9 Essential Lessons That Helped Me Break Into VC

Tactical advice for those hoping to become early stage investors

Once you have an understanding of how venture funds operate and compete, you need to assess how you can actually help them. This requires an intimate understanding and honest accounting of who you are, what you’re good at, and what you’re bad at. Are you a natural networker with access to proprietary dealflow, an analytical thinker strong in diligencing startups, or an experienced operator who can help founders execute? What is the function or industry you understand more than others? What are the “features” that you could add to a venture fund’s “product” offering? What are the areas in which you need mentorship? There are a few archetypes that investors generally gravitate towards. There are certainly more backgrounds that break into venture, but I find these to be the most common:

Once you have a sense of how you can best add value to venture funds, you need to figure out how to quickly pitch your narrative and offer signals that reinforce your story. On a tactical level, be able to explain your story in 30 seconds or less. Create a forwardable email template that captures your story in 3 brief sentences or, better yet, bullet points. Develop content (e.g. blogs, social, podcasts) that aligns with your personal brand. Organize dinners for people who share your interests. Collaborate with founders and connect them to hires / customers / investors that make sense.

You can start by backchanneling with founders and investors familiar with the firm. I’d recommend chatting with the investor who most closely aligns with your background and set of interests. Since I started pitching myself as an ex-Square operator who had strong points of view on fintech companies, I typically looked for the investor internally focused on fintech. Understanding what the firm needs is trickier — you need to learn what their gaps are today and tomorrow. Perhaps you learn that an investor has just left the team and now the firm has no one internally focused on a certain vertical (e.g. healthcare) or functional expertise (e.g. hardware product) — this then becomes your moment to convince them that you would be the perfect person to fill the gap. Conversely, if you find that they already have someone who is your exact archetype, chances are they won’t need another person with your same skill set. For some firms, the conclusion might be that you are not a clear fit at the moment — this is perfectly okay. Timing is a huge part of the VC job search. Thank them, keep up a warm relationship, and move on to another fund where the fit is stronger.

More often than not, venture funds will not actively recruit for new investors on their team. Even if they are, they are unlikely to openly advertise that they’re looking. Do not let this deter you! You need to create your own opportunities. Many investors join venture funds by convincing the general partners to create a net new role. One way to do this is to find a sponsoring partner within the firm to advocate on your behalf to the full partnership. These sponsors can also become your mentors. Venture is an apprenticeship business — you should optimize for finding great mentors that will teach you the ropes as well as go to bat for you. Even if it doesn’t work out at their specific firm, these partners can refer you to other firms they’re close with.

Build these relationships slowly and carefully. Don’t be afraid to ask for advice, but do it authentically on subjects you can’t find in a simple Google search. For me, that meant having conversations with mentors on how to gently pass on founders without ruining relationships, how to build portfolio models to determine equity ownership targets, how to evaluate senior associate vs. principal offers, etc. In the end, it is these senior mentors who you want in your corner when you try to break into venture.

If you’d like to get a deeper download of my thoughts on how to best serve founders and be helpful to investors, please reach out! I’d love to pay it forward, especially as it relates to how you can pursue this journey in balance with your existing life commitments (yes you have to hustle, but no, you don’t have to give up sleep). Shoot me a note at sxu@dormroomfund.com. Special thanks to Phin Barnes, Ted Schlein, Aydin Senkut, Andrew Chen, Brian Rothenberg, Justine & Olivia Moore, Adina Davis, Kahini Shah, Brittany Walker, Matthew Mizbani, Bruno Faviero, Adam Eldefrawy, Cindy Berman, Jacob Effron, and Cecilia Chen for your advice and your help in reviewing this article — would not have gotten here without you.

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