Lessons Learned After Four Years as a Startup Founder

1. Beware the “trap of cool.”

I’ve always done things differently. Mostly because I believe if you do the same thing everyone else does, you’ll have the same impact everyone else has. And no thanks, that’s not for me.

At Greatist we’ve got a big, improbable (though still probable!) goal. We learn from the best, improve on the great, and throw in some innovative ideas of our own — all done “The Greatist Way” — in order to get there. And I similarly work to achieve the same thing personally, in ways that are true to myself.

But sometimes I get caught up in other things. Sometimes, whether it’s due to inexperience or insecurity or both, I get distracted by something shiny. Something like, oh, “building an app,” “raising a big round of institutional funding,” or “being chosen as a launch partner.” I get frustrated by not getting placed on an exclusive list, receiving an invite to a special party, or being asked to speak at a big-time industry event.

I’m not saying any of the above is inherently right or wrong, good or bad. The only thing that matters is whether it actually matters. And if it doesn’t, in fact, matter? If you’re pretending to “keep up with the Joneses” or obsessing over what the “cool kids do” or pursuing hype for the sake of hype? That, to me, is the trap of cool. It looks shiny on the outside, but man does it suck inside. Because, well duh, “it’s a trap!”

The truth is almost all “overnight success” takes 7–10 years. And the few companies that get there have leaders that are all totally differently and usually profoundly themselves. You know, they’re “cool” in the actual meaning of the word.

I get all that. I don’t think I’ve ever wanted to be “cool” for the sake of “cool.” But I sure have fallen deep into the trap at times. I’ve gotten lost and it’s cost the company big time. Sure, we’ve been able to survive and weather each of these storms (“mistakes well handled”), but in each case the fault has basically been my own — getting caught up in what will sound good, look good, and seem impressive to everyone else. And each time this has happened has been embarrassing and frustrating. Shameful, even. Each time I’ve been angry at myself and disheartened. But I’m learning. The only thing we (and I) really compete with is ourselves. The only way to build our business is our way. It’s okay (preferable, even) to be uncool and unreasonable. We don’t need to convince the skeptics (and pretend to be something or someone we’re not), we simply need to find the true believers.

Of course this (as all things worth doing) is easier said than done.

2. Setting the right intention in advance can have a huge impact.

For most of the past four years I’ve been writing an absurd amount of notes after every meeting every day in my Master Planner. That’s just one of the many weird and obsessive things I do. But the newest habit I’ve picked up over just the last year is setting an “intention” for every meeting.

It goes something like this: Every evening I plan for the day ahead and now it includes whether I want to be “calm” and “thoughtful” or “focused” and “direct.” It includes any important points I want to hit on, any background I should bring up, and any goal to push toward. It helps me act as a “director” of sorts for my own day and it’s led to a huge change in the mindfulness, authenticity, clarity, and focus I bring to each meeting. I know I’m not the only exec who can have 10 or more back-to-back meetings a day with people of all kinds to discuss all kinds of various things. Setting my intention in advance and reviewing it along with any other notes right beforehand has taken my ability to be my best all day to the next level.

I’m an increasingly big believer in intention across the board. Not only does science validate its effectiveness, but simple things like purposefully choosing to say “I love email” (instead of “ugh I get so much email and it’s just the WORST”) or “I choose to” (instead of “I have to”) can shape my whole perspective.

3. Trust your gut.

Someone wants to invest. Someone wants to help. Someone wants to make connections and give advice. But something is off. You’re not sure what, but something just seems wrong.

Run away.

Seriously. Every time I’ve felt this feeling, it’s eventually gone awry in some way. This doesn’t mean being close-minded to new opportunities, new perspective, and new types of people. This means believing in one of the most important things that’s helped me get so far: My judgement.

I’ve learned this lesson (sense a pattern?) the hard way. Run away!

4. Don’t discount the power of sheer will.

I grew up listening to audio tapes in the car with my family and the story that I remember best I can’t remember or find (if you can help, that’d be huge!). It’s the spooky tale of a radio reporter staging a mock monster attack at a local, reportedly haunted house. He’s making up the entire thing, simply pretending there’s something there… but slowly the believing, engrossed audience wills the monster into being and it devours him. Awkward.

