9 Questions For Jacqueline Garavente

Sar Haribhakti
Startups & Venture Capital
5 min readApr 13, 2017

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About two years ago, when I decided I wanted to explore a career in tech. Besides getting active on Twitter and significantly widening knowledge base of ins and outs of tech via newsletters, blogs and tech press, I made a relationship action plan. It’s a concept popularized by Keith Ferrazzi in his book Never Eat Alone. I made two lists. One was for people who are super connectors in NYC tech. And, the second one was of people who are profoundly intellectual and experienced. Second list was for people I wish to get mentored by. Albert Wenger of Union Square Ventures was on that list.

I have been keeping up with USV’s updates ever since. Whether this means following Albert’s blog continuations, Fred Wilson’s blog AVC or the USV team on Twitter.

That’s how I got to know of Jacqueline Garavente. She joined USV about six months ago. She previously worked at IBM and Dataminr.

Last year, I read her blog post titled Luck, Skill and Poker. I loved it and found myself agreeing with every bit of it. I often revisit it. Highly recommend reading it before you go on to read my interview with her.

Sar: What framework do you use to make major career decisions?

Jacqueline: I’m incredibly disorganized with this concept, but I think the most important thing when making big decisions is to know yourself and what makes you happy, regardless of conventional wisdom.

Conventional wisdom, especially for young people in the tech industry, encourages you to try and climb the ladder, become the CEO of a multi-billion dollar company, engage in a PR tour and surround yourself with the “right” or “important” people. I don’t see anything wrong with this pursuit, it’s just not for me.

The truth is that I’m not built to be the person in the spotlight, and I appreciate that part of myself. Also, when it comes to interacting with people, the less important the better. I couldn’t be Mark Zuckerberg (for a lot of reasons) but mostly because I don’t aspire to be a CEO at the forefront like that. I’d be happiest as the Bobby Murphy to someone’s Evan Spiegel.

Because of this, my evaluation for career decisions tends to be quite different. When it’s time to make a career change, I pursue jobs that are intellectually stimulating and ask how the job helps me enhance my own analysis and decision processes. One of the greatest favors I’ve done for myself is to chase intellectual pursuit over salary.

Sar: What’s your take on how students starting out should think about this notion of luck and skill?

Jacqueline: I wrote about that in the blog, but mostly I tell students not to feel discouraged when things don’t go according to plan. I laugh now thinking about what I wanted my life to be when I was 20. At one point I dropped out of college, at another I was forced to take health leave at a job. Life throws curve balls and plans get messed up through no fault of your own. The best thing you can do is grieve the loss of your brilliant plan, and move on to the next best thing.

Sar: Naval Ravikant recently tweeted “Value is seeping out of the venture business and into public blockchains where, ironically, individuals can play but VC funds cannot”. Do you or folks at USV agree with that take? How do you think the VC business might change when blockchains go mainstream as a payment or value infrastructure.

Jacqueline: I can only speak for myself, but I don’t agree with that take. It all depends on what you define as participation in the public blockchain. If you’re talking cryptocurrency and tokens, USV has made a conscious decision to participate in that area through our investment in Polychain. We have provisions in our fund documents that allow us to invest in a structure like Polychain as well as directly in tokens themselves. Not every VC firm is built with those provisions, so it will vary.

Another part of the blockchain is the layer that allows for applications to be deployed. This is another area where VC’s can participate. One of our portfolio companies I am most excited about is Blockstack. The founders are absolutely brilliant and they are providing a decentralized domain name system (DNS), decentralized public key distribution system, and registry for apps and user identities.

Sar: Earlier this year, you wrote about digital currency for virtual worlds. Have you come across interesting products or use cases at the intersection of blockchains and VR so far?

Jacqueline: A couple! But all pretty early research projects. I’ve become obsessive about the development of standardization to create economies of scale in content development, and an in world currency.

One company I’ve seen that falls along this axis and is a bit further along is LivePeer. Really neat idea, sharp founders

Sar: What have you changed your mind on ever since you joined USV?

Jacqueline: Too much to fit in this space. Hard to change my mind on notions of VC because the truth is that I knew nothing about VC before this job. All of that information is new.

The one big change for me has been in the way I view leadership. Prior to USV, I spent very little time with those in leadership roles. Now, spending time with leaders is most of my day. My big wake up call was recognizing that I hadn’t seen a good leader in a professional context prior to this role. Because of that, the most interesting piece of my role has been anthropological in nature. It’s been a test of my value system.

Sar: The debate on whether venture capitalists should have operational experience is almost like the one on whether designers should be able to code. Where do you stand on it?

Jacqueline: Hm…The truth is that I don’t know what it takes to be a great VC, I’m only 6 months in! What I will say is that being on the operational side has really helped me evaluate companies and has helped with my pattern recognition. I do think it’s a deeply personal thing, though, and certainly wouldn’t fault someone who doesn’t have that experience.

Sar: When you come across a new product, how to do think through it for assessing investment potential?

Jacqueline: The first thing I think about is whether the product serves an actual need and then move on to defensibility. Because I look at a lot of machine learning companies I am laser focused on data, barriers to entry, the use case and defensibility.

Sar: What one thing do you disagree with on with other VC associates and analysts?

Jacqueline: I really don’t enjoy being in San Francisco. I’d sooner spend time in the underworld.

Sar: What do you think won’t change in next five to ten years in tech?

Jacqueline: Women being under appreciated.

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