THE TRAIL BLAZER.
Soraya Darabi is the kind of Cover Girl every young woman should aspire to be.
She covered Fast Company’s “Most Creative People in Business” issue, then showed up on Inc. Magazine’s “30 Under 30” list in 2012, only to land on Fortune’s “40 under 40” list three years later.
Her business train moves as fast as her brain and as such, some have dubbed her a serial entrepreneur. But that doesn’t bother Soraya– not in the slightest. She began her career as the Digital Marketing and Social Media Manager at The New York Times at 23. She moved into entrepreneurship with the launch of Foodspotting, which she co-founded in 2011 and was acquired by OpenTable for $10 million, and then Zady, anti-fast-fashion e-commerce destination described as “The Whole Foods of fashion,” in 2013.
Through all of her ventures she’s never glamorized startup life.
Rather, she’s crystal clear on the romanticized version of startup life the media likes to play up. She says entrepreneurs need to be stern if they want to see their idea succeed. At present, she’s General Partner and founder at New York-based venture firm, Trail Mix, which invests in “the future of living well.” Investments include The Wing and Parsley Health.
More from Soraya below.
Name: Soraya Darabi
Instagram Handle: @soraya
Business Instagram Handle: @trailmixvc
We think hybrid models in all areas of business are the future. As someone who has been voted “most creative” by Fast Company. What does it mean to be “creative” in business?
To be creative in business you have to live in both the present and the future. In the present you should create an environment for yourself, whether you work for yourself or a company, that is your own personal culture. Imagine starting a business from scratch and writing a memo that at first only you can read, called “MY COMPANY CULTURE.” What would go on that memo? Personally, I would write down words like flexibility, reflection, movement, excitement, dynamic conversations, brainstorming, imagining, gut-instinct. These are words that guide how I operate in business, but the words may be very different for you. Creativity is about inventing a system for yourself, that ultimately allows you to flourish within a larger construct.
What would you say has been the through-line of companies that you’ve founded and invested in?
Honestly, I’m not sure there is a tight soundbite or perfect through-line of the companies I’ve worked for, founded or invested in. Generally speaking I am drawn to work whereby I can learn from a mentor or colleagues, when the work is purpose-driven and design driven. I like pushing the envelope of what is expected in business and in life, and I believe the companies I align closely with – especially now at TMV – are edgy and bold. Beyond that, my mother the professor, always reminded me growing up that people change professions frequently. College students change their majors at least 2 times on average. Change is a word we embraced in my household because change leads to growth. Now, as an investor, I gravitate toward founders who relish in the new and push boundaries.
For our reader, she’s young, entrepreneurial, but at times fearful of the next step. As someone who has shifted roles and founded new businesses, how have you decided when it’s time to step down and/or move on?
There is absolutely nothing more terrifying than leaving a role. It takes conviction, thoughtfulness, and time to make that plunge. I suggest before making a move formally, to ask a few friends to join your ‘personal board’ and to meet with them once a week or once a month to help prepare you for that next step with a detailed plan that you can be held accountable to. Love and support is the best way to get out of a rough professional patch and into the clear.
How do you feel about the characterization of “serial entrepreneur?”
I don’t mind it, I think entrepreneurs who begin many companies are eager to make a dent in the world. It’s an earnest desire to build a business with lasting impact. I would rather be known as a serial entrepreneur than Sally from HR.
What are the common challenges you’ve seen among female business owners and entrepreneurs?
I see women in business having difficulty pitching their idea and their mission effectively, economically and confidently. Once I feel like I am a black belt in pitching myself (Im not!) I would like to offer free coaching for women entrepreneurs specific to public speaking and presenting. I’m not alone in wanting to help women in this way. The newly launched Female Founder Office Hours will be a great way for women to practice their pitch in front of some of the most senior women in venture in a supportive environment with the goal of helping them present beautifully to the outside world.
With Trail Mix Ventures what was the turning point that convinced you, it’s time to take matters into my own hands?
I knew that incredible companies in New York and Los Angeles were being overlooked by venture capitalists and saw that as an opportunity to launch my own fund to invest smartly, and sincerely, in purposeful businesses. That’s it.
Where do your drive and passion come from?
I am a child of an immigrant. My passion comes from the pursuit of the American Dream.
When you run into a career obstacle, what drives you forward?
A night out with my friends who put work into perspective and remind me to let loose and to have some fun. Dancing drives me forward.
What is your biggest pet peeve?
Unanswered emails and texts.
What are your biggest fears about running a business?
I’d rather answer that question with this quote: “‘You gain strength, courage, and confidence by every experience in which you really stop to look fear in the face. You must do the thing which you think you cannot do.” – Eleanor Roosevelt
What’s something you’d like people to know about your job that they probably don’t?
Investing isn’t only for MBAs and left-brained. My line of work is both creative and intuitive, and some of the best investors in silicon valley began as journalists (as I did) because of their innate curiosity and love of truth. So if you feel like a futurist and you want to be on the pulse of what is next, please consider a job in venture.
Every day there is someone in your shadow. How can we stay original when we are so saturated by other people’s work?
I think you get momentum from competition but keep your eye on the prize and stay focused and calm. That’s all any of us can do. That, and, deleting Facebook from our smart phones.
What about your career makes you feel the most complete?
I feel complete in my career when I push myself – or our team pushes itself – to a finish line we never thought we would get to. I feel complete when I learn and then master a new skill (like pitching institutional LPs). It feels wonderful to be in a position to learn new things on a daily basis.
If you had to trade jobs with anyone else in the world, who would it be and why?
I would trade jobs with a popular playwright. As a teenager I wrote plays in my downtown and once had a play quasi-produced. It is a great hope that I will go back to those early works and workshop them to life again, with an adult vocabulary and prospective. So I think I would trade jobs with Neil Simon.
At what point in your career did you find the confidence to really take charge and become the woman you are today?
The woman I am today is purely because of my Grandmother, Elizabeth Fennelly, a great early influence, a true philanthropist and a very kind soul, and my brilliant mother, Katherine Fennelly, who raised my sister and me on her own terms while pursuing work that was not only meaningful to her but to the world. I think without them supporting my dreams and ambitions I would be without the confidence and resilience I have at this moment in life.
What’s the best advice you’ve ever been given? Or your favorite piece of #realtalk?
Just to remember breathe and sleep. My mother always says “Everything will be better in the morning, but only if you’ve had a good night’s sleep.”
What song do you sing in the shower when you’ve had a bad day?
After a bad day, If I’m in the mood to sing, I would go with Everybody Hurts by REM.