What If Women Invented Venture Capital?

On April 25th, 2019, I found myself in an extraordinary situation. And I mean that quite literally. I was hundreds of feet in the air, sailing over the California landscape in a hot air balloon at a truly ridiculously early hour in the morning. I don’t know if you have ever been in a hot air balloon, but I am here to tell you that it is an incredible experience. And it was about to get even more memorable. I was about to get an elevator pitch, or in this case, a hot air balloon pitch, for a new technology company called Translator, Inc. I had met the Founder and CEO, Natalie Egan, the day before, and we had had an instant connection. We had both been invited to a remarkable, 5-diamond, all expenses paid gathering of women+ founders and investors, curated by the team at Bumble Fund, and hosted by Whitney Wolfe Herd and Serena Williams. According to Whitney, the weekend was designed to reimagine the world of venture capital “as if women had invented it”. A meet-up where great things could happen–– and indeed they did. One of the activities on offer was this balloon ride, and it felt like it was ‘meant to be’ when Natalie and I both jumped into the limo at 6am to head to the launch site in Napa Valley.

By the time we had climbed to a few hundred feet up in the air with two other potential investors, I had already heard a little about Natalie and Translator. And for context, she was one of only a handful of founders invited to attend this gathering. The selection process, according to Natalie, was both generous and rigorous, with a focus on women of color and women+ from more traditionally marginalized and underrepresented groups who were all solving for big, real-world problems. So it was not surprising that Natalie had been selected as a transgender woman focused on solving for an urgent need: Diversity, Equity & Inclusion (DEI) and workplace culture. The vision for her company was in part inspired by her journey from presenting to the world as a cisgender ‘tech bro’ founder, to navigating the start-up world as a woman facing both misogyny and transphobia on a regular basis. I recently caught up with Natalie to talk about Translator, and also more generally about women+ navigating the world of venture capital fundraising, the investor/founder relationship, and the power of sisterhood.?

Jacki Zehner: Natalie, I know how I ended up in that hot air balloon, but can you share how you ended up there?

Natalie Egan: It all started in 2018 when I was speaking on a panel for Salesforce at an event called Dreamforce. I happened to be sitting next to Sarah Jones Simmer, who at the time was the COO of the dating site Bumble. We started talking, and she asked me if I used Bumble. I decided to be honest and said no, because at the time, I didn’t think that Bumble was particularly good for trans women as a dating site. Sarah was genuinely interested in hearing my thoughts, and as a fun side note, I ended up doing some consulting work for Bumble, helping to make the platform more inclusive, which was super cool!

At Dreamforce, Sarah also told me about the Bumble Fund and encouraged me to apply, which I did. However, I didn’t think anything would come of it because I had been let down so many times in the past by funds that say they want diverse deal flow and diverse representation of founders, but for some reason they would never write a check. But this time I did get funded, which was amazing, and I was also invited to the Bumble Fund Summit, which ended up being one of the coolest and most validating experiences of my life. I had been to countless events like this prior to my transition, and they were mostly incredibly toxic tech bro spaces. White men pitching white men while they pound their chests (and later pound beers). The Bumble Fund Summit was a complete reinvention of this, and it was a glimpse into what it would be like if venture capital was actually run by women. I found out pretty quickly that the answer was that it would be like nothing I’d ever experienced before. There were no “gotcha” moments, and no one was trying to take advantage of anyone else. Quite the opposite, as everyone was genuinely interested in helping each other. The entire summit was highly curated, and it was designed to allow us all to get to know one another better so that we could launch our businesses and make the world a better place, in addition to getting good returns. I met so many powerful women at that event, and you were one of the first.

JZ: We met on the first day at the pool and very quickly fell into an intense conversation.

NE: Yes! We had a deep connection that first day by that beautiful pool. I told you that I have a dream to change the world through technology; to use it to spread empathy and understanding.

JZ: And I remember feeling like I was already committed, but I did not let you know that. We had a few more days to figure things out.??

NE: The next day was the morning of the hot air balloon ride. I had signed up for the activity to push myself outside of my comfort zone and conquer a fear by trying a new experience. But I was still scared, and even more so when I showed up and it was just me, you, Arielle Zuckerberg, and Nathalie Molina Ni?o going for the ride.

JZ: So basically you and three potential investors.

