S4E9 – How to Bootstrap a B2B SaaS to $5M and Beyond With Bridget Harris

How to Bootstrap a B2B SaaS to $5M and Beyond

Are you wondering how to bootstrap a B2B SaaS to $5M and Beyond? In this captivating episode of the Grow Your B2B SaaS podcast, host Joran explores the journey of Bridget Harris, co-founder and CEO of You Can Book Me. Managing over 20,000 customers and 1.5 million bookings each month, Bridget reveals key insights on bootstrapping a successful SaaS business, obsessing over customers, and leading a remote team. Learn how Bridget’s strategic decisions and focus on top-notch products propelled You Can Book Me to $5 million in annual revenue. Discover essential frameworks and tips to scale your own B2B SaaS startup, all without external funding. Tune in now for practical advice that could reshape your entrepreneurial path!

Embracing Product-Led Growth

Central to You Can Book Me’s success is a commitment to product excellence. Bridget emphasizes the importance of a robust, user-friendly product that meets customer needs seamlessly. This strategy not only ensures customer satisfaction but also drives organic growth through word-of-mouth referrals.

Nurturing a Supportive Company Culture

Beyond product, Bridget prioritizes a supportive company culture. She advocates for a happy, motivated team as essential for sustained success. Using the Entrepreneurial Operating System (EOS) and team retreats, You Can Book Me fosters unity and purpose among its employees.

Customer-Centric Strategies

Key to You Can Book Me’s strategy is understanding and catering to customer needs. Bridget stresses the significance of aligning offerings with the most valuable user benefits. This approach fosters loyalty and longevity, vital in a competitive market.

Strategic Planning and Execution

The company employs frameworks like Traction for clear goal-setting and progress tracking. This disciplined approach ensures cohesive efforts across the organization, reinforcing the importance of strategic alignment.

Resilience and Adaptability

Bridget’s journey highlights resilience amidst challenges. Her unwavering commitment and adaptability underscore the importance of learning and staying focused on long-term goals.

Bridget Harris’s insights offer a comprehensive blueprint for aspiring entrepreneurs aiming to build not just successful businesses, but also enduring enterprises that prioritize product excellence, customer satisfaction, and team well-being.

Manual on bootstrapping a SaaS: https://youcanbook.me/manual

Key Timecodes

  • The Origins of You Can Book Me (00:52)
  • Business Metrics and Growth (01:30)
  • Product Overview (02:10)
  • Entrepreneurial Journey (03:05)
  • Achieving Success (03:24)
  • Motivations and Goals (04:13)
  • Pivoting to Success (05:53)
  • Bootstrapping Philosophy (07:15)
  • Rock Bottom Moments(09:09)
  • Handling Growth and Change (12:41)
  • Viral Growth and Market Strategy (18:18)
  • Internal Processes and Traction (23:29)
  • Focusing on Customers and Pricing (29:51)
  • Advice for Startups (37:22)
  • Scaling to 10 Million ARR (40:32)


[00:00:00.000] – Bridget

Everybody thought that starting a business was actually about taking money off VCs, and VCs become your customers, and you have to obsess about what VCs think. I think now that since the last couple of years, everything has gone a little bit south for people. Everybody loves thinking of what the domain name is going to be, pootling off to Hover and buying it and little MVP going, everybody talking about it down the pub. Everybody loves that part of it, but it’s the actual grind of a company in a business, not the product, that takes the time and can grind you down if you’re not careful. I want to build a really good company. I want to be able to show and demonstrate it’s possible to build a company that people love to work for, and that we get away from this grim work culture where people feel like it’s all about not working and getting away from work because work burns people out.

[00:00:52.490] – Joran

In today’s episode, my guest is Bridget Harris. Bridget is the co founder of You Can Book Me, a calendar-based scheduling tool with over 20,000 customers and 1.5 million bookings handled every month. Before starting You Can Book Me, she worked as a special adviser for the UK government, as well as other jobs in UK politics. You can see often Bridget on big SaaS conferences like SaaS Talk, SaaS Open, where she speaks about her journey, bootstrapping, building a global team or profit sharing. I’m personally really looking forward to this episode. And a fun fact, we are recording this again, live in Bucharest, Romania, as we’re heading to the TekPon Awards tonight. Welcome to the show, Bridget.

[00:01:30.000] – Bridget

Thank you very much, Joran. Lovely to be here.

[00:01:31.790] – Joran

Cool. We’re going to dive right in to get to know You and You Can Book Me. I’m going to ask a couple of quick questions so people can get a bit more context. When did you start You Can Book Me?

[00:01:43.680] – Bridget

The first version of You Can Book Me, the product, went out in 2011. I took over as, as you said, co founder, but also CEO full-time. I gave up my job in politics in 2012. But actually the story of myself and my co founder, Keith, as technologists and entrepreneurs, that started a long time ago. So the first product that Keith first built was in 2003. Actually, we’ve been doing this for more than 20 years.

[00:02:10.220] – Joran

And you’re really open about it. What is your current ARR right now.

[00:02:15.350] – Bridget

So we’re about $5 million ARR.

[00:02:17.520] – Joran

And is there any separation between service and product revenue or is it purely product?

[00:02:22.990] – Bridget

I would say more than 95 % self-service, product-led growth all the way. We’re the poster child of product-led growth.

[00:02:28.970] – Joran

Yeah. And you work It’s really a global, right? How many global employees do you have?

[00:02:33.740] – Bridget

We are a remote company, and we’re very passionate about employing people remotely as well. So we have three people in America, and then most of our developers are hired in Portugal and Spain, although we actually do have one here in Romania. And then the rest of the team is spread about Europe and in the UK. So in total, we have about 22 employees of You Can Book Me, but we have an effective head count of more like 30 because we employ a lot of partners and people who work for us one way or another full-time or contractors.

[00:03:05.350] – Joran

Nice. We’re going to dive more into that. I guess, can you explain in one or two sentences, what does You Can Book Me actually do?

[00:03:11.220] – Bridget

You Can Book Me is an online scheduling tool. So you connect a booking page with your calendar so that you can show your free times in the form of slots that people can select, fill out their details, and secure a slot in your calendar to book you.

