Lessons Learned After Two Years As a Startup Founder
1. A positive attitude can be unexpectedly powerful.
Imagine if every time you opened your inbox you said “I love email” instead of “Ugh, email is slowly, but surely murdering me with a million tiny iPhone notifications straight to the heart.” It makes sense that you’d hate email that much less, right? This is a simple concept, but something I’ve found to be unbelievably powerful over the past year. Just changing how I talk about things has meaningfully changed my perception. Example: I decided to stop telling people how busy I was all the time because, c’mon, everyone is freakin’ busy and no one cares. The minute I committed to not say that, I felt a little less douch-y and a lot less, well, “busy.” I’ve been calling this “intentionality” and have found it apply to almost everything, both to me personally and as an example to the company as a whole.
Sometimes I feel my job at Greatist is basically just making people smile, reminding them that every annoyance on the way to something great is just a hiccup. Because if I don’t, things get sticky. Small stuff affects attitude and that can snowball. Grumbling about this or that meeting can lead to grumbling in general. In the office, every day comes with a zillion new potential stressors, each of which can add up to one shitty day… unless, you know, you turn that frown upside down. I’ve learned, with effort, that I can and that I need to.
2. Hiring the best people takes building the best long-term relationships.
It’s rare to come across someone blindly through a job post and get to know them well enough to offer them a job. And rarer that it works (partly because I think a surprising amount of people want to “work for a startup,” but don’t really understand what comes with the territory (risk, lack of structure, mediocre pay) until far too late). In fact, almost all of our recent hires at Greatist have been people I (or someone on my team) met more than a year ago or have known for an even longer time. A relationship with mutual respect and understanding has grown, where cultural fit is just the very beginning if a long, long-term process. When super talented people begin looking for a change, they’ve already built a network and group of friends who wants to work with them… and they want to work with!
Does this mean there’s no way to find anyone out of the blue? Absolutely not. But I’ve been devoting more and more time to building real relationships with people who’ve applied to jobs at Greatist before… or even just strengthening relationships with people I’ve always had on my “to hire” wishlist. And those are increasingly paying off in the absolutely best ways for everyone involved.
3. Do due diligence and then some.
Oof. This is a lesson learned the hard way. Last year, I wrote about how one of the major things I learned was that sometimes you had to make mistakes for yourself. The good (er, bad?) news is that still sure hasn’t changed. Doing due diligence is like putting on a seat belt in a NYC taxi cab, you know you should but also you don’t. Say you’ve gotten to know someone, you’re both on the same page, and hey, they seem positively perfect. But perfect is scary. Though chances are they’re everything you think they are, it’s also possible you’ll get over-excited, overlook the diligence you know you have to do, and potentially end up with cidah in your eay-ah. Better put on a seat belt than wait for the accident.
Due diligence is relatively easy today, too. It’s a no-brainer to ask someone for references or reach out to LinkedIn coworkers of theirs. It’s simple to do a deeeep Google search. It’s obvious that asking a friend to conduct a technical test (or, at a minimum, take a look at their code on GitHub) is a must-do. But sometimes we forget. And sometimes we learn far too late that the person we really wanted someone to be (that maybe even that person honestly really wanted to be too) wasn’t the person you needed at all.
4. Don’t get six pack abs in six weeks.
I got six pack abs in six weeks. It sucked.
5. Learn to get rid of all the stuff in your head so you can focus on the things that matter.
My brain is like an internet browser window, usually way too full of tabs. I’m convinced that removing as much as possible from your head allows you to think freely, focus on what’s really important, and opens up space for creativity. So I’m obsessed with it. But the more tabs, the slower the browser goes. So I’ve learned to exit out of the following: things I forgot to finish, things I’m worried I’ll forget, things I’m waiting on, errands, bigger tasks without specific action steps, appointments & recurring tasks, and personal goals I want to reach. Over time, I’ve created hacked-together solutions I swear by to get them out of my head: my Master Planner, my @waitingfor gmail label, Boomerang, Nudgemail, Captio Instapaper, Google Calendar, and then some (for some reason I actually imagine this a lot, if you’ll pardon my fandom, like the pensieve from Harry Potter). The key is clearing and freeing the mind by moving anything that would distract somewhere you have full confidence you’ll never miss later.
The other thing I’ve taken up is meditation. Super simple: Just five minutes of closing my eyes, sitting upright, and focusing on my breath coming in and out. I’ve struggled quite a bit with fitting meditation into my life regularly (even after the great BJ Fogg taught me the ultimate hack: The best way is to tie it to a habit I already have and make that a “trigger” for this new habit). I just couldn’t figure out what habit to tie it to. Then, my incredible friend Johnny Angellilli suggested I do it after I work out at the gym and it just clicked. Right before the shower, every time, I take five minutes to clear my head. And wowza does it work wonders for my stress, my happiness, my focus, and my ability.
6. The difference between someone who’s good & someone who’s truly special is huge.
The so-called startup “unicorn” is someone that isn’t just better at their job than other people, but 10x better. They’re astonishingly good. If it takes a week for someone to build something, it takes them a night. If it takes a month to come up with the right idea, it takes them a split second. If you’re wondering if you have any unicorns on your team, you don’t. If success is really binary, then you better have quite a few of them… and get rid of the ones that aren’t (fire fast… or as fast as you can).
7. I’m not alone, even if it sure feels that way sometimes.
Running a startup is hard. No one really, truly knows what it’s like. No one on your team shoulders the same responsibilities, the same burden, the same pressure, no matter how involved they may be. You can be their friend, but you can’t be their friend. It’s awfully, terrifyingly lonely sometimes. Especially as a solo, first-time founder. And that’s okay, since perhaps the right word is more accurately “aloneness,” not “loneliness.” Perhaps that’s one of the curses of entrepreneurship, but I’ve found it can be profoundly helped through connecting with people who are going through similar things, through commiserating and laughing with other founders who get it. Catharsis FTW!
No startup is the same, but other people deal with many of the same big challenges and the same day-to-day madness. Putting time and effort into building those types of relationships and getting that touch, that connection, is so key to surviving. In particular, I’ve found the NYC community to be particularly giving, generous, and open — and have been lucky enough to build friendships with people doing unbelievable things that can still spare a moment every few months to chat about how we’re all in this together.
8. Passion FTW.
In two years, I’ve grown mightily as a leader as my role has evolved at lightspeed. I love every part of it, every new stage, and every new challenge. Seriously. It gives me chills how much I love it and sometimes scares me how much I would rather be working on Greatist than doing nearly anything else. But this shit is it hard. It seems like I’ve pitched Greatist a billion times. I have to deal with projections, insurance, accounting, reimbursements, legal contracts, and PEOs a shocking amount of my day. But none of that can dampen my passion. None of that can get in the way of how excited I can get when I talk about why we’re doing what we’re doing and why that matters. Every time I talk to someone about Greatist is a new chance to build a life-long fan. Every time I chat with a team member is a new chance to re-communicate why what we’re doing matters so much. Every moment I’m working on something is a new chance to learn something new and get better. Better so I can push and be pushed by the people I work with. Better so I can steer this ship in the right direction, no matter how choppy the waters. Better so I can grow into a leader that can build an empire that lasts, that’s built the right way so we can make a difference the best way. Better because, well, I don’t know any other way. Keeping the fire “on” all the time can be exhausting, but if anyone knows how to turn this fire off, good luck explaining it to me.
