How YouCanBook.me Reached $5M ARR and 20,000 Customers While Staying Bootstrapped and Profitable (Interview with CEO Bridget Harris)

Opening and Introductions

Nathan Latka

00:00No fire, no chairs

Bridget Harris

00:02>> No chairs.

Nathan Latka

00:03No no fireside chat.

Bridget Harris

00:04>> Yeah. But great intro.

00:06We're gonna

00:06>> have to

00:06>> do it, Alex.

Nathan Latka

00:07Great intro. Standing up.

Bridget Harris

00:08>> Standing fireside chat.

Nathan Latka

00:09Stand up fireside sit down chat.

Bridget Harris

00:12>> As ever thanks everybody for Friday afternoon sticking with us here. Excited to be on stage.

Nathan Latka

00:18We have Bridget Harris.

Bridget's Background and the Five Lessons Framework

Bridget Harris

00:20>> Bridget Yeah. Fastest note today, we've got to give Bridget a round of applause here. She made it to number 30 in the e two e, female 100 fastest growing, I I guess Entrepreneurs

Nathan Latka

00:33female entrepreneurs in

Bridget Harris

00:34>> The UK. So well done to

Nathan Latka

00:35well done to Just

Bridget Harris

00:38>> giving her a bit of credibility, due credibility as to the the subject here, five lessons in bootstrapping to 5,000,000 ARRs. Do we have many bootstrappers here? I think there's a lot of bootstrappers at this conference. I'm gonna say probably about a third of you. So we're two bootstrappers, we can talk about that. I'm at 5,000,000, but not in ARR in dollars. You're at 5,000,000 ARR dollars or pounds?

Nathan Latka

01:02Dollars, but we're kind of heading towards the pounds depending on the dollar sterling parity, you know, it kind of changes, but yeah.

Bridget Harris

01:09>> Yeah. And I'll be running SAS stock, which, helps SAS companies get to 10,000,000 in revenue throughout conferences, on memberships and media. Bridget running an actual SAS company, so I think more, pearls of wisdom coming from Bridget, today in the next twenty minutes than, than myself. But let's talk about it. Five lessons. We've got seventeen minutes, plus we want to take some questions, as well. So first lesson, is around timing. So, like, who Timing. Who, what, when

Lesson 1: Timing and Choosing to Bootstrap

Bridget Harris

01:40>> to to buy your product.

Nathan Latka

01:42Right. Well, yeah, the question about timing is intrinsically connected to whether you raise money. Because if you're gonna go for a kind of product that requires a lot of upfront investment to do with compliance or maybe it's it's got some hardware association, you've got to some manufacturing, or you need to do a huge amount of customer research in order to get the right thing, then your timing is going to be really affected by your choice to

02:05bootstrap.

Bridget Harris

02:06>> Should we take a second?

02:07>> Cheers. Here we go.

Nathan Latka

02:08You see? Thank you.

Bridget Harris

02:09>> You see how effective bootstrappers are at getting what we want. So we can we could do any stage, but we can also eventually, things that you need arrive.

02:17>> We could do what we want because we own the company.

Nathan Latka

02:19Exactly. So this is what I would say. Like, my experience of bootstrapping, and I I wanna hear what you think about your timing for for because you were much more in the you need upfront capital, so I wanna know how you did it. Mhmm. It just so happens that with our products, we were doing online scheduling. It's a drip drip. It's a self-service. It's a freemium. So because of that and also we started about fifteen years

YouCanBook.me's 20,000 Customers and Viral Growth

Nathan Latka

02:40ago. The timing for us to be able to stretch that out over a long time when you're really earning very little. Now for context, to get that 5,000,000, we have over 20,000 customers. So we have a lot of small people, small engines, small amounts of money powering what we're doing. So it takes a long time to build that up. So if you haven't got the time to do it, then that's really helping you to find whether

03:04you can bootstrap or not. But what about you, Alex?

Bridget Harris

03:06>> Yeah. I think for me, I mean, SaaS Doc was a side hustle, obviously, before it was a revenue generating business. I spent twelve months building an audience inadvertently, maybe a bit more sort of credit around that, but twelve months doing that, I think six months of those twelve months I was working full time somewhere else, working from home, so I had the time to work on the side project. And after twelve months of not being revenue

03:35>> generating, I had an audience that I could then sell tickets and sponsorship into, so we were then customer funded after the next twelve months.