[00:03:24.770] – Joran

Nice. And so you started the product in 2003 before politics. Is this your first startup?

[00:03:31.560] – Bridget

Yes, that was a totally different product in 2003. But the point that I’m trying to make is that building products of which you can book me is one of around 10 products we’ve built, is different to a company, which is what you can book me in terms of employees, which is different to a business, which is how do you make money and what a business are you in? We’ve been building products for over 20 years. The first business that we were in was You Can Book Me because it was the first that started to make money from customers. And then You Can Book Me as a company has grown up over the last of 12 or 13 years. This is our only thing. We’ve never done anything else. Nice.

[00:04:05.640] – Joran

So it’s, I guess, one out of 10, which actually went through it.

[00:04:09.060] – Bridget

We’re on course in terms of the probability. I love it.

[00:04:13.190] – Joran

Have you always wanted to be an entrepreneur?

[00:04:15.080] – Bridget


[00:04:16.850] – Joran

Nice. We’re going to dive more into that as well. May I ask how young are you?

[00:04:22.230] – Bridget

Oh, I’m 50 years old. I’m very proud of that fact. I think that by telling everybody or starting a sentence now that I’m 50, it makes me feel a lot more I think I’ve definitely got wiser as I’ve hit the second half of my life.

[00:04:35.980] – Joran

Yeah, no, I can definitely agree to that because we had some good conversation in Morocco already. Do you have an end goal defined with You Can Book Me?

[00:04:43.390] – Bridget

Obviously, that is completely dependent on how you look at it. For me and Keith, personally, I would say we’ve reached a lot of our goals. We’re financially secure, we are independent, we get to control our day-to-day life, we get to do whatever we want to do. So if you say, do When we set out 20 years ago to be financially independent and in control of our own destiny, we’ve achieved our goal. On the other hand, I care very passionately about the product and what it can do for our customers and also for the team that work on it. So if you can book me as a product, I have a huge amount of ambition for it to keep going from strength to strength, for it to help empower small businesses so that lots of people can use our tool to help them build their businesses in a way that is efficient and effective and hopefully cost-effective for them. And then for our team, I think that there is, as I said, I’m 50, most of the people who work for us are in their 20s and 30s and 40s. I have a lot of ambition for them because I see myself in their shoes when I was in my 20s, and I still want You Can Book Me to be the company that offers opportunities for those people so that they can grow their careers inside You Can Book Me.

[00:05:53.400] – Bridget

So to that extent, no, we have not reached yet our goals for the product, the customers, and the team. But for me and Keith, as founders, we’re very happy.

[00:06:01.410] – Joran

Yeah, and I think that goes really well to the next question, what keeps you motivated? You probably answered just-That’s basically it.

[00:06:07.890] – Bridget

I said this to my team, just we went on a team retreat in Scotland a couple of weeks ago, and I said that. If I was still insecure and unhappy in my 50s about what I wanted to do in my life, I would say I had a deeper problem than just running a software company. In fact, I’m pretty content. However, I am not the same as somebody in their 20s who wants to learn, grow, and develop. And all the life changes that happen, you get married, you have kids, or you go traveling, or you decide who it is that you want to be. These are all things that help get supported by a company like You Can Book Me. And I find that very motivating.

[00:06:43.060] – Joran

Yeah, I think that’s something all Almost you can do back, I guess, towards others, which is really nice that you can see other people grow as well.

[00:06:50.310] – Bridget

Yeah, and I won’t lie, it is also part of my competitive nature, which is I want to build a really good company. I want to be able to show and demonstrate it’s possible to build a company that people love to work for. And that we get away from this grim work culture where people feel like it’s all about not working and getting away from work because work burns people out. I’m not saying that we do it perfectly all the time at all, but we work hard at it.

[00:07:15.060] – Joran

If we go all the way back, and we’re going to now dive a bit deeper. How did you came up with the idea of You Can Book Me? So 10 products, right? Yes. One succeeded. So how did you came up with You Can Book Me as it is, right?

[00:07:28.810] – Bridget

So You Can Book Me was born out of a classic pivot from a different tool, which was also a scheduling tool. So as I said, Keith, my co founder and CTO, he built a product a long time ago in 2003 called Tickboxer, which was a really successful tool in the sense of software and product, which was a survey building tool, but it had no customers and no users. So we sunset it pretty quickly. I have to say we had two users, myself in local government, and one of Keith’s clients also used it, but that was it. Then about Five years later, he built a tool called When is Good, which is still going at the moment, which is a tool that finds time for a group of people to meet. And that had loads of users. Thousands of people signed up, thousands of people used it, but no customers. But from When is Good, we could see the potential of turning or Keith could see how he could integrate a booking interface like When is Good with a Google calendar. And that was in 2011, and that totally took off. So we ended up with loads of users, thousands of plus customers.

[00:08:31.430] – Bridget

And so to an extent, You Can Book Me was born out of 10 years of experience of what wasn’t going to work and what didn’t fly out the door. But the product market fit for You Can Book Me happened almost instantly. And maybe had it been Our first product, we’d have taken that for granted. But the fact is we knew this was it, that this was something that was going to fly.

[00:08:51.410] – Joran

Yeah, and I think the good thing here is you already know exactly what they’re looking for, plus you had a community or users to actually tap into. As you mentioned, product market almost happens instantly. Did you know from the beginning it was going to be such a success?

[00:09:03.660] – Bridget

Well, no. You never know anything. We knew it was going to be a success in the terms of exponential growth and commitment. Lots of other things take over. So your relationship with customers takes over. So if you’ve got customers emailing you all the time with feature requests and wanting to give you more money and wanting you to build more, you can get this momentum that is externally generated that you then continue to respond to. So in a way, you haven’t got time to worry or think about whether it’s going to be a success or not, because if your day is spent all day, every day talking to customers and building product for them, it stands to reason that it’s going to be successful. We didn’t know. I didn’t think I’d be sitting here 10 years later in a hotel room in Bucharest talking about a multimillion pound software company that has made a lot of money over the years. I think that’s probably one of the pieces of advice I would have. If you’re bootstrapped, you can afford to think like this. If you’re VC funded, they do have a very mechanical business plan that you need to work towards, which is It’s perfectly legitimate.

