What's up, everyone? This is Courtland from IndieHackers.com, where I find the founders behind profitable internet businesses and I try to get a sense of how they got started and what's going on behind the scenes, so that the rest of us can learn and build our own successful businesses.
Today, I'm talking to Jesse Patel. He's the founder of a really cool productivity app — one of my favorites — called WorkFlowy. I just logged into WorkFlowy today and it said that my account is 365 weeks old, which means that I joined in November of 2010, right after they launched.
It's not often I get to say that I was one of the first users of a product, and even less often that I get to talk to one of the founders of that product, so I'm super excited to be talking to you, Jesse. Thanks for joining.
Yeah, totally happy to be here.
There isn't much written online that I could find about the origin of WorkFlowy. Just a few articles here and there. But from what I could find, it seems like it's intertwined with you teaching yourself how to code.
Maybe a good place to start is: How did you teach yourself to code, and why was that something you even wanted to do?
So, I think… I've kind of been teaching myself to code for a long time. I took some computer science classes, just like one-and-a-half, at Stanford when I was there, and it was like probably the thing I enjoyed the most but I just was… It was the first time I had done it, whereas everyone had been doing it since they were 12. And so I was like, "Okay, I'm not going to do this." From my first exposure, I liked the process of running into confusing things and having to fix them. Some people don't like that.
For me it was like, "This is just a fun puzzle and I really love to build things. I was trained as a product designer and building stuff is super fun. Coding let's you just build stuff yourself that other people can use in a really, really rewarding way. That was my motivation in general, so I'd been fiddling with it for years. Then at some point I had stuff I really wanted to build and I was like, "I'm just going to start building this." Actually, that was WorkFlowy. It was like a teaching-myself-to-code project. Everyone thinks they can make a better note-taking and task.
I'll just waste that idea on learning to code because obviously it's not actually a good idea. Everyone thinks they can do it better, but why would I be any different so I'll use this delusion to learn how to program. Do you want me to talk a little bit about the motivation for the product itself or just the coding?
I think it would be good to hear about the motivation for the product itself because like you said, everyone wants to build a to-do app. Everybody has their own unique styles of working and none of the existing tools match perfectly with what people want, and so there's tons of tools out there.
So what was motivating you? What did you not like about existing tools and what did you want WorkFlowy to do better?
Basically I had this in 2000… It was a long time ago, 2008, I think. I was knee-deep in this job that was really complicated and I was basically the person in part in charge of the business development for a nonprofit tech company that was trying to decentralize video. It's kind of like an activist project and they were trying to figure out like how do we make money? Is there a way for us to make money in a business sense as opposed to raising money from donors which is what they had been doing?
We had 4 million active users and so there was an audience, and we were trying to figure out, "What are the different ways we can monetize?" There were like 30 different legitimate things to explore, each of which would have a department at a real company or whatever. Everything from selling independent — it was a video thing — so selling independent films, to advertising, to customizing and selling the software itself to other people who distributed video. There were many different avenues to explore, and each of them was really complicated.
I was just cycling through product management to-do note-taking apps trying to keep track of all the complexity and getting really overwhelmed. I was going over everything, everything, everything and the thing I started using was Word outline mode.
I was like, "This is kind of the best, but I need it to be able to zoom in." This was like… I need to be able to in Basecamp or any of these other tools, they have a set structure and there always comes a point where you have a to-do that's like "make marketing proposal". Then you're like, okay, I want to write out the ideas for that marketing proposal, but I can't do it inside this to-do. It's *in* this to-do, it needs to be there. Basically, I just had this sense that I needed something fractal and that went in forever.
Then having used the outline mode, I was like, "Oh, outlines are useful." This idea of combining what I knew was like this need for a fractal thing with an outline thing. The first version of WorkFlowy I built actually didn’t look like an outline at all. It was like more of a standard task list type thing that had… It looked like the McFinder with columns mode.
I saw a screenshot of that online. It was just like columns and then you click on each row of a column and it opens up another column to the right. So you can kind of zoom in, but it was just different.
It was different. It was pretty cool. Actually, do you know the company NewsCred?
No, I don't.
It's a big company in New York. They're a media company. They have hundreds of employees. My friend, Shafqat started it right when I was first working in WorkFlowy and he used that version of WorkFlowy. It was like the columns to start NewsCred which is hilarious.
He's the only person who used that. I'm using number one, he's number two and he's the only person who used that version of WorkFlowy ever.
He must have liked it if he started his company with it or was he just doing that as a favor to you?
No. he was using it legitimately himself. I mean it didn't have collaboration at that point so he was using it as a private project management/task management tool. He liked it a lot.
That must have been pretty inspiring to have somebody who was really using your tool. How seriously were you working on WorkFlowy at the time?
October of 2009, I quit my job because that kind job was impossible. I loved the people and I'm still super good friends with all of them but it was just this job where I felt like I was feeling because it was like none of these business models are basically working out. None of them seem like the arrival.
Anyway, I quit my job and I was like, "Okay, I'm going to go full-on with WorkFlowy." It was four months or so of just solid working on the product and I had a prototype that I had been using before I quit that job. I quit the job thinking like, "I'll work on WorkFlowy but really I just wanted to start something. This segues into Mike and recruiting my co-founder and stuff. Do you want me to go into that?
Sure! Today, you're working on WorkFlowy with Mike but how long were you working on it before Mike came in to the picture.
Basically since I started playing with it in 2000 before I even moved to Geneva, I started like I'm going to learn to code so I can build this thing. Probably it was 2008 that I started working on it a little bit. I mean it’s really slow when you're learning to code to make something. It was 2008 and in 2009, early 2009 I started doing a lot of work on it. It was June of 2009 that I started really working on it. I was in Berlin at the time working out of the SoundCloud offices.
