Tom MacWright

On Placemark

Yesterday, I announced that I was joining Val Town, but that Placemark lived. And I haven’t really given an update on Placemark, the product and business, in a while. Writing about an operating business is a different thing that writing feature announcements or essays about technology: the ramifications of honesty, spin, or disclosure are so much more vast and unpredictable. This is why we often learn about people’s trials or a company’s struggles only years later, but at the time everyone exudes confidence.

But, having drafted something about this a few times and edited myself into knots, I figure it’s better to just write something. The best writing always comes after I’ve scrapped a draft anyway.

The company behind Placemark, Working Idea LLC, is still a bootstrapped, single-person entity. I’ve been building Placemark for the last two years. I had a few days of an engineer working on it, and a few hours of design review with some talented designers, but besides that it’s a solo effort. In 2021, I was working on contracts that helped pay my bills, and in mid-2022 I started working on the product full-time.

Venture-backed startups are measured in many ways, both concrete and vague: by account growth, key hires, buzz. Investor interest is its own Keynesian beauty contest. Bootstrapped startups are measured by whether they work: whether their revenue minus expenses lets them live another year.

Placemark immediately covered its costs, for servers and legal and all of that. But it hasn’t gotten to the point where it can cover my costs of living in Brooklyn, and I’m not interested in scaling down my already-basic lifestyle to make ends meet. And thankfully the rest of my career has been successful enough that a few months without income don’t scare me. But knowing that it might be a year or more before breaking even, and who knows how long before earning anything like a median salary in technology - that was hard to grapple with.

Placemark-the-product started as an extension of the idea from, a project I built back when I worked at Mapbox. It had been abandoned for years with no clear successor. Whether it would be a successful business or not, I thought that something had to exist that would be like but better. I had some ideas about what that would be and how it could be worthwhile to people, and I ran with those as fast as I could.

As a product, Placemark immediately found resonance with a lot of people who used, and, thankfully but in a way that to this day makes me a little uneasy, with people who just enjoy my work. It’s a product that really embraces geospatial for all of its complexity and promise, that commits to a bunch of key values and pushes them all the way they can go. I tried to keep the scope clear - avoiding the ideas of it being a simple tool for sharing, or an advanced tool for visualization, and drilling down into it being a tool for data.

The scope has been hard to control. Geospatial data is different than other data in ways that are slippery and require some real learning to grasp. Placemark doesn’t try to coat over these concepts or replace existing terminology with a simpler set of words or concepts. It lets you import a multipolygon, combine it with a point into a geometrycollection, and edit advanced properties of that.

This meant a delicate balance between user-friendliness and capabilities. Some users were frustrated that it wasn’t a simple tool for annotations, others were annoyed that it didn’t have the full power of QGIS or ArcGIS. GIS tools are ugly and clunky, but for every niche they have some specific toolbox - the ArcGIS analysis toolbox is something from an era of software before Figma or Canva or Google Docs: it’s a tool for professionals doing work that requires precision and power. It’s not joyful, but it’s real.

This challenge of choosing a niche was reflected in how the economics worked. I priced Placemark at $20 a month, per user. Because it’s an editing tool and not an API-as-a-service like Mapbox, it could be priced relatively simply. And $20, while high at the time compared to base pricing of something like Figma, is a nothing for a company to pay. Mid-hundreds of paying users would be enough to make it sustainable.

And people are still paying for it, but the tool found resonance in a lot of the same industries as I’ve seen with companies like Mapbox and Carto: news, academia, and nonprofits.

As an example, Carto. Carto today is sort of a business-intelligence tool on big data warehouses for companies with or in real estate. When I got to know it, Carto was an open source tool on top of PostGIS where you could do fun things with maps and SQL. It was tremendously popular with academia, news, and nonprofits. Everyone I knew who was teaching GIS or something that required maps used it, loved it, and misses it. It was free, too, at the time. But of course that didn’t work, and they needed to move into an industry where people had more money to spend.

And I love academia, and newspapers, and open source. I’ve spent an enormous amount of time working on open source software and on things that were for nonprofits and newspapers. But it’s a tremendously hard way to build a sustainable bootstrapped company: there is no venture capital money subsidizing free plans and there’s no multi-year runway during which hype is more valuable than revenue.

