Bridget Harris on bootstrapping your startup

What can busking teach us about bootstrapping a startup? If you ask Bridget Harris, the two experiences aren't so different.

Bridget, who in a previous life could be found busking in London’s Covent Garden and in tube stations, is the co-founder and CEO of You Can Book Me. It’s a SaaS tool for quick and easy online scheduling that she launched with her husband in 2010. Today, has $1-million in ARR, turns a profit and has more than 10,000 customers – including the likes of Atlassian, Box, Indeed and Shopify. And against conventional startup wisdom, Bridget and her team made this happen without taking any VC funding.

My chat with Bridget covers bootstrapping your way to profitability, why VC interests may not always align with the founders’, how her busking days shaped the way she runs a startup, and more. If you like what you hear, check out more episodes of our podcast. You can subscribe on iTunes or grab the RSS feed.

What follows is a lightly edited transcript of the interview, but if you’re short on time, here are four key takeaways:

  • VC interests – bringing in a growth target that will deliver valuations and a timely payout – won’t always align with a founder’s own business interests. But if you opt to bootstrap, success still requires exposure to external ideas.
  • Products that solve big problems are a great fit for VC funding; problems that can be solved incrementally through agile and lean principles can make bootstrapping work.
  • A successful remote team needs a culture built on high quality work, productivity and collaboration. There are a lot of great tools for the latter, but Bridget doesn’t believe internal email is one. In fact, she’s banned it.
  • Founders who bootstrap must have a keen understanding of risk, ability to adapt and a trust in where they’re headed – a lesson Bridget picked up in her busking days.

John Collins: Our guest today is Bridget Harris, co-founder and CEO of, a simple SaaS tool for hassle-free scheduling. Welcome, Bridget. You launched back in 2010. What was the origin story there? What were you doing beforehand and why did you choose this problem to solve?

Bridget Harris: We actually have another web application that also does a form of scheduling, When is Good. That was one of the first web apps that we built and the problem it solves is how to find a time to meet for a group of people. We built this very simple interface; everybody fills out their times and you send the link around and then by magic the system will tell you what date or hour everyone can make. Then what we found was that people were trying to stab away at that golden spot and secure it and say, “Well that’s the slot I want to book.” We found that by building essentially a backend integration with Google Calendar people could do that, they could select the slot and then book it into their calendars.

Very quickly the booking side of the tool took off as a freemium. When is Good was a freemium model, so we knew very much how often people upgraded and how willing they were to upgrade. Really the answer was they’re not that willing to upgrade on a tool that essentially organizes what people perceive to be something that they could also do by email. They don’t really want to spend a lot of money on a tool helping them, even if they love using it. Whereas with, because it was mainly businesses using it, they immediately wanted to pay., which started off as a little sister of When is Good, fast became our main focus and what we’ve been building on ever since.

John: You were kind enough to be on our panel in London last year when we did our world tour. Since then you’ve focused very much on what businesses your market is.

Bridget: Definitely. One of the things that we have learned about scheduling – and this is a more broader point about trying to find a good problem to solve – is that scheduling is a different thing to different people. You have businesses who want to schedule in their customers because that’s the hour or the day they are providing a service and they’re working, so they are photographers or gardeners or beauty therapists or trainers or people who are providing usually face to face services. There’s a whole element of e-commerce associated with that and a lot of support to the customer, the end booker themselves they want follow up on.

Inside Intercom London – Startup Panel

Bridget, center-left, speaking on the startup panel at Inside Intercom London.

It’s small to medium businesses and it’s a huge, huge market but it’s pretty tough to get into because as soon as you realize you’ve got the right tool for beauty therapists you’ve got the wrong tool for photographers, for example. A lot of companies that started to use in the early days, I have to confess, we had not quite anticipated it. It was the sort of thing which naturally grew because people could see that the value of Google Calendar, they were using it to book in client meetings, so recruitment, sales, customer success, etc. A lot of companies now will use and indeed other tools to sort that problem out. People are booking demos or they’re booking support calls using our tool.

Another interesting use case of, which again took off very naturally in America because a lot of schools had adopted Google for education, is that schools will use us for parent-teacher conferences where they can spool out hundreds of calendars for each teacher to handle 10 minute slots. We actually have a very strong education and nonprofit dimension to our tool as well.

