CEOs of Series B+ companies, exited founders looking for their next thing, etc.)
Most intimate events (dinners, lunches, cocktails, etc.) have this as the primary “why”.
Secret meeting of the Vancouver dev tool founders club
2. Meeting Customers / Partners
High-achievers are always selling. The opportunity to connect with potential customers or partners can, therefore, be a major draw for ambitious people.
Investor-only events are a great example of this. A big part of being a VC involves building a network of other investors (for co-investment, deal flow and leveling up), so any opportunity to meet a large number of credible investors in one place is an easy sell.
“Our team has more than 200 years of combined experience in VC…”
Connecting startup founders with executives of established companies is another great example, provided that they overlap in their areas of interest (e.g. founders of fintech startups and banking/finance executives).
And, of course, events where both investors and founders are present can appeal to both groups.
3. Leveling Up
Focused opportunities for learning are another great way to anchor community events. Identify a shared challenge in your target audience and build an event around one or more people who can speak to the problem. For example:
Bringing in later-stage founders to speak to a group of up-and-coming founders
Bringing in subject-matter experts to speak to specific challenges (e.g. how to hire your first sales person, how to open an office in the U.S., etc.)
Facilitating off-the-record / Chatham House Rule events, where attendees can openly speak about sensitive topics
“Four California VCs walk into a bar…”
4. Paying it Forward
Finally, many high achievers (myself included) dedicate a percentage of their time to paying-it-forward. Often times, you can attract prominent high-achievers to anchor an event through their desire to give back to their community. Many events that involve mentorship and office hours leverage this as the “why” for their mentors.
In addition to planning three events last week, I spoke at two more where my primary “why” for attending was to pay it forward.
Note that it’s essential that you not abuse the goodwill of attendees looking to pay it forward. It’s one thing to ask a prominent CEO to speak for free at your sponsored community event. It’s another to ask them to speak for free at an event you’re charging $100 per person to attend (and pocketing the profits).
Finally, it’s important to note that if you’re creating an event that will bring together two or more groups of people, each group will need a distinct “why” to draw them in — and they’re likely different.
For example, Vancouver Founders Day — an event I created that brought together more than 800 up-and-coming founders with experienced founders from the community — was anchored around “leveling up” for the up-and-coming founders and paying it forward for the experienced founders.
Clarify Who
Intertwined with “why” is the question of “who”. Specifically, who exactly do you want to attend your event?
It is important to precisely define “who”, as the same “why” can generally be applied to a wide swath of people. Moreover, there is no right or wrong answer to the question of “who”. It is based on your objectives for the event as the host.
Part of the answer to this question is demographic (are you targeting early-stage founders, CTOs of growth-stage companies, anyone who invests in startups, etc.?). But there’s also a question of quality vs. quantity. Do you want to create an intimate event where each-and-every attendee is highly vetted or do you want to put on a “big tent” event that’s open to anyone who wants to attend?
There are pros and cons of each approach. I won’t dig into them, other than to say that it’s essential to be intentional about your target audience. If you aren’t explicit in your definition, you’re likely to end up with a mediocre event that leaves everyone involved — attendees, partners and hosts — underwhelmed and disappointed.
Build Your Base
Once you’ve identified the “why” and “who” for your event, you should build a base of core attendees to anchor the event around. These are the folks that are willing to commit early to your event and who you can then leverage to draw in other attendees.
Like a snowball…but with less screaming
There are three main strategies to build the base for your event:
1. Anchor Around a Minimum Attendance
When using this approach, you should reach out to people in your target audience and gauge their willingness to attend, based on a minimum viable group size. For example:
“I’m planning a dinner for founders of developer tools startups. If I can find a night that works for 10-12 people, are you interested?”
Many people are willing to conditionally commit to an event, provided the expectations are met. Once you’ve got those initial soft commits, you can start to entice others to attend:
“I’m planning a dinner for founders of developer tools startups. I’ve got 4 seats left…are you interested?”
As you get closer to your target number, you can switch gears to logistics and lock in attendees. Just make sure you don’t over-promise and under-deliver. If you tell people that there are going to be 12 high-quality attendees and instead 5 random people show up, you’ll burn your reputation.
2. Anchor Around a Person / People
Many events are anchored around one or more high-profile individuals who serve as a draw to the broader target audience. This could be a recognized speaker for a “leveling up” event or visiting high-achievers for a dinner.