[00:10:01.420] – Bridget

So they’re like, we’re going to give you this amount of money that you need to turn into that amount of money within a couple of years, or you need to raise more money to add to the pot one way or another. And so you need to hit these metrics for a product market fit or for growth. And that’s fine because the investment is being put in for a return. Whereas with bootstrapping, you can afford to do things a lot more slowly. You can just manage your cash and make sure you don’t run out of money. So for me, success for the first seven years was not failing, was not running out of money, was staying alive, being able to pay myself, Keith, and others in the company, and holding on, really. So for me, success was not failing. And now it’s okay to find success now. Do we want to be as big as Calendly, or do we want to be bigger than Calendly, or do we want to IPO at some stage? There’s lots of options for you can book me as a product that we can consider now that would be inconceivable for me to have thought about at the beginning.

[00:10:55.460] – Joran

Yeah. And maybe one thing good to know is you even wrote a manual on how to bootstrap or the bootstrapping manual.

[00:11:01.710] – Bridget

The bootstrapping manual, which hopefully you’ll put a link in the comments to, Jorn.

[00:11:05.470] – Joran

A hundred %. Yeah, no, it will be at the top.

[00:11:07.150] – Bridget

And actually people will know that if they follow through on that, they do get a freebie in terms of a free upgrade on You Can Book Me. Yeah.

[00:11:13.080] – Joran

I read it after the Marrakesh trip, which I really loved. I really enjoyed it, reading it and made a lot of notes. So that’s really nice. One thing I wanted to ask, you advocate a lot on bootstrapping, right? You can clearly see that you’re getting enthusiastic about it. Was it a conscious decision to never take any external money or at least VC funding? No, it wasn’t.

[00:11:36.000] – Bridget

We weren’t ideological about it. We were pretty naive and not very well-informed, but this was, of course, 12, 13 years ago. You wouldn’t launch a startup now in 2024 and not know all your options or find my bootstrapper’s manual or talk about it with people who’ve raised money or other founders. The networking that’s available now for startups is incredible. Whereas you’ve got to imagine that me and Keith started You Can Book Me in 2011 or 2007 with When It’s Good. That’s 2007. There weren’t any SASTRE or SaaStock local meetups in London or nobody knew what we were doing. The banks thought we were crazy. Our friends and family looked on bemusededly about what we were trying to do. So we had no context about what our options were. And at various times, we ran out of money and we had to borrow money. We did. We had private loans. We borrowed money from the bank in the form of an overdraft. And we did do pitch days where we had angels talk to us about potentially investing in us. But I just got the wrong vibes from those meetings. And the vibes were, oh, they’re going to give me money, but then they’re going to tell me what to do with that.

[00:12:41.460] – Bridget

And I don’t want that. I want to just have control over our lives. And not just, obviously, you can book me, but the rest of our lives I want to control over. And so I didn’t want to suddenly hand over a chunk of my… I didn’t see it as in terms of equity in my business. I saw it in terms of how much permission somebody has to me what to do every day, and I didn’t want that. So it was more of a personal decision in some ways than financial. We probably should have taken the money. If you look back and you look at the history of You Can Book Me and Calendly, which is launched a couple of years after You Can Book Me, and it’s obviously done really well as an incredible company. And we’ve met the founder a couple of times, and he’s absolutely great. We have a huge amount of respect for that as a product. But if you look at You Can Book Me that launched a few years before Calendly did, I don’t wish that we were Calendly. I don’t wish that we did something different because I know that over the decade of us building You Can Book Me, we built on our own terms with success defined by our own goals.

[00:13:38.140] – Bridget

And we did not consider VC funding for another few years. And then we did again. We had another meeting with some VCs in London. And again, it was the way we approached it and what we talked about and how we described our business and how we cared about it. I think we just came across as a bit mad or eccentric to the VCs because we didn’t sit there and say, we’re going to give you a 10X exit over the next four years, and this is what you’re going to do. We just came across as obsessed with customers, obsessed with our product, obsessed with online scheduling, super detailed and focused. But we hadn’t contextualized You can book me at all as a financial opportunity for other people. It was a bit like, yeah, join the scheduling gang and then really get into new features that we want to build for our customers. Here they all are. There’s thousands of them. And I think the VCs were like, who are these people? We can’t. We VCs couldn’t deal with us. We couldn’t deal with them. So it wasn’t ideological. And now, as I said before, I am 50.

[00:14:37.220] – Bridget

I’m a lot wiser. We’ve personally, me and Keith have now invested in various funds. I’m not against it at all. I just think it’s a tool. The money that’s coming from investors is a tool. It’s a relationship you have with them. I think that we all got a bit mad a few years ago, and everybody thought that starting a business was actually about taking money off VCs, and VCs become your customers, and you I have to obsess about what VCs think. I think now that since the last couple of years, everything has gone a little bit south for people, everybody’s realizing that the entrepreneurship and the founder spirit that is there, that should be held in the sovereignty of the entrepreneurship community, not the investor community. And the investors are lucky if they get to invest in our companies, not the other way around.

[00:15:22.170] – Joran

Yeah. It’s funny because you came out of politics and you don’t want to have the politics within the company. That’s why you didn’t- Precisely.

[00:15:28.430] – Bridget

Absolutely. Precisely. And I think that, frankly, and I’ve never said this before, actually, and I don’t want this to be too overblown, but it’s a lot of white men in the investor community. And I’ve just come out of politics, which is an endemically sexist culture. I think software and technology industry has its problems, clearly, not unsurmountable. But as a female CEO, it would have been me essentially deferring to a lot of white men. And again, there’s a part of me that’s over that.

[00:15:56.490] – Joran

Yeah, I can imagine. We’re going to dive into the fund It’s been a more fun moment now to talk about it in hindsight.

[00:16:02.430] – Bridget

It has not been fun up till now.

