It seems that becoming an entrepreneur is a fad these days. Every week that goes by I meet countless people who profess their desire to work for a startup. They’ve never done it before, but how hard can it be? They’re young, bright, and capable of producing great work. They’ve cut their teeth in the corporate environment, but that no longer provides them with intellectual stimulation, and the grind of the regular workday has become too mundane. What’s not to like about a cool office, great people, and working on the next big thing? It’s just a question of pulling the trigger. But are they really right for the job?
It’s great to see such excitement among my peers, especially in New York, where the tech scene has literally exploded in the last two years. Companies like Foursquare, Gilt, and GroupMe have fueled interest in startups and popularized the belief that technology can change everything. Having this type of attitude is the heart of innovation. It’s the irrational optimism that spurs entrepreneurs into action and allows them to rethink entire categories and ways of connecting with people. But excitement and optimism are only part of the story–they alone won’t make an entrepreneur successful. Nor will pure technical or business talent. At some point, things will get tough and the entrepreneur will have to rely on a different set of qualities to power through a crisis and keep the business moving.
Since the idea of Wanderfly came about two years ago, my co-founders and I have had the opportunity to interview dozens of people before building our team to the current group of 10. All in all, we’ve worked with 40 individuals in some capacity, including interns, contractors, part timers, and regular employees. We’ve seen everything: promising candidates not living up to their expectations, people not showing up to work one day, job offers being accepted only to be turned down a few days later, and candidates who were simply bad for the company. Throughout this experience, we’ve noticed that the successful hires all share a certain set of qualities. Most of these are behavioral in nature; you’ll likely not find them on a resume, and traditional interview questions won’t uncover them, either. Yet their importance cannot be overstated, as oftentimes they’re the difference between a great and poor working relationship.
I’ve condensed the most important traits of successful entrepreneurs into five key themes. For each one, I suggest ways to test prospective candidates to ensure that they have them. Note that I’ve made one assumption: You’re already dealing with someone who’s smart, talented, and, generally speaking, a rock star. These are the qualities that build on their skills and allow them to be a valuable member of the team.
THEY HAVE A HISTORY OF CREATING. Successful entrepreneurs have all started things of their own. That doesn’t necessarily mean they’ve run their own companies. But they’ve done other things to demonstrate their interest in and compatibility with the entrepreneur lifestyle. For example, they may have started the proverbial lemonade stand when they were a child, or helped their parents out with the family business. Others may have moonlighted during their regular jobs with consulting work on the side, or built an app as a hobby. One candidate I spoke with helped a small business grow into a profitable operation right out of school. Why is this so important? These people have an innate appreciation for a lean startup environment and the effort it takes to build something from scratch. They can create something out of nothing, using their own resourcefulness and tools they have at their disposal. And they’re more likely to understand the requirements of working at a startup and to treat the company as their own. Ask your candidates about their past entrepreneurial experiences–it’s a great way to gauge their true interest in the field.
THEY’RE MENTALLY PREPARED FOR A BIG CHANGE. I’ve yet to speak with someone who woke up one day and decided to be an entrepreneur. As with anything, becoming an entrepreneur takes time, and the decision to go out on your own is a big one. Successful entrepreneurs have thought about this moment a lot, they’ve weighed the risks and benefits, and despite some serious downsides, they’re still convinced that it’s the best way to go. When hiring, we like to highlight the realities of the job as much as the benefits to get a read on the candidate’s reaction. Have you considered the implications of a big salary cut? Are you comfortable with the business changing multiple times in the next few months? Can you work without supervision and define your tasks? The keepers are unfazed by all of these questions. The bad ones will be caught off guard and ask for assurances to hedge their bets. I’ve run into this problem a few times–candidates’ excitement turning into doubt late in the interview process, once they’ve understood the true implications of the job. Don’t sympathize with them; you’re only asking them to take a small fraction of the risk the founders incurred to get the company off the ground.
