Hold on to your why

Founders need to retain their own mission while they build out the company’s.

Photo by Sharon McCutcheon

Managing a high-growth company is the hardest thing I’ve ever done. One big reason is that I only received problems that no one else could figure out. Some were organizational problems that should naturally route to the CEO, but a lot were functional issues that I was no more capable of solving than anyone else.

I eventually discerned a repeated pattern in solving these problems. At first I would just get a few issues. I’d muddle through — do a bit of research, ask for help, and sort things out. As we grew, more and more of my time would be spent on this one kind of problem. I’d become better and better at handling it, and just about the time I’d start feeling like I knew what I was doing, I’d realize, “Oh: There are people out there who specialize in this”. I could just hire someone to do it full time, and they’d be better at it than I ever would. Duh.

I’d then spend three months, or six, or twelve, hiring for the role, and bam, suddenly my time is freed up and I’ve got an actual expert in charge. Well, kind of. At this point I’m a self-taught semi-expert who does not buy into the orthodoxy of the role, and we’ve got a year of my weird solutions, so there’s a lot of friction as we sort out just how to add this new skill set to a growing org. But the point is, my time spent on this problem drops precipitously, and I no longer have much opportunity to put my new-found skills into practice.

Usually just in time for something new to come into focus.

This pattern — gain just enough expertise to hire someone — played out again and again, for me and for other founders I’ve talked to.

In some ways it’s thrilling. You get experience with all of the key areas at the company, and you’re always learning something new.

In other ways, though, it is soul-crushing. Over the eight years I managed Puppet while in fast hiring mode, I rarely got to spend time doing anything I was good at. Humans have a psychological need to feel competent, to feel like they are in control and know what’s going on. I don’t need this all the time, but please, just a little? Sometimes? Nope. Pretty much the second I started to feel like I understood something, I had to hire for it, and my problem changed from doing to managing.

After years of this, I knew just enough about everything to suck at it, but not enough to actually be useful to anyone.

Only as my tenure as CEO came to a close did I begin to see what I uniquely added to the organization. I began being comfortable not delegating certain problems, and felt justified in spending hours on something as an individual contributor, rather than seeking leverage in everything I did.

Only once this happened did I start to feel comfortable as a CEO. I wasn’t just routing problems, I was actually solving some of them. I was not spending 100% of my time in areas I was incompetent; just most of it.

I know the advice as well as you: Great leaders delegate, they empower. If you’re doing the work yourself, you’re not a real leader.

Bullshit.

Yes, building and running a team absolutely requires that you empower the team. But that doesn’t mean you don’t get to do anything yourself, that you hand everything off and have nothing left.

Just like everyone else, you, too, need a reason to show up, to stay engaged. You have to hold on to your own why.

If you don’t remember why you, personally, are in the job, then you’ll look up in a few years and realize it’s not there any more. You’ve moved too far from what gets you up in the morning, and suddenly you can’t do it. Or worse, the company has developed but you haven’t. You’re no better at the thing you want to master than you were when you started, because you haven’t been spending time on the problems you care most about.

Some of this is that you need a place of safety. I am a highly fireable person, and raising venture capital made for downright tenuous tenure. The less confident I was about my own strengths, my own value, the less safe I felt. And humans need to feel safe to do great work.

More than that, though, I needed a platform for learning. I was pursuing mastery, but of what, exactly? Of not mastering things?

I know other leaders really are master delegators, hirers, organizers, etc. But that was never going to be me.

I had to peel things back, really understand why I was there, what I cared about, what I wanted to be the best in the world at. And, really, what I was good enough at that I ended up in this place, running this company. Then, as the problems rolled by, I could be sure to push that forward just a little bit, even if my focus was on the organization’s needs, not my own.

The times I lost this sense of why I was there and what I was getting better at were some of my most depressing days. But the days where I could connect what I felt good at, what I spent my time on, and what the company needed from me were the best days.

I don’t think that’s any different for me, or for other founders, than it is for anyone else.

But all the discussions of leadership I hear leave this bit out: You’re a human, too. You have to provide the why for the whole organization, but every individual deserves to be able to translate that into what they do every day. Even you.

Owning My Strava Ride

I know what it means to own my code contributions Github, but what does it mean to own my rides on Strava?

Photo by William Hook

I recently went mountain biking in Bend, Oregon, which is a few hours’ drive from my house. As I usually do, I used Strava to record the ride. This was a new trail for me, and I got lost multiple times, so I also used Trailforks to figure out how to get back to my vehicle.

I’ve been thinking a lot about how services like Facebook start out helping us, but at some point the relationship shifts and we’re stuck helping them more. I don’t think Strava has gotten to a stage where the relationship is abusive, and maybe this is weird but I hope they stay too small to ever get there. Even without that shift, though, I am a little uncomfortable with our relationship.

I was standing on the trail, trying to find the right trail and idly watching a coyote search for chipmunks. As I switched between apps, I realized that I was losing a lot by recording in Strava instead of Trailforks. Or rather, I wasn’t; people who want to bike this trail in Bend were.

I log my rides (and my infrequent, hilariously slow runs) in Strava for, um, reasons. I don’t want kudos, and I don’t really look at my historical performance, although I do enjoy being able to study my rides at times. I want the data there, even if I rarely use it. And it conveniently automatically completes my daily exercise goal in Streaks. It’s kind of useful, but if it went away tomorrow, I wouldn’t miss the online component much, if at all.

