“Joe and Maddi are out of the office for the second half of this week. They’re at a conference in Milwaukee, leaving Lauren behind to hold down the fort. I must admit that it’s nice getting to use Joe’s monitor to write this. But he and Maddi are nonetheless missed. While the other interns are off looking at decks, I have no choice but to speculate about what our co-founders are up to. Luckily, I have their schedule at my disposal.
Joe and Maddi fly into Chicago, then drive a rental car to Milwaukee. Joe is driving while Maddi responds to emails on her phone. He tries several times to start up a conversation, but Maddi is locked in. She contemplates putting in her headphones but then feels bad – Joe is clearly very bored.
So, she bites. Joe is saying something about how pickleball is going to revolutionize B2B SaaS sales. At first, she thinks he’s being lighthearted. She asks him, ‘and what do you think foosball will do for real estate?’ Joe doesn’t appreciate her irony and takes her absentminded pushback as opportunity to make his pitch. With her single question, Maddi’s earned herself half an hour of content – enough to last the rest of the car ride.”
That’s what I had written by Wednesday afternoon. On Thursday I was ready to write the whole play-by-play of their experience through my imagination, as someone who has never been to a VC conference before. But then I get the awful news from Lauren that they’re heading back early.
“How could they do this to me?” – is my initial reaction. Sure, it’s unfortunate for them. They had to deal with the expense and energy of going all the way to Milwaukee just to realize they were better off staying in New York. But what about my newsletter piece? It will be harder for me to speculate about them when all I have to do is slide open the office door to see what they’re up to.
Maddi and Joe are back by 11, dressed in athleisurewear and armed with oversized coffee cups (they left for their return flight at 3 am). We have a little group debrief, and they explain that the conference didn’t present the kinds of opportunities they were hoping for. Joe shows an awkward picture he took of Maddi during the journey. Maddi explains the context with a laugh.
In the afternoon, the interns give our sleep-deprived bosses some space as we head to the Financial District to film TikToks. On the subway, as Dawson and Sarah fiddle with the wireless microphones that Joe bought for content creation.
Once we leave the station, I am suddenly deeply uncomfortable. We should’ve anticipated that Wall Street would be flooded with tourists rather than businessmen. It doesn’t bode well for the purpose of our video – the gimmick is that the interns are trying to recruit LPs (because Daring Ventures is currently fundraising). So, Dawson and Sarah hold up signs that say “Seeking LPs,” and we try going up to the few conspicuously white-collared individuals we can spot in the sea of “I ♡ NY” t-shirts. I am mortified from behind the camera.
“Have you heard of Daring Ventures?” they ask a suit who is walking as fast as he can. The man gives a terse response. Dawson keeps talking, but at this point I’m in an awkward jog trying to keep up with them, and I can’t see or hear what’s going on. I’m a terrible cameraman. Dawson gives up on this one, and he and Sarah walk back towards me.
I am deathly afraid of bothering people, a fact I make quite transparent. “Can’t we just plant people we already know?” “Should we ask permission first?” “What if they’re in a hurry to get somewhere?”
Sarah and Dawson think my questions are absurd. They bully me relentlessly until I wallow in silence.
Finally, we can head back to the safety of the office. I don’t think I have a future in filming guerilla interviews. But I’m left with an internal conflict to ponder on the subway ride back.
I’ve always seen the value in having the guts follow your gut. Yet most of the time my gut tells me not to go up to random strangers, or not to send a follow-up when I’m unsure where someone stands. The outreach Maddi and Joe do is not the same as an intern sticking a camera and microphone in someone’s face, but how can you possibly tell the difference when you're in the thick of it?
If Maddi, Joe, and Lauren were similarly paralyzed by the fear of inconveniencing people, their firm would be doomed from the start.
Of course, that fear was not what brought them to the Delta Airline website that fateful Wednesday, searching for an earlier return flight. It turned out that they just didn’t do enough research on what the conference would be like. They made a mistake, and rather than digging in their heels, they decided to admit their shortsightedness and pivot.
The conference schedule I requested from Maddi sits idle in my inbox. Contrary to what my fellow interns might have told me on the streets of the Financial District, I’m not so sure that the lesson from this week is to bulldoze through doubt. I started out with a story in my head that would ultimately revolve around Maddi and Joe’s bravery. Yet I now sit with my own (justified?) apprehensions. If Joe and Maddi had doubted their plans earlier, they would have saved themselves from the hassle of this trip.
I’m gathering the sense that the binary of courage and cowardice is too reductive. There are so many other components to the push and pull of outreach. I guess we’ll all figure it out bit-by-bit.
[Instead of asking a dumb question with a wireless microphone in their face, we’re sliding into their emails and linkedins cold asking them for millions of dollars.] - Joe’s note
