Things I Learned about Intuition, Relationships, Note-Taking, and Perfectionism from Working at Antler VC

I get asked often what it’s like working in VC now.

And a lot like tech startups, everything moves fast.

Without taking intentional time to reflect, I know years can go by without me crystallizing some lessons I’ve learned along the way.

Spring Residency 2024 Happy Hour with SVB

Some are new skills I picked up. Some are old lessons I’ve known but are now reinforced.

1. In areas you’re expected to have an opinion, have an opinion

I was tasked to expand our space to an additional floor to prepare for the 100+ founders coming in for Spring Residency.

I met the building landlord and started the conversation about renting the floor beneath us.

This is how it went for a while: We’d meet. Negotiate. I’d get a number. I’d run back to the Partners with that number. I’d ask them what we wanted to do now. BUT THEN they’d asked ME, “what do you recommend we do now?”

I remember being on the other side of that slack realizing I had not actually THOUGHT about the rent myself.

I was just executing. Nose to the grindstone, getting things done because Residency was in less than a month away. I figured all the budget decision making happened with the Partners so why even have an opinion, right?

Wrong.

me just being a messenger for days until our GP asked me for my own recommendation about what to do

I was expected to have an opinion, a recommendation actually, and to defend it.

When I’m given ownership over projects, I perform on them differently.

As a result, I got more aggressive about making sure we got a 2nd floor. I met with our landlord multiple times a week (read lesson #3 below) trying to get to an agreement all while practicing in negotiation role plays with another investor so that I prepare for these landlord conversations.

I’d run back to the Partners recommending new terms and this time with my recommendation all while we were coming down to the wire with Residency starting in 1 week.

Finally got us to a good place that the GP and CFO would sign off on because it felt like my skin was in the game.

2. Remember why you were hired and stay focused on that

My team creates life-changing experiences for founders.

I take that job seriously. The whole point of Founder Residency at Antler is for you to become a better founder.

My Antler U.S. Founder Experience Team ❤️

Running a Residency for 100+ founders is extremely challenging. I do a lot of running around, meeting founders and venture partners, setting things up, creating a feeling of belonging, coordinating with external speakers, and general operations work.

But are we changing founders’ lives?

“Rockefeller’s job wasn’t to drill wells, load trains, or move barrels. It was to think and make good decisions. Rockefeller’s product– his deliverable– wasn’t what he did with his hands or even his words. It was what he figured out inside his head. So that’s where he spent most of his time and energy. He was constantly working in his mind, thinking problems through”

— Morgan Housel

The path to building a great Founder Residency is to sit and think through the full experience as if I was going through it myself and then consider how we can run it even more thoughtfully, effectively, and efficiently.

Antler didn’t hire me and I didn’t join the team to be an office operations manager. It’s an easy slip to get caught up in that work because 1) a place needs to look and feel nice and 2) if not me, then who?

But I must remember that Antler hired me to run the New York Residency and build our community.

So I challenge my perfectionist self to leave the physical space in good enough condition most of the time.

3. Relationships continue to be foundational

This is an old lesson reinforced.

When I was negotiating with our building landlord, I approached it like any other onboarding task– hastily.

I would meet with him, ask what he wanted for it, not get a clear answer, say what we wanted, and then he’d disagree.

These 10 minute conversations sprinkled throughout the day went on for weeks.

We were getting nowhere.

I started to feel pressure as we were running out of time.

In the final week, we were scheduled to reconvene at 4:30 on a Monday. It was my last meeting of the day. He’d come down to our floor and I’d give him the final number.

I opened the conversation with a price.

Ignoring what I said, he started to ask how things were going at Antler since I joined.

We talked about my onboarding, my career, places I lived and worked, and where I grew up.

He talked about his career in banking, how he met his wife, his favorite restaurants in New Jersey, and the past tenants of his building.

What the floor looked like a week before Spring Res.

When we first sat down at 4:30 in the afternoon, the sun was pouring into our south-facing meeting room. By the time we started to wrap up our conversation about our lives, I could barely make out the rim of his glasses on his face as it was me and him, sitting in the dark in a meeting room since we didn’t turn on the lights when we entered.