How did you end up meeting Mike and deciding to work together?
Beginning of 2010 basically. It was like nine months after I really started working. I had something I really liked, I had a couple people who were using it and they really liked it. I was starting to go insane. I remember reading… I think it was like Naval had just launched Venture Hacks or something, or he hadn't just launched it, I had just discovered it rather. I had just discovered Venture Hacks. It was like end of 2009 and I was reading out voraciously all these articles and Hacker News and all this stuff.
It was like the dawn of the era of entrepreneurs writing honest things on the internet about starting business. Both Venture Hacks and just Paul Graham's stuff was like, "Find a co-founder. You're crazy if you don't find someone to work with."
Plus, I was having the sense of like, oh, I'm a very beginning programmer here. I'm running in circles a lot. I have no idea what I'm doing. I was like, I really need someone who's actually a good programmer to work with me and I'm just to go insane working on my own. So I just emailed two friends in probably December of 2009, and I was like, "Hey, I want to start something. Do you want to start something with me?"
One of them was like, "I just started something with another friend." These are two friends who I knew were technical and who were not working, and had just left their jobs. And the other one was Mike, and he was like, "This is a good time. I was just starting to think about what's next?"
Mike I knew from college. We lived in the same dorm. We'd been friends for a number of years — we met probably in 2002. But we weren't super close friends. We were just friendly and in the same friend groups, so we'd see each other out and see each other at other people's houses, and we'd chat and catch up like, "What's been going on for the last few months or whatever?"
Then he just said, "It sounds good." We got on the phone and I talked to him about WorkFlowy and he said, "Not interested. Let's work on something else."
So we started working on and brainstorming other ideas, and we settled on a general area that was very different than WorkFlowy which was basically helping self-help gurus build ways for other people to follow their advice through an app. So basically, if you write a book saying, "Here's how you start your business or here's how you get a six pack in 100 days," we basically have the actions that you're recommending people do and a way for them to track whether they're doing it, and a way for you to engage with a community of followers, and all this encapsulating people's advice in an app.
If you've published a book, the idea was that it would come with an app and a website that would help people actually do what you're suggesting they do.
That was the idea we were going to work on and we're starting to work on it and then I was like we're going to apply for YC and Mike was like… He wasn't super psyched about that idea and I just… He wasn't against it, but he was just like, "Whatever." I just applied for YC. I also decided at the time, I was living in Geneva, Switzerland because my now-wife, girlfriend at the time, was living there.
I decided if I was going to start something, I needed to move back to San Francisco and be near Mike if we were going to work together. Then once we got into YC, it was like, "Oh." Actually, I think I already had moved back at that point, so I guess YC didn't fit into the picture. I just knew I had to be back and I wasn't super happy in Geneva.
Why weren't you guys working on WorkFlowy? Why wasn't Mike excited about the idea? Because it seemed like it was something that you had poured a lot of time into and had some preliminary users?
I mean I actually only had a couple users. It wasn't like I had a lot of validation at the time. And I think Mike's reasons were the same reasons that I thought it was like a throwaway project. I was rationalizing to myself that I didn't think it was a big deal because everyone thinks that they have the next big idea for how people organize themselves and how you could track your information and stuff. So it's like, I don't know?
And he's a guy who uses simple tools where he's like, "I'm happy with a text editor. I'm not trying to find the next new weird thing." I think that's basically why. He tried it. He was like, "I'm not that excited about this." And the area was also an area that he found very uninteresting.
Honestly, the rationale makes sense to me for why he didn't want to work on it, so I didn't exactly fight it. At the same time, I kept working on it and eventually it is what we ended up working on. I had conviction around it.
I mean it sounds like it's a tool that you were making for yourself more than anybody else at least. You wanted to keep working on it, which is cool, because it gives you a lot of insight as to how good the tool is. You're eating your own dog food which is some of the most common startup advice out there.
Anyway, I'm really interested in hearing about your experience at Y Combinator. Were you at all nervous about getting in?
Yeah. I was nervous but I think I was pretty confident we'd get in.
How was the experience of actually going through YC for you guys? What'd you think about it at the time?
I have two somewhat… not contradictory, but different angles on what it was like doing YC. One was that it was really unpleasant because they basically hold your feet to the fire and they're like, "You have to accomplish something."
And then Paul Graham is just really frank. I mean he's not in charge anymore, but he was just like, "I think this is a terrible idea."
He's really frank.
He was just like, "I thought you guys were great at the beginning of YC and now I think you're idiots for working on this." He'd be like, "I've seen a million online collaborative whiteboards and this is not going to go anywhere. What makes you think you can do this better? There's no special moment for this or whatever."
Yeah, Paul Graham can be pretty frank. It's really helpful at times and it's also really soul-crushing at times. I remember he told my co-founder and I that one of the ideas we pivoted to was the worst idea ever, and that they always reject companies who apply with that idea, so that was rough. But anyway, what were some of the good parts of YC for you?
I don't think WorkFlowy would exist without Y Combinator. That's one part. It wouldn't exist, and no one would know about it without Y Combinator.
The reason it wouldn't exist was because Mike and I entered Y Combinator with this idea and we were halfway through. I think almost immediately we realized that the original idea wasn't… We didn't want to work on it because it was too dependent on basically the publishers and the self-help gurus who were the people who were going to basically be writing the advice and publishing something in building an app with our thing.
