Lessons Learned After Year One As a Startup Founder

It’s the one year anniversary of Greatist, this little ‘ol startup that launched out of a Starbucks in San Francisco with the crazy hope of building the first truly trusted health and fitness brand and business. Now, just 365 days later, we’ve built what I’m pretty sure is the fastest-growing health & lifestyle site on the web, with nearly 800,000 uniques in March, an average of 35% growth each of the last 5 months, and an incredible community of followers and fans. We think it’s because our super high-quality content (every fact cited by a PubMed study, every article approved by multiple experts) is shared in a way that’s accessible, fun, and judgement-free, but whatever it is – something’s working.

At Greatist, we believe it’s hard to always make the best choices, so we simply want to help make it easier for everyone to make better ones. And we, now a passionate team of 7 working out of our own awesome office in NYC, want to build the first great health and lifestyle brand and business built on top of those core values.

… Or that’s the pitch, at least. A lot has gone right. But a lot has also gone wrong. A year ago, I started this with no real clue what I was doing – and I still feel mostly the same way. I’d never really hired someone. Never really fired someone. Never incorporated a company in Delaware. Never managed my own P&L, spent days accounting in Excel, saved a crashing site, signed an office lease, paid the IRS, negotiated with a potential acquirer, or been responsible for six people’s paychecks. But those things could always have been figured out. The biggest challenge, instead, has 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 limited amount of time I have each day (just 24 hours– really?!). Of course, at the same time, I’ve never been happier. I’ve never been more optimistic, more knowledgeable about what I’m trying to do, and more excited for what can be achieved. I’ve never been able to genuinely say I love every second of what I’m doing. Now I can.

Through this past year, I’ve struggled and succeeded as a leader – failing time and time again, earning trust and respect the hard way, and (I’d like to think) learning business skills and realities through “mistakes well handled.” I reinvent myself as a CEO and founder one week at a time. And every week I’m better than the last. Every week I know more than I did and, at the same time, recognize how much more I actually have to learn. So here are eight mostly random lessons I’ve learned this past year, with the hopes of helping those who are considering starting something, are in the exciting early stages, or are already underway and curious whether there’s something in here that they, too, can learn (or did already):

1. Starting something for the first time is really, really hard.

It’s not all hoodies, flip flops, and Justin Timberlake. It’s not even all conferences, craft beer, and swanky open lofts. 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. Voila – instant startup! Most startups are different and most founder motivations and ambitions unique for sure – but no matter what it is, if you think it’s going to be easy, you’re wrong. I definitely didn’t think it’d be a walk in the park (nor am I complaining one bit), but this experience has been way harder than anything I’ve ever been challenged with. I love that challenge. It’s awesome to try to conquer. I recommend it to anyone who can stomach it. But 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.

2. 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 Sabet, Brad Feld, Jason Goldberg, just to name a few of my favorites). Those + Quora can answer nearly any question. You can (and should) read them all. But you’re going to fuck up anyway. I recognized that it was likely I’d make a lot of mistakes, so I worked for a startup out of college because I thought that if I could see someone else make the mistakes, I’d make other ones instead. That made sense to me, at least in theory. But the truth is I’ve realized I had to make an awful lot of them for myself. Example 1: 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. Example 2: sticking to your core mission and integrity in any circumstance is extraordinarily hard when that circumstance can keep you from going bankrupt. I knew, but I didn’t really know until I felt the taste of mistake in my mouth. And it tastes salty.

3. Asking others for help and meaning it is super important.

I’m the worst at asking for help, but I’m getting better. A year ago, I couldn’t have imagined how important this was. Entrepreneurs are, by nature, usually confident, positive, and optimistic. That’s awesome – and clearly can be useful at times. 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. It’s scary and hard and makes you vulnerable. But I’ve found the minute you genuinely eat your pride, tell it like it is, and share what you need is the minute things can change. I’m lucky enough to be surrounded by wise and gracious mentors, inspiring friends, brilliant entrepreneurs, and awesome team members. But until I ask for their help, not as many of those great adjectives show. If what you’ve built is truly meaningful and impressive, let your guard down. Share your hardest challenges, your biggest worries, your scariest fears. And people will help if they can. Because if you surround yourself with good people, good people want to help – just like you would want to help, right? This lesson has been among the hardest for me to learn and I’ve still got a long way to go, but has been immeasurably helpful, especially these last few months.