A few years ago, several of my VC friends from California coincidentally needed to schedule visits to Vancouver (to meet with portfolio companies, visit family, etc.). I suggested that they all visit during the same week and then anchored a “leveling up” event around their visit. We brought together 250 founders for an event to help them better understand how California-based VCs make investment decisions.
3. Anchor Around an Activity
The third way to anchor an event is to focus on an activity that appeals to your target audience and is synergistic with the “why”. Many founder-focused events are built around activities.
San Franciso-based Brandon Waselnuk has built up a massive community of Canadian expats (the Maple Syrup Gang) anchored around monthly hikes. Vancouver-based IcePanel holds a monthly “Chill Club” for developers where attendees reverse-demo each others’ products (volunteers try to figure out how someone else’s product works with no documentation or advanced instructions).
One advantage to this type of event is that the activity still delivers value even if attendance is low. Another advantage is that they can provide a healthy alternative to alcohol-centric events, thus appealing to attendees tired of happy hours.
The main disadvantage is that attendance for activity-anchored events is often inconsistent. Without a core group of attendees “pulling in” others, individuals make just-in-time decisions based on how they feel about the activity on that particular day.
Activity-anchored events succeed best when they’re delivered over multiple occasions, as their reputation builds within the community. But consistency is key — it’s very likely that no one will show up the first few times (so don’t get discouraged).
Regardless of your approach, start small and build your attendance from there. Secure your initial commits and leverage them to attract the rest of your attendees.
Here’s how I leveraged the early speakers for Vancouver Founders Day to secure even more speakers (which then provided the anchor for all of the founders who attended):
Figure Out the Finances
Once you’ve got the outline of your event, the next thing you have to do is figure out the finances. I’ll assume for this part that you aren’t trying to generate a profit, so our goal is to make sure we break even (that is, we have enough revenue to cover the full cost of the event, including possible overages).
Depending on how your mind works, you can either start with the revenue and then back into the expenses or vice versa. Either way, it’s likely to be an iterative process as you converge on a plan.
Revenue
Event revenue generally comes from one or more of the following three sources:
Host Sponsorship (you and/or your co-hosts subsidize the event)
Revenue from Attendees (attendees purchase tickets, dinner guests split the bill, etc.)
Partner Sponsorship (other groups subsidize the event)
The first thing you need to do is figure out what combination of the above sources you want to leverage to fund your event.
1. Host Sponsorship
From a logistical standpoint, host sponsorship is the easiest way to finance an event. You organize the event, run the event and pay for the event (or split the bill with your co-hosts). Kind of like when you host a birthday party and invite all of your friends over.
Of course, this requires you to be willing and able to pay for the event.
From a business standpoint, this approach makes the most sense for events where the “why” involves meeting customers/partners or otherwise building your company’s brand. Customer dinners, LP events held by VCs and pretty much any event where the attendees fall into the bucket of “deal flow” fit this category.
2. Revenue from Attendees
At the other end of the spectrum are events where the attendees themselves are expected to pay all or part of the costs.
Ticket sales are common for events that deliver high value to the attendees, such as “leveling up” events with prominent speakers. Splitting the bill is a reasonable approach for events that the host is organizing but doesn’t necessarily derive disproportionate value from (like a dinner amongst peers or a coffee / happy hour meet-up).
Vancouver-based tech journalist William Johnson has for years organized a weekly coffee at various venues around the city
When I first came back to Vancouver, I met a number of later-stage founders who lamented the fact that they didn’t know many peers in the city. These CEOs felt that while there were plenty of startup events in the community, they were all focused on early-stage founders. I heard the same complaint so many times that I organized a “Breakfast of Champions” on the first Friday of each month. The offer was simple: I’ll make the restaurant reservation and each person pays for their own meal.
30 CEOs showed up to the first breakfast.
(Note: many events combine ticket sales / splitting the bill with host and/or partner sponsorship in order to control costs, such as events where the attendees receive a fixed number of drink tickets).
3. Partner Sponsorship
The third way to finance an event is through sponsorship arrangements, under which one or more partners contribute to the event in exchange for some form of benefit. Partner/sponsor benefits can include:
Advertising (the partner’s name and logo get included in marketing materials)
Access (the partner gains access to a group of potential customers / partners that they might not otherwise)
Information (the partner receives contact information about the attendees)
All of these benefits typically fall under a company’s marketing objectives, so what we’re really talking about are branding / marketing / top-of-funnel benefits. Thankfully, there are many vendors and service providers who sell to startups, VCs and other groups involved in tech.
