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.

The Morality of a Good Tool

Tools just get the job done, but products demand something in return

Photo by Todd Quackenbush

I love tools, the effortless balance of a well-known hammer in my hands, knowing exactly how to hold it and what it will do. Starting out clumsy is never fun, especially with the tools that crush fingers or spill, but I adore that feeling of developing expertise. It’s hard to conceive of a tool without also thinking of the experts who use it. I secretly wonder if I deserve most of the tools I have.

“That’s a mighty fine hammer you have there, but unless you can show me the callouses from using it, we’re going to have to confiscate it.” Home Depot would make a lot less money if we had to prove we got good usage out of the fancy stuff we buy.

This mythical tester doesn’t have to stick to checking you out. The tools themselves prove it when they’re not just for show. Knives shrink with sharpening, work pants thin, machines drink oil.

This is a feature. Preciousness is the antithesis of a good tool. “That knife is too expensive to use every day.” Ugh. Not my tools. I’d rather break something on the first day than be afraid to use it in real life.

Tools should be scratched. Dented. Aged. Their callouses should pair yours. You and your friends should huddle around your tools, bragging about whose has the better patina. Precious tools are just toys, decoration. They live on a shelf, or more often in the attic, not on your work bench, by your side. In software form, they are so well designed they don’t even function.

Tools only deserve the label if they help you work. Given that that’s the heart of what motivates me, it’s natural I want to build tools. I’ve been madly rushing toward a plan to do so, but was recently pulled up short by a simple question: What do you mean by tools?

I really hate the easy questions.

This was put to me by Jordan Hayles of the Radical Brand Lab. The bit above is one kind of answer, but as I thought about it, it became clear that it’s insufficient.

I’ve been saying I want to build power tools for people. Why not power products? That’s a motor boat of alliteration: ‘power products for people.’ Awesome, right? Right?

Ok, maybe not.

Part of my choice of phrase is that I grew up building houses, and ‘power tools’ just meant the things you plugged in. You know? Because they needed power? It’s a common usage, maybe my word choice here did not mean much.

Except… I’ve spent more than a decade learning product management, describing myself as a product-oriented founder, managing that function in a growing company, and attempting to teach it to other founders. Just a few more years and I might have some clue what I’m doing. Yet here I am ignoring both the term and the field entirely. Why am I so quickly dumping my work of the last ten years? Is it just creative branding, getting that blue color shine? Mere cynicism about the software industry?

Product management as we know it began in the consumer goods industry. You’re handed a train car full of dish soap and told to sell it. I mean, not all at once. You’ve got to package it, price it, convince a local store to carry it, argue with them about location, move it away from competitors, all that. Every product you see in your local grocery store is loved by a product manager who fights for its shelf space, believes it is beautiful, and wants you to give it a good home.

Tide soap is one of the most commonly stolen items, but not because it’s soap. The strong brand makes it easy to sell, even allowing it to be used as a stand-in for money in drug deals. Shows just how far I have to go in product management. Unfortunately, it says nothing about the soap.

Inkjet printers are an example of this gone wrong. Laser printers, their predecessors, had toner cartridges you could refill. Not very clean, but cheap and reliable. The printers themselves were so expensive that this worked out well for everyone. Inkjet printers are instead fantastically cheap, and most people who buy them rarely use them so demand a very low price.

Printer manufacturers have found a way to make up for the money they have to give up in the initial purchase: Disposable cartridges. Initially these were just a consumable, an extra revenue stream, but over time, companies started putting more rules in place to prop up the cartridge prices, and to ensure all that money went to them, not third parties: You had to buy them from the manufacturer, they had to be replaced every year, you could not refill them.

This hurts the user in the name of making money for the vendor. People are unhappy enough about it that the US Supreme Court had to weigh in.

That’s good product management. Well, evil, but you know what I mean.

Reasonable people might disagree on the wisdom of this approach, but it begins to reveal a distinction between the simplicity of “tool” versus a more complete “product”.

When I think of a tool, it is uncomplicated. When I use a hammer, it just has to fit my hand and smash stuff. When I pick up my drill, it works with every bit I own, regardless of where or when I bought it. The battery and charger are proprietary, but the vendor’s most visible role in my life is color choice. My yellow drill works just fine with bits from the blue or green people. (Just mentioning the colors probably caused you to visualize these companies. Branding works, even for tools.) It does not matter whether I bought the drill from Home Depot or inherited it from my dad; once in my hands, it just works.

A product, however, exposes you to its business model. There’s no difference between the dish soap sold at retail and the one sold in bulk, yet they’re separate products, differentiated through packaging, shipping needs, and labeling. Those differences obviously impact price, and how you use the soap.

Tools now become a kind of counter-point, a better offer:

It helps you do your job, and makes no demands of you in return.

I know how DeWalt and Mikita make money, but I don’t think about it when I’m using their tools. I can comfortably recite that my canonical hammer is the Estwing 22oz waffle head with a straight claw1, but none of those details mean I need the vendor’s permission to hit a nail with it. I make a decision about the right tool, I buy it, I use it. End of story.

It is small. If you call something a tool, not a product, you’re saying it’s less, it’s not as complete a solution. “It’s just a tool.” You can see this as belittling, insulting, but it does not have to be. It’s also a statement of choice. Of freedom.

Products have an implicit, ongoing dependence on their vendor. As that vendor, this works well for me: I want you to pay me all the time, not just once. That ongoing relationship is how I afford to keep improving what I’ve built for you. But it’s not always a healthy relationship. These interactions often shift from helping you to sustaining a business model, as they did with inkjet printers.

When I say I like tools, I’m rejecting all of those interactions. I want something self-contained. Independent. Usage is a pragmatic decision, not a lifetime commitment.

That independence has downsides for founders. You don’t get any of those delicious growth-hacker buzzwords. Your product isn’t “sticky”, there’s no “moat.” Those are examples of my customers being forced to experience my business model, and their absence means my business is harder to build, to protect.

One might argue in return I’m better off because I treat my customers with more respect, and I’d probably agree. I think this is often the right answer, but it’s not a popular one. I might be accused of not “wanting to build a real company,” or I might be insulted in the most dire way possible: “That’s just a lifestyle business”.

Tell that to Adobe. And AutoDesk. These companies are built on their tools. They are the behemoths we know today because they knuckled down and solved their customers’ problems. It was a different time, but people have not changed.

I don’t think that every product is compromised when the customer experiences the business model, but I think most are. Some of it is laziness, knowing you don’t need to finish because your product will cover for you. But a lot of it is strategy, recognizing the value of a product over a tool.

I want to build tools.

  1. We told with great pleasure the (most likely apocryphal) story that this hammer was illegal in Florida because the metal haft could cut your thumb off.

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.