41 Lessons Learned after Five Years as a Startup Founder

Greatist turns five tomorrow.

Five years is a major milestone.

It feels like just yesterday I was working out of a 24-hour Starbucks in San Francisco and no one had ever heard of Greatist, I was convincing early employees to take nearly unpaid jobs and move into our first office (also my apartment) in NYC, and I was manually re-starting the DNS server every time we hit 1000 consecutive visitors. It seems like just yesterday I was pitching this crazy idea that a new, defining consumer health brand could change the way people thought about “healthy” and I wasn’t going to stop until I built it.

I’ve found Year Five to be the most grounding year yet, a year where both the organization and I matured most. It’s the year we started making money in earnest and even became profitable. It’s the year we reached (and beat) the 10M unique visitors per month promised land. It’s the year the team size doubled and the team average age almost doubled as well (yup, suddenly half the people that report to me have kids — REAL kids).

If an entrepreneur’s life is measured in Pokémon, let’s say it’s the year I evolved from Charmander to Charmeleon and am well on my way to Charizard (I looked it up and apparently now there’s a thing called Mega Charizard, which I guess is Jeff Bezos-level).

It’s the year I not only starting internalizing and appreciating what the role of a CEO fully is, but took meaningful steps to get there. It’s the year we crossed the threshold from sorta kinda not institutionally-backed company to absolutely venture-backed company. It’s the year I regained some swagger after what feels like years of getting my hubris beaten out of me. And it’s the year I continued my journey to being the most calm, most disciplined, most courageous person in every room.

It’s a major milestone.

To commemorate these hard, crazy, beautiful five years I’ve yet again put some time into writing and sharing my eight lessons learned. If curious, check out Year Four, Year Three, Year Two, and Year One. I’ve also moved (and lightly edited) the other four years of lessons learned from my personal blog (ha — remember blogs?) to Medium in the hopes that this can become a real resource more than just a throwaway blog post. As I say every year, I write this for me, not you. That said, I’d be thrilled if these lessons help you build something special. I definitely believe “a rising tide lifts all boats” and we need more awesome freakin’ boats.

Anyway, here goes:

1. Simplicity is mad powerful.

If a startup’s key advantages are “focus and speed” (with speed, IMO, mostly deriving from focus), then a startup’s leader must be the most focused. And I’ve struggled with this for a long time. I’ve always looked ahead to what’s next and what’s new, thinking actively about what part, if any, we should play. But I’ve now started to really relish the power of focus in an organization.

Like me (or probably because of me), Greatist struggled with focus the first few years but now we’ve swung far in the other direction — we’ve never had a more focused year than Year Five. We didn’t get distracted by almost anything, working purposefully on taking our next-gen media company to the next level — and we absolutely achieved that.

Similarly, I’ve been on an intense simplification kick myself to boot. I went on an intense purge of everything that “pushed” at me: I stopped posting to Twitter 5–10 times a day and deleted Twitter, Facebook, and Swarm (sorry Foursquare!) from my phone entirely. I turning off all notifications (literally as many as I could figure out how to turn off). I unsubscribed from every email I was getting “just cause.” I removed myself from every RSS feed (yes, I use RSS) that was about tech, business, and politics (sorry outside world!). I stopped following all health and wellness sites (except Greatist, obviously). And doesn’t just feel good, it feels great. It even feels great just to write all that out! My mind is so much clearer, able to better focus on things that actually matter.

Focus is a secret super power. I don’t miss any distractions and I don’t miss anything important. I was addicted (FOMO!) to notifications about things that literally don’t matter and have no bearing on my life. Everything I really need to hear about, I still do. And of course there’s still value in unstructured exploration and Wikipedia rabbit holes (at least I think so) — I just adventure when I want to, not when someone else interrupts me and tells me to.

2. Making money is great.

Last year we went from just about zero dollars in revenue to profitable (well, a little over break-even) and it changed everything.

We accomplished this over 4.5 years with just a little over $3M raised. Then, in January we announced our Series A led by Floodgate and, though we’re well on our way to doubling in team size, if things go to plan we’ll be profitable again by the end of the year. Yay money!

I’ve always wanted to run lean and bootstrap-y, so we have.

I’ve always wanted to be in financial control of our future, so we are.

Given the type of company we are today (media) and the business model we have today (brand partnerships), this is the right strategic decision to build the best and biggest long-term company, not a compromise. Of course, this doesn’t apply to every company. But I’ve always felt the revenue-generating path was the right one, so I feel some validation now that making money is in vogue again. It was also a welcome surprise that the minute we were making real money, investors wanted to give us real money. Funny the way that works. Profitability even let us find an incredible, terrifically aligned investor in terms of both mission and strategic plan. When we didn’t need to raise, I got to choose which partner I wanted most.