NE: Exactly. But not just regular investors. Badass women-changing-the-world type investors. And I was the only founder. On the inside I was freaking out. Where were the other founders so I could hide?? And talk about imposter syndrome! I was so nervous. Will they accept me as a woman?? Or will they just pretend to accept me because they have to? I was just trying to stay cool on the outside, and then at about cruising altitude, Arielle turns to me and says, “Okay Natalie, give us your hot air balloon pitch!”

I was completely taken off guard and unprepared. There was no countdown clock. No pitch deck. No intimidating men staring blankly at me who see risk no matter what I say or what I have accomplished. I thought gosh, how should I do this? And then I had my moment, I just decided to tell my story. I started at the beginning. I told you all about my childhood, growing up with two older brothers and a very conservative and successful father, who all instilled masculine principles of discipline and character in me any chance they could. I talked about the shame of hiding who I was my whole life, the damage it caused, and the people I inadvertently hurt along the way. And then of course I spoke to the challenges I’ve faced as a transgender woman in the startup world, and my post-transition discovery that the white male if-you-work-hard-you-will-get-what-you-want type of tenacity that I was taught growing up doesn’t automatically equal outcomes if you come from a marginalized background. And finally, I laid out my vision for Translator to address all these problems. Both where we were and where we were headed.

When I finished, you immediately said, “I want to be a part of this!”, but to be honest, I didn’t believe you. I didn’t believe it would happen. But you were all in, right from the start. You committed without looking at a business plan or doing due diligence. It was incredible.

JZ: I can’t responsibly say that I encourage that kind of investment style. I had previously invested in other companies focusing on workplace culture, so I knew and loved the space.? But I’ve always aimed to be a heart-first investor, and that was definitely what happened here.?

NE: Which is exactly what was so extraordinary about your investment. I think that taps into what Translator is all about. Leading from the heart with empathy, specifically in our professional spaces. The past two years have shown us that what people want from their workplaces has never been more important. Globally, voluntary (avoidable) employee turnover is costing employers $3 trillion every year. In order for this economy to be successful we need more people working not less, so it’s critical that we are able to both attract and retain talent. But if you don’t understand your employees, how can you possibly retain them or get them to refer you to their friends and family? You can’t! But you can solve this problem through active employee engagement and culture change. Translator gives companies the tools to facilitate these difficult conversations in the workspace and the data to back it all up. I believe that overall, companies want their managers to have more empathy, and I believe technology can make this happen by helping your employees to feel seen and heard. It’s the little things that make the difference between inclusion and exclusion, and Translator helps you to identify these opportunities and make things better for your employees.

JZ:? I know it has been a journey for you and you have faced? a lot of challenges. It was another year before I saw you again in person. Can you talk a little bit about where you were at that point?

NE: It was not great. We met in New York, and both myself and Translator were going through a particularly rough transition as I had just separated from my co-founder. You asked me how everything was going, and I remember being so scared to tell you the truth. But I also didn’t want to lie. I wanted to be authentic, and so I decided to just be me and be honest with how much I was struggling. But I also immediately regretted it. I thought I had made a huge mistake, and I was terrified that I had scared you off.

JZ: I will admit that I was overwhelmed, but I never doubted you or your vision. I only doubted myself and whether or not I could be the investor you needed. I always want to be a helpful investor, and I was worried that you and Translator needed more help than I could give at the time.

NE: It’s still so amazing and affirming to hear you say that. Thank you for being you.

JZ: I had a hard think about it, and I realized that there was more than one way to be a helpful investor. So I made a connection for you, and that connection helped you redo your investment pitch and deck. I paid out of my own pocket for it, and that felt like to me, the most important way I could help. I remember you being a little apprehensive about it, but you agreed.?

NE: And it ended up being a gift like nothing that had ever happened to me before. I’ve come to realize that I still have so much trauma from my previous life, where people only did things for others because they wanted something in return. There’s always a price, which was why I was apprehensive, and yet you just gave me this gift. A gift that fundamentally changed the game and allowed Translator to get back on track and in the driver’s seat. It was one of the first times I truly experienced the bond of pure sisterhood, and it was profound.

JZ: I can’t tell you how much it means to me to hear that. Thank you. You and I have talked about this, and we both believe that what the world needs right now is not just words, but actions to support one another.

You’ve now founded two companies; one presenting as a cisgender man and one as a transgender woman. Have these two experiences changed what you’re looking for in investors?

