I’m leaving VC; this is what I didn’t expect to learn

Article written by Jessica Li




This month, I left venture capital to move to the operating side in a growth marketing role at Zageno. I am thrilled to be working with this amazing team to accelerate innovation in healthcare and excited for this next chapter.


Going into venture capital, there was a lot that I expected to learn on how to think about spaces and companies, how to grapple with uncertainty, and how to support early stage founders. Looking back, I have learned so much more about relationships, learning to learn, personal growth, and life.


Here are the most surprising lessons I am taking from my time in VC:


Intentional Growth

Set intermediate KPIs for yourself. When I first started VC, I was intimidated by the long feedback cycles. You can work diligently everyday but you do not truly know whether your investments will exit successfully for at least 5 years and in many cases (for early stage investors), even 7 to 10 years.


Consequently, I decided to set intermediate KPIs for myself to quantify my own learning at the micro level. I kept track of whether I was asking better questions during each founder call, whether I was making decisions with more independent conviction each day, whether I was making more valuable intros for people in my network, whether I felt I could understand and support portfolio companies in their biggest challenges (denoted in their monthly updates), and whether I was sourcing more high caliber companies each week.


Become a chief of staff for your portfolio companies. Without decades of industry experience and the corresponding network, I was at first unsure how I could support portfolio companies (over time, I did build a network on the job — see the next section).


I quickly realized that my comparative advantage was time and that I could use my time to support startups, which in many cases, could be even more valuable and tangible than a network. I texted and emailed founders to ask what they would do if they had a few extra hours of the day, week, or month and took on any of these tasks that I could from interviewing dozens of candidates to drafting pitch decks to emailing potential customers. In this way, I delivered concrete value to startups instead of just arbitrary advice or intros that end up going nowhere. I also got a real sense of what it would be like to work at a startup, which helped prepare me for my startup interview process and new role.


Never view a task as beneath you. Whenever you first enter an industry, company, or department, you will go through an inevitable, implicit period of proving yourself. You will rarely be able to do the glamorous work right at the start. By approaching each task, no matter how menial, with great attention to detail, a positive attitude, and tender love and care, you gradually gain the trust of those around you to be able to take on more responsibilities, including those more in line with your goals.


See yourself as a product and find your product market fit. When I was deciding to take a role in venture capital and again when I was deciding to leave venture capital, I asked many people for advice. Many of them asked me what my long term career goals were and tried to help me optimize my decision making for this end goal. However, I have just a general idea of these goals and have very broad professional interests — what if I optimized for an end state that I would later regret or seek to deviate from?


A few brilliant mentors gave me better advice: instead of focusing on an ultimate career goal (especially for those, like myself, who are still exploring), see yourself as a product and find your product market fit. Like an early stage founder iterating through different ideas, do the same with each new role in your career. Go into every job with a hypothesis you want to test and a set of skills you hope to gain, regardless of whether you end up staying in the role, company, or industry. In this way, you can deliberately make the most of every opportunity, constantly taking steps to better understand what your long term career goal may be (at the intersection of your strengths and interests), and continuously build a portfolio of diverse skill sets to bring to all future roles.


Find your product channel fit. While the long feedback cycles of venture capital certainly pose the aforementioned challenge, they also present an opportunity: the opportunity for the development of different investor styles. Successful investors do not fit any one particular mold. Some investors are incredibly extroverted and find most of their deal flow through their networks. Other investors are very introverted and like to spend time alone reading, writing, and thinking about the future in a first principles way and find their deal flow in this manner. Most investors are somewhere in between along this spectrum.


I have found myself to be more network driven and have structured my time, brand, and content in this way. Instead of solely writing about my thoughts on the future, most of my publications are focused on interviews with other people. Many of the most important lessons I have learned have been from other investors and founders. Much of my deal flow comes from catch ups with investors who have become close friends. But how do you build strong networks and long term relationships?


Network Building

Never be restricted by the network you came with. Many investors come to VC with decades of experience and a network built up from over a dozen jobs, boards, and business school. Being a relatively young person, I initially felt intimidated and was unsure of what network I would bring to the table.


