‘These are the things nobody ever talks about’

Hana Mohan is an entrepreneur and the founder of MagicBell, a plug-and-play notifications inbox geared toward developers building their own products. Most recently, she was the first openly transgender woman to go through Y Combinator. In 2016, while working on her previous business, SupportBee, she transitioned. Hana has written extensively about entrepreneurship and being a transgender woman, covering topics like gender dysphoria, cis-passing, surgeries as a transgender person, and HRT (hormone replacement therapy).

We spoke on the phone in a series of interviews about her experiences going through YC, transitioning while running a company, where she finds support systems as a founder and the challenges of practicing inclusivity as a leader.

I’d love to start with the opportunity you saw for MagicBell. What does the company do? 

We want to help every product team develop a relevant notification experience to their customers. For example, if you use a multi-platform app like Slack or Whatsapp, the notifications just work. In Whatsapp, if you get a notification on your phone and then check it on your desktop first, it removes it from your phone. The best companies today are already building notification experiences that are very finely tuned. We want to make those experiences available to every app developer without having to build the infrastructure of all the edge cases themselves. 

It’s also a growing market. We’re relying on notifications more and more with remote work and with more people using cloud apps, it’s growing a lot. More and more, I think having a notification system versus not having one is going to become a competitive differentiator between apps. 

Would you say there’s a MagicBell origin story?

I’ve been a developer all my life. My previous startup, SupportBee, was a customer support SaaS company; before that, I built a music sharing site that was like Flickr but for musicians. You always have to build notifications for each product, so the idea for MagicBell was just one of those things that I kept thinking should exist. For about five years I kept thinking, somebody’s going to make it. I worked on the customer support company for over 10 years, and it grew slowly to half a million a year in revenue. That’s the company I was working on when I did my transition. 

During that time, I felt so disconnected from the world, and when I came back, I truly felt so lost. I decided to start MagicBell in part because I wanted to personally invest myself in something at that time. 

One of the things about being trans is that it can be really isolating. But for me, working on a business is a very positive, motivating way to stay healthy, fit, focused, and empowered while experiencing that isolation. It’s also a way to connect with others. I didn’t really want to keep working on my previous business because it was going slowly, so I started this. 

You recently went through the latest YC batch. How was that experience? 

While my main reason to work on this business was to personally invest myself in something new, it was also pretty clear that it is expensive to build companies and scale them up. I was certain I wanted to raise money and YC seemed like a good first stop. I learned a lot from the experience, and I don’t think being trans played a big part in YC. The only thing that I found surprising—and when I say this I mean that it was surprising to me—is that discussions between other women founders in YC tended to revolve around starting a family and when to have children. I want to be there and support women through their journeys, but discussions on how to balance raising children with startup life made me feel out of place. If anything, it gave me a sense of how niche this community is—the community of trans women founders—if it exists at all. 

Have you found other folks in that community yet? 

More no than yes. There are very few. In the research that I did before YC, I was trying to find role models and get a sense of the challenges ahead of me. I think at some point, I made a conscious decision to be visibly trans and I wanted to know if there were more trans women founders out there. I definitely found a few, but none that started a company since transitioning and went on to raise money. When we announce our seed round soon, it will probably be one of the very first examples of that, if not the first.

Have you been able to find support systems as a founder? 

Yes. In general, YC is a pretty good support system whether you are a man or a woman. It doesn’t matter. Let’s say you pitch to a lot of investors—you raise money from some and some you don’t. As a woman, I think you have certain prejudices against you. And now, being a trans woman, maybe there’s a little bit more prejudice, but you really can’t objectively guess. I will find out, right? 

The whole world belongs to men, so men don’t really seek a safe space. But we all seek a certain belonging that’s unique and specific to us, and I think that’s hard to find for me in the larger tech community. I will say that people who have been in touch with trans people tend to be less transphobic—there's plenty of research on that. If anything, that’s pretty inspiring to me to continue forward and say, okay, so every person who meets me is one more person that’s going to be at least somewhat less transphobic. 

I also attribute progress to the trans women and the cis women before me. In some ways, the discrimination that I’m facing as a trans woman was the norm for cis women. In 100 years from now, people will go back and see how trans women were treated, but I really will live a much better life than I would have 20 or 30 years back because a lot of people fought for my rights and pushed the envelope. So in that spirit, I’m grateful. It is very isolating, but being a startup founder is as well.