Nathan Latka

03:44Yeah. I mean, it it if you if you can't afford a potential five year runway to get up to speed where you're hiring people, you're paying yourself, and you're feeling good about it, then that's the point to take on a financial partner who's gonna give you some of that upfront cash. But right now, you know, the the first the first product that myself and Keith actually launched, my cofounder and CTO, was literally in 2003, and it

04:07was a survey building tool. It's called tickboxer.com that we sold the domain since then. And it's exactly like SurveyMonkey, but we've just realized in order to get people to use our survey building tool, we needed a lot of upfront capital to invest in the marketing and the awareness and the brand. We couldn't do it because we didn't wanna take on money, and it's as simple as that. We we we we dumped the the product. So as

Early Product History and Finding the Right Model

Nathan Latka

04:30soon as we got youcanbookme where we could see that natural viral growth rate essentially, and we had the patience and timing to do it.

Bridget Harris

04:38>> Second lesson is around skills. What skills that you have as the cofounders versus what do you need to pay for them Absolutely. To the business.

Lesson 2: Skills and What Cofounders Must Cover

Nathan Latka

04:47So, again, it's the same sort of thing when you're choosing to bootstrap versus upfront funding. If you have the money, you can buy all the skills. Fantastic. If you haven't got the money, you then gotta look at your internally, what skills have you got? And my view is that you've got three core things that you need inside, a product a SaaS product like ours. You need engineering, CTO, somebody who's actually gonna code. You need operations and

05:13finance, somebody who's basically gonna deliver the business strategy, and then you need some kind of creative designer, product owner, somebody who's going to sort of shape that product over time. Basically, me and Keith had the had the first two. So he was the engineer, and I was the operations person. And you see that today ten years later in the in the company. It's a very engineering and operations led company. It's taken a while for us to

05:36move across into more product and design led sort of set of priorities. So you can get a lot of people, but I don't I've never met somebody yet who's one person who's all three or two founders. You either get three cofounders with those skills or you have to buy in. Now I would say, actually, nowadays, it's probably easiest to buy in tech, ironically, engineering because there's so many fantastic agencies that do it. As long as you've

06:02got a very good strong product desire, you can basically hire people to to do that for you. But, again, can you bootstrap without one of those key leading skills? How are you gonna pay for that skill? And whatever you can't pay for, you're gonna create debt. So, essentially, you're gonna create technical debt or customer debt or product debt or some some form of cash debt. How are you gonna do it? So cash debt is borrowing money

06:28from a from a from an investor to, or any kind of borrowing money, that's cash debt. If you decide not to take cash debt because you want to be customer funded, well, then you're gonna probably take on debt by one of the other pillars.

Lesson 3: Hiring, Culture, and Paying People

Bridget Harris

06:43>> So let's talk about hiring then. So obviously we talk about the skills, what have you got, what do you need to buy for pay to bring into the company. So when you're hiring, know, I guess kind of like what stage do you know like, what sort of roles and how much you're gonna pay to to bring?

Nathan Latka

07:02I mean, point, and I was talking about it with Andy today. So it's huge. Everybody makes mistakes. Loved what Becca was saying about hiring and how to essentially diversify and think about internationally who you can get. There's some incredible models out there now of people who've just decided to not employ anybody directly, and they just go straight to the freelance market and only get freelancers. And they put a, you know, gum road is is based based

07:25on that model.

07:27And actually, Angie, this is really what I was trying to capture in what we were talking about earlier today. The minute you start hiring and employing people, you're introducing culture into your company. So you have to decide what that culture is going to be and how that's gonna grow. So what you pay them and how you how much you can afford is is is absolutely embedded and baked into it. So my view is pay as much

07:49as you can, a sort of sort of minimal acceptable offer for people. Don't pay them the most you can. As soon as you realize that they're gonna offer you value and they're gonna keep helping you build your company, keep paying them internally to keep incentivizing and supporting the people internally who work for you and also to stay market relevant. But you've gotta do it within your bootstrapped boundaries. And don't do and I we have done this

08:16before. Believe that if you could just afford to pay somebody a 150,000 a year and you sort of bring in some kind of 6 figure superstar, that they will then have this trans transformative effect. I've never experienced that. I've never experienced the idea that by going out and paying, you know, huge salary, I'm gonna get a 10 x person to come in. All my 10 x, if you like, people who work for me now who are

08:39on good salaries, they all started joining the company of fairly modest rates and basically worked really hard inside the company to get to that point where I realized just how powerful a team we are because of it. But you you have to do that through culture, not just not just direct hiring.