A brilliant mentor (who is now a general partner at a top fund and joined VC right after undergrad) told me to approach network building with a growth mindset. You should not feel that your network is restricted solely to those people you have worked with or have gone to school with. Identify any growing industry or functional area and reach out to everyone you can in the space. With each interaction, ask for referrals and meet more people. Connect relevant people with each other and host events. Over time, you become a go to person in your chosen space and build your network on the job without having to step foot outside VC.


Reach out to people with no agenda. If your friend publishes an article, email them to share what you liked most about it. If a founder announces a successful partnership or fundraise, message them to congratulate them.


Ask people about their challenges. Check in with people from time to time even outside of any regularly scheduled conversations and ask them what their biggest challenges are. Instead of an empty “I would love to be helpful,” you can show you actually care and quickly get to the heart of people’s most significant obstacles and proactively provide concrete, tailored offers of help to your network.


Share relevant opportunities and articles with people. Whenever you meet someone, take note of what gets them most excited and what is most top of mind for them. Then, whenever you come across a resource in their areas of interest, send it to them. Constantly show people that you have a nuanced understanding of them and they are top of mind for you, even weeks or months after your last live conversation.


Calendar check ins. For those people you have meaningful overlap with, check in with them synchronously or asynchronously regularly. Even with bimonthly or quarterly catch ups, you can build much stronger relationships beyond introductory calls.


Integrate people in your work. Host panels with other investors, invite them to communities you are a part of, share deal flow, or interview them for your articles. Nothing beats actually working together even on smaller side projects like events or content.


Focus on the pretext. The same exact action taken by different people can be construed in entirely different ways depending on their understanding of you. At the beginning of every job and relationship, spend time building trust with people: engaging in water cooler talk, getting to know everyone without an agenda, and offering to help in general and in tangible ways. Get to know people cross-functionally, even those outside of your immediate department. Then, each of your later actions (within reason) will be construed with the positive pretext built on the strong relationship you have with others in your organization.


Join and volunteer in communities. Several months of my time in VC were largely spent remotely during COVID-19 quarantine. Without the ability to spontaneously meet or bump into people at happy hours, coffee shops, or events, I got more involved in virtual communities, such as Women in VC (where I became a channel moderator) and the Emerging VC Association (where I led content).


Beyond and before taking on any leadership roles in these groups, I individually emailed every new investor (who I had meaningful sector, stage, and geography overlap with) and hopped on a Zoom with them. After each Zoom, I shared relevant companies for each investor. Once I had met a significant number of investors, I began introducing them to each other with double opt ins and where there was meaningful overlap. Outside of calls, I checked each channel (in the Slack communities) daily for questions I could answer with links, advice, or intro offers. Whenever I came across a compelling resource or opportunity, I shared with the group.


Be responsive. Even if the answer is no or not yet, people appreciate the closure and the responsiveness. There is almost nothing worse than feeling invisible and ghosted. Even with over 200 emails coming into my main work email account daily, I aim to be responsive to each one and comb through my full list of new emails from the day each day to make sure I indeed have replied to every message that needs or could have a response.


Even if you do not have the bandwidth for a call, ask people requesting calls what questions you can respond to or what materials you can provide via email in the meanwhile.

In a similar vein, when someone makes an introduction, follow up with the introducer after the call to let them know how the exchange went.


Teach people something. Ultimately, all people enjoy connecting with interesting people. If people can feel they took away something concrete: a piece of advice, a fascinating fact, or an introduction from your conversation, you will have delivered value and be remembered positively. Listen first to see what people most want to learn and then aim to show your understanding of them and value in their focus areas.


Meet people early on in their journeys. A seasoned investor may already know the ins and outs of the venture community and have built a large network. While these folks are great to connect with as well, you can often deliver more value to those relatively new to the industry. When you connect with someone who just joined the VC world, you can easily provide tons of useful information, such as general advice, intros to other investors, deal flow, and tips of great investor communities. In short order, you are building a strong relationship with these investors who will always remember you positively.


Lose the 0 sum mentality. To effectively focus on the long game in your relationships, it is crucial to lose the 0 sum mentality. I have met some people in VC and elsewhere who are afraid of opening up their network because they somehow believe that will diminish the utility of their own network for them. This is frankly just untrue. By connecting people to each other within your network and empowering everyone you meet in actionable, tangible ways, you build even stronger relationships and contribute positively to your own brand, which continues to pay dividends.


