Michael is the CEO of Trello, the tool that helps entrepreneurs organize their businesses and lives. He’s also the Co-founder of Fog Creek Software, sits on the board of Stack Exchange, and currently lives in Brooklyn with his wife and two daughters.
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Worst Entrepreneur moment
- Hurricane Sandy swept into NYC and almost wiped out Michael’s servers for Trello. Find out how he wrangled a bucket brigade into carrying diesel 18 floors up to keep the servers running… amazing!
Entrepreneur AH-HA Moment
- The birth of Trello… listen in, Fire Nation!
Small Business Resource
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Best Business Book
- Influence by Robert B. Cialdini
- Trello: Infinitely flexible. Incredibly easy to use. Great mobile apps. It’s free. Trello keeps track of everything, from the big picture to the minute details.
Michael: I am ready.
John: Michael is the CEO of Trello, the tool that helps entrepreneurs organize their businesses and lives. He’s also the cofounder of Fog Creek Software, sits on the board of Stack Exchange and currently lives in Brooklyn with his wife and two daughters. Michael, say what's up to Fire Nation and share what's going on in your world right now?
Michael: I am super excited to be on podcast 950. I can't believe you’ve done that many, that’s crazy. Just sitting here in New York. I'm really excited about all the stuff that we’re doing at Trello. I'm really pumped to talk to you and give you the background.
John: Cool. Well, we are going to talk about Trello. We're gonna talk about your journey as entrepreneur. But we're gonna start at my favorite place, which is the one minute mindset questions, where I'm gonna ask you five insights into your mind Michael. Number one being ideally, what do the first 80 minutes of your day look like?
Michael: If it's at home, the first 80 minutes would be spending time with my two daughters because I'm usually at work all day, so that’s the best way to get my day started. But if it's at work, ideally my background is I'm programmer and I don’t really get that much time to program, so if it was at work, the first 80 minutes would be I'm heads down writing code.
John: Heads down doing what you love, cool stuff. What's your biggest weakness Michael as an entrepreneur?
Michael: There's so many things going on with work. And there's multiple companies involved, I think my biggest weakness is definitely my inability to focus. Just everything is coming at me and it's hard to remember what is the most important at that particular point in time.
John: On the flipside, what's your biggest strength?
Michael: I've been doing – running companies for 15 years, so I think a lot of the experience that I've gained, a lot of the failures that we've had have taught me lessons. I've run businesses that are both bootstrapped and venture backed, so I've seen both sides of the coin, and when it's right to do one versus the other. And I think having that insight is really my biggest strength.
John: One doesn’t become a CEO of a company like Trello without having some good habits. And we're gonna be talking about one of your better habits in a little bit here, but what is one habit that you wish you had?
Michael: I wish that every morning when I woke up I made my bed. And the reason I wish that is because I think it gives me – it starts the day with sort of a clean mind, and a clean place, and it's something that I just never do, but something that I always wish I did.
John: I just make sure I get out of bed before Kate, and she has to make the bed then. So you have a lot of exciting things going on for obvious reasons, but if there was just one thing Michael that excited you and fired you up more than anything else, what would that be?
Michael: The biggest that we're working on with Trello right now is we're making it internationalized. It's going to be available in a whole bunch of different languages other than English. And so I think right as we're about to unleash that on the world, that’s pretty much the thing I am most fired up about right now is just basically taking Trello and unlocking that for everyone that doesn’t actually speak English.
John: That’s what I love about the world that we live in is that we can go ahead and create something awesome, but there's always gonna be a certain proportion of the population if they don’t speak that language or understand that, aren’t going to be able to take advantage of it. I've had people approach me, and we actually have now a Spanish speaking Entrepreneur on Fire, where the guy just translates it into Spanish. There's a German one starting up. It's cool that we're living in, Fire Nation, this world, and we can look at it as this international opportunity. We can expand into these new markets.
And Michael, you didn't just wake up and have Trello handed to you. I mean, you’ve been on a journey as an entrepreneur, we all have. So we're gonna talk about an awesome part in your journey coming up, but let’s start with the lowest of the low, your worst entrepreneurial moment. Take us to that moment in time and tell us that story.
