Hey @TheRock, Invest In This Awesome Health Startup!

Dear Dwayne (aka The Rock),

Know you’re busy filming movies & saving franchises, conquering social media thanks to your 4.5 million Twitter fans & 8.5 million Facebook fans, wrestling (sorry ‘bout that injury!), and working out a ton. I get it— that’s the life of a kick-butt celebrity!

Buuut I’ve been working to reach out & ask if you’d consider adding one more thing to your gargantuan-sized plate: investing in an epic, fast-growing health startup.

That startup is Greatist, a company working to build this generation’s first truly-trusted health and wellness brand and business with the mission of helping the world think of health and wellness in a healthier way and a vision to simply make healthier choices easier for everyone.

Two years ago, we started with high-quality content, the kind you’d be proud to share (every fact in every article is cited by a PubMed study and each post is approved by at least two experts from our incredible expert network) and now we’re the fastest-growing site in the space, with 3 million unique visitors per month (!), with syndication partners like TIME Magazine, Yahoo!, and USA Today. We’re also not so bad at social ourselves with over 160k followers across our Pinterest, Twitter, Facebook, Instagram, and others. And we’ve built a world-class editorial and engineering team, especially since our acquisition of Sportaneous. What’s really exciting is what’s next: getting people moving. We want to build the social layer on top of health & fitness data tracking— to take the metrics people are increasingly tracking and do fun things with them along with friends.

Happy to share more on all that later, but first here’s the deal: we’re looking for investors who believe they can have play an instrumental role in helping Greatist to become THE health and wellness brand that’s on the people’s side. So fittingly, as The People’s Champion, your name’s at the top of our all-star dream investor team. Here’s why:

Your #greatist personality. You’ve got the Greatist brand down pat. People trust you, recognizing your hard work and passion while admiring your positive, fun-loving mentality. You’re also  super engaged with your audience and fans, motivating them to “stand fearless in the face of adversity and bring it every day” with you and your Team Bring It. That’s difficult to do & you’re clearly committed to it— engaging with your fans & making them feel special, one at time, in a way that most celebrities don’t care to do (or just pay others to do for them).

Your #greatist passion for health & fitness. At Greatist, we champion celebrating the healthier choices people make, the #imagreatist mentality, without feeling bad about the poor choices— and you embody that. You wake up at 6am, push through a crazy workout, then strap on a pair of CGI wings and make movies like the Tooth Fairy (where the joke’s on… everyone?). You challenge John Cena to throwdown, then sing Sam Cooke’s classic You Send Me on TV. You blow shit up for your day job, then say motivational & kind things like this. That inspires & resonates with people, exactly what we’re trying to achieve with Greatist.

Greatist is different because, like you, we only do things in a high-quality way. We’re in it because, like you, we care passionately about achieving something great for the world, be it a few lost pounds or laughs. And we’re doing this because, like you, we love every second of what we do.

So, long story short (too late?), would like to share a bit more in person about what we’re doing with Greatist and how we’re doing it— to hear your thoughts about reaching & motivating fans, inspiring the world, and more— with the hopes of convincing you why this is an awesome opportunity to:

1) Make a Difference. Partner with an up-and-coming innovative startup trying to change the world, helping a meaningful cause that’s near and dear to you. We’re a startup filled with people who are passionate about helping the world to make healthier choices— and we’re going to… hopefully with your help!

2) Get Buzz/Press in a Whole New Way. This could be a completely new, different angle to your growing success in the web world— and show you’re in touch with what’s exciting in the space. Other celebrities, like Ashton Kutcher, Kanye West, Lady Gaga, Justin Timberlake, Justin Bieber, and even Leonardo DiCaprio have recently invested startups with big exposure.

3) Get Involved Early With the Rocketship of The Future. You’ve got some huge movies and roles ahead of you & we, too, have been growing like gangbusters. We just acquired a smaller startup and were even nominated for a Webby.  Like all good startups, our curve is up & to the right… but it’s just the very beginning. We’re planning to build a billion-dollar, 100-year company.

Know you’re busy, but think meeting with Greatist will be well worth your time: a very cool opportunity for you to support, an interesting world to get involved in, and a wonderful cause to champion. The amount of money you invest is (obviously) not as important as your potential commitment and involvement. If you believe in us as much as we do, then there’s no way we can’t succeed.

So, Dwayne, if you’ve got a second to even think about this, let’s chat ASAP. And if the person who’s reading this isn’t The Rock, but knows him or went to school with him or knows the person that one time he looked funny at in college at UM, let me know ASAP too. Will jump on any leads I can get! (And in that case, thanks for reading, whoever you are, and in the future, though this time it’s cool, don’t get in the habit of reading stuff that isn’t addressed to you, you sneaky reader.)

Thanks Dwayne & would love to connect when you’re in NYC next. Just let me know when works, though preferably sooner rather than later.

Thanks again,

—
The Derek
ceo & founder, Greatist + #TeamBringIt
derek [at] greatist.com

Lessons Learned After Two Years As a Startup Founder

Today is the two-year anniversary of Greatist. One year ago, I published a post with the lessons I learned after one year as a startup founder. It forced me to communicate how I had changed in a challenging, but important way. So now I’ve decided to make this into tradition (two straight years is enough to make a tradition, right?) and do it again. Hooraaay!

This post is not about Greatist’s growth, though hey it’s worth mentioning that our growth has been pretty remarkable (800,000 unique visitors a year ago is now 3 million uniques, 7 full-time employees now 17 full-time employees). Our audience has never been more engaged, more obsessed with what we’re doing. We launched a major site redesign. The content has never ever been better—and syndication with places like TIME Magazine, Yahoo!, USA Today, and others proves we’re not the only ones who feel that way. We’ve got a lead that only continues to grow, unique positioning in the center of an exploding ecosystem, expertness in social, and now a world-class editorial and engineering team. Most importantly, we know what we’re building next (because our audience told us) and it’s going to be freakin’ awesome. I’ve never felt more positive that we can build this generation’s defining health and wellness brand and business. Seriously.

That said, at the same time everything is an absolute mess and I have little to no clue what I’m doing. Things are either awesome or terrifying not just day-to-day, but hour-to-hour. I know people say “startups are a rollercoaster” sometimes and then people politely laugh and nod. But a startup really is the world’s craziest rollercoaster. It never slows down. It barrels up sharply without notice and plummets before you can see the drop coming. You’re constantly elated and energized, but also constantly on the edge of projectile vomiting over everyone (just me?). Rollercoaster indeed.

Here are 8 new lessons (adding on to last year’s 8) I’ve learned this past year on the startup rollercoaster, again with the hopes that they’ll be helpful to people in the same position (or close to it, at least). But mostly this is for me.

1.      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 the way I talk about things meaningfully change 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 douchey and a lot less, well, “busy.” I call 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 (well, technically that’s our Smiles Director Giuliana’s job), 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, shitty 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, most don’t but everyone knows they should. 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 cider in your ear. 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. 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, though 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. 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 a lightspeed (aside: a stunning realization I had recently was that even though every day seems like it flies by, 2 years somehow seems like 5, maybe more). I love every part of it, every new stage and every new challenge. Seriously. Gives me chills how much I love it and sometimes cares 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 water. 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 in 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.