So I recently re-shared a 2019 blog post where I’d basically advised founders who’ve raised seed capital to worry less about “how will I raise the next round” and more about “how will I execute my plan?” The post’s kicker said it was “rare for a company that’s executing well to fail to raise a Series A” based on my early experiences in venture.
Some of the responses highlighted that this wasn’t true of companies with founders who didn’t fit the traditional male, usually white, usually straight, founder stereotype. That those founders had personally experienced challenges in what the “executing well” bar meant for them in the eyes of future funders, not to mention that getting funded to start with, and then executing well, was usually already from a disadvantaged position due to the structural issues in tech.
Since I’ve never been a non-white, non-male, non-straight founder of anything, I wanted to learn more about this criticism and how to navigate delivering advice that might not be universal or comes from a privileged vantage point. Kristen Anderson, CEO/co-founder of Catch Benefits, was one of the people in my responses asking me to look at my post through this lens, and she was also generous enough to agree to have a conversation with me about it, that we could share as an update to the original post.
Hunter Walk: Thanks for doing this with me Kristen. So the message of my post, in my mind was, once you’ve raised seed dollars, focus on executing, not worrying about what investors think. That the real power in fundraising comes from a business that’s kicking ass and that I rarely see post-seed businesses that are succeeding fail to raise additional capital. I took your feedback to be “I understand you think this is generally simple and true, but let me tell you, for many of us, it’s not.” Is that a fair starting point?
Kristen Anderson: Yes. I think that there’s nuance, but the thing that stuck with me is the idea that “kicking ass” is some sort of metric that is universally agreed upon. I’ll start by saying my own investors have shared this advice with me, including VCs who are women and people of color who know all too well about systemic bias in their own efforts raising funds. The difficulty, though, is that everything is subjective. So when you — or my investors — say that I need to execute more/better/faster/whatever, what does that actually mean? Has any pre-Series A company succeeded on every metric month after month? Have they definitely de-risked every part of their business? Are their metrics infallible and would every single person in the world agree that they’ve cracked the code? Not a chance. Is there bias in that founders who are willing to say that they’ve crushed it with confidence and leave no margin for doubt are more likely to be white, straight, and male? How about that women are less likely to be believed than men even if they say the same things? Investors will be the first to tell you a Series A is not based on a single metric of growth, revenue, or traction, but that it’s about the whole picture. Well, unfortunately, that ambiguity leaves a lot of room for the milestones to be moved just one inch farther again and again because of implicit, unintentional bias.
Is there bias in that founders who are willing to say that they’ve crushed it with confidence and leave no margin for doubt are more likely to be white, straight, and male? How about that women are less likely to be believed than men even if they say the same things?
HW: All fair points. We’ve backed female founders at 4–5x industry average, so I at least have some visibility into the experiences they have when fundraising, which can be very frustrating for sure. But what trips me up is I’m specifically saying “once you’ve raised seed funding, focus on executing, not pleasing investors.” I’m not saying it’s a meritocracy, I’m not saying you should pretend to be “killing it” because that’s the startup narrative. I’m saying the thing that is most in your control is can you build your business. And to have confidence that if you do that, the probability of other good things will go up. Do you think I should asterisk these types of posts with a “YMMV, if you’re a non-white male founder all these things will be harder?” To some extent that feels like a disclaimer that could apply universally! Does reading that make you think I get it, or at some point are you tired of being spoken to as a “FEMALE CEO” and just want to be thought of as a “CEO” and you can decide what advice is applicable or not?
at some point are you tired of being spoken to as a “FEMALE CEO” and just want to be thought of as a “CEO” and you can decide what advice is applicable or not?
KA: It’s a great question, and where I should interject that I am responding here as a white, straight founder. I recognize my experience is particularly privileged even among underrepresented founders. I’ve also asked myself the question of when I write about my own experience or point of view, when and where do I need to caveat my privilege, or highlight that I live in the United States which gives me immense access that founders all over the world have to work harder for. There’s not an easy answer, especially if you’re trying to be brief and action-oriented in your guidance. The answer is even less simple when you compound your “reach.” I think if you’re in a coffee shop telling 1 or 2 people, the need to caveat is a lot less. If you’re speaking broadly to the public or on Twitter and you’ve got a mere 10k followers like I have, there’s some explanation needed. When you’re a full-blown public figure, the standard is different. As an aside, I’ve had this conversation with my executive coach before: what is the weight of your voice and as an individual how do you recognize when that weight changes? We have different expectations of people in a position of power and influence, and so the pushback may seem unfair because we’d never hold small-scale conversations or personal interactions to the same standard. A question I have for you, then, is how do you think about addressing feedback? When is it important to engage vs. when is bad faith pushback a waste of your time? I think anyone who pays attention to your writing knows that you value equality, diversity, and mutual respect.