We did a talk with Tim Ferriss and we talked to a couple of other people who just did, who were the kind of people we'd want to target and we realized that they just weren't going to care, they were going to be those kind of semi-invested people who you'd have to be fighting to get their attention and then all your promotion would depend on them and all your content would depend on them. You just would have no ability to independently… You basically wouldn't be in control of your own destiny is what I felt like. It's a two-sided marketplace where one party, not us, was in charge of both of my sides.
Again, this doesn't feel like a good idea. Then we were floundering around just experimenting with different things. We played with making a bunch of Facebook apps and we played with a couple of ideas but as soon as we decided that wasn't a good idea, I think I started lobbying Mike to start working on WorkFlowy because a couple people on YC had started using WorkFlowy and they really liked it and they were like, "Here's what needs to change about it. here's what's good and here's what's annoying." I was like, "This is further validation and we had nothing to work on right now." The other thing was Mike started using it and he was like, "Oh, I see how this is cool and how this is different." At this point, I had already rewritten it to look like a piece of paper until it worked like an outliner as opposed to the comms thing. Basically we switched half way through YC and actually didn't even tell. There's this thing at the time called Angel Day I think like Angel Demo Day. I don't think it happens anymore but we actually didn't tell anyone we were working on our WorkFlowy until we gave the presentation at Angel Day where we're presenting WorkFlowy. Everyone in YC was like, "We've never heard that before until you just presented it to everyone." We were like, "Sorry."
Sorry about that. Were they excited or were they upset?
No, they weren't upset. It was just, I think, funny. I think they thought it was funny. No one was upset. They were like, "At least you're working on something. You've been doing cats and dogs better apps on Facebook for couple weeks now, it seems. Nothing can be worse than that."
I think one of the cool things about WorkFlowy is it's like super innovative and super compelling because you invented something that was completely new. I mean there were other outliner tools but none of them really looked like WorkFlowy or worked like WorkFlowy and I think having that extra step of having to teach people how to use a product kills a lot of companies but it worked out for you.
I mean it took Mike a while but he eventually came around and decided that, "Hey, this is pretty cool." People in your batch also realized that it was pretty cool. I even remember reading a review from years and years ago about WorkFlowy were somebody called it, basically the best note-taking and organizer program that they had ever come across which is pretty high praise and I felt similarly when I first used it too so I'm just curious what makes WorkFlowy so good. Maybe you could describe it for people who never used it.
Totally. Before I do that, I forgot the second part of the question for the YC thing because we're not people who promote things and I'm not a marketer so I would like to be but if WorkFlowy had never gone through YC, we would have three users. They would have kept using the product and they would have eventually maybe stop. Once we launched YC, it just gets you on TechCrunch and Lifehacker basically. Then on day one, we had 10,000 people using it and they didn't stop using it.
They were like, "Maybe this is real." before we had a couple of hundred people using it but it didn't feel like… It wasn't obvious to us that it was an opportunity but then once we had a much larger number of people using it which we would have never gotten, I never would have even emailed TechCrunch. I would have just been… It's a character flaw of mine. That was huge. Just that alone made an enormous difference. Anyways, pitching WorkFlowy is probably my greatest weakness.
WorkFlowy is an application people use to organize all the information in their life, in their work and it becomes their hub. It's open on average for 11 hours a day which means people just have it open. It's like Gmail. People have been using it on average like our average active users have been using it for almost three years.
Two years. Which is a testament both to how useful it is to people but also to if we were growing super fast that would not be true. What it actually is, it's basically infinitely recursive bulleted list. A bulleted list where you can just dive down into any section and focus on that. It basically means you have a huge pile of information that is manageable at a human scale where you can slice it to see one part of it. You can also do tagging and searching so that you can just slice down your huge pile of information that hopefully has everything from all aspects of your life and then just see the one that you need to see and have it be kind of just easy to mess around it.
I think what's really special about it is it lets you create… That's one part of it is this lets you focus but the other thing is that it lets you create structure in a really low friction way. When you're using WorkFlowy, you just by default create some structure and you don't really have to think about it because it's bullet points but at the same time all other apps do for you like all the apps that are special CRMs or whatever, they're basically letting you create a structure. They define the structure for you like, "Your leads go in here and then when they're moved to this thing, we move them into this other… You click a button and you move into this other list."
Basically most software is list and moving stuff around lists and responding to when things move in to different lists of different categories in some sense. What we do is basically let people define software for themselves that works exactly how they want. It has a structure that's perfect for them and for their unique situation. I think that's what is really special about the product and also partially what makes it hard to really grok is that people have to say, "I have to figure out the right structure for myself." In addition to entering content, I have to be thinking about structure and thinking about how do I organize this? You don't have to and that's also… Structure just happens as well so that's cool.
I think the first time I used WorkFlowy, I got it instantly after I created a few bullet points and zoomed into one and then it took over the entire document and that bullet point was down to top level. I was like, "Oh, okay. This is an indefinitely deep outline where I can put literally all of my information in this one document and it will never be too much because you can always zoom in and zoom out." Which is really cool because then you can organize things and reorganize them really easily unlike in Google Drive or something where if you mess up your folder hierarchy.
You're never going to go back and fix it because it's too much work but if everything is in one document, you can easily copy and paste it so it's super cool and I understand why it really resonated with some people and fit into their working style in the way that other tools never did. Let's go back to your story at YC. You might not remember this because I barely remember it myself to be honest but I think we actually met briefly way back in 2011 at YC headquarters because you did, I think you were summer 2010, right? I was winter 2011 with another app called Taskforce. I think you and your co-founder, Mike may have come to my classes demo day. Do you remember coming to that or am I just making that up?
