Reflecting on 5 years in VC: How to survive the marathon

The beginning of September is an important time for me as it marks my “VC anniversary.” Five years ago, I was hired as an analyst at Version One and now it’s an absolute privilege to be joining Boris as a General Partner. I’m so grateful for everyone’s congratulatory wishes and kind words last week. These five years have been an incredible journey and I know it’s only the beginning; after all, VC is marathon!

In the past, I’ve reflected on my experiences. Last year, I shared how Boris and I met, along with some thoughts on “Moneyball for VC”. And I wrote about some lessons learned 1 year and 3 years in. 

This year, I’m going to do something different. Instead of my traditional “key learnings” blog post, I want to share how I prepare myself to perform at a high level everyday. This is the fuel that has helped me get to this point, and will hopefully enable me to stay sharp and sane on this long journey in a fast-paced environment. So, here are my five pillars:

  1. Health

Despite having had 4 knee surgeries in the span of 9 years, I’m probably in the best shape of my life – even after “retiring” from Ultimate frisbee. I can attribute this to being disciplined around running 5-7km about 4-5x a week. Before I set out bright and early (530/6am!), I come up with a “goal” of what I want to think through when I run… whether it is the content of this blog post, how to have a difficult conversation, etc. Even better, sometimes my mind is completely clear when I run… to the point where I am essentially meditating and living in the moment.

I also do Pilates every day; this has taught me to be mindful of my breathing while strengthening and balancing me. And of course, there is diet to consider. I’m still very much a foodie, but I do watch what I eat and try to cook as much as possible so I know what I’m consuming. I don’t count calories but this is what works for me:

  • No dairy (I recently found out I’m lactose intolerant, but sometimes cheat with ice cream)
  • No “drinking your calories” (only water and tea, and no alcohol)
  • No caffeine (in order to help with my sleep)
  • Avoid added sugar
  • Always salads for lunch
  • Minimal carbs (though I can’t resist fresh bread or croissants)
  1. Time management

Time is one of our scarcest resources. There are countless productivity hacks, but one of my favourites comes from Phin Barnes’ blog post on aligning your schedule with priorities. I’ve decided to take on an adapted version of his calendar system. I now try to minimize scheduling meetings further than 2 weeks out. Some advanced scheduling is unavoidable, like board meetings, travel, and conferences. But generally speaking, if a meeting is not critical to take today, it certainly won’t be important two weeks from now.

This “system” is great for a few reasons:

  • It forces me to ask myself if I really need to take the meeting to begin with instead of simply putting it off (since my policy is that I have to take it within 2 weeks).
  • I am not booked up so far in advance that I am unavailable for last minute meetings or serendipitous encounters. Nowadays, it’s very rare that I can’t take a meeting within a day or two if I deem it to be high priority.
  • I now have breathing room in my calendar for thesis development and other projects that we work on at Version One.
  1. Creation

Being an engineer by training and launching Insight Data Science means that there is a part of me that definitely misses “building”. In VC, we are constantly consuming… through our conversations with others, reading, podcasts, etc. I’ve recently realized that this heavy imbalance towards consuming versus creating personally exhausts me. I need creative outlets. To recharge, I play the piano, I write, I draw, I cook, etc. I do things that allow me to use my hands and be creative… and not always be stuck in my head.

  1. Heterogeneity

Silicon Valley is very much a bubble. And it doesn’t help that VC is not just a job, but is also a lifestyle – it just makes it that much harder to separate work from life. I am the daughter of a refugee of the Vietnam war who grew up in inner city Toronto. Silicon Valley is my home, but it’s also far from home. I think it’s important to stay grounded to your roots and maintain a diverse perspective.

Thankfully, investing outside of the SF Bay Area means that I make frequent trips to Toronto, NYC, Vancouver, etc. And while I know these hubs are not fully representative of US/Canada or the world, these visits are a nice reminder of the different (and common) opportunities and challenges facing each region, and how different metropolises live and thrive.

  1. Tribe

We know that VC is a collection of competitive lone wolves. This is why I am so grateful for the handful of investors (outside of Boris and V1) whom I trust and share everything with. All the rumors about venture capital being a lonely business are true. I think back to what I wrote:

“[VC is] highly intellectual work and it’s important for you to be challenged with diversity of thought. Some of the best advice I have gotten is to surround myself with a tribe – some of my best sparring partners are friends at other funds. Also, work to build a community around you and think of ways in which you can elevate and develop others.”

On a personal note, given my share of ups and downs this year, I am extremely grateful for the compassion and support not just from family and friends, but also from my “work family”, my tribe, and the best partner I could ask for in Boris.

If indeed VC is marathon, I’m glad that I’m preparing for the eventual back half – and I’m very proud of and excited by what we are building at V1!

-ange 🙂


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