Opting for a bootstrapped approach

John: An interesting aspect of your business is that you decided not to take VC funding along the way. What attracted you to that different route these days, given that venture capitalists seem to be looking for a lot of good homes for money?

Bridget: We would never say never and we’ve never been closed to conversations, but on the other hand it wasn’t an “either or” when we set out. The CTO and developer of is Keith, my husband, so the two of us have formed a partnership over the years of building these products. and When is Good weren’t the first products that we built. Previously we had a survey building tool, which was completely different. We were working on digital products and various kinds of web applications for a long time before we knew we were building a business or indeed we actually had a successful product on our hand. emerged out of a lot of experience building products. Then once we’d built the product, could see it was working, had that famous product/market fit and people are paying us for it, we had to figure out how we’re actually going to make money. We started to build a company around the fact that we could make money and we could be profitable. Now we’ve got more than $1million ARR and we’re profitable. We’ve taken a long view about how to build from an idea to a product through to making money. Along the way the VC intervention might have helped – I’m not saying that there’s not companies that haven’t been hugely helped by taking on investment – but for us it always felt like the wrong moment for a number of reasons.

John: One of the benefits of venture capital I’ve seen, even at Intercom, is that it opens up this network of people. Your VCs can connect you with other people in their portfolios, companies who’ve been through similar problems. As someone who’s bootstrapped, do you ever find that’s a challenge, getting those sources of guidance or that network that can help you?

Bridget: There’s certainly a risk that if you’re bootstrapped and you’re small then you can become quite insular. Keith and I are more at risk because we’re a married couple. You can get very personal, very insular and in some ways the one direction you could go in is what they call a lifestyle business where you’re not really interested in talking to anybody else and you just want to build something that is going to work for you and you’re not referencing the outside world.

I deliberately tried to protect us from an insular perspective, so you do what everybody does, you read loads of books. Once you’ve got past some advice and business case studies, which are around companies that did go down a course of rounds of funding, all business advice really comes down to the same basic principle: how are you going to make money and how are you not going to fall over? You read all of those books, you follow the blogs, you go to conferences, you reach out to people. As I said, I’ve been very open – when VCs have contacted me I always chat to them. It’s always good to get their perspective and to see if the conversation is going to go anywhere.

VC’s advice is not always going to be the best advice for your business.

We do have some longstanding advisors who have seen us through over the years, many a time when me and Keith have wondered what on earth we’re doing. When you find yourself trying to explain how you’ve decided to solve a problem to somebody else who you trust and admire and you realize that you sound a bit ridiculous, you think oh, I better figure that out. We’re always, always learning. We’ve hired lots of people who have come with them lots of experience of working with other companies. We’re very open that we need to learn as a company and as a team about how to grow and not take anything for granted. The fact that we don’t have the external board of investors doesn’t mean we’re not open to external ideas.

There is some skepticism sometimes about the advice that VCs are going to give you because their interests are not necessarily aligned to your interests. Their interests are often about bringing in a growth target that is going to deliver valuations and a payout for them within the timetable of their fund. They’re very open about that, it’s not like that’s a secret, but the fact is it might not necessarily be aligned with what you could achieve in your business separately. Put it a different way, VC’s advice is not always going to be the best advice for your business. Your interest in running your business isn’t always in the interests of what VCs are trying to achieve.

Solving problems incrementally

John: We hear a lot of people talking these days about side projects as a way to test ideas while you’ve still got the day job. It sounds like you and Keith were doing that way back before people in Silicon Valley had embraced the idea. Basically you got to try a number of different models and make your mistakes before you bet everything on

Bridget: Absolutely. We had two or three web applications that we built and we always had an ambition to build a web application that was going to be successful, that people were going to use and people were going to give us money for. We were motivated by building a product that was going to make money. Obviously you do that by adding value to people’s lives, you solve their problems. You identify problems and you solve them in a way that you think is going to be interesting, unique and attractive. Then people will give you money for it. That’s what we always set out to do, and we did certainly have times when we realized that our technology wasn’t appropriate. When we built the survey building tool it was just before a whole load of the client-side technologies came out, so ours was very, very clunky and it wasn’t swishy-swashy, it wasn’t drag and drop like Wufoo forms.