THEY’RE PASSIONATE ABOUT YOUR BUSINESS. The last person you want in your company is someone who isn’t excited about coming to work every morning. Nothing can weigh down your company more than a person who just goes through the motions or is motivated by money alone. Are you truly excited about the problem we’re trying to solve and can’t stop talking about it? Have you used our product extensively and made a list of suggestions to make it better? Have you researched the founders and their backgrounds to get to know the team? People who are passionate about your business will care about these small details. They’ll tell anecdotes of how frustrated they were with life before your product. They’ll use company vernacular and quote things they’ve read about you on your blog or in the news. They’ll have a plan for your business even though you didn’t ask them about it. One candidate we interviewed prepared three pages of ideas for building the business, just for our first meeting. Impressive? Absolutely. Look for those small cues to find a truly passionate person–you don’t want someone who’s just shopping around.
THEY’RE COMFORTABLE DOING ANYTHING. We all know that entrepreneurs wear many hats. I’ve found that the most successful candidates don’t just wear many hats–they’re always open and comfortable doing whatever is requested, no questions asked. My title says Director of Biz Dev, so naturally partnerships are a focus of my work. But if you ask anyone on the team, I’m also Director of Finance, Brenda the HR lady, Chief Carpenter, and Chair of the Social Committee. In a small company, there are too many roles and too few people to fill them, so someone has to step in and get the job done. When hiring, we ask about secondary skills as much as the primary one. What else are you good at? What do you like to do in your free time? What other roles in the company are you interested in? We like people who are well-rounded and can excel in more ways than one, even if it means doing grunt work. As one famous angel investor put it, hire for talent, not skill, and make sure that this talent can be generalized across a wide range of initiatives. This may sometimes mean going far outside your comfort zone, like a non-technical co-founder learning how to code. Has that ever crossed my mind? A few times, actually.
THEY MAKE THINGS HAPPEN. The best entrepreneurs don’t just have great abilities, they make things happen. Or, to borrow a phrase from a fellow entrepreneur, they Get Shit Done. The is probably one of the most important qualities an entrepreneur can have. Why? The rationale is simple: Resources are scarce, time is precious, and raw output is often the only way to judge a young company. Skill, effort, and perfection are irrelevant when they don’t help advance the end goal of building a great product. So ask your candidate about projects they recently completed and how they kept them on track. Give them a homework assignment and see how prompt they are in delivering results. Ask them what it means to have a good day. If they give you excuses, don’t tolerate it. We once worked with someone who spent more time explaining why something couldn’t be done instead of just taking the time to do it. Needless to say, he didn’t stick around for long. Potential in startup employees is worth a lot less than in big companies, because you don’t have the luxury to wait around for its fruition. So hire those who will make an immediate impact, rather than those who may be great one day–you may not be around to see that happen.
I once presented at a meetup for folks who were thinking about joining a startup or looking to start their own company. As we went around the room and introduced ourselves, a few of them announced that they had just quit their day jobs to go out on their own. Each time this happened, the entire room burst out clapping and cheering. I could feel the support of the people around them, and I could see the excitement in their eyes. It’s as if they had just joined an exclusive community of people who were out to change the world.
I remember feeling that same excitement when my co-founders and I were starting Wanderfly. It’s a beautiful thing. But it takes a lot of work to maintain this enthusiasm and translate it into startup success, especially when dealing with the roller coaster of the profession. It takes a lot more commitment than you’d ever expect, and it’s not for everyone.
If you’re looking to join a startup, take the time to ask yourself the difficult questions. Is this something you’re passionate about? Have you thought about it for a long time? Are you ready to make sacrifices and will you do whatever it takes? Can you produce an extraordinary amount of (quality) work as you never have in your entire life? If you have any doubts, then maybe a startup isn’t right for you–you can always revisit the opportunity later. But if you can answer all these questions with a resounding “yes,” then by all means, go for it. It’s the best decision you’ll ever make.