How long should you be willing to fail before giving up on a startup?

How long are you willing to try and fail, again and again, before you give up on creating a profitable startup?

A lot of people would just try once and say, hey—this just doesn’t work. I’m going to move on and accept that this is not going to work.

Today’s guest didn’t do that. She built a product and couldn’t get a lot of users. Then she built another one that got users but no revenue. Finally, her third company was a hit and is growing. I invited her here to tell us how she did it.

Bridget Harris is the co-founder of YouCanBook.Me, an online scheduling tool in the UK.

Bridget Harris

Bridget Harris

You Can Book Me

Bridget Harris is the co-founder of YouCanBook.Me which is the fastest growing online scheduling tool in the UK.


Full Interview Transcript

Andrew: Hey there, freedom fighters. You know me. My name is Andrew Warner. I’m the founder of Been doing these interviews since 2008. I think I might be the originator. All right, that’s too much. There was one other person who was doing it. I copied the idea. And I’m so proud to have been doing this for over 1000 interviews with some of the world’s most proven entrepreneurs, and we do them in a way that allows you to learn from them so that you can build your business based on what they’ve learned.

And one of the things I’m proudest of is that a lot of people who I interview here have listened to these interviews, and built their companies while listening to these interviews, and with what they’ve learned here.

All right, so let me ask you this. As a listener of mine, how many times are you willing to try, fail, and try, and not get it to work before you give up on creating a profitable startup? And the reason I ask you is because a lot of people who try it once say, “Hey, you know what? It just doesn’t work. Everything that I hear on Mixergy, everything that I see online, it’s just not really the truth. I’m moving on, and I’m going to accept that this thing is just not going to work.”

But today’s guest didn’t do that. She built a product, and frankly, couldn’t get a lot of customers for it. Then she built another one. This time she got users for it, but there was no revenue coming in. Then she built another one, and that’s a hit, and that took off, and it’s got good revenue and good user base, and it’s growing. And today, I invited her here to talk about how she did it.

Today’s guest is Bridget Harris. She is the co-founder of You Can Book Me. Let me tell you what they do. You know how sometimes you have trouble booking a time with someone? You ever go through the back and forth where you email someone five available times, they tell you none of them work, they send you four others of theirs, and you tell them none of those work, and you go back and forth.

Well, what You Can Book Me does is simplify it. It allows you to send a simple link with your calendar and all your availability on it, and people can book a time with you easily. And that’s the business that has worked. They bootstrapped it. And I want to find out how they got users, how they figured out the software behind it, how they keep improving the software, and how they grow.

And this interview is sponsored by two companies. There’s a new one here today. It’s called Kickoff Labs. I’ve actually had the founder here on Mixergy, but he’s built it so much since I had him on here. The whole idea behind Kickoff Labs, and I’ll tell you more about them, is if you want to grow your mailing list exponentially, they’ve got a cool new way of doing it, and I’ll tell you more about why you should go check out Kickoff Labs later.

And it’s sponsored by TopTal. Later on I’ll tell you why, if you need a developer, you’d better go to T-O-P-T-A-L,

First, Bridget, good to see you here.

Bridget: Hi, Andrew. How are you?

Andrew: Good. Hey, your husband Keith is, like, some kind of software addict, or software creating master. He constantly, you told me, creates software. In fact, when you guys were looking to move houses, what did he create for you?

Bridget: He created a web application called Price Per Square Foot, which allowed . . . because in London, when you’re looking for houses, it’s incredibly difficult to judge the true value of a property, because, you know, they’ll turn one room into four rooms and call it a four-bedroom house. So it allowed us to put in all of the square footage of each room and kitchen and bathroom and so on, and then come up with a number, which is the price per square foot. And a brilliant little kind of DNA-style strip showing you what proportion of your space was being told it was living area, whatever.

So we got completely obsessed with it for about a year when we were house-hunting, and I always told him . . . he’s probably still got the code somewhere. It’s still a lovely little app. But he never went and . . .

Andrew: What other apps has he created for you, either personally or professionally?

Bridget: So, well, he does a lot of tinkering around with, you know, gaming type, silly stuff. And he’ll do, like, as a hobby, on the weekends. Professionally, when I was working politics, I used to get him to do campaign software, sort of all sorts of voter identification, database-type stuff, straightforward websites, and, you know, ways to communicate with people.

Then he’s done all sorts of productivity-style web applications. So time management, so project management, time tracking, the kind of scheduling, the suite of scheduling tools that we’ve done. And we’ve done four different types of scheduling. And, yeah. I mean, anytime that there’s a problem, a business process where there’s a problem, Keith is like any other coder, and his reaction is to dry to write a web application to fix it.

Andrew: Impressive. And so this guy who keeps creating software at one point was working for a search engine company, and they asked him to create what for them?

Bridget: So he was . . . yeah, he was contributing to the general search software that they were selling, but they also needed a project management and time tracking software, which he wrote. And then he subsequently wrote another version of that for another client, and then he wrote, actually, a version for it for us a couple of years ago, as well. So he did a lot of experimentation and understanding of how to deliver, essentially, a web application, as opposed to software that runs, you know, on people’s machines.

Andrew: And there was an “aha” moment that made you think, the world is changing, here’s our opportunity. And as I understand, it had to do with this time management project software, or time and project management software, that he was doing over and over again. And one client, I think it was a search engine client, was charging for it on a monthly basis, and you said what?

Bridget: Yeah.

Andrew: How did it change your worldview? What did you start to think?

Bridget: Absolutely. So when you understand the technology behind web applications, and you realize it’s platform-independent, and everybody can just run it through a browser. And this was in 2002. And then you get people to subscribe. Even though we didn’t understand, or we had no knowledge at all of the SAAS ideology that we now all inhabit, that we live in right now, we understood that if Keith could write a web application we could sell on a subscription basis, that we could make our millions.

I mean, quite honestly, it sounds ridiculous now, but at the time we sort of thought, yeah, we’ll just write something, we’ll try to find a . . . you know, Keith will think of a problem that he could solve, write the web application, and then, you know, we’re done. Early retirement.

Andrew: And you know what? On other podcasts, that’s the way it seems. They make it out like if you find your one answer, your one SAAS, then you’ll get money on a recurring basis easily. Here we know that it is harder. And in fact, the very first thing that you created was software to do what?

Bridget: So on that basis, when we decided we intentionally wanted to write software for ourselves, entrepreneurially, we did a survey-building tool. So Keith wrote . . . you know, it sounds very simple now. It’s just a web form that you build on the basis of trying to gather information. So now we see this is an incredibly simple thing, but at the time, you know, 13 years ago, the idea that you could . . . any ordinary non-web person could build a survey to collect information, send the link out, people would look at the link, follow the information. I mean, we built TickBoxer that was probably no more complicated than Google Forms or, you know, there’s SurveyGizmo and SurveyMonkey, or something.

Andrew: We’re talking about 2003 when you came out with that. I don’t know if . . .

Bridget: That’s when, yeah. That’s when he started.

Andrew: Google Forms I don’t think was around at the time. I know there were some options back then. I think, like, Freedback, and a bunch of little players were there, before SurveyMonkey gobbled up the whole market, it feels like. Why didn’t it work?

Bridget: So we . . . well, it’s a very good question, and I think the market that you’ve just identified was probably one of the issues, is that we wrote TickBoxer just before everybody really understood what on earth we were doing, so it was very hard to get off the ground and convince people to use it. So the people who used it were not surprisingly me, and I was in a job in local government, and I was a senior manager, so I had, you know, I could start using it for running surveys of counselors, as it was. So I could suddenly do a survey of 500 counselors, and get the point. But I’m obviously on the inside.

We got one of our colleagues, a previous client, who’s also an entrepreneur, he used it to collect information on the street for his pedestrian survey modeling. I mean, it was just a bit random.

But we couldn’t . . . when we told people, “You can get this survey building tool. It’s called TickBoxer, and it will help you solve a problem.” I don’t think people understood that they had a problem. So, and then we . . . SurveyMonkey definitely was around at the time, and obviously a much better funded company. Totally knew what they were doing.

And I can tell you the moment we gave up on TickBoxer was when we were at a party, and it must have been around 2004, so we’ve been doing TickBoxer for about a year. We’ve been using it. We understood a lot more about its functionality and its features and what it needed. And we were at a party, and somebody showed us WuFu. So, do you know WuFu, the . . . yeah, right.

Now, WuFu doesn’t claim to be a survey building tool. It’s a form builder. But we saw WuFu, and we saw that WuFu was taking advantage of all this really nice, you know, front-end, client side technology like JavaScript and Ajax, and it was looking lovely, whereas we were a service side, we were a Java application, it was all very, very clunky, really.

And we thought, my gosh, really, there is a very wide spectrum in survey building. There’s at one end the SurveyMonkey, you can do quantitative and qualitative research. You can add statistical validity to your answers, and it’s all very complicated. And at the other end, you’ve got a WuFu name and address form. And there’s a very big gap in between.