Bridget Harris

08:55>> Yeah. I think I mean, slightly the opposite for us. I mean again we're not a SaaS company, but I feel like we over the years and you know we've been running for eight years as a bootstrap business, we haven't really been able to pay like you know competitive, super competitive sort of wages, and we probably not I wouldn't say underpaid, we pay well for all the industry that we're in.

Nathan Latka

09:21I'm not applying for a job by

Bridget Harris

09:22>> the way.

Nathan Latka

09:23Yeah, no, no, no, no.

Bridget Harris

09:24>> Fine. It's okay.

Nathan Latka

09:25But yeah I think only sort of like recently you know in the eighth year are we now paying top dollar for senior leadership roles, and we are seeing personally like a 10x difference in I guess these expensive sort of folks. But is that that's a disadvantage for bootstrappers generally, would you say?

09:46So you absolutely. And I think in some ways, you just have to be kind of confident about what it is that you're offering somebody, and it's not the case that every single high performing person wants exactly the same thing. It's relative to all these other other things in their lives. So, you know, you can find people who they actively like. You know, youcanbookme's brand, if you like, as a company is pretty clear. I think it'd be

10:13pretty clear to anybody who wants to come and work for us what they're gonna get. They're gonna get a small company because we basically you know, we we have we have kept a lot of control over the size of our company deliberately, pretty much to reduce the sort of stress on us as founders. I mean, look at Becca. She's running a company with a 150 people, and she's, you know, she's dressing up as a unicorn. Like,

Remote Work, Profit Share, and Company Values

Nathan Latka

10:36there's a kind of you know, you have to find find your strategies through, and and, I personally would find it very stressful to to run a company with a thousand people. So there's that. So we're small. We're remote. Another big differentiator, well, not so much now, but a big differentiator, is to be remote. We're bootstrapped. We're profitable. We pay out profit share. We are very transparent inside the company, and we did we document all of that.

10:59So we do it very deliberately so that somebody, the aim is for somebody to look at our website and go, ah, those look like my people. I want to go work for those people. Now when you when you get to that situation, you then really want to be able to say, what we offer is fair. It might be above market rate. You might also get some extra in terms of bonus and profit share. It's a package.

11:17And so I don't know if any of you were watching me last year in Austin. Hands up anybody was that was the right. Hi. Of course. Hi, everybody. But that, you know, I was talking then about profit share. So you end up introducing other parts of your company that you can incentivize people to be a part of. Also, don't underestimate the power of the offer to say you have an opportunity to really change something here. You

11:40can come in. Here is here is here is the way we've laid it out. Because we've been bootstrapped, we're not under any pressure to kind of deliver to an external person's criteria. We can build something that we really want. So one of our internal cultures culture statements is commitment to excellence. So that's that sometimes does mean we're gonna rewrite something or we're gonna drop it because it's not good enough. And, you know, we have a we

12:03have a quality control that matters to us. We're not just move fast, break things, hack it, move on. It doesn't matter. Let the customer down. Let's go. Let's go. Let's go. We don't do that. And there's some people where they know they've got an opportunity to make a real impact, and that is just as important as their as their salary.

Lesson 4: Cash Is King and Financial Literacy

Bridget Harris

12:21>> Lesson number four is cash is king. What does that mean in, I guess, the bootstrapping terms in your experience?

Nathan Latka

12:26Cash is king. I mean, my god. If there was anything, that anything anybody that doubted that after last weekend's SVB meltdown, you know, they won't now you it's it's all and, actually, as a bootstrapper and we had money in Silicon Valley Bank, I was I was indignant about the idea that my money that we had earned from customers, customer money basically, hard earned customer money was in a bank account that was potentially going to be lost

12:57or taken away or gone towards some kind of loss. I was apoplectic about that. So you can't run out of money if you're a bootstrapper. So we didn't raise cash, but we did borrow money. We borrow we have we we got banking overdrafts and credit cards, private loans. We we did it. You have to watch how much money is in your bank account. It doesn't really matter much how much profit you're making, how much you're earning.

