Hacking the startup life


The founder of the first software company that I worked for put his head through a wall. He was upset about someone leaving, but you know, it was a wall. And his head, which was arguably the most important asset in the company’s portfolio.

At that same company, I had to break up a fight between two designers who couldn’t agree on a page layout. I had to pick one of them up and carry him out of the room until he could cool off. Fortunately, his hair was in a ponytail that day or I might have suffocated.

At another company, one of my standard interview questions for potential managers was, “What will you do the first time that someone comes into your office and bursts into tears?” My favorite answer, after a thoughtful pause was, “Well… first I would offer them a tissue.”

After 20 years working in technology startups, I know I’m not the only person who watches HBO’s Silicon Valley and thinks, “Wow, they’re really toning it down for the masses!” Startup life is hard and a little crazy. We tech people, as a rule, bring our own crazy to the office party. Put these things together and you have a volatile mixture. Blend in long hours, high stakes, and a general sense that there are always too many bases to cover, and it’s no wonder that people lose it once in a while. Of course, it’s only a short trip from “once in a while” to “every day, twice on Fridays.”


There’s a conversation going on about mental health and burnout in startups, and we need to keep it going. My friend Dave Mayer shared some of his own experiences as a founder and friend of founders, and I read another powerful view from the trenches by Sarah Jane Coffey last year. There have even been sessions during Boulder and Denver Startup Weeks dedicated to this important topic.

We tend to glamorize the startup life as a place where brilliant, dedicated, and — most of all — energetic people are changing the world, making it a better place and making their first millions in the process. We are the engine of the economy, the force of innovation, the ones who keep America from falling behind the other superpowers through the sheer power of our brilliance and the sweat of our furrowed brows. We tell each other things like, “I wanted to work somewhere that I knew I could make an impact,” and “I don’t want to be a corporate drone, sitting in meetings all day.” We don’t meet, we scrum! We don’t just write code, we sprint! We work all day, take a short keg break on our rooftop deck, and then we work all night, with the occasional foosball game to keep our reflexes sharp and aggravate our carpal tunnel. Who wouldn’t want to be part of that? Corporate drones, that’s who!

But there’s a dark side to startup life. Yes, you have a greater impact when you’re one of ten people in the company, but those ten people are usually trying to do the work of 30, so you do the math. You’re never bored, but you’re never offline, either. Office perks are fun until you realize that you can never leave, and it turns out that “dedication” and “passion” can quickly become presenteeism and a grinding competition over “who wants it more.” But on the bright side, the stock options are generous!

The problem for leaders is that these changes usually happen when we aren’t looking. The excitement that you feel for your market-beating/world-changing idea masks the little problems until they become crises. You look around at the tired faces of your team and think, “We’re just in crunch time right now. After this push, we can relax.” But this little push is followed by another little push, and then you land your first big customer and they need “a few small enhancements” to make the product work for them, and then there’s the release for the big industry event, and then you find out that you have competitors…. There are blogs to write about your development philosophy and Medium posts to show how awesome your company culture is. Pretty soon, the rooftop deck is covered with snow and you’re explaining to your wife that you just have to do a little bit of work on Christmas to make sure that the release is ready by the first of the year. Meanwhile, the other startup founders you know are bragging about being able to get by on 3–4 hours of sleep a night, and you start to wonder about how to quantify the Sleep Gap as a measure of your company’s competitiveness. When people quit, they tell you that it’s not because they’re unhappy; they just got another offer that was too good to pass up. You notice that the foosball table is pretty quiet these days, but you don’t hear the grumbling that’s replaced it.

The startup monster will eat everything you put within its reach, including your free time, your health, and your family. As leaders, it’s our job to fence it in and protect both our teams and ourselves.

The startup monster will eat everything you put within its reach, including your free time, your health, and your family. As leaders, it’s our job to fence it in and protect both our teams and ourselves.So how do we do this? There’s always more work to be done, and for every triumphant cry of “inbox zero!” there are a thousand whimpers of “I’ll never get through all of this.” The startup employee who leaves at the end of the day thinking, “I have nothing left on my to-do list” either isn’t paying attention or was just laid off.

So here’s a thought: stop trying to get to the bottom of the pile. One of the worst mistakes that startups make is that they grossly undervalue their own time. Instead, acknowledge that time is a valuable and limited resource and decide how you’re going to invest it. Start saying, “we’re not going to do that right now,” and keep saying it until you find the most important items, then do them. There are probably a few items on your team’s to-do list (and your own) that you can quickly knock off, but this quickly gets difficult as you’re forced to make tradeoffs and give up things that feel really important. Remember, though, that the most successful startups are those that ruthlessly focused on a single goal until they were big enough to diversify. An unfocused startup is one bad decision away from a death spiral. So, focus. Ruthlessly. If that email, phone call, or feature idea doesn’t move your company definitively towards its goal, then it can wait, maybe forever.