And we suddenly realized, we don’t know where to pitch TickBoxer. We haven’t got the resources to make it, like, as good as SurveyMonkey, but really, if you wanted it for a simple solution, I would use WuFu. So essentially, it was one of those classic things, which is, we probably wouldn’t use our own tool.

Andrew: I see. Wow.

Bridget: So if you’re not going to use your own tool, you know, then we’ve just got to go home now. It’s not going to work. Because we had never thought, at that point, about taking on investment, or going for it full-time. We were doing this as sort of a part-time venture whilst we were doing other things. So we just didn’t have the resources to invest in that solution when we understood how complicated the problem was.

Andrew: And so then after that . . . well, first of all, you took some time, and then you came out with a different piece of software. This time you identified a clear problem people had. What was the problem?

Bridget: So the problem is finding a time for a group of people to meet.

Andrew: Okay.

Bridget: And it, you know, that problem is time immemorial, really, and it was . . . actually, it was one of the guys who worked with Keith in one of his previous clients who said, “You know what, Keith?” Because he’d worked on TickBoxer with Keith, so he knew TickBoxer, and he knew that we were looking for an issue. And he said, “You know what this problem is, is that I’m at univer- . . . ” He went over to MIT, a guy called Frank, and he said, “It’s really hard at university for a group of people to find a time to meet for a seminar. I think you should build that.”

So it was a credit to him, really, and Keith had to think about it. And he went through several versions of When Is Good. So he wrote it in HTML and Java, then he rewrote it in Flex. I don’t know if anybody remembers Adobe Flex. It was a very weird . . . it was kind of a precursor to quite a lot of the very nice libraries that you have now, but it was a kind of a classic Adobe, you know, immersion sort of technology that you’re in.

So he rewrote it in Flex. Then we realized Flex was ridiculous, so then he rewrote it again. And that was in around 2008.

Andrew: And is it fair to say that with TickBoxer, you didn’t start with the problem, you started with an idea. But with When Is Good, the software that allows people to find the perfect time to connect with each other, that there you did start with the problem, and you almost had to be convinced to create the product, but you knew at least there was a problem there.

Bridget: I think so, yes. I think the fact is that TickBoxer was something that, you know, Keith . . . and I think this is probably true to say of a lot of issues when people are trying to find a problem, is that, you know, if you find yourself inventing the problem in order to provide the solution, you know, you’ve got to . . . Facebook was a problem that was invented in order to be solved. And it’s actually, you’re on much stronger ground when the problem exists already. And finding a time for people to meet was an obvious problem with a very obvious solution.

So Keith built a grid of times. I mean, it’s as simple as that. You build a grid of times, everybody paints over the times that they can do, and the program does the hard work of telling you which time everybody has in common. And that’s basically what it does.

Andrew: And it’s up right now. I went to, and I saw a video for about a minute. It shows how the software works. And it’s pretty straightforward. And I could see also that it’s got some virality in it, where if I’m using it, I’m not going to use it on my own. It just doesn’t make sense. I have to pass it on to someone else who I’m about to meet with, and maybe even two other people. Because if it was just one other person, maybe email would be an easy way, but if it’s three other people whose schedules I’m trying to coordinate with, just too tough. Four people, too tough. So . . .

Bridget: I mean, I’ll tell you that some of . . . it was a while ago, but the last time I properly looked at the stats on When Is Good, we were doing 20,000 responses, 20,000 events a month, and then there was around 100,000 responses. So there was basically a one in five. For every one response, one event, you’d get five responses.

Andrew: How did you get users for it?

Bridget: Well, Frank at MIT started using it.

Andrew: Okay.

Bridget: Then there was the kind of . . . there was that viral growth around universities. So, you know, I think it started off reasonably slowly, and we were kind of, as I said, we went through two or three different versions of the tool. So I can’t remember, quite honestly, how quickly we grew within those . . . in those different versions.

But the big change for When Is Good was that we were featured on LifeHacker, and basically that went right up. And we just, like, the servers went crazy one day. What’s going on? And we saw that LifeHacker had reviewed us. This was in 2007, so I remember it, because, you know, we got, like, 20,000 people creating When Is Good accounts on that day alone. And then, of course, that virality just took off.

So since then, we’ve basically never looked back. I mean, we were covered by TechCrunch about a couple of months later, so we got two hits on LifeHacker and TechCrunch, and various other PR that we did on When Is Good. And it essentially started to double every year, you know, in . . . yeah, sort of pretty much, sort of 50% growth every year, probably, actually, if you even it out. It grew faster at the beginning. And at the very beginning, it was really growing strongly all over the world, in other languages, and all sorts of things.

So we were really confident about it. We were really excited about When Is Good. We felt that When Is Good was our baby, you know? We’d hit gold. We were ready to invest and work hard on it.

Andrew: Yeah. Look at this. This is Gina Trippani, who basically built up LifeHacker.

Bridget: Yeah.

Andrew: And since then, she’s moved on to really good things. And I’m reading the article. She’s saying that it’s similar to, and she lists a competitor. No registration’s required at When Is Good. Just simply fill out the calendar with your proposed times for a conference call, and that’s it.

Bridget: Yeah.

Andrew: But the no registration seems to be a key issue. You guys still talk about it on the site. Gina picked up on it. But it’s a little scary to not ask for registration upfront, because it means that if someone doesn’t follow through, you can’t follow up with them.

Bridget: Yeah. So in fact, the only support we get on When Is Good is people who have lost their results code. So, you know, I mean, that’s it, really. And people love it, because, you know, people who just want to quickly set up an event and send that link round. There are, I mean, and, you know, in terms of, if people want to understand what our thinking was about When Is Good, it’s hopefully useful for other people when they’re thinking about their own product. You know, you have to think about how you’re solving the problem which is going to be valuable to other people.

So as you said, you know, when you’re trying to arrange a time with two other people to meet, instinctively people think sending an email is going to be quicker. So with When Is Good, we designed it explicitly with the logic of, it has got to be quicker than email. This has to feel quicker. Otherwise people will just use email.

And so the other thing about the interface of When Is Good, a long, long, long time before we knew anything about UI or how, you know, interfaces work, we knew instinctively that we needed to keep the settings all on one page. So you don’t leave the settings page. You don’t go through some kind of wizard to set it up. You go onto the When Is Good to create an event. Everything is there, you know, in terms of setting the rules for the date and times that you want. You hit go, you’re done. So it is a very quick way to create the event.

Sadly, it hasn’t had a lot of love, really, in the last couple of years, because that’s what we can talk about, you know, shortly. But it still does well. I mean, I look . . . and we’ve got 400,000 people using When Is Good. So it’s really, as a kind of a standalone web app, it solves a problem, it still solves a problem for people. There’s some people who are, you know, die-hard When Is Good fans.

Andrew: You started out with the idea that you were going to build a web app that was going to make your millions easily, because the software would just charge . . . you would charge for the software, and people would get to use it, and you wouldn’t have to be there to hold their hands.

Bridget: Sure.

Andrew: Where was the revenue going to come from for When Is Good?

Bridget: So When Is Good is a freemium tool, in that you can pay . . . first of all, it runs ads, so we introduced . . . when we realized we weren’t getting a massive turnover of upgrades, we introduced adverts, which we’re not brilliantly happy with. Ads are, you know, the last resort in terms of trying to get revenue. But it brings in a trickle of revenue.

And then you pay $20 for a year’s subscription, and that removes the ads, and it also gives you access to, like, two or three extra features, like . . .

Andrew: Like more options for respondents?

Bridget: Yeah.

Andrew: You can say which times are perfect for you. You can export the results into Excel. How did you know that . . . why export to Excel? That doesn’t seem like it would be a huge need.

Bridget: Well, it isn’t, so not many people upgrade.

Andrew: I see. Okay.

Bridget: You know, universities, people with large events, people who are doing 70, 80 people, you know, will often want to get their data in a spreadsheet so they can start playing around with it. So yeah, it’s . . . I mean, we get a trickle of upgrades. And I don’t want to do When Is Good down, because I would love . . . I mean, there’s things to talk about. But, I mean, I would love to be able to fold some of the functionality in When Is Good into, you know, our future plans. And we kind of can go back to that group of users who have been very loyal, and used the web app, and give them something good in the next couple of years that will help solve their problem for them.

But, you know, the basic answer is that When Is Good is a social and leisure tool. So students use it. People use it for organizing gaming. Because it doesn’t, it handles time zones, so it’s very popular amongst gamers who want to find a time when they all, you know, run around . . .

Andrew: But it’s not for business. What you need day to day in business is a way for people to schedule a call with you, especially if you’re a salesperson. But rarely do we, as entrepreneurs or businesspeople, need to book with five other people and pick the perfect time. Usually someone takes the lead on that.

Okay. Let’s come back, then, in a moment and talk about how you got into You Can Book Me, where the idea came from, how that took off, and why the revenue started to fall in place there.

