How to validate your idea by finding your own pain

This is the story of how finding your own pain can lead to a profitable company.

Chris Keller is the founder of, a site he built to solve a problem he had.

You know how sometimes you send someone an email and you want to be reminded to follow up? Well is an easy way to embed a reminder in your email.

Chris Keller

Chris Keller

Chris Keller is the founder of which attaches follow-up reminders to emails.



Full Interview Transcript

Hey there freedom fighters. My name is Andrew Warner. I am the founder of, home of the ambitious upstart. I want to make sure that everyone remembers. It’s not just a brand, it’s a great brand but it’s not just a brand. It is a web destination,

And today I’ve got this story of a founder who built a profitable company which he sold, and he did it all because he discovered his own pain and then he validated it and then he created a product which he charged money for. I invited him here to talk about how he did it. His name is Chris Keller. He is the founder of And let me explain this way.

You know sometimes when you send someone an email, you want to get a reminder to follow-up with them. Well is an incredibly easy way to embed a reminder in your email. All you have to do is cc an address that they give you. All right. We’ll find out more about it and how he built it, and we’ll do it all thanks to Scott Edward Walker of Walker Corporate Law. He is the entrepreneur’s lawyer. If you need a lawyer I’ll tell you why you need to go to, but I’ll do that later.

First, I’ve got to welcome Chris. Chris, good to have you here.

Chris: Thank you. Great to be here.

Andrew: You sold the company. You went on vacation. Where did you go?

Chris: Oh, man. First I went west. I went to Tahoe for some skiing, then to Kauai for a couple of weeks, came back through Denver, little more skiing. And then I went to Europe, and that was pretty quick. Within two days I was in Europe, so the jet lag was a little much. But I was in Belfast for a wedding, London, Amsterdam, Iceland, and then D.C. And then back to Boston.

Andrew: How did it feel to take that whole trip without any worries about a site breaking down, not finding customers, all that stuff?

Chris: Admittedly it was really nice. My girlfriend was actually with me on the trip so we just got to go for a few months and just basically relax. It was great. It was just nice to kind of like look at these other parts of the world again and just look at the difference in culture and like the food and the way they do things. Even door knobs are so different. I actually got confused by one in a bathroom in Amsterdam. I was like . . . It’s exploration, right? You just don’t get to do that in your everyday life anymore.

Andrew: I had to take a whole lot of free time off after my last company, the first one, and I remember little things would excite me, like I got on jet skis in the Virgin Islands, and it was so much fun that I just got to say to the guy, “I want to do it again, but now I want to do a private session where I just do whatever I want.” I thought I could do that. I get to do that. I don’t have to worry about money. I don’t have to worry about — is it inappropriate to do it right now? I get to do whatever I want. So it’s those little things that made me really happy and I get it.

You didn’t have an easy time getting here. You bootstrapped to get here. And before that you built another company, one that was celebrity based. What was that company called?

Chris: So that was Fafarazzi [sp]. I co-founded it with a guy that I worked with at Johnson & Johnson prior. So this was kind of my first foray into the startup world full-time. And he and I both quit our jobs to do it full- time and we said, “We’re just going to live below the poverty line and make this work.” But then we said, “We’re going to go and try to raise money for this because basically our feeling was this can be big. We’re going to give it a shot. This is the time to do it.” This was like summer of 2007.

Now it was a different experience because we did end up raising VC money, and I think ultimately we needed that to get things going. But we were talking before. It’s an interesting story of how it was very different from what I did with Followup.

Andrew: One of the things that I noticed is different is were you having trouble keeping up with celebrities and needed a way to gamify your excitement for them?

Chris: So coincidentally no. It actually came together because all his friends were playing Fantasy Football and obviously I had some that were too. And then we noticed that all the girls around us loved celebrity gossip. And so I was talking about how I wonder why there isn’t a fantasy game for the real world where it’s like people are doing things in the real world, all you have to do is give them some points. And then all of a sudden the light bulb went off in front of both of us, and we were like what about a fantasy game for celebrities, because they’re always in the news about the stuff they did. That’s where it all came from.

Andrew: That makes sense as an idea. Today, if you had to do it over again, based on what you know about validating through customer conversations and tests. It seems to me that you wouldn’t go and build it, you would go and talk to women that were into celebrities, who you thought of as your ideal customer and say, if I build this what would you say? Or, actually, how would you go about it, to validate this idea before building it?

Chris: I think that’s right, our demographic during running the business, it was 80% woman, especially in our initial product. I can go into what our second product was, but I would totally validate it that way, but not with just asking them. Literally, every single person that we asked, they thought it was brilliant. They thought it was the coolest idea ever and every little girl was like I want to play this. I think the validation in this case is not about is a woman going to like it, it’s really going to be around getting the game play semantics, right, validating that it’s easy to use, that they understand it.

Then, as it turned out some people never got enough into it, some people became to obsessed with it, so you had this balance of how much does the customer want to use this thing a day. I think that’s true of a lot of gaming. Where people are like, yes everyone plays my game all day long. The problem is, at some point people say, I have to live my life or I have to fix this problem of playing this game. I think that . . .

Andrew: The validation wouldn’t be enough to go and ask customers would you use this.

Chris: No.

Andrew: In your case you got positive feedback that way.

Chris: Yeah.

Andrew: You want to make sure the mechanics of the product you are creating are aligned with what people will actually do. How do you test that before you build a full product that works and that you invested money in to develop it?

Chris: That’s an interesting one in the [??] case. Because, we did actually say we needed to build a lighter weight version of what we had. Because, it was basically a real fantasy football league, but done with celebrities, and it was only four weeks long. If you think about it, one of the beauties of internet models is that you can iterate very quickly. But, if you have this month long league, that doesn’t help anyone. I think you still have to build some usable product, an MVP, or whatever you call it.

We would of done it to where it’s hey, play this game for a day, or let’s at least attempt, if you are coming back here to read the news, and that you are making a trade, or picking a team of celebrities. If you were doing these actions, then you probably were into it. Because the social component only made things more interesting.

Andrew: I see. If you’d create the right first version to test whether people were really interesting in it. It would allow them to pick the right celebrities and see if they would even create their fantasy celebrity team, sort of speak.

Chris: Yeah.

Andrew: Okay.

Chris: Yeah. Almost like give yourself a version of the game before building a more complex product with trades and this and that, and all the scoring, as it is with that team.

Andrew: You raise money for that business, unlike, which was bootstrapped. Did you like having a company with $800,000 in funding, and cash in the bank, and all the glory that seems to go along with having funding?

Chris: I think that was both Todd and It’s the first VC backed company, so of course we were like holy moly we just got all this money. We look at it in our bank account, and we’re just like, oh my God, this is crazy. But, we very quickly were like, wow, now we have to get back to work. That was all there was to it. The thing was thought that we were very practical guys.

We weren’t like, oh, we got all this money, we’re going to buy all this crazy stuff, and yet when you raise VC money there is some level of that you need. Not in terms of doing silly things, but in the sense of we need to spend dollars to grow this business. Especially, at the time where in 2007, we’re talking about advertising eye balls, you need visitors. That is the only revenue model that was really plausible, especially for total consumer facing start up. We didn’t do it, we paid ourselves barely anything, even with the VC money.

And we didn’t spend enough money on advertising. We didn’t spend enough money on hiring because we were saying we’re going to make this the only money we raise until we’re profitable. But so in some sense, we were trying to be smarter about it and yet I don’t know that that was necessarily our best strategy in the end because we were playing the VC game; it’s all about growth.

