Jason Malki
Aug 27 · 9 min read

As part of my series about “the five things we need to do to close the VC gender gap” I had the pleasure of interviewing Gwen Cheni. Gwen is currently a Venture Partner at Fusion Fund, an early-stage venture fund with more than 50 portfolio companies, and an Entrepreneur in Residence at Singularity University Ventures. Her love of technology started early growing up in SF, and solidified when William Hewlett, an alumus of her high school, donated a brand new computer lab. Before venture capital, Gwen was the Assistant Portfolio Manager at a technology focused hedge fund in San Francisco. She started angel investing in 2012 and loves growing companies with founders. Prior to venture, Gwen spent eighteen years investing in the public markets, and started her career as an Analyst at Goldman Sachs, and an Associate at J.P. Morgan. Gwen’s traveled to 70 countries and counting, attempted to learn seven languages, and admittedly mastered none. She received her BA from Yale University with a major in Economics and minor-equivalent in Computer Science Electrical Engineering, where she graduated summa cum laude and Phi Beta Kappa. She received her MBA in four concentrations from The University of Chicago Booth School of Business with Honors.

Thank you so much for joining us! Can you tell us the “backstory” that brought you to this career path?

I’ve been an investor my entire professional career. Having grown up in the Bay Area, tech has always been in my blood. Three boom and bust market cycles later, I finally made my way back to tech and couldn’t be happier. I love working with founders to build businesses, and seeing cutting edge technology makes me feel like a kid in a candy store. I’m a rational optimist, so venture capital fits me better than any other asset class.

Can you share a story of your most successful Angel or VC investment? In your opinion, what was its main lesson?

I invested in an alternative energy company in Europe that captured and stored the kinetic energy of waves. It was acquired by a legacy utility company in Europe in a year for a multi-bagger. The biggest lessons there were:

  1. Opportunities can happen everywhere. I met this founder at a house party with a few McKinsey consultants in Amsterdam.
  2. People is everything in this business. Through the group of consultant friends at the party, I was also able to reliably vet this founder, both character and technical expertise.
  3. While waiting for big IPOs is the holy grail of venture investing, an argument should also be made for quick exits. The company ended up being badly managed at the utility company and went to zero.

Can you share a story of an Angel or VC funding “failure” of yours? Is there a lesson or take away that you took out of that that our readers can learn from?

I have many deals I should have swung at, but most angel investors have less capital than large VC funds. Angels have to choose between either small checks in many deals, or big checks in tiny number of deals. I made the choice to write same sized checks as VCs, which meant fewer number of checks. As I transition more to the VC side, I’ll certainly take more swings going forward.

Was there a company that you turned down, but now regret? Can you share the story? What lesson did you learn from that?

I had the opportunity to join Google in 2002 as a junior engineer working for my Teaching Assistant from Algorithms course in college. I had just started at Goldman Sachs as an analyst and stayed on the traditional/safe path to pay off my college tuition loans. In retrospect, I should have jumped at the opportunity to work for the most brilliant female engineer I’ve ever met and the kindest person to boot. Always choose people over any other factors.

Ok let’s jump to the main focus of our interview. According to this article in Fortune, only 2.2% of VC dollars went to women in 2018. Can you share with our readers what your firm is doing to help close the VC gender gap?

Fusion Fund was started by a woman, Lu Zhang, who was named Forbes 30 under 30, so the gender bias was never an issue. I believe instead of focusing on gender, we should focus on removing all biases for most people-centric decisions. The classic success story is the blind orchestra audition, which increased the percent of female musicians in the five highest-ranked orchestras in the U.S. from 6% in 1970 to 21% in 1993. Venture is more multifaceted, but reasoning from principles and having a list of success drivers, what the presence and absence of each driver actually looks like in an investor, will go a long way to counteract implicit bias in all of us. The criteria should be less about “do I like this person?” “Can I play golf with him?”, but “what are the different types of investors that have won at this?”

Can you recommend 5 things that need to be done on a broader societal level to close the VC gender gap.

