Ben Berkowitz

Sometimes you take chances in life, and sometimes they work out.

Other times, they don’t, and then you write blog posts about them. Clearly, I’ve landed on Option B here.

After 14 months with a startup, my time at Hedgehog is coming to an end in the next few days. Let me be clear – no regrets whatsoever. It was a great learning experience.

I started as editor-in-chief, and by the time I left I was running editorial, product and corporate operations, while also overseeing branding and PR, business development, recruiting, and even helping out with FP&A and investor relations.

That’s the beauty of a startup – if you’re good at one thing, you can do other things too, and the more of them you’re good at, the more chances you’ll get.

Anyway, I thought it might be instructive (for someone, somewhere, maybe?) to share some of the life lessons I’ve learned over the last year about startup life.

• When you launch, life will be hell for four weeks. Doesn’t matter how ready you think you are. Things. Will. Happen. You should be prepared to not sleep, eat or see your family for four weeks, and after that, it will get better. Tell them all this ahead of time, so they understand. Promise it gets better, too, because it will, as long as you can take those four weeks to do absolutely nothing but work.

• One calendar. One. One email address. One. One messaging system. One. Do not get clever about these things. You will absolutely miss crucial information unless your comms and schedules are unified. Don’t be cheap about this either. There are goods and services you don’t need, but an effective comms system is table stakes.

• Hire 3 good people and pay them each 5% more than they want, instead of the 5 people you were planning to hire. Quantity is not quality, and quality is worth paying extra for. Trust me on this, it works every time.

• Don’t be precious about where you hire. I found extraordinary talents in India, Poland, the Philippines, and given a job and the opportunity to shine, I can’t even begin to tell you how brightly they shone.

• When you give people unlimited paid time off, they don’t take any time off, and you start expecting them to not take time off either. That’s bad. Give them lots of defined time off instead, everyone will feel better about it and fewer people will burn out.

• The books. Always stay on top of the books. Every day, ideally. Don’t find yourself one day realizing you’re spending 75% more than you thought you were and the end of the runway is three months closer than you expected.

• There is no substitute for seeing people in person. I know this one’s going to be a little controversial, because to some people, remote work makes all the sense in the world. And it does, to a point – but if people are working together, they will do better and work better if they see each other, at least occasionally. I’m not saying reopen all the offices, but I am saying you should budget for getting all of your people physically in one place (ideally someplace with good food) at least quarterly.

• Be honest. It’s a startup, you’re all in this together. From the owners to the junior staff, it’s you against the world. (Not really, but there’s some value in instilling that competitive mentality.) Be honest with people, tell them more than they’re accustomed to being told, keep them up to date on the fate of the business, and give them a mental ownership stake in your shared success.

Anyway, random thoughts from a random guy with a little bit of experience. Hopefully useful in some way.

It was a heck of a ride, I’ll tell you that much.