But first, I’ve got to say to anyone who’s listening to me that we have a new sponsor. It’s called Kickoff Labs. And here’s the idea behind Kickoff Labs. Email — if you’re listening to me, you probably know — is one of the best ways of growing your customer base. In fact, for us, if I had to give up my podcast audience or my email audience, I have to say, it would really be tough. But I know for sure that we make more revenue from our email audience than from podcast, because email is just so effective. People read email on the train. They read emails in the cars driving, I notice over here. They read emails in the morning before they even kiss their spouses, right?

And so if you’re an entrepreneur, if you’re building a business, you want to know, how can you get more people to subscribe to your mailing list to get on your email list? Well, one of the things that Kickoff Labs does is make it easy for you to grow your mailing list by, for example, incentivizing people. You can say, “Join my mailing list and you will get this PDF. Join my mailing list and you will get this free software. Join my mailing list and.” Right? So that’s one thing that they do. They make it easy for you to ask for people’s email address and give them the result.

The second thing they do is they have these widgets that incorporate into your site in a way that encourages people to give you their email address. For example, they have an exit intent widget that you can use as part of Kickoff Labs, so when people are on your site, nothing happens. When they’re about to leave, a little exit intent widget comes up that says, “Hey, before you go, you should check out our PDF,” or you should check out this report, or whatever. Give us your email address and you’ll get it. Right?

Now, those two things are not terribly new. Others have done it. I think Kickoff Labs does it really well, and you’d be happy to use them. But there’s one other piece that no one else, I think, because I don’t know of anyone else who’s done. And what Kickoff Labs realized is someone gives you their email address, most people do what? They say, “Thank you for giving me your email address,” and that’s it. Maybe they say, “Go check your inbox for a confirmation.”

Well, Kickoff Labs says, that’s a wasted opportunity. What if you can say to someone, “Tell your friends about this thing that you just liked so much”? I mean, you liked it, right? You just asked for it. Tell your friends about it. And — here’s the key part of Kickoff Labs — if you do, and your friends join, we will give you this reward.

So imagine this. Someone joins your mailing list, and you say, “Now, tell your friends, and if one of your friends joins, we’ll give you a 10% coupon code. And if three of your friends join, we’ll give you a 25% coupon code.” And so on. Or join, or tell your friends, and if one of them joins, we’ll give you a free day on the site, a free membership day.

Whatever it is, you now can incentivize the people who already love you, who’ve already given you their email address, who already trusted you. You can incentivize them, reward them for telling their friends.

And that’s the magic of Kickoff Labs. I’m seeing here a couple of posts on Reddit from people who’ve tried it. Here’s one where a guy on Reddit said, “Since we launched, over 2000 people have signed up, and 84% of our sign-ups have come from someone who signed up and later shared our page with a friend.” That means the vast majority of people, for this guy on Reddit, came from people who told their . . . who found out about it from a friend.

Here’s another one, Steven Turlick, who says, “Kickoff Labs gives a unique URL to share with your friends, tracks anyone who signs up from their special link.” And he says he got a 50% conversion rate on his landing page. That’s the cool thing about Kickoff Labs. They make pages and widgets that convert, right?

I don’t want to oversell it. I do want to get you to try it. When you do, you will be convinced. Write this down. They only signed up for, like, a four ad package, so I don’t know how often you’re going to get to hear the . . . here it is. It’s a long URL. Of course we’ll link you to it in the show notes. But you should write it down. They’ll help you grow your mailing list. I’m really grateful to them for sponsoring.

Bridget, that was a little bit long, don’t you think, as a sponsorship message?

Bridget: I think it’s really good, actually. I like hearing the . . . I think the way that you tell the stories is good. I think it’s interesting and valuable.

Andrew: Thanks. Yeah, I let it go long, because I was really happy to talk about them, and I thought that I was explaining it well and trying not to oversweat and overworry about the length of the ads. Because, like, in my head there’s a screaming man going, “It’s an ad. Shut up. Move on. Move on. Move on.” But I have to sometimes say, “Shut up, little man. I have to talk here. I think I’m explaining this fine.”

Bridget: [inaudible 00:23:14] People will listen, I think, actually. They don’t feel like you’re just selling a quick ad.

Andrew: Well, getting into your software, you then found a problem.

Bridget: Um-hum.

Andrew: What was the problem that led you to You Can Book Me?

Bridget: Okay, so . . . I mean, really simple. We weren’t making millions of pounds.

Andrew: Okay.

Bridget: Just suddenly, like, you’ve been working, slogging away for years, you know, and everybody knows this feeling. You’re slogging away, and it’s fun, and you’re learning a lot, but as a proportion of the number of people using you, we just weren’t kicking it, you know? There wasn’t enough people upgrading. And really, we could have spent a lot of time, you know, AB testing different features, or paid for features, or made it a premium only thing, or whatever.

But actually, what happened was . . . going back to that point that businesspeople, you know, weren’t using When Is Good, don’t need to use When Is Good, were using it to organize poker nights. They’re not organizing their business meetings using When Is Good. They were taking When Is Good as a grid, and they were sending the link to people to try to display their availability.

And I remember some of it was people who were maybe locked into corporate software, and they weren’t allowed to do anything within their own machines. But because When Is Good just runs on your web browser, they could create availability on a When Is Good grid, which had nothing to do with the IT department. So they weren’t, you know, breaching any download problems. And sending that link.

So, and they were talking to us about it, and what they wanted was for anybody who, you know, recognizes the You Can Book Me grid, they wanted to make them clickable. They wanted to make those times, that square box, clickable, and then capture it. So they wanted to seal the deal. They didn’t just want to say, “Here’s . . . I’m publishing my times.” They wanted to say, “And 2:00 on a Tuesday is my time. I’m booking it.”

And so Keith originally, you know, planned to write You Can Book Me as sort of an add-on, effectively, to When Is Good. So we still assumed When Is Good was going to be our main primary tool. It’s just that for the people who wanted the booking side of it could use You Can Book Me. And that’s how You Can Book Me came about.

Andrew: It’s interesting that they wanted this feature so badly that they were willing to use your current software, which wasn’t meant to let people book with them, they were using that as booking, and complaining you that it wouldn’t go as far as they needed. And you found out about it because, I’m guessing, you saw customer service emails come in.

Bridget: Yeah, exactly. They started talking to us. I mean, it’s one of the things which now is sort of seen as an absolute given in anybody following particularly lean startup type philosophy, which is you’ve got to listen to your users. You’ve got to find out how they’re using it, and what they want, and feature requests, and so on and so forth, come through that route.

And so we, that’s what we were doing. And so any customers who came in who were enthusiastic about When Is Good were talking to us about this need that they could see for a booking side of it. So we were still in the mindset of needing, wanting to, you know, make our millions, and how were we going to create something which we’re going to get revenue from, and proper revenue?

And the thing is that as soon as we built You Can Book Me, there was two major differences to When Is Good. The first was businesses were using it, not leisure, social and leisure people. And secondly, they paid us almost immediately, you know, without question. The pain that scheduling . . . you talked about it at the very beginning, the kind of back and forth email, trying to find a time to meet one person, especially if you’re a business, is incredibly important, you know, to solve. That’s an important pain for somebody to solve.

And so we had, at the very beginning, you know, nail instructors, sort of nail technicians, and driving instructors, and massage therapists, and people who realized that if they could give their customers a way to book them online whilst they were working, they could make more money themselves. So they were willing to instantly pay for it, you know?

And we could just see, it was really . . . honestly, Andrew, it was just, the doors opened. We just realized, this is the tool. This is what’s going to work. Because people are flocking to paying for this. Whereas When Is Good . . .

Andrew: Why did you turn it into its own site instead of adding it to your existing business?

Bridget: Because, well, I mean, it’s essentially . . . I mean, we built it from scratch, so we didn’t . . . the only thing, really, it shares in common with When Is Good is it has the same very familiar grid. So the experience of the booker, if you like, is very similar, that they get this standard grid.

But the difference with You Can Book Me is that it bolts onto calendars. So we now integrate with Google Calendar, with iCloud Calendar, and then with the suite of [inaudible 00:28:05] calendars, like AOL and Yahoo. So we had to build the calendaring integration first, and then build the app.

So, yeah, I mean, we . . . it wasn’t really well thought through. We just thought we were going to launch a new product. I mean, to be honest, remember we already, this was, like, our seventh or eighth product that we’d written, so we’re not shy about buying a domain name and, you know, giving it a go.

So as I said, it was . . . and of course, we had by that point over 100,000 people on When Is Good, so we had an easy market for us to market You Can Book Me to.

Andrew: So you told our producer that the first version was really simple. All it did was let people book on their Google Calendar. I’m now looking at a version of the first . . . actually, I’m looking at the first version right here. The first version of the home page has a two-minute video explaining what the software does, and a one-sentence description. It lets you, it lets people book fixed length slots straight into your Google Calendar.

And the other thing, and so there’s a live demo, or they could just start signing up. The other thing that’s interesting is, in addition to the standard, you have three links, home, register, login, and feedback. It’s the feedback link that’s so interesting. You really made it prominent. It’s one of the few things that you had on there. And you asked people for specific feedback, and you gave them examples of the kind of feedback you wanted. Should people be allowed to book multiple slots in one go? Do you want to include payment options? Like, you gave them samples of the things that you were looking for so that they would give you feedback.

