Q&A with Vinay Iyengar (Investor at Two Sigma Ventures)

(Est. read time: 6 min). The Takeoff is back with a new Q&A on breaking into venture capital, finding a job at a startup, and more.

Hey everyone,

Michael here 👋. We’re changing it up a bit today. Instead of bringing you a new What We’ve Been Following newsletter, we have an awesome Q&A with Vinay Iyengar. This Q&A comes on the back of Vinay’s recent blog post The Ultimate Guide to Finding a Startup Job, which you should check out if you haven’t already.

Vinay is an Investor at Two Sigma Ventures, where he focuses on enterprise software, ML, marketplaces, and infrastructure. Prior to TSV, Vinay was an Investor at Bessemer. During his time at Bessemer, he worked on investments in Astorian, Coder, Shopmonkey, and PagerDuty, among others. He also co-led Bessemer’s D&I committee.

In this Q&A, Vinay talks about four main things:

  1. His background.

  2. Breaking into venture capital out of school.

  3. What spaces he’s most interested in.

  4. His The Ultimate Guide to Finding a Startup Job blog post.

    While a bulk of the Q&A discusses Vinay’s recent blog post The Ultimate Guide to Finding a Startup Job, I highly recommend heading over to Vinay’s blog (The Vin Diagram) and checking out the post for yourself if you may be interested in joining a startup after graduating / getting an internship at one.

That’s all from me. I hope you enjoy today’s Edition of The Takeoff! If you dig it, consider sharing the post with your friends.


— Michael

Michael: You are currently an Investor at Two Sigma Ventures. Can you discuss a bit about your background and how you actually came to be a venture capitalist?

Vinay: I went to Harvard intending to become an academic. I had spent time doing math and computer science research in high school and thought I would continue down that path. As a freshman, I stumbled upon entrepreneurship rather accidentally and started a SaaS company with one of my best friends. Though it was a total failure, I caught the “entrepreneurship bug” - I realized I wanted to spend my time helping entrepreneurs to build the future and use technology to have impact at scale. I was very lucky to meet some venture capitalists during my own entrepreneurial journey and to eventually land a gig at Bessemer right out of school.

Michael: Let’s dive into Two Sigma Ventures a bit. You spent a few years at Bessemer and then made the jump over to Two Sigma Ventures. What attracted you most to TSV?

Vinay: I’m a big believer that the next generation of great venture capital firms will have to be built differently. I think Two Sigma Ventures is doing this in a few distinct ways. We are not a corporate VC and are entirely independent from our hedge fund parent organization, but we leverage their network and expertise to help our portfolio companies and go well above and beyond what most traditional venture capital firms offer in terms of value-added services. Second, we have a strong thesis around data-driven companies and spend our time building deep technical and sector expertise. Third, we aim to use more data in our actual sourcing and selection process. We are one of the very rare venture firms that actually has full-time software engineers on our team! These unique aspects of the TSV platform plus the wonderful people on the team made my decision easy.

Michael: What type of investments do you focus on? Do you have any industries, sectors, or stages you focus on in particular?

Vinay: Stage-wise, we are focused on leading traditional early-stage investments (Seed through Series B checks primarily in the $2-10m range). Sector-wise, I am a generalist at a high level but gravitate towards more technical products and teams. This can mean a variety of things, but typically this means b2b software companies and often those that sell to a developer audience (dev tools, open-source software, cloud/data infrastructure). Above all, I aim to work with outstanding teams who are passionate about solving a big problem they have empathy with. 

Michael: You recently wrote a post on your blog titled The Ultimate Guide to Finding a Startup Job. In it, you discuss a lot of things related to getting a job at a startup as a recent grad or young professional:

  • The importance of knowing what you are looking for.

  • How to find an interesting company.

  • Knowing what questions to ask.

  • How to get your foot in the door.

  • Figuring out compensation (cash v. equity).

You also provide a list of ~15 potential companies to join. A lot about what we aim to do with The Takeoff is help students with a lot of these same questions, so I want to dive deeper into a few of these topics.

I’ve developed the perspective that peoples’ first few years out of school should be focused on learning — work with smart people on an important mission and learn as much as possible. I know everyone has different goals, ambitions, and motives at different stages in their career. What advice do you have for current students to help them figure out what they want to focus on in their first few years out of school?

Vinay: I absolutely agree. Learning should be the #1 priority, whether for new grads or even slightly older folks like myself! Specifically, the big goal for new grads should be to learn what they’re passionate about — what doesn’t feel like “work”? What problems in the world do they have a burning desire to solve? All too often, I see talented young people go into banking/consulting because “everyone is doing it.” But, these jobs ultimately don’t get them any closer to answering this question. I’m a big believer that the startup career path can be much more fulfilling! One of my favorite quotes is from Steve Jobs (and I’m probably paraphrasing here a bit): “The only way to do great work is to love what you do. If you haven't found it yet, keep looking. Don't settle.”

Michael: Finding good companies to work at is hard. But, it is absolutely crucial if you want to learn a lot and progress your career as much as possible. If I am a student at a school that doesn’t have great ties to startups, a school outside of SF, Boston, LA, NYC, or Austin, how should I go about finding the best startups to get involved with?

Vinay: The beauty of the Internet today is that most companies and founders are easily accessible to anyone with just one email or Twitter DM. I would encourage students to be really persistent and shameless in their cold outreach to founders/VCs/mentors and other people they think are plugged into the startup ecosystem. Don’t let your school or geography influence what companies and people you can access.

Michael: So, say I’ve found a few companies that I think may good a good fit. How do I know what questions to ask them? And, how do I know if these startups are actually good places to start my career?

Vinay: The guide walks through a lot of the detailed questions to ask and heuristics for evaluating how well a startup is performing. The most important thing, especially early in your career, is people. I love Warren Buffet’s framework for evaluating partners: look for people who are high energy, high intellect and above all, high integrity. You want peers and mentors who are invested in your success, push you, inspire you and give you a solid foundation for the rest of your career.

Michael: How can students start building their networks while still in school?

Vinay: Networking is an odd concept. It can feel artificial, and without having anything to provide in return, can often feel like you’re wasting someone’s time. Luckily, while you’re a student is one of the rare times when you can reach out to people freely for advice without needing to provide anything in return. Your lens for “networking” while in school should be very focused on learning and finding great mentors. And once again, I would not underestimate the power of a cold email. Finally, something as simple as sending a biannual “check-in” email to a curated list of mentors/contacts is a great way to keep people posted on what you’re up to.

Michael: Are there any resources that you would point students towards to learn more about startups, technology, venture capital, etc.?

Vinay: I think Twitter is a great place to start. I’ve found that a well-curated Twitter feed is an awesome way to stay up-to-date on the latest in startups/tech/VC. Newsletters like ProRata and StrictlyVC also provide a great daily briefing. Finally, there are some long-form publications like Stratechery, The Newcomer, and The Generalist which have fantastic, in-depth pieces on trends and companies.

Leave a comment

Thanks for reading our Q&A with Vinay. You can find him on Twitter @VinIyengar. And, be sure to check out his recent blog post The Ultimate Guide to Finding a Startup Job.

Moderated by Michael Spiro (Founder at The Takeoff. Senior at Washington University in St. LouisJMI EquityEqual VenturesGround Up VenturesIntello).

I’m on Twitter @mspiro3 👋 (direct any thoughts / comments / questions to my DMs).

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