[00:16:04.870] – Joran

Because everybody hits a rock button moment, right? We already mentioned friends thought you were crazy. You did the private loans. Can you tell anything about some rock bottom moment, which is either financially, personally, and how did you came out of it?

[00:16:19.060] – Bridget

There’s a long list, obviously, because we’ve been doing it for a long time. But I would just like to say, yes, of course, there’s times when I can say that things are hard, and there’s no doubt it’s tough. And especially it’s painful when particularly people have taken on funding and they’ve just run out of money and they have to close their software company down or they have to move on or they have to accept failure. That is incredibly painful. There is no doubt about it. If you double your energy investment into something to make it work and exist, and then it’s taken away from you, you get double the pain. So I get that. On the other hand, rock bottom for me is losing my home, losing my family, losing everything. And I must say that, and actually, I genuinely would advise this to anybody starting their own company, do not put your family and your home on the line. I never did. It’s a personal choice in my bootstrapping manual, which I have to say is completely free. I’m plugging it as if it’s on the Amazon top best selling list, but it’s completely free.

[00:17:11.690] – Bridget

But I say I list the things that were my red lines in terms of what I wasn’t prepared to sacrifice. For example, I wasn’t prepared to borrow more money than I know I could personally pay back in the course of an ordinary job. So like a student loan, I wasn’t prepared to put our asset, which was We had a two bedroom flat in London. It was our asset that we didn’t have a mortgage on, so as a result, we could earn from renting it out and that thing. I was never going to mortgage my home. I never sacrificed family time that we wanted to prioritize for the sake of the company. I think that’s because people do that thinking that it’s all going to be great next year. I still do. I still think next year is going to be a turnaround year or everything’s going to come together by September. I still have deep optimism and energy for short term deadlines. And all that happens is it’s like it’s a marathon based on a series of sprints. People say it’s a marathon, not a sprint, but nobody can conceptualize the marathon. So what you have to realize is every sprint you do is build up to basically a marathon.

[00:18:18.800] – Bridget

So back to your question about Rock Bottom, those times we’ve hit when we were being overwhelmed with support, myself and Keith and our colleague, Kate, doing tickets, support tickets till 2:00 in the morning, and there’s still 70 in the inbox. That feels horrible because you’re letting down customers, and it just feels grim in the middle of the night to be answering tickets to school secretaries in America who are trying to get their help with their booking pages. And you’re like, this is not going to be done. I have to go to bed, and the work is not going to be done. Anything like that feeling is awful or when the service has gone down in the years gone by. I think there was times, personally, when me and Keith, we became profitable in 2016, 2017, we made our first hundred thousand pounds over a million. So it was basically a 10 % profit margin. We hit our first million and we done a 10 % profit on that. And that felt great. But then, of course, don’t forget we had been That was nearly 10 years, from When is Good, from 2007 through to You can book me.

[00:19:20.200] – Bridget

So that’s 10 years of not knowing whether we were actually going to make money. And so there was plenty of times when Keith was a developer. So he was like, I could just get a job as a developer. And I remember this one time when there was this job for a software developer, like a Java developer in Luton. We live in Bedford. It was like 60,000 a year or something or 55,000 a year. And he went off on the train to go and get that job. And he came back and he didn’t get the job. But it’s, oh, God, Keith can’t even get a job in Luton. What are we going to do? How are we going to move on? And at the time, all of our friends were getting mortgages and buying new cars and going on nice holidays. And we weren’t. We weren’t doing those things. And so it’s a, Okay, how long are we going to take this for the sake of something more? And that can sometimes take years. So I wouldn’t say that’s rock bottom, but I would say you’re bumping along the floor for quite a long time. And you just have to be…

[00:20:11.430] – Bridget

Some people would not accept that. Some people would say, no, I’ve got the skills to go and get three-figure salary from a big company and get share options and do it a different way. Completely fair. We decided to do it this way. And there was plenty of times when you don’t know whether necessarily this was the right decision or whether you would do it again. And I have to say, You Can Book & Book me has been… It’s not 100 % the same, but it is running your own company over 10, 15 years as co-founders, as bootstrap founders. It’s close to basically birthing a child. You can’t get away from them. They’re completely dependent on you. Children, obviously, slightly separately because they’re glorious and beautiful. But a company becomes extremely dependent on you. And so it’s a 24-hour responsibility. And I think it’s that slow burn over many years that you have to watch yourself.

[00:20:59.260] – Joran

Yeah. Because as you mentioned, you can go from thinking about next year is going to be great, or if I do this, it’s going to be great. But you always have that feeling, even now when things are-Yeah, you have to say maybe no.

[00:21:10.850] – Bridget

So for example, we built other products that we just had to close down because we had the enthusiasm of being able to launch them. Everybody loves thinking of what the domain name is going to be, pootling off to Hover and buying it and little MVP going, talking about it down the pub. Everybody loves that part of it. But it’s the actual grind of a company in a business, not the product, that takes the time and can grind you down if you’re not careful.

[00:21:35.400] – Joran

Yeah, and I think you have the clear example. It took 10 years to actually get to a point where you got money. Where we made some money. Yeah, exactly. So you will have to put in the work. And it’s not just building an MVP from a pop conversation into something. One thing I wanted to ask still is the support tickets, right? You did that until 2:00 in the morning, 3:00 in the morning. How did you overcome those moments to make them a bit more positive? It was a challenging period.

[00:21:57.540] – Bridget

Yes. Oh, change. Every time it’s changed. I’ve said this before publicly, I’m very selfish and lazy. I don’t like doing things that I don’t want to do. So if I’m doing tickets at 2:00 in the morning, I don’t do that for very long before I change it because it’s not acceptable. So most of the time, anything where you think the company cannot depend on me doing something at 2:00 in the morning, I change it. So I hire more people, bring in better systems, change the software, remodel what we’re doing, change how often we’re offering support or to whom we’re offering support, make everything more automated, constantly change it. I don’t want to or intend to put up with things that affect my life negatively.