13:19You just can't run out of money. I've never ever not made payroll for the twelve years we've been running the company, and there's only one way to do that, which is financial literacy. So one of the early things that I did when I realized that we were bootstrapping for real, if you like, with people, as soon as you take on people, you're responsible for their financial security as well as your own, your company's. I went on

13:41a financial literacy course. I basically learned about how profit and loss works, how balance sheet works, how working capital works. So I run my business. It's a business. It isn't it's not necessarily a SaaS company or anything else. It's a you know, you're the same. I mean, your your overheads must be absolutely enormous in terms of being an event organizer. So I can't imagine. You know, our gross margins are very, very good because they're a it's

14:03a software company, so it's it's pretty simple to run. But you've got to be you've got to be confident about what you're talking about.

Bridget Harris

14:09>> One of the you you mentioned actually sort of earlier that a book that you read whilst you're bootstrapping that's helped you was venture deals.

Reading Venture Deals and Understanding VC Incentives

Nathan Latka

14:16That's right. Why why was that? So again, I would say to any founder who's thinking about being, you know, bootstrapping sounds sounds hard, maybe maybe great long term, but it sounds hard. Maybe maybe venture capital or taking on investment is easier. I would just say that's fine. That's completely legitimate, but you've got to be educated around the table. If you're gonna take money from a VC, and I read about ten years ago, Venture Deals, whenever it

14:38came out, read that book because, it will tell you exactly how deals are structured, what the incentive of the VC is, and what business that they're in. And it's a really great business. It's a legitimate business, but it's not necessarily got anything to do with what you've decided to sell as a product. So you just have to educate yourself about what venture capital and corporate finance is about, and they're not your friends. You know, what they're

15:00doing is they're making money from your decision to go into business as an entrepreneur and make money, And that's a different thing. And you my view would oh, sorry. My view would be, you know, exploit them if you need them. If you need them for upfront capital, if you need them for upfront investment, exploit them because that's what they're for. But don't think that they're doing you a favor, and the only way you're gonna learn that

15:20is by reading the books. And that's a great book.

15:23We've got two minutes. The final lesson was around boundaries, so separating your personal boundaries from your business boundaries.

Bridget Harris

15:29>> Yes.

Nathan Latka

15:30Can you share a bit more around that?

15:31Well, that again is a reflection of what happens if you're bootstrapped. You don't have this external pressure, which is obviously a good one. Because if you've got you've just taken on £10,000,000 from somebody, they're obviously gonna be hovering around making sure you're not gonna spend that on sweets. So you've got this accountability for your business business that puts you into a different role. Whereas if you're bootstrapped, you can say, well, I don't know if it's my

Lesson 5: Personal and Business Boundaries

Nathan Latka

15:52expense card or if it's the company expense card. Does it really matter? It's my money. You can you end up falling into patterns potentially around twenty four hour adopt, you know, obsession with your business. And I just think it's gonna take you longer to bootstrap a company. So you're you're you're signing up for ten, fifteen, twenty years of your life. If you don't put in boundaries soon enough, you you know, it could you'll burn out like

16:17anybody else. There's nothing special about bootstrapping. So my experience is I've always bootstrapped. However, whatever pennies we had, whatever peanuts we had in our bank account for youcanbookme, it was always separate financially separate to my personal expenses. And that way, it just gave me some mental clarity about what I was doing.

Bridget Harris

16:36>> Awesome. Any questions from the audience in the time that we have left? Anything for Bridget?

16:43>> To them. On the right first.

Nathan Latka

16:47We use youcanbooking, great product. Yeah.

16:53I'm just impressed as well. We're similarly sort of, you know, largely bootstrapped, not entirely bootstrapped SaaS. Sometimes the growth is slower than you would like. Yeah. And then you see other competitors in your fields who are well funded and growing very quickly. I'm just curious. Do you ever feel pressure from, like, the Calendlys of the world or whomever else?