4. Surround yourself with friends who will remind you you’re awesome when you need it and shit on you when it’s time.

In my experience, entrepreneurship is sort of like a see-saw: sometimes it seems like everything is falling apart at the seams and, at others, like 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. When a buddy shoots you an email, out of the blue, that something from your product made them better today– that can cure the lowest lows. And when you’re a million miles in the clouds, talking about a million this and a million that, a former roommate of yours can suggest you to take a breather, eat some humble pie, and remind you of that time you did that thing in that place with that person that we do not speak of any longer. 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!).

5. Sharing what you’ve learned with others can pay back in a million different ways.

I’m not a teacher, but I love teaching. When I built an organization in college to last that has actually lasted, I worked with the Office of Student Life to share those lessons and build them into the curriculum for students starting new organizations. I did it purely because I figured it made sense to make it easier for others to do meaningful things and, honestly, haven’t thought all that much about whether it’s made a difference or not since then. But, 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 two more (with two more on the horizon). They take prep time and kill a valuable evening. But each time I’ve been shocked by how much I’ve learned. From the people who take the class. From the people 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. I’ve also found, much like with the gmail productivity tutorial I teach to every new team member at Greatist, that I fine-tune, consolidate, and organize my thoughts in incredibly valuable ways just in preparation. It makes sense, but never expected it to be so true and so relevant.

6. Literally schedule in specific time to think and be creative – you need it.

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 do this with writing (sometimes don’t even publish it), too. And this has been huge for me. I’m obsessed with always being more efficient with my time (whether great at it or not, I’m always trying to improve) – and I think most entrepreneurs, self-experimenters by nature, are the same way. So, at least for me, sometimes that spills over into over-optimization and I forget to think. There’s never any time for “I’ll do that when I’ve got a moment free.” So I’ve literally just started scheduling “thinking time” on my calendar at regular intervals. And  beg everyone on my team to do the same. The other thing I’ve learned is that a lot of my most creative ideas come from doing, seeing, experiencing something else entirely. It’s easy to stay in the tech/industry/startup news bubble– but some of my best ideas have come from seeing a random movie, attending a jazz concert, or taking the time to explore somewhere new and then placing old ideas into new contexts (or finding new ideas to place back into old ones).

7. Saying you know something and proving you know something are different.

I don’t pretend to be an expert. A great friend, Livestrong.com’s Adam Bornstein, calls himself ”a translator,” and I love that. Translating takes research, experts, and experience. And, up until this past January, I didn’t actually know what a “runner” was. I mean, I obviously got the concept. But I wasn’t built to be a runner and so I never ran more than however much you run in a few full-court basketball games. So I decided I was going to run a half-marathon and (with a lot more of my brother’s help than I’d like to admit), I totally did. So now I know what a runner is because, well, I am one. Is it my favorite thing? Definitely not. Am I going to run a marathon anytime soon? Unlikely. But I’m signed up for a Tough Mudder next month, so something went right (or horribly, horribly wrong).

8. The only way to build something different is to do things differently.

Another good friend, Runkeeper’s Jason Jacobs, said in an interview once: ”We have no exit strategy, we have long time horizons. We are digging our heels in and we are going to slog through this over a long period of time.” That’s not how everyone does it in startup land. But the people who do it like everyone does it in startup land aren’t Runkeeper. The benefits of doing a startup are often that purely because you don’t know how it’s done, you do it differently (and often better). But, ironically, 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.” Just like investors are often driven by pattern recognition, 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 want to do different things. I’ve definitely found myself, at times, thinking I should do things like raise VC capital, maneuver my way into the popular blogs that everyone reads, and so on less because it’d be right for Greatist, but more because it’s what everyone is doing. That’s dumb. Those things could still be the right path to take, sure. But I’m getting better and better at realizing that to achieve something different, we need to do different things.

Last year, I only knew health and fitness was a space I was passionate about personally. Today, it’s the space I want to make a difference in for the world. Last year, Greatist was basically just sketches in a moleskine notebook. Today it’s helped inform and inspire millions (nearly three million!) to make healthier choices. And it’s not longer just me anymore, but a whole team of people who share the vision of a world where better, healthier choices are easier. And a huge, passionate community of people who believe in us and need us to succeed. This year has been tough. But next year will be tougher. It will be better, too, I somehow just know it. But I’ll need to work even harder, learn even more, and continue to build an amazing team of people that will do the same in order to create a trusted brand, build a monster company, and create something truly meaningful for social change. That – and write shorter blog posts.

Derek Flanzraich is the CEO and founder of Greatist, a health and fitness media startup. This post originally appeared on his blog and was republished with permission.

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