office hours with olivia strobl

Me: Welcome, Olivia! I’m really excited to have you here. To start, would love for you to walk me through your career journey.

Olivia: I went to Wellesley College for undergrad. I studied Neuroscience, nothing related to what I’m doing now, but that ultimately led me to venture investing in the AI space doing AI computational neuro work. Graduated into the pandemic and joined an early-stage start-up called Kingscrowd as employee #1. It was definitely a big risk but a fantastic experience. We were building algorithms for retail investing in the venture space, so a lot of my job was talking to startup founders, learning what they were building, and then building algorithms to determine what would make the best investment for early-stage investors.

Me: What made you decide to pursue your MBA, and how did you end up at Yale?

Olivia: I decided to come to Yale because, after working remotely for 5 years, I didn’t have much professional mentorship, and I knew I wanted to go back into traditional venture and focus on supporting women and other underrepresented founders because I saw the way that they were left out of early-stage funding. I knew that was my ultimate professional mission, and I felt I needed an MBA to do that.

Me: As a solo female founder, I appreciate the efforts! What’s your MBA summer internship, and how’s it going so far?

Olivia: I’m at Connecticut Innovations this summer, which is a state-backed fund for Connecticut-based entrepreneurs. I’m specifically working with the Future Fund which backs diverse founders. It’s been awesome. We hit the ground running at NY Tech week, CT Tech Week, Yale Innovation Summit. I’ve met so many cool founders, and it’s cool to see all the support the state gives these companies. I adore both of my bosses, and the whole team is super kind.

Me: Moving into the big topic of the day. Over the past few weeks, I’ve been doing Pride sections of The Tennie Times, trying to describe a bit of the LGBTQ+ experience, history, what Pride is, why it matters. But there’s only so much context I can provide, so would love to hear your perspectives being a part of this community. How has your identity as a member of the LGBTQ+ community shaped your experience in the workplace?

Olivia: First, thank you so much for doing that. It’s rare to see founders paying that much attention. It’s an interesting identity to have in the workplace because for the most part it’s pretty hidden until you’re at a happy hour and somebody asks if you have a partner. I think there’s a lot of ways in which the LGBTQ+ community is marginalized in the workforce, and then there’s a lot of ways where interestingly it works to our advantage, and specifically for women. There have been studies on the gap between queer women and straight women. It’s kind of a double-edged sword.

[Editor’s Note: Margot Canaday, Princeton professor and author of Queer Career, describes this phenomenon where lesbian women are sometimes considered more valuable employees than straight women because they wouldn’t be leaving the workforce to have children – I know, so many problematic things in that sentence. But the cold, pants suit-wearing woman in everybody’s favorite rom-com is actually a caricature of this “career-woman” stereotype.]

Olivia: Coming out is not a one-time thing. I know that’s a narrative that comes up quite a lot. Every time I’m in a new space, I have to do this mental gymnastics: How does this person feel about this? How is it going to change the way they think about me? Will it in any way – consciously or subconsciously – affect the way they think I can perform at work or think of me as a human? I think most queer people are very good at reading rooms and spaces and knowing when they’re safe. I got really good at not using pronouns and jumping around it at my last job. I was not out at my last job for 5 years, and I got very good at hiding it. And that’s something that I knew I didn’t want to do again. It’s not something I actively bring up, but it’s not something I’m going to hide moving forward either.   

Me: Have you ever felt pressure to downplay or hide parts of your identity at work? Or “code-switch” or change how you present yourself?

Olivia: Yeah, it’s definitely scary. When I was younger and still figuring out my identity in dating, I would have that kind of anxiety and panic, especially in corporate settings like happy hours, where I knew people would be asking about my personal life. I think I got away with it for 5 years because we were remote – I don’t think that would happen in an in-person setting. I definitely do a lot of code-switching, and it’s something I’m trying to train myself out of. I’ve thought about this a lot: how much of myself I want to bring to work and whether I owe it to the people that come after me and the rest of this community to normalize that more. It’s something I think about every day and deal with every day.

Me: Are there moments when you’ve felt especially supported - or unsupported - in your career because of your identity?