[00:22:39.420] – Joran

You mentioned it almost being selfiness, but it’s also more putting yourself in your strengths, as in if you don’t want to do supporting it until 2:00 in the morning. Exactly.

[00:22:48.490] – Bridget

I’ve got to change it. Yeah. I’m not a self-sacrificer at all. No.

[00:22:52.370] – Joran

In the end, you did it, you experienced it, you don’t like it, so you’re going to change it for the better and you probably know exactly how to change it because you already did it before. Yeah.

[00:23:00.500] – Bridget

And then I think I would say as well, again, that’s the longevity of my experience. That’s not the last time support’s melted down. Anything that you get set up and done in the correct way, you can feel satisfied that you’ve sorted that bit of your company out, and then you can go look at something else. And then after a couple of years, it will all fall apart again. I’ve seen that several times with multiple departments. You think you get it all sorted, side relief, it does work for a while, and then it just falls apart again. And so everything needs continuous maintenance.

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[00:23:50.900] – Joran

If we talk about those moments where things fall apart, like what has been or what has been some couple big company challenges you had along the way. So I guess, struggling moments.

[00:24:02.660] – Bridget

We’ve had technical moments because we’ve had to maintain the technology stack to keep it up to date. And that’s meant two or three huge migrations from, for example, the original application was a back-end application, server-side application. And we have now just completed this year, last year, the final part of the project to move the whole of the application that people would use and interact with the booking pages, the account settings, everything, into the front-end, into React. And that project started in 2016, where we basically did all of our account setting that went into the front-end. And then a couple of years ago, we started work on the booking experience, and then that went into React. And that was challenging because it’s boring for people to have to either work on an old stack that’s got problems that you then say we’re not going to carry on innovating in that old stack because we’re going to rewrite it and put it into the new technology, or people People are working on migration, which is always difficult and boring to have to move millions of lines of data one way or another across to a new version, or the new version isn’t working as it should do because you haven’t put all of the new features into it that you intended to do that were supported in the old version.

[00:25:16.900] – Bridget

So none of it is great. Again, we’re a 12-year-old software company as opposed to a two-year-old software company where everything’s greenfield, everything’s a new feature. It’s all super exciting. And so you have to educate the team inside a company like ours, which is sometimes you just got this big, serious, meaty, chunky thing that we need to do, and it would be a mistake to ignore it. So if we were still on Java back-end applications, we would have died by now as a business. So you have to do it. You have to You have to invest in it. You have to plan and project manage it. It’s just not that inspiring or motivating for people.

[00:25:51.130] – Joran

No, we did the exact same thing. Luckily, we weren’t that big at that time, so it only took us six months. But for me, I think I made a lot of mistakes where we just This big goal, I’m not a developer, so my goal was just to get the migration done. That was my end goal. But to get there, you need a lot of steps. If you’re going to do it for such a long period, you need to properly plan it, but maybe even more importantly, keep the people motivated to get to the end goal. How did you do that?

[00:26:16.060] – Bridget

I think some of it is just really good project management because people can be motivated by reaching milestones. So everything needs to be properly tracked. So you reach a milestone every Friday, let’s say, then people understand and they can track their progress. I don’t think you can stop doing exciting motivating things elsewhere. So we didn’t stop doing things that were for customers. It just had to happen at the same time as these large changes. I think our team in particular, we’re small and we’re remote. And so we do have this opportunity of meeting up and having a lovely social time when we meet up. We’ve been to Scotland, as I said, a few years, weeks ago. Last year we were in France. We’ve done obviously COVID intervening, but we’ve done other really nice meetups in countries like Costa Rica and Málaga and Alicante and Dominican Republic and Lisbon. And we’ve tried to get the team together in places where we can really enjoy the work. It comes down to the similar concepts, which is teamwork. If you make the work happy and enjoyable because the team likes each other, even if the work is difficult, they will stay motivated to get it done.

[00:27:18.960] – Bridget

You have to keep on showing results as well, being able to say, You did all of this, and now look at this. This is what people are experiencing in the product. And interaction with customers and understanding how customers like your product is very motivating for everybody.

[00:27:31.290] – Joran

Yeah. Keeping it updated on what’s going on probably helps as well and why you do things. Cool. If we go back to the fun part, you’ve been growing fast, right? 1.5 million bookings per month. I handle every month, 20,000 customers. What has been your go-to market? What have you been doing really well to get to the point where you are right now?

[00:27:53.620] – Bridget

It’s not, unfortunately, a very easily transferable insight into You Can Book Me, which is its viral growth loop. Those bookings deliver new accounts for us every month. So even sitting still on any other activity, we would get account growth. However, right now, particularly in the world of SaaS, the plateau that we’re in, it’s really tough because competition is tough and brand recognition and understanding what the product can do. All of that is super tough. So again, I would say part of our go to market strategy is to not fail in the market that we’ve been given. So in viral growth, we’re given a market of people who want to use the scheduling experience, the scheduling tool. So we need to make sure that our booking tool is as good as it can be. The experience is great. We’re rolling out lots of changes to the tool at the moment, and we need to keep on investing in our product because product-led growth is the thing that people most know it’s about. They know about You Can Book Me because they’ve heard of You Can Book Me because they’ve booked using You Can Book Me, or they know it works better for them because of our integrations or the way that we handle something in very particular, sometimes very specific things that we do that Calendly doesn’t do, for example, or HubSpot doesn’t do.

[00:29:06.240] – Bridget

So they go, We use you for that. So we have lots of teams and small businesses who use You Can Book Me because they love it for what it does for them. And then we rely on their word of mouth to tell other people. And we rely on the fact that the people who are booking onto their booking pages will go, Oh, I really like this experience. Who’s giving them this experience? This feels different. We will create an account and have a look. So that’s essentially the word of mouth viral growth loop that we’ve relied on. And then I do believe that, as I said, over the investment over the last 10 years, we have continued to invest in the tool. We’ve continued to invest. So we haven’t broken, we haven’t fallen apart. We don’t look aged. Our UI is beautiful. There’s a lot of stuff we’ve just continued to invest in, and that’s because instinctively we’re a product-led growth company.

