What 2020 taught me about leadership and venture capital

Two lessons I learned as a woman and mom at the helm of a tech startup

It’s impossible to sum up 2020 in an article, and I’m not even going to try. But as we close out this terrible year, I want to share two (of the many) lessons I learned as a founder leading an early stage company through the hellscape of 2020.

Lesson #1: Empathetic and vulnerable leadership is great…as long as you’re a man with privilege

I consider myself to be an empathetic leader. My decisions are always data-backed, but I prioritize the wellbeing of our people and I’m understanding when folks make mistakes (to be honest, I’m far more forgiving with others than I am with myself, but that’s another story). I believe that we can get through anything if we put honesty, humility, and collaboration at the center of our interactions. All of this sounds great on the screen. It’s the way leaders should be! Right?

11 images from Unsplash. Of the 11, 8 of them are white men. The others are board game pieces, a protest sign, and a lion.
The top search results for “leader” on Unsplash

Recently I noticed a pattern emerging in my professional relationships: once I open up and introduce vulnerability into the relationship, the dynamic changes and suddenly people overstep. And I mean, WAY overstep.

For women in leadership, empathy and vulnerability are often mistaken for naivety. And when people find out I’m a mom — of two! She has a baby! — it gets that much worse. I’ve had people I knew and trusted use my motherhood as a way to discredit my decisions (the worst is when it’s veiled in sympathy: you had a baby this year, I know it must be hard to keep track of everything). This seems to be a pattern for other underrepresented leaders too; their empathy and vulnerability are used against them in situations where privileged men are praised. Just because it’s unconscious doesn’t mean it’s harmless. I’ve seen it with our own people at Crescendo, and if it can happen in a company that was designed to combat this very thing, it can happen anywhere.

Vulnerability is a lens that tints a person’s professional reputation — if they’re a privileged man, he’s doing an amazing job, the picture of modern leadership! If they’re anyone else, they’re suddenly subject to the stereotypes.

In 2021, I’ll keep being vulnerable. I’ll continue to prioritize the people in the business, because a business where people don’t matter is not a successful one in my books. I don’t want to give up empathy, and I won’t. But I’m done with absorbing the punches of people who choose to see it as a weakness rather than a strength.

Lesson #2: Venture Capital wasn’t built for underrepresented founders

I’ve spoken to hundreds of investors over the last few years. Some of them passed on us, I passed on some of them, and one thing has become crystal clear: venture capital was not built for underrepresented founders.

This year in particular, raising in a pandemic with a newborn and a toddler proved to be a fresh kind of hell. In a time when the corporate world was desperate for an authentic and complete way to fulfill their DEI commitments, Crescendo was there to answer the call. In a single quarter we did 6x the revenues of the entire previous year. Investors should have eaten that up, right? It’s textbook PMF, first-mover advantage, hockeystick growth, all the things they tell you you need. But it wasn’t enough.

There was the guy who proudly told me that George Floyd’s murder “didn’t affect” him that much, despite him being “just a couple blocks away” from where it happened. Then there was the one who said I should have lied about my financial models instead of giving them our honest projections, because that would have made our business more investible. And finally, there was the deal that got all the way to the end but then fizzled because they changed their mind about investing in a company with a wife and husband both involved (I’m certain this would not have been an issue had it been my husband in the CEO role instead of me).

All of this, combined with the relentless microaggressions and patronizing feedback, has made me realize that VC was not designed for people like me. VC was designed to reward overconfident bluffers on a get-rich-quick scheme, not people who have a plan to build a stable business.

Photo by Jp Valery on Unsplash

Okay, yes, we knew that already. But the undercurrent that we don’t address enough is that those bluffers are only that confident because society has afforded them the privilege to play with money, and they have the luxury of bluffing big because they don’t know the pain of a real fall. The rest of us don’t have that luxury, so we’re inherently more thoughtful, more careful with our resources. Personally, I’d rather invest in the person who will see every penny of my dollar going out than the one who blows $4000 a month on kombucha. I digress.

After an intensive 6-month period of talking to investors — many of whom watched my infant and toddler grow up via Zoom — I ultimately decided to cut the raise short and focus instead on revenue-driven growth. Let’s be clear: in the time that it took us to get around a hundred no’s, we no longer needed the money.

2021, here we come.

Again, it’s impossible to sum up all of 2020 in a single post. I feel I’d be remiss not to acknowledge that there were far worse things that happened in 2020 than what I experienced here, and also many more learnings that spanned both professional and personal growth. Short of live-streaming my life Big Brother style, I can’t share all of that here, at least not all at once. Just know that no matter how it looks on Instagram, it’s not easy. It’s damn hard.

Here’s to closing the chapter on 2020, and, hopefully, to better days ahead.

The name “Sage” in cursive font


Life as a founder, parent, and child of the internet.

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