NE:? With my prior company, I relied heavily on the old boys network, and it was almost easy because I “looked” like everyone else. However, with Translator, I went back to the usual investors and it was a complete waste of time. It was also an incredibly harsh wake up call, and it completely changed what I now look for in investors. I want to work with investors who are driven by both returns and a mission, and more importantly, I want to work with people who share the same values as me. But this new focus also came with a lot of hangups, because I never wanted to be someone’s charity case. I wanted people to invest because they believed they would get returns, and that just wasn’t happening with my old networks.?

So I went looking for new networks. I joined Start Out, Out in Tech, and NGLCC, three incredible networks who helped me to find the right investors who took me and Translator seriously. More importantly, it helped me to see that when you find the right investors, it’s never charity. My old network taking meetings with me because they felt like they “had to” and not because they believed in me? That was the charity.

JZ: Given your experiences, how can investors be more welcoming and open to founders from marginalized backgrounds? What do you think it will take for the VC world to properly and at critical mass be more inclusive?

NE: Venture Capital as a whole is incredibly antiquated and archaic, and so there are so many things about it that need to change. But the most important thing is taking away all of the unconscious bias that prevents so many people from getting in the door in the first place. On this front, there is this incredible fund out of Covington, KY called Connetic Ventures. They have created an Artificial Intelligence (AI) bot to do all of the initial screening of the applications, and they have an open portal that anyone with an internet connection can access and apply to. The AI advises the partners on which companies to fund, thereby removing the unconscious bias in the selection process. As a result, their portfolio consists of 72% non-straight-white-male founders to date! Which is extraordinary and much more representative of the real world.

But there’s so much more that can be done beyond removing bias. VC needs to be more serious about funding first time entrepreneurs, especially those from marginalized backgrounds. We need funds to seed this first generation of founders, maybe with smaller checks, but we have to be willing to let them try and fail in order to create a second generation of founders who have failed and learned from that experience. Investors also need to be more willing to provide honest and constructive feedback, because if they don’t, the founder can’t learn and grow. Investors shouldn’t just ignore founders if it’s a “no”. That is borderline evil to me. And finally, the way founders are funded needs to be addressed as well, because it often has to be by unanimous vote. All you need is for one partner to have a “feeling” that is really just unconscious bias, and it’s game over for that founder. Maybe we don’t need an unanimous vote for marginalized founders.

JZ:? Right on Natalie. This is exactly why I have spent so much time identifying and funding first time, early-stage fund managers who are women+ and BIPOC, as they are more likely to identify and invest in those founders. Is there something you would like to end on?

NE: Yes thank you! When I do talks or interviews, I always end with my three principles, and I like to share them as hashtags:

1. #representationmatters - A diversity of perspectives, whether it’s VCs, founders, boards, panels, teams, whatever; a diverse representation of different lived experiences and perspectives is good business. Period. It de-risks decision making, it shows people the possibilities of what they can be, and it helps draw good talent. If you can’t see it, you can’t be it, so yeah, representation really matters.
2. #languagematters - I believe that everything happens through language, because there are many different types of language: written language, spoken language, body language, coding language, etc. And if everything happens through language, then our language is important, and we have to be careful with what we say, how we say it, and how we act. The difference between inclusion and exclusion is very subtle, so we have to do the work.
3. #allyshipmatters - Saying you are an ally is easy. Being one is much harder. And you really can’t call yourself an ally. Ask yourself if others would call you an ally. Pro tip: chances are you are stronger in one area of allyship than others, so continuously audit your allyship footprint to ask yourself where you can improve and then do the work!

JZ: I love those principles. Heck the heck yes! I have recently taken a hard look in the mirror and asked myself, am I working on myself enough? Am I truly living the values I espouse? Am I willing to accept feedback that is hard? Willing to call out others and risk fracturing relationships in the hopes that we can grow together? The answers are yes, but I am a work in progress. In my book, people with exceptional levels of power and privilege, which of course includes large amounts of financial resources, have a responsibility to do more and do better.??

Thank you so much Natalie! I can’t wait to see where you and Translator go next.?

NE: Thank you Jacki for the opportunity to represent today in this article. To all of our readers, if you want to continue the conversation you can find me on Instagram and LinkedIn, or you can email me directly at [email protected].