Yeah. I remember. I came to the demo days back in the day for sure.
Yeah. I remember talking to you guys and I think one of the cooler things about workflow is that you guys never raised money after YC. Now, it's increasingly common to just start a startup without raising but back then everybody wanted to raise money. I remember meeting you guys at YC because you guys were some of the few people who just didn't seem to care about it. I also met Kevin Hale from Wufoo who came to give a talk at one of our YC dinners and I was blown away by the things he talked about and how successful they were and how they also didn't care about doing the things like the conventional way. Also, the Basecamp guys stood out back then. I'm curious what was driving you and Mike to go alone and be independent and not really care about raising from investors?
I think there are a couple of things. One was that I don't invest… We did talk to some… We spent a couple of weeks talking to investors after YC just because it's what everyone did and no one was interested because what we were doing was weird and hard to explain. It hadn't launched so we didn't have lots of users. I think if we had started raising like a day after we actually launched, we would had success. We did try is the answer like in the beginning just because okay I guess we should do this, everyone is doing it.
We didn't really want to but we just felt pressured too. Then the further along we got, we were just like I don't like authority and I don’t like the idea of having bosses who aren't me. That's why I didn't want to raise money. Also it's all the stuff that people say about it reduces your outcomes, the scope of your outcomes a lot. If you raised money at whatever valuation, it means you're like the minimum at which if you sell it at that exact evaluation it's a failure.
That's a failure.
If you suffer 10 million, you raise 10 million, you sell at 10 million. It's like a huge failure. Basically, that's one of the big reasons like basically not having a boss and minimizing the range of your possible outcomes.
The downside of not raising money is that you have to make money on your own. You're still living in San Francisco or the Bay Area, you're still paying probably ridiculously high rent. What did your financial situation look like at the time? How were you guys surviving? What were you charging for WorkFlowy?
This is one of our big areas of… One of the biggest issues between Mike and I in the early years was… He was like post-Google and he made tons of money at Google and he had all the stock. I was post working in a nonprofit and basically I spent all my money paying rent, then my girlfriend at the time basically just was paying rent of us, but we had enough users and they kept telling us they wanted to pay us.
After a couple of years people started paying and it was pretty early on like we had significant revenue pretty quickly. People were willing to pay us so it was enough to pay rent and stuff. Basically like we just got really lucky and that we never did marketing and people would just write about the product because they loved it and we got a couple of really big people writing about it and then we’d have a lot more users and then people use it 11 hours a day so other people see it over their shoulders and then they're like, "What's that? That's weird. That's cool. I'm going to try it." Basically, we've just been very lucky and that the business has supported our and lazy approach.
It's entirely product-oriented.
It's just entirely product-oriented.
That's really cool to hear about. I'm curious about the early days of living with really no funding and just having your girlfriend pay for things and trying to charge. What was that process like at first putting a price tag on WorkFlowy and how many people signed up to pay initially?
Let me look at our graphs.
You guys started charging after you launched, right? This influx of 10,000…
We started charging two years after we launched.
Okay, so much, much later.
This is after I spent all my money, I was like, "Mike, we need to start charging." It wasn't on his radar and I was like, "Please," and he's like, "Okay, fine." It was just like… What we did was we… We were just wimpy people. What we did was we're going to grandfather every one… We're going to set usage quota which is 500 bullets a month you can add for free and then we're going to email everyone who was above that in the last few months and say, "Hey, we're going to launch a pro thing. You can have it for free but please pay us anyways."
In the first day, almost 30% of the people we sent that email to signed up for pro. We were basically immediately making a decent amount of money. It was just clear that people wanted to pay us. They wanted to support us. They wanted the product to get better and to survive. It was stressful and for me it was… Honestly, for Mike, I don't think it was stressful not making money from the product. For me it was stressful because I spent all my money. Then once that happened, I think it was clear that this was the real thing.
Why did you guys for two years without charging? What was your game plan? Do you feel like you were going to get millions of users.
Honestly, it was just like whenever I brought up the conversation, it was just not… It didn't feel like it was a priority for… I mean first of all, there was a period where we didn't have enough users. It would have made a huge… It would have been a lot of money so basically once we got to the point where it's like, "Now, we have a lot of users and we can probably… " If we think about how much we can make it probably would be meaningful.
Then it became the question of like, "For Mike, it wasn't a priority. He was just thinking all that matters is getting a lot of users and they're willing to pay us to make money. Then for me it was a priority because I didn't have any money. It was just a matter of talking about it together enough that he understood where I was coming from like… We had this conversation. It was like, "I didn't realize you spent all your money." I had no idea. Having those conversations which is actually… I don't know if you want me to throw in advice but one of the biggest things I would suggest people do if you're starting a new thing with any other humans is have a weekly structured conversation where you bring up any issues that haven't been resolved because issues that fester like something small can become something big.
Any accumulation of loss of small things becomes a terrible relationship so basically have a weekly conversation where you go like, "Is there anything that's bother you? Is there anything that hadn't been addressed?" and just deal with it and if it turns into a big, get some third-party to help you figure it out where it's some person you will trust or a paid coach or whatever it is because that's how we didn't end up charging people… That's how I end up spending all my money with it because he didn't even realize that I was spending all my money. You know what I mean?
There was just any communication.
I mean there was communication. It was like if you're really focused on building this thing together and then every once in a while, you slip in something that's really bothering you like you try to slip it in and it's not even heard because everyone is distracted and everyone… If we're communicating constantly about the product and about lots of things but there's this one thing that I'm like, "A little ashamed about it because I didn't have that much money to begin with."