The story stuck with me because of the power of belief and focus. The monster seems so real to so many people that it simply becomes real. In some way I think of starting a company similarly. It’s not enough to want it, but “when you believe in a thing, believe in it all the way,” then something can be built from nothing.

After a bunch of my mistakes piled up, mid-2014 was a tough time. Our assumptions were overconfident and suddenly the company was literally running out of money. I took over sales, started responding to inbound interest myself, and somehow pushed us to profitability from August through January (in February we hired a full-time, impressive sales team and, since, are on track to be profitable again soon and then some).

In some ways I guess any CEO and Founder of a company is basically on “cheat codes” (fun aside: speaking of cheat codes, or at least easter eggs, try entering the Konami Code when you’re on Greatist and see what happens!) when it comes to sales. For one, they can usually can sell the product better than anyone and, for two, they know exactly what they’ve got to offer and what they don’t. This meant I always set expectations right and never sold something we couldn’t deliver on. It means I successfully convinced potential partners how compelling our offering actually wa s(we basically sell big, beautiful, engagement-driven sponsorship campaigns) before I nearly botched all the rest of the sales process, pricing, and then some since I didn’t have any experience in any of this. But for the most part? We were successful because we had be. A year ago I’d never sold any form of advertising before, Today I’ve closed well over $1M.

More and more I learn the CEO’s role is ultimately to lean into the hardest, most uncomfortable parts of the company. Until I started selling, we hadn’t had much success…and that was in no small part because I didn’t personally really know what it took, how it worked, or who would be great at it. Once I experienced sales myself (and, with some luck, didn’t turn out to be half bad), the opportunity opened up and starting making tangible sense for the company. We wouldn’t be here today without the revenue I was able to generate, sure. But more importantly we wouldn’t be able to build towards tomorrow without the experience and understanding I gained from leaning in and JFDI myself.

5. Your company is a team, not a family.

A lot of people have been let go (or left) Greatist. It’s usually a good thing (for both parties), but it almost always ends sadly and awkwardly. I’m not sure it should be that way.

Despite working my hardest to be as transparent a leader as possible (we share revenue, expenses, investment materials, etc… publicly to all our employees on a regular basis), I’ve always felt like too much was left unsaid and ambiguous about each employee’s responsibilities under the current format of “jobs.” And I’ve especially felt this when we’ve repeatedly failed to find new roles for all-star team members ready for their next challenge. Many times we’ve eventually concluded together that that next challenge isn’t at Greatist, but getting there has often taken months of discomfort and agony — and, worse, built resentment and tainted great relationships with people I cared about. That sucks.

So I’ve been actively looking for a way to handle this growing sense of “something is broken” and the much smarter people that wrote The Alliance beat me to a fix. The solution is re-thinking the modern startup “job” and the unit it typically comes in. Discussing general alignment and career development only once a year during performance reviews in a position without an end date is ineffective and just plain stupid.

Reid Hoffman, Ben Casnocha, and Chris Yeh suggest a new way to look at work; a “Tour of Duty” that comes in three different flavors depending on the level of mission alignment/job responsibilities, but all of which include a specific mission to accomplish, skills to learn on the way, and a general sense of how long the Tour will be (somewhere between 2–5 years most likely). Then, at the end, if all things go to plan a new Tour starts with the same company. If not, then at least everyone is on the same page and constantly communicating about what they’re looking for. It’s true companies grow fastest when their employees do too — the best thing for any individual team member is to win the championship as a team. And this format brings the conversation of what growth actually means to each employee, what’s next, and how they’re actually feeling to the forefront (and in written form). At Greatist, we’re very focused on creating the healthiest workplace — and so I’m pretty obsessed with this new re-imagination of the modern job — and excited to implement this (in our own way) ASAP. [Note: it’s now been nearly two years since we’ve implemented Tours of Duty and we haven’t looked back — it’s absolutely the real deal and I recommend it to everyone.]

6. Don’t disappear into the fire.

I am not Greatist. And Greatist is not me.

Jerry Colonna (or, as I like to refer to him, “startup Yoda”) shared a story with me once about an old master potter determined to develop the most perfect glaze. One of the most successful potters around, he nonetheless becomes obsessed with this glaze and spends every waking second working on it. No matter what he tries or how hard he works, he just can’t produce the glaze he’s imagined. Finally, one day he walks into the fully fired kiln and dies. The next day his assistants open the kiln find pots covered with, yup there it is, the most perfect glaze.

