Monday, May 02, 2016

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 last week, and I read another powerful view from the trenches by Sarah Jane Coffey just a few days ago.  There's even a session during next month's Boulder Startup Week 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.

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.

Saturday, March 19, 2016

The Pizza Singularity is Upon Us

We interrupt your regularly scheduled Trump-related posts to remind you that the robots' incessant march toward global dominance continues. It's clear that this is their first step toward controlling the food chain, and they're starting with our most vulnerable population: stoners and college students. 

I find this sentence the most troubling:
It is not really clear how the cute-looking automaton would defend its precious cargo from glutton thieves or random troublemakers, but the company said in Facebook posts that it "will be taking every precaution necessary to ensure he is safe including surveillance and security etc.”

This clearly hints at a weaponized pizza delivery system which can be dual-purposed to hold customers hostage for tips or mental reconditioning. 

Don't be fooled by its cute shape and name, people! DRU is coming for you!

Thursday, February 25, 2016

45-year-old sighs tiredly at drama between 20- and 30-year-olds

I heard that there’s been some sort of kerfuffle in the millennial world about how old you have to be before you deserve a well-paid job. I’ll be honest: I just skimmed the articles because I don’t have that kind of time. I did read the headlines, though, and I noticed a definite pattern. so I guess it’s time for the 40-somethings to weigh in. Since most of us are too tired by the time we get home from work to write, I took the initiative and scientifically polled my peers on Facebook to get their reactions (for those of you who haven’t heard of it, Facebook is where old people go to share picture of their children. It’s like Snapchat, but you don’t have to screenshot the pictures if you want to look at them again).

The general consensus of the 40-somethings is: we can remember when we had enough energy to get this upset about other people’s opinions. Those were good times. We also stayed up later and drank more back then, so we had more time and incentive to share our opinions, whether you wanted to hear them or not. We’re also amused by the verb escalation as people “destroy,” “rip,” and “shred” each other’s arguments. We’re always up for a good “lambasting” or “shellacking” ourselves.
As near as I can tell, this conversation hinges on a simple question: when have you done enough that you deserve to be paid well, and how much of your personal history do you have to share to prove your point? After 20+ years in the work force, I can tell you that you’re asking the wrong question. It’s not about what you deserve, but what you deliver.

Life isn’t about getting what you deserve. The only place where people get what they deserve is in prison (most of the time) and on The Bachelor/Bachelorette. Those people deserve each other. If you’re waiting for your boss to give you what you deserve, you’re going to be waiting a long time, and when you do get it, you probably won’t like what you got. Work is about what you deliver, its worth, and what people will pay for it (which aren’t always the same things).

It all comes down to economics. Whether you’re working for yourself or for a massive corporation, you have to produce something that people want and are willing to pay for. Even an artist has to sell his paintings if he wants to eat. Whether or not you find that process fulfilling is up to you, as is your decision about how much unpleasantness you can bear as part of that process. And unless you want to become part of the “freegan” movement (or as we called it when we were in our 20s, “crackhouse squatting”), you can’t opt out of the process. You want to buy stuff? You need money. You want money? You’ll need to sell something, whether it’s your time or something you made.

I think everyone understands this (well, most everyone). What really seems to get our boxer briefs in a wad, though, is the value that we receive in this transaction. There’s a feeling that, “I should get more for what I’m doing, because I need more/want more/deserve more because I have a college education.” The problem is, that’s self-perceived value — you think your time is worth more than someone else does — and that’s not how this whole thing works, especially when you’re starting out. Entry-level jobs — or the jobs that we all get for the first 5 years or so of our careers — are a buyer’s market. The company has the money, you have the need, and you’re an unproven quantity. The realized value of your time is non-existent, because you’ve never done it before. Once you build up some equity by actually delivering value, you can close the gap between your self-perceived value and your realized value, and that’s when the market starts to shift. You have a product that people want to buy, and if you play your cards right, you can enter a seller’s market, where companies are bidding for you. 

There’s another factor to consider in this equation, and that’s your competition. If someone else is willing to do the same work for less than you are, then that’s the value of the work. I don’t care how polished the prose is in those Yelp blurbs you’re writing, or how expensive your English degree was (those are your supply expenses, not your employer’s). If there are 20 other people right down the street willing to do the job for $2 less an hour than you are, or a whole bunch of people across the globe who will do it for $2 an hour, then you’re in a commodity market. You need to find a way to create some unique value that only you can provide, and you won’t do that by proclaiming your specialness. Remember: it’s the deliverable, not the delivery person, that matters.

“But wait,” you say, “what about that 22-year-old who built a company and made millions of dollars in a couple of years? What makes him so special? Or what about that douchebag frat boy who made millions of dollars off of other people’s work?” Well, they managed to deliver value (or at least a perception of it) that a lot of people were willing to pay for. And one of them probably worked a lot harder than both of us for those few years, while the other one got what he deserved.

So, here’s a thought before I go back to my family: can we stop talking about what we deserve and start thinking about what we deliver? Let’s create some value instead of creating a fuss. When we stop worrying about how unique we are and start focusing on what we can uniquely bring to the market, that’s where real fun begins.

By the way, I hope this pattern continues. I can’t wait until a couple of weeks from now, when we get to hear what my grandmother thinks about this whole situation. I can hear her now: “What’s Medium, and what are all these kids yelling about?”

Sunday, December 27, 2015

So you've been invited to speak at Ignite...

A friend of mine was just invited to give an Ignite spark at a conference in San Jose.  She's an experienced speaker, but hasn't tried the Ignite format before.  Since I've spoken a few times at Ignite Boulder, she asked me if I had any tips.  It turns out I did.

So you've been chosen to speak at Ignite!  First of all, congratulations on your bravery!  This format makes seasoned speakers weak in the knees, so anyone who's willing to stand up there and bare their soul in 20 15-second chunks has my admiration (and my empathy).  It's the scariest, most fun public speaking experience you can have that doesn't involve tear gas.  Here are my tips for first time Igniters.

Know your main point before you start. You only have 20 slides, which isn't enough time to ramble, unless rambling *is* your point, in which case that's all you'll have time to do. When people talk about your talk, what do you want them to say? "Oh, right, that was the one about..."  And be prepared for the main thrust of the talk to change completely as you work on it.  Just as Michelangelo chipped away everything in the block of marble that didn't look like a woman, sometimes a new talk emerges as you work.  If it's good, go with it, but make sure to stay focused.  5 minutes.  That's it.

The geekier the better. Ignite is about passion and geekiness, and the best talks I've seen went deep on topics that I'd never known anything about before. One of my favorites of all time was from a woman who decided to knit a "weather scarf," that showed the average temperature in Boulder for an entire year, with one color-coded row per day. She walked through the problems she had to solve, from getting the data to building an app that could access a weather API to pull a year's worth of averages. It wasn't life-changing (unless you're also a weather obsessed knitter, I suppose) but it was funny, odd, and interesting all at once.

You can be inspirational, but don't try too hard. I've seen too many talks that went, "Here's this thing that I feel. Now go out and change the world!!!"  Meh.  I'm inspired by smart people's passion, not by generic rah-rah speeches.  Now, I have also heard powerful stories told from the Ignite stage, stories that packed a shocking amount of pathos and inspiration into only 5 minutes.  If you have one of those stories, then go for it: inspire us.  But if you don't, that's OK.  Rather than offering the verbal equivalent of an office motivational poster, teach us something fun and infect us with your passion.  That's far more memorable.

Likewise, humor is good, but this isn't standup. Don't let the laughs get in the way of the message. I try to have a sprinkling of jokes in my talks, but I'm up there to share something important to me while entertaining people. If you want to crack jokes for 5 minutes, try the open mic night at the bar down the street.  Same with language: keep it clean unless there's no other way to make your point. We had a talk earlier this year that was (intentionally) littered with F-bombs, and while it was clever, the speaker obscured an important message about getting involved in local politics behind the haze of cursing, and she got called out for it by people who disagreed with her.  One or two curse words can have a great impact, but if you don't need them, don't use them. Even if it's part of your daily vocabulary, it isn't for everyone, and some audience members will be distracted or turned off by excessive cursing.

Think about the "so what?"  I'm sure your talk is very interesting -- the organizers chose you out of a crowd of applicants, right? -- but people will hear 10-15 other talks that night. What makes yours stand out in the crowd? What's relevant to the audience, and what made you want to share it in the first place?  Why should they listen rather than heading to the bar or live tweeting their thoughts about the last talk?  Do you have a call to action? If you know why you wanted to share this idea, then make sure they do, too.

Tell stories. Our brains are wired to remember stories, not facts and opinions. If you can either open with a personal story or use one to illustrate your point, you'll have a much better chance of being remembered, because you'll be "the one where she..." rather than "the one with the compelling argument that I forgot by halfway through the next one." The most compelling talks I've ever seen were given by people sharing deeply personal stories and inviting us all to join them in learning from them.


Write it all out without worrying too much about time, then prune. As a general rule, you'll get 2-3 sentences per slide, so the total will be around 50 sentences (no run-ons). Aim for about that length, but don't worry about slide timing until later. In 2 out of 3 of my talks, I got completely stuck because I was worried about presenting ideas one slide at a time. I had to go back, ditch it all, and just write. Then, when I went back, the words started to line up with the slides.

Done pruning?  Great, now distill your speech down to its essence. You'll need space for breathing, laughs (hopefully), and reacting to what's going on around you, so you'll want the talk itself to run about 4:45. To get there, you'll need to cut your second-favorite joke, that clever little tangent, and the second point that seemed so brilliant when you came up with it in the middle of the night. Remember your point and get rid of anything that doesn't support it.

Structure: someone once told me to divide my talk into quarters, with 5 slides for an intro, 5 for expansion, 5 for supporting points, and 5 for conclusion and call to action. I'm too verbose for that, so I tend to go in thirds: 3-4 slides for intro, 10-12 for expansion of the argument, and 2-3 to wrap up. My most recent talk on faith was the most tightly structured that I've done, and that was how it came out. I've seen people play with the format, some more successfully than others, but I think either approach is a good starting point.

Slides: use pictures, not words. An Ignite talk comes at the audience quickly, and anything that divides their focus will dilute the impact. They only have 15 seconds to hear your point and scan the slide, so if you make them read then chances are that they'll do that instead of listening. A picture by itself or with a brief caption is ideal. If you have to use something more complex to support your point, then don't compete with it. Give the audience time to read it, then continue with your talk. I personally love to let my slides provide most of the humor. You can find pictures that either support what you're saying or subtly undercut it for humorous effect, which draws the audience in and lets them know that you aren't taking yourself too seriously. Key word: subtle. If you just put a hilarious picture on screen, then you're going to either disrupt your own talk while people laugh or you're going to have to step on the laughs, which discourages any more from coming.

Pro tip: if you have a slide that perfectly fits the point you're making, but your point is too long, you can "cheat" by using the same slide twice. It's a little distracting when the slide advances without changing, but only for a second, and it's better than racing to cram 30 seconds of thought into 15.

Practice.  A lot.  Being comfortable with your material gives you the ability to deal with the unexpected, whether it's an old version of your slide or a drunken heckler in the audience.  I like to practice my rough draft with a stopwatch first, to see how close I am to the right total time, then practice with my slides auto-advancing every 15 seconds.  Doing that helps you find the rhythm and see where you're rushing to get everything in before the next slide, places where your words don't have to synch up exactly, and moments where the timing is really critical (like when the next slide provides the punch line).  Learning where you have room and where you don't will make you more comfortable when you're live.  Unlike in other presentations where you have some control, those slides just keep moving, so you have to hang on for the ride.

Enjoy the adrenaline rush.  I've performed on stage and spoken in front of large crowds, but nothing gets my heart pounding like stepping onto the Ignite stage.  I think it has something to do with the suddenness of it: one minute, you're in the audience listening to someone else, then, 20 seconds later, you're on the stage speaking.  And did I mention that the slides don't wait if you aren't ready?  If you're like me, you'll be out of breath for the first couple of minutes, you'll enjoy the rest, and then you'll be exhausted.  Or, as my wife put it when someone asked her whether she enjoyed her first Ignite talk: "I'll let you know as soon as the nausea passes."

Good luck, and I'll be cheering for you from the bar.

Sunday, September 27, 2015

Video from Ignite Boulder 27: "The Search for Signs of Intelligent Faith"

Here's the video from my Ignite Boulder talk.  Enjoy!