As an aside, this year I also learned the value of hiring a full-time accountant. When our investors, CFO, and advisors all suggested it independently I decided it’d be worth looking into, at least, but wasn’t sure what an accountant would do all day. We hired a terrific senior accountant in January and she’s had far too much to do and been an extraordinary help. (Thanks Sabrina!) It’s not a sexy hire, maybe, but do it.

3. Successfully raising money means more stress, not less.

I know few companies that have had a more seamless and stress-free Series A fundraise than we did.

That’s maybe mostly due to how awesome Ann and Floodgate are. But it also helped that we didn’t “need” to raise, that we were making money, etc… I wasn’t perfect doing my first major raise, but I’d like to think I did okay and most importantly we did it right for Greatist — we have a terrific mission-aligned partner, we didn’t raise more than we needed, we didn’t raise at a crazy valuation that limits our future flexibility, and all the “little” things that matter to founders fell the right, fair way.

Great, right? But suddenly there was four times more money than I’ve ever seen in our bank account and, instead of breathing a sigh of relief and working up the courage to pay for the buffet at Golden Corral (real luxury, guys), I honestly can’t remember a time I’ve felt more stressed out and anxious.

There’s no real external pressure on me to “put the money to work” or triple revenue, just the opposite — everyone is pushing me to build the best long-term business without compromising culture or brand. But internally I feel more pressure than ever to make the most of the skills I’ve been gifted, the resources I’ve been granted, the team I’ve recruited. I feel more overwhelming responsibility to make good on the difference I set out to make with Greatist, the impact on the world it’s my life mission to achieve. I’ve never had more of a chance to do that and I’ve never felt less prepared and less worthy of the burden.

So my anxiety is unexpectedly through the freakin’ roof. Everything’s on track and things have never been better, but I feel more stressed out than ever. Maybe that makes me good at this, maybe that makes me bad. Maybe it’s about money being burned again, maybe it’s about my nightmare scenario of growing too fast — compromising brand and culture for short-term gains.

Whatever it is, people often warn that raising money can ironically come at a cost — so add stress and anxiety to that list, I guess.

4. Businesses built for the long-term win.

I’m consistently surprised (shocked, even) by how few founders I meet are purposefully and intentionally building long-term businesses.

It’s not my role to judge anyone else’s reasons for starting a company (it’s hard no matter what), but I just don’t get why anyone would want to put themselves through the excruciating journey of founding a business without deeply, profoundly wanting that business to last.

Every founder will say they’re passionate about what they’re building, but it’s too rare to find authentic passion and that just bums me out. It’s too rare to find people who genuinely care about building a special culture because they realize its importance in helping their company succeed. It’s too rare to find folks who really want to build billion dollar businesses (to really “to make investment decisions in light of long-term market leadership considerations”) and are crazy enough to believe they can do it.

Maybe it’s something to do with the market these past few years or with The Social Network (not kidding)? I don’t know. But even though that’s disappointing, this isn’t about comparison. After all, I only truly compete against is myself.

Five years ago I started Greatist explicitly because I wanted to build something that mattered, something that I’d wake up (yup!) five years into and be just as if not more excited about building and sharing it with the world. So far so good.

But I’ve spent a long time feeling shameful, almost apologizing for being a heart and vision-driven entrepreneur. But that’s bullshit and I’m done with it. I’m absolutely a heart-driven founder, building the company I most wished existed growing up and I’m most grateful exists today. There’s never been a brand in health that people love and trust because it’s really, truly on their side. It’s been too easy to make money in healthy the easy way — and that’s just super messed up. So, yeah, it’s my life mission to give everyone, everywhere a “health attitude” so they can find what’s good for them. Not just because I think that’s an awesome business opportunity, but also because I’m convinced that’s the only way for anyone to be succeed at being healthy long-term.

I hope Greatist is the platform with which we can make good on that mission. If not, it’ll be the next Greatist.

Anyway, I’m tired of pretending that I’m not this. I am.

5. Start recruiting way earlier.

People are everything, so there’s no doubt a CEO’s primary responsibility is building the best team.

At Greatist, we have no trouble convincing amazing folks to come work at Greatist — we’ve never been so truly a “rocket ship” with an incredible culture, special team, and important mission to boot. But the best people are rarely looking for jobs. They’re rarely motivated by money alone. They’ve often gone out of their way to find a great place to work already and they’ve been heads down working ever since. Long story short, it’s been almost unbelievably hard to find special talent.

I’ve recently heard more and more people say a CEO’s job is at least 50% recruiting, hiring, and retaining great people. And I’ve been trying to get there. We’ve been able to hire some really great people over the past few months (and already have really terrific people working for us, too!) — but most came through pre-existing relationships of mine or my team’s. In retrospect, I should have been doing a much better job the past few years at prioritizing getting to know great people just to get to know them and before we needed to hire so many of them (a number I know will only continue to grow). I wish I had been spending this much time recruiting before we needed it so badly!