Andrew: How did it end up?

Chris: What’s that?

Andrew: It seems like then that would work out okay because you’re not burning your cash, you have it in the bank, you’re looking for profitability, you’re looking to build a real company. Were you able to do that?

Chris: So we started out charging for product where we said you pay X dollar per user per league early on and people were paying. I remember within like a few months we were making $1,000 a month and it was like great people are paying for this. I think after that then we said okay we raised this money, we’re going to drop everything to go free which was our version of focusing on growth. But ultimately it didn’t pan out.

So I actually left the company after two years running it full time with my co-founder. We got what I call an amicable divorce. And then he kept running the business actually for the next four years after that. So the company actually did end up developing a revenue model on our second product and running for six years in total. So it did pretty well on that 850 because it was supplemented with our own revenue but ultimately it just never achieved the growth that it was going to amount to anything for like a big sale or anything.

Andrew: How did it feel to walk away at the end of that?

Chris: Oh man! It was hard. I was burned. Not burned but I felt like what the hell do I do now? Because I think…and I don’t know if this is going to be true for the young entrepreneurs today that are in their early 20’s but for me it was very much like, you know, I was starting companies in college like web design, consulting type stuff. I built the Facebook of the tennis industry. That was the tennis site, how I met Noah Kagan.

You know, so I was doing all this stuff on the side and Fafarazzi was like the culmination of what I at that point dreamed about. It was like I am running my own company and VC-backed at 25 years old. And so all of a sudden when that was done and it wasn’t successful for me I just kind of thought well what do I do now. It was really like a scary…

Andrew: Did you feel like a failure?

Chris: Oh, definitely. For some of the time. I just … I mean I didn’t think like, “Oh I’m a failure because I’m not…” .Yea, I don’t know if that’s quite the right word because it wasn’t like I felt bad about myself. It was more like why did things end up happening this way. Like, I never saw myself as someone having the co-founder issues, right? Because I generally get along with people, easy to work with and so it’s like how…

Somehow I ended up being one of those guys and that’s how it is. I mean it was a great experience to go through from a learning experience but…And like to this day he and I are still friends because I think we handled it correctly. And our VC…

Andrew: What did it take? What does it mean to handle it correctly?

Chris: So we knew that…so we did…The way I always explain it is like things started to change in our working dynamic and so it would be like two steps up in frustration and then we’d talk about it and it would be like one step down. So we’d, you know, be better for a while.

Andrew: What would get you guys frustrated? But I see that you’re still net frustrated, more frustrated than you were before.

Chris: It was like the…It’s like the way you want your revenue, right?

Andrew: Right. What would get you guys frustrated?

Chris: There were just dynamics in terms of role responsibilities. So, I was very…I was the CTO and he was the CEO but like I think in terms of my…I think it’s kind of odd that I was like building the bigger tech stuff and he was more on the front end and a good designer and UX guy and yet I’m also kind of more of the networker, social type a little more than him. I mean he was a good talker too with people. But, you know, my natural behavior was I loved networking. I loved meeting people in the industry. I loved trying to make deals happen but at the same time I still need to sit there and build a product.

And so at times it was like do we need to hire a real CTO to help us keep building this while I go focus on biz dev and growth. And so there was a little bit of this tug and in addition it was just…It was also…We each had the little things we had to do and if those didn’t get done, there was this sense of frustration like wait, why aren’t you focusing on that and why are you focusing on this. It was aligning priorities. When we disagreed on priorities it was like well, ultimately he makes the final decision…

Andrew: Why did he get to be boss? You are the…you’re a developer, but so is he.

Chris: We would have been equal partners because we did come up with it together, but he actually… When I left Johnson & Johnson, I actually left to join a startup in Boston. He happened to be up here already running another idea of his. He ended up working basically part-time and then just about full-time on Fafarazzi for about four months or six months longer than me.

When I finally was able to join him, it was like well, now we have this kind of are we equal equity partners? Or do we like factor in…

Andrew: Were you?

Chris: No…

Andrew: That created some tension because you should have been equal. Just because you couldn’t get out of previous obligations at the same time he did doesn’t mean that you should’ve suffered. And…

Chris: But here’s [??]…

Andrew:…you’re both developers. If anything you’re much more outgoing than Todd is.

Chris: You don’t know him, but I still agree…

Andrew: That’s another reason why I could say that. I would know Todd if he was more outgoing.

Chris: He would meet you if he was an [??].

Here’s the thing: the question was how do you reward…and this is a good general question. This situation actually comes out a lot with startup founders. How do you reward someone for their work that could have been before you both go full-time. I know this question comes up a lot. Is it more options? Is it more equity? Is it a cash bonus at some point? How do you…do you actually reward that or do you just say, no you know what? Forget it. That…

Andrew: You say, no you know what? Forget it. It’s only four months.

Chris: Wow. Okay.

Andrew: We’re not talking about a year.

Chris: What’s that?

Andrew: We’re not talking about a year even. We’re not…we’re talking about…

Chris: Here’s my answer to it.

Andrew: Okay.

Chris: We did not do your typical vesting schedule. We did this kind of weird reverse vesting schedule that basically was saying that I was earning my equity back over time until… basically taking away from his extra. Because we agreed that over time that four months would make no difference if things were going well.

Andrew: I see. Okay. That makes sense.

Chris: But the problem was that we still didn’t do normal vesting schedules where essentially we had the same amount of equity on paper. It was just that I would reach that level later than he would. It wasn’t set up like that. That’s how it’s…

Andrew: I see. So as a result it felt like you were taking equity away from him as opposed to earning equity from the company.

Chris: Correct.

Andrew: Okay.

Chris: Todd, don’t get me wrong, is a good guy. I don’t think he ever…of course you can argue because I ended up leaving the company, but he never in any way acted like he didn’t need me or want me. Until maybe the end of our frustrations. The product was built. Everything was kind of going smoothly. He had a good handle on things. So that was it. I was kind of out.

Either way. We handled it the way we handled it at the time. I still think we both tried to act fairly in our own mind-sets. He’s a good guy and…

Andrew: And went to work for a past Mixergy interviewee, Dharmesh Shah at HubSpot.

Chris: That’s right.

Andrew: How did it feel to take a job after being an entrepreneur?

Chris: It was an odd feeling because I did not think I would be going to work for someone else especially three months after I had left my own company. I will say that having someone like Dharmesh, who’s amazing, come to me and say, Chris I want you to come run the labs division of HubSpot with me and basically be the entrepreneur within HubSpot. That was unbelievable. I was like, I’m so excited. Let’s do this.

Andrew: How did Dharmesh even meet you to say that?

Chris: I don’t know. I mean he and I had crossed paths in the kind of Boston Tech startup scene since 2007. Then we had a…Dharmesh is known for his dinners. He loves taking entrepreneurs out to dinner. That’s where he starts to network, meet people and get a sense for who they are and what they want to do.

I’d been on a couple of those dinners with him. I’ve emailed him things that came up just in normal startup life. Whatever. He saw what I’d been doing with Fafarazzi. He’s seen my previous stuff. He said… he knew that I was a kind of an idea, innovative guy who could build stuff. So he said come, take your ideas and build them at HubSpot.

Andrew: Is it one-on-one dinner?

Chris: No. He’ll do both one-on-one and a group thing.

Andrew: Okay. All right. So then, you have this problem. You’re doing Bizdata Filing. You’re actually getting to talk to potential partners, and what’s the problem that you had?