Olivia: I have felt incredibly supported in my identity whenever people don’t make assumptions. I’ll shout out my current boss right now. He asked if I had a partner; not a boyfriend, a partner. That’s such a small thing, but it goes a really long way. It made me feel a lot more comfortable around him. It’s also not something I’m actively trying to hide – you could figure it out by looking at my LinkedIn, but you’d be surprised how many people it goes straight over their head. Also, anytime people put LGBTQ+ issues at the forefront of what we’re working on or recognize Pride month, that helps me feel supported.  

Me: Because I did stalk your LinkedIn, I saw that you do a lot of volunteer work centered around advancing the LGBTQ+ community. Can you talk about those – what you did, the impact of these programs, and what you took away from these experiences?

Olivia: I love working with 2 groups in particular: early-stage founders and young people. I worked with StartOut for a very long time and still keep in contact with them. They are a non-profit that works to get more early-stage funding to queer entrepreneurs. I have been a mentor with them, working with founders there to refine their pitch decks and find opportunities to go seek that funding. OutinTech is the other one that I volunteer with. OutinTech matches a mentor with an undergrad mentee. You work with them on a tech project throughout the course of a couple weeks and serve as a confidante for them in their personal life. A lot of them unfortunately don’t have a lot of family support or role models in their life that are part of the queer community. That was really meaningful to me because I developed this strong 1:1 relationship with a college junior who then went on to do really cool things. I still keep in touch with him, he’s doing really well.  

Me: Do you think companies are doing enough to create inclusive spaces? What do you wish they would do better?

Olivia: That’s a good question especially right now. I’m going to New York for Pride and it’s been really upsetting to see the number of companies who have pulled out of supporting New York Pride this year because of the current administration. It’s been deeply upsetting to know that the support was conditional. That’s one thing; if you are going to support this community, it needs to not have string attached. I also think understanding intersectionality – queer people have a lot of different identities, and understanding how those intersect is important. And if you’re going to support the queer community, you’re supporting the whole queer community, and that includes trans people, the asexual community, the intersex community. Education goes a long way, especially in corporate settings. And again, not making assumptions, trying to create inclusive spaces whether that means using pronouns, not questioning people when they use the bathroom that aligns with the gender that they identify as, stuff like that.

Me: Switching to the workwear, the Tennie of it all, you took the Tennie workwear quiz. You mentioned struggling to find a balance between femininity and masculinity in your clothing. Can you talk about what that experience has been like for you, and how you’ve developed your professional wardrobe?

Olivia: After years of remote work, building a wardrobe again was tough. I don’t feel super comfortable at either end of the gender spectrum - I’m not into frilly dresses, but I’m not in suits either. I would say I dress a little bit androgenous, so I don’t always do well with the women’s workwear section, but then I also don’t love menswear. I like to be comfortable. Venture is casual, but there’s a range.

[Editor’s Note: I swear I didn’t even tell her to say this next bit 😊 but if you’re inspired, you can take the workwear quiz here]

Olivia: The quiz was super helpful. It was funny, one of the outfits I got [in my personalized recommendation] was like almost perfectly stuff that I already own and wear, and I just hadn’t styled it that way, so I was like, “oh, this is super helpful”.

Me: You mentioned liking certain brands. Can you give us a few examples of those in case anybody reading is having a similar struggle?

Olivia: I love Uniqlo. I wear their pants to work like every single day. I like American Eagle a lot. Love Old Navy. But yeah, Uniqlo definitely.

Me: What advice would you give to someone who is also figuring out how to show up authentically in their professional wardrobe, especially if they don’t feel represented in traditional workwear norms?

Olivia: I have found a lot of gender affirmation in layering and accessorizing. If I don’t always feel comfortable with the clothing, I feel like I can find a way to adjust with small things. For example, if I’m dressing more feminine, I’ll throw a watch on, and I think that balances the look a little bit. Or if I’m in a more masculine outfit, I’ll wear a charm necklace. It gives a fun contrast. I think you can do a lot with shoes, too. Having a more feminine outfit with oxfords or something like that is definitely a go-to for me.

Me: What advice would you give to younger LGBTQ+ women entering the professional world?

Olivia: Be yourself, but also allow yourself to have boundaries. If something doesn’t feel safe to you, or if it would give you more peace of mind to separate your work and your personal life, that is totally okay. I think I probably needed to hear that. You don’t owe anyone anything, so you don’t have to share any aspect of your personal life that you’re not comfortable with. If you want to come to work as your authentic self, then own it and if people aren’t okay with that, then they aren’t your people.