“So, what do you think?” I remember asking around 7:30pm.

“Yeah, we can do that,” he replied.

I sent him off, ran back to my phone and slacked the Partners immediately.

We got the floor. F yes.

And I realized this whole time, our landlord wanted to get to know me, his tenant, as a person. People care who they do business with. Funny of me to forget that.

4. Being mentally sharp is good, being intuitively sharp is better

I noticed the investors and operators who are best at their craft say things like, “I sense” and “My feeling is” when I hear them explain their decisions in a meeting.

It’s like in addition to the math and models in front of them, they (1) trust themselves and (2) rely on their ability to understand things instinctively.

So many of us suppress this strength that comes naturally in our respective domains.

When it comes to community work, I rely HEAVILY on my intuition and how people feel in conversation. When the vibes are good in a collaboration, the outcome can be exponentially, indescribably great. It’s a relationship after all. On the contrary, when things feel forced, I can sense myself playing a short term game.

When it comes to investing, I’ve got a lot of work and experience to get under my belt before I can rely on my instincts and intuition with reading businesses and founders.

My current rabbit hole is Jessica Livingston, co-founder of Y Combinator, and her Social Radar podcast. She has a keen ability to read and sense founders and co-founder relationships.

My philosophy is that the only way you’re able to have a deep knowing of what’s outside is that you have a complete understanding of what’s inside– your own inner self, dialogue, and awareness.

5. Staying organized is a low lift, high yield habit to maintain

My manager has an insane ability to hold multiple threads of information in her head at one time. For me to hold multiple things, I need to brain dump it all on paper, so I take a lot of notes.

Bringing work to the bar after work to sit and organize my thoughts is A++ with the live jazz ambiance and faded conversation around me, I can actually think and reflect and feel and process and PLAN the best founder residency

I enjoy learning how she thinks about things and in investor meetings, I get to hear her carefully tie together various initiatives happening in our portfolio and our own book of business and how one project will tackle multiple birds with one stone.

I’m training myself to think more multi-threaded as well, hence the relentless note-taking.

Depending on where I’m having the conversation– meeting room, Zoom, running into each other in the kitchen, my notes live in Notion or in a Slack message to myself. At the end of each week, I organize them all in our Antler Hub.

When it comes to to-do’s and action items, I’m a pen to paper girl.

I need to write things down that I’m thinking of doing, especially if it’s a creative experience I want to make happen. It’s gotta be on paper so I can brainstorm it through as the artist I feel I am.

6. The community experience doesn’t need to be perfect but it needs to be done with real intentionality

Residency moments captured by Jaclyn of Starcycle

At Antler, we talk a lot about delivering that “11-star experience” famously coined from AirBNB. I’m still fleshing out my own thoughts about this (future post TBD!)

But if you want to make 100+ founders become a better founder, you need to thoughtfully create a handful of different experiences that will impact each person because you don’t become a better founder in a moment, you become one over time and by making mistakes.

All to say– the Founder Residency doesn’t need to be perfect but it does need to be in a container with community, resources, and structure where a founder can take massive action in a short period of time.

This results in learning and growing which is in of itself life changing for a person.

On the feeling of belonging side, Residency experience needs to be individually curated enough that it touches the hearts and minds of 100+ different people over the course of 8 weeks.

This is tough but not impossible.

My take? I won’t be able to change all 100+ lives. I don’t know. We use an NPS score to measure this internally but it’s debatable if that's even an accurate way to measure.

I think if I change over half of them and we hit our own investment goals, I think it’s a job well done.

“Something I learned from investors and entrepreneurs is that no one makes good decisions all the time. The most impressive people are packed with horrendous ideas that are often acted upon. There are fields where you must be perfect every time. Flying a plane, for example. Then there are fields where you want to be at least pretty great nearly all the time. A restaurant chef for example. Investing, business, and finance are just not like these fields.” - Morgan Housel

If you’re a good community builder, maybe half of the things you do will leave a real mark on people.