We spent a lot of time on those agile and lean principles of learning from customers.

You just start to think this problem that we’ve chosen is just too big to bite off. If you pick a problem which is too big for you to solve by yourself, then of course you need to reach out and work with a team of people and have some financial backing – if you’re absolutely sure you can solve it. Whereas when we got into When is Good and then, those were problems that we realized we could put on a slow burn. We could solve them incrementally and we spent a lot of time on those agile and lean principles of learning from customers and adapting the tool based on their feedback.

Certainly in the last couple of years, we’ve moved towards quite a big turnover but also been profitable and hired quite a few people. What we’re interested in now and what we’re doing now is very different to what we were doing two or three years ago.

Assembling a remote workforce

John: You’ve spoken a lot about hiring, and what’s interesting is you’re hiring remotely. You’re based just outside London, so you say to yourself it might be hard to attract people to work just outside London, but then you’ve turned to remote hiring as a strength of the company.

Bridget: That definitely emerged as a result of our experience of running the company and running the product and deciding what we needed to do, which happened at a much slower pace than if we’d taken on VC. If we’d taken on VC three or four years ago, we probably would have hired a whole load of people and expected them to come and work for us in Bedford and got an office and done all of that, or maybe moved to London. You do the playbook, you do what’s expected and because we didn’t follow that course, as we started to hire people it became obvious that there’s plenty of talent around the world who want to work for a company like ours and we could attract them in on other measures like the technology, the product, the kind of things that we’re trying to achieve.

As a result of that we’ve got a couple of people in the US, we’ve got two people in Spain, we have somebody in Germany and quite a few people in the UK. Everybody is spread about and then we come together face to face probably sometimes two or three times a year depending on what we need to do. We built up that remote company very naturally alongside the way we’ve hired people in. Once you know what kind of company you’re building, you then start looking for the people who you know are going to fit into that culture.

John: One of the things about hiring people remotely is they have to manage themselves. It’s maybe harder to mentor them. Does that preclude certain types of people? Is it harder to bring on, say, more junior people when you’re doing it remotely?

Bridget: Definitely and there is no real answer to this. I’ve heard from quite a few companies that work remotely that if you want to bring on an intern or a trainee or a young engineer or somebody who needs more support, it is very difficult to do that over the internet. The consequence is that we don’t do that very much. We’ve had a few interns and young people working for us in Bedford and that works, but it’s sporadic. It’s not something that we’ve invested in.

It’s a problem I’d quite like to crack because I don’t think that what we’re doing at the moment is going to continue to be super unusual; It’s actually a very pragmatic way of attracting high quality people who want to work for you around the world. It’s not necessarily a cost saving thing; it’s not something to do with trying to buy cheap labor in. We employ everybody directly so we’re set up as employers in the UK, in Spain and in the US and in Ireland. We directly employ people and we give them all of the benefits of working for a company full time.

That is something which more and more companies will see there’s a benefit to, not least because the price of office rentals in places like London are just sky high, but also going back to your earlier point about managing people. It’s incumbent on us to build a company where we have a culture of expectation of high (quality) work, productivity and collaboration, which doesn’t rely on you eyeballing people every day and glaring at them and making them work. That should not be the instrument by which we are successful, we should be successful because people are motivated when they work for us to do their jobs.

John: Do you think it’s more a technology problem that needs to be cracked, i.e. VR, or is it more cultural and social issues that people just aren’t used to remote working and at the moment it’s only certain kind of people that are willing to take the plunge or are willing to organize themselves that way?

Bridget: The tools are all there. My God, if we wanted to start using VR that would be pretty crazy, but we could. But there’s plenty of fairly invasive tools. There’s some tools where everybody’s got a webcam and you can just click on the link and you can get a screenshot of everybody at their desk at any given point. You could have open channels through webcams all the time if you wanted to eyeball people. We have a default transparency in the company, which lots of companies like Buffer and others have advocated, and I really believe in it.

If you have that kind of belief that as a company and as founders we can encourage everybody to be open, honest and collaborative about what we’re trying to achieve, i.e. not hierarchical or trying to hide information in order to promote yourself or your own interests against somebody else’s, instead everybody takes the shared credit. If that’s part of your culture and then also transparency is part of the way you communicate, then remote working should naturally fit in with that, because we want to share stuff on our chat channels and online share documents. We use video a lot when we’re having meetings. Everything is naturally defaulted to sharing with people, so therefore it really doesn’t matter.