HW: It took me a while to understand the ‘public figure’ assumption because despite having some reach, I never think of myself that way compared to the bold faced names in our industry. That said, I’m not naive about the benefits of having reach — or at least influence — so I try to be respectful, responsible and promote other voices. Starting with the assumption that all feedback is valuable, I respond fastest when it’s from people who have been following me for a while and engage directly. Even if I don’t immediately agree or understand, it’s important to assume good faith and be open to learning. Separately, I’ve had pieces of content undergo “context collapse” — when something gets shared to people who don’t know me and, either because it was literally a joke that they take seriously, or because as a white male VC, it’s riskfree to punch up at me, they come back with fire. When it’s specific and informed, I actually respond kindly to those because they don’t know who I am, and I find the interaction a chance to build bridges! I’ll tell you what really gets me though — at a gut emotional level — and I had some of these with this post: when you follow me, and instead of replying, you put me on QT dunk blast. That drives me nuts and makes it really hard for me to assume good faith. I hate QT!
Let me turn the question back on you — when do you engage vs ignore?
KA: I have a guy who follows me on Twitter, and any time I say anything about fundraising being more difficult for women, he comments that VCs are after money and fund whatever gets them the best return, full stop. The implication that hurts is that women would be funded if they could get returns. No matter that statistics show female founders outperform by 63%. I tried early on to engage him with data and conversation, but got nowhere. It caused a huge amount of stress. Now, I don’t respond and I haven’t blocked him, because I derive joy from knowing that his comments are meaningless and not worth my attention. It’s anecdotal, but this reflects my general approach to engagement on Twitter. If someone has said something that I think misses a key point of view, and I believe it comes from simply not knowing or recognizing the gap, I’ll try to engage. If it becomes clear that logic and reason don’t matter, or there is a bad faith effort to drag me into a reply war, I ignore. It’s interesting you mention the QT, because that was actually the reason I responded to your post. That person is someone I follow, and I thought it was massively unfair given the (albeit limited) context I know about you. I think that’s one of those lines that starts to draw out what a “public figure” is. Most people don’t bother to QT anything angry about my posts because no one in the real world knows who I am. Sometimes I think those with less societal power feel the QT is a way to have their voice heard when they otherwise feel ignored. Sometimes, of course, they’re just trying to antagonize and get an audience response. I use the QT if I think the person is too “famous” to respond to a comment, or there’s a broader point about society I think people should see. Recently though, I did get one QT that called me stupid, and wow, I did not realize how hurtful that would be. It was a silly, meaningless incident, sure, but one that has made me reconsider the QT as a tool for criticism.
If someone has said something that I think misses a key point of view, and I believe it comes from simply not knowing or recognizing the gap, I’ll try to engage. If it becomes clear that logic and reason don’t matter, or there is a bad faith effort to drag me into a reply war, I ignore.
HW: I have this term for those sorts of interactions on Twitter: “paper cuts.” None of them cross any lines that violate their Community Standards, but each one of them stings. And if you’re active on Twitter, the paper cuts add up! And the women, activists, etc that I know get 100x the paper cuts I do. I really appreciate this chat. Since we’re talking about how we use our public voices, maybe we can wind it up celebrating some folks who we appreciate online? Here are a few from my own follow list: @Hypatiadotca, @jewelmelanie, @laura, @dansinker
KA: Thanks for the opportunity to talk about some of the shades of gray. Some of my favorite tech/VC voices are: @dunkhippo33, @ArlanWasHere, and @lolitataub. And a few founders you should know of who are doing really cool things: @rachelren1, @ShannonCGoggin (who I know is a portfolio founder for you, Hunter!), and @isadwatson.
Notes and More
🇺🇸 Thank you for voting!
📦 Things I’m Enjoying
These microwave plate covers, SF’s Dandelion Chocolate, and Miley Cyrus’ Midnight Sky live performance.
🏗 Highlighted Homebrew Portfolio Jobs
Sitka is a telehealth specialist network which allows any health provider/system to access a deep set of specialists to augment their own patient care models. They’re hiring remote roles in engineering and product design.