John Sindelar of SeedCode: 5 Things I Wish Someone Told Me Before Became A CEO

Candice Georgiadis
Dec 23, 2020 · 11 min read

We overestimate what we can do in one year and underestimate what we can do in ten. I think every successful founder is both frustrated at how slowly they’re making progress, and at the same time, they’re amazed at how much they’ve accomplished. This is natural and is part of how our brains are wired to see risk over time. Knowing this can stop the frustration from becoming paralyzing.

As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing John Sindelar, CEO of SeedCode, creator of DayBack Calendar, a schedule balancing app that shows you the consequences of your decisions. DayBack arose from years of building custom interfaces where companies could visualize their timelines and capacity.

John was an artist before finding that building things with code scratched the same itch. The community of software developers was a stark contrast to the solitary world of art-making. John began helping developers write more portable code, publishing examples, templates, and eventually co-founding PauseOnError, a developer’s unconference.

John has written and spoken extensively on software patterns, how to increase code quality while staying lean, and rethinking your approach to time. He’s a surfer, trail-runner, and feminist running SeedCode as an all-remote company from the Pacific Northwest.

Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

I was an artist before this, a painter and a sculptor, and I’d always been keenly aware to structure my life so that I’d have time for my work, despite whatever I happened to be doing for a job. So I was pretty focused on defending my time, though I couldn’t have articulated it like that. Eventually, I found that coding scratched the same creative itch as painting did — just without the nightly confrontations with my self-worth. It didn’t feel very un-punk-rock to give up painting for making software, but coding also gave me something the art studio never had: an audience. And when I looked at what that audience wanted, I saw people with the same challenges defending their time that I had. So building them a calendar seemed like the thing to do.

Can you tell us a story about the hard times that you faced when you first started your journey?

There are so many: from the loneliness of just screaming into the void, to all the financial mistakes you make starting out. I remember chain-smoking on the back porch waiting for invoices to get paid, trying to puzzle out how we’d pay rent. Those month-to-month struggles were hard, but it was clear that just a *little* more cash flow would make most of them go away.

What was truly hard was that everyone seemed to be so far ahead of us. There were very polished calendar add-ons when we started (or what appeared to be very polished), and it felt like it would take years and years to catch up. That was demoralizing. Fortunately, I’d picked up this quote from the folks who worked on Gmail in the early days: “you don’t have to be good if you’re great.” They used that to mean that you didn’t have to have lots of “good” features if you had one truly great one. In their case, Gmail shipped without lots of the things we take for granted today, but unlimited storage was a breakthrough. We took this as permission to build our differentiator features first and leave out lots of table-stakes stuff. Our first versions didn’t support repeating events or invitations — but it would let you look at your schedule over long stretches of time. People responded to that. And maybe, more importantly, the team felt like we were gaining on these other apps — that we were doing something they couldn’t.

Permitting ourselves to defer lots of stuff — permission to define for ourselves what mattered — turned out to be pretty key. You have to make your own meaning, especially before you have customers that will find meaning in your work.

Where did you get the drive to continue even though things were so hard?

I’m not a fan of “burn the boats” as a way to motivate people, but when you’re alone and starting out you often have little choice. You don’t have enough resources to make several bets: so you make one bet, and that one has to work or you’re out of money. Money always has the last word and it’s a pretty strong forcing function.

So, how are things going today? How did grit and resilience lead to your eventual success?

In some ways, we now have what we always wanted: an audience that relies on our work, and a team that turns our wild ideas into features or experiments. I think what’s survived from the tough times is this impulse to defend our time — which now takes the shape of making sure we’re building a sustainable life for ourselves and a sustainable business.

For example, we get paid in advance for all our custom work. That means we do more smaller projects — which is the way it should be; it stops us from outrunning our understanding of the customer’s problem. And we don’t require the revenue of developers billing eight or ten-hour days. You just can’t sustain that: more than five billable hours a day is a pretty impossible day in and day out. At some point, you’re just making bugs and teaching your team to resent the job.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

This is no less funny for being fairly common; I remember closing a deal with a client telling him the price for our software — which at that point we sold as a one-time licensing fee. The client wrote it down and asked if that was per month. I was so shocked that this person thought it reasonable to pay over ten times what we were charging that all I could do was babble about how, no, that wasn’t per month and launch into some embarrassing explanation of our pricing model.

It would be nice to say this only happened once.

I’ve taken two things away from this — though clearly, I haven’t wholly internalized either of these. First, the story-arc you have about your product and its price is only visible inside your head. Your customers don’t share it and are only looking at the anchor prices in their immediate environment. They don’t know that your app used to be cheaper, or more expensive, or that you just figured out how to scale. Second, when someone offers you more money, take it.

What do you think makes your company stand out? Can you share a story?

