It's not a problem unique to the startup landscape, but it is a problem many people face: If all startups want workers with startup experience, how can you ever get your foot in the door if you haven't worked at a startup before? There are many ways to score the startup job of your dream without depending solely on unpaid internships (although that may be the exact route you have to go). First, identify your passions. Kind of like working for a non-profit, if you're passionate about a startup's mission, that excitement will shine through--and for the right fit, that's going to be incredibly important.
Rather than knowing you want to work for a startup, know that you want to work for a startup in a specific industry or to have a specific job role. I am reminded of the story of a friend who excelled at sales and business development for a large Silicon Valley company, but wanted to leave after more than 10 years there. He saw the startup he wanted to work for, hounded the founder (a very well-known one with little time), and eventually got a meeting with him. Right on the spot, he convinced the founder to give him an unpaid job, with the idea that he could earn a paid job if he met certain revenue goals. He met those goals in less than a month and earned himself the job. The lesson here is simple. Everyone on board needs determination and commitment to make sure a startup succeeds. If you showcase that you have passion for the startup as well as confidence in your abilities, you'll be seen as an instant ally. Here are some of the reasons why my friend succeeded at doing that.
Match Yourself to the Company
In an era where you can find anything about a business online, particularly startups, make part of your research figuring out the company's success strategy. Get to know the leaders, the mission and use any other tactics you can. As a matter of fact, you should be researching multiple companies on an ongoing basis. The search for your next job should be a part time job in itself. Your goal isn't to parrot back what you think the recruiters want to hear during interviews. Ask yourself if you naturally align with what the startups are doing. To some degree you will know this in your gut as well as your mind, because at this stage in your career you most likely know what you enjoy doing and what you are passionate about.
If you do identify with their mission, now is the time to position yourself well. It's your job to clearly showcase what you can do for the company and why you're the best fit. If you can, figure out what the "real" company culture is before the interview--laid-back, business casual, geeky, and the like. If you mesh with that part of the culture, you can be more yourself and show up in those new sneakers if you want. If it's totally out of your comfort zone, you may decide the culture fit just isn't there.
Be a Good "Guest"
Don't be afraid to show excitement about the job and the startup itself. It's the job of the startup to make an applicant feel welcome, but there's a good chance the person doing the interviewing is just as nervous as you. At a couple of the startups I've worked at I was asked to interview new hires. It was a bit nerve-wracking because I had never done that before. To some extent this gave the potential new hire a "warm-up" before one of the founders came along and did their own interview.
So one thing is clear--startups aren't known for their comprehensive HR departments. However, if you do your homework and know the basics of the company, you should feel at ease. This is a two-way interview, and everyone is just trying to find the best symbiotic relationship.
One way to show interest is by asking thoughtful questions that show you know the business and truly want to figure out if it's a match. Be proactive, adopt a good attitude and don't be afraid to show your creative side. Startups move quickly, and changes are common. If you show you can roll with the punches with a smile, you'll have an instant advantage over a candidate who is less adaptable, despite having startup experience.