  1. I’ve asked all of my male VC friends to request at least one female panelist when they are asked to speak on a panel. Often times the organizers didn’t even think about it, but the request brings the implicit bias to light.
  2. When I’m organizing events, I make sure to have at least one panel that is all female VCs and investors, or all female founders and engineers. One of the most frequent pushbacks is “there just aren’t enough women”. I take every opportunity to shine the spotlight on the brilliant female VCs and founders that I’ve been lucky enough to come across. Trust me, there are enough, they just aren’t getting enough credit.
  3. When I get pitch decks from female founders, I take the time to reply with immediately implementable advice for their businesses. I ask them to keep in touch and try to repeat with the same free advice every quarter. Even if I can’t help with capital, I try to at least help with free business and strategy advice.
  4. The VC community is smaller than one would guess from the outside. I want to bring back the old “give before you ask” Silicon Valley culture of the Noyce Moore Grove days. I always keep an eye out for the types of deals each VC is looking for, send them those deals, with no expectations whatsoever. If the community feels more camaraderie, the cut throat mentality softens, and the club will get more inclusive.
  5. Biases exist in all of us, every single one of us. Stereotyping is the mind’s way of taking a shortcut: it’s evolutionarily and metabolically advantageous. Problem occurs when it’s a non-normal distribution, when shortcuts miss the fat-tails and anomalies. Shortcuts also always miss the changing environments. Educational and career opportunities have dramatically opened up to women since our grandparents’ generation, and our mental shortcuts have failed to adapt. This is the root of the chasm. I see gender bias as one facet of the very human tendency for mental shortcuts. Instead of turning the genders or races against each other, we need to question all of our biases.

I was turned down by an LP just last week because I did some runway modeling back in college. Does this really negatively impact my ability to invest in early tech companies almost 20 years later? Or does it increase my circle of competence to understand media and fashion industries, and add a differentiated circle of celebrity connections to my portfolio companies? I also train for triathlons and take pilot lessons. Are these also negative predictors of my ability as a VC, or do they indicate unshakable grit and willingness to constantly challenge my fears? This is why I believe one useful way to guard against unconscious bias is to list success drivers, what the presence and absence of each trait actually looks like, _ex ante_. Making this list ex post makes it all too easy to trigger the human tendency to justify our prior decisions (the A Priori Argument logical fallacy). What I’m proposing here is similar to reasoning from first principles and antifragile decision making. Asking a priori what the success drivers look like, is reasoning from principles. A successful VC is someone who can identify industry and business trends very early, find and partner with the right teams to ride these waves, and network to bring in external resources to help execute. Prior VC and founder experience are definitely ways to get these skills, but not the only way. Reasoning from first principles means working backwards from the desired end results: the desired end result is high IRR, not hiring someone who reminds me of the younger version of myself.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

The old Silicon Valley, of the Fairchild Semiconductor days, instilled the “give first” principle in everyone. It fostered a sense of community and teamwork that’s been slowly deteriorating over the last two decades. Let’s bring it back, and find a way to bring back that sense of community that is Silicon Valley.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Everything around you that you call life was made up by people that were no smarter than you. And you can change it, you can influence it… Once you learn that, you’ll never be the same again.” — Steve Jobs This quotation resonated with me because I had always questioned why things were done a certain way, or why certain expectations are set as they are, even as a toddler that just learned to speak. As you can probably imagine, this did not make me an easy child. I joke that it took my parents fifteen years to forget the horrors of raising me, to finally have my little sister. When I heard this Jobs quotation, it was confirmation that someone else in the universe thought the same way as I did, that it was ok to ask “why” and question the status quo.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this, especially if we tag them. :-)

I was a Big Sister for Big Brothers Big Sisters in NYC and saw first hand the importance of mentorship. There are so many great leaders in tech. If they can each give us just one hour of their time per year, that mentorship, honest dialogue and collective problem solving can boost female founders and VCs. I’m happy to run this program pro bono, just need a few high powered folks to sign up to lead the movement.

This was really meaningful! Thank you so much for your time.

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Jason Malki

Written by

Jason Malki is the Founder & CEO of StrtupBoost, a 30,000+ member startup ecosystem + Flex5, a startup investor relations, marketing, and design agency.

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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