Michael: Okay. I'm gonna go back a couple years. Just to give you some background, I started a software development company called Fog Creek Software about 15 years ago with my business partner Joel Spolsky. And that company sells developed tools. It sells like a bug tracking product and a code review product. And they're running on servers that are a couple blocks away from where I'm sitting in New York downtown. And a few years ago Hurricane Sandy came in. And my wife was nine months pregnant. And I was sitting in Brooklyn and all the power went out. And we assumed that our servers were in a data center, they had generators, that everything was fine.
So we woke up the next morning, there had been some flooding and I get a phone call. And basically the phone call they said we have about an hour’s worth of fuel left in the generator at the data center where your entire company is running right now, and all the customers who are using your services, so we need you to come over and shut down your computers. And that moment, and it was probably the worst moment in my life because I just felt so helpless. And I ran across the Brooklyn Bridge, I came down to the data center.
I took my phone out of my pocket, so I could get a flashlight, trying to find my way up the stairs to the data center, and I'm like: what can I do? And they basically said the water came in, it took out all the pumps in the basement, and that was actually where all the fuel was stored. Even though they had the generators and they had the fuel, there was nothing they could do. So the CEO of Squarespace was actually down there with me, and we were trying to put our heads together and figure out some way that we could get – you know, that we could help and get this fuel up to the 18th floor where the generator actually was.
And we sort of messed around, we're trying to figure out if I had pumps, and aquarium pumps, or we could go to Home Depot to buy them or whatever. In the mean time we said: hey, you know what, maybe we can buy ourselves an hour or two at a time and just start carrying buckets of fuel up 18 flights of stairs. It seemed kind of ridiculous at the time, but we started doing it. And we called people. We called people that worked for us. Because basically if our servers went down that was gonna be it. I think people could – they could take like an hour or two outage, but this was something that wasn’t gonna be fixed for weeks.
And we just got everyone that we could to come in and slowly but surely we were caring all these buckets of diesel up 18 flights of stairs and pouring them into the tank for the generator to run, and we just kept doing it for three days straight. And three days later they got a replacement piece for the pump and fixed the pump, and started pumping the fuel up and everything was fine.
John: I mean, Fire Nation, if that’s not a feel good story, what is? That’s just to me is a story about coming up and just saying: hey, it's bucket brigade time. We don’t have the modern day equipment to make things happen, but we're going to innovate, even if it means going back and doing it the old school way. And Michael, what I would really love you to do before we move on, what's just the one lesson that you want Fire Nation to walk away with from this experience?
Michael: You're never gonna have all the information that you need to make a decision. It's never gonna be perfect. You're never gonna feel like everything’s there, you just can see the way, it's totally clear. Like, that’s part of what making a decision is all about. You got to – you have to decide with a limited amount of info on the path forward and it's never easy. And I think in that situation we just said: what can we do? What can we do right now?
Because we're not – there's only so much that we can do, and so we were driving to gas stations, finding pumps, you know, we just did anything that we could because the alternative was we would let down everyone that was relying on us, and we couldn’t let that happen.
John: Let’s shift now Michael into another part in your journey. This is gonna be an “ah ha” moment, a light bulb that went off at some point in your journey, so tell us that story, take us to that moment in time and break it down for us?
Michael: This is going to tell you a little bit about how Trello came to be. We're selling a bug tracking tool to developers. And we were using it in our own company to manage our process for creating software. And we felt like we had a lot of information going in the system, but as business owners we had no idea what the heck was going on at the company. We just didn't understand at that top level view, like what's going on? Are we shipping things? Are projects moving forward? And we just felt like there was a lot of lack of focus. And my business partner, he came up with this idea for – he said why don’t we build this thing.
We’ll just call it five things, and it will be a list and you can only put five things in it. it will be two things that you're working on now, two things that you're gonna work on next, and one thing you're never gonna work on, and that’s it. And I was like that’s such a silly idea. That so – it's so constrained, no one would ever use it. And he’s like, “No, no, you see the point is that you can't do all these things at once. You have a million bugs in your bug tracker and you're just not going to fix them.
