I Don’t Know Who You Are. I’m Sorry.
Last week was Startupfest, Montreal’s annual outdoor celebration of early-stage startups. It’s been one of my favorite events to attend each year since I was first introduced to it while I was at 500 Startups. Founders and investors from across Canada descend on La Belle Province to catch up, swap stories, and check out what the next generation of founders is up to.
I use it as an excuse to make questionable fashion statements
Startupfest also marks the end of a two month gauntlet of tech events that take place across Canada each year. Kicking off in late-spring, the industry’s “festival season” now includes Web Summit, Invest Canada, NACO Summit, Toronto Tech Week, Creative Destruction Lab’s Super Session and more. By the time summer comes around, my default introvert is in full rebellion and desperately in search of a recharge.
But no matter how tired I am by the end of it, I simply can’t get enough of events like these. It’s been almost 10 years since DataHero was acquired (damn…) and I still absolutely love the energy that comes from being around other founders. The excitement. The ambition. The creativity. The velocity. Each and every conversation I have with a founder genuinely invigorates me.
But there’s one aspect of my experience navigating Startupland™ as an investor that fills me with shame. Despite my best efforts, chances are I have absolutely no idea who you are.
As a former founder, this is unquestionably one of the most frustrating aspect of transitioning to being an investor. I remember how impactful each-and-every interaction I had with an investor was to me. That’s why I try to always bring my full, focused self whenever I meet founders.
It’s also what makes this particular aspect of being an investor so frustrating. Even after a decade, I’m still struggling to come to terms with how inverted the dynamic is from the other side.
Maybe it’s just me, but I can still remember almost every conversation that I had with a VC during my days as a founder. Sure, some of the interactions were negative, but the vast majority felt sincere and genuine. Many of these conversations changed my trajectory as a founder — and, thus, the trajectory of my life.
When I first started the next chapter of my career as an investor, I reconnected with many of these same people to get their advice. Inevitably, I brought up some interaction that we had had years before and how impactful it was to me. In almost every case, the VC shifted awkwardly in their seat, looking visibly uncomfortable.
They. Didn’t. Remember.
In some cases, the VC admitted as much. In others, they tried to play it off. At first, it was disconcerting and discouraging. How could so many people not remember moments that were so impactful to me? Was I imagining their sincerity? Was I foolish enough to believe that they cared about me or my future? Was it all a facade?
Now that nearly 10 years have passed, I’ve realized that, no, it’s not a facade (at least, not with most investors). The vast majority of VCs absolutely try to bring their full, focused self to every interaction they have with founders. Unfortunately, most investors do so thousands upon thousands of times each year. Despite the fact that many of these conversations are impactful (or, at least, memorable) to the founders, from the investor’s perspective they are but one of dozens each day.
And the majority of people can’t retain that. Which means that if I’ve only met you once or twice, chances are I don’t remember you.
For founders who are giving everything to their startup, this can feel like a hard pill to swallow. Especially if that initial conversation was particularly impactful to you. But you can reconnect with VCs (or, really, anyone where there is a similar asymmetrical dynamic) in a way that increases your likelihood of a positive outcome: by providing context with grace.
The insight comes from a simple observation: nobody likes to feel uncomfortable in a conversation. And it’s corollary: if you actively remove a discomfort from a conversation, the other person will not only appreciate it, they’ll be more likely to remember it.
The trick? Providing context with grace.
Consider these three examples:
“It’s great to see you again.”
“It’s great to see you again. Do you remember our last conversation?”
“It’s great to see you again. You probably don’t remember, but we met last year at Startupfest during a Braindate session.”
These three slightly different openers leave the other person with vastly different feelings if they don’t remember the prior meeting. The first puts the person on edge (who is this? are they going to ask me something about our last conversation? I don’t want to look dumb…). The second is even more challenging, as it serves as an interpersonal pop quiz (I have no idea who this person is…why are they expecting me to remember?). The third, however, gracefully provides context from the prior interaction with no expectation that the other person remembers.
Using the third approach might spur the person’s memory. But even if it doesn’t, it provides a safe re-introduction. Moreover, it signals that you have a high enough EQ to remove a potential barrier to this new conversation (thus increasing the likelihood that they’ll remember it).
Epilogue
Years ago when I was a graduate student at Stanford, I met a visiting politician at an event. We spoke briefly — 1 or 2 minutes of small talk in which he asked where I was from, what I was studying, etc. Ten years later, I encountered that same politician at another event. Before I could say anything, he commented, “Haven’t we met before? At a Stanford event, right?”
That’s just not fair.