There were a few niches that were more promising, in terms of business, and will be the focus in the future, but I think they require something of a different product, different marketing, and different vibe in general.

I hope that this reads like processing and not a postmortem (seriously, Placemark lives on), or fishing around for an excuse, or something like that. I’m not sure how it’ll read, anyway.

It’s standard to write in this kind of essay about how much one has learned and how it was all a rewarding experience. It’s standard because, if you really invest yourself in building something and trying to make it succeed, you will learn so much. I’ve learned a tremendous amount in the last two years, about myself, business, technology, other people, you name it.

I’m 35 now, and I’ve noticed that time can skip forward, that a year can seem like a moment or people can get into a rhythm and stay in it for a half-decade. Doing something big, like starting a business or having a child or moving across the world, can slow time down and make it all sort of demarcated. It certainly has for me - the last two years feel distinct and full.

That said, this phase of Placemark has been hard. It’s hard to feel the hope around it being a solo project with aims of being sustainable and distanced from the traditional startup lifecycle, but to feel it falling short of sustainability in the short run. I feel like a member of someone’s favorite indie band, cranking out hits and living the life and being fiercely independent, but sleeping in the van.

Back in June 2022, I went on a podcast and talked about Placemark. One of the questions was about risk and I said something about how this isn’t deep sea fishing. I didn’t go into much detail there, but I think about it a lot now. Everyone has some capacity to take risk - when you’re young and have no dependents, you can travel around the world and learn to surf. If you’ve got savings, you can take a little risk by starting a business, or even take a little risk by quitting and spending a few months working on your art or music.

For everyone it’s different, but I do think that there’s something lost when you never take a leap. I feel like I see this when people climb the career ladder and just keep climbing. There must be some opportunity unlocked by taking a little bit of stability and salary that you could’ve gotten and doing something else with that energy.

Where do we go from here? I answered part of that yesterday: I’m putting my heart and energy into Val Town and so far it’s been spectacular feeling the energy of working with Steve, Rodrigo, and André on something that so many people want to use and so many people see the potential of. A lot of my career is getting products and startups from prototype to production, getting teams from ad-hoc to aligned, and I’m excited to do that.

I’m still maintaining, fixing, and upgrading Placemark: heck, it has some features that I haven’t even blogged about yet but that shipped a while ago, like drawing circles. It has a lot of features that have been announced but never properly marked, and I’m going to spend some time just trying to get those in front of people.

I think the product as it is could be really valuable for a company that has other parts of the geospatial stack but needs to connect the dots. Or it could be successful, as it is, aimed at a market and really marketed. There are probably many angles and opportunities that I’m not seeing but as a solo entrepreneur it’s hard to see. My contact information is on /about if you have ideas.

At the start of 2023 I started working on a Figma plugin, also called Placemark, for creating vector maps in Figma. That has been a lot of fun to build, and if Figma’s metrics are accurate, has already gotten some attention.

I think there might be a path of integrating with Google Sheets or Airtable, or a path of working with very large datasets. Geospatial applications feel very bisected between the professional and novice users - Placemark-as-no-code-maps-on-Airtable is so radically different than Placemark-as-big-data-GIS. I’ve envisioned it as a tool that you can use for simple things but can grow into a tool you use professionally or semi-professionally, but maybe that’s not the future: the future is Canva, not Illustrator.

Between success and failure, Placemark has landed in the middle so far. It’s one of the biggest risks I’ve taken, and it’s been extremely rewarding, if not sustainable as a career for now.

In that podcast last year, I was also asked whether I had any advice. I didn’t then and I’m probably not going to give any now. The kind of things that you learn in this experience are more like what you learn by running a marathon or moving to a new city: you can talk about them, but it doesn’t really impart the knowledge.

I guess my advice is: if you really have the time, money, and stability that it takes to make this kind of leap, you should do it. Because that’s a rare gift, to have time and freedom. The luck isn’t just when we win the bets: the luck is having the ability to make a bet.