A reflection on a decade: 10 lessons after 10 years in VC

It may not feel like it, but fall is upon us. Professionally, this is always a reflective time of year for me and today, it’s even more so as I entered the world of VC ten years ago. Ten years. Where does time fly?

On my first “VC anniversary,” I wrote about how VC aligns with my core values of continuous learning, compassion, and freedom (which is why I love this work and career so much). At Year 3, I reflected on the importance of paying it forward at. At Year 5, I shared how I prepare myself to perform at a high level every day, in order to stay sharp and sane in this fast-paced environment. And then at Year 6, I talked about my first year as a GP and the changes, though nuanced, from being a supportive junior member of an investment team.

Now for Year 10, I want to summarize the principles and lessons that have guided me most. It’s important to note that these are my own thoughts based on my personal experiences at Version One and shouldn’t be generalized to other VCs. In no particular order, here’s what I’ve learned so far: 

  1. Build your tribe. VC can be a bit lonely. It’s highly intellectual work and it’s critical to be challenged with diversity of thought. I’ve done this by surrounding myself with great friends and co-investors at other funds – a handful of them have become my best daily sparring partners (outside of Boris and Leah at V1).
  2. Pay it forward. The ROI on your time and effort in VC is measured in years and decades. You just never know what opportunities will yield results. In addition to hustling and trying to find yourself in the right place at right time, you must pay it forward in a genuine, non-transactional way. In such a human-driven, relationship-driven business, you need to care and be compassionate about everyone’s goals and dreams.
  3. Build the best partnership. I am SO lucky that I get to work with Boris and build our partnership every day. It is one based on a high level of trust, respect, and shared values. We are in constant communication (daily text, emails, calls) because we don’t have the luxury of “water cooler talk” that you get from working in the same location. Also, we benefit from being a small team without any bureaucracy. We believe that it’s good to be contrarian to the rest of the market and other investors, but not to be conflicted in a partnership where alignment should be more important.
  4. Be quick and responsive as a competitive advantage. Building on Point #3, when you have strong alignment and trust, it’s easier to make decisions, provide feedback, answer emails, etc., within 24 to 48 hours (90% of the time). Even when founders don’t get the desired response, they still appreciate our quick turnaround and even forward along referrals. In fact, a recommendation from a founder we passed on is one of our best performing portfolio companies!
  5. Be a generalist and a specialist. In a deep ocean of early stage investors, it’s important to signal to the market that you have specific areas of interest, even if you look to invest in everything. In the early days, I focused on anything data science related, then healthcare, and now I proactively look at climate/energy. However, this is not to say that I don’t spend time on nor invest in AI, dev tools, vertical SaaS, marketplaces, etc. (as our portfolio shows). It’s just difficult to be everything to everyone on the outside. But on the inside, you can (and arguably should) be it all. Being a generalist has taught me a lot about how founders succeed in different environments, markets, and business models…and these lessons are especially valuable when building in emerging areas. And of course, it has taught me a lot about the fundamentals of founders which aren’t thematically specific. As such, I’ve learned to develop my filter faster.  
  6. Build a personal brand. This point is obvious, but I’m calling it out because it comes the least naturally to me and is the biggest thing I continue to work on. We all know it’s important to differentiate ourselves individually and not just as a fund. There are many ways to do this, whether it is being active on social media, writing a lot, etc. The key is to find something natural that works for you (admittedly, this is still a work in progress for an introvert like me).
  7. Be a learning machine; stay curious and weird. Founders can easily sniff out if you genuinely care about a new area based on innate interest and curiosity versus potential capital gains. For example, I am curious about crypto but I don’t have the same passion as Boris does in the category, so I defer to him here. Instead, I channel my energy into climate (this hits close to home because my husband is a firefighter) and healthcare (as a Canadian expat, it boggles my mind that we don’t have universal healthcare in the US). It’s also important to be extremely open-minded and put yourself in situations where you can learn as quickly as possible so that you have an educated opinion about things. If you have a genuine curiosity, don’t be afraid to dig into a new area.
  8. Stay optimistic and don’t get too cynical. The longer that I’m a VC, the more skeptical I feel that I’ve become. With that said, I have to remind myself to continue to be open-minded and focused on what a venture can become if everything were to go right. What is the non-obvious long-term vision? Admittedly, the longer I am in the business, the more I also find me second guessing myself – a kind of “imposter syndrome” that probably stems from the cognitive biases that I’ve developed over time… so this is another reminder to keep an open mind and find a balance with the efficiencies I get from pattern recognition.
  9. Ask the right questions at the right time. When I first started in VC, I positioned my value-add as my ability to help on the data side of things. However, I quickly observed that the best value-add investors are not necessarily functional experts or those with the largest rolodex. Entrepreneurs are the domain experts; the best investors are not prescriptive, but can ask the right questions at the right time to help entrepreneurs find their own path.
  10. Invest in mission-driven founders. Contrary to my first assumptions as a naive candidate to VC, at the earliest stages, it is ALL about the founder and what drives their passion towards solving a specific pain point. The startup journey is never straight…in fact, some of our best performing companies are pivots. This is why we place high value in backing mission driven founders who have experienced a problem first hand. Side note: these days we are also spending A LOT of time on “why now?” as well.

Thank you to our V1 founders, entrepreneurs, investors, friends in this ecosystem, and to my (growing) family: you continue to inspire me to give my best every day and I am appreciative of your support and all the incredible adventures I get to be a part of. And of course, a special thank you to Boris for seeing something in me and giving me a chance back in Fall 2013. His leap of faith has given me a career full of learning opportunities and a privileged life that I would’ve never imagined as a young girl growing up in inner city Toronto as a daughter of refugees.

Here’s to the next decade!

PS Here’s a fun relic from Day 1 taken with my iPhone 4 and when we had business cards, used Skype, and had yet to update our logo 🙂

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