9 Essential Lessons That Helped Me Break Into VC

Tactical advice for those hoping to become early stage investors

Over the last two years, I’ve fallen super deep down the venture capital rabbit hole. It’s been an incredible journey — from funding student entrepreneurs at First Round’s Dorm Room Fund to exploring novel investment theses at Bessemer Venture Partners to joining a network anchored by Zuck + Gates + Bezos at newly launched firm Village Global. While in my heart of hearts I’m an operator and I miss scaling companies, I’ve found that being a VC is the most fulfilling job I’ve ever had. I spend almost all of my time meeting the smartest hustlers on the planet, learning about their ideas, and — for some — becoming their first believer offering them their first check.

It’s been a wild and unpredictable path to break into venture, and I’m hoping to share the lessons I’ve learned along the way that have helped me get here. There’s already a ton of great content written about this subject. For starters — CRV’s Justine and Olivia Moore wrote a very thorough piece on how to find a VC internship and BoxGroup’s Adina Davis makes great points about the MBA path into VC. I’m by no means an expert, but I’m happy to throw in my (very freshly minted) two cents.

I’m most closely aligned with Founder Fund’s Delian Asparouhov’s thesis that you should optimize for building reputation and trust with venture capitalists if you want to break into VC. I think you do this by signaling to founders / investors how you can be most helpful to them and then proving it. One thing that resonates with a lot of folks who have made this journey is that you have to do the job in order to get the job. Successfully executing this is not a short term exercise — it takes time and requires patience. Building rigor around your investment approach in a way that repeatably helps you identify great companies is an entirely different animal best left for a separate post, so I’ll just focus this essay on how to get your foot in the door. To be upfront, I have no silver bullet answers, but the following is a collection of advice I’ve received over the years that I hope will help you even the odds.

1. Design and refine an effective information diet.

Before you do anything, I believe it’s important to regularly consume content and surround yourself with people that sharpen your point of view on subjects related to entrepreneurship and venture capital. One super helpful article for this is Jason Heltzer’s list of VC resources — I suggest subscribing to a few newsletters / podcasts there (in addition, I think Stratechery, Accelerated, and Hacker News provide good commentary). However, for me, the most important part of my week was riffing on tech topics with Dorm Room Fund’s unparalleled community of high caliber founders, investors, and operators. I was never the smartest person in the room, I frequently encountered pushback on my opinions, and debates were intense —as a result, I learned a ton. Find your own tribe that will make you better every single day.

2. Understand that there are three core jobs in venture — finding, funding, and fixing startups.

Kleiner Perkins’ Ted Schlein passed this lesson down in one of his many visits to Penn as the “3F’s in VC”. Finding startups refers to sourcing solid companies for potential investment — you need to build relationships with founders that allow you to learn about fundraising opportunities before anyone else can. Funding startups refers to conducting due diligence and exercising good judgement on which companies to actually invest in. You need to successfully identify the top companies that matter the most each year and then successfully convince the founders of those companies to work with you. Most partners will look for junior investors that can augment the finding and funding functions, so I’d prioritize becoming world-class at these two first. Fixing startups refers to getting into the trenches with founders to help them build their companies, especially when things go south. Portfolio support is measured pretty subjectively but, at the end of the day, you want founders to feel supported and their businesses to grow. I’m a big fan of this function because it’s something you can easily start doing before you become an investor. Early on in my own VC journey, I started advising the team at Lime on international go-to-market strategy. This helped me earn fixer street cred amongst founders that ultimately made me better at finding and funding. In any case, as it’s been explained to me, only a handful of investors truly master all three Fs.

3. Understand that there are three aspects that firms compete on in venture — speed, price, and product.

First Round’s Phin Barnes first introduced this insight to me by asking a question — why should founders decide to work with you and take your money before anyone else? Speed and price are self-explanatory, venture funds try to discover founders of great companies before anyone else and they offer investment terms that are more favorable than other firms in order to win deals. Venture funds compete on product by offering services that help founders build their companies. First Round focuses here and I believe this gives them a sustainable advantage. Phin even optimizes the meeting experiences he delivers to entrepreneurs! He frames different components of what you deliver to founders as “features” in the product — for instance, individual investors at a fund might offer a phenomenal network (e.g. the legend of Ron Conway) or valuable experience in a certain function (e.g. Sarah Tavel’s learnings from scaling Pinterest). I found that brainstorming new “features” with investors was a natural way to solidify relationships — one subject I frequently discussed with partners was how to leverage software to help founders scale their companies faster. Venture funds frequently think about how to optimize these three points to win over founders, but I think product is where a junior investor can offer the most lift.

