7 Lessons From My First Year as an Entrepreneur

A year ago, I started  Greatist with no real clue what I was doing. We’re now the fastest-growing health and fitness site on the Web, so a lot has gone right. But a lot has als0 gone wrong. A year ago, I’d never really hired someone. Never really fired someone. Never incorporated a company in Delaware. Never spent days accounting in Excel, signed an office lease, paid the IRS, saved a crashing website, negotiated with a potential acquirer, or been responsible for six people’s paychecks. But those things could always have been figured out.

The biggest challenges, instead, have been personal, and on that level, it’s never been harder. I’ve never been so busy, so behind, so unsatisfied with how much I can accomplish with the mere 24 hours in each day. At the same time, I’ve never been happier. I’ve never been more optimistic, more excited for what can be achieved,  more able to genuinely say I love every second of what I’m doing. Now I can.

Here are 7 lessons I’ve learned this past year of being an entrepreneur:

     

  1. Starting something for the first time is really, really hard. Imagine the hardest thing you’ve ever worked on. Now imagine that thing is the most important thing you’ve ever done. Then imagine you have no idea what you’re doing. Most startups are different, and most founder motivations and ambitions unique – but no matter what it is, if you think it’s going to be easy, you’re wrong. This experience has been way harder than anything I’ve ever been challenged with. I love that challenge. A startup is a to-do list with infinite scroll. It’s true that it’s never been easier to start a startup, but that doesn’t mean that starting a startup is remotely easy.
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  3. Sometimes you just have to make mistakes for yourself. There’s an unbelievable amount of brilliant, experienced entrepreneurs/investors/male models regularly sharing advice on the web ( Vin VacantiFred WilsonMark CubanChris DixonBen HorowitzAlbert WengerRob GoBijan SabetBrad FeldJason Goldberg, just to name a few of my favorites). Those +  Quora can answer nearly any question. But you’re going to mess up anyway. I recognized that it was likely I’d make a lot of mistakes, but I’ve realized I had to make an awful lot of them for myself. Example: knowing that you should fire someone who isn’t working out because they’re hurting the team’s culture quickly is much easier than actually fully realizing that’s what’s happening and then acting on it. I knew, but I didn’t really know until I felt the taste of mistake in my mouth. And it tastes salty.
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  5. Asking others for help and meaning it is important. I’m the worst at asking for help, but I’m getting better. Entrepreneurs are, by nature, usually confident, positive and optimistic, but if success in startups is the outcome of a million random factors, inspiring help from others is  among the most important. Asking for help is humbling, but the minute you genuinely eat your pride, tell it like it is, and share what you need is the minute things can change. If what you’ve built is truly meaningful and impressive, let your guard down. Share your hardest challenges, biggest worries and scariest fears, and people will help if they can.
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  7. Surround yourself with friends who will remind you you’re awesome when you need it, and call you out when it’s time. In my experience, entrepreneurship is sort of like a see-saw: sometimes it seems like everything is falling apart and, at others, that huge thing you’ve been working to achieve may actually be possible. Friends can be an escape, sure (and you need escapes, big time), but they can also be the external support you need most. It’s hard to keep up with friends regularly when you’re starting a company, but each time I do, I’ve been working increasingly hard to allow them to push me in the way I personally need pushing (and, by the way, try to do the same right back!).
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  9. Sharing what you’ve learned with others can pay back in a million different ways. With Greatist, I’ve found putting the time into teaching others has paid me back many times over. I started a class with  Skillshare mostly because two awesome buddies,  Peter Boyce and  Scott Britton, asked me to. I taught  How to Grow from 0 to 250,000 Organic Uniques in Under 6 Months with no expectations… and have since taught a few more. Each time I’ve been shocked by how much I’ve learned, from the people who take the class and those who follow up afterwards. I’ve made great friends, started major brand partnerships, been introduced to some remarkable people, and brainstormed amazing ideas with others because of them.
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  11. Schedule in specific time to think and be creative. Emails, meetings, sleep, repeat… and suddenly a week has gone by without time to think. This might sound a little silly, but put time blocks into your calendar to just think. I’ve literally just started scheduling “thinking time” on my calendar at regular intervals, and beg everyone on my team to do the same. Also, a lot of my most creative ideas come from doing, seeing, experiencing something else entirely. Some of my best ideas have come from seeing a random movie, attending a jazz concert, or taking the time to explore somewhere new.
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  13. The only way to build something different is to do things differently. A good friend, Runkeeper’s  Jason Jacobs, said in an interview once: “We have no exit strategy, we have longtime horizons. We are digging our heels in and we are going to slog through this over a long period of time.” I’ve noticed it’s increasingly easy for people in the startup community to become swept up in, “That’s just what everyone else is doing.” It obviously makes some sense to do what others have done to fit how everyone else defines success, but I’m learning that success, to me, is different. I’m getting better and better at realizing that to achieve something different, we need to do different things.
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