There is a kind of ambition that has only been evident to me in hindsight. Early on, one path for our product was to fill in gaps between other parts of the calendar stack: we could sync events between calendars, for example, and there seemed to be a lot of work there. Same with linking payments to appointments. But we had some intuition that these kinds of products weren’t ambitious enough, though I couldn’t articulate precisely why. At the time, I said that other players would eventually close the gaps in their own stack — Square would add a calendar, and Salesforce would sync with Outlook — but I wasn’t sure of it. In hindsight, I think we recognized that these gaps weren’t what made our calendars unmanageable. The root problem was using this one-week-at-a-time interface designed hundreds of years ago to help people meet liturgical obligations. We wanted to build a better way of seeing the calendar — not help existing calendars talk to the other apps in our lives. At the time, I described this as needing to build what Google Calendar wouldn’t — thinking that I was just being pragmatic in not filling gaps that other apps were already closing. But in hindsight, it’s a certain kind of ambition to work on the root problem and not play around on the edges.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

When you’re small, there is a good reason to put in 20 hours on any given day. Part of surviving is just deciding that you won’t, and designing a business that doesn’t require you to. That’s what lets you keep at it for the long term — for all the experimenting and listening that’s required.

It’s exciting when your team is signed with your vision and putting in long hours. But they can’t do that indefinitely, so make sure you’re not building systems that require them to pull 20 hours also. Or systems that require them to ship on weekends, for example. That kind of thing can work, and even be exciting, when everyone’s healthy and things are going well. But when things get pulled taught in people’s personal lives — or your own — you’ll be glad you’ve designed systems with some slack in them.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Many years ago, we were charging much, much less for our application. A colleague took the time to write a couple of paragraphs about how he saw our value proposition and sent it as his pitch for why we should charge more. I am very, very glad that I took his advice. (There’s a big difference between agreeing with advice and acting on it.) This isn’t the kind of thing he needed to have said, and I’m sure he worried that his advice wouldn’t be welcome, but it made a massive difference to us.

By the way, one reason he likely felt permission to but that I’d been very open with him about our operations and what I was fighting. So there was some trust there already. That’s my reminder to share what we can and build that trust up as small opportunities arise.

How have you used your success to bring goodness to the world?

It can be frustrating — being the chief of your little kingdom but unable to pull many levers outside of it. But we’ve tried to pull the levers we can reach. We donate a percentage of revenue to DESC (https://www.desc.org) in Seattle, where we started. DESC runs some of the most successful housing-first projects in the world and is working on a concrete plan to address homelessness. As a tech company, we’re part of the problem, making our city less affordable. Working with DESC is one way to offset that.

We were also pretty engaged in the 2020 elections in the United States and published a series of timelines to get out the vote. The idea was to show folks that their votes this cycle are part of a long history of campaigning for women’s suffrage and standing up to voter suppression. This kind of thing can feel like screaming into the void, and you’re never sure if what you’re doing is making a difference, but it was important for our team to know that we were using our product to speak to what was motivating us all personally.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

Charge more. We see this all the time when other software firms want to license our calendar; if they’re not charging enough, they just don’t have the room to license components and have to build everything themselves. You can only charge more if you’re solving an expensive problem for your customers.

Risk management isn’t about reducing risk: it’s about allocating risks. This from “Antifragile” by Taleb — many people think risk is about balance: picture a barbell, and you want to move all the weight to the center of the barbell. Taleb suggests a better strategy is moving weight out to opposite ends of the barbell. On the one side, you have very low-risk activities. They’re low risk, but they have a limited upside: they’ll only grow incrementally, for example. On the other side of the barbell, you have high-risk bets that are unlikely to pay off: but if they do, they have an almost uncapped upside and could grow wildly. When I was just starting out, I could have used more high-risk bets to balance out the safer parts of our business.

Software does not have zero marginal cost. Or it only has that kind of cost if you don’t maintain it and don’t support your customers. So every feature and every use case your app supports has a long tail of cost. It can become a lot to carry around and I think it’s why some of the most successful software re-writes are actually re-starts on more focussed products. Look at Fogbugz becoming Trello. Or Gmail’s rewrite as Inbox (oh how we wish Inbox was still around). These were narrowing their use case as much as they were rewriting the code.

People stretch themselves in low-stakes situations. I used to think that my primary job as a CEO was to raise the bar for my team. I was so into “raising the bar” that I made life very tough for my direct reports — I even had a couple of people quit before their start date as they could sense I was unreasonable. Maybe they could sense that “shame” was my only management tool, since shame is what had worked on me. But one thing rough-water sports have taught me is that people can only push themselves when they feel they’ve got some backup. I used to do a lot of sea kayaking around rocks and cliffs and it was clear that people would try new things to the degree that they trusted the rescue boaters nearby. Bringing that back to my team now means that we don’t shame people for failures or oversight. I want people to try the risky thing, knowing that we’ve got their back.

We overestimate what we can do in one year and underestimate what we can do in ten. I think every successful founder is both frustrated at how slowly they’re making progress, and at the same time, they’re amazed at how much they’ve accomplished. This is natural and is part of how our brains are wired to see risk over time. Knowing this can stop the frustration from becoming paralyzing.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I’d like to think anyone with a good answer to that question would already be working on it. Our own small contribution is making a tool that trains us as a species to reset our planning horizon further into the future.

How can our readers follow you on social media?

We’re @seedcode and @dayback on Twitter and @daybackcalendar on Instagram.

This was very inspiring. Thank you so much for joining us!

Thank you!

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