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Middle school Leah raising the roof about a science project, along with my middle school brother and cousin (and our very patient grandfather).

Sounding like you know what you’re talking about is cool. Actually understanding what you’re talking about is cooler.

As early-stage investors, we are tasked with generating opinions about inherently uncertain markets and ideas; this process requires informed (and often outsized) confidence. To develop this confidence, we have to see a lot of companies, in hopes of knowing a little about a lot of things. Going deep on every idea would result in stagnation.

These realities lead many investors to quickly call out what’s wrong with a founder’s idea before listening to what they’re being sold — a skepticism that’s counterproductive, yet often viewed by peer investors as a sign of intelligence, as I explored in a previous piece about what doesn’t make sense in VC. …


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Tryna see the forrest through the trees

People often ask me how I got into VC. It’s a difficult question to answer because the truth isn’t sexy or fun. Getting hired in VC was a winding, frustrating, and often draining process during which I repeatedly convinced myself this wasn’t the path I wanted to take, then reignited interest. I’m happy to share the nitty gritty with anyone who asks. While I was lucky to have a few investors believe in me, more often than not, interview processes left me exhausted and underwhelmed.

When I wasn’t “looking,” the opportunity to join NextView Ventures arrived. Getting an offer was a tremendous privilege; I do not take it lightly, and I know my gain was the loss of other candidates who were likely equally if not more qualified. Now two months into the job, I’ve spent a good deal of time reflecting on what would be helpful to share about my early days in venture. There are many resources available on how to get into venture, and millions of “what I’ve learned in my first 60 days as a VC” posts. Instead of contributing to the noise, I decided to get real and share what I’m still struggling with. …


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I am so excited to share that today I joined NextView Ventures as a Senior Associate on the investing team, based in New York City, the town I’m lucky enough to call home. Thank you to NextView for this awesome announcement!

Why NextView

NextView is a seed-stage, generalist venture capital fund led by brilliant, kind, and curious individuals. Their exceptional reputation is built on their successful investing record, and their unwavering commitment to supporting the founders they invest in—both as leaders and human beings. In an industry often shrouded by platitudes and false promises, NextView is the exception. They are honest, accessible, and real. They are also super fun to be around, whip-smart, and deeply experienced as investors and entrepreneurs. …


Conversation starters that don’t trigger coronavirus anxiety

A couple smiles and waves at the camera on their laptop.
A couple smiles and waves at the camera on their laptop.
Photo: AleksandarGeorgiev/E+/Getty Images

There’s a spontaneity to social life in quarantine. Just a few weeks ago, before the coronavirus forced us all inside, trying to pin down a dinner with friends could sometimes feel like playing Tetris — and everyone involved knew it would be rescheduled at least twice anyway. But now, hunkered down at home, calling a friend on a whim feels normal.

There’s just one hitch: Whenever I get a friend on the line these days, the first question is nearly always, “How are you holding up?” Or, “How is quarantine treating you?” …


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A quote from my late mentor, Lauren Alix Brown

Oh, how times have changed. If the past week has taught me anything, it’s that the lens through which we see the world is never stable, nor objective. In journalism, we call this “framing.”

When brainstorming how to approach a story — be it breaking news, academic research, or cultural commentary—debating the framing has always been my favorite part. In the newsroom I worked at, we spent at least 15 minutes messaging back and forth about framing for every story. Is Facebook’s redesign really a tech story? Or is it a reflection of sociocultural shifts in Gen-Z attention spans? Or perhaps it has nothing to do with Gen-Z at all—who even are Facebook’s power users? …


Focus on small victories

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Anything is possible. Photo: Michelle McMahon/Moment/Getty Images

Brethren, it has been a week. A month. A year. And it’s only March.

In such complicated and anxiety-provoking times, simple wins mean a lot. I’ve got a tip that involves avocados — a prime culprit in the wellness movement.

For a long time, I found avocados very annoying. They barely taste like anything unless you douse them in hot sauce. Certain grocery stores price them like tiny mounds of green orgasms. Toast tastes better with jam, peanut butter, plain butter, or olive oil. Fight me on it.

And yet, I began regularly consuming avocados a few months back, when I caved to peer pressure and tried the keto diet. Like most millennials, I am not immune to #wellness. I’m also always tired and my colleagues told me keto gives you more energy. …


At the troubled luggage startup Away, private messaging and group chats were effectively banned

A woman throws her arm up in frustration as she stares at her laptop.
A woman throws her arm up in frustration as she stares at her laptop.
Photo: FG Trade/E+/Getty Images

One detail still haunts me from that explosive report on workplace dysfunction at the luggage company Away that the Verge published last month: Private messaging, for all intents and purposes, was banned at the luggage startup.

“Employees were not allowed to email each other, and direct messages were supposed to be used rarely (never about work, and only for small requests, like asking if someone wanted to eat lunch),” wrote the Verge reporter Zoe Schiffer. …


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A journal Lauren gifted me in 2018

This week has been shit. This week has also been, in some ways, pure love.

On Tuesday, October 29, Lauren Brown passed away at age 37 (her birthday was two months earlier, in August). Breast cancer killed her, but to me, and so many people, she is still so alive.

Lauren was invincibly fierce. She was hilarious, and obsessed with bunnies. She unlocked the door when I was sitting in the office privacy room sobbing. She listened to my anxieties, then told me I needed to make a decision: grow up and face my fears, or live in perpetual uncertainty. She made me an adult. She Slacked me with crazy story ideas at two in the morning, and held me to them. She had impossibly high standards. …


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(Supermaker)

As a journalist, I spent a lot of time thinking and writing about early-stage venture capital. The mystique was intriguing, and at times, pretty annoying. I loved the idea of deeply researching, sourcing, and betting on the brands and companies that will define the future. But it was nearly impossible to understand how anyone working in VC actually got there.

Many of them were (and are) straight, cis, white men who seemed to have been grandfathered into this highly lucrative, exciting industry by nature of, well, going to Harvard/Stanford and looking the way they do. Or they were in the right place at the right time. Or they “knew someone who knew someone.” …


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chief.com // check it out

I am **extremely** excited to announce that I am joining Chief, based in New York, where I will be leading editorial and brand voice. Chief is a tremendously badass company, led by women I’ve long-admired, Lindsay Kaplan and Carolyn Childers. Their mission is to create the first and most-powerful professional network of women in C-suite and VP-level roles across industries. Chief recently raised $22 million co-led by General Catalyst’s Ken Chenault, the legendary former CEO of AmEx, and Inspired Capital’s Alexa von Tobel (both Ken and Alexa now hold Chief board seats).

Every career decision I’ve made is highly intentional. If I’ve been lucky enough to know you, learn from you, or engage with you as a writer, I believe I owe it to you to explain the logic behind this jump from VC and journalism to an operator role at a 🚀 (yep, that’s a flex).

About

Leah Fessler

Investor at NextView Ventures. Journalist. Thinking about gender, equality, and pugs. Formerly at Chief, Quartz, Slow, Bridgewater Associates, Middlebury.

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