4. Know who you are — identify your archetype and superpower.

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:

• Entrepreneurs can say “I have built a company before and can empathize with founders.” (e.g Initialized’s Alexis Ohanian)
• Operators can say “I have scaled companies before and can help founders do the same.” (e.g. Defy’s Brian Rothenberg)
• ‘Mafia’ alumni can say “I was on the founding team at X unicorn and know all the good future founders there.” (e.g. ex-Uber and ex-Airbnb)
• Analysts can say “I have an insightful investment thesis and unique point of view on Y promising vertical.” (e.g. Greylock’s Sarah Guo; most ex-consultants and ex-bankers start here)

You should then determine what your superpower is — this is the unique value that you offer a venture fund. A16z’s Andrew Chen shared that having a superpower is one of three key hiring criteria at Andreessen Horowitz (for reference, the other two are “magnetic attraction to founders” and “culture fit”). As he describes, you can’t just be AN expert in a particular subject, you should be THE expert. In Andrew’s case, I would argue he’s THE expert on growth that every early stage founder should have a quick chat with (he led driver growth at Uber, co-founded the growth hacking bootcamp Reforge, and has been writing about the subject for a decade). For me, I leaned into my work with student entrepreneurs (“I have a point of view on who the strongest founders / engineers / designers are at the top schools in America”) to score my first internship in venture. You need to identify and clearly articulate your own superpower.

5. Clearly and concisely communicate your narrative.

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.

Let’s take the example of my friend Jerry, a rockstar former data scientist at Google / Youtube who had one of the best stories of anyone I met in grad school. When he spoke with venture funds, Jerry pitched himself as a super technical investor who could a) source great founders by speaking the language of engineers, b) accurately diligence complex product risk, and c) have informed points of view on deep tech. He regularly wrote content that showed just how smart he was on subjects such as voice AI and digital avatars. Jerry made a strong case — he ended up doing stints at Baidu’s corporate venture fund and Lux Capital, both focused on deep tech investing. You need to figure out your own story just like Jerry did.

6. Do your homework. Learn two pieces of information about a venture fund — who is the best person for you to speak with and what do they need.

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.

7. Earn founder goodwill—build close relationships with entrepreneurs.

You should prioritize meeting more founders than investors. Immerse yourself in founder communities — Floodgate’s Mike Maples suggests covering both horizontal networks (specific groups, e.g. Y Combinator) and vertical networks (specific industries, e.g. crypto). Once you meet founders, you can earn founder goodwill in a number of ways. Early on, I hosted a number of office hours for founders to give personalized feedback on their pitch deck and fundraising strategy. You can also earn founder goodwill by connecting them to new hires or customers, taking on side projects, or just being a good cheerleader. Don’t be afraid to send a cold email — if you think you can be helpful to a founder, give it a shot. Host your own happy hours and dinners that bring founders together. Build close relationships with founders and get on a texting basis. As Lightspeed’s Alexander Taussig says, the best warm intros to investors are from founders of their portfolio companies. Moreover, founders know who the other great founders are — ask them to introduce you to their peers! A good word from a founder friend goes a long way.

8. Earn investor gratitude — build a track record of helpfulness amongst VCs.

Over time, you need to show that you can consistently and reliably add value to investors. Connect promising founders to investors who would find their startups interesting (quality matters more than quantity — as a rule of thumb, Felicis Ventures’ Aydin Senkut once shared with me that at least half your referrals should be going to a first meeting). Educate investors on a novel investment thesis in an actionable way. Double down on your superpower — you want to be the first person who comes to mind for an investor when they see a company related to your interests. Successfully delivering on a combination of these will not go unnoticed.

9. Be proactive — win the support of a sponsoring partner and make them your mentor.

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.

I hope this was helpful and I wish you the best of luck!

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.