And eventually you're gonna get to some point in time and you're just going to close them all because you're gonna be like this is just too much of a backlog.” And I said, “Yeah, but who’s going to use a to do list that only has five things?” He said, “All right, let’s think about this some more.” We went around and we were looking at development teams and how they were working. And a lot of them had these whiteboards up in their office. And on the whiteboard were all these little Post-it notes, sticky notes that they had put on the whiteboard. And they were using that to get a high level view into their development process.
They were also using bug tracker, it had a thousand bugs in it that they were working on, but that was telling them: okay, this week, this is what we're working on; this is how we're moving forward. Okay, I can get a visual. I can see it in front of me. I can get perspective. I can see the movement happening. And those sort of ideas combined in our heads to come up with this idea for Trello, which is essentially this collaborative canvas that people are putting note cards on, and the list, and sort of allowing you to get this high level perspective about what is happening in your company, whether it's your development, marketing, sales, or even planning a wedding, or a vacation with your family, or buying a house.
And I think that was the leap from actually we can do more if we constrain ourselves and get rid of all this stuff. I think you see that with this move towards people trying to get inbox zero because they just feel so overwhelmed by – and inundated in this digital world where there's no end to your inbox. It can just keep filling up and filling up. And that’s not how we work in the real world, you know, we have constraints. There's only so many things that you can focus on. And so getting those two things in synch actually is, I think, you know, people just love it, they gravitate towards it.
It makes sense to them. They can see it. It's very much like the real world metaphor that people are using, whether they're putting these notes on their refrigerator door or if they're in their office putting them on their whiteboard.
John: I love the phrase that you used, is that we can do more if we restrain ourselves. And I think Fire Nation, if you really absorb that and take that in, you’ll realize the power behind those words. And Michael, what I’d kind of like to do here is detour just a little bit, because one thing that I've kind of been interested about recently is companies like yours, how they kind of arrive at a pricing model?
And I know that our listeners are looking to build products, services, SAS companies, pricing is always a struggle. It always has been and it always will be. What are like some conversations and some things that you’ve done to get to where you are now at Trello?
Michael: John, this is very timely for you to ask this question.
Michael: And just sort of looking back on our mistakes, this is something actually we're thinking about a lot right now, and I wish that I could just tell you that it was easy and it was obvious. One of the things we're doing recently is looking at our competitors and people that are in sort of complimentary spaces to us and looking at their models. And every single one of them has a different model. And I think that sort of tells you there isn't an answer to this. Like, it's a lot about experimentation and feeling out what fits your product and what you feel is right, and then going with it.
Like, we initially when we launched Trello, we just wanted – we had people that wouldn’t use it because they were afraid that the company wasn’t going to be around because they didn't have to pay for it. Trello is free and we sell premium services for it, but before we had the premium services we would just put out there. And we were like don’t worry about it, we're gonna get venture funding, we're gonna be around. And people wouldn’t actually use it. They were like that’s a constraint – or that’s a friction point. I can't use it because you're not letting me pay you.
So we basically said: okay, quick, code something up so that some people can pay us because we don’t want people not using the product because they can't pay us. And the idea –
John: But I get that though because if a team is gonna take time and invest in learning something, like they want to know that what they're doing is worthwhile.
Michael: Oh, yeah, and you see – I mean, this was around the time that Google had ranked – or yanked Google Reader out, and that was a much loved product and they just aid: oh, we're gonna kill it because it's really not important to us. And everyone was kind of like: are you kidding me? Like, that was part of my workflow. I really used it and loved it. So we came up with some premium services that we called Business Class, and we allowed people to pay for it. And essentially we didn't even think about the pricing model. We just said it's one flat fee per year. It doesn’t matter how many people are using it.
And as time went on, we had some companies that were paying us $200 a year, and they had 600 people using it, and they were running their entire company on it. And then we had other people that had four people that were using it and paying us $200 a year. And we realized that our pricing model was just not going to work because it didn't scale for big companies. It wasn’t actually working with the value that people were getting out of it. And so we switched to a per user model, which is kind of obvious.
And we looked at price points for products that were SAS based that were kind of in the same field that maybe were competitors, or maybe were complimentary, like Slack is complimentary, I think. You know, so that’s where we came today, but even now you think about it and we look at big huge companies now are using Trello, where it started as a couple hundred people, and now it’s just spread throughout the organization. Big companies don’t really want to pay per user. They're happy to pay you a lot of money, but they just don’t want to be counting every time they have to pay for another person because they have thousands of people using your product.