Smile on audio calls. In this virtual world, we are spending the large majority of our time on audio calls of some kind (Zoom or phone). Even if people cannot see you, it makes a world of difference in the tone of your voice whether or not you smile when you speak. Try it! (Smiling more also makes you happier!).


Learning

Everyone can be a teacher. Growing up, my mom always said this quote in Mandarin about how you should see everyone as a teacher. Even someone younger or seemingly less experienced or more junior can teach you something.


In VC, you can have over 15 calls in a day, which can quickly get quite tiring. Instead of seeing these calls as chores to work through, see each conversation as a new learning opportunity. Regardless of the ultimate outcome, you can learn about new problem spaces and solutions from founders; you can learn about market opportunities and investment philosophies from other investors; you can learn about company building obstacles from portfolio startups.

In the content world, there is a misconception that you can only learn from people who have “truly made it” (exited a billion+ dollar company, for example) but in reality, you can frequently learn much more from people who are more adjacent to you in your career trajectory. Seed stage founders, for example, can learn much more about what they need to do in the next 9–12 months from Series A founders than from the Bill Gates of the world. In VC, I have found that sharing this type of content, insight, and intros can frequently be even more valuable than connections to incredibly senior people.


Have an information rich diet. When you are doing the dishes, folding laundry, or taking a walk, listen to a podcast. When you are waiting in line at the grocery story, read a newsletter. When you have a few free hours on the weekend, read a book. When you have a few minutes to scroll through social media, pull up LinkedIn or Product Hunt and learn about what other people are working on. Approach everyday with voracious curiosity, and you will always learn something new.


Take control over your own learning. Just like you should not be restricted by the network you enter VC with, you should similarly not be restricted by the knowledge base you start out with. After dozens of calls and readings in a particular space be it insurtech or remote work tools or telehealth, you can quickly become knowledgeable in a particular area on the job even after starting from 0.


Life

Don’t worry about disappointing other people. When I quit my investment banking job, I thought I would disappoint my parents, my mentors, and my friends. All these people had been so generous with their time and advice and support in helping me get to investment banking, and I was afraid to let them down. Then again, in leaving VC, I shocked many people who wanted to know why I would leave such a privileged position and an industry that was so difficult to break into. People felt that I was ostensibly doing well in the industry and were so surprised that I would throw it all away. Even in moving to the operating world and deciding between different job options, many people gave me advice that ended up not being in line with my ultimate choice. I was again worried I would disappoint these people. But I realized over time that there is no concept of “disappointing people.” Sure, people may not agree with your decision and may have recommended a different path for you but ultimately only you have perfect information on your life and ultimately only you live with your decisions. We are all just supporting characters in everyone else’s life story. Don’t worry about what other people think about you because they simply don’t think about you that much.


Do not be overly shaped by your circumstances. In a small team (as most VC funds are), you can learn a lot from your team members but also unintentionally become restricted by what they know and do. If you work with investors who are super sharp at analyzing financial metrics, you can certainly improve greatly in this dimension but also subconsciously neglect analysis on the qualitative side around product and strategy, for example. If you work with very extroverted investors, you can learn tons about network building but unintentionally neglect to develop on the introspective, first principles thinking front. Learn from your team and let their strengths become yours but do not adopt their weaknesses.


Have a clearly articulated priority stack. As a VC, you are constantly pulled in different directions with numerous people asking for your time. While it is important to be responsive to everyone, you only have 24 hours in a day (and maybe at most 12 hours for synchronous meetings). Have a clear micro level priority stack to better guide what you say yes and no to and avoid fear of missing out when you do say no to engagements or opportunities.


At the macro level, you should also have a priority stack. What are you ultimately optimizing for? Is it money or freedom or happiness or family or something else? Listen to your inner voice and your heart. It is easy to be so heads down and focused on executing the day to day that you forget the forest for the trees. Life is so much more than work. Figure out and hold onto what life means for you. Help others but never sacrifice yourself to no end.


A huge, huge thanks to every investor and founder who has taught me so much along the way, including much of the advice shared here, and to all those who inspired me everyday. And a special thank you to my incredible team at Soma Capital for a wonderful year.


About the Author


Harvard Grad | Head of Content @ Elpha (YC S19) & Harvard in Tech | Marketing @ ZAGENO | https://linktr.ee/jessicali


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