Audience Q and A: Competing with Calendly

Nathan Latka

17:13Well, obviously, sometimes, you know, you get when you're a business owner, you you're you never lose that kind of fear that something is all just gonna go wrong and and, you know, you you've gotta take care of it. At the same time, you have to be philosophical. Like, apart from anything else, the perspective, we were in business before Calendly. We've we've been in scheduling for a very long time, and we our goals are different because we're

17:34bootstrapped. So I don't need to be a £200,000,000 company in order for actually everybody who works for us and our customers to be super happy. So, you know, I'm glad to see obviously, Dingus and Sazir are here in the room as well. Your money that's in our bank account that was in SVB that we're protecting here, like, my relationship is to you guys. It isn't to anybody else. If Calendly comes and, or any other scheduling tool,

17:55Chili Piper were here like those guys there. They're absolutely fantastic. You know, we're all in the same business to try to serve customers. And our primary relationship is with the customers who currently buy us, and then our marketing and growth opportunities to try to persuade others. And you just have to be self assured, I think. You I don't you can't go into business and be an entrepreneur and be worried that your idea is is not good

Staying Focused on Customers Over Competitors

Nathan Latka

18:17enough or somebody's gonna take take it away from you. You have to basically be a bit of a you know, like, basically be a bit cocky. It's just like, well, I think we could probably do anything if we wanted to. You know, you just have to go in there and say, yeah. They're great, and they've been well funded, and they're doing whatever they wanna do. Why is that why is that got anything to do with my

18:33ability to ship tomorrow and do the customer feature that somebody wants and to basically run a successful business and and have lots of money in the bank and and keep everybody happy? Like, they don't they don't have to affect me. And I think you that that's another way of grounding, you know, being sort of strong boundaries. I would say that resistance to pressure from competitors is a strong boundary. That doesn't mean to say you don't pay

18:56attention, but you do need a boundary. I think maybe one more.

19:02Yep. It's a quick one.

19:03What what was the name of the book that you mentioned everyone should go to the table, the VC table understanding?

19:09Oh, Bunch of Deals. By who's the guy that wrote it?

Bridget Harris

19:11>> Brad Feld.

Nathan Latka

19:12Brad Feld. Bunch of Deals. I mean, it just it kinda lifts the lid on it. It and it's actually I had a lovely chat with a guy. I don't know if he's here, Jim, who's a venture he's a growth equity guy. He was he's a he's a guy, you know, turning up to these events specifically to try to attract companies to invest in. He said, listen. VCs try to give you too much money because they're basically

19:33trying to run down the fund. They're trying to write big checks. If they tell you they're gonna give you a million, they're gonna try to make you take 5,000,000 because they're just basically you know, their their objectives are different to yours. He said, bootstrap for longer. Don't take as much money. Work out what you're trying to do first. You know, work work out how you're gonna make money from customers before you take money from VCs. Because

Book Recommendation and VC Advice

Nathan Latka

19:52often in this world, people announce funding rounds as if they've just made some money. It's like, no. You haven't. You've just either sold a bit of your company or your customers become your VC, or you've now just, you know, entered into some enormous debt structure and finance structure where if if if you were under pressure, you might have to pay that VC back three times whatever they've given you before anybody else gets a penny. And I

20:14think you just have to be literate about that because it is it is a perfectly legitimate form of finance. Obviously, Founderpath are here as well and all these other guys that are doing some incredible work to give I mean, if I'd had honestly, if I'd had Founderpath I'm not just saying this because it's Nathan's show, but if I'd had Founderpath ten years ago, I was scraping around for £25,000 from NatWest, you know, like on the high

20:34street of Bedford. And they were like, oh, I'm not quite sure. I'm like, I'm growing at 2000%. You know, but I just don't understand you're making a loss. I know, but you need to give me money. And it was just such a headache. But I I can believe that if Founderpath had been around ten years ago, I'd have just you know, I would absolutely have floated in, got a million, off we go. But, you know, but

20:56I want but I mean, I'm not gonna give away my company, you know, to people who sort of feel like or in the when they circle around in that first year, and they and they and they give you those sort of preference shares and the liquidation preferences and all the rest of it. And you read you read up on it in venture deals, and you suddenly realize the game they're playing. Good luck to them. Well done.

21:15But don't forget, it's not your business. It's their business model. It's not your business model. So I'm actually quite evangelical about this, I realize. I wasn't gonna slag them all off, but, like, you know you know what I'm saying.

Bridget Harris

21:27>> Cool. Alright. I think we're done. Let's hear it for Bridget.

Nathan Latka

21:31Thank you. Thank you, Alex. Okay.