You need to
be open and happy to communicate.

In fact, sometimes it can be a bit of a hassle if everybody’s in the same office. We get very quiet and it’s a bit weird and we actually stop communicating, because everybody’s in the office nobody shares anything on chat. Then we start to lose touch, ironically. We use face-to-face stuff with our team for much more about social engagement and brainstorming and where you want to get team bonding, but day-to-day collaboration, it actually works better if you were using the tools. You need to be a good communicator – you need to be open and happy to communicate.

John: You mentioned a number of tools there: chat, shared files, video. I noticed you didn’t mention email. I understand you’ve banned email as an internal communication tool at Why?

Bridget: When anybody starts I send them an email to say “Look, this is how we communicate, this is our culture, these are our priorities, and by the way, don’t email us.” It’s not necessarily a ban; it’s more we encourage and essentially incentivize use of all these other tools. Nobody would think to send anybody an email because it’s a very spur type of communication. Obviously any of us that have externally facing jobs use email. I only use email with colleagues when we’re emailing them about an HR matter, something that’s personal and confidential. That’s probably a good indication of what email is good for, which is when it’s got to be one to one, personal and secure and confidential, use email.

John: We’ve got to the stage where they are like digital letters.

Bridget: Exactly. First of all, reply all drives me crazy because if you’re stuck on a reply-all list, you can’t stop people from spamming you. There’s also a bit of a passive aggressive thing that crept up, which is the bcc line. If I bcc somebody, and even if I’m sending an external email, what I’ve noticed, which is good practice, is if somebody starts off on an email thread and you want them to know that you replied but you don’t want to spam them, you bcc them and you tell everybody you’ve bcc’d this person. In office environments, when you start being bcc’d into things, people are creating secret communication channels, which can be quite toxic. We’re a young company and none of us want to work for big corporate organizations. We’ve all worked in those and we all know that it can become toxic, so we just choose not to go there.

John: Speaking of toxic, what increased role does culture play when you’re a remote company?

Bridget: It’s a basket of what I’ve just said before, which is transparency, openness, the way we’re building the product and we’re choosing to interact with our customers, and how we’re managing things. All of that attracts a certain type of person who wants to work for us. Going back to being bootstrapped, we have very open conversations with everybody in the company about how we make money, how much everybody gets paid, what the prospects of the company are, and hopefully as the company continues to be successful and profitable, those profits can go back into people’s pockets.

We have a jam today philosophy and people buy into that. It’s different to offering the usual share options or that structural benefit of being part of a big company. Some people have worked for us and they realize that a small company doesn’t work out for them. They don’t work out where you’re in a very small fishbowl with 10 other people. Others have really thrived and love their jobs. One of the best things about my job is when spontaneously some people on HipChat will start congratulating themselves about how much they really like their jobs.

It’s not something that Keith and I really expected to do when we set out. When we were building we were building a product that we wanted to sell to people. Three, four years later we’ve now built a company that people work for and we’re having a much bigger conversation with the world about it. The culture inside does come from me and Keith originally, but also the way we have discussed with the people who joined us about how they want to continue to build as a company, because as we grow and hire more people we need to be pretty sure and articulate about what it is.

For example, many companies have a culture deck. We have a set of slides with bullet points covering things that we aspire to, the way we like communicating, the way we like solving problems and the things that we can default to when we’re uncertain. I think when you come across something, especially in an HR situation where you realize something didn’t go the way you were happy with, you’ve got a document to refer to to say look, this is how we are, this is how we want to be and that wasn’t consistent. Or this is not going to work out.

What busking can teach us about bootstrapping

John: You had some interesting other career paths before you got into software, particularly when you busked music in Covent Garden. What did that era of your life teach you about running a startup?

Bridget: My goodness, that early entrepreneurial spirit in retrospect definitely taught me a lot about the way I see my role now. It was a lot of fun. I talked about this earlier in one of my conference presentations, because I hadn’t realized there was such a strong analogy. I (busked for the first time) when I was 14 as a way to make money and my first pitch was in Victoria Station in London. When you put your case down – I play the fiddle – you put the case down and you start playing. You’ve got absolutely no idea if somebody’s going to give you money or not.

