Soraya Darabi, founder of Trail Mix Ventures, is optimistic when she thinks about the wall that women have to climb over when it comes to investing. And the reason is that she’s part of the change in the industry. While only 2.2% of venture capital dollars are going to women, Trail Mix VC’s portfolio is over 60% women founders and the company puts the spotlight on well-being through tech and good storytelling.
In her conversation with Madame Architect founder and AWT columnist Julia Gamolina, Darabi talks about her experience of overcompensation and having to go the extra mile to be taken seriously in a field where women weren’t playing a role for a long time.
Julia Gamolina: At the beginning of your career, you were at the New York Times. How did you get there and what were your takeaways?
Soraya Darabi: I was coming off the heel of my first job out of college, which was working for Conde Nast. My first week on the job I drafted a press release for my boss about the Wired acquisition of Reddit, and it was there that my eyes opened up to the vast and exciting world of technology and acquisitions. Well, maybe not exciting for everyone but it certainly was for me. Explaining internally what Reddit meant to stakeholders at Conde Nast gave me a sense of how valuable it was to be a digital native at a large media organization. Later, I wanted to know why tech companies like Reddit were changing media as we knew it and shifted my career focus to follow that thread.
I earned the job at the New York Times on a former colleague’s recommendation. Landing there was just serendipitous timing. NYT in 2007 was the place to be if you cared about convergence and the effect it had on traditional media organizations. Back then we—the digital team—placed NYT as the first brand in the world to truly leverage social media. Again, because I was a digital native, and because I loved technology through and through, I decided to focus my career on building and evangelizing products that make a difference in the world.
Tell me about Foodspotting.
At the New York Times, my job was to partner with start-ups, large and small. I felt like I had the best job in the world, but I was teaching more than learning. I really wanted more development experience, so Foodspotting was the first company I started advising just after I left the New York Times, eventually joining as a co-founder. The Foodspotting team wanted to help share the idea that great food can be democratized and that you don’t have to have a Michelin star to have the world regard your eatery for a great dish, but what you do need is an app that helps the world sift through the best dishes, based on location.
My next start-up was focused on telling a different story. We aided consumers in their quest to understand how sustainable products, namely fashion, is made (read: terribly, disastrously for the environment) and how the supply chain really isn’t transparent at all. Through technology, we had an opportunity to channel that transparent story in a way that made sense to modern millennials shoppers, who want to vote with their dollars and do right by their purchases. They just didn’t know what the good choices are.
The common thread in all of my work is that it touches technology, internet and mobile, and that it tells a good story.
How did this start-up experience then lead you to starting Trail Mix Ventures?
Trail Mix Ventures began because, throughout my work with start-ups, I was concurrently advising and investing in companies. My teammates and I collectively noticed that the business partners of the companies that were doing the best in my portfolio were focused on health and wellness and something I’ve always personally been very mindful of.
We realized, in digging into the research, that young people that are dealing with student debt are still not willing to sacrifice their emotional or physical well-being. This is why companies like Peloton have sky-rocketed, from Kickstarters to five billion dollar market cap in six years—there is an audience for people, like myself, who don’t want to sacrifice their well-being. The average millennial doesn’t have money saved up for their rainy day and yet they will still buy their ten-dollar green juice, and they will still buy their thirty dollar SoulCycle class. We recognized a trend in behavior that made a lot of sense to us—because what’s more important than happiness and wellbeing—and decided to launch a fund, my two partners and I, dedicated to the future of well-being, which Bill Gates said in MIT Review earlier this year is where he thinks the future of Venture Capital is headed.
What have you been up to since the company’s launch?
At Trail Mix Ventures, we invest in three categories: businesses that focus on general well-being, businesses that focus on mental and physical well-being, as well as businesses that focus on care-taking and the future of primary care, so medicine is very important to us. Lastly, we invest in the future of work as it pertains to well-being. We call all of these different categories really fall into the “care economy,” taking care of ourselves and of others.
The care economy has some of the largest addressable markets. For instance, taking one segment of the population, elder care alone in America is more than a trillion-dollar market. These are massive numbers! No matter how much venture capitalism has shifted away from your typical social media start-up investment, which it has, and which was all the rage ten years ago when I first started in tech, it really hasn’t deviated enough. Care and the care economy is still undercapitalized as a venture and so we are taking a stand and investing in those companies, as well as investing in companies in which women are the core consumers. That’s why over 60% of our founders are women; we don’t only invest in women, but when only 2.2% of venture capital dollars are going to women, it’s exciting to have them as our majority.
I just recently talked to Jean Brownhill, the founder and CEO of Sweeten, and we talked about how even within that number, only 0.2% of dollars go to African American founders that are women.
