Four Months Ago…

Hi Sebastian & Kai,

Unfortunately we decided not to fund Ultraworking for the YC Summer 19 batch. We were impressed with your solution to the productivity problem; however, we were not convinced that this was a tech company - yet. We encourage you to continue converting much of your learnings into software so it can work autonomously. And increase your retention. When you progress, we encourage you to re-apply to YC. Thank you for sharing Ultraworking with us today!


Ouch. Holly and Gustaf were very kind to give pointed feedback. We’d had a lot of success in bringing results to our customers, but these were totally reasonable points. We’ve put a lot of effort, thus, into how we develop software and put up some wins in the last four months since we interviewed.

Such as…

Electron Desktop Application

Download Headquarters 0.0.5, Stable Alpha, here. (Mac only.)

We spec’d out Headquarters before we left San Francisco.


Our original inspiration for Headquarters was an “IDE for Knowledge Work” — persistently on. We can help people add a mix of free and paid modules to Headquarters that they’ll have “always on” to reference and keep track of their work.

Electron is a bit finicky and we don’t think the experience is quite good enough yet, but we’ve done some hard engineering to set it up well. The big thing you won’t see testing the rough prototype of the app is that we’ve been building it to support third-party developers adding modules like VS Code.

We’re also building modules for it that convert things we’ve done in the past to software alongside new high-value things that a desktop application makes possible. Coming up first:

“Work Cycles” is something our customers already know and love — you find out more about Work Cycles at,, and — all of these have been quite popular and gotten a rave reception.

“Lights” has also been popular as a free tool; you can find out about it here:

We’re also excited about eventually getting access to system data — things like typing speed, application usage and times, etc — and to use a mix of APIs and analysis to give people personalized feedback. As soon as we’ve got core experience very enjoyable, we want to add a Spotify integration to help people track which music they’re most productive when listening to.

We’ve had current customers involved in the development process and there’s a warm reception across the board so far. Given that Electron inherits some WebKit security defaults, it’s been a bit finicky looking to make it a great smooth experience across multiple windows, but we’re planning on having a fully launched version with 3-4 good modules by the end of 2019.

Also, we’re using Auth0 and consolidating all our logins so data can be shared across applications, which brings us to the next point…
Live Beta Released, Good Reception

While Kai has led up the development of Headquarters, Sebastian took the lead on getting launched (along with Lee Knowlton and Saad Zafar, who have done excellent work).

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Screen Shot 2019-09-26 at 5.19.17 AM.png launched on 30 August 2019. Customers pay $49/month billed quarterly ($147/quarter) and it’s had nice success so far. Before, we did it all with “duct tape and lots of goodwill” — indeed, we’re doing more software now.

We’re currently releasing one feature on TWG roughly every two weeks; we’d like to get Dev Velocity up to releasing one good feature per week by the start of November.

Is a Max-Quality Podcast
Worth Demoing?

We think so. We launched our podcast on August 26th — we’re aiming to make it a high-quality DAILY by the end of 2020. We’re aiming for ~80% of the quality of Hardcore History, one of the most popular podcasts among our social circle.

It’s had a really, really good reception.

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We’re currently doing 2-3 shows per week; the goal is for Sebastian (cofounder) to eventually do roughly 10 shows per month, with the other 20 being spread among our team.

We got an exceptional composer we knew to do a really unique intro, got a top-notch radio producer to commit to editing two shows per week, and we put a lot of time into figuring out what’d be exceptional.

If you want to hear what the creative process was like, dive into Episode #5: Rough Creative Process Rough. The show with the most depth was Episode #1: The Holy Grail. The most mainstream popular show was Episode #6: Mathematical Arguments for Serializing Projects.

So far, we’ve got 22 five-star ratings and 13 five-star reviews on iTunes. We’ve had 3,836 downloads since launching the podcast.

Hope to see you soon.

Thanks for checking us out — we were grateful for the opportunity to interview the first time, and we took the lessons learned to heart. On the churn front, after calculating, we were at 6% monthly (blah!), and are now targeting <2% and started working on that with Stripe Sigma, Product Improvements, transactional email via Sendgrid instead of ActiveCampaign, better onboarding, and generally just delivering more exceptional results for customers all the time.

If you want to see the first major software we made back in the day, we still think the Ultraworking Pentathlon is pretty cool for people — that’s all delivered via software and pretty cool. If you’d like to participate in the next Pentathlon, it’s October 12th-27th. We’d be happy to have you one of the YC team or a past YC alum attend for free to check us out — shoot an intro if you’d like to try it out. If you want to join some live Work Cycles as part of The Work Gym, again drop an email and we’ll set it up.

Or feel free to mystery shop us — our stuff works really, really, really absurdly well for customers. (You can see a bunch of video testimonials here.)

In short, we’re still as obsessed with the space as ever, our customers are still winning, and we think we’ve turned up the development speed quite a bit and started wrangling churn since we last interviewed. We’d love the opportunity to interview again, and if we seem like your type of people — we’d love to keep building alongside you.

Thanks for your consideration — highest respect and regards,

Sebastian Marshall
Cofounder and CEO