Similarly, letting people go is a crucial part of growth. Sounds counterintuitive, of course, and it’s always unfortunate and tough, but being unafraid to fire someone when it’s the correct thing to do can come at enormous cost to the team, the culture, and the company. In fact, we’ve rarely let people go for not doing their job well — it’s most often been about great people no longer fitting with the team, evolving priorities on our end, and/or changing professional interests on theirs — so finding another opportunity is usually relatively quick (and we help if we can!). It’s never easy, though, to let someone go and even harder for managers to recognize its power for the first time. As I’m involved less and less with more and more team members, I’ve learned to be better at reminding my managers to remember that’s a tool they can use and encouraging them to use it if need be.

6. Being the “calmest person in the room” only gets more important — and harder.

As the company grows, things change. (Shocker, I know.)

I actually love the change, finding myself missing the “early days” little and instead relishing the challenge of each new stage more compelling.

Of course, my role as CEO role continues to evolve as well. The less I work directly with team members, the more careful I need to be in terms of what, where, and how I say things. I forget sometimes that I’m now just “the boss” to many of them, that they don’t know me or my style well enough to know quite what that offhanded comment, exasperated sigh, brief mention of a task I think needs more priority, or well-intended comment about a co-worker really means. When I say something, people take it super seriously! When I seem stressed, people worry! When I slack an innocuous suggestion, people drop everything else to put it into action!

In some ways, as the company grows, my latitude shrinks. I’m not surprised about all this, but didn’t expect (or maybe notice) the drastic change until recently. For one, this underscores the importance of having high-level senior leadership I trust to know me well enough (and sometimes translate what I meant to others). For two, this also emphasizes my continued journey to be the most stable and calm person in the room. Ultimately, I can’t forget how profoundly I set the tone for our organization. It’s humbling and even a little scary how big of an impact the energy I bring each day to work can have — this is both a burden and a great opportunity.

In the early days of Greatist, the team voted everyone a “superlative” of sorts — things like “the heart,” “the spirit,” “the spice.” I was voted “the energy” and was frankly disappointed — was that all I was to the team, I wondered? Isn’t a CEO and founder’s role bigger than that? Looking back, though, I totally get it — it’s less about my personal energy (I’ve got a lot of it) and more about the motivated but focused, adventurous but calm, optimistic but honest energy I try to bring to the team. And that energy has to continue to be authentic to me, not a mask or a front, or it simply falls flat.

I’m not always perfect (and have off days, too!), but I think overall my journey to be vulnerable, grateful, and present is well on its way.

7. Innovate or die.(Dramatic, I know.)

Walt Disney famously saw his theme park, Disneyland, as a place that would never be completed, one he could constantly continue to improve — and improve it he did. It’s a testament to his legacy that his company, Disney, continues that spirit through impressive (often ballsy) improvements — investing billions of dollars to acquire new IP, introduce digital payments via the MagicBand, and more. As many traditional media companies stumble and become irrelevant, Disney only seems to get better — and that’s in no small part because of its lack of fear to embrace new technology and try new things.

It only becomes clearer and clearer that if your company’s not on the cutting edge, you’re done. If innovation and taking risks isn’t built into your team’s DNA, fuggedaboutit. Every couple years at Greatist we’re suddenly behind again after feeling like we’re far ahead. And the speed of this acceleration is exponentially, not incrementally, increasing.

Looking back at Greatist’s history, there’s been at least three major times when we’ve had WFIO conversations — one year in when we realized we needed to focus on a niche demo (which led us to Pinterest), two and half years in when we realized writing great content wasn’t enough (which led us to hiring a mostly new editorial team that lived and breathed social), and three and a half years in when we realized I needed to sell brand partnerships to learn what worked and what didn’t myself (which led us to hiring the right sales team for the first time). Those WFIO conversations were humbling and hard, but not throwing in the towel enabled us to get ahead of the curve and resulted in our biggest periods of growth — finding (and nailing) Pinterest led us to breaking 3M unique visitors per month, our new editorial team led us to 10M uniques plus brand legitimacy, and our new sales team led us to a mostly profitable 2015. Isn’t it fascinating that moments of semi-crisis led to such big leaps forward?

I think in every case above it simply took (nearly) too long for me to identify what was up. It’s been hard for me to step outside of the day-to-day, yet working “on” the business and not “in” it is the only way to turn these challenges into opportunities. So I’m actively working harder (and hiring smarter) to get me closer to just being CEO. Similarly, being radically candid about what’s going on and coming up with innovative ideas can’t just be my job, so I’m also actively trying to find ways for every level of our team to think and act in more of the same way.