Right—this is abysmal, especially considering that African American women start more businesses per day—more so than any other demographic! I believe it’s something like 1400 businesses a day. What has taken the world so long? I think those businesses tend to be very small, and thus, according to Silicon Valley, “un-venture-backable.” When you think about who is saying that out of Silicon Valley though, you know—there is still a huge wall for women to have to climb over in terms of investing, and, finally, tides are changing. I’m optimistic.
Perfect segue given what the focus of this column is—since you’re straddling the worlds of tech and finance and venture capitalist, worlds that have long been dominated by and associated with men, how have you navigated that?
It’s still a man’s world! To navigate that, I started my own fund as opposed to taking a job working for someone else! I interviewed at a firm that would have been a dream job by resume standards, but the partnership was all-male and the interviews were incredibly macho and intimidating and I thought to myself, “That’s not the culture I want to be a part of.” At Trail Mix, we invest in trailblazers, so it would be hypocritical of us to not trail blaze ourselves in the way that we do things.
We like the fact that our partnership is women-led—it’s a women-owned general partnership, but there’s diversity on our team. We’re not trying to say that in order to be great VCs, we only invest in women—we invest in men and women, and our partnership includes a phenomenal man. For us, diversity was important to get right from day one, and it’s been exciting to do things differently and for the industry to wake up and see that that will actually yield returns. The data shows that women founders have better returns, dollar to dollar, in venture capital, even though they’re incredibly undercapitalized compared to the guys.
Victoria James said just that—she said, “I’m not sure if I’ve broken through the boys’ clubs—I just went ahead and started my own.”
Audrey Gelman who founded The Wing, a founder we are supremely proud to have backed at TMV, often says, “We’re not trying to break the glass ceiling—we’re building a whole new house.” I love that and agree with her whole-heartedly.
Where are you in your career today?
I’m looking for incredible trailblazers and founders whom we can be with for the first two years of their seed stage until they can get to product-market fit. The fact that I’m, and that my partners all are, former founders and operators as well means that we operate at a high level of empathy. We know what the founder experience is like so every decision we make is based on what we would have wanted when we were in their shoes. Because of that, we’re focusing on our second fund, which will be bigger and bolder and better.
Looking back, what have been the biggest challenges for you in your career?
The biggest challenges for me were always about overcoming stigma; trying to break into someone else’s party never feels very fun. Other challenges for me were having to overcompensate and go the extra mile to be taken seriously in an industry where women weren’t for a long time.
Finally, convincing myself to get over my own imposter syndrome, which is something I think all women face, and tell myself, “I can do this,” was incredibly difficult. I spent many years focusing on work with my executive coach to get over the feeling that I didn’t deserve a seat at the table. I have never met a woman that didn’t have those same self-doubts at one point or another. For me, it took many many years to push those devilish thoughts aside to say, “Eff it—I’m doing it anyway.”
Having now overcome this, what are you most proud of?
I’m really proud of the partnership we have at Trail Mix and the beautiful portfolio of founders we have. It’s the honor of our careers—to work with people who are making amazing, impactful, and meaningful change in the world—whether it’s a food waste business which helps solve food waste and food security at the same time, or a type of recycling business that makes it easier to recycle, or a type of well-being in the workplace that are really beautiful ideas that I wish I had come up with. It’s exciting to be helpful to them in a large or in a small way.
Who are you admiring right now?
I admire my mother, fiercely. She is an academic by training who has dedicated her retirement to helping immigrants and refugees—and to writing a book that tells a fascinating story about our Hungarian relatives. I love that she is using her free time to follow creative pursuits and to be an activist when so many of her peers may decide golfing in Florida sounds more fun.
Finally, what advice do you have for those starting their careers, but especially for women starting their careers in fields that have traditionally been male-dominated?
For those just starting their careers, it’s OK to fail—fail often and fail fast and try to do most of the failing in your twenties. Your twenties are for experimenting and learning. Find a job in your twenties in which you have a teacher or mentor from whom you can learn and absorb as much as possible. Don’t optimize for salary in your twenties, and don’t optimize for a title—optimize for learning and learn as much as you can in different fields. Try three different experiences, for three years each, that are not entirely like one another. Then, when you get to be a generalist by the time you’re in your thirties, you can then pick and choose which of those paths makes the most sense for you.
For women working in traditionally male-dominated fields, share information. Start a tribe, go to lunch together two times a week, and don’t be afraid to be transparent with each other even if it’s uncomfortable. Talk about your salaries, talk about your ambitions, and find ways to help one another. Women really do need to help one another in order to succeed.