Is this a tragic story? A beautiful one?

To me, it’s a little bit of both. Sometimes I still have to “disappear into the fire,” but a lot less than I think and a lot less than I did. Last year I began in earnest the journey of separating myself from my business — and this year I’ve started truly seeing the awesome impact it’s had. The more I get out of the way, the faster Greatist grows. The more balance I find, the better leader I become. This is a lesson that took me too long to learn, but I’m glad I started when I did. Greatist likely wouldn’t be here today if I hadn’t. And if I hadn’t, there’s no way we’d be producing such beautifully glazed pots.

It’s worth mentioning that my growing commitment to meditation has been a huge part of this increased calmness. Meditation is like defragging my personal hard drive. And my practice is pretty simple. I simply spend 5–10 minutes focusing on my breathing every morning after waking up (and peeing, obviously). I’m no meditation snob, though, and encourage everyone to find it their own way, on their own time, and for their own reasons. But consider this just another friendly “give it a try.” It’s been huge for me.

7. The job is working “on” the business, not “in” it.

A similar lesson I’ve made more progress on and seen an even bigger impact from is setting time aside to work “on” the business, not “in” it. This is simple in theory, but much harder in practice (at least for me).

Time and time again, strategic long-term planning and critical “are we on track” analysis takes a back seat to the day-to-day emails, meetings, and “let me review the agreement before signing.” I love the big-picture stuff more and always have — but I also love the grind, the building, the little things. And since it’s so much easier to do what’s next in my inbox than work through that new org structure plan, I find I have to literally jam “Task Time,” “Be Creative,” and a 1-week break every six months into my calendar or else it doesn’t happen.

When I take my unplug, solo retreats every six months (I spent part of my first one a couple years ago in a castle in Scotland and have called it my “castlecation” ever since), there’s only me, my thoughts, lots of books, and my notebook. A few days unplugged clears my mind and the next few days are pure magic, moving the company forward more in one week than I typically move it in months. So take a break!

8. The importance of gratitude.

The vast, vast majority of startups fail within the first three years. And we didn’t. In some ways this makes me feel like an elder statesman all of a sudden, possibly a little wiser and definitely a little crankier.

The truth, though, is that these four years have been by far my most humbling.

It’s no doubt true “the more I learn, the more I realize how much I don’t know.” And the last four years have beaten out a lot of my loud, insecure ego fountain and replaced it with a quiet, babbling confidence brook. I’m not just tired of telling people “we’re crushing ittt,” I now realize no one really gives a sh*t either way. And I appreciate the reason we’re still here isn’t because of me — in fact, it’s probably in spite of me. The more I’ve gotten out of the way, the more our amazing team, advisors, investors, partners, and others have helped pave the path to our most impressive year yet.

I’m profoundly grateful to them. I’m grateful to my friends and family. I’m grateful for the growth I’ve had and the life I lead. I’m grateful for the many obstacles we’ve tackled and WFIO conversations we’ve had and resolved. I’m grateful for how many great people have worked with the company and gone. I’m grateful for how many amazing people work here today and are only at the very beginning of what they can accomplish. I’m grateful for how much we mean to our audience and for how much they care. And I’m grateful to the market and the timing for being righter than ever (because that sure helps too).

As an entrepreneur, I’m always focused on how much further we have to go. But every now and then I’m learning it’s good to be grateful for how far we’ve come.

I wrote all of this before looking back at the posts I’ve written in the years past. But now that I have, I’m pretty blown away by how much, well, learning I’ve actually done. Conclusions like “Sometimes you just have to make mistakes for yourself” (Year One), “The only way to build something different is to do things differently” (Year One), “Positive attitude can be unexpectedly powerful” (Year Two), “It doesn’t get easier” (Year Three), and “You and your company are not the same thing” (Year Three) from years past show lessons learned yesterday set the foundation for the lessons learned today. And the lessons learned today shape me into the leader I can be tomorrow.

Four years is a long time and I’ve learned a lot. I’m grateful that I still get to work hard every day on something worth doing — and I’m grateful most of all that my love for this thing hasn’t gone away but strengthened instead.