Bridget: Yeah. And then later on, we built a tool which we called Feedback Frenzy, which allowed people to rate and vote on the feature requests that were coming in thick and fast. And it was a very nascent customer service type software, you know, so you could answer their questions through the app.

So, no, absolutely. I mean, we’ve unashamedly built the tool entirely on the basis of the feedback in discussions with users. And, I mean, that was, I have to say, that wasn’t me in the early years. That was Keith. And that was sort of, you know, Keith, in a very efficient way, only adding features that he knew people needed. And these weren’t just random free users kind of giving us feedback. These were businesses who were selling their own products and services, whose, you know, who understood the bottom line, and who knew what that booking service needed to do for them.

Andrew: And what was . . . I’m now riveted by the . . . you know, it’s just someone using it. It’s Keith using it. I can tell it’s Keith because his URL is in the screencast.

Bridget: Okay.

Andrew: Showing how the software works. What’s the biggest piece of feedback that you got when you launched this simple version?

Bridget: Oh my goodness, I haven’t been a . . . I have no idea. What was the biggest . . .

Andrew: Was there one thing that shocked you or stood out as real users started getting into it?

Bridget: No. I mean, the thing that was overwhelming was enthusiasm. As I said, I mean, I think that in that early first year, we grew around 2000%. I mean, it was crazy. The take-up was so fast. And I think that probably, had it been our first product, we probably wouldn’t have really . . . we probably would have just taken it for granted. But the fact that this was our third major product that we had tried to launch, we understood immediately what we had.

I mean, so that was in 2011, was the first prototype. So, you know, we grew over 2000%. The enthusiasm and the feedback was really extensive. And, you know, we knew that we had something, and it was . . . I can’t remember. I mean, the actual iterations of the tool itself happened very fast. Like, I mean, you know, Keith would add features. Users couldn’t believe it. They would email him, and they’d say, “It really needs to do such and such.” And he’d think about it, and almost, you know, as soon as he’d finished reading the email, he’d written the feature and added it in.

And sadly we don’t, we haven’t got that fast turnaround now, unfortunately. So anybody watching this who’s a fan of You Can Book Me is going to be asking why don’t we do that now. But, you know, we’ve learned a lot since then about . . . and almost we’re solving different problems now to what we were solving then as a product. But . . .

Andrew: Bridget, what’s the deal with the low, low, low, low pricing in the first days. Like, I’m looking at your software in the early days. This is . . .

Bridget: It was, like, £4 a year or something. It’s crazy.

Andrew: Yeah. It’s £10 a year.

Bridget: What site are you on? Are you on that kind of recovery site at the internet?

Andrew: I do a couple of things. I get snapshots using Google caches, and I use

Bridget: Okay.

Andrew: I also use Similar Web. I had the pro account for a long time, and then it went away, like, two weeks ago. And then I realized how important Similar Web is for me, that I can actually see where your traffic’s coming from, what your ads look like, if you bought ads. Let me see. Anyway, so I’m hunting through a bunch of different things at the same time.

Bridget: Okay. It’s like you’re looking [inaudible 00:33:02] . . .

Andrew: But the thing that stood out for me as I went through your site is the low price. Ten . . . where did you come up with the price?

Bridget: Right. So, I mean, it . . . this is something which I really wanted to talk about with you and your listeners. Because if you’ve got people watching who want to, you know, do the kind of thing that we’ve done, clearly part of it is don’t do the same things that we did, which we wouldn’t recommend. Now, I think that one of the things that is very common, because I read about it, particularly on bootstrap companies, is that we generally price low, and we generally underprice.

And I think it’s because revenue is so precious, we’re kind of neurotic that, you know, we don’t want to price too much, and then people won’t use it. So I think that when we priced that first year that price, it’s because we were so grateful for people coming through the door and paying. And really, what you’re trying to establish is the product market fit and, you know, all of the other stuff.

And so what you don’t want to do is scare people off by looking expensive, because what happens if you charge too much, and then they come and they say, “But you don’t do teams, or you don’t do services, or you don’t take payments,” or blah blah blah, and then you feel like you’re ripping them off by charging too much.

And I think that in a way, you need more business confidence about what you’re offering. And I, you know, had we . . . going back and doing it again, we should have charged more. We should have just charged . . . you know, I still think there’s a lot that we can do to our pricing to improve it. So I felt . . .

Andrew: How do you know what to charge?

Bridget: How do you know?

Andrew: How do you figure out, when you’re starting out, what to charge for something like this?

Bridget: Well, I mean, so part of it is driven by the market. So part of it’s looking at your competitors to see what kind of equivalent products are they selling at. And, you know, you make a decision, and there’s plenty of philosophy around pricing, that sometimes you want to be the most expensive, because then people think you’re the best. You don’t want to be the cheapest, because then people think that you’re not, you know, you’re the worst. So you want to price it competitively.

There is a problem, as it happens, in scheduling tools, because they’re so different. There’s a massive variety. It’s very hard to compare . . .

Andrew: And as one person said on that LifeHacker article, it’s already built into Outlook. Why would anyone want to use it?

Bridget: Right.

Andrew: Right? And so it’s hard to take that into account.

Bridget: Yeah. Exactly.

Andrew: Gina Trappani jumped back into the comments and said, “Yes, it’s available in Outlook, but it wasn’t available cross-platform in Outlook.”

Bridget: Exactly.

Andrew: You know, which I had no idea that that was even a part of Outlook. So I could see how there’s everything from free to really expensive tools. So is there a technique that you would recommend that entrepreneurs use to figure out what the right pricing is when they’re starting out?

Bridget: The really core question you’ve got to ask is how much value are you offering users? And make sure that you are pricing on the basis of some kind of . . . well, two things. Value, you know, the value to the customer . . . well, I . . . sorry, three things. Value to the customer has to be central. You have to make sure that people are . . . that the features that you are saying you have to pay for are the features that you think are going to offer the most value. People can do without them, perhaps, on a free version.

But if you’re a business, you know, there are certain things you’d going to absolutely want, and, you know, you make sure that you’ve priced that into . . . you know, accordingly. So I think that understanding the pain that you are solving, and understanding the value you are offering, and make sure that that price is pitched at it.

But I also think — and this is very hard — is to try to find a pricing model which is suitably scaled according to the size of your company. So if you have a large company using you, you should be able to find a mechanism to be able to charge them more. Now, I’m not saying for a second we’ve got this right, and we’re actually sort of, at the moment, reviewing the way we do it, because I don’t think that freemium, you know, premium professional type plans often do get that right, and I think it’s very hard.

But then thirdly, and this is a classic, and if you’re interested, I mean, we changed our pricing earlier on this year partly because of this reason. If you’re offering a free tool, make sure that you don’t offer in the free version features which are expensive to support. Because by definition, you are then cost, it’s costing you to support the most complicated features.

And so one of the things that we did earlier on this year was we took all of those features away from the free tool.

Andrew: What’s a feature that costs you a lot to support?

Bridget: Oh, on duty, by a huge margin. It’s a brilliant feature. I mean, I’m not trying to sell you . . .

Andrew: What’s on duty?

Bridget: . . . completely, but it is a fabulous little feature. It’s, so as you were saying at the beginning, You Can Book Me plugs into somebody’s Google Calendar, and so it takes all your free time for your calendar and it displays it in a grid. Perfect. But what happens if you only have certain slots in the week that you want to make available? So in your case, you’ve maybe got five slots during the week that you want to do interviews that you want people to book in for. So you don’t want the whole of your calendar to be free.

So on duty allows you to select those slots in your Google Calendar direct, so you specify them with an event, and then you link that event back to You Can Book Me, so You Can Book Me only shows those times.

Andrew: Oh, so I can just, in my calendar, add the times that I’m available.

Bridget: Precisely. And . . .

Andrew: I see. As opposed to on your site. So, you know what? I want to underscore the other thing that you said. You said look for features . . . charge bigger companies more . . .

Bridget: Yeah.

Andrew: . . . and look for features that the bigger companies need, and include that in the more expensive bucket.

Bridget: Well . . .

Andrew: So it’s not just based on what’s more expensive for you to support, though that’s clearly an important thing for you. But it’s also saying, we know that bigger companies can afford more, and will feel more comfortable, even, paying more. What are the features that only big companies need? Let’s put those in the more expensive package, and you call that the business package.

Bridget: Yeah, sort of. I mean, we don’t get it right. So, for example, we have services and teams, and you can have a massage therapist . . . or, no, not massage. A beauty therapist who might have loads of services, like 30 or 40 services, because she’s offering all manner of different types of nail conditioning.

Andrew: Yeah.

Bridget: You know, whatever. But she’s only one person. She’s only one contractor. But she needs, she might need the business account, because she’s got 30 services. Whereas you can have another big company that needs 30 team members, and they need 30 calendars. So we are, at the moment, reviewing how we do it, because we haven’t got it right.