If I instead recorded all of the trail rides in Trailforks, then everyone who came after me could get some value from the information provided by my ride. They could see what route I took, could likely tell based on my speed when I had to walk and when I was able to ride, and they could over time get a sense of what routes are most popular, or even what signage is confusing.

I built an open source company, so I’ve thought a lot about the worth of contributions. A developer‘s time on one project can’t be spent on another. Someone who writes documentation for your baby is giving up the opportunity to contribute elsewhere. It’s a conscious choice on the part of the contributor, and a constant interaction between the project and its constituents to keep people coming back.

I think Trailforks really understands the value of my contributions: If you do this, people who ride here will have higher quality data, and probably better rides.

I am super confident that Strava knows the value of my usage: I’ll get feedback from friends and I can track my speeds and feeds. But those aren’t contributions; that’s not something I’m giving up for the greater good. It’s something I am doing for selfish reasons.

The value of my trail ride could be for the greater good, though. Even my road rides and runs could be, as they could help people find routes, but the trail rides especially seem valuable, because the downsides of being lost out there are materially worse than not having the right route for your run.

It’s clear to me that Strava is not seeing my data as a contribution. They’re focused on engagement. That’s not inherently bad — lots of people use and love the app — but it is different. I find it interesting to think of what the experience would look like if that changed.

But after that, I thought: Why can’t I just share the data with both apps?

I mean, to some extent I can. I can just run both of them and let each record its own view of the world. This is what I did with Slopes and Strava in Mammoth, taking the lifts up and riding down. That made a little more sense because neither quite has the correct view of the world — Slopes doesn’t know what bikes are, and Strava doesn’t know what lifts are. It was pretty kludgy, but more importantly, I didn’t run into this conflict because the apps exist to do pretty much the same thing, just for different sports.

I could duplicate here, I assume, but… it seems stupid.

Beyond our relationships to service providers, I’ve been thinking about what it means to own your own data. It sounds awesome, but it’s rarely very useful in practice.

It turns out, I do own the data that I have posted on Strava. Great! So I’ll just share it with Trailforks, too.

Hmm. What would that look like? Can I… download the data, and then upload it to Trailforks? Is it a common data type?

Can I record it separately on my phone and post it to both apps? Is that what truly owning my data would look like?

It’s hard to imagine that world: You use apps that generate data, which by default is yours and only yours. It gets recorded in forms that are easy to share, understand, and manage. If you like, you can then contribute that data to other sites, and in doing so, you get to negotiate with them exactly what rights you’re passing on. Either way you have the data, but now they get a copy, too. If you don’t like their offer, you still get the data, and most likely, given you have all your delicious data, other apps will crop up with a different offer, because they can focus on that rather than all the data collection.

It would look a lot like the text editor I’m using to write this article, Ulysses. It allows me to publish, but is built first and foremost to make it easy to write. Sharing, contributing, engagement, and all of the other online stuff is left to other sites, other apps, like WordPress and Medium. And yeah, those apps do allow both writing and publishing, but it’s a horrible experience, a great way to lose data, and if you only write there then your data is stuck in their system and is pretty hard to get out in a useful way.

The world of writing looks weirdly different from the world of recording rides. And a lot worse.

I’m not in control. Legally I own the data, but, ah, I don’t have it. Strava does.

I would never write directly in Medium, so why am I logging my rides directly in Strava? What am I giving up because of it?

I’m pleased to find that Strava will allow me to give other people the data — the data that I own! — and it turns out that Trailforks knows how to slurp it out of Strava.

So it all ends well: My rides are in both locations, and every mountain bike ride I post to Strava will now be automatically imported intro Trailforks. Probably.

But for that brief moment, in Bend, while watching the coyote… I saw what it would take for me to really own my data. I liked it a lot.

How to Neg a Founder

Is that a compliment, or an insult?

Photo by John Salvino

My experience growing and fundraising for Puppet was full of inspirational-sounding phrases that cut like a knife. Aggressive goals got praise for wanting to “build a real product” and “really scale this thing.” These are some of my favorites. And when I say “favorites,” what I mean is, I hate them. Deeply.

The one that I heard most often made me want to walk out of the room. I’d pitch an investor while fundraising, and he (always he) would say: “So you’re going to try to turn this into a real company, eh?” As if being my full time job for years was somehow not real. As if you are the arbiter of truth, not my customers. Or me.

If you want to make an entrepreneur feel small, you really want to piss them off, try to inspire them this way. I assume most people who used it thought they were complimenting me, impressed that I was taking this big step or something. But it was a sure fire way to trigger my defenses. When you diminish the work I’ve done so far, it’s hard to see you as a potential partner. I quit my full time job five years ago, and have missed out on hundreds of thousands of dollars of earnings, but asking you for money is what shows I’m serious?

I’m convinced at least some investors did it on purpose, as a form of negging — trying to position themselves as an authority and me as someone who needed their help and wisdom. “That’s pretty cute. Why don’t you get some help from the professionals?” I’m good, thanks.

I know most people didn’t mean it that way, though. Their worldview is just so skewed that if you haven’t raised a ton of money, you’re not really trying. They can only conceive of success if it looks a specific way. You literally cannot succeed unless you do what they do, what all their friends do.

If you’re an investor, advisor, or executive, take a deep look at how you talk to founders. Are you truly complimenting them, or actually diminishing their work? Are you presenting yourself as the arbiter of success, even while you think you’re saying the other person has done so well?

If you’re a founder, know that you don’t have to take it. No one else gets to define success for you. There’s always an in-crowd, but by definition the best results come from being outside of it. Even if you decide you need their money, you don’t have to accept their framing.