My sense is that relationship issues are one of the biggest things and that biggest issues with companies and I mean I know that from talking from tons and tons of people is just that co-founder relationships are really difficult and I would just say like marriages like the ones that work are the ones who you address the issues, small issues before they become big issues. How to process where every week, you're just like, "Is anything wrong? Let's deal with it."
I'm dating a relationship therapist and she's taught me so much about exactly what you're saying. That's crazy to hear. I know that you and Mike, I listen to Mike's Mixergy interview from a couple years back and he talked about some of the challenges that you guys had as co-founders and how you guys ended up going to a relationship therapist.
Like a couple's therapist, not even a business therapist, yeah.
Which is I think a really smart idea because the problems are the same I mean you have this thing, you have this relationship that's just as close or almost as close as the relationship between a married couple or parents or something where you've got this startup that you're working on and it's your baby. It's the thing that matters to you most in life except like everything else in your life, this other person has a say and what goes on.
I totally agree with you that people don't talk enough about co-founder relationship issues but every startup that I've started with somebody else there have been low screaming fights at least once and now I'm now working with my brother where we've been doing that since we were kids so it's no big deal. It's super easy to recover but anyway on Mixergy interview, we got to hear Mike's side of things where he talked about the differences between you and how you really focused on moving fast and you were a little bit more risky and he was a lot more risk averse.
I think it would be interesting to hear your side of that conflict as well. What separates the two of you? What was hard for you about working with Mike and how did you guys resolve things?
A lot of the things that were difficult are similar things that are difficult with my wife to be honest. It's funny for me to see it's not just them. One is that I am impulsive. I would say I'm impulsive and Mike is the opposite of impulsive. It's extremely deliberate. I'm probably not deliberate enough. Mike is too deliberate, I'm not deliberate enough. I just want to think of things and do them and try them and Mike wants to think about them probably longer than he needs to which we've both talked about this. We both agree that that's overall probably true for both of us.
That's part of it. That's a bigger picture strategy thing but I think almost as big a part of it is just like working styles. I always just wanted to talk about what I was thinking about and then this is the same issue that I have with my wife is that which I'm sure she'll really appreciate me talking a lot on which is that I have an idea and I just want to talk it through whereas being a deliberate person you think like this person is talking about something. That means they want to do it or it means I have to really think harder about this whereas I'm just going to talk about 30 things a day which I don't even think are good ideas. I just want to think it through. Just throwing stuff out there.
Just throwing stuff out.
For Mike, he have this… A, he like… He's like an intense programmer. He wants to be, here's what we're doing and I'm going to do it and I'm going to focus on it super intensely and also he's working on technical, hard technical problems so he needs to have his… Being in the zone, not be interrupted and there's this dude interrupting him every half an hour to talk about some stupid idea. I think that was honestly a huge part of it where I would be like, "Hey, should we this, should we that? Hey, what do you think about this? What do you think about that?" and him just being like, thinking, thinking, thinking, thinking. A person talking to me again. Let me work.
Stop interrupting me.
Yeah, exactly. I think that was a big part of it. There was also just working style. It's like I really want to work together in a sense of I like pair programming is a good example. I love looking at the same screen as people and doing things together and he doesn't. He just likes to be in his own world and think really hard about things. He's brilliant. He makes great decisions and so it's like I can't for that but he doesn't like to be working in real-time together basically.
He likes to talk about things ahead of time and then go apart, and do the things you talked about individually. It's just like working style things both being interrupted all the time and that difference around how you wanted to work day to day. It just led to us feeling… I think both of us feeling very neglected and leading to conflict because it's just like our needs weren't being met. I would bring up stuff over and over again in the way.
I would just be pushing at him a little bit because I just wanted that interaction. I'm extremely extroverted person. I just wanted interaction and he would be frustrated because I could be taking amount of his flow slash giving him ideas that he's not even sure if he has to really think about it or not. I mean does that make sense?
Yeah. It makes perfect sense. I mean you're describing anyone who has any close relationship with somebody has some ways in which they're different and they're going to wrap up against each other and they're not going to be able to talk about… They might neglect to talk about exactly how they're feeling underneath. It's so easy to misinterpret what the other person is doing and sometimes just listening to how the other person feels without getting defensive or fighting back is going to help to make them feel a whole lot better.
It's super hard to do that especially when you're implicated in making them feel bad. It's just really hard to hear I've done something that makes someone else feel bad. I think these are really like… Those are the dynamics and then the fact that we never really dealt with them was the problem. I think all those dynamics were fine and then they just built up to this point where we went on this walk. I remember the walk really vividly. We were working out of my friend's company and we walked to Dolores Park. We sat on this bench.
I just remember Mike saying like, "I don't think I can do this anymore." Both of us being miserable. I was not thinking about stopping but Mike was just like, "Look, dude. This is really unpleasant. We're just fighting. Every time we talked, we're fighting basically." I was like, "This is really broken." Then we went to therapy and it was helpful. We stopped therapy way too early because I was feeling very heavy pinching and it's not cheap. We should have just never stopped going to therapy.
Do you think that the tools that you learned in therapy have been helpful like up until today because you were mentioning earlier about how to check in with each other and have conversations on a weekly basis?
It helps a lot, yes. We went back as well later.
I don't want to spend the entire episode talking about co-founder issues but I think it's really good to bring it up because like you said earlier there's a tremendous amount of advice out there that says you need to find a co-founder and that'll be more likely to succeed as a co-founder but it's important to look at the other side of the equation as well which is that a tremendous percentage of companies fail because of co-founders issues and co-founders not getting along so it's a double-edge sword and I know personally I've been in a situation a couple of times where businesses I might have otherwise done well failed because of my relationship with co-founders.
