Note: This AMA is closed for new questions, but you can check out the existing conversations below.
This August 26th, we’re incredibly excited to be hosting Trello’s (and Fog Creek’s) co-founder, Michael Pryor. For almost two decades now, across a dozen or so products, which have included geo-focussed job boards and documentaries that reached DVD players in New Orleans and Kazakhstan, Michael has witnessed quite a bit of the spark and verve of creating things. But also the company-building rigour (scaling multiple product teams to serve millions of users, even being a CFO) that must accompany those creations out into the world.
AMA Index (Michael’s brain-pickings) 
( Hard-won insights, opinions, and observations; thoughtfully examined and articulated )
— On the non-linear, strikingly distinctive paths that led to dead-ends and to massive successes
— Distill (and document) opinions, trade-offs, founding stories, and principles that have shaped the product; in their case, unpacking: making something “Trello-y.”
— Two things that are relevant to any product creator: 1) “over time, your feature requests will just be things other products have.” And 2) “and more to the point, ask your users WHY they are asking for these features?”
— How most-requested features and actual product priorities CAN differ. Illustrated with two instructive examples “where our user’s think we are completely wrong (and have thought this for years).”
— On pricing: Avoid the long-term, inhibitive price grandfathering tax with transparent time limits, say no to flat rates, and arrive at multiple value axes.
— Michael’s notes on the Atlassian acquisition
— How following Slack’s promising (from the outside) “fair-billing” approach backfired
— Targeting verticals: “be careful that you continue to find new customers that fit that bill (vs. just continuing to rely on the [old] one(s) to guide you)”
— The ‘five whys’ for getting to the heart of a customer challenge/request
Further reading/listening/pondering from the interwebz 
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(Other insightful excerpts drawn from blog posts, interviews, and conversations)
On the transition to building a massively horizontal product:
You’re right that most of the people that knew about us, knew us from Fog Creek…they were mostly developers. We also co-created this company called Stack Overflow, which, if you’re a developer you know what Stack Overflow is. It’s a Q&A site for devs. And so, that was most of the people that saw the app in the very beginning.
And, that was a weird dilemma for us, because what would happen was, people would show up and they would start asking for feature requests for things that they had seen before. Things that were very appropriate to their work and who they were in their role.
We sort of had to ignore it a little bit. Everyone says, ‘listen to your customers.’ It’s a little trite. Who else are we going to listen to? And I’m not going to say, ‘don’t listen to your customers.’ But I think like, the lesson there was, when people would come to us with a feature request. They were telling us something they had seen before.
And our trick was to build something that people loved because it wasn’t like anything that they had used before. So, if all we did was listen to the feature requests that they asked for, we would just end up with the same tools that were already out there.
So, what I told people to do and what we sort of learned to do, was to listen to the pain that people were having. So the first thing that they’d do is say, ‘here’s how to solve my pain, all you have to do is add this feature…’
I think the trick is, you had to ask them what the pain was that they were having. And think about that pain from the perspective of other people that are not developers. The trick with building a horizontal app is you can’t put a very specific feature in there that solves one person’s problem, you have to build a feature that solves most everyone’s problem.
Source: Traction Conf | 2017
On the fundamental distinctions between Salesforce and Excel, and deeply knowing the kind of software you’re building:
The problem is, every time you’re adding features, you’re creating a more complex system. And that’s what developers do all day long. You think of an abstraction and you create code around it. And then you present it to a person. Devs are really good at doing that.
But when you have that system and people come into it, then you have to explain to them what it does. So, for example, you use Salesforce, you’ve got to come up to speed on what a lead is, what a contact is…there’s all these concepts in there, all these rules around it.
Once you understand that, Salesforce becomes a very powerful tool to use as a sales person. And because Salesforce, the app, knows about the data that you’ve put into it. It can tell you all these amazing things. I can be like, ‘hey, your pipeline is too short, you’re going to miss your quota next month.’
In Trello, we’re trying to do something more akin to what Excel did. Which was, we’re going to give you some building blocks that’s going to solve the problem the way that you see the problem. I’m not coming into a very specific role and saying, ‘hey, you’re a salesperson, these are the tools that you need, these are the objects in your world.’
You can add labels to cards and that can be whatever you want. I don’t have a preconceived notion of how you work. So Trello is allowing you to build that system as you go. In the same way that when you put data into a spreadsheet, you start to tell excel, ‘well this column represents this.’
Even when you go to add a chart in excel, you kind of have to tell it, what you want it to chart. It doesn’t know. Whereas, like in Salesforce, you can be like, ‘here’s your bookings next month.’
So building a horizontal tool where you don’t know exactly what people are going to do with it, you have to think about giving them really easy building blocks. It’s tricky, because then, there’s a little bit of work that they have to do. But it also means that it can be applied to so many different situations.
Source: Traction Conf | 2017
On not reinventing the wheel with pricing:
This is a common thing that people do when you first start out, you’re like ‘I’ll charge people a flat fee, like $50 bucks to use my product.’
But then it doesn’t matter if you’re a tiny company using your product or a big company.
People don’t want to charge per user because in a collaboration product that is a vector of growth.
But for all intents and purposes, that’s also a measure of value. A bigger company gets more people using it and more value, and at this point in time everyone gets that.
So making up your own weird pricing scheme is always dangerous, and when you get to a point where people are just like, “Yeah, I get it. You pay for storage, you pay per user.” Doing what other people— What the market has now accepted as normal is often very advantageous. You do not need to reinvent the wheel in that area.
Source: Heavybit | 2019
On the enduring influence of his co-founder, Joel Spolsky:
I connected with my co-founder, Joel Spolsky, back in the days when I was working at an Internet startup in New York City. At that same time, he was the program manager of the Excel team at Microsoft. When I was working at this company, I was trying to build something in Visual Basic and most of the developers there were Linux devs, so they always referred me to Joel because he’s a Microsoft expert. So I just kept going to him with questions and he was very generous with his time as he was always working on some other things.
Over time, we developed a relationship as friends. And when the time came to start a company, I told him that we should do it together. Prior to that time, he had quit his job and was taking time off. I also quit my job so that we could start working on the company. Even though he had vast experience more than me, we split the company’s equity 50/50.
I think learning from him and being present for that early stage growth of our company and riffing on the ideas about our structure of compensation for people and the kinds of benefits that we wanted to provide and building a software company in New York was of unheard of. Joel had a huge impact on me and has been a big mentor to me in my career.
Source: Authority Magazine | 2020
Really looking forward to the AMA.