8. A company’s core values evolve and that’s a good thing.

Long ago during our founding I set forth our company values. Every person who’s started a job at Greatist has learned them and, I believe, lived them. They stemmed not only from what I thought this company should stand for, but also the early team we had put together. They were my first legitimate stab at creating a company’s core values and, frankly, they were good. They shaped who we hired, what we did, and how we worked. But as the company continued to grow, I felt more and more like we could do better. As we matured as an organization, I felt the words we used to capture our core values weren’t keep pace with our growth. So we set out to re-communicate what we stood for internally. Here’s what we did — first we held an open meeting where the whole team was invited to brainstorm things our culture stood for. We gathered these and more suggestions together, then I condensed all of them into loose categories. We then held another open meeting where the team ranked and rated the categories in terms of which resonated most. Then I spent a couple airplane trips working through each of them, naming and renaming, combining and de-coupling, and organizing and re-organizing before coming up with a first draft. I then gathered feedback from both our senior leadership and our most tenured team members, both inputs having a meaningful effect on the final stage. Then I purposefully let them sit for a few weeks, altering them just a touch before revealing them to everyone at our quarterly gretreat (that’s what we call our “retreats.”) In fact, we themed the whole retreat on values (personal and professional), bringing in outside facilitators and then (thanks to an idea from the amazing Amanda), we did an exercise where each team member brainstormed “behaviors” for each company core value and then, in groups, combined them into three representative behaviors. I’m very proud of the evolution of our core values and very proud of the thoughtful, collaborative process we took to get there. Most of all, I’m proud we embraced how our company values evolved — and weren’t afraid to update them in a way that feels even more true, instructive and inspiring, to what we’ve built.

For what it’s worth, I also spent a lot of time (prompted by our awesome Romena) creating my own core values. They’re courage, authenticity, play, disciple, and impact.

*9. Change in health isn’t coming — it’s here. (*Bonus lesson!)

Five years ago, I would have said we’re starting to see a profound shift in terms of how the world sees health.

Now everyone can see that change — you can see it in the announcements enormous food manufacturers, retailers, and restaurant chains have made (real food, not processed) and in the types of things celebrities swear they’re into now (juice cleanses, not binge drinking).

According to a recent study by The Cassandra Report, 73% of millennials would rather be “healthy” than “wealthy.” This stunning stat illustrates how dramatically our generation differs from generations in the past — healthy more than wealthy? Heck yeah!

When I started Greatist, I was afraid the healthy living brand that succeeds with millennials would be built for the wrong reasons. After all, it’s been tragically easy to succeed in health and wellness by doing it the “easy” way — selling products (or, worse, a lifestyle) full of empty promises and praying on people’s insecurities. I had no doubt society would be taking health exponentially more seriously — I just hoped they’d have a brand that helped them approach it in a healthy, long-term, sustainable way. That’s the very reason I started Greatist — partly because I was terrified someone else would build something that wasn’t actually on our side and partly based on the opportunity to positively shape how we get better.

There’s no doubt timing and luck play a very important role in a startup’s success, so I feel very lucky we’ve had some of both. I‘m also convinced we haven’t only been riding a wave, but also playing a pivotal role in shaping the wave.

As the wave continues to grow, however, we only have a bigger and bigger responsibility to harness it and keep it heading in the right direction. It’s a start, at least! I’ve learned a lot of things the hard way, but it’s nice to know I was at least right about the market timing. Now’s when it only gets even more important to take advantage of and bear the responsibility for the momentum.

I also learned couches are very expensive.

Year Four (read whole post here):

10. Beware the “trap of cool.”

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

12. Trust your gut.

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

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

15. Don’t disappear into the fire.

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

17. The importance of gratitude.

Year Three (read whole post here):

18. Hire slooow.

19. Fire fast (but with honesty and compassion).

20. Give people the keys, but don’t forget to ride shotgun with them every now and then.

21. It doesn’t get easier.

22. Don’t forget to be grateful for and celebrate the small wins.

23. Half-ass nothing. “Full-ass” everything!

24. It takes a lot longer than you think to really learn something.

25. You and your company are not the same thing. And that’s actually a really good thing for both you and your company.

Year Two (read whole post here):

26. A positive attitude can be unexpectedly powerful.

27. Hiring the best people takes building the best long-term relationships.

28. Do due diligence and then some.

29. Don’t get six-pack abs in six weeks.

30. Learn to get rid of all the stuff in your head so you can focus on the things that matter.

31. The difference between someone who’s good & someone who’s truly special is huge.

32. I’m not alone, even if it sure feels that way sometimes.

33. Passion FTW.

Year One (read the whole post here):

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

35. Sometimes you just have to make mistakes for yourself.

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

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

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

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

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

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