Andrew: How do you review that?

Bridget: Well, it’s really hard, because pricing is something that I know some companies like Buffer have blogged about how they launched different pricing models, and it hurts. And one of the questions, one of the things that we do is, well, first of all, it’s very hard to AB test pricing changes. It’s very hard to sort of try to kind of suck it and see before you do it. So in a way, you have to just jump in, and whatever decision that you think is right based on the evidence. So based on the pain that you’re suffering, or in my case, earlier on in the year, the fact that we weren’t making enough money, which was a problem. We weren’t profitable.

So you start to look for the reasons why it’s not profitable, and make the changes. The things that then make it easier to implement in a tool where you’ve already got a mature user base and a mature revenue stream is you grandfather. So I believe that, really, a deal’s a deal, and if somebody signs up on a particular price mechanism and price deal, you say to them, “Absolutely. We’ll continue to support it.” That’s not to say that we wouldn’t then introduce a different model for new sign-ups, for example. So new sign-ups might not get the same deal that somebody who signed up in 2012 would get. So . . .

Andrew: But do you call up big businesses and see what are the features that they need? Do you call up smaller companies and see what features they are using? Do you do anything like that?

Bridget: No. I mean, most of the time it’s all inbound. So it’s what people . . . I mean, we will only really look at changing features in You Can Book Me if it’s part of our existing plan. We wouldn’t add in a custom feature for somebody just because they wanted it now. Not at all. I mean, that . . .

Andrew: I see. But, for example, I see that one of the features in the business plan, which is the most expensive plan, is manage 30 separate You Can Book Me accounts via one dashboard. I guess that’s kind of intuitive that a bigger business would need that. But combining iCloud and Google Calendars is available in the more expensive two plans. How would you know that that’s something you should include there, and that maybe an individual wouldn’t need that?

Bridget: Well, it’s . . . it’s somewhat . . . I mean, an individual could need it. An individual could need, you know, they’ve got an iCloud calendar that they use, and they’ve also got a Google Calendar that they use. There’s no reason why not.

I suppose the question is more, what could lower paying people do without? So essentially, if you’re trying to use You Can Book Me for a simple service, you’re not charging money for it, you can do with just a Google Calendar.

Andrew: I see.

Bridget: So, I mean, remember the vast majority of people who use You Can Book Me don’t pay us anything.

Andrew: Okay.

Bridget: So we know that, in fact, people want a decent, you know, accurate, and reliable booking service which is going to book into, you know, their resources into a Google calendar. And, you know, we are trying to find the sweet spot of providing an excellent service, but being able to pay for it.

So as I said before, you know, earlier on in this year, we took a lot of features away from the free tool because it was incredibly expensive to support and we weren’t making enough money. It’s as simple as that. So we put those features into the premium tier, and then we moved some of the things from the premium tier into the professional tier, and the result was we made more money. You know, more people upgraded.

So you can, you start to learn more about the psychology of what people want when you start making changes. And I think, again, some of the advice that I had read on previously, you know, in blogs and so on, is that people don’t experiment with pricing enough, because they’re too afraid. And I think that it’s true that if you are revenue-funded, as we are, we don’t want to mess with our revenue. We don’t want to mess with our loyal customers. We care about them, and we don’t want to, you know, just experiment for the sake of it.

But on the other hand, we’re also trying to run a business, and we’re trying to find an optimal level that makes us profitable, enjoy the job, and also provide a high-quality product. And that can sometimes be hard when you’re . . . and there’s plenty of people who come to us to say, “Look, I am only . . . you know, I don’t need your $48 plan. I just need this one feature. You should put it in the $16 plan.”

And, you know, the response has to be, “We’re really sorry that that is arbitrary.” Some of it is arbitrary. You can’t justify it. I think that you can do a certain amount of intuition of what you think is going to add value. And as I said, we’re right now reviewing what we’re doing, and we’re reviewing the way we price it, because we’re still not happy with the way we’ve done it.

Andrew: Do you know what? You were talking about experimenting with pricing, and you were talking about Buffer, and how they said they were experimenting. Buffer actually shows not just their overall revenue in real-time, but they show how many members are part a part of each of their . . . I don’t know how many. Dozens of different pricing plans.

Bridget: Oh my gosh, really.

Andrew: You really see all their experimentations. Like, they have something called . . .

Bridget: Yeah.

Andrew: Where is that? Enterprise 30, which only has three members in it. They have something they experimented with called Enterprise 1. They have zero members. That must have failed. They have something called the Pro Plan. That has 18,787 members. That’s doing well.

Bridget: Yeah.

Andrew: Anyway, you can see all that if you just go to, and you can see their data in real-time.

Bridget: Oh, that’s cool. [inaudible 00:44:27]

Andrew: Shocking. But they definitely experiment, like you said.

Bridget: Yeah.

Andrew: All right, since we’re taking a moment away from your business, from You Can Book Me, and talking about other sites, I’ve got to tell everyone who’s listening to me about a company called TopTal. Top as in top of the mountain, Tal as in talent, is the sponsor.

I used them recently. Here’s what happened. Our search sucked at Mixergy. And frankly, people kept telling me, “Search stinks. I am trying to find one interview about how to create a sales funnel. How do I find that?” Or, “I’m trying to find all the interviews that you have about how to get traffic. How do I get that?” We knew it stunk.

And so we went to TopTal and we said, “We don’t have the resources, we don’t have the people to do this right now. Everyone’s working on other projects. Can we just hire one of your people to take on this issue for us?”

And at first I didn’t think we could even go to TopTal, because we’re a WordPress-based site. I thought that they only worked with people who use more advanced software than us. But they have people for WordPress, too. And so they introduced us to a guy, and our head developer said, “He’s not the right fit.” I forget why. But in fact, I never even took the time to understand why. If it wasn’t the right fit for Michael, it’s not the right fit for us.

They introduced us to another person who understood our issues, who understood the way we worked, and he was good, and we started working with that guy. And we thought this was going to be a long project, but instead the guy turned it around in under a week. And what he did was, he gave a search that just worked super fast, and a way of organizing all of our interviews that was just really clear.

And it’s just worked so well that we, frankly, we thought we were going to have a long-term engagement with this guy, but that was it. We had just a few days. He created the software. Everything was good. We were going to launch it. But we said, “Our design around it just is so whacked out that it just looks ugly. It makes no sense. People won’t even know how to use this guy’s great software. We’ll have to . . . ”

If we coach them, they’ll get it, because he created something that works. But if they have to look at our crappy design, they’re never going to get it. And so we decided we had to reskin the whole site just based on the fact that we now have good search. And so that’s what we did, and now we have a brand new site that looks good, that you can see how well the search works, that you can actually find things based on tags and based on likes, and so on.

And the whole thing happened because we had a developer that was just so good, and we found that developer through TopTal. If you need a developer, all you have to do is go to If you go to and you add a /Mixergy at the end, so

In addition to their no-risk trial period of up to two weeks, which means that if you’re not happy, you get . . . they won’t bill you. I was going to say you don’t get your money back. But they’re not going to bill you, and they will still pay the developer.

But in addition to that, if you go to, they’ll give you 80 free TopTal developer hours when you pay for 80. We paid . . . I wish I had this link when we started so that we could have gotten an extra 80 free hours.

So we had a good developer who stretched the way that we were thinking about business, who forced us to get better with the rest of our business, and created a search that was way better than we ever had before. That’s why we use TopTal. That’s one of the reasons why companies like Air BnB, Ideo, and ZenDesk use TopTal.

If you need a developer, go to, or frankly, just email me. I’ve introduced so many people to my guy over at TopTal. I’d be happy to introduce anyone who’s listening to me right now. Just email me. My email address is Super simple. And I’d be happy to introduce you to my guy over at TopTal. I just got a thank you note from him yesterday saying, “Andrew, thanks for making all these great introductions.” So apparently it’s working. He’s happy with it. I’ll be happy to introduce you to TopTal. I’m grateful to them for sponsoring.

So, Bridget, now we have software. We understood a little bit about pricing, how in the beginning you didn’t price right, but later on you developed better pricing. We understand the way you think about it. But what I’d like to know is where you got your first users.

Bridget: Oh, well, When Is Good. I mean, you know, so it was a pure, organic migration from When Is Good to You Can Book Me. And then exactly the same viral magic happened, which is it, when people started . . .

So one of the things that we did to help grow the You Can Book Me tool was we gave it away for free to schools and universities. So we’ve always, always, from the very beginning, even when we weren’t making any money on it at all, have given the software away for free. Of course, it was already in America because of When Is Good and LifeHacker and MIT, and so on.

And I think that there’s this sort of a, you know, there’s really . . . it’s when you’re . . . when you don’t realize it, but you’re riding the wave. And at the time, we were riding the wave of universities and schools adopting Google apps for education. So they had access to all of these amazing free tools in their own, you know, institutions, and they were looking for tools to plug into those resources, such as calendars.