The key thing to understand about sponsorship arrangements is that one of two things must be true for a potential partner to lean in:
They either must get some meaningful brand benefit from being associated with the event; and/or
The target attendees (the “who”) must significantly overlap with their target customers or partners
In other words, for a partner organization to commit to sponsoring your event, you need to have a compelling “why” for them.
Expenses
Event expenses are typically driven by the following three categories:
Venue (some venues charge a fee to use them)
Food & Beverage (aka “F&B” costs)
Staffing & Equipment
(Many events will also incur costs for consumables like name tags, lanyards and swag, but these are usually discretionary and/or relatively minor, so I’ll skip them in the interest of brevity.)
The Venue
The choice of venue can either result in a major expense for the event or no expense at all. Auditoriums, convention centers and specialty venues typically charge a rental fee for the use of their space. Many restaurants will also charge a “buy-out” fee on top of other charges to rent out all or a significant percentage of their venue.
The venue for Vancouver Founders Day was…not free
In contrast, many restaurants, bars and coffee shops bundle all of their charges into a single amount based on your F&B purchases, with a minimum spend amount and a fixed service charge (tip).
For “leveling up” events and basic networking, you can often get sponsors to provide space in their offices at no charge, provided they can attend and receive some marketing benefits. And if you’re just getting started, consider hosting it in your office or even the “party room” at a team member’s apartment building.
Tip: Many venues have lower rental fees and F&B minimums on days when they’re not typically busy (typically Monday - Wednesday). In each city I operate, I have a list of go-to venues (typically independently-owned), where I’ve built relationships with the owners/managers over time and where I can organize cost effective, win-win events for everyone involved.
Food & Beverage
F&B spend is the largest expense for many events, but it’s also the easiest to control (as it’s generally tied to the number of attendees).
While it can be tempting to splurge on F&B for your events — particularly if you’re inviting people you admire or look up to — it’s essential that you control your temptation. The best instigators know how to throw events within their means while delivering on the “why”.
Some strategies for controlling F&B costs include:
Arranging fixed menus at restaurants
Filtering the available drink options (e.g. no top-shelf)
Serving shared appetizers / snacks instead of full meals
Off-loading some or all of the F&B costs to attendees or sponsors is also a common strategy (e.g. have a sponsor bring branded food or drinks, provide a fixed number of drink tickets to attendees or even make attendees responsible for any and all F&B).
Staffing & Equipment
Staffing and equipment for events is one of those categories that sneaks up on you. Hiring a caterer? Watching out for the cost of servers. That fancy convention space? They’ll charge you extra for access to the projectors (and a union A/V person to run it). And don’t get me started on the cost of power and WiFi.
All of these costs can be controlled, but if you’re not prepared for them they can be a shock.
If you’re just getting started running events, keep things simple. Organizing a “leveling up” event in a host or sponsor’s office is an easy way to minimize staffing & equipment costs (at most, they’ll charge you a cleaning fee). One big advantage to hosting events with food and/or drinks at a restaurant or bar is that the servers are included in the F&B costs, whereas you’ll often be charged additional fees if you bring in vendors.
One last note on finances: when planning things out, assume that your math will be wrong by at least 20%. Even after running hundreds of events, I still end up with my estimates being off. It might be a service charge that I forgot to add, an estimate that didn’t include tax, or an extra round of chicken dumplings that one of the tables ordered.
None of these things should be a deal breaker — especially if your attendees walk away with big smiles on their faces — but making sure you know exactly what the plan is should expenses go over is critical.
Bringing It All Together
At this point, your eyes might be glazing over, but I promise you that events done right aren’t nearly as hard as they seem. You just need to focus on these 3 key questions:
What is the core value proposition for the event?
What are you trying to achieve as the host, who is your target audience (or audiences) and what is the compelling “why” for each group involved (including potential sponsors)?
What is the anchor for the event?
What is the initial draw upon which you will build momentum?
One or more prominent attendees,
The overall group of attendees, or
The activity that attendees will perform?
How will you leverage that anchor to pull together the various groups that you want to attract?
What are the logistics for the event?
What are your revenue sources / what is your budget? What type of venue will you hold the event at? What other resources will you need to deliver your event (equipment, F&B, etc.) and what will they cost?
There are plenty of other questions to answer and details to define (what color will the lanyards be? what witty name will you give the signature cocktail? what AI-generated image will you use for the online invitations?), but if you focus on the above questions, you’re well on your way to a successful event.
A Few Examples
Last but not least, I thought it might be helpful to provide a few specific examples of events I’ve hosted within the context of the above framework:
