Paul Rosania

Hi! I'm Paul. I work at Slack.
You should follow me at @ptr.
I can also be reached at paul@rosania.org.

The Arena

June 11, 2015

I've been reading a lot about World War II recently. The most surprising thing, for me, is how different the Allied experience was from the pop culture fairy tale.

As Americans, we grow up learning about Normandy, the Bulge, and the decline and fall of Germany. But we rarely learn about the war in North Africa and the invasion of Italy, and all the brutal mistakes and hardship America went through as we learned how to wage effective war against a brutal enemy.

In the Battle of Kasserine Pass, Eisenhower was so thoroughly routed by Rommel that America faced the real possibility of being pushed out of Tunisia altogether. A year later, the Allied invasion of Italy almost failed under German counterattack. Between these moments, the Allies made many other mistakes and suffered many minor defeats. Such is life in war.

And yet, history is written by the victors. Years later, having won the war, these setbacks are a footnote, rarely spoken of and never taught. Eisenhower was an American hero in 1945, but in 1943 that outcome was far from certain.

Running a business is nothing like going to war. But there is a parallel, I think, in how we write our history books, and how we evaluate our leaders. Facing adversity, we seek the fairy tale — gallant leaders, faultless, leading companies to infinite victory in weeks' time against any odds. We forget that struggle is part of the narrative.

I have had the great fortune to work for a handful of leaders who charge willingly into the most challenging situations, who inspire in the face of doubt and keep their teams grounded and humble about success. These leaders expect hurdles on the path to victory, and accept the criticism and vilification they receive from spectators on the sidelines.

I lost one of those leaders today, and I hope he will be remembered for the progress he made toward victory, not the inevitable challenges along the way.

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.

Thanks, Dick.

The Slow Death of the Young Entrepreneur

August 07, 2013

I wrote this essay in October of 2011. At the time, the emotions were too raw for me to share it beyond close family. As I approach 30, I'm releasing it in the hope that it's helpful to anyone going through this strange and bewildering transition.

On August 28th, 2011 I celebrated my 28th birthday. There was not much fanfare.

Two months later, I find myself unable to sleep. I stare at the ceiling while my mind races. I toss and turn during the night. I snooze my alarm until the last possible second. When I'm not working, my mind is racing with questions, like: What am I doing here? Am I on track? Are my life goals realistic? Does my perception of my self match up with reality? Am I too ambitious? Am I working hard enough? Too hard? I've begun to wonder: am I running out of time?

When I was younger, I thought of my life in stages:

  1. Work your ass off for someone else, learn. (Age 22-27)
  2. Start your own company, work your ass off, get your "fuck you" money. (Age 28-32)
  3. Relax a little. Travel. Get married. Get back in shape. (Age 33-34)
  4. Start a family. Work hard, but for a stable number of hours. (Age 35+)

Today, I'm still clinging to an ambitious set of personal goals:

  • Become an expert engineer
  • Lead a startup to marketplace success
  • Live a healthy lifestyle and get fit
  • Earn financial freedom
  • Build a family
  • Travel

And yet, despite my best efforts, here's how "the plan" has actually played out:

  • Age 22-23: Worked my ass off for a failing startup, had no idea what I was doing, learned a ton.
  • Age 24: Met a wonderful girl (and stupidly worried that it was way too early for "the plan.")
  • Age 25-27: Started a company, worked my ass off, had no idea what I was doing, learned a ton.
  • Age 28: Working my ass off for a startup that has real traction!

You could say I've wandered a bit. Still, I'm not that far off from where I thought I'd be. So why is my subconscious torturing me at night? It turns out, I'm learning a lot of scary things as I get older:

  • Planning for things doesn't make them happen.
  • Your body will deteriorate faster than you think.
  • Life doesn't wait for you.
  • The decisions you face get harder to make.

I find myself fighting these lessons, even as I begin to accept they are facts of life. The rest of this essay is an attempt to make sense of these things. These are deeply personal reflections. They may not apply to you, and I won't be insulted if you stop reading right here. I tell these stories mostly as an act of catharsis.

Planning for things doesn't make them happen

My life has taken a meandering path. Part of that is the pure randomness of events. The rest, I'm beginning to realize, is because I do not know myself nearly as well as I've always pretended. When my first startup failed, I had no savings, and I took a corporate job instead of staying in the startup space. I rationalized it as the only logical choice, and a temporary decision while I got my feet below me. It took 2.5 years and acceptance into an accelerator to get me out the door again. During that time, in my head, I was just biding my time until it was the right moment to jump back into the startup world.

Years can pass while you wait for the right moment for something. In grade school and college, I became too accustomed to being on a "track," knowing that if I followed it dutifully and excelled at every juncture, things would work out on their own. It took me 5 years of professional development to realize that following the obvious path was leading me toward a successful but uninteresting career. Quitting my job to start a startup was like ripping off a bandaid. Painful (scary even!) but worth it. Despite the company not working out, I've taken back control of my career progression, and I'm doing what I love.

Your body will deteriorate faster than you think

I graduated high school in 2001 a member of the varsity track and field team. In college, I let go. By the time graduation rolled around, I had no exercise routine at all, and from September of 2005 until November of 2010 I ran a combined total of 10 miles. (That's five years!) When I got back on the treadmill for the first time, running a single mile was so difficult that I had to use the stationary bike for a month instead, until my circulatory system could adapt to the elevated heart rate, and my knees to the constant pounding.