Chris: So, ironically, this is in 2007, while I was running Fafarazzi, literally when I started running Fafarazzi with Todd. I’m reaching out to people that I met at conferences, and these were warm emails. These were not even cold leads, etc. I email, I’m thinking I’m going to get a response in a couple days, and then I either got a response two weeks later, which was way longer than I wanted or expected, or I never got a response at all. And I was like, “Man, I really need a way. I would have followed up with these guys if I anticipated this slow response.

So I was like, man I really need to start keeping track of this. So every time now I email a colder email, I go to my calendar and put, like, “Email Bob, if he hasn’t replied,” and I’d set it two weeks in advance. Then the Google Calendar reminder comes in, and I’m like, “Who the hell is Bob? And where is that email?” So, I was like, “There has got to be a better way for this.” So one day, I was like, “You know, I really wish I could put the reminder on the email when I send it, and it bring back the email to me.

And so then, I started thinking about, how can I do this? And I thought, well, if you could somehow use the BCC field, only I can see it, they can’t, and you can indicate when in the form of an email address. And so that was literally when it was born, and I built the first version in a week after I thought of it.

Andrew: I see, and it was just for you at the time?

Chris: Yeah. I built it as a service that anyone could use, but I was the only one using it, and then I showed it to Todd, and he was all about it, and then I started showing it to a couple other friends, and they were really interested in it.

Andrew: You know, I found an early version of the site. I can’t even figure out the date.

Chris: No archive?

Andrew: Yeah, but I took a screenshot, and now I can’t figure out the date when I got it, but it’s the very first available date, the first screenshot that archive has. You ask people for an email address. You ask them for a password. You ask them to confirm the password. You ask them for a time zone. You ask them for a gender. You ask for a zip code, and a birth year. Why?

Chris: Because this is 2007, and no one had talked about optimizing things. No one had talked about making it as easy as possible, not asking… You know, this is like back in the day when the only thing that mattered was demographic data and eyeballs. That was all anyone cared about for a business.

Andrew: I see. And so you were still thinking, “Maybe demographics would allow me to sell advertising to these eyeballs?”

Chris: I actually had said from day one, “I think people will pay for this,” but I also said, “If enough email reminders are being sent over time, then obviously you could start putting ads in those that are relevant and not crappy, hopefully.

Andrew: All right, that was from January 3rd, 2008.

Chris: Yeah.

Andrew: The first version that they have in there.

Chris: The way-back machine, or the internet archive, used to have a screenshot from literally July 2007 when I launched it, but apparently that’s gone. So now there’s only the January 2008 one.

Andrew: That’s disappointing.

Chris: I know, because the thing is, I wanted it to be seen, that this is literally a day-one kind of screenshot.

Andrew: What do you remember about that first version?

Chris: That’s a good question…

Andrew: Did it look as good as you’d like it to look? Did it have the features you wanted? Did it explain things well? Did it ask for people’s height?

Chris: [laughs] No. So you know why? I remember now that it sent the reminder email out, but it wasn’t threaded in the first version, and I remember that was the first thing that I and other people said, I was like, “God, I got to get this threading working. Otherwise it’s useless.” And then the other thing is, I didn’t have the concept of snooze links in the first version, and those are really been becoming the most popular thing.

Andrew: So the way it would work is, I email Noah and say, “Hey, Noah, do you want to come over on Thursday?” and I CC a number. It would be Actually, that would be in the BCC field.

Chris: Yeah. BCC. Right.

Andrew: A day later, that email comes back to me, and because it’s threaded, I can see, “Oh, yeah, Noah, I emailed Noah yesterday,” and I could even look at the follow up .cc email and see what I’ve written to him before, and then if he doesn’t email me back, I could say, “Hey, Noah, can you tell me if you’re going to come over on Thursday?” And the snoozing is, the links that you added later on to that email that bounced back to me that said, “Snooze this for an hour. Get back with me tomorrow,” etc. So then I don’t have to email myself, or email follow up cc’s again.

Chris: Right.

Andrew: I brought up Kagan. So you had this problem you created for yourself. How soon did you show it to Noah and other people?

Chris: Noah, I probably showed within a month. And then other people, I mean probably around the same time. So, here’s a good way to explain it. So, I showed people the follow-up like almost right away once I had a nice working version they could sign up for. And the problem then was I am running a VC backed company. I cannot be spending my time especially when also that one did not involve my co-founder. And obviously we have shareholders now. So it’s like I cannot spend time on this really aside from maybe a couple hours on the weekend like iterating slowly. So basically it was one of those labors of love where I would just keep working. I would like use it on my job and then I would like tweak a little here, build a feature there, and improve it a little there. But it was super slow rate of development, right because I was still spending all my time on Faterizi [SP]. And even any extra time because it was just really, you know, that was like my obvious obligation. And what I should be working on actually.

Andrew: So can you get feedback when you have a full-time job where you’re running a funded company? Can you get feedback? Can you show it to people?

Chris: I don’t know if this kind of gets back to the eternal debate of should entrepreneurs have side projects or you know, work on anything that’s outside of their core focus? I mean obviously you can just show it to people and get feedback. And it’s really just like a nice, like a “hey you’ve got a really good idea.” And then the whole question is like, are you going to do something with it? And then it’s this like kind of thing inside that just eats you up because you’re kind of like, I want to work on that. But I really got to focus. And so I did.

For the most part, I did not, I kept tweaking follow-up for my own needs. So in terms of customer development, I think a lot of people – so email is a such a general product right? And everyone has different habits, processes and whatever right? But the fact was is when I used my own product, I knew where the deficiencies were just in terms of my own use of Gmail. I’d get these reminders, I’d be like crap, I wish that was better. And I’d fix it. Again, I’d be like, Oh I wish it would do this. And I’d add it in. And they’re all just little tweaks in my spare time.

So, I think a lot of people, I think there are a lot of instances where people are not great product people and they’re feel like they can figure it out for myself right? And I feel with my email product being the number one user, I was able to do a lot of good development that actually made sense for the product. Now, with that said, when follow up got out to more of the general public, I certainly got more feedback than from just my own usage?

Andrew: Such as?

Chris: Oh my God, there’s so many. You got me on the spot with that one. Let me think about this.

Andrew: And we’ll come back to that.

Chris: Oh here’s one. So I had a guy say to me like, Oh, hey one of my hacks, when I get an email from someone, I will write the reply immediately. And then forward it to follow-up instead of hit, actually send the email back to them. And I was like why are you doing that, to slow down the conversation? And he said exactly. So basically his own response comes back to him a day later. He cuts and pastes it into the reply and then that way he manages the speed of the conversation.

Andrew: I see.

Chris: I never would have thought of that.

Andrew: And the way you were getting feedback I have to talk about in this interview. I also want to talk about something that’s not directly relevant but it’s kind of fun, the way you met Noah and talk about how you got users to pay attention to this when you didn’t have a budget for advertising and so on and also how you generated sales. But first I have to say a moment ago you talked about the potential problems with co-founders. Who owns how much? How do you allocate equity in the company? Do you do it all up front? Do you do it over time? How do you do it?

Chris: Well to answer that question, you I have to recommend you talk to a lawyer who had gone through this multiple times, someone who has seen the potential problems that you are likely to face who can at least advise you. If not show you exactly what to do to avoid. I know we entrepreneurs tend to be a little bit stubborn.