And so what You Can Book Me was very different to its competitors at the time was that it wasn’t a calendar app. We didn’t build a resource application. We just built the booking platform that sat on top of Google Calendar. So it very quickly took off in school districts. I think You Can Book Me is now being used in more than half of the school districts in America. In North . . .

Andrew: Wow. You know, that explains it. So I told you I use Similar Web to hunt through people’s traffic and understand where they’re getting their traffic. I see sending you traffic, byu, Brigham Young University, .edu sending you traffic.

Bridget: Right.

Andrew: I see I see .edu throughout your referral logs. These people aren’t paying?

Bridget: Oh, some of them do, yeah. I mean, you were saying before about the linked accounts. So a university department might upgrade to business so that they have one billing . . . so Princeton . . . not Princeton. Stanford. Get those two mixed up. Stanford have a business account so that they have all of their counseling and advisory staff, all their own You Can Book Me accounts.

So what tends to happen with universities is that the individual professors will have You Can Book Me accounts, and they’ll have the free version, and they’ll be using it to organize seminars with students, for example. But if the university sort of departmentally wants an account, then they’ll usually pay.

Andrew: I see.

Bridget: So schools, just to give you an example of the kind of viral loop, in North America, in Canada, we have a lot of users. Again, you know, partly because whoever was the first Canadian user introduced us, I guess. But Edmonton Public School District, over the history of using You Can Book Me — and they’ve used us for, almost since our launch — they’ve processed over 45,000 bookings in Edmonton.

Andrew: Wow.

Bridget: Through, what they’ve been doing is parent/teacher conferences. So we used to add, and we still do, a “Powered for Free” button at the bottom of the grid. So the schools would use our grids, the parents would click away, book our parent/teacher conference. And now in Edmonton we have a papal center, we have a dog grooming center, we have a cleaning firm who use us. So there’s all of these small businesses in Edmonton who use us because they were exposed to us from the school district.

So it’s a very symbiotic relationship between the education sector that essentially adopted Google apps tools, pushed out the solution, people who would never have considered using an online booking service were introduced to it by their parent/teacher conference experience, and then they started to use it.

And we are incredibly grateful, you know? And to the sector, and we still continue to give our software away for free to all of them. Because, yeah, there isn’t a university in America that won’t be using When Is Good or You Can Book Me.

Andrew: What’s different about the way that they get it free and the way that anyone listening to us can get it for free? Are they just using the standard free account?

Bridget: So they’re using a standard free account, and we give them certain features on top of that. So we give them teams, which is multiple calendars, and then there are certain other features which we had taken away from the free version in March, but we still leave them for the education, which is . . .

Andrew: How can you tell? You watch their .edu URL? [inaudible 00:52:21]

Bridget: Yeah. So if you set up a You Can Book Me account with .edu, then . . . and for the . . . Canadians hate this, because we haven’t done it for the Canadians, but we should, for the Canadian universities. But they, yeah, if you have a .edu account, then you automatically get access to a suite of extra features that we know are used in that sector.

Andrew: I see. I see. Okay. You know what? I’ve noticed this a lot with software, that if you have software that faces the public, not just the user themselves. So CRM wouldn’t be a good example of this. But email collection software, for example. If you’re running a business where your software allows your customers to collect email addresses, your software’s interacting with way more users than your actual user, right?

Bridget: Yeah.

Andrew: Than your customer. Well, what I’ve noticed is that if you have a free version of that, and you say “Powered By” in that, you get tons of free ads. And so a good example of that is Hello Bar that for a long time got a lot of traffic from it. Sumo Me, I think, is what . . .

Bridget: Yeah.

Andrew: . . . [inaudible 00:53:19] thing is called. Allows people to collect email addresses. And the free version, he has a crown. Or, no, it’s king? Is it Sumo King? What is it called? Sumo King?

Anyway, you get it. It’s really a very powerful way of getting new users. I wish we could do that for podcasts, but it’s not public-facing. Our end users only interacted with it on their own.

Bridget: I guess this is it. I mean, this is what the techniques that, you know, famously companies like DropBox have done very well, which is how do you encourage people to spread the word about your product naturally, like introducing friends and credits and so on?

We, just to give another credit to, you know, early inspirers. I was telling you at the beginning of this interview that one of my favorite companies is Weebly, and I was a very early adopter of Weebly’s tools. And their model of having a “Powered for Free by Weebly” button at the bottom of your free website builder was essentially what we copied.

So when we set up the You Can Book Me grids, I said we should have a “Powered for Free by You Can Book Me.” It’s got to be prominent. It’s at the bottom. And then obviously the businesses come along, and the businesses say, “I don’t want that Powered for Free button, because I’m a business.”

Andrew: Right.

Bridget: I want to . . . I don’t want them to think I’m a cheapskate. So they paid to get rid of the Powered for Free button.

And I think that, again, we have an honest relationship with our users. So if you pay us, you can have an almost brand-free experience using You Can Book Me. The CSS is there. You can have it very customizable. So, because I think there are some companies that have it on everything, so you basically can’t get away from their brand. Whereas You Can Book Me, if you pay us, yeah, you, sure, you can go ahead, and nobody will know you’re using You Can Book Me. But if you . . .

Andrew: It’ll just seem like you built your own software.

Bridget: Right. But if it’s free, we’re in there, you know? We’re all over the place. Because we haven’t, Andrew, in three years, we haven’t spent any money on sales and marketing. We have just grown virally because of this loop, because of this introduction to people booking through the service. And we’re delighted that a couple of weeks ago, we hit our 10 millionth booking. So we had prizes . . .

Andrew: Ten million.

Bridget: Ten million bookings.

Andrew: What’s your revenue now?

Bridget: So at this very moment, so, like, November/December, we have just hit our $1 million ARR.

Andrew: So 2015, you did $1 million.

Bridget: No, no, no. Our monthly ARR is now consistent with $1 million.

Andrew: Ah. You’re saying you take your monthly recurring revenue, multiple it by 12, and you end up with $1 million. And you also have an annual plan, don’t you?

Bridget: Yeah, people get . . . so people . . . yeah, yeah, yeah. But, so, I mean, what I’m talking about is actual income. So in our profit and loss, our actual income, so . . .

Andrew: So it’s not the monthly recurring revenue. You’re saying that you’re at a run rate of $1 million, which means if we take last month’s revenue, multiply it by 12, you do $1 million.

Bridget: Yes. Precisely.

Andrew: You finally hit that number.

Bridget: Right. And we get more. We actually earn more. But that’s not the same as our cash flow. So our cash flow is always more, because we always get more in from people paying in advance.

Andrew: Right.

Bridget: And that is the other critical thing. You were talking about revenue and profits. The critical thing that we did at the beginning, and it was completely inadvertent, but I realize it made a massive difference, is we checked out, we used PayPal for checking out at the very beginning. PayPal doesn’t do monthly billing. So, and because we were charging so little, we made the minimum upfront payment six months. So if you wanted to upgrade on You Can Book Me two or three years ago, you would need to buy six months. It was only, like, $45. It wasn’t a huge amount.

So what we didn’t realize at the time, but I would recommend this to anybody, is get your cash upfront. So we were getting six months’ worth of income all upfront in the first month, which made a massive difference to our cash flow. And we didn’t switch to monthly billing until December of 2013. So it was only two years ago we switched to monthly billing. Which was quite frightening, because then, of course, when we were getting six months upfront, we were suddenly getting, 90% of our revenue was coming in in one month. Which was kind of nice, because it means that you haven’t got the liability of that cash in advance.

So, but on the other hand, it was kind of, it was more sensible, especially in a way that, you know, you want to run your income versus your cash.

Andrew: Did it increase your revenues to allow a monthly option?

Bridget: I guess . . .

Andrew: Or did it increase your sales, I should say.

Bridget: Yeah, yeah, yeah. Did more people . . . yes, I think it did. I think more . . .

Andrew: So you got more customers, but then you have to worry about more churn.

Bridget: Yeah. More people were willing to upgrade for one month to use the software and see how it was, rather than upgrade for six months. But as I said, I wouldn’t change that, because in that first year, to have everybody paying you six months or 12 months in advance was a great way to get cash upfront.

Andrew: And still there were some challenges. One of the challenges was that you had this big event in your city. What town is this that you’re in?

Bridget: Bedford. We’re north of London, a town called Bedford.

Andrew: And in Bedford, Google came, Apple came, other big guys came, and now you’re smiling, but at the time you were not smiling.

Bridget: It was awful.

Andrew: Because what happened?

Bridget: Oh, we had it . . . it was . . . so we were hosting a . . . so if people haven’t realized, we’re a very small company. There’s only, you know, there’s only 12 of us. At the time, then there was only about eight of us. And we’re bootstrapped. And so we keep ourselves to ourselves in little blighty.

But we are members of an international consortium called CalConnect, which does calendaring. So as I said before, we interact with Google Calendar, Apple Calendars. And the big boys need to meet up three times a year to figure out international standards around calendaring, which actually turns out to be very hard, because you’ve got time zones and all sorts of other things that need to be compatible. So anything to do with calendaring.

