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Two Investors’ Top Advice For Breaking Into Venture Capital

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Venture capital is a notoriously difficult industry to break into. It has a long history of being a small, insular industry where open roles are rarely posted publicly and you’re only as good as your network. This means there are very few jobs and they’re usually filled by a warm referral.

So we assembled a panel of investors to share their tips for breaking into venture capital. And, they have good news: over the past few years the industry’s gates have significantly lowered, allowing young and fresh talent unprecedented access.

We were joined by Nicole DeTommaso, a first-generation college graduate that spent time as an investment banker before landing a job as an investor at Harlem Capital, and Rak Garg, who led product at Atlassian before joining Bain Capital Ventures as an investor. Here’s their best advice for breaking into one of the most elusive industries.

Why is venture capital such a ‘gatekept’ industry?

Nicole: I think it's so gatekept because everything about the industry is based on your network. Because of that, many people who don't have family or friend connections in the space don't get access to the information the way they should. Up until recently, and still now it's a problem, job postings don't get made public. Instead, they go through networks and make venture even more insular. So I think it's the nature of the industry being so network-driven that makes it so gatekept.

Rak: I thought investing was what you did after you sold a few companies and ‘made it’ – and I most certainly have not ‘made it.’ I think the industry has gone through a really big transformation in the last decade and a lot of firms are now able and willing to mentor young people and bring them into the fold. I think it's changing, but historically the barrier to entry was just so, so high.

Knowing that your network remains so important to breaking into VC, how can someone go about building their network?

Nicole: If you’re not already full-time in the industry, it can be really intimidating to reach out to full-time people in the industry. Also, due to the nature of the business, people who are full-time tend to have blocked calendars and so they have less availability for you. My suggestion to anybody who's trying to build a network in VC is to reach out to VC interns because they're usually students or people that are also trying to build their network so, honestly, they are probably happy to take a call.

When I was an intern at Harlem Capital, I wanted to talk to people who wanted to get into the industry. Then from there, since they’re interns, they probably have full-time contacts that they can refer you to and so on. I think that's a really low-stakes way to start building your network in the industry.

Whether someone is applying straight out of college or has some non-VC professional experience, how do you pitch yourself as a value-add to a firm?

Rak: I think there are two main things: insights and deal flow. On the insights front, the question is: Are you really deep in a space that the firm wants to be deep in but isn’t deep in today? An example of this: I came from Atlassian and used to lead a security product there. Bain Capital Ventures obviously have general partners who are very deep in security, but they didn't really have a deep focus on identity and privacy prior. That was my angle. I talked about how I thought new privacy regulations would enable this wave of identity companies that would get started and become a whole new market for investors. You have to show this differentiated insight that the firm really needs.

On the deal flow front, it's about showing that you're in the right circles and “in the mix.” Do you know about companies that are getting funded? Do you know about new tools that people are using in your specific vertical? A lot of my feedback is biased by the fact that I do software infrastructure, but knowing a bunch of engineers that could tell me about new tools they were using at work was really helpful because that's what we VCs care about. So it's insights and deal flow to show your value-add.

How can an applicant stand out and show they have the ability to truly think like an investor?

Nicole: I'm a big fan of going slightly above and beyond to make it tangible, like sending a one-pager analyzing a startup or talking about their portfolio companies or the networks that you can tap into. It goes a long way for them to see that on paper and you will be in the top 5% of applicants who do that because most people don't.

Honestly, it's also a really good process for you to do going into these interviews to think through: What is the value that I'm trying to pitch? What is my story? Putting it on paper makes you think about it more critically and why it is important for this firm in particular. Where's the gap that they have and how can I fill it with my experience? It's interview prep in that way so, if you're gonna prepare for the interview, you might as well just send it, right?

Once someone lands an interview, how should they prepare?

Rak: When I interview people, it's really obvious who is sort of memorizing TechCrunch headlines from the last week. We're looking for people who are students of technology. You want to show that you've been tracking the space, the venture industry or technology broadly for a while. It's the most shallow conversation when you interview someone and the only companies they can mention are the ones that came out on TechCrunch 30 minutes before the interview.

Nicole: There are different categories of interview questions. There are behavioral like, “What is your experience and how is it relevant?” There are market questions like, “What trends are you following in the space? What are you seeing in terms of valuations?” Then there's firm-specific questions like, “What portfolio companies do you like? What wouldn't you have invested in?” Then there's the more technical side of things if you get further along where they'll ask you cap table math, etc. Generally, those seem to be the four buckets that get hit and it’s what I prepared before every interview.

One edge that you can also have is to look at the firm’s social media. You can learn so much about the firm through their social media that might not be on their website. One trick that I like to do all the time is mention something about a blog post that they posted or a tweet. VCs are posting it so that people see it and, if you are diligent enough to be on their platforms, mention it in a way in the interview. Most people don't do that and it shows you're following the firm.

Do you need a full-fledged investing thesis in order to land a job?

Rak: When I was interviewing I asked a general partner what their thesis was and he sad, “Invest in great companies. What else could be the thesis?” I think it's really prescient, honestly, because I don't think you need a unique thesis in as much as you need a perspective on the kinds of companies you like. Those are two different things. I wouldn't say I have a unique thesis, but there are certain kinds of founders who I get really hyped about and there's certain kinds of businesses I get really excited to see.

Even when I was at Atlassian, there were other companies I saw and knew I really did not want to go work for. And there were companies that I would have loved to go work for. That's kind of a thesis, like you're investing your time as an operator. So I wouldn't focus too much on determining your differentiated way to evaluate companies. I would just think about what you do and do not like, then why you like the things you like. That's your thesis.

What’s your best advice for structuring a VC job search?

Nicole: Be somewhat targeted in your search for VC firms. I think when I was going through it, I really wanted to get out of investment banking and so I was sort of throwing spaghetti at the wall. One week I was interviewing for a growth-stage healthcare firm, and then the next I was interviewing for an early-stage consumer fund. I think when you try to context switch that much, your interview prep gets really lengthy. Whereas if you were targeted, you can be more thoughtful about your interview prep.

Be thoughtful about your interview process and don’t just apply for every role because it's open, which I think can be obviously enticing given the way that venture roles come up. But I think that's something that really hurt me in my interview process. I was getting through the initial rounds and then when it got to the more in-depth stage, I just didn't have the capacity to study for the interviews the way I would've liked and so I wasn't getting through. Create a list of firms – don't make it too niche, but don't go too broad – and it should help you in your search a bit.

Rak: It's really not worth doing venture if you don't vibe with the firm and with the companies that they invest in. It's really not worth it. I would suggest that you stay true to yourself and what you like and what you don't like. Use that as a filter for the kinds of firms that you would want to work for.

Venture firms are partnerships – they're not really companies. Imagine yourself joining this partnership and think about the people that you meet: Do you want them to be your partners? Do you want to be working with them day in, day out? They're the ones who are going to help you make really hard decisions, whether doubling down on a company that's going super well or pulling out on a company that’s not. There are really hard discussions that you have every day in this job and it's not worth it if you don't vibe with the firm, really honestly. And, you know, stay true to yourself.

This interview has been edited and condensed for clarity.

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