One of the cooler things that I think you brought up earlier as well is the metrics behind WorkFlowy, how long people use the app like 11 hours a day how long they stay an average of three years. Were things like that right out of the gate right when you guys launched on TechCrunch and Lifehacker early on, did you guys have a really high retention rate or did it take a lot of work to get to the point where people loved the product and were loyal to you?
We improved the number of but basically for a long-time it's been a business for a small percentage of people who actually get it but then those who do get it basically has never stop using it. It's been like that from the beginning and that basic dynamic is what… The number has gone up as we've entered the product. The numbers have all gotten better. The basic dynamic has been there. That's why we were like, "This is the real opportunity," because on day one, we had 10,000 people using it and then they were telling other people about it and as people dropped off we were replacing them with new people just through word of mouth and it grew… It was just growing on its own. It's been a really high retention product from the beginning.
It's pretty inspiriting to hear because I build a couple productivity tools in the past to you and retention is so hard with productivity because you're essentially building a tool to help people do work, do things that are effortful. If you're browsing Facebook, it's fun. You're addicted to it but if you're putting tasks into Asana or you're making an outline in WorkFlowy about things you have to get done or other forms of work then that stuff that people might just fail to do all on their own even if people have a great product because they lack the motivation and that's effortful.
It's always going to be harder to sell health food than tasty, delicious fast food. It's pretty impressive that you guys have such a high retention rate and that you've been able to grow your user base like you have. What does your stats look like today? I know you guys aren't perfectly transparent about everything but just ballpark how much revenue you guys are generating and how many people are using WorkFlowy?
We are at about 800K in run rate right now. We have over 100,000 active users which just goes up slowly.
Who all is working on WorkFlowy? Just you and Mike?
Yeah. Basically, that's the area that's in the biggest flux right now so about a year ago… For a while… Many users noticed this. For a while not much was happening except for us maintaining things and doing infrastructure stuff as the user base group but about a year ago I had basically twins like three-and-a-half years ago and I was like I'm going to take it easy for a while and hangout with my kids and just do what's needed. Then about a year ago, I was like I really want to make… I feel like WorkFlowy is this huge… Both something that I really love and want to have a vision for. I want to make it realize that vision and also just a huge opportunity that's mostly unrealized because it has relatively small… It's like reaching just a drop of potential people it could reach.
Just everything is so much smaller than I think it really could be. About a year ago, I had that realization and started talking to Mike about it and so basically over this current year I have basically been… We just started building team and hiring people and doing stuff. Now, I have three… It's me and I have two other full-time employees who aren't Mike and several contractors who are doing a lot of work and we're just… It's like we're ramping up and starting a startup.
That's cool. It's pretty exciting. I think you guys are in such an interesting position because 800K annual revenue is a ton. The vast majority of people I talk to aren't making anything like that with such a small number of employees. You've got that going for you. You've got the freedom to work on basically whatever features you guys want to, whenever you want to and obviously from wherever you want to. You got a lot of diehard fans. I mean you're not Tom Cruise but people like WorkFlowy and you guys have a following. I'm curious what is driving you? What do you want WorkFlowy to be? It sounds like you really want to grow? What underlies that and why do you want WorkFlowy to be big?
It's not that I want it to be big, it's that… I think it’s the craft's person's motivation which is A, there's this thing I made which I love but it feels like it's in a lot of ways like 30% of what it could be. I just want it to be what it could be. Then there's this full other angle which is there's this thing… That's a huge part of it. I just want this thing to be what it can be and realize its potential. I know there's all this people who love it for whom it changes their lives and I want that group to be a lot bigger. I know there's just a lot of people for whom it could be a very important part of their lives and it's not right now. Not just because they haven't been exposed to it.
I know for a fact there's a ton of people that's super common that someone tries it for three times has no idea and then someone shows them how to use it or they have some insight and they become a diehard fan. I just know that we are… I just have overwhelming anecdotal evidence that the opportunity is so much bigger than what we realized that it's quite motivating.
What are some of the things you want to work on and how do you plan to get bigger and better?
There's a lot of angles. Being very product-oriented like I would love to continue to have a product that grows itself. My sense is that the product is holding is back in a lot of ways but also the fact that you've never done any marketing or outreach or anything is also silly and that we need to do that but my personal motivation like the area I'm focused on is how do we make the product stickier for any users so that they have a higher percentage of the average new person who comes to WorkFlowy. We have 20,000 new sign ups a month from word of mouth and then… Think about it. Only a few like maybe a thousand of those people actually become real users like long-term users who use it for many, many months or whatever.
That's 5%. What do you consider a good percent for retention?
For long-term retention, I'm not sure but I just know that products that do really well, do a lot better and I know that most people who sign up… Not most people but half the people who sign up don't even create a single bullet on the first day so I just that we're failing in a pretty profound way. Basically, that's part of just making the current product more obvious how to use it. There's lots of obvious things that need to be done, lots of features people been asking for years like mobile being better and mobile having all the features of desktop, mobile being actually designed for mobile is a huge thing.
Improving how collaboration works so that you can actually have a team that really stays safe to keeping all their information at WorkFlowy is a huge… That's probably the biggest strategic thing. There's basically like make their product better so dates and reminders, mobile, all that stuff. All the stuff that everyone wants and all our users want and they've been telling us they want for ages just like getting product and making the product better is a huge part of what I want to work on or what I think will make it stickier as well as having new user experiences that are customized for all the different ways to please WorkFlowy and letting our users create those experiences for other people.