If someone tells us that you have to do something, we’ll fight it. But we at least get to know what our options are. We at least need to know what our potential challenges and problems are going to be down the road. We need to know them from someone that has a credibility to tell us about them because he’s seen it multiple times.

And if that’s the lawyer you’re looking for, someone who’s gone through this, I recommend you talk with and actually work with Scott Edward Walker of Walker Corporate Law. If you want to find out more about him, you can go to You’ll see a list of people who all said really nice things about him, and you can follow up with them and ask them, “Hey, what do you really think of Scott?”

I just had a conversation with Nick O’Neal who’s quoted up on recently. He had a really positive experience with Scott. He and many other people here in San Francisco and throughout the country have said things about recommend and work with Scott Edward Walker of Walker Corporate Law. If you need a lawyer and you’re an entrepreneur talk to him. You’re thumbsing [sp] it up, why?

Chris: Because I agree and I trust you that he’s great.

Andrew: [laughs] All right. Right on! Check him out for yourselves, The right lawyer can really help with your company, help you avoid problems and allow you to focus on your business. You talked to people, and you wouldn’t say what people would say which is, “Here is my site. What do you think of it?” What did you say when you were getting feedback on

Chris: So I would basically send a note or an IM of whatever to my friends, “Hey, this is an awesome site that I found.” And then I would see that their reaction is. I would not tell them that it was mine because I wanted just a totally unbiased opinion. I was to see if they’d be like, “Oh this is neat, but I’d never use it” or “That’s cool,” but really a bunch of them were like, “Yeah, this is awesome. I could totally use this.” And then that’s how it started.

Andrew: You also were looking, as I understand it, to see . . . Do they even understand what the site does? Do they get how to use it, right?

Chris: Yeah, that’s true. I would literally say to them . . . I would ask them questions like, “Oh yeah, it looks like you set a reminder this way and see if they’re looking at the site” if they kind of correct what I say. If they’re like, “No, no, man, it’s like this.”

Andrew: And Noah was one of those people.

Chris: Yes.

Andrew: You’ve got to tell people how you and Noah met.

Chris: So I built a tennis social network back in 2005 when it was hot to build a niche social network.

Andrew: So it’s

Chris:, that’s right. And so it was doing well in the tennis community, and so all of a sudden I started getting a couple of messages from users being like, “Hey, this guy is spamming me with a message advertising his own tennis site.” And so I look in the database, and I see that there’s like about 50 messages. And the thing is I had written the code in a way that it could not be scripted. You had to click the button via a manual click.

So I emailed this guy and I’m like, “Hey, Noah” and I Googled him. I saw that he was like a Silicon Valley kind of hustler guy. So I emailed him and I was like, “Hey, Noah, would you stop spamming my site because I’m not on your site wasting my time spamming yours. I’m sure you can find other ways to get potential customers.

And so he writes back and he’s like, “Oh, no, what are you talking about?” He’s like, “I’m not spamming.” I was like, “Yes, you are. I just looked in the database.” And he goes, “Wait, how did you look in the database?” And I was like, “I built this site. And he’s like, “Really?” He’s like, “Good job, dude.” And then he asked me like, “Did I want to work with them” or something. It was really funny.

But basically we went back and forth. I think we talked on the phone briefly, and they we said, “Okay, next time you’re in New York City, let’s get a burrito” because I was living in New Jersey at the time. And so sure enough I finally met Noah in person six months later in New York City, and I met him at a burrito shop. And then he shows up and he’s like, “Hey, man, I really actually had a burrito with someone else, but let’s just go for an hour walk.” It was classic Noah.

Andrew: And so he was actually getting users by one at a time emailing people.

Chris: No, logged into meshtennis just like going through the list of . . .

Andrew: Emailing, messaging using your system.

Chris: Yeah, exactly.

Andrew: All right. Then he became such a fan of that he started to tell other people about it. I’m one of the people who told about, and he said, “This is the way you keep on top of things.”

Chris: Yeah.

Andrew: You didn’t say, “You know what? I can never trust this guy again. He is spamming my spamming my audience. He’s a spammer. I’m done.

Chris: No, no. Once we got to talking, I realized he’s just a hustler trying to do his job, and I realized he’s a good guy and just energetic and supportive of what people want to do. So it came out very quickly that he was just actually really with it and wanted to make stuff happen.

Andrew: I’m continuing through the archives of your site, and I see March, 2010, no more asking people for their age, no more asking people all those other questions. But the one question I don’t see here that I don’t see and wondering about is payment. Did you start adding payment? At what point did you start adding payment?

Chris: So I did my year at HubSpot from September, 2009, to October, 2010, and I decided it was time to do Followup full time. Again, it was really like I wanted to go this a shot. So I think you alluded to this question which we can come back to, so Followup started to get a lot of press over that year while I was at HubSpot even me asking for it.

It was like some little blog found it and covered it and then Life Hacker saw it and they ended up covering it. Then the classic media foray around and that was it literally. Life Hacker was definitely one of the best drivers of new users out of all of them.

Andrew: You have no idea how that all happened?

Chris: No, I mean, it was . . . It got mentioned somewhere, and some blogger found it. It was just a classic thing that no viral was a thing back then really. But I guess the concept was starting to be there. It was just simple. It wasn’t even like a crazy amount of people. It was just one blogger covers it. Life Hacker happened to follow that blog, and so they covered it. And then once Life Hacker covered it, it was legitimacy, right?

Andrew: I don’t know about this, Chris. I’d probably do what you said earlier which is put in the bcc line of my email. So I email you about something. I want to know to check back with you tomorrow. I will in the bcc field write And then the next day I’ll get a reminder. But if I put it in the To line me and my recipient get a reminder the next day, right?

Chris: That is right.

Andrew: So my recipient is introduced to because of me.

Chris: Yes.

Andrew: That’s the virality of the product.

Chris: That is part of it but . . . This is actually part of a segue into payments and all of that. So you have to think tough about the primary value to the person because having these bcc reminders . . . The most important use case for Followup was I need a reminder. It’s not for someone else to see. It’s just I need it, right?

So the question was is there enough value in this tool that you’re willing to pay for it. And I decided that there was, and everyone told me there was. And so I’m going to go ahead on the bottle [sp] where I’m charging people for reminders.

Now the cc field is definitely the only way really that Followup could be viral. However, the cc field was certainly use cases. It was less than the private version. Whenever I go and have lunch with someone and once we agree on where we’re going to meet, I would cc . . . In my last message I’d be like, see you at whatever, Chipotle, and then I’d put my phone number and that was it. And then I’d say like cc Wednesday-12 p.m.

Andrew: So now they’d get a follow-up reminder just like you would.

Chris: Just like I would at the appropriate time with my phone number so that they would need to text me, I’m running late. They could just click the number and text me. So I was trying to make it convenient for them. So that was one example. The other case was someone says to me I’m interested. I want to talk or I’m traveling. Hit me up in a month again. So I say great. I’ll let Followup take care of it for us, and I see one month to follow-up. And then they’re like, oh, wow, that’s really useful. He’s serious about following things.

Andrew: They’ll know in a moment you’re serious about it, and then they get the reminder. So you’re saying isn’t that a way that people would find out about the product virally?

Chris: Oh yes, and people did. And I dropped that. There definitely was viral spread, not like crazy I don’t know what you’re talking about coefficients or whatever. It wasn’t like viral growth but that’s again because I say people’s natural inclination for the product was to be cc. Their reminders were really private. They weren’t always these public . . .

Andrew: I see.

Chris: Again, that’s why I say it depends on the social context of what you are saying with the person.