[00:29:51.740] – Joran

Yeah, and I think there’s one important thing, right? If you want to have that viral loop, which you guys are going right now, you need to have a good product. Because if people have a bad experience with booking a call or booking scheduling something, then they would probably not use the product. So in the end, the product is the basis, and then from there, you build on top of that, of course. Absolutely. It’s always fun and always difficult. Are there any certain decisions or any certain things you’ve done, as in if I haven’t done X, Y, or Z, then I wouldn’t have been here today. Within the go-to-market or within the strategy of growing, you can book me.

[00:30:26.690] – Bridget

Yeah, you could go back on all the hypotheticals of what we did and say, take those away, would it have happened? So for example, Keith, as the CTO co founder, he was doing all of the software development 15 years ago, but he wasn’t in a position to run a business in a company. The decision that I took in 2012 to, in effect, forego my career that I had already established in politics in Westminster in the UK, to run a software company. To answer your question earlier about did I ever want to be an entrepreneur? No, it was not. I did not sit there and say, I want to run a business one day. It was not in any way one of my life goals at all. But on the other hand, as I said, being married to Keith and having this experience of building web products, web development, which was giving us and yielding this opportunity for income. Clearly, I had this option to run You Can Book Me and see how we could develop that into the best opportunity we could. We worked very hard together and separately in terms of our jobs. So Keith doing technology and me doing the business and company finance operations.

[00:31:28.410] – Bridget

That between the two of us, we managed it. Now, I think that you could say plenty of scheduling tools have come and gone, and plenty of them have. Doodle, years ago, had a scheduling tool close to You Can Book Me that they closed down. I think they’ve got something spilled back up again. But we saw Google Appointments service. Again, Google Appointments, was launched in 2012. Then they closed it down to people. We had probably all these tools people won’t have heard of, but things like Tungle was a competitor at one point, and they were acquired by Blackbury, and then they got closed So over the years, we saw lots of booking tools like ours not making it one way or another. And I think that’s probably because small businesses and people who rely on, you can book me or rely on bookings for their business, they’ve got high expectations and not a lot of cash to spread around. So in any economic environment where you’re trying to serve a small business environment, it’s hard. It’s really hard work. So there’s probably wasn’t any guarantee that it would have happened had me and Keith not been fully committed together as cofounders to make it work.

[00:32:34.630] – Bridget

So I think it did happen because of blood, sweat, and tears. It didn’t happen because of some magic in the market that we were gifted. It happened because we didn’t give up.

[00:32:42.980] – Joran

Yeah. And I think it’s a really critical decision. You quit your job from politics, you committed to go in 10 years to actually get your profit right, and you fully obsessed over product and customers, which I think is the most important thing you can do.

[00:32:55.910] – Bridget


[00:32:57.130] – Joran

Nice. We talked about product-led growth, viral loops. The question I want to ask now, do you use any processes or frameworks to grow You Can Book Me? You also are a big advocate on profit sharing, so motivating the team. Are there any things you maybe can explain here or maybe other things you use internally to grow?

[00:33:16.750] – Bridget

Internally, just organizationally, if this is helping answer your question, we have adopted over the last year Traction, which is the entrepreneur’s operating system. And that is more designed to keep a small remote team on track with a lot of deadlines and ambition that we have every quarter to deliver what we set out to deliver. And I adopted that last year and it’s worked really well. And that has helped filter down to project planning and project management so that we’re able to fully define the priorities and plan for them over and above anything else that we thought about wanting to do. Otherwise, what tends to happen is everybody has their own agendas about what they think is important, and everybody goes off and starts doing random things. And And it was about saying we have to be super clear on what the priorities are. Following on from that, we’ve also done a huge amount of work in the last year on our ICP, who’s most successful using You Can Book Me. And because it’s a horizontal tool, we’ve ended up with lots and lots of articles. You could say we have dentists that use You Can Book Me.

[00:34:18.340] – Bridget

We have huge tech companies that use You Can Book Me. We have parent-teacher conferences that use You Can Book Me in education. So how on Earth do you form a marketing strategy around everybody? Because if you’re everything to everybody, then you’re nothing to nobody. I don’t know if that double negative works, but we have been focused on a much better strategy around who gets the most benefit out of using You Can Book Me, which in turn informs our product priorities, which in turn informs our planning. To an extent, I’ve spent the last year internally focused on getting the ship super tight in what we build, who we build for, why we’re building it, and when we’re going to build it. And that has yielded some great results in terms of things that we’ve rolled out today. We’ve just rolled out our, I will do a pitch now. You’re in a premier HubSpot integration. It’s literally the best on the market. If you’re not using HubSpot schedulers or you don’t like it, but you do use HubSpot, you should be integrating with You Can Book Me because everything from bookings from You Can Book Me goes into HubSpot beautifully.

[00:35:17.140] – Bridget

That thing, which we set out and understood that we needed to prioritize and build. And I think that that’s going to help us grow. That is obviously there to help us grow. Something else we’re doing is changing our pricing because our pricing essentially stopped being fit for purpose a few years ago, and we didn’t have the capacity to really think about it at the time. But now we’re rolling out new pricing in the summer, and that’s designed to make it more cost-effective for smaller paying customers. We’re basically too expensive for if you’re a digital entrepreneur or a coach or a creator or somebody on the internet with a business, if you can book me, we’re just a bit more expensive than we should be. So we’re rolling out pricing that fits people and their businesses so that they’ve a scheduling tool that works for them but also doesn’t cost them as much. So being able to be a bit more price sensitive is something that we focused on to help us grow. Another big one was we put into the product our premier, I think you We’re probably going to ask questions about this, and this is my answer again, which is our overlay availability feature, which is if you had a YouCanBookMe account, and you went to bridget.