Then the collaboration thing is just massive. That's the biggest strategically important thing. It depends on the product being great but making the product so that when I open WorkFlowy, if you have wanted my attention on something it will draw my attention to that. If you have something nested like 30 levels down, and you're saying I want Jesse's feedback and you should be able to tag me and then the product will show it to me. Likewise, if I want to just keep track on some projects they care about that everyone is managing in WorkFlowy, I should be able to do just open the app and see it or get notifications or whatever.
It sounds like you guys have a ton of work cut out for you and it's pretty exciting to listen to you list all these features because whenever I'm working on something I have this gigantic to-do list and I've talked about this before that never get smaller. No matter how many things I cross off that list and the amount of time I've added more things that I want to do and I'm sure the same is true with you. How do you prioritize? How do you know what goes to the top of the list and how do you figure out what which of your team members are going to work on which things?
Basically, there's a couple parts of it. One is reactive so what do people… This is a prioritization about who's going to work on what but part of it is just like, "We get a lot of feedback from people and we have a lot of really passionate users. They tell us what they care about. Mobile being better is really obvious. One of the things that's wonderful about working on a consumer product that is actually useful is that you end having a lot of friends who use it so you get a lot of anecdotal feedback and you can see whether that mashes up with feedback you're getting through your official channels but basically we get a lot of feedback and it's like this is obviously the stuff people care about and the stuff people want.
That's one side of it and there's also the vision part of things which is I have a vision for WorkFlowy and I have an aesthetic and I have all these things I want because I want them and because that's how I've always imagined that I want WorkFlowy to be this shared… A lot of people… Probably a lot of our users don't care about collaboration in WorkFlowy. They probably… A lot of them do it. I know that for a fact but I'm sure a lot of them are like, "This is my private tool. I don't want to share it with anyone."
For me the fact is like I've always imagined it being the way you can have your brain and also share parts of your brain with other people. Part of it is just like vision and inspiration. It's like being an artist, here's this thing. Here's how I want it to work. Those mesh in terms of prioritization so if there are things when I overlap, I'm like, "I've always wanted this." I just think it's cool or whatever it is and people are asking for it then that's very… Sometimes it's like confirmation bias where I'm listening to the feedback that people want, that I want to hear from people.
It's like those two things play against each other because I care a lot about what people think and what our users want so one of my big things like if I was to give advice to someone, a new person is watch people like literally watch people use your product. Either physically or either video chat like just watch people use it. You just get so many insights from doing that and it gives you a very human view on your product and all the ways in which either it sucks or is great or both of those.
I just talked to David Darmanin, COO of Hotjar. I don't know if you've seen that product but it literally takes a little recording as people use your products. You can say, "I want to watch 2,000 people use my… Sign in and it'll take a bunch of recordings and you can watch it. It's not quite as good as sitting down with somebody in real life where you can ask them about what they did afterwards or they can talk you through what's going on but it's the same phenomena.
Those are great. That kind of product are wonderful and I would definitely recommend people use them.
I think another thing that we haven't talked very much about is marketing because WorkFlowy has grown so far, it that's entirely word of mouth which is amazing. One of the things that I tell a lot of people who are just starting out is if they should consider picking a niche and that way they can build something really valuable for a specific group of people and that group is more likely to fall in love with the product because it's built just for them and whereas the competitors tools aren't built more generally but for WorkFlowy, I feel like your product completely flies in the face of that principal.
It's not built for teachers or programmers or sales people. It's just a general product for everyone. I'm curious who are these hardcore WorkFlowy users. Is there a pattern that you've discerned among them? Are you guys trying to discern that or is it right now just it could be anybody.
I think it's a very interesting… It's a very interesting question and I think… To some degree we have built a niche product except it's not niche for a segment, for a specific purpose, it's niche for people who like to work in a specific way and people who are smart enough to figure out how to use a general tool. They're not smart enough. I think it's very smart to market to specific used cases. WorkFlowy is used by everyone from piano teachers to CEOs of public companies so it's a genuine… I'm not surprised if someone says, "My mom just recommended WorkFlowy to me." That happens a lot. I think it does skew techie a little bit but it's still a very broad product that does appeal to very wide array of people who would be hard to… If you saw them together in a room, you'd be like, "What conference is this? I'm very confused." I think that our… One of the biggest areas that I want to focus on in the future is making it so that you can essentially. If you are a piano teacher or you are a COO of a big company who needs to manage all of their one-on-one's or you are a customer… A client-facing… A business that has clients that needs to move through your pipeline that you can come to WorkFlowy and come to essentially a structure and something that feels like an app that is customized for you because I do think both for marketing and for onboarding, it is super important to show people how to use the product for their own purposes and in a way that fits into their own life.
I went to a conference last year, the biggest investigative journalism conference. I'd give a presentation along with some of the other people on tools and then I had a breakout session where 20 people came the idea was like how to create your hyper personalized organizational system in WorkFlowy. Of those 20 people, all journalist, one person looked at WorkFlowy and checked out the site and tried the demo and had their eyes go wide and say, "Oh, wow. I get this. I see how I can use this for everything. I can how I can use this for this part of my work and this part of my work and this part of my… "
Everyone else really needed to be shown how to use it for journalism and needed specific… They all the same needs and they all really needed to be shown. Right now, we don't do that and I think because of that we are missing out in a massive way. I was talking to one guy who's an investor, who was like I used WorkFlowy as an example. This is very none self-promotional here. An example of one of the biggest failures that I know of whether they've just left so much on the table because they haven't done… They have this product which has this kernel of something amazing but they haven't done anything with it.
