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BenchPrep's founder explains how comic books can get you hired

BenchPrep has 28 employees. Ashish Rangnekar hired 27 of them. Such is life as the founder of a successful startup, where the team comes together in the founder’s image.

And BenchPrep is successful. After two rounds of funding, it’s got more than $8 million in capital to play with. Cash like that is easier to raise when your business has more users than Wyoming has people.

Half a million people have tried BenchPrep’s courses, which are gamified, meaning that studying for standardized tests like the MCAT sucks out less of each user’s soul. The software is also adaptive and travels across computers, tablets and smartphones.

Here are five tips on how to build the most important asset a startup can have — its people.

The one question he asks everyone

The one thing I do in all my interviews, irrespective of what I’m hiring for: a simple analytical question. CMO to office manager, I ask the exact same question.

It’s a guesstimation problem: How many traffic lights are there in the city of Chicago? And it’s not about how they answer, it’s about their thinking process. How do you work with me to answer it? Ask me all of the questions you have, I’m here to work with you and help you. If you make assumptions, tell me the assumptions you’ve made.

The answer is not important — I don’t know the right answer, actually.

[Editor’s note: After some vigorous Googling, I discovered that my guess — 20,000 — was off by a less-than-shameful margin. Email editor@chicagogrid.com to find out what the answer is.]

Relevant email > cover letter

I’m not a big fan of cover letters. More a fan of a relevant, small email. Most of the people we hire are fresh grads with two to three years of experience. Candidly, I don’t believe that there is enough evidence or work experience to have strong enough correlations to be able to draft out a cover letter. As an employer who’s read through 500 of these, I know exactly when it’s template. I would recommend not to write a cover letter unless there’s a compelling reason.

The email you send, I’m a big fan of making the email very relevant. It takes no more than 15 minutes to add things that make it very personal to me and to the company. It draws attention. It doesn’t guarantee an interview, but when you have to read through 500 cover letters and resumes, it sticks out.

Show passion

One of the questions I typically ask is, let’s say you have $5 million sitting in your bank account — how would you live your life? Let’s put money in the bank account so it’s not the driving factor. If the day-to-day hassles are taken care of, what would you do?

What I want in an answer is an emotional connection toward a particular cause or activity or way of living. I don’t think that what specifically they’re passionate about matters at all. What matters is what they’ve done toward it.

One of our front-end developers said that he is passionate about telling stories through design. I dig in, and he says that he actually loves creating comic books. He was actually carrying three comic books he’d created. He hadn’t intended to show me, but when I asked he told me that he’d been doing this for the last five years, working toward a comic book conference that’ll be in Chicago in six months. He said his first few paychecks would be used for a paper cutting machine that’d allow him to cut the comic books properly. That just explains that there’s this one thing that he’s emotionally connected, and we’ve been able to channel that passion.

The right answer is the wrong answer

Young graduates are very defensive when they answer a question. They have a notion of what a right answer is, and whether they might or might not believe it, they give out a safe answer.

For a startup like this, one of the biggest questions is, it’s OK to challenge things about what we’re doing that might not be working. When I ask them about the space, product, services we have, I get a very defensive but a “correct” answer. Everyone says, I would have loved it, this and that.

Make a question out of your criticism: “I would have been really excited if this option had been available. So Ashish, is that something you guys are working on?” That’s a good way to call something out, throwing a question at me so I can explain my thoughts about the space.

Advice to other startups

It was very different when we were hiring our first 10 employees. I wanted them to have a very different personality than employees 11 to 28. The first 10 employees, they would come in and have absolutely no structure in place and still strive without any formal or informal structure. With the next batch, I wanted them to fit into a structure in some form or shape. That was the big difference.