So it's yet another iteration that we have to go back and look and figure out what are the pain points, talk to people, do they understand what we're selling? I mean, one of the things that we realized was even when we were telling our sales people and explaining our products as we hired them, they were having a little bit of trouble figuring out exactly how this worked. And so that lead us to realize that: hey, let’s go look at these pricing models and clean them up a little bit, so that the end users can really understand them.
John: This is fascinating. I know that Fire Nation is really taking this in because it is a struggle. It is evolving, it’s ever evolving. And how you are going to start doesn’t mean that’s how you're going to six months from now, two years from now, and definitely not how you're going to be when your product continues to evolve and have more add-ons and such. And this is really cool stuff, and Michael thank you for kind of giving us a glimpse into your evolution for sure it's been fascinating.
I have a couple more really key questions for you in the lightning Round. But before we get there, let’s take a minute to thank our sponsors. Michael, welcome to the Lightning Round, where you get to share incredible resources and mind-blowing answers, sound like a plan?
Michael: All right, let’s do it.
John: What was holding you back from being an entrepreneur?
Michael: I think finding the right partner was what was really holding me back. I don't really have any great advice on that other than I just found him, and I've had a great business relationship for the past 15 years with my business partner.
John: What's the best advice you’ve ever received?
Michael: It's trust your gut. And I think going back to the idea that you're never gonna have all the information to make the perfect decision, you just have to move forward and keep moving forward, so just trust your gut and make sure you make a decision.
John: What's a personal habit that you do have that you believe contributes to your success?
Michael: I am a passionate user of our own product. So one of the ways that I keep myself organized is I use Trello. It allows me to get perspective on everything that’s going on at both in my business life and at my home.
John: Love it. Do you have an internet resource, like an Evernote, like a Trello that you can recommend to our listeners?
Michael: Actually, there's a series of videos that Sam Altman from Wikometer did called How to Start a Startup, which I listened to recently, and it's at startupclass.co. It was really eye opening. It talks a lot about things that it would be interesting to your audience, I think.
John: Startupclass.co. And if you could recommend one book for our listeners, what would it be and why?
Michael: There's a book called Influence: The Psychology of Persuasion, which is about the ways that we persuade people to do things that we want. And I think it's a really eye opening book for somebody that doesn’t come from a sale background to sort of understand the way that people influence each other.
John: James Cialdini, amazing book Fire Nation. And I know you love audio, so I teamed up with Audible. And if you haven’t already, you can get an amazing audio book for free at eofirebook.com. Michael, this next question is the last of the Lightning Round, but it's a doozy. Imagine you woke up tomorrow morning in a brand new world identical to earth, but you knew no one. You still have all the experience and knowledge that you currently have. Your food and shelter is taken care of, but all you have is a laptop and $500. What would you do in the next seven days?
Michael: So on the first day because I have a 2-year-old and a 6-month-old, and I haven’t slept in probably about two years, I would just sleep in, take a long nap and do nothing except recuperate. And then, you know, if I don’t know anyone and I got a laptop and I can write code, I'm gonna build a social network.
John: Going to what you know and love Michael, that’s not a bad place to start, but always following it up with sleep. I love that. And let’s end today on fire, with you sharing one parting piece of guidance, the best way that we can connect with you, then we’ll say goodbye.
Michael: My piece of my guidance would be if you start a business, use a PEO, look it up, it's a service that you can use to employee people and take a lot of the overhead of the operations away from your focus, so you don’t have to worry about those things. And if anybody has any questions for me or they want to give me feedback about our products, I'm happy to talk to you. You can Tweet me @ Michael Pryor on Twitter, or you can just send me email at [email protected]
John: Fire Nation, you're the average of the five people that you spend the most time with. And you have been hanging out with Michael P and JLD today, so keep up the heat. And head over to eofire.com, just type Michael in the search bar. His show motes page will pop right up with everything that we've been talking about. Again, you can Tweet him @ Michael Pryor, or email him [email protected] Michael, I just want to thank you for sharing your journey with Fire Nation today, for that my friend we salute you, and we’ll catch you on the flipside.
Michael: Thanks John.
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