How to Break into the Startup Community

A few nights ago I found myself trapped inside a tiny office of a recently launched startup, surrounded by some of the brightest minds in the Boston startup community. As I sat there listening to them joke about who does the most work at their respective companies, I couldn’t help but think to myself, “How the hell did I get here?” A couple months ago I was studying political science, admiring the startup scene from my Twitter feed.

Getting involved with the startups in your city can often be an awkward and intimidating process, but it’s not impossible! If you’re hungry for a job at a startup but don’t know how to make it happen, here are a few pieces of advice to help you break into the startup community:

1.  Do your homework – It’s important to build a solid foundation before you start reaching out to the startups you are interested in working with. Who are the major players? What trends are emerging? How did X company become so successful so quickly? A good place to start is Harvard Business School professor Tom Eisenmann’s compilation of advice for entrepreneurs. If you live in the Boston area, Rob Go’s “Hitchhiker’s Guide to the Boston Tech Community” is an invaluable resource that lists everything from influencers you need to follow on Twitter, to local online resources and newsletters.

2.  Pick your mark – Lets face it, if you’re not a superstar programmer, the odds of you working for a top tier startup are slim. Justin Kan, co-founder of and TwitchTV, suggests seeking out a startup with a team of 8-10 people. This greatly increases your chances of getting in on the ground floor. “These companies are unproven and won’t likely have throngs of experienced people banging down the doors,” he notes. You will likely be ranked higher in the candidate pool by matching yourself up with a company where you’ll be taking on as much of a risk as they will be taking on you.

3.  Attend local eventsMeetups, Tweetups, open houses, and launch parties are all great ways to meet a lot of people with similar interests. Not every person you meet will be a co-founder or a VC, and your first few events will most likely be awkward, but don’t give up! You will gain a strong understanding of the community and meet a lot of people willing to be a part of your professional network. Check out StartupDigest to see some of the events in your area.

4.  Send cold emails – I’m a big fan of sending cold emails to startups and entrepreneurs I find interesting (it’s how I weaseled my way into Smarterer); however, there are a couple of rules that need to be followed. Ben Carcio, Founder and CEO of Promoboxx, says the golden rule of cold emails is, “Don’t monetize the relationship before you build it”. He suggests skipping the pitch and offering to buy someone in the company a cup of coffee in exchange for twenty minutes of their time.

You may have to send a ton of emails before you hear back from someone willing to take you up on your offer. Don’t get discouraged! There are plenty influential people within the startup community following up on emails and coffee conversations. Janet Aronica, Head of Marketing at Shareaholic, has a fantastic blog post about why she responds to college students’ emails, and why it’s important. She writes, “All the coffees and email exchanges I had with other professionals provided me with motivation, direction, momentum and confidence. Two years later, how could I not pay it forward?”  Setting up these meetings is a great way to build relationships with companies in your city and to keep your name circulating within the startup community.

5.  Highlight your skills – Are you a Social Media maven or Google AdWords wiz? Being well rounded and “willing to do anything” are great qualities to have, but they are expected out of everyone interesting in working for a startup. It’s important to be upfront and highlight your core skill sets. One of the ways you can accomplish this is to add your Smarterer test scores to your Linkedin profile, page, and email signature.

Who wants to grab a cup of coffee?

Do you have any tips for breaking into the startup community in your city?  Leave them in the comments below!