[00:36:25.340] – Bridget

Youcanbook. Me, you would be able to overlay either your YouCanBookMe account or indeed calendar our account, or indeed your Calendly account, which I think you use Calendly, and you could overlay your times onto my You Can Book Me. And we do that because we want to make it really easy for bookers on any scheduling tool themselves to be able to book somebody on You Can Book Me so that you’re offering a link which isn’t just a one-way link, it’s two ways. So we did that, and to build that, we had to do a lot of the technical debt reorganization I was talking about. But what we’re trying to build is a advocacy for bookers so that when people are using a scheduling tool, it’s not just here are my times, but instead it’s you can use this as a tool for you to tell me when you’re free. And again, that’s all rooted inside growth because that’s the viral loop. That’s about Booker is being able to see the value of You can Book Me when they book on a You can Book Me page, and then they can hopefully go off and create their own You can Book Me page.

[00:37:22.490] – Bridget

Even if they were using Calendly, they can see that it’s compatible with Calendly. We literally integrate with a competitor. But again, to get that done, we We needed our internal systems and our focus needed to move away from something else. So we had to essentially change and pivot from what was other people’s product priorities and what they wanted to build to really focus on these things. I think that was the hardest thing we did last year, and it yielded results. I’m really happy.

[00:37:50.390] – Joran

Yeah, because you focused on product experience. How are people experiencing a product? You focused on that and not building a We’re a set of horses.

[00:38:01.360] – Bridget

Exactly. Yeah, this is it. We have a lot of people with very large teams that you can book me. And there’s a lot of things that are a bit niggly and they don’t really like. And so we essentially compensate for that with customer success. So we have a great customer success team, and they do an awful lot to help support our clients, but it’s not ideal. And so our ambition will continue to be, let’s make sure that there’s grievances, if you like, inside the larger team management use of You Can Book Me that we can fix and an overall upgrade. However, it’s nothing compared to, let’s make it cheaper for coaches, let’s make it cheaper for digital marketers, let’s just do the things at that end that is really going to transform and grow the awareness of you can book me as a tool for small businesses.

[00:38:47.200] – Joran

Yeah. And one thing you mentioned as well as in you kept focusing on your ICP and you mentioned who gets the most benefit, which I think is interesting because you didn’t say who pays us the most. You actually say who gets the most benefit. So you really looked at who’s using the tool to the…

[00:39:02.410] – Bridget

Yeah, and I can elaborate on that. So these are people who’ve used YouCanBookMe for years. We’ve got people who’ve used YouCanBookMe for over 10 years. These are people who are coaches who’ve used YouCanBookMe consistently over the last six, seven years, they’ve got thousands of bookings. They’ve never churned. They’ve never complained. The product has always been perfect for them. It’s always done exactly what they wanted to do. And they’ve seen all of the changes that we’ve put in over the years, and they’ve really liked them. We’ve turned around and we’ve almost gone back to our roots to say, look, we can’t be all things to everybody. We can’t go out there and try to take on the enterprise customer engagement market that it seems to be Calendly is doing with Salesforce and HubSpot at that massive level of CRM world, because scheduling, of course, you’re in people’s calendars. You’re very much inside a CRM type stack. But we can’t drink the ocean. So we just looked at for us, where bookings are somebody’s business, where we really matter to somebody, because if they don’t get bookings, they don’t earn. Their job is essentially being fueled through the bookings that they take.

[00:40:07.460] – Bridget

We really matter to them. And inside the company, we had a theme in our Scotland Week, which is making friends with our customers, that connection with our customers, where we matter to them, they need to matter to us, and then therefore we can help understand internally what that emotional relationship is like. So people can feel like you’re really helping out a friend when you’re building a feature, that Yeah, and it goes really well.

[00:40:32.210] – Joran

And the other thing you said, pricing that fits people. So you’re now also making- You’re one of the first people to tell me that we were too expensive, and it’s bugged me ever since.

[00:40:41.650] – Bridget

Sorry about that. We’re building specifically for you, Jorn.

[00:40:44.160] – Joran

Nice. So we are going to round up. You gave so much advice already, but if we’re going to break it down into revenue stages, what advice would you give someone who’s just starting out and growing to 10K monthly recurring revenue?

[00:40:55.940] – Bridget

Yes, I thought about this. I just think there’s only one thing which is don’t run out of money. I just think it’s cash management, honestly. Good solid financial tools, tooling, a solid financial set of banking and reports, and you know what your cash flow is, you know how much everything is, and try to avoid spending money on anything that you don’t have an immediate reaction back to what you can do with that. So if you’re spending that money on developers to build the tool, great. But as long as what they’re doing is building something that you know you can immediately sell back to customers. So at this stage, there’s really no other It’s a priority. Don’t run out of money. Cash is king.

[00:41:33.220] – Joran

Yeah. And one other thing you mentioned a lot, do you already recommend obsessing over customers in this stage?

[00:41:38.940] – Bridget

Oh, yeah. Yes. I’m taking that as a given. So the thing is that people might think, oh, I’ve got to, I don’t know, spend money on going around and advocating or marketing or lots of merchandise. Or like at the time when we started, we had, do you remember the Google Chromebooks? They were 200 quid. We didn’t sit there and go, yeah, everybody’s getting MacBook pros. You can get caught up in startup world where it’s all about yoga in the morning and free fruit in the afternoon. And none of that is related to customer value. So it’s about what can I spend money on which is going to give additional value or a feature to a customer. And you keep that feedback loop from customer to cash to value, really tight. You don’t run out of money because you only spend money on things that matter to customers.

[00:42:26.330] – Joran

Yeah, and in the end, you’re probably building a team which cares about customers as well.

[00:42:30.340] – Bridget

I don’t care about it anymore. So I was telling my team this a few weeks ago. In the early days, Keith, as a developer, if you could book me, he would spend the morning on taking customer emails, finding out what they wanted. He would interview them, he would talk to them. And in the afternoon, he would do the feature, he’d roll it out, and then the next morning, he’d email them back to say the feature was rolled out. It was like magic. They thought he was magic. There was a lot of early lean, agile philosophy there that we didn’t know that’s what he was doing, but it was his instinct to do But we weren’t making any money at this point. The money, especially with You Can Book Me, we’re selling 20 quid a month type application here. It took us a long time to build up any income from You Can Book Me that was any of us could live off. At the time, just to give you an illustration, at the time that I gave up my full-time job, we were bringing in £2,500 a month. That’s nothing. It’s nothing. So that’s why we’re very cash-conscious.