Absolutely, that’s been my experience too in founding a company. Given the presence of the prejudices we know exist in venture capital, how was the process for you raising money? 

That was an interesting experience. Of course, funding for women is terrible [laughs], but then there’s this network of really awesome women. It’s almost an underground thing. Once you get hooked up with one smart, plugged-in woman, she’ll basically connect you to this network of other really smart, great women. 

So for MagicBell, we had a successful Product Hunt launch and because of that, a woman from a European fund contacted me and put me in touch with another woman partner in her fund who is quite well-known in Europe. That woman invested some pre-seed money personally and then she put me in touch with Claire Diaz-Ortiz, who has been phenomenal at putting me in touch with other women like yourself and other investors. 

This is something that I think isn't talked about that much. There’s a lot of data out there on how little funding women get and it’s depressing. However, we don’t talk about how there are more women that are specifically focused on investing in other women and minorities every day. I see it now more than ever as a founder, and that feels very encouraging against the big picture funding stats. It has been really awesome to see that there are these women that are building this network of other strong women who trust each other’s recommendations.

But then I think sometimes you also see your own biases with investing. I angel invest a little bit, and you have to make a conscious effort, even as a woman, to investigate your investment patterns because it’s easy to just invest in a lot of men. In YC, for example, you end up talking to more men because there are so many more men. I made five investments and had I not made a conscious effort to pick women to invest in, it would have been unbalanced. 

Because it’s a numbers game? 

Yes, it’s that, but there is a certain bravado that men put out. Even in the investor updates that I read, the language men use is different. Men are always going to “crush the competition.”

I’m not saying it’s a scientific study, but I don’t think a lot of women go out there and say, “I’m going to crush this competition.” You do expect men to say stuff like that. 

While I was pitching during YC, I got the feedback that I wasn’t enthusiastic enough and I found that investors were attuned to certain words. Some of our competitors kept saying the phrase, “we have a sales motion,” and then I realized that a lot of the traditional investors like that phrase specifically. They are attuned to these words and if you’re not an insider, you don’t use them.

The concept of insider speak is really interesting. On the other side of things, do you think the domino effect of getting connected to women who then connect you to more women creates a parallel insider network to the one that has existed for a long time for men? 

Yes. Had it not been for a lot of awesome women I don’t think it would have been possible for us to raise as much as we did. I think my cap table is half or more than half women.

The other thing about raising money, since my previous businesses were bootstrapped, is that being funded, at least for now, is a less lonely experience. When I was on my own and bootstrapping, sure I could reach out to people on Twitter and my friends, but now I have about 30 people who are invested in the company in some capacity. They’re just a phone call away and they’re always happy to help. Personally, I find that very beneficial for now. 

What do you think of transgender representation in tech in general? 

There’s almost this joke in the trans community, especially on Reddit, that most trans women are in tech. So I don’t know if tech has a lot of trans women, but a lot of trans women do end up working in tech. 

Because it seems more welcoming than other industries? 

Superficially, yes, but I don’t feel that it’s bad for me at all in my day-to-day. One of the developers of React, Sophie Alpert, is trans and she doesn’t try to hide it. That’s why I don’t try to hide it. Sometimes I feel bad that I write “I’m a proud transgender woman” everywhere online. For example, in an AMA I did on Indie Hackers, some people commented that being trans has nothing to do with my achievements. What those people don’t understand is that the world isn’t as meritocratic as they think it is. I write “proud transgender woman” everywhere because there are so few of us out there. 

I want to go back in time a little bit.  You shared that you transitioned while working on a previous startup. What was that like — transitioning while trying to run a business? 

It was my second business, which I started in 2011. It was in 2016 that I realized that I’m trans and started transitioning. Before that, I didn’t really have that clarity. I felt attracted to the whole feminine expression and all of that, but I didn’t realize that I’m trans. So I did continue to run my business in theory, but I was pretty disconnected from it. I wasn’t able to give it what I had as a leader or as an entrepreneur. It was pretty disorienting. My team was very supportive—they stepped up and kept the business running. 

It takes a while to get your bearing back again, at least for me it was like that. Of course, I had some women friends, but most of my friends were men. I lost a few of them who just didn’t know how to process it and didn’t want to talk about it. But even for the ones that stuck around, it was hard for them to understand it and each of them had their own interpretation of it. Some thought that I was on a sabbatical and taking it easy [laughs]. And some are still confused about the gender and sexuality part of it. They supported me as much as they could, but it was still pretty isolating. I really took a backseat from trying to grow the business. I just couldn’t do it. 