Andrew: But then what did help it take off? What got traction?

Chris: One, is time. If you think about it, this thing started in 2007, and it was a side project for two years, but then when I was on it more full- time, I mean, obviously at Help Spot, I wasn’t on it full-time, either, but it was a good idea solving a problem. That’s number one.

So I know that people always say, “Oh, ideas don’t matter.” I agree there’s a lot of businesses where the initial idea is wrong and you figure that out in testing, but I think people forget that a really good idea will get coverage. People want to talk about neat and good and useful ideas. That’s what happened with follow-up. Ultimately it was just the trickle effect, right? I got one person to write about it, then other people started to cover it, and it just kept building.

Andrew: Tim Ferriss was one of those people, and he’s still sending you traffic from 4-Hour Work Week. How did Tim Ferriss discover it?

Chris: I think you were referring to actually a guest post by Noah.

Andrew: Oh, Noah posted there, and that’s why you’re getting it. It’s not even Tim Ferriss. It’s Noah saying, “This is what I use.”

Chris: No, in fact, I met Tim at South by Southwest in 2010, he might remember me if I say exactly what I said to him, but I didn’t even pitch him on Follow Up. I didn’t want to be another guy trying to pitch him on something. I actually was talking to him about nutrition, because he and I shared an interest in the same authors in general, like at the time Paleo kind of interest.

Andrew: Okay. He wasn’t. Noah was one of those people who sent you traffic.

Chris: Yes. Noah has sent me a lot of traffic, and I also would point out that a lot of people might hear this, and think, “Oh, I wonder if Noah was getting a cut or anything.” Noah literally would never let me do anything for him to thank him for promoting follow up, and on top of that, he was a paying user, and almost asked me to charge him more. He’s that good about it. He literally was like, “I don’t want a damn thing from you. Just keep making the service better.”

Andrew: I know. That kind of stinks. I even bought him scotch the other day. He laughed at it. But App Sumo is one of the sources of traffic. You guys did an App Sumo deal. That’s it? Copy Blogger. What did you guys do with Copy Blogger?

Chris: I have no idea.

Andrew: Oh, wow. All right, and this is partially because you’re not there anymore.

Chris: No, because I assume they just covered us. What did…

Andrew: I have no idea. I’m going to see what Copy Blogger did. So then, is there anything that you can about traffic? Go ahead and do that. I’m going to do a quick search here. I can do site, colon, and then Let’s see if I come up with anything.

When’s the best time to send email to your list? Five boring business that can succeed on Pinterest. Boy, I can’t even figure it out. I can’t tell why you’re suddenly getting traffic from them. Where did you go just now? Did you go to the bathroom?

Chris: No, I just went to turn on the light.

Andrew: Oh, because it was getting dark where you are.

Chris: It is a very gray day in Boston, unfortunately, unlike, probably, where you are.

Andrew: No, I can’t tell. It’s always a nice day here because I have the clicker. Do that, I like. Do that, wait, there we go.

Chris: That was good.

Andrew: Yeah, it’s one of the highlights of the Mixergy HQ tour. The other one apparently is my chest hair. So, I was telling you before, I hated the way I dressed. I didn’t realize, because I don’t look at my videos. I didn’t realize my button was all open and my chest hair was exposed. But I hated the way I dressed. I complained about it a lot on Mixergy interviews. Then Sachin Gupta said, “I hear your problem, I met this guy who knows this guy who knows this stylist.” Anyway, he hooked me up with this stylist, now I’m wearing pink, and I think I’m wearing it well, and a pocket square.

Chris: Nice. Your outfit is very Thomas pink.

Andrew: Thomas who?

Chris: Brand. He has this combo. It’s very his style.

Andrew: See, this is stuff I need to know. Who is this Thomas guy?

Chris: I don’t know who he is. It’s just a store.

Andrew: Thomas Payne, you said?

Chris: Pink, pink.

Andrew: Thomas Pink, all right. I might have heard of that. I don’t know.

Chris: Yeah. You see, his stuff is at high end malls and airports and all that kind of stuff.

Andrew: I like how you know this stuff. I like your shirt. Who made your shirt?

Chris: This is Banana Republic.

Andrew: Oh, okay.

Chris: Yeah. By the way, I see you still have the beads on.

Andrew: That’s right. What do you have to say about that?

Chris: Did you follow your mantra?

Andrew: I did, yes. My mantra is, “To be a pro.” On days that I do interviews, there’s always some wacky thing that happens, like earlier today, the person who I called hung up on me. I called her for the interview. She wasn’t there. And then I called up the number and she hung up and then I called back and she didn’t pick up. The person that I think I sometimes am would want to just go, “What the… I’m here. I hired a pre-interviewer. We researched you. I’m ready!” [inaudible] Sorry?

Chris: I said you do. You know a lot of stuff coming into this interview.

Andrew: Yah. I’m prepped. Some of it I don’t know all the way, like I don’t know why CoffeeBlogger would have an interest in you yet, but I do my work and the team does their work and I sat here for the interview instead of something else and… you know what, I decided I was going to be a pro, and a pro wouldn’t go out of control about it. A pro wouldn’t go on Twitter and go, “What the hell did you do?”

And so later on I got a note saying, “Listen we’re a little embarrassed. We’re not sure we’re ready.” Anyway. So that’s one of the mantras that I use. The other one is trust. Especially when people come over for drinks. I worry that we’re not going to do the event right. That I’m not going to have a great time, they’re not going to have a great time. All that stuff. I walk in with my beads. I say, “Trust, trust, trust.”

And if I’m just trusting, no matter how nervous you are, you’re going to pick up on my trust and you’re going to be okay. If I’m just trusting, no matter how worried you are about revealing too much to me over scotch, you’re going to feel comfortable.

Chris: The only other things I’d say though, is you’re a genuinely good person, right? And you care about your guest’s enjoyment.

Andrew: Yes.

Chris: You shouldn’t worry too much.

Andrew: About my guest’s enjoyment?

Chris: Things are going to work out.

Andrew: What do you mean?

Chris: Things are going to work out. You already are someone who mentally cares and you are a genuinely nice person, so it’s like, it’s going to work out. People are going to have a good time. Andrew: It is. It’s true. And the reason that they’re going to have a good time is because I am focused on what I need to be focused on. I see a lot of interviewers… I can’t listen to interviews anymore. I get on my run, I listen to an interview and the guy will go on and on and on about the background of the person he’s interviewing. The douche.

I’m about to listen to your interview for an hour. I’m committing to an hour. You don’t have to load me up on this back story right now. Let the story unfold. You know? You don’t have to give me this big thing. What they’re doing is they’re insecure about their guest and their place as an interviewer and they’re trying to prop it up by saying see how impressive this person is. You know you should love this. You should love me and that’s pro. They should take the beads and they should be saying the mantra, I’m a pro.

Alright we have to continue here. You don’t have much to teach me about how to get traffic, because you’re saying it just kind of happened because you gave it time and you built a great product. What I need to know is about charging. You’re taking a product that was free.

Chris: Let’s get to that.

Andrew: How do you get to charging?

Chris: So I leave Hubspot, because I decide I’m going to run this business full time and I go on what I remember was the first entrepreneur, man- cation. So I went with Noah and six other guys. And so we went to Costa Rica and we hung out for a week and it was just an awesome time. We talked about our businesses, things that we want to do, everything, right. And literally all of them were users of the service and they all said that they would pay. And they were like, “Dude you have to start charging for this.” And I said, “Yes, I am going to.”