[00:43:28.010] – Bridget

And it’s probably now something Something I probably need to loosen up a bit more about because when you’re that cash conscious at the beginning, you don’t spend money on anything. You’re also probably not investing in longer term things that probably would benefit. But don’t run out of money.

[00:43:43.760] – Joran

Yeah, That’s a really good advice. And I guess if we go past 10K MR and you’re on your own journey right now, 5 million AR, what advice would you give maybe yourself or others who are past 10K MR, growing to 10 million AR? I know it’s a big step.

[00:43:58.690] – Bridget

Yeah, no, no. And I I still have to learn these lessons myself because we’re struggling to get to 10 million. It’s not easy for us. It’s not like some flick of switch and you do it. I’m continually struggling on figuring out what it is that I need to do. I actually think it comes down to one thing and one thing alone, which is people. I think you can’t even get to five million or you’re very lucky if you do without a team of people, and you certainly need a very strong team of people to get to 10 million. And people have different ideas about what they want to do. The books that I’ve read recently, Traction, but also Radical I found very useful. But I think that having a deep investment in understanding how you’re going to work with people, what your company culture is going to be like, what your organizational values are going to be like, how are you going to manage a team and how are you going to manage people. So for example, as CEO, I have obviously my direct reports, but I don’t spend a lot of time in meetings where I’m helping deliver the work.

[00:44:51.940] – Bridget

So I have very strong people who work for me who are delivering the work. And I think that for you to get from 5:00 to 10:00, this is what I myself I’ve learnt and been reading about and listening to podcasts is the leaders, they have to have some time spent looking and thinking about the bigger picture strategically. And if I don’t have time to do that because I’m spending proverbially carrying on doing the support tickets, I would never be able to do it. So it’s a dual thing. Your company needs to be resilient, strong enough with very strong people to run the company for you so that you have got that time to do the strategic stuff. But also, emotionally, you’re never going to get there if you’re still absolutely in the weeds of the business. And that relies on people, and people are hard. They’re amazing and also the hardest part of any company. So you have to be very good at dealing with people and understanding people.

[00:45:47.080] – Joran

Yeah, and probably hiring the right people because I think the thing I took away from Jamie in Morocco was if you hire somebody who’s much better than you and they’re going to do it much better than yourself, then it’s easy to let go.

[00:45:58.910] – Bridget

Yes. Yes, that’s very true. But that’s also quite dangerous because particularly in marketing, I have to say I’ve had my fingers burnt a number of times. I believe that philosophy. I believe that somebody is better than me. I’ve given them loads of money, and then they’ve gone off and they’ve burnt it anyway. So There’s no department that we haven’t been burned by the belief that somehow, Oh, you must know what you’re doing. There’s no savior inside HR. At the end of the day, you’re still responsible for what you’re trying to achieve. And it’s very hard to draw a line with somebody to say, I actually don’t think that you’re right and I need to do this a different way, or indeed, how you let go and trust people. It takes time and you need to get very good at understanding your own motivations and your own boundaries and how you trust people as well as other people. It doesn’t happen by magic.

[00:46:43.890] – Joran

Nice. I think it’s a really good closing statement. I will try to summarize a little bit. We talked a lot about bootstrapping, right? It’s a marathon, so it’s definitely not a sprint. But don’t sacrifice things now because you think they’re going to be great next year. So don’t put your family and house on the line. Don’t borrow more money than you can pay back.

[00:47:01.580] – Bridget

If you’re in my situation, because I was in my late 30s, even you’re in 20s, you can do what you like.

[00:47:06.090] – Joran

Yeah, in the end, there’s not much you can put on the line at that point anyway. I guess if people are buying houses right now, you will make sure that you are on a marathon, so it will take time. When being fully remote, like you did, came together quite often times in really exotic locations as well, which is nice. Want to get a viral loop going or word of mouth, good product and customer experience is key. People Check out Traction, the EOS. It helps with planning and reaching goals. Keep focusing on your ICP. So who gets the most benefit rather than who pays the most. And then in the end, people are important because everything is related to it. Cool. Thank you for coming on. What is the best way for people to reach out to you if they want to get in contact with you?

[00:47:50.120] – Bridget

Linkedin. I’m just the Bridget Harris. I’m findable on LinkedIn, I think. I am on Twitter. I’m not the world’s biggest social media influencer, I have to say, but I am on Twitter and I think I’m on Instagram and TikTok. But I think LinkedIn is my favorite platform, or indeed, just email me. I’m Bridgett@youcanbook. Me.

[00:48:08.260] – Joran

Perfect. We’re going to add your LinkedIn profile. We’re going to add the bootstrapping manual. We’re going to add the traction book. So we’re going to make sure that you find all the relevant materials. We’re going to add a poll to the Spotify app, so make sure to respond to that because I’m always really curious to hear what people think about the episodes.Thank.

[00:48:25.100] – Bridget

You for coming on, Bridget.Thank you very much. It’s lovely to be on your show.

[00:48:28.360] – Joran

Thank you for watching this show of The of the Grow Your B2B SaaS podcast. You made it till the end, so I think we can assume you like this content. If you did, give us a thumbs up, subscribe to the channel. If you like this content, feel free to reach out if you want to sponsor the show. If you have a specific guest in mind, if you have a specific topic you want us to cover, reach out to me on LinkedIn. More than happy to take a look at it. If you want to know more about Reddit, feel free to reach out as well. But for now, have a great day and good luck growing your B2B SaaS.

Joran Hofman
Meet the author
Joran Hofman
Back in 2020 I was an affiliate for 80+ SaaS tools and I was generating an average of 30k in organic visits each month with my site. Due to the issues I experienced with the current affiliate management software tools, it never resulted in the passive income I was hoping for. Many clunky affiliate management tools lost me probably more than $20,000+ in affiliate revenue. So I decided to build my own software with a high focus on the affiliates, as in the end, they generate more money for SaaS companies.
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