Entrepreneur-turned-VC: Startup Tips with Soraya Darabi, General Partner at Trail Mix Ventures

Meet entrepreneur-turned-investor, Soraya Darabi.

Soraya Darabi is Co-Founder and General Partner at Trail Mix Ventures (TMV), an early-stage investment fund based in New York City that focuses on the future of living well. Her three main investment areas include tech-enabled sustainable solutions, the care economy, and the future of work.

Soraya doesn’t however come from a traditional VC background like finance. She started her career in the media industry, managing digital partnerships and social media strategy at the prestigious New York Times, after completing a degree in Liberal Arts at Georgetown University. She then entered the tech industry, first working for a startup that sold to Facebook, then co-founding Foodspotting which sold to OpenTable. She has appeared on the cover of Fast Company’s “100 Most Creative People in Business” and also been named on Inc. Magazine’s “30 under 30” list as well as Fortune’s “40 under 40”. Soraya’s experiences are diverse and that has helped her better nurture and advise the startups in which she invests.

Soraya has served as a member of STATION F’s Selection Board for the past three years, helping select the startups that join the Founders Program, our program for early-stage startups. We asked her to share some startup tips as an entrepreneur-turned-investor and to shed some light on how she evaluates startup applications.

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You started your career in Media (Conde Nast, The New York Times) and moved on to entrepreneurship (working for a startup that sold to Facebook, then co-founding Foodspotting which sold to OpenTable). What are some of the most important lessons that you learned from operating ahead of becoming a VC? 

S: It’s funny, but managing a startup is a lot like owning and operating your own early-stage venture fund. You have to come up with a clear value proposition, understand who your stakeholders are and deliver the right information and data-points to them, you have to communicate well (and learn to over-communicate at times), you need to raise capital and do so without taking your eye off of the ball as we say in the States.  So actually everything I learned in my 8 years of working as a startup operator plays into how we make decisions at TMV. At Trail Mix Ventures we are 5 operators who have 7 startup and company exits between us, including 1 IPO.  We have been through what the founders we invest in are experiencing, and that founder to founder empathy makes us better investors in the long-term.

As a Founder and General Partner of Trail Mix Ventures (A holding company with two early-stage funds), what are the key things that you look for when someone pitches you a startup idea?

S:  Within the three main categories we invest into (Tech-Enabled sustainable solutions, the care economy and the future of work) as a team TMV looks for founders with strong domain expertise. That’s first and foremost.  We also look for a first-to-market or early-movers advantage when tackling a problem within a massive addressable market.  Then, beyond standard due diligence we ask ourselves questions like “are the founders good people, whom we could imaging partnering with for a decade to come?” “is there diversity on their cap table? diversity on the founding team? on the advisory board?”  we invest 50% in men and 50% in women-led teams and we see this as a modern imperative – not just a nice to have. 

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How do these criteria differ from how you evaluate startup applications for the Founders Program at STATION F?

S: The criteria is similar.  For STATION F I adhere to their guidelines more so than my own formal guidelines at TMV.  I look to vote favorably for teams that demonstrate a solid understanding of their market and opportunity. I favor data-centric pitches and teams that have some traction to show – be it an early beta product, early monetization results or great user feedback.  

What is your top piece of advice for entrepreneurs starting out?

S:  My best advice to entrepreneurs starting out today is to spend a lot of time thinking through the idea you will ultimately run with, because this concept could be the next 20 years of your life.  So I encourage them to love their business and to be as bold as possible when imagining the future potential, but as granular and specific as possible when getting from idea on a napkin to product market fit. 

In choosing a co-founder to start a business, what matters most?

S:  At TMV we look for founding teams who have worked together before.  We favor this dynamic over any other.  It can be scary investing in a husband and wife or siblings or life partners because the business starts out on a slightly more emotional level.  Rather a team that includes two people with disparate but complementary skill sets and a background relevant to the business they are starting is always the right way to get our attention as investors. We also look for folks who can attract talent so we favor 2 founders with at least 1 employee over solo founders.  And if you are a solo founder, show us you can attract talent by demonstrating a great advisory board. Just don’t make that advisory board too big — show us that you are working with experts who are leaning in with time and/ or capital.    

What apps or methods do you use to be more productive or to enhance your well-being?

S:  I use a Trello board for staying on top of my tasks as well as the iCloud notes app.  For my personal management of a rolodex that’s relevant to venture capital and startups I use Copper, which is an extension for Google chrome.  I also use the calendaring application Clockwise.ai for our team and recommend it to every startup we invest in.   For my personal well-being I am a big fan of hiding social media applications into one folder on your mobile phone and taking them off of the home screen. This allows me to stay productive and not give into social media FOMO, particularly during a work day. 

Interview by

Cindy Yang
[email protected]