And we are . . . we support the event. And every year they try and have a meet-up in Europe. So we basically got sort of hard-shouldered into hosting the event. So they all came last year. We were very excited about it. And we booked a big room in the local museum for them to meet up. There’s a whole load of developers, and they meet up, and they do interoperable testing about, against Apple and AOL and Yahoo’s servers.

So, yeah, they were all there, and it happened to be the same week that we had tried to migrate off Google Calendar API 2 . . . this is quite technical, sorry. Onto API 3. So we had to do it. Google had been telling us for months and months and months, “You’ve got to do it. You’ve got to move off API 2.” So that’s what we were doing.

And it was a classic case of, you know, a rock and a hard place. You either throw everything over and do the migration quickly, because you’ve got to do it, because you’re trying to meet a deadline, or you try to do it more slowly, and you test, and you miss the deadline. And then, you know, one way or another, users fall out.

And in this case, we did the migration during this week very quickly. We threw a whole load of new code at new, at paying customers, and it melted down. The whole thing melted down. And this is the worst thing about the time zone differential, because the majority of the people who use You Can Book Me are in North America, and we’re obviously in Britain, is that if you go to sleep at 11:00, and your servers go down, you don’t know about it until eight hours later.

So that’s what happened. And we woke up on one of the mornings of that conference, and our product had, our service had gone down, and it had gone down badly, and it was . . . and we let down a lot of users, and a lot of people who were annoyed, and we had a lot of humble pie to eat, and we, you know, emailed a lot of people, and we gave away free upgrades.

And meantime, Keith was having to go to this conference with all of these amazing developers sitting around, you know, whilst we’re hosting the event and putting on . . . it sounds really stupid, you know, as our service was under a lot of pressure, we were also, like, doing drinks receptions for them, and going out, and, you know, really not feeling like partying at the time.

When, you know, it is unmitigatedly the most painful experience when you know you have let your users down. And I don’t say that as a cliché or for spin. But when you have people whose businesses are relying on your service, and you know you’ve caused them pain, you know you annoyed them, that they relied on you, they trusted you, and then your service wasn’t there for them, it is horrible. It is horrible. It’s like watching your own child fall over, you know? You just want to, anything you can do to avoid letting them down.

And so we had a really tough week, because it was supposed to be a week of triumph of You Can Book Me.

Andrew: Yeah. Yeah. You’re hosting the event.

Bridget: You know, [inaudible 01:02:00]. And we were really . . . poor Keith was really struggling that week.

Andrew: What do you do to keep that kind of thing from happening again?

Bridget: So, well, follow our own rules. So we had rules about the way you migrate new code, and one of it was don’t . . . you know, test it properly. So a proper testing regime. So I think it was one of the examples of when we emerged as a company out of the very early hustle, you know, when you’re hustling, and you let a lot of things slide, and you don’t think things matter, and then you realize there’s reasons why people have testing regimes, and there’s reasons why people have proper development cycles, and they, you know, nothing ever gets onto production until it’s been properly tested. And I think that the days of us being able to chuck code onto the servers and let them run and see what happens are just over.

And so I think much more robust procedures and understanding that it matters, and there’s a reason, is one of the things that we did. We also . . . you know, I mean, this is . . . I don’t know if this is interesting for anybody, but we are . . . we have migrated and re-engineered an awful lot of the way we now deliver our service to make it more robust. So we’re moving our hosting providers. We’re changing our architecture.

You know, we’re just doing an awful lot, because we . . . because, as I said before, the problem we’re solving right now in You Can Book Me is not a problem of creating a good booking tool, much as we’d like to. The problem we’re solving is how do you scale the engineering of this company? Because we are growing, you know, at a ferocious rate, and so every time somebody signs up new to You Can Book Me, we have to make sure that we’re delivering a fast service for them.

Andrew: Another issue is something that I had Matt Gallaghan, the founder of Circa and the nonprofit 1% of Nothing, and a couple of other things. He was over at my house last night for scotch. We were talking about how, now that I’m a dad, a lot of my mind goes to thinking about my kid, but not all of it. I’m still here, and not thinking about having my son. Just the balance and the lack of balance is, it’s a big question about whether we’re as sharp now because . . . whether I’m as sharp now because I have a kid, and whether he should even get in a relationship, because it does suck away time from work and creativity.

Bridget: How much scotch had you drunk by this point?

Andrew: It doesn’t take much for me to get into this stuff. So, like, maybe one, one little glass?

Bridget: A dram.

Andrew: And . . . like, yeah, an ounce. I’m now watching how much I take, and how much I eat. I use an app to keep track of it. How much I drink. And I know how many calories are in an ounce of whiskey. It’s about 75, depending on which one I have. And so I feel like, okay, I’ll have them by the ounce now.

Bridget: [inaudible 01:04:40]

Andrew: Sorry?

Bridget: Don’t . . . if anybody in Scotland ever knew the number of calories in a dram of whiskey, that would be the end of them.

Andrew: You know what? I thought there was none in it, because it just seems so simple. It’s just a little, like, an ounce is nothing. I thought . . . I get beer. Beer is very filling, and it’s a lot like drinking bread. I get it. Those guys who drink beer, of course they’re going to put on a lot of weight. But I’m a runner, and I only drink scotch. It’s not that big a deal. Or different kinds of whiskey.

So anyway, now I’ve been aware that there are some calories in that, so I watch it. But I wasn’t last night, and we were talking about that, and I was thinking that, like, how much am I sacrificing? How much am I willing to sacrifice? I know it’s something you’ve given some thought to. I think you mentioned it to one of our producers. What are your thoughts on this?

Bridget: So I think that this is the advice that people say all the time, and if you don’t pay attention to it, you’re making a mistake, which is it takes a long time to be successful. So I said earlier that, you know, we were looking for the . . . we used to call it the one chess piece move, that we would just do the one web application that would take off.

Andrew: Yeah.

Bridget: It would only take a year or so. It’d be fun, you know? We’d turn it out in a couple of months, and it would be done. And that was, you know, that was 12 years ago. So when we’re bootstrapped, so we’re even slower than normal. Like, you know, if we take on investment a couple of years ago, I guess we could have accelerated.

And so the thing is that it does take a long time, and so really, the whole point, as far as I can see now of doing You Can Book Me is the journey. And, you know, whatever destination we get to, whatever lifestyle, you know, we have as a result of running a company, and that we . . . you know, it isn’t about the end goal.

Andrew: Do you feel like it takes away time from your kids, from your . . . you have kids, two of them, right?

Bridget: Well, no, because . . . the reason why is because the journey is what we’re doing. And so as a result, I make a conscious effort to not say . . . basically, the mistake you can make is, “I’ll miss this birthday party, because we just have to work really hard, because as soon as we’ve got this company up and running and it’s successful, we can then start going to birthday parties.”

Andrew: I see.

Bridget: So in the . . . so for the story I’ve been telling you ever since, you know, Price Per Square Foot, that’s when we were looking for our first house to buy together. You know, in the meantime, me and Keith, we got married, we have two children, I’ve had 25 different jobs in politics. We’ve been to Southeast Asia. We’ve been to Malawi in Africa. We’ve taken our kids all over the world. You know, we’ve done birthday parties. We’ve done bike rides. We’ve done holidays. And we have done . . . and we’ve changed a lot about the way we live our life because we have You Can Book Me.

But in fact, in some ways, the fact that I gave up my job . . . so I had a job in politics, and I gave it up in 2012 to run the company, was the moment when I realized that You Can Book Me needed leadership. It needed strategic management. It couldn’t just carry on the way it was going. And me and Keith made a conscious decision for us as a family to basically run You Can Book Me.

And we did it partly because it means that we do get to have tea with our kids every day, and we do get to, you know, make choices about . . .

Andrew: You have tea with your kids every day?

Bridget: Yeah, we have tea with our kids every day. We only . . .

Andrew: How does this work? Like, in the middle of the day, you guys stop everything and have tea? I’m not, I’ve never . . .

Bridget: No, when I say “tea,” I mean dinner. Supper. Whatever.

Andrew: Oh, I see. Okay. So you have dinner with your kids. I get that.

Bridget: There is . . . yeah. So, but my point is that that work/life balance . . . you know, so I feel guilty, of course I do, when one of us has to come into the office to work on a Sunday morning. Or, as it was happened, we were on our amazing Southeast Asian trip. It was my 40th birthday. We were on an island in Indonesia, in the Java . . . you know, it was just beautiful. And the service went down, and it was terrible, and Keith had to borrow people’s mobile phones, and he was migrating servers, you know, accounts across servers.

And we were I the middle of the South China Sea, you know? And so sometimes we have to say to our kids, “We have to work.” You Can Book Me is basically more important. You know, the priorities of the business are more important.

Andrew: More important not than the kids, more important than the trip that you’re on at the moment.