So it took me, I don’t know, just another month or so, and this was actually interesting, because a lot of people forget that once you switch to being a business, I had to go create the business bank account, I had to figure out the Gateway and the recurring billing and it all of a sudden got more complicated, but sure enough I did it and I started charging on January 1, 2011.

And so I said to my users, “I will give you, if you are an existing user and you sign up to pay, I will give you 50% off for the first year as a thank you for having been already an existing user who will pay now.” And a lot of people took me up on that. So I started getting revenue in and like literally every month it was just a nice increase. And I don’t even know if, like at this point I don’t even have access to the data anymore. I forget if it was like… It was just steadily increasing. It was just very linear, very organic, and it just kept going.

Andrew: Because you’d still give people free use of the product, until they hit a limit and then they got an e-mail saying you’re about to lose it unless you pay.

Chris: Yeah. So there was a freemium plan. I started out at, I believe, 33 reminders a month, which is actually a lot, and then I said like personal plan, which is $5 a month, got 100 reminders and it gave you a couple more features and then there was like a plus plan at $250 and a premium plan at $1,000. There were literally people from day one using up to 1,000 reminders a month. They were more than happy, apparently to pay $15 a month. That was also great validation on just the fact that high volume users were willing to pay that much.

Andrew: How do you know where to draw the line, what’s free and what’s paid?

Chris: I had a friend help me with this where we basically charted a graph of all the users and looked at where there were inselection points and usage. The question was, can I set a free limit that was just below where people really start to ramp up, so that I can start seeing if those people convert.

Then, literally after six months I lowered it to 25 reminders, because I think Noah said to me, “Why are you giving away so much free, somebody doesn’t need that many reminders to see the value in your product.” I lowered it to 25, then by the next year I lowered it to 20, and I kept it at 20 for the next two years. Because, I felt like it was a good number.

The other thing is that I always did it so that when you had five reminders left on the free plan and on any plan, it would then email you then, and the reminders would be like, hey you only have five reminders left, you should really upgrade its really easy just click here.

Andrew: Today I see it’s ten reminders.

Chris: Yes, things have changed, but we’ll get to that later.

Andrew: What is there to get to with that? I don’t want to forget that.

Chris: No. I just mean, that’s not my decision.

Andrew: Oh, the sale. Yes. We’re going to get to the sale in a moment. What you’re saying to me is, you said where is the break off point where someone goes from being a casual user to a heavy user, and it seemed to you it was in the 30s and that’s where you went with it. There was no way of telling and then you started to lower and lower it, so you could capture more potential users.

Chris: Correct. The thing was I didn’t think it was going to make . . . It might make the user stop using my product for that month and maybe they would look for an alternative or something. I just knew, also that the prices weren’t that high and theoretically you got a 30 day trial and you can cancel at any time. Somebody could of, if they were desperate enough, they could of signed up for the trial, kept using it and then, cancelled.

But, they would of only been able to do that one time. But, even so I said, I’m going to keep lowering this to see how many more sign ups or people convert into a trail and look at that data. Because, that was the only thing I could really do, it’s like here’s this product that’s useful, there’s a free plan, okay lets restrict this a little. I didn’t restrict this on . . . Yeah. Sorry, I did lower that for everyone. I didn’t grandfather anyone in on the free limit. I obviously, grandfathered people in if I raised a price or something, but that was different.

Andrew: You told April in our pre-interview, see we do research and we do pre-interviews with guests. You said, but there was a moment where all I saw was blackness. If I sell what I’ll owe, this is about selling the business, not selling . . . Did you have any hesitation about selling to people?

Chris: Yeah, of course.

Andrew: You did, about asking them to pay money? Even though Noah told you, you should charge?

Chris: Oh, about charging for it. No. Not really, once I had that conviction. There’s definitely a hurdle. If you ask Noah this question, he’ll be like, hell yes, Chris was like hesitant to charge. He should of charged way sooner. But, for me it was also this, once I went full time on it, I had no other option on it.

Andrew: I see.

Chris: I was doing this bootstrapped and it was like this is do or die, I’m going to make a business out of this.

Andrew: All right. Then, why’d you sell?

Chris: There’s a lot of factors to that. One it’s always good to go out on a high note. Two, I thought about the competitive landscape and what I needed to do to either grow the product, whether it was money, skill set, etc. Then, three it was like I’d been running the business about full time for three years and it was like, is this what I want to keep doing or do I want to move on and do something new. I had gotten offers before that I had turned down, but this one was good. It was really good, so I was like.

Andrew: I remember actually I was a user of the product. I still use it. And I remember I would email you issues and you would email me back. Often, you’d tell me, “No, you can’t have that” or “You don’t understand how this product is.” But you’d respond which is cool.

Chris: Yeah.

Andrew: And there was one time were you told me, “I’m thinking of selling the company” and I’ve never told anyone. I always keep these kinds of things secret but it didn’t happen. Why not?

Chris: I need to know when that email reply was sent to you because . . .

Andrew: Why?

Chris: . . . the first offer or that was the most recent one that . . .

Andrew: Pick any one. Why did you turn people down? Was there not enough money? Did they want you to spend more time? Did they push you to earn it out?

Chris: So, okay, there’s a couple of things. So, one, the stipulations of the deal. Do I need to come with the deal? If so, how long? And so one of the first offers I got they were like, we need you to rebuild this yourself in another language you don’t currently know. And then they were like, Andrew, we’re not going to pay you to do it during that time. And I was like, this is a terrible deal. So I was like, no. I was like, thank you but no.

Then the same people came back to me, and they were like, okay, things have changed. Now we’ll just give you something that was okay, and you don’t have to come with the deal. But again there was something weird about it in the end, and I was like, no.

Andrew: What’s the weird thing about it?

Chris: Whether it was like, you still need to rebuild it or you need to join us for a while, it was just one of these things that there was a string attached versus like, you get to go. And so, yeah, those were the kinds of things. The other thing to think about and this is true for every entrepreneur and I hope they think about this.

When you have a subscription business, if you start making a thousand dollars a month more in revenue multiplying that by 12 is big because wow, you’re making that much more a year. Then you think about someone coming along to buy your company, and now you’re multiplying that again by some multiple.

Andrew: I see. Multiplying your annual revenue by a multiple to value your company.

Chris: Yeah. So it’s like when people are thinking about their monthly revenue, every little increase in multiplied so many times that it can get big really quickly. So if you just keep focusing on growing top line, I’d like to say profitability, keeping your margin good but you just focus on the top line and keeping that moving up. You earn a subscription monthly or whatever business, you just forget how quickly things can grow when you’re looking at what happens in an acquisition.

Andrew: I see. So you’re saying, if I get more people in, now only is it going to increase my monthly revenue but it’ll increase my annual. And it will be consistently growing year after year too because people stay subscribed, and if I then have a multiple on that in acquisition then the exit amount is even bigger.

Chris: Yeah. So that’s why it becomes a really tough question when you say, “Should I really sell this thing” because if you’re making x and then you’re making 2x even the next year, all of a sudden that’s a whole x different than your acquisition potentially, let’s say.

Andrew: All right.

Chris: It was just a very . . . When you start . . .

Andrew: What do you do? If you say to yourself, “All right, I’m looking to sell. If I get in more monthly members who are willing to pay, then I get to increase the amount that people will pay me for my company. I’ve got to go out there and get more monthly members.” Where do you get those? What do you do? You weren’t buying ads.

Chris: No, I wasn’t.

