How I Got a Job in Venture Capital

It’s Labor Day Weekend, the summer is over and I’m spending the weekend visiting my parents in Central Connecticut. After a whirlwind August (South Africa, SF and NYC), I finally have some time to take a step back and reflect on the past few months. With fall around the corner, I wanted to give blogging a shot and share my story of how I ended up working in venture capital in NYC. Hopefully some of you will find it helpful. So here it goes.

First a little background on me. I was born in a small town in Southwestern Poland and came to the States in July of 2000, right in the middle of the first Dot-Com bust, as a ten year old. (I’m planning a separate post on how being an immigrant and an avid backpacker shapes how I source and evaluate deals as a VC). I grew up in Central Connecticut around immigrants and factories and it wasn’t until college that I heard about entrepreneurship, startups or the dark art of venture capital.

I studied Finance and International Relations with a focus on Eastern Europe and East Asian Security at Boston College, and like many, had no idea what I wanted to do. It was during my freshman year at BC that I got my first exposure to startups. BC is not a place generally known for entrepreneurship; it has always been focused on the Big 4 and finance. Luckily for me, through the hard work of a few students and faculty, that began to change just as I arrived on campus. I first became involved with the Boston College Venture Competition with some silly business idea. Our idea didn’t go anywhere, but later in my freshman year, I became part of the executive committee for the remainder of my time at BC. It was a life altering experience — I got to know the Boston startup ecosystem through our events, competitions and trips. I still remember taking P.J. McNealy’s class my freshman year and learning about new media and digital business models and having unreal guest speakers every week (thanks P.J.!). I even landed an internship with WePay in Palo Alto in the summer of 2011 when Facebook was still private and loved it (thanks Bill, Rich & Tyler!). Even though I didn’t join a startup right after college, I knew that I would eventually find a way back.

As I was wrapping up my last year at BC, I wasn’t quite sure what I wanted to do, but I knew that a) I wanted to live in NYC and b) pay down my student loans so that I had more bandwidth to take risks and do what I was passionate about (whatever that would turn out to be). I spent two years working in growth focused technology investment banking in NYC. I didn’t like it, but I learned a lot. It forced me to think about what I enjoyed doing and what I would like to do — and that turned out to be working with tech startups. I knew that I wouldn’t stay for a third year, so I started looking for ways to break into VC. I probably read every book, blog post and tweets about it, in addition to talking to headhunters etc.

So how did I end up at Rubicon? A few months before I left my banking job, I started to cold email a bunch of VCs in New York City to get coffee with them, ask for advice and start networking. Most of my (repeated) emails went unanswered, but a couple of GPs did get back to me. One of them was Joshua Siegel at Rubicon Venture Capital and Mike, a GP of a seed focused fund in NYC. Mike was incredibly helpful in helping me narrow down my interests and was indispensable in helping me to prep for interviews.

On one cold, mid-January morning in 2015, I met Joshua for breakfast at Hudson Cafe, and little did I know, that months later, that breakfast would lead to where I am today — a VC Associate in NYC. I remember getting ready for that breakfast meeting — learning about Rubicon, its focus, the team’s backgrounds and preparing a few ideas to discuss. After the meeting, I tried to stay in touch to be helpful and top of mind, but not be overly annoying. If I came across an interesting company, I would send it Joshua’s way along with a quick explanation of why I thought it was compelling (looking back at them, they weren’t). But it paid off. Later that spring, Rubicon was hosting an event (we host about 6 events annually between NYC, SF and London — check them out here) and Joshua needed help handing out name tags, setting up chairs, etc. I was more than happy to help out. It wasn’t glamorous work, but VC is about hustling — to find deals, fundraise and help your portfolio companies succeed. This turned out to be a great opportunity — I was able to have a follow-up meeting with Joshua which resulted in me doing some part-time research work for Rubicon in the following weeks.

As my time in banking was coming to an end, I decided to turn down a couple of job offers and take some time off. I wasn’t excited about any of the opportunities that I had in front of me, but I knew that I wanted to travel. In the back of my mind, I was hoping to eventually join Rubicon when I came back from my trip, but that was never guaranteed. My trip evolved into a five month backpacking trek spanning 22 countries on the fringes of Europe and Asia (separate post to follow). While traveling, I offered to meet with local startups on Rubicon’s behalf. And I did. I ended up meeting about 20 startups while I was in France and Spain, fitting meetings in in-between sightseeing and dinner with friends. After I joined Rubicon, we almost invested in one of the startups that I met that August in Paris. It was during that part of the trip that I realized that VC is what I wanted to do and would somehow find a way to break in.

Once I came back to the States, it took a few days to get accustomed to being back in New York. But reality hits quickly and I had to start looking for a job. Living in NYC is not cheap. I remember coming into Rubicon’s offices to meet with Joshua for a few minutes to catch up in mid-December 2015. We had a great talk and since that Monday, I haven’t left. It wasn’t always easy. At that time, Rubicon was in some great deals, but wasn’t big enough to bring me on as a full-time resource. After literally walking hundreds of miles, I knew that I wanted to work in venture and I was committed to it. So for the next three months, I volunteered as a full-time Associate learning the business and proving myself to the team. I did everything I could to show Andrew and Joshua that when they were ready to bring someone on, they wouldn’t have to look far. Looking back at it, I would 100% do it again.

As every VC would say, there is no single path into VC. I talked and walked my way into the job. I got to know the team early, before they had a need for an associate. I found ways to stay in touch and be helpful, without being overbearing. And I tried to deliver value, even before I was part of the team. I found that this formula is also the best way to source new investments. In the end, it all worked out for both sides.

The past nine months at Rubicon have been incredible. The amount of amazing people I have met and how much I have learned, has been mind blowing. The ability to meet so many talented entrepreneurs and support our portfolio CEOs is something that I look forward to everyday. I’m extremely grateful to Andrew and Joshua for giving me a shot nine months ago, and I’m looking forward to many more years working with them as we continue to build Rubicon.


  • The journey to a VC job is different for everyone — make your own, don’t follow others’
  • Be passionate about the field — read, talk, listen. Demonstrate that you have a track record of interest
  • Don’t wait — get out there to meet people and start building your own network and deal flow
  • Be value-add to the VCs you meet — interesting ideas, introductions and/or deals will keep you top of mind
  • Put your money where your mouth is — don’t be afraid to work for free for a VC you have a good relationship with and want the position, even if it’s not immediately available
  • Be different — travel, volunteer, read. Have a unique perspective and spot deals others might not understand
  • Have a positive attitude, it’s not easy to find a job in venture capital

What I’m interested in and how to contact me

  • Rubicon is a generalist fund and we review all sorts of deals at the Late Seed and Series A/B stages
  • I am currently interested in FIRE’EM — Fintech, Insurance Tech, Real Estate Tech, eSports, Enterprise SaaS and Machine Learning
  • You can find me on Twitter at @matkaliski and email me at mat at rubicon dot vc and checkout our page out at

About Rubicon Venture Capital

Rubicon Venture Capital is an early stage VC fund with offices in San Francisco and New York City focused on backing consumer and enterprise technology companies in the internet, software and connected hardware verticals at Late Seed, Series A and B stages. Rubicon raises capital from corporates, individual high net worth angel investors, family offices and institutional LPs creating a powerful network ready to help and go to bat for our startup portfolio. We enable our LPs to co-invest alongside the fund on a deal-by-deal basis via innovative sidecar funds right up to IPO or M&A exit.

Early stage VC @ Rubicon Venture Capital, NYC

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