You’ve decided to produce a service for somebody, playing a tune as they walk along. The first time somebody put money into my case it was just the best feeling that I had pleased somebody and that they were prepared to pay for it. After that you realize you do need to have confidence. It’s quite nerve racking to start playing in public, and 25 years ago when I was busking it was a lot more scrappy than it is now. Now they have formalized pitches but when I was playing you would just walk along and find an open space in the tube system and start playing. Then you would have pitches for an hour and other buskers would come along. You learn a lot to deal with people and essentially hold your own when you’re in difficulties.

Bridget Harris’ Buskers Guide to Startups BoS2016 from IoT Forum

The longer term analogy is that the biggest thing I’ve learned about running a business is that you really have to understand risk. There’s a lot of rhetoric about business visionaries and leaders and “what’s the magic dust to do with Richard Branson” or why do people do this in the first place. My own take on it is that you need to have a very good idea of what risk you are taking, how you define that risk and what happens if your gamble doesn’t pay off, and you have to face the consequences of disaster, for example.

Having that ability to not exactly know where you’re going and trust an outcome that you’re hoping is going to work based on your own hard work, it’s a good toolkit. When I was busking, it was the same kind of thing. I still play now. I play in an Irish session band in my local pub. You’re sitting there and you’re listening to other people and you don’t know what tunes you’re about to play and then somebody else leads into something else. You start playing that and then you start learning new tunes. It’s a performance, but it’s a performance that has an edge to it because you don’t exactly know what’s going to happen. As a musician I’m very comfortable with that kind of music.

That’s how I’ve basically run the company as well, since I took over in 2012. I became the CEO to run the company because the company needed leadership and as I’ve learned along the way, it’s been using those kind of busking skills; you hustle sometimes, but you have to be able to play, your tunes have to sound good, I suppose.

Learning from the mistakes of Westminster

John: Before you were heavily involved in politics, most recently serving as an advisor to the Deputy Prime Minister in the UK. You did have some, critical things to say about politics and Westminster when you left that world, but anything you think people in software can learn from it?

Bridget: I’ve been thinking about this question, because there’s a lot that Westminster could learn about software. As I said, Keith and I had been working together for a long time. Literally for 15 years we’ve been working together on digital projects. I knew I was already keen on tech and on the potential for tech a long time before I got this job as a special advisor. I had run, in parallel to working with Keith, I had a whole load of other political jobs as well, working in parliament.

I came to that job knowing full well how in the last bastion of old fashioned methods that happens in Westminster, but what could software learn from Westminster? Learn from all of their mistakes, that’s the only thing they can learn. Very little in the current political systems in not just the UK but in many countries, is serving the people. There’s all sorts of evils to do with the technology as well, but technology is democratic, it can give power to people, it can be judged, it can be disrupted, it can be challenged and it can be harnessed.

It’s an amazing opportunity for growth and good things to happen in society, whereas Westminster and Whitehall really trudge along within very, very old fashioned methods and ideologies around holding close information away from people, trying to basically produce the best outcome from the least number of people involved in a decision. Which is kind of the antithesis to how software works. I really couldn’t say much more. Software can just look at that system and take it on, disrupt it.

John: What’s next for, what are you hoping to disrupt this year?

Bridget: We are really happy with our growth, because at times it has been very uncertain whether things are going to take off. It’s a very exciting year for us because as I said, we’re now fully in the world of being a profitable business and having a mature team now. We’re always reinvesting and re-engineering and supporting our tools a bit. It gets better for the people who love it and want to use it. Then we just want to grow more into those markets, into those companies who are discovering that the old fashioned email way of dealing with appointments is just starting to die and as people realize and they get experience booking appointments, they know it’s available and then they start asking for it, and more and more companies want to use it.

There’s not just us, there’s quite a few other really great competitors out there who are doing similar things to us and so essentially for us it’s like game on. We can take them on and we can take on the group of companies there that aren’t currently using us and pushing the case for online scheduling and having fun along the way.

John: Best of luck with it, Bridget, and as usual, a pleasure chatting to you.

Bridget: Thanks so much, John. Cheers.