Andrew: Do I see a little [??]?

Chris: No, so this is where you would potentially . . . I could have gone back to Noah and say, “Hey, I want to do a third AppSumo deal.” His network has gotten bigger. His email list has gotten bigger. So I can say, “Hey, every six months or a year let’s do another AppSumo deal.”

Andrew: So you go back to him. What else did you do to get more members?

Chris: Obviously lining up product developments with press so that I can constantly stay in the news. And that’s no guarantee because people maybe won’t cover you. Maybe you’ll get barely any traffic. That’s fine. I think the biggest thing which I did not do was actually hit up my own customer base for more tweets, Facebook likes, promotions, anything. I didn’t ask them to do anything for me when it came to that kind of stuff. I had ideas for partnerships, I literally thought of features that were value add focused solely on just customer growth.

Andrew: Did you get to release any of those?

Chris: No, because the opposition happened.

Andrew: Okay, so you didn’t ask your customers to Tweet you’ve got Noah to do a second AppSumo Deal, but more, right. You said you tweaked the product in a way that allowed you to go after press. That seemed to work. What did you do there that allowed you to after press?

Chris: I mean, so here’s the other…I built the product, but I tried to think about refinements that were actually worthy of talking about. But, even then what I was going to say is that I think the real focus is almost more the long tail of so call press. So, people like [SP] Keep Crunch I never explicitly go after them.

Oh, so here sorry, let me interrupt my own self and say. One of the biggest things for follow up and this is, in fact, where I got the most traffic over time. Customers like yourself, like Ari Mizel, who runs his program, and I feel really bad because I’m not saying at the moment.

Andrew: I’ll look him up.

Chris: So, Ari has done all the right things as an author and producer of a program for getting his content out there and getting people to know about.

Andrew: It’s, he was on [SP]Mixergy D two.

Chris: I got you. I can’t believe I blanked on that in a moment, sorry, Ari. So, anyways he was just a customer loved the product it was totally ingrained in his system. He would get a guest post on articles, and he would always mention follow up as part of his system. So, essentially he’s doing the promotion for me because he was just a customer who loved it, right.

Andrew: If I were to reproduce what you did could I go back to…if I have a productivity tool could I say, you know what, Ari Mizel is an influencer who likes to blog about tools that are effective. I’m just going to get my product in his hands. I’ll even give it to him for free, because if he uses it then I’m more likely to get promotion from him.

Chris: Yes.

Andrew: All right but that’s the thing to say, who is out there? Who is a potential power user of my product? Who’s a power user of other people’s products and talks about it? I’ll put my stuff in their hands. The other thing that you did was you lowered the limit on the free, so that increased the conversations from free to paid, OK. Then when it was time to sell, how did all these guys discover you to start offering you money for your business?

Chris: So, it wasn’t some crazy thing. I had a couple offers but basically it’s kind of the classic network effect where I had met this guy a couple years ago, and he, and I had talked about the business. He was interested, but it was like it wasn’t time for me to sell nor any of that. And, he came back to me and so when you came back to me I said, ”Okay, this is more interesting.” Then another offer came in that was kind of interesting. So, I started evaluating and actually it took a little bit of time but basically I said this is actually a really good deal. And, so it was not a crazy process, it was fairly straight forward…

Andrew: You met him at a conference?

Chris: No, so I originally met him through Dan Martell. Dan has always been a really great guy in terms helping entrepreneurs obviously you see what he’s doing now with He was a user of the product many years ago, and he and I talked on the phone again. He was just willing to help me out like introduce me to whomever, and that’s how the whole relationship started.

Andrew: I see so once again an influencer, who understands your stuff.

Chris: Yeah.

Andrew: Who knows it? Okay, is the person you talked with is that Jonathans Segal.

Chris: Yes.

Andrew: It is. Who is Jonathan Segal? I don’t know much about him except that he’s an angel investor, but apparently he also owns products on his own.

Chris: He’s a very, very smart guy he’s actually…his background is computer science, so he’s a techy. But, he’s a really, really sharp business guy. Very good chess player in the sense. He’s just done well for himself in business. He’s been to DC, he’s been entrepreneur and his last company he sold to Rackspace, and it was a similar model of I think like kind of buying and building up different properties in the cloud tool space or, sorry, developer tool space. And so he’s the kind of guy that looks at things that he thinks have bigger markets and that he can grow. And he’s not working on it personally, but he puts a team together that basically grow this thing until what it can be.

Andrew: I interviewed his co-founder at Exceptional Cloud Services, Teri Wilson.

Chris: Yeah.

Andrew: I didn’t realize that it was the same person until now. As you’re talking about it I realized it. So he doesn’t have much about himself online. It’s very hard to figure out that he is even the guy behind You told us the company you sold to was . . . What’s the name of the company?

Chris: No, no, no. I’m saying he’s behind the company that . . .

Andrew: Right.

Chris: Yeah, yeah.

Andrew: I had no idea he was behind the company. I don’t even see it on his LinkedIn profile.

Chris: He’s an international man of mystery.

Andrew: Yeah, what’s the name of the company?

Chris: The acquirer?

Andrew: Yeah.

Chris: Argon Technologies.

Andrew: Argon Technologies.

Chris: Yeah.

Andrew: Got it. See, I didn’t even know anything about them. I looked up Argon on Google. Argon Technologies, I end up with, a page that says dial up wireless and business. It can’t be the same company.

Chris: No, no, sorry.

Andrew:, all right. No, not that one either. I’ll have to look it up later. See, international man of mystery, Argon is A-R-G-O-N?

Chris: Yeah. They just literally don’t have a web page up. Trust me, they are . . .

Andrew: I know he’s a solid person.

Chris: In fact, if you Google there was just like a press release put out on the new follow up team product, and they say like, “Argon Technologies, a blah blah blah company based in San Barbara, California.

Andrew: I see.

Chris: And there’s a picture of . . .

Andrew: is down. Thankfully I can go back in time and see that at one point he had a picture of himself and I’m guessing his wife from 2002 holding champagne glasses. And that’s all that was on the site, a man of mystery, I’m telling you. So what is the blackness related to selling the company?

Chris: So in my thinking about selling this, right? So my career has been very like, I have gone from one opportunity to the next or I’ve gone to work on the next thing. And there’s been a very nice logical flow to everything, whether it was taking an opportunity that came my way or just going to something that I knew I had lined up. I did not purposely sell Followup because I was off to do my next thing. I’ve had ideas. I’ve got interest in other spaces, in other industries, et cetera, but I did not have a working product that I’m going to start working on this as soon as Followup is done for me.

So in that moment, you’re like, the business is making money. Everything is going really well. It keeps growing. It was like, “Why am I selling this?” You see this like this void of what’s next and you just don’t know, but at the same time that is the scary part and that’s where it’s kind of like jumping off the ship as an entrepreneur. It’s being like, I’m going to swim and figure it out.

Andrew: And now you’re looking to see where you’re swimming to next.

Chris: And now I’m like, I’ve got a couple of ideas, but I’m still talking to people and I’m open to opportunities. It’s nice to be in a position where I can think about, “Am I going to fund the next company myself” similar to bootstrapping Followup but with more capital.

Andrew: What did you sell the company for?

Chris: I obviously can’t tell you that.

Andrew: Did you become a millionaire?

Chris: We’ll see.

Andrew: Oh, because there’s an earn-out?

Chris: No, it’s not an earn-out but that’s obviously a personal question in general, and there’s just other things that are working.

