I don't think every product design decision needs to be 100% rational

Why not!

It's a deal if you can answer one question: what happens when the breadcrumbs get long? (i.e when you're viewing a "deep" board) :)

Hey Mike, thanks for the questions! Switched from numbers to letters since the automatic markdown in this editor is killing me!

A. We’re a pretty small team, here are the different roles:

• Me (product design & management, marketing, PR, fundraising, recruiting etc etc)
• 2 full time developers
• 1 part time visual/brand designer
• 2 part time customer success/support people (onboarding, support messages etc)
• 1 part time operations/finance/sales etc.
• 4 official advisors (few hours a month)
• 1 external board member

We’re planning to add soon:

• 1 full time mobile developer
• 1 full time growth/marketing person

B. Mentioned this in another answer, but it’s pretty hard, we tried and failed a few times before getting it right. I think the key is really committing to it, by putting people on it full time for good (i.e. not trying to mix it in with client work). I was a founder & am still a director at the agency, but I don’t have a single conversation or meeting about client stuff any more. I really have no idea what’s going on there :)

C. Hopefully next year sometime, but it’s really unknown at the moment. Depends a bit on where we go with the business model, which we’re still considering at the moment. We bootstrapped the first 18 months of development (using agency profits) and we’ve just wrapped up our first round of investment to keep going.

D. Milanote is a portmanteau of “Milan” (the great design city) and “note” :)

Thanks Hayden!

A. Short answer: lots of interviews and user testing. Long answer: we started with some simple hand drawn sketches of various states of the product, and took them around to lots of designers to see if there was any interest in the concept. That was really good, because the sketches were vague enough that people could say “and it would be amazing if it did X!” and kind of project their own ideas on them. Then we built a quick and dirty “alpha” which we used ourselves for a few months (and tested with other people a lot) before starting over with a beta (which became the final product). Milanote actually started as a tool just for UX research analysis, and gradually became generic as we tested it with writers, filmmakers, architects etc and they liked it too :)

B. Oh man that’s a hard one. I think one really good sign is if someone asks lots of questions before they start working on anything (or even has an opinion about it). One of my mentors is Philip Fierlinger (co-founder & ex head of design at Xero) and when you ask him for advice on something to him about anything, he spends the first 15 minutes asking millions of questions before he’ll even think about offering it. I think that’s the sign of a great “designer” mind—someone who spends a huge amount of time trying to build a model in their head of the situation and the problem before trying to solve it.

The other key thing is being able to switch between divergent and convergent thinking at the right times (check out the double diamond if you’re not familiar with the concept—I actually have it tattooed on my arm as a reminder). This is mostly a practice thing, but some people do it really naturally.

Some other obvious ones: the ability to write well, great at building up other people around them, a love for learning, I could go on and on!

C. I can’t really imagine this happening to be honest—the research is just an input, it’s not like we ask people “how should this feature work?”, it’s more like “tell me about your goals and what’s stopping you achieving them”, then the design comes from that. One thing to keep in mind is that users are great at pointing out obvious features you need to add, but they’re almost unable to see beyond the obvious solutions (because they’re not spending all day thinking about it). So with Milanote we’re trying to balance giving poeple what they ask for with giving them things they aren’t expecting.

Hope some of that is interesting/helps!

Glad you like it! "Dark mode" isn't something we'd planned (I tend to fall into the camp of less options for customisation for products) but people keep asking for it, so it's something we're thinking about. Some kind of f.lux style automatic colour shifting would be interesting now that I think about it :)

If you're really desperate in the meantime, a couple of people have done it themselves using custom stylesheets (!).

Hey Tom—alright, you asked for it! That's a really tricky question and the answer will be different for everyone. Here’s my 2 cents:

Let’s assume that your career will last about 50 years in total (roughly from 20 to 70—retirement age keeps going up). That means that hypothetically, spending 4 years on a degree in computer science would cost you 8% of your working years. Assuming you’re planning to design digital stuff for the other 92% (big assumption) that sounds like it might be a good use of your time.

Now a whole degree would be pretty extreme, but hopefully you get my point—I think in general people designing digital things should invest much more time in learning to code than they do, and I think in the future the line between design and code will blur more and more. This is already happening (as you mentioned). I also think that the tools people use to design digital stuff will start to look more and more like a combination of design and programming. I already think it’s more useful to think of individual “product” people as sitting somewhere on a continuum.