Of course, in order to do this, you need to know what that one goal is. You do know what your company’s one goal is, right? If not, stop what you’re doing right now and go find a quiet corner, a mountain cabin, or a dark closet where you can put a towel over your head, and stay there until you do. Until you know why you’re in business and can clearly articulate that vision, you’re going to do more damage than any competitor could possibly do, chasing after bad revenue, distracting your team with useless projects, and generally diluting your valuable efforts. The biggest complaint that I hear from front-line people in startups is “Management doesn’t know what they’re doing.” The key words to note in that sentence are management and doesn’t know. When you start wandering all over the landscape in search of a purpose, you stop being a leader and you become “management.” Find your vision. Test it. Cling to it. Defend it like a loved one, and don’t let anything, even the lure of side money, pull you away. Even if you decide that you need to pivot that vision, do it purposefully and completely. Charlie Brown can be wishy-washy; you can’t if you expect people to follow you.


Setting the proper boundaries is also about more than good intentions and cleverly worded vacation policies (“take what you need, don’t be a dick” is my favorite so far). If you want your team to be healthy, you have to lead by example. I once had a boss who always made sure that he had the first email in everyone’s inbox every morning and the last one every night. If anyone tried to reply, he would send another response, and another, and another, until the conversation petered out in the wee hours of the morning. He wasn’t inspiring us with his work ethic; he was marking his territory, peeing on everyone’s inbox every day to remind us who was top dog. Unsurprisingly, he also spent a lot of time talking about the level of commitment required to make the company successful. We had a lot of turnover at that company.

On the other hand, the kindest words I ever received from a boss came when I was working late and he walked by my desk on his way home. He stopped, stuck his head around the corner, and said, “I love you. Go home.” For the little worker bee me, that was a freeing moment. With five words, he simultaneously recognized my effort and freed me from defining myself solely by it. When he turned and walked out the door a moment later, he set a healthy example as well.

We need to do more than talk about work/life balance: we need to model it. In my experience, “we work hard and we play hard” really translates into:

  1. We work hard and we have a ping pong table that everyone’s afraid to use, or
  2. We work hard, drink hard, and code drunk.

How about a new mantra: We work hard, get stuff done, and go home.

Working in a startup shouldn’t feel like an extension of dorm life: it’s healthy to take breaks and explore other interests with people who aren’t paid to be near you. Late nights and weekend work are occasionally inevitable in every startup, especially in software, where major releases and critical commitments inevitably create a last-minute crunch. But when this becomes the norm, you’re heading down a bad road. If the gas pedal’s already to the floor, you have no way to get more speed when the real crunch time comes. Plus, having a happy, supportive family life greatly reduces stress and burnout. The thing is, your family has to recognize you before they can support you.

Finally, in order to do all of these things, a startup needs leaders who understand people and what motivates them. Investors look at founders’ technical experience, industry knowledge, and business acumen, but too often they forget to ask whether these founders are capable of building and retaining a great team to bring their idea to life. It’s impossible to build the next killer app if you keep killing your team’s motivation with blockheaded management decisions.

Look around your leadership team. You probably have the business person, the sales person, and the technical person, but who’s the people person? Who among your executives is specifically charged with making sure that the rest of the company moves with purpose and vision? Who has actually built a high-performing team before? Who knows what to do the first time someone bursts into tears in their office? You need one of these, and no, that’s not HR’s job. HR’s job is to keep you from being sued when one of your executives inevitably says something dumb that offends someone. This is a job for your core leadership team. Motivating and caring for your people is as critical to your success as any patent or proprietary technology, because, let’s face it: for most technology companies, our people are our competitive advantage. They’re also our most expensive assets. As the cost of hardware and infrastructure continues to drop through virtualization and distributed computing, we’ve reached the point where replacing an engineer is more expensive than replacing a server. If you can’t find any other reason to protect your people from burnout, at least consider it a prudent financial move. You have a CEO, a CFO, and a CTO. Who’s your Chief People Officer?

The startup life is great. You get to wake up every day feeling like you’re changing the world for the better, or at least building a killer product that will have the world beating a path to your door. You get to have a say in the company direction and have beers with the CEO, all while wearing jeans and a T-shirt. You get to use phrases like, “killing it,” “secret sauce,” and “industry disruption” with perfect seriousness, even after the third beer. You also have a chance to make a genuine difference in the lives of others, even if that impact is limited to the people you work with.

We can do better at this. We need to do better, by recognizing our shortcomings and refusing to let our enthusiasm overshadow our better judgment. We need to recognize that, in this case, passion and ingenuity aren’t enough. They need to be accompanied by vision, focus, and empathy. We need to make our people part of our investment plan and be careful not to burn them out in our race for greatness. In short, we need to do more than build better products.

We need to build better startups.