That experience was like a spiritual awakening. Instantly, exercise was a priority for me. I realized that if I didn't push to get in shape right away despite the tremendous difficulty, I might possibly reach a point where the pain was too great and the slow progress too discouraging. How hard would things be at 35, if they were this hard at 27?

Luckily I persisted, but it was my first glimpse at mortality. If I want to throw a football with my kids or chase my grandchildren in the yard, I need to invest in exercise every week for the rest of my life.

Life doesn't wait for you

On June 20th, 2007 I told a friend I'd be his wingman on a group date with his new girlfriend and her friends. We went bowling at Jillian's, a Boston mainstay. I bowled a 60, for which one of the girls teased me incessantly. Despite the abuse, I asked her out and we've been dating since.

I wasn't ready for a long term relationship when I was 24. In my mind, I had another 5 solid years of bachelordom and hard work before I'd even have to think about settling down and making time for romantic dinners and movie nights.

I worried a lot about fucking up the plan. After all, I had read so much about how family and startups don't mix, and how long nights at the office take their toll on relationships. My advice: don't heed that shit, trust your heart. My girlfriend has been the most stable, consistently supportive person in my life.

The decisions you face get harder to make

When my startup unwound early this year, my girlfriend was deciding on PhD programs. (She's getting a Clinical Psychology degree.) Thinking it would be a clean slate, something new and interesting, she picked a school in Chicago and we agreed to move there together.

Two months later I got an email out of the blue from an entrepreneur whose blog I've read extensively, someone I deeply respect. The email led to a call, which led to a series of interviews and a job offer: in Palo Alto, California. Amazingly, my girlfriend thought I should do it, and I ultimately did. It was the hardest decision of my life.

I'm not sure if I made the right choice. I think about it all the time. But the choice itself is not the point. More important is the weight the decision carries. As you get older, decisions involve more tradeoffs. As I lie awake at night, I worry about the even heavier tradeoffs you have to make when you're choosing between your career and spending time with your wife and kids.

So am I running out of time?

Yes and no. Maybe. Sort of. According to my life plan, I have 5 more years of hard work before it's time to settle down. That means I'm more than half done with the "glory" phase of my life.

Life doesn't play out sequentially. I fear the effect of family on my freedom and desire to work marathon hours. I'm afraid of competition from younger startupers, unburdened by the complex aspects of later adult life. I worry that once the personal burdens grow, my aspirations will become impossible.

And yet, despite my singular focus on my professional life while I was young, my personal life advanced. When family comes along, I maintain hope that the reverse will be true. Life is a balancing act. I may never achieve "the plan", but in a sense I've let go of that goal. I have a better understanding of myself and a more profound appreciation for the shortness of life. (As much as one can at 28!) I haven't squashed the fear, but I'm not totally sure I want to do that. Instead, I'm channeling it into my days. It gives me a drive, and purpose.

Thanks for reading.


Does this describe you? Have you had similar feelings or struggles? You can reach me at @ptr or paul@rosania.org. I'd love to hear from you.

A/B Testing Will Save Your Career

July 21, 2012

A company is the sum of hundreds of decisions made daily about product, marketing, hiring, etc. The magnitude of each decision varies, but it's rare to find one decision (or several) that is single-handedly responsible for your business' success or failure. What matters is the average: on the whole, does your business get more decisions right than wrong?

It's tempting to conclude that the best company is the one whose people have the best natural intuition. These people, blessed with divine judgment, will carve market-winning products directly out of stone, while their competitors misfire and fall behind.

In such a scenario, people with below-average intuition must be ruthlessly culled in order to maintain above-market performance. As an employee of this company, each decision you make carries the weight of your future career on its shoulders. (Better not fuck up!)

And yet, we all know intuition is fallible, mistakes inevitable. So how do you chart success for your career?

One option is to be lucky. (If you're lucky, you can stop reading here.)

Another option is to embrace A/B testing. A/B testing directs the conversation away from luck and intuition, and toward data-driven learning. In an A/B testing culture, your intuition is not your most prized asset. Rather, your value comes from your ability to brainstorm, define and execute experiments. Instead of focusing on being right, and approaching decisions with dread, you can focus on learning as much as possible by rapidly exploring different solutions to the areas of your business and product you are working on.

One benefit of A/B testing is never making decisions that are quantitatively poor. But there's a long term benefit as well: A/B testing focuses you and your team on the process of learning and building organizational intuition. It enables people to propose ideas that may sound silly or dumb without fear of retribution. And it enables people to gracefully accept defeat when their ideas are rejected by data. The company benefits greatly, as everyone iterates and learns more quickly.

As an individual contributor, you are ultimately judged by your impact. If you use your own judgment to make decisions, you will be graded on your intuition. But if you focus on learning via testing, you will be graded not on intuition, but by the velocity of your experimentation. Unless you're lucky, testing affords you much more control of the outcome.

Quora: What's the right time to create a growth team?

June 30, 2012

My answer:

[...] Growth engineering is about consistent small gains, with some big wins mixed in for good effect. To achieve this is a matter of patience, discipline and a keen (but flexible) understanding of your product and market. When you've achieved product/market fit, you know why, and you have a stream of data to work with, you're ready.

More at Facebook: What is the "right" time in a company's lifecycle to create a growth team?.

Tackling Hard Problems

March 27, 2012

The point is to be aware. If you find yourself resisting an obvious step due to an irrational fear, step back and force yourself to push onward. You only need to be right 1% of the time.

The Psychology of Tackling Hard Problems, by David Valdman