They haven't promoted it and they haven't built it out to its potential. I tell that because I agree with it and that's why I'm doing all this stuff now and that's why I'm building the team. I was just saying like I think that that advice is good advice that you give people. I don't know. For me, I'm just… My entrepreneurial story is doing lots of things that I think are bad ideas and not working out.
You used the product a lot because you built something that works very well for you and ultimately if that doesn't generalize to some well-defined niche or industry likes sales people that's okay because there's lot of other people out there who think like you do. Apparently 5% of people and you could figure out how to make it appeal to other people and other specific niches later on.
Listening to you talk about the challenges that are happening, I feel super excited for WorkFlowy because there's so much low hanging fruit. It's not like you guys had spent 10 years trying every single thing and nothing has worked but you guys have done very little in some areas. Marketing and still things are looking very promising.
I mean what we have done is put a lot of… We care a lot about the details of the products, I mean about the interactions, to be honest of one part of the product which is the part you're interacting with lists. Lots of the product the setting, dialogue and stuff is pretty terrible but that is the thing that we spent all the time on essentially. What is the core value that we are creating like that's where we put all of our energy.
The things that WorkFlowy does, it does really, really well. I think other people besides me have recognized that WorkFlowy is on to something and that you guys have a lot of competition. I think it's one of the more interesting stories because I've never seen a product get cloned so many times and so directly as WorkFlowy. A lot of the clones are crappy like usually when someone clones a product it's pretty crappy.
There's a couple of really good ones. Basically my thought on that… Do you want to finish… Oh, you finish your question.
The thought on the clones is basically like we didn't do much for a long time and that is why clones exists because there's a lot of stuff that the product needs and I think some of the clones are nice but none of them get the details I think as right as we do. Most of them are focused on adding more features. The biggest thing that I see with clones is that they don't have… I would say they're not me. They don't have the vision that I have. I see them, I'm like, "Oh, here's a nice one that did a nice job. That's interesting."
Then I look into it, I'm like, "Oh, okay. Once we start having product momentum, we're going in a different direction. They're adding the obvious adjacent things that are needed which we will do but they're not building into the future where WorkFlowy is a tool that actually makes you smarter and this is a tool that helps you think through things in ways that you don't know how to think through and all these things that just come out of who I am kind of I think. A lot of them are none obvious but I think there's a lot of obvious stuff that could be added to WorkFlowy which is good and I'm glad that people are doing it but they're also… When I look at them there's two things. One, I'm like, "That's not as polished as it needs to be and it doesn't work quite as well as it needs to." Just the direction of the product is not as inspiring. I don't see this product working out and being used by hundreds of millions of people.
They lack the vision that underlies all the decisions that you're making.
Yeah, that's how I feel about them. Honestly, it's both really frustrating and really like imitation flattery, et cetera. It sounds flattering. It's frustrating and it is gratifying to me that we've been able to move into a mode of growth and investing in the product and investing in the company because otherwise their product would just eventually languish and the clones, the wars… What is the sequel, the Star Wars like number two. Attack of the Clones.
Attack of the Clones.
The clones will win.
You can't let the clones win and I think it's cool to hear your take on it. I wonder like the clones inspire you in a way. Do they light a fire under your ass or do you just ignore them to the most part?
I think they inspire… The new team members who joined, it inspires them. I think they upset me but to be honest they don't motivate me because I have extremely strong motivation without clones. If we had zero clones I would have the same level of motivation I have now of just… I am just dying to make this thing that's in my head real in the world and just dying to realize what feels like this very tangible opportunity in front of me.
I think you're in a good position to do it and it's an interesting situation because when you do something that's new, and you're the first mover, you have the advantage that you get all the initial mind share. WorkFlowy is way bigger than all of these clones and probably will be for a very long time if not forever, but at the same time when you're the first mover, other people are going to clone you. It just happens. No one has invented anything that other people haven't tried to clone.
The last thing, before I let you get out of here is I'm curious what your long-term goals are? I don’t just mean with WorkFlowy, in terms of making it the product that it can be but I mean personally. If WorkFlowy tomorrow was the tool that you wanted it to be and it was bringing in people from all over and you're doing a great job educating them to having use the product and showing them examples and it was just fulfilling all the goals that you asked for.
We have a billion people using it and it's on every desk and it's running every company, et cetera. My long-term goal is to be a mad scientist. Very simple. I want to solve all the world's problems. This is just like completely impossible and completely crazy. I just want to be making stuff that makes the world better and also just making stuff that I enjoy making. The dream if everything was crazy successful would basically be to build more stuff and to focus on some pretty crazy ideas as well around making people happier, structuring society in a better way.
It would be awesome by the time I died. I felt like I was part… Not necessarily started a movement but it was just part of a movement or part of something that felt like, " This is addressing the flaws or how our society works right now and is going to hopefully 100 years from now like people and animals and everything will be happier because of this thing we're all doing. I feel like that's what… Honestly, that's what most people want. Most people would love to feel part of something as well. For me it's like, I would like to be in this position to be like a real mad scientist doing large scale crazy things, testing those kinds of ideas.
I really hope you get there, and I would love to test out some of your mad scientist creations when you do. Thanks a ton for coming on the podcast. Can you let people know where they can go to find out more about what you're up to at WorkFlowy and about you personally?
There's not a lot of information about me personally on the internet. I'm afraid of the internet to some degree to be honest.
It's probably smart.
WorkFlowy is workflowy.com, and blog.workflowy.com is our blog, and Google WorkFlowy. That's what everyone does. Our search terms are only WorkFlowy.\
Low hanging fruit man. Thanks a ton. It was great talking to you, Jesse.
All right. See you.
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