January 2014

This article was originally published by Venturebeat

I recently made the switch from start-up to VC, joining BVP after three years as part of the team at Foursquare. Recently, people have been asking me a lot about my experience switching careers and what they should consider when thinking about transitioning into the start-up world. Over the course of these conversations, I’ve boiled it down to four questions that I think are worth asking yourself before taking that leap…

1) What is your definition of “start-up”? – The phrase “start-up” can be misleading, describing businesses in many different stages. Be honest with yourself about the level of risk you’re willing to take – do you want to join a company with traction, financial runway, and one that will give you the opportunity to learn from experienced people, or do you want to join an earlier stage company with more potential upside, but more uncertainty? Your experience will largely be based on the company’s size, financing history, and experience level of the people you will be working for and with. With just 20 colleagues and less than $2M in funding, Foursquare was a different company when I joined than the company that I left three years later with 170 employees and over $100M raised, but it was definitely a “start-up” throughout

2) Why do you want to work there? – If you’re thinking of joining a start-up because it sounds cool or your roommate is doing it – don’t. Make sure you think the company has great leadership and a product or service you can get behind. Sure, the offices will likely be a fun place to spend your days compared to your current corporate digs (and there might even be beer on tap), but things aren’t always easy when dealing with the ups and downs of an organization finding its way. Make sure you are excited to be in that space going forward, as you will likely be gaining expertise that will guide what you do next.

3) Are you ready to define your role? –  The earlier in the company’s life, the more you will have to dictate how you spend your time. Earlier stage start-ups have an endless number of things they could be doing. No matter what your role is, it will be largely up to you to prioritize your time and figure out how to add value. Nobody will be holding your hand or giving you constant feedback, so understand that is what you are signing up for.

4) Have you cut through the hype? – If you want to know how well a company is really doing, what it’s like to work there, and whether or not it’s a good fit for you, then you need to talk to current and former employees. One thing you learn quickly while working at a start-up is that there is often a massive disconnect between perception and reality. So get connected or introduced to people who know the real story.

At Foursquare, I was lucky enough to work with smart, passionate colleagues, experience rapid growth and the associated growing pains first hand, and witness fundamental product and strategic shifts. It was an amazing team to be a part of and the operating experience has served me well in my early days of working with entrepreneurs. If you can get comfortable with the answers to these questions, then go for it.

Foursquare team meeting, June 2010 (photo by Mari Sheibley)