Now obviously keeping up with all the latest fancy frameworks and technologies is a different question. Personally, I think that’s very difficult/impossible to do that once you get a bit older, have kids etc (but until it happens to you it’s hard to appreciate). For me, UX and design skill are much more intuitive, enduring and require much less “upkeep”, so that’s the direction I’ve gone in. It’s also worth reading one of the million threads on Hacker News about what happens to developers when they reach the age of 40 (still with 60% of their working life to go!).

Sorry for the long rambling answers, hope you get something out of it! :)

Great question! At the moment, the metric we care most about is active users. If that's going up, we're doing OK, if not, we're in trouble. So far it's been going up by double digit %'s every week, but we're not taking anything for granted :)

We use Intercom to measure activity, and we have quite a complex way of deciding who's active and who's not (i.e. has created X pieces of content, has had Y sessions, has been seen in the last Z days). I think what we count as "active" is probably a bit stricter than the average SaaS product.

We’re also working on implementing cohort analysis (couldn’t find the perfect of the shelf solution so we’re building it ourselves). This will basically let us see what happens to groups of users over time. It’s still pretty early, but I’m really interested in being able to see how long it takes different people to become active, how long it takes before they decide to pay, refer other people, invite team members etc.

Revenue is also a pretty obvious metric and it's been fun watching it going up, but to be honest I'm trying not to get too distracted by it—we're still really early in terms of the business, so I'm trying not to get too attached to our current business model. Going for a more "pure" freemium model (i.e. making the product much less restricted for free users) is still an option we’re considering.

In terms of communicating about metrics to the team, I post some graphs to an internal Milanote board once a week and write a short update on Slack about how we're doing. All of our stats, dashboards, analytics etc are all completely open for anyone on the team to check out.

In terms of investors, we've tried to find people who are prepared to let us experiment and change our minds rather than get too attached to a particular metric, so we haven’t felt any pressure to do things we’re not happy about so far :)

1. I wrote an article about it a while back, it’s basically about having some time to focus and concentrate without interruption. A bit weird but it works for us :)

2. Nothing to compare it to really, but from what I read about the startup scene in the US it’s pretty different. I think it’s much harder to get investment here (although we haven’t had any problems so far). On the flip side, I think it’s easier to attract talent, because people have less options if they want to do the startup thing (i.e. we’re not competing with big tech companies). Because Australia is a rich, educated country there are lots of talented people around and not a lot of interesting jobs. Slack and a few others have recently opened offices here which I think is a smart move.

3. Technically speaking, one thing that comes to mind is we spent a long time figuring out how to turn a 2D canvas of elements into a 1D list that would match the way a human would do it. Still haven’t quite nailed it! The two big challenges that are on my mind at the moment are figuring out the right business model/pricing and marketing :)

4. During our beta, we got a huge amount of the same feedback, so before we launched we built a poll which let people vote on common features (rather than everyone telling us they wanted an iPhone app). This has been a great as an input into our roadmap, but also as a way of taking the load off support while still giving people a way to voice their opinion. This is a great tool which just came out which does the same thing. If someone suggests something we don’t want to do, sometimes we’ll explain why (although this can be hard) and other times we’ll just say “we’ll think about it” ;)

Some other ways we think about prioritising features:

• Is it consistent with our vision?

• Will it unlock other features?

• Will it add new capabilities for minimal work?

• Does it solve a fundamental problem with the interface?

• Could it get us lots of new users?

• Will it fix things which are broken or unfinished?

• Will it enhance the app for our most important users?

• Is it a boring thing we probably need to do?

A typical day starts with a standup meeting. There are two things we do differently here: the first is we ask "how's everyone feeling today?". This is a bit of a weird question, but the idea is that if you find out someone is stressed/miserable/grumpy/tired then you can treat them differently (or figure out a way to help!). The second thing we ask is "is there anything preventing us doing quiet time today?" if not, then everyone spends the first 4 hours of the day in silence getting shit done :).

The rest of the day depends on who you ask, but the common things are:

1. Everyone does a lot of interacting with customers, answering support messages etc

2. Developers get to write code all day (they only have meetings one day a week)

We’re working on an OSX app at the moment, and planning to put out a call for beta testers soon—same will go for various native apps over the next year or so :)

In terms of the agency thing, we’re planning a one way transition to the product side eventually—at the moment we’re 50-50, some people are just doing client stuff, some people just making Milanote. It’s just a case of the right roles opening up for people on the agency side (and having the money to pay them to do it).

And in terms of being escorted from the building, it’s pretty simple—the four co-founders our intention to leave (but offered to work out our notice period) they were upset and kicked us out straight away. The lesson is: if you’re planning a new business while working for someone else, don’t assume they’ll be supportive.