Swimming Through the Chasm

Monique Woodard
Jan 17, 2018 · 3 min read
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My first week at 500, I almost drowned. Like, for real. The cap off to our Mexico retreat was a boat ride and a surprise swim to Marieta Islands hidden beach. I’m a decent pool swimmer, but I probably shouldn’t be in deep water. Despite all that, I took a deep breath and swam through the chasm at high tide and came out on the other side to this beautiful, private beach.

That day, I discovered not only that I could swim, but that what was on the other side was worth swimming to. Being at 500 feels a lot like drowning sometimes, but it’s taught me that I can swim in any situation and given me a crazy group of investors from all over the world to swim with.

Flow is the mental state where you find your focus and rhythm, but it is also about accepting and making space for the positive things that are moving in your direction.

Increasingly, the things that are flowing in my direction exist outside of my current role and in order to accept these new things, I have to let go of the old things.

So I am leaving 500 Startups.

This was a decision that took a lot of thought and ultimately hinged around one question:

Would I be taking something away from founders?

The decision to not be at 500 advocating for investments in companies and acting as an access point for underrepresented founders in particular could mean that I would be taking opportunities off the table for the founders who need it most.

But I’ve decided that there are even bigger doors for me to open.

Sending immense gratitude to Dave McClure and Christine Tsai for creating a place that hired women investors long before it was the thing to do to hire a female partner and for investing in women and minority founders long before it was an industry-wide point of discussion. I will forever remember the two of you for creating the global platform that has allowed us to invest in and support entrepreneurs all over the world.

500’s mission to fund the best founders all over the world continues to be an important one. I do believe that at least one of the tech industry’s top startup accelerators should be run by a woman (+ a woman of color) and I’m rooting for Christine Tsai.

Without 500, I would not have had the chance to invest in and/or mentor companies that I believe in: Blavity, ROHO, Flye, Printivo, Win-Win, Level Therapy, Silvernest, GovList, UrbanLogiq, CourtBuddy, Fyodor Biotech, MailHaven, O.School — as well as every other 500 founder I’ve come into contact with.

In spite of the challenges that 500 faced last year, there is something that has always been a high note…it’s the people.

Marvin Liao, Clayton Bryan, Chris Neumann, Rebecca Woodcock, Tanya Soman, Max Fram-Schwartz, Aaron Blumenthal, Mike Sigal, Sheel Mohnot, and Arjun Dev Arora have been the engine of the 500 Startups accelerator and while I’m already missing you all like crazy, I look forward to many more years of collaborating, co-investing, and occasional axe throwing.

Because I’m not going very far. I plan to remain in venture and keep investing in companies that are creating new markets and founders who have the grit to swim through a chasm of their own.

I’m especially excited about my angel investment in Mented Cosmetics — a direct to consumer beauty brand for women of color (Asian, Black, Latina, Middle Eastern, multiracial). I’m excited to continue to meet an and support talented founders taking on new markets and building exceptional companies.

You’ll be hearing more from me soon. In the meantime, I’m out swimming.

With love,


P.S. You can find me at www.monique.vc and you can reach me at hello@monique.vc.

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