Slopes Diaries #43: Chasing a Goldilocks Business

Slopes Diaries is my ongoing journey to turn my indie app into a more sustainable part of my business. First time reading? Catch up on the journey so far.

What is Slopes? Think Nike+, Runkeeper, Strava, MapMyRun, etc for skiers and snowboarders.

I've been thinking a lot about a problem we all face time and time again: one of our favorite apps dies. Too often though it isn't a true case of blinking out of existance, it'll be a "death of what we knew and loved" – either through a pivot or an acquisition / acqui-hire everything starts to change and we no longer recognize the original qualities that made us love the product.

Specifically the recent update to 1Password has me reflecting on how I can best avoid this for Slopes.

For context, 1PW started 10 years ago an example of delightful native software on iOS + macOS, and is now instead a bland Electron cross-platform app that is chasing that addictive enterprise-market money, a pivot which has left many of their original core users feeling abandoned. This post, though, is not an internet-rage on them.

See, here's the sitch - 1PW has Apple, who thanks to their auth team has been doing a great job making authentication suck a lot less on iOS / macOS, so much so that I'd argue 1PW for the average consumer on iOS is almost unnecessary. With a team of 500+ today [1] at 1PW (~100 the year they took their first round of funding [2]) that threat from Apple feels pretty risky to ignore. That's a lot of employees to support and Apple's system-level tools are gonna eat into 1PW's consumer growth more and more every year. So their choice to raise some money and get into enterprise software to hopefully become entrenched as a passwords / secrets management service seems like smart business to me.

I genuinely don't think they did the "wrong" thing, even though they are losing me as a customer. Sure it meant building enterprise software (🤮), but it's better than laying off employees because Apple is chipping away at their customer base from one side and LastPass (who also raised a ton of money) is eating the base from the other.

But just 'cause they didn't do anything wrong doesn't mean this outcome was inevitable. I personally think there is room, even in today's market, for a smaller password management app. A business that could support 1-4 full-time people. Said app doesn't have the audience of today's 1PW, but that scale of app did exist in the beginning. The team just chose to grow beyond it.

Managing team size is a challenge, though, because so much of what is around us as founders pushes us away from smaller businesses: "unicorns", "exits", needing constant growth year over year, big ideas that have to "change the world" (was talking with a friend a few weeks ago who was lamenting that a coworker was told to change their pitch deck to be more change-the-world-big in order to raise funding 🙄). As a founder you have internal pressure too because more growth means more employees, which means you can do more. "But if we can just hire 1 more developer, we can finally do X."

It's an easy trap to fall into, to keep chasing growth. You start to feed that cycle innocently enough because you need more people to keep up with work, and then you have to chase bigger and bigger things to keep that growth % up next year to support costs, and then you need more people to keep up, yada yada. Suddenly you look around and realize you have a team of 100 on payroll that you're responsible for.

Left unchecked you may stop worrying about building the best product, and you instead focus on building the best business. It is a subtle subconscious switch, but it'll have massive impact on the product your customers use.

To counter this, one thing I've realized with Slopes is that time is one of my greatest resources.

I might be the solo developer building the iOS app + watchOS app + and PHP backend, but over the years I've built a product that rivals those from many teams. Just like we all tend to over-estimate what is needed for an MVP, we're even more likely to overestimate how much we have to ship every year to keep customers happy. If you aren't in what I'd call a "unicorns-only market" niche, and you're decent at being nimble / focusing your efforts in the right places, odds are you can ship more than enough with a small team or even just yourself.

It's easy to get caught up in the priorities of the month / quarter / year, the sense of immediate urgency, and lose sight of the fact that we do have time as a resource on our side. In those cases I try to take a step back and play my choices out over the long game – 2, 5, 10 years out. You don't have to have a roadmap that far out, geez no I fly by the seat of my nonexistent pants, but I always try to consider how I'm impacting my future-self. What burdens or risks are you putting on my future-self? Does this fire I'm putting out actually matter in the long-term? What pieces do I really need to put in place today to help myself next year?

9 years in and I'd argue being small and nimble with a focus on future-self has been a huge strategic advantage for Slopes. Sure it took me this long to get to 1.25mil ARR and I could probably be at 2mil+ by now had I taken more risks and over-extended with confidence (hiring sooner / etc, I play it very conservative), but I'm sure I wouldn't be shipping the same product. That "Slopes" would be serving the business needs, not the business existing to serve the product.

Don't get me wrong I certainly watch my growth metrics, write and tweet to share them, but behind the scenes I've been trying to temper any focus on immediate metrics with a purpose of building Slopes for a decade+ more.

These recent events have helped me solidify the idea that I want to keep Slopes small(-ish). Not solo-dev, but small-team.

What does that look like in my head? Keep it just me on iOS + watchOS. Maybe get a web developer one day once I just can't manage to do Apple platforms + web alone, but a part-time contractor might even do. Keep my part-time contractor on Android (he's awesome). Basically one full-time dev per platform, if that, max. From there build whatever team is needed to support the product we devs can create and maintain.

But I think, I hope, that size will keep me from over-extending the product. Keep me from setting myself up to have to compromise the product too much in order to suit the needs of the business. But at the same time the team will be big enough to build a product that supports the needs of market and my vision.

Slopes: Just Right Edition.

(It's fun to think of the multi-verse of Slopes ... PWWDR (VC Edition).)

All that is to say that one year after Slopes hired its first full-time employee (Ela), I'm bringing on our second employee (Emma) today. Emma's been running point on customer support part-time for 2 years, plus leading the mapping project team (5 part-timers) last winter. Titles are hard at a small business, but "Comms and Ops" seems about right.