Bridget: Right, exactly. I mean, even if it’s on Christmas Day, we are 100 . . . we are as responsible for You Can Book Me as we are for our kids. But on the other hand, You Can Book Me gives us freedom, and it gives us independent income, and we can . . . you know, nobody’s telling us what to do. So we get the best of both worlds, and the only thing that I . . . we have to consciously remember is that we . . . there is no, in 10 years time, we’re going to be fine. Like, you have to enjoy your life, and enjoy the time that you are living today. Because if you’re away . . .

You know, I mean, your friend is just an example. He’s actually thinking about not pursuing a relationship because . . .

Andrew: No, he’s not. He wants to pursue a relationship. I was thinking, I was telling him maybe he should hold off, or not . . . actually, I wasn’t even telling him what to do. I was just saying to myself that I was, that I recognize that I spend less mental time thinking about work because I have kids. I have a kid.

Bridget: Yeah.

Andrew: And I enjoy playing with him so much more, and at the end of the day, what I should be doing is maybe leaving with his mom and play . . . and not playing, but working for the next four hours.

Bridget: Right.

Andrew: And I said, now that I have a kid, and I also learned how to have a social life, like, hanging out with Matt and having a drink is not something I knew how to do 10 years ago. So maybe I’m taking my eye off the ball.

And his feedback was, you know what? He worked tons of hours, and he wasn’t as productive as he seemed . . .

Bridget: Yeah.

Andrew: . . . just because he was sitting at the computer. And it is helpful to take some time away. And it feels like you’re just taking time away and not working, but that’s time that you wouldn’t have really been working anyway. That you would’ve been pretending you were working.

Bridget: Well, we have . . . yeah, yeah, yeah. And I think . . . I mean, I think particularly with children, you know, I would never say to anybody, “It’s okay to miss your child’s upbringing because you’re working.” Because, you know, I mean, it’s a cliché, but they will say, when you’re on your death bed, you never say, “I wish I spent more time at the office.”

Andrew: I get the feeling I think I might. I think I might be the one person who does. I don’t know. I might. Because here’s the other thing I was thinking. I don’t remember what happened to me before I was five years old. My kid’s a year and a half. I play with him so much. We have so much time together. He loves me a lot. Like, he loves playing with me. He’s not going to remember this time.

I feel like . . . here’s what I was saying to Matt. I could have probably gotten away with not spending much time with him until he was five, and then entering his life in a serious way, and, like, spending more time working. But I like doing it too much. It’s very . . . it’s very enjoyable.

Bridget: I think the two things I would say to you . . . because my kids are a bit older. They’re eight and nine. So I’m sort of slightly a bit further down the track. So I can tell you that the two things that really matter, I think, to kids, is one is routine. And so, you know, if you’re, if you get into a routine where you spend your two hours in the morning with him, and playing, and then you go off and work, that’s great. And then it’s actually, it’s the routine and the regularity of what you’re doing, I think, really matters, is really good for kids.

Because kids, I think kids live in micro times of the day. So it’s the morning time, the afternoon time, the lunchtime, the dinnertime, whatever it is. It isn’t the big picture. It isn’t that we’re moving house or whatever. It’s always the small stuff in the day that the kids, they . . . that’s the landscape that they live in.

And I think the second thing about everything is balance. So, I mean, I have two kids. They’re quite close together. But I was never at home exclusively with them. I always worked. Keith always worked. We’ve been extremely lucky that we have taken shared care of our children and of our jobs. So, and we’ve always done it. So I’ve always worked, and I’ve always found work to be a great release and break from . . .

Andrew: Yeah.

Bridget: . . . the micro world of children. But then, at the same time, when you’re, you know, when you especially . . . I mean, I used to work in politics, and there’s so much bullshit in politics, and everybody’s flapping about. And, you know, it’s always this big, epic, problematic stuff, and it’s always supposed to be stressful.

So to kind of take a day off and spend it with my kids, and they’re thinking about, you know, Minecraft, or what they’re going to . . . you know, whether they’re going to go to the park. And, you know, it changes your mental space, and it’s a great break.

So I think it’s finding balance and making sure that you’re in charge of your routine.

Andrew: Yeah. I live by routines, too, and I’m glad that kids do, because it makes my life easier.

This has been great hearing your story. Everyone who’s listening to us who’s curious about what the website looks like, go to youcan . . . there it is, You also own, but is the URL for the business. They can check out everything we’ve been talking about.

The two sponsors that I’ve mentioned in the interview are TopTal. If you need a developer, go to And if you want to grow your mailing list and have an unfair advantage, because frankly, this is something that people haven’t yet abused. You know, everything that has to do with growing the mailing list is used until it gets to a point where people are sick of it and it doesn’t work anymore. If you want to jump on something before people are sicking it, go to Kickoff Labs website. Let me give you the URL. Go to When you do that, they’re going to give you all the features that I mentioned, and I’m grateful to them and to TopTal for sponsoring.

Bridget, thanks for being a part of Mixergy.

Bridget: Thank you, Andrew.

Andrew: Oh, and, you know, we should thank the guy who introduced us. I would never have found you except for . . . where he is? Omar Kahn. Right? Omar Kahn, thank you so much for making this introduction. I really appreciate it when someone in the audience, someone who’s a fan, someone who’s a producer out there, introduces me to a great guest. So Bridget, I’m really grateful to him for introducing me to you. Good to meet you.

Bridget: Thank you, Andrew.

Andrew: Thank you all for being a part of Mixergy. Bye, everyone.

10 thoughts on “How long should you be willing to fail before giving up on a startup? – with Bridget Harris

  1. Mike says:

    Hi Bridget. At one point you talk about removing features from the freemium subscription plan due to cost constraints. I’m wondering if you’ve considered adopting a free trial strategy over freemium. If you were to go down this path, then you could have a 14 day free trial where you show the user ALL features that are available and that way they’ll have a good idea of what the application is capable of. I’m not asserting that this is what your company should do, I’m just interested in hearing what your opinion is on this. Thanks!

  2. This is a great interview and I hope everyone listens to the last 10 mins of it. I think there is a lot of talk about founders “giving their all” to their startup, and if you don’t, it’s frowned upon – specially in the Valley.
    But I agree with Bridget that startups are a marathon and not a sprint, a long journey; so you have to enjoy the journey to make sure you don’t burn out or have regrets in the future.
    Of course Bridget articulates this much better in the last 10mins of the interview – so make sure you don’t miss it!

  3. HI Mike – thanks for this, yes that’s by far a better plan I think- to let people try out all the features upfront. Not doing it at the moment was more a limit in how we first launched the product. We do offer free trials to anyone who requested it, and hope to automate it soon. But more generally we like our free tool because it allows up to grow more quickly as people help us spread the word – we just need to balance that with what it costs us to provide. Here’s what I wrote about it at the time:

  4. Thanks Mohammad I’m glad to hear that struck a chord! It is one of the upsides of course from being revenue-funded as we’re not on a timetable to deliver X Investor returns within a certain period – I know Jason Fried from Basecamp has spoken a lot on this subject to Andrew!

  5. Really enjoyed that interview. Refreshing to hear of someone working outside Silicon Valley and not talking about their Series A and whatnot. A lot of common sense discoveries, which I appreciate. As a consumer of online services and software I’m always curious to learn why or why not companies offer a freemium tier. I definitely enjoy being able to use something to explore the product and how it fits in my workflow, but I also understand the support required and how it can be an economic burden to the company.

    Also Bridget, where is your accent from? I hear what sounds like West Country/Bristol but I’m American and could definitely be wrong. I lived in Surrey and met a great many accents playing rugby over the years.

  6. John Cant says:

    Great interview. Thanks Andrew & Bridget. Many of the things that you spoke about really resonated as we’re trying to build an app around time management that people will pay for. Like we started out as B2C but are trying to re-purpose it for businesses as they’re the group who values their time enough to pay to save it. Thanks again!

  7. HI Prescott – thanks so much for the response and comments! I think it’s a close call whether offering freemium is going to work – Mailchimp is an example that always charged right from the beginning, and only brought in a free tier later. tbh if we’d understood more about what we were embarking on at the time, we may have thought more carefully about charging straightway. But the advantages of giving something away for free is you get a very deep and elastic user-feedback loop which helped a lot with the product’s development. As for my accent I’m actually Scottish (highlands) but have also been in the south of England for a long time :-)

  8. Hi John – thanks for this, yes you are absolutely right – businesses immediately see the value in ‘saving’ time and can put a price on it. social consumers might value something different – like sharing with their discrete network. Good luck!

  9. I guess I have to spend more time in Blighty to get it right!

    Good insight about the free tier. The trouble, I imagine, is that for small or new software companies, they are training the world to expect a free service. I know that in recent months I’ve received several emails from companies saying something to the effect of “thanks for being a free beta tester; here’s our pricing plan.” and I just read it and unsubcribe entirely — it didn’t become an essential part of my operation, let alone something with genuine ROI.

    Onwards and upwards.

  10. janis says:

    thx for the interview.. but to be honest as a software engineer and hearing you go to bed and everything breaks down and the next day you know that it is down. get me off.. use a monitor system like newrelic that send you msg on your phone to get out of bed and fix it…
    British people are equal smart as Dutch people ;)

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