That must have been so hard, even though you were making space for your transition. 

It’s why I sort of receded from professional life—it’s almost like peeling the layers off an onion. To even come to the realization that I’m trans and recognize that a lot of my anxiety came from it, I had to first drop the external part of me that was very ambitious. I just had to pull back from work.

I very consciously didn’t do a lot of meetings and I didn’t talk to a lot of people. My life for a couple of years pretty much became about transitioning. But once I came back from my transition and into a more active professional life, I don’t think I had to do much explaining because no one really cares about it [laughs]. 

One of the things that I haven’t seen many people talk about is that when you unpeel the layer of gender presentation, everything is fairly new. You want to cis-pass to some extent to make your life easy, so there’s also a lot of pressure on you. When I was transitioning, I had to constantly make that choice: to blend in or not. When I look at pictures of women who are early in their transition now, I honestly feel they look great. I mean, I looked great too. Trans women are beautiful in all forms. But while I was transitioning, I was always very worried about my voice. I’ve spent a lot of money and time on it. As a trans woman, there’s this additional layer—blending in as a woman. I think some trans women have some sort of internalized transphobia because you’re so often denying that existence for so long. These are the things that nobody ever talks about. 

Do you still acutely feel that pressure to blend in? 

I think we all have our Achilles heel, as a woman or as a man. For me, apart from looks, which is a universal thing women have to think about all the time, the voice stuff has been particularly difficult. As I mentioned, I had to work very hard on it. It’s one of the only things that doesn’t change with hormones. Once you hit puberty, your larynx is just a certain form and you have to do a lot of vocal training to get your voice up and change all of your expressions. That’s the part that was very hard for me and it is for many women. And I think it’s still hard to tread this line of being my authentic self and talking about the reality of being trans versus not coming across as being utterly negative and bitter. I’m sure cis-women feel that too. 

Definitely. [We laugh]

The funniest thing about being trans is that you’re dealing with all these challenges and then at some point you realize, okay, now I think I’m just facing the friction of being a woman. When I realized I’m a trans woman, I didn’t really understand what being a woman is all about, and it takes a long time to figure that out. What does it mean to be a woman? What are the things you will worry about? What are the social frictions? For me, it took a while to understand that looks matter a lot. I was like, just give me hormones and take my anxiety away and I’m happy. Once you are a woman, you will succumb to the pressures of wanting to look good. It is such a brutal reality. It’s not at all an optional anxiety. It’s like you’re trying to have this sort of life without friction, but then your friction changes from being caused by being trans to just being a woman. 

I’m wondering if you have any advice for the tech industry on how it can better support trans folks. What is the industry missing from a support standpoint? 

I do think that the tech industry should offer a leave of absence that’s paid for by companies for employees who are transitioning. This would give people the time and space they need to transition and assimilate back into public life. You need to feel comfortable in your new skin and presentation. Transitioning is a long process but if you need to go for a surgery, you should be able to get that kind of support. Gender confirmation surgery is not an optional surgery—it’s pretty much a medically prescribed one, in all ways. I will make sure my company does that. 

In light of the Basecamp drama recently, you tweeted out a message to prospective hires who want to find a diverse and inclusive workplace. As a founder, how do you think about intentionally building a company with these values? 

One thing that’s surprising is that even though I am very intentional about it, it’s still very hard to recruit women. I thought I could just post a job on sites geared towards women and there would be a flood of applications. That’s not the case and it’s actually been quite challenging. 

I will say that being openly trans has helped attract at least a few trans and queer candidates. They like the fact that this company is led by someone who is transgender and queer. It’s more relatable for them. 

I’ve thought a lot about what it means to be a trans founder lately. During our fundraising, one investor reached out through a friend and misgendered me in his email. I pointed it out to him. Then, without naming him, I wrote on LinkedIn about how it’s not okay that an investor misgendered me while trying to invest in my company and then didn’t acknowledge his mistake when I corrected him. The experience made me think about how, as a leader of a company, you want to skip over that personal misgendering, but it matters a lot to you personally. In these situations, there’s nobody I can really ask for guidance. 

So I think about—if this was happening to someone on my team, how would I respond? Let’s say my CFO is trans and an investor misgenders my CFO. I wouldn’t work with that investor—it shows that they’re not open, don’t take this stuff seriously, and lack a fundamental respect for other people. 

This interview has been edited for length and clarity.

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