Whether, when, and where

Posts look better with images, so I try to include them. But usually just end up with random nature photos from my camera roll.

It took me a long time to decide to join Matrix Partners—about half of 2020, all in all. Incredibly, six months was arguably the fast version. The process unfolded during my maternity leave with our daughter Bentley; without the need to squeeze conversations into the cracks in a full load of regular work meetings, progress was less gated on my availability. (Squeezing conversations into Bentley’s unpredictable naptimes was another story, but one with a happy, if chaotic, ending.) VC firms are notorious for taking months—if not years—to evaluate candidates. But I realized there was a bright side to the slow pace: going from operator to investor is a big change, and joining a firm is a big commitment. I wanted to be as sure as possible.

Over the course of my conversations with Matrix, I came to a framework that helped ground me: whether, when, and where. I wanted to share it here while the memories are still fresh, in case it proves helpful to anyone else.

When Matrix first reached out, I was stuck on whether. Was VC for me? Isn’t it a retirement career for after you’ve made it? (My eventual conclusion: no! Venture investing is its own whole job. But it does involve a huge amount of autonomy. So if you find yourself longing for the far-future moment when you’ll finally have the freedom to design your own days, that could be a sign that you’ll value one of VC’s most distinctive qualities. That certainly turned out to be the case for me.) To get clarity on the question of whether, I made sure to use my first interviews with partners at Matrix to ask for their own stories of getting into venture, to see what I related to and what I didn’t. As I got more serious, I decided to start prototyping life as an investor, to make sure I was surfacing any unexpected aspects of the job. For me, that looked like spending a lot more time with the founders of a handful of my angel investments and early startups in my network, to test whether I truly loved the work of being in the trenches with them. (I did.)

A few months in, I realized that the question of whether had dissolved. I knew I wanted to try VC one day. Prototyping the role had persuaded me that if I didn’t try VC eventually, I’d be missing out. As I told Antonio in one of our first conversations, one of my big fears in life is focusing on local optimization at the expense of global optimization. If you want to explore your way to the global peak, you’re going to need to drop in on a few different mountainsides. VC seemed like a new mountainside with plenty of promise: not a sure thing, but one of the most different careers I could imagine that seemed definitely worth a try. So then, the question became when.

When was tricky. I felt like I had a lot of energy left for life as an operator. I was happy on the Quip team at Salesforce; I loved my team, I loved the scope of my work, and I felt proud to work at a company with values I respected. But even if I lifted my gaze and looked out at the horizon, the most obvious next step—one I almost couldn’t resist taking—seemed to be taking a head of product role at a post-product-market-fit startup I admired and focusing on helping them grow. Ideally, I’d even see them through IPO. That was my default plan for a hypothetical next chapter, and one I spent a lot of time exploring. But bit by bit, as the whether of venture dissolved for me, I realized that my default plan included a heavy should. I should “finish” my product career before moving on to something else. I should realize my potential as a product leader through a capstone role.

But careers are never “finished,” and they hardly ever go as planned. My life is not a novel and it will not be wrapped up neatly. There will be loose ends littered everywhere, and many half-baked beginnings along the way; that’s the nature of being human. There was a chance that a head of product role could be right for me, but I needed to look at what happened inside my head when I dropped the expectation of narrative satisfaction. Where did I want to be now? And what did I want to be good at in ten years that I wasn’t today? What I realized was that I wanted to get good at the thing I wanted to do one day: VC.

At last, all I needed to decide was where. Where to begin my career in VC? I liked Matrix a lot from the moment they reached out, but they were the first firm I’d ever talked to about an investing role. Venture openings don’t come along every day, so a scarcity mindset would lead down a road of taking the first opportunity that comes your way, the moment it shows up. And that’s not wrong; if you know you want to be in the industry eventually, getting a foot in the door has a lot of value. But the other thing about venture is that every firm is so idiosyncratic that finding a good fit on the first try is not at all a foregone conclusion. More than that: a scarcity mindset may lead to a quick decision, but never to a wholehearted one.

So I took the advice of a few people I trusted, and decided to run a whole process. I got introductions to a few other firms, and responded warmly to another that had reached out to me. I found that the more I put into the process, the more information and clarity I got out of it. So I doubled down and devoted even more time to the opportunities in front of me. (During one memorable week, I spent hours upon hours scanning through hundreds of rows of Pitchbook results for an exercise one firm had assigned…starting at 3am, since I knew those were the only uninterrupted hours I’d get with a newborn in the house.)

I found things to like at every firm I spoke with, and met lots of people I hope to know for a long time. But in the end, the decision to join Matrix felt clear. A close read of Matrix compared to other firms helped me realize that their strengths and weaknesses are my own: understated, thoughtful, and committed to a fault. I felt sure I’d be able to feel like I belonged. And so far, I have.

Whether, when, and where proved useful for me as a touchstone in my own thought processes—a home base to return to whenever my reflections started to feel scattered. But the framework also came in handy when describing my thought process to Matrix and others: by clarifying that I was sold on the whether and the when, I was able to convey urgency on the where, and focus my conversations with every firm on the open questions that still remained for me in practice, rather than in any projections they’d made by putting themselves in my shoes.

Now, on the other side of the decision, the framework of whether, when, and where means even more to me. Whenever I try to recenter myself on what I’m doing here, I’m able to remember:

Whether: I would regret not trying venture one day.

When: There’s no time like the present.

Where: Belonging is the foundation of a long career.

One thing I took from my exploration was that, in venture, a long career is a happy career. That’s what I’m working toward now.