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Confessions of a girlboss
What are you afraid of?
This week I was supposed to write about what’s helped me, on a practical level, navigate becoming an entrepreneur. Entrepreneurship is something that the Diem community has consistently asked us to talk about, and I think it’s helpful to discuss openly since the world of startups and venture capital is somewhat of a black box.
However, I’m going to level with you — I feel incredibly uncomfortable sharing advice on anything to do with starting or running a company publicly, largely because I tend to roll my eyes at the deluge of performative Twitter threads on the matter, and I also sometimes feel pangs of inadequacy that my lived experiences don’t fit squarely into those same threads.
Fortunately (or rather, unfortunately), I was distracted by something else on Twitter as I was battling imposter syndrome and trying to write this newsletter. Sophia Amoruso, a serial founder and author of the bestselling book, #Girlboss, broke her silence on the unfair takedowns of women founders and “girlboss culture.” The straw that broke the camel’s back? A popular tech publication suggesting readers dress up as “their favorite disgraced girlboss” for Halloween, naming Amoruso, Audrey Gelman (founder of The Wing), and actual convicted fraudster Elizabeth Holmes.
Obviously, entrenched misogyny is at play here. And media outlets know that stories that takedown “girl boss culture” resonates with readers because women being “bad” is apparently sensational. We’ve written into this general idea a lot — it’s why women who are criminals are interesting and why it’s hard to evolve online. Gender clouds our judgment.
I’m often asked if I’m scared to get “canceled” as a founder. I put my musings out in public every week, but to be honest no, I’m not afraid of getting canceled, probably because I’ve had a large audience online since I was 19 (the trolls and I know each other well). But I’m sure it would be horrific to go through, having spoken with many founders who have been canceled, and I know that it scares plenty of aspiring entrepreneurs. This is a HUGE problem, which brings me to my main point. Are we really just okay with people not building new companies because they’re scared of being unfairly targeted? As a product of that fear, are we okay with foregoing the economic benefits of more diverse products and services out in the world?
But the main question I’m asking this week is not rhetorical, it’s for existing and aspiring entrepreneurs:
What are you most afraid of?
Is it logistical? Financial? Imposter syndrome? Are you actually scared of getting canceled? Let’s talk about it, and I invite both veteran founders and people who simply have an idea for a business to chime in. I asked my editor, Taylor, to ask me a few example questions to kick things off. For reference, all future questions and answers to this topic will live in this document here. Feel free to ask as many questions as you want, and we will source the Diem network for answers.
Here it goes!
Taylor: Was it intimidating to try and raise money from VCs? That feels super scary to me because of stories I’ve heard.
Emma: I had to learn to love “the game.” There is literally no way to raise money (unless you’re a white tech bro from Stanford) without learning the game of how raising venture funding works. Pitching for funding is potentially the hardest thing I have ever done. I love the actual pitch—that doesn’t bother me—but the emotional strength required to stomach 100+ “nos” over a short period of time, all with the pressure of knowing people’s salaries rely on you succeeding, is simply…horrible. It’s made worse by: investors who ghost you, investors who string you along to ultimately say no, fielding dumb (gendered) questions from those who clearly didn’t spend time prepping for your meeting….the list goes on. Learning the ins and outs, reading anything I could find, asking literally any founder that would talk to me about how it all works, and above all, accepting that this is just what it’s like, has been a game changer. Excel also helped.
Taylor: What do you do when you feel like you’ve bitten off more than you can chew?
Emma: Having a higher purpose that is “bigger” than me has really helped with that. For example, I decided a long time ago that my personal mission is to dedicate my career to pushing gender equality in the right direction. I literally don’t want to spend my time on anything else. Diem is one way I hope to have a meaningful impact, and the wealth we’ll (fingers crossed!) generate from building a successful business will go into various projects that align with that mission. If you go down the path of founding a business, most days are really quite unsexy and stressful, so reminding myself of my personal “why” has helped me.
Taylor: Are you scared of failing? The stakes seem so high when you start your own company.
Emma: I would be lying if I said I’d never had days where I’ve gone to the bad place of “omg what if we lose everyone’s money and have to let the team go” but that hasn’t happened very often, I don’t think about that because it’s a distraction. We also have such strong conviction in the need for Diem from qualitative and quantitative data that it’s (currently) easy to pull myself out of that place and just keep going. Building a company is basically just having the sheer determination, and confidence, to continue pushing it up a mountain even when all the elements turn against you.
Ask your questions about entrepreneurship here. Then, we’ll source our network of founders to get you the answers you’re looking for.
What burning question is keeping you up at night?
Reply to this email with your request and we might just curate the Diem Doc for you!
What We’re Reading (and watching)…
🎥 The new BORN FREE documentary from Paula Goldstein & Rebecca Dayan on the maternal health crisis, watch via iTunes from today!
💊 There’s a morning-after pill to prevent STIs. (Vox)
💋 The sex lives of the one percent (The Atlantic)
👀 How social media distorts body image (Instagram)
From last week’s Diem Doc on WTF happens when you freeze your eggs?
Something I hadn’t really appreciated before freezing my eggs was how drastic the difference in number of eggs is for every woman. This can be a delicate subject for someone who didn’t get as much as they hoped for, or any at all. I adopted the rule of not volunteering my number unless someone deliberately asked.
– 37, NYC
Read more and contribute, here.
Till next time,