Andrew: You mean, other expenses potentially that could reduce what you’ve taken.

Chris: No, I should have just answered that as like, no comment because when I can make a comment, then it’ll seem normal and not like juicy or something because I don’t want to come off weirdly.

Andrew: You’re not coming off weird.

Chris: Okay.

Andrew: Let me ask you this. You have a girlfriend. Do you ever feel like, boy, this is now changing my relationship with my girlfriend?

Chris: No. She’s an entrepreneur as well and she could care less about money.

Andrew: If you got married, would you sign a pre-nup?

Chris: No.

Andrew: You would not?

Andrew: Because, you don’t believe in them or because you’re so in love and trusting?

Chris: Because, I think it’s a lot easier in a case where you’ve been with someone before you had a lot of money.

Andrew: I see, yes.

Chris: Then, there’s not an issue of where they with me for me. I’m not against pre-nups, I’m sure they have their place, I think there are a lot of circumstances where I think they’d work . . . I think it’s a little premature to even ask the question.

Andrew: Is it weird now when you friends expect you to buy drinks now when you’re going out? Or, do you expect yourself to do it, no?

Chris: You have to remember that there’s a very large . . . I think there’s quite a ramp up time and a mentality of how you are, right. First of all, more dollars in the bank, it doesn’t change anything. I didn’t need more in my life. I live a very comfortable life in Boston. I don’t live a lavish life.

Andrew: What does the rent go for at your place?

Chris: I happen to of had a really good rent deal for where I live in Boston, it was like $2,200 for the last couple of years for a two bedroom. It’s all of sudden rising rapidly, because I think things are going nuts with rents lately, but even then, it’s been $2,200 for the past three years. That’s really reasonable for where I live in Boston.

Andrew: That’s less than half than what I’m paying here in San Francisco, and I don’t get much benefit for that.

Chris: This is why when people talk about, oh you should move to San Francisco, and I’m like why . . .

Andrew: Why?

Chris: Double my cost of living, I mean granted there’s all the merits of being in San Francisco, which . . .

Andrew: What’s the biggest benefit? Is it being able to travel with your girlfriend or is it lack of worry?

Chris: Wait, what are we talking about?

Andrew: Of having made. You did it and you’re telling me I sold this company, but I’m still living in the same place, paying the same rent, my friends haven’t really seen a difference in who I am. What is the one big difference in your life because of the sale?

Chris: By the way, I have to say I have bought people dinner and drinks, and things like that wherever a thank you has been owed. Where they even did something little for me, I’ve been like this is on me, obviously thank you blah, blah, blah. I tried to be generous and taking people out who I think [??] . . .

Andrew: I’m not calling you cheap.

Chris: I’m just saying that . . .

Andrew: You’re not Noah [??] generosity, but your still incredibly generous. I accept that.

Chris: What generosity, I was going to say, I think he makes a different joke to. On the other side.

Andrew: Okay.

Chris: Wait. Okay. Say that again. You’re basically like . . .

Andrew: What’s the benefit? Is it lack of worry, what is it?

Chris: Here’s the thing, I think a lot of people have different personal views on wealth. I’ve always taken a bit of the Warren Buffett approach of don’t lose money. But, that also implies no risk, which isn’t the case, it’s more about . . . I think the best thing for entrepreneurs is the flexibility to maintain a cheap life style while they were bootstrapping or starting their business. That is something I got to do with Follow Up. Because, I was comfortable from working, and investments, etc. I can live a very cheap life style, but very comfortable, it wasn’t like cheap, cheap. By the way, I absolutely despise the roman thing that’s associated with startup entrepreneurs.

Andrew: What is it, being roman profitable, just being able to make enough money to live on roman.

Chris: Yes. Which I hate that, because I would say, first of all you can eat something healthier for the same price.

Andrew: I see, yes.

Chris: Because, that’s my other interest, health and nutrition, which if you ever want to talk about that we’ll get into it. I think the main thing is people have to think about what they want and what their goals are. I obviously, would like to become more wealthy and more comfortable, but for this point in my life I do not need anything more. The whole point is why would I spend money on something versus save it, invest it, whatever for the future. Because, that’s where the flexibility comes in do I want to buy a house, do I want to buy a condo, or do I want to start another company and fund the whole thing myself? I’ve got the flexibility.

Andrew: All right. I’ve asked awkward questions here in this interview. I think in private I get away with and I’ve learned how to ask awkward questions much more comfortably. In the interviews I am still not there. Like, I can ask about people’s sexual habits and I can ask about how sex has changed after money. I can ask about pre-nup. It’s very tough. I am getting better about it. And I have to keep working at it.

My most awkward moment, by the way, asking about this stuff came in an interview with this guy, Andrew Fashion. He asked me to change his last name to the name that he is going by now. Kid made over a million dollars selling My Space jeans. Then, he made one little change everything started to fall apart and he still is, he’s doing well but I started asking a couple of personal questions and realized this is not working. I am not yet there.

But I’d like to be there because I think this is all part of the entrepreneurial experience. Whether we get pre-nups or not. What happens in our lives after we sell. What happens when we’re, you know, at that awkwardly low period where, where we feel insecure.

All right. Anyone who is out there who wants to see that awkward moment. I really urge you to check out the interview I had with Andrew Fashion. He’s a great guy for putting up with some of those questions. And he had a great story.

All right. I think we have gone over time. I didn’t even get a chance to ask you about your favorite books. So I am just going to read them right here. Einstein Factor and you say it’s because of increasing your intelligence as much as possible. And Antifragile. Why Antifragile?

Chris: The book teaches you to appreciate…so, obviously his, his two books before that is Fooled by Randomness. Right? I think that the whole thing is again remembering that there are a lot of forces at work and a lot of factors that play into system dynamics. And so, no matter how brilliant you think you are there is an element of luck and an element of randomness to everything. And it gives you a new perspective when you look at how the world works.

I actually, the funny thing is, I met him at the Paleo conference last August which was really odd that he was there. But it was because he was actually talking about his notion of the system of the human body and why basically lifting weights was the number one thing you could do to increase your likelihood for health success and longevity.

Andrew: All right. The author of Antifragile. All right, I was going to go tell people to go check out your website but I don’t see much here on Maybe the best thing to do is to follow you on Twitter.

Chris: Yes.

Andrew: It’s at…

Chris: Yes, follow me on twitter at ckeller. On my, on my personal blog is was just a post just you know, in case you guys want to follow me on my next adventure. Just like, sign up there, put your email address in. I have not even sent an email out on it yet. So, you are not going to get spammed…

Andrew: Here is what I am going to suggest to anyone out there who is at the earlier part of their career. People who are later on should go on out there, go out and take you out for dinner and talk to you more about how you’ve built up this business and what you are doing next. Someone who is earlier on, I think you’d be a great mentor because you really care. I don’t even know that you want to be a mentor to anyone. And because of the way you think about starting companies. And because your website needs a little more content.

And so I could see someone out there in the audience saying, “You know what? I need to get started with this guy. I’m going to help him with his website. And as, as a part of helping him I am going to get to know him. See how he is thinking about his next projects. See what he is up too and see if I can work with him on the next thing.

Chris: By the way, and I will say that I was terrible with follow-up about not having a blog. I did not have a blog for I would not make that mistake in my next company. And I would have written out more of my thoughts and observations about the world in that space on the blog.

Andrew: And I think that you had a lot to say.

Chris: Yep.

Andrew: All right. Thank you so much for doing this interview. Thank you all for being a part of it. Bye guys.

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