How Bridget Harris Sold Bootstrapped YouCanBookMe at $5M to Capacity

Folks, I am grinning big today because we have a real treat. Over the next twenty five minutes, you're gonna learn the story of that grind, that twelve year bootstrap hustle from 0 to $5,000,000 of revenue competitive space from Bridget Harris, who cut her teeth in politics before launching YouCanBookMe about twelve years ago. They're they're about to make a announcement, which I'm not gonna steal the thunder from. They'll do it a second, but she

has now teamed up with David at capacity who's a seasoned entrepreneur, cut his own teeth teeth starting in 2011 at answers.com. One of the, we'll call it one of the fallouts of the 1999 heyday, but went public, went through a pipe, went through a take private, went through a majority, went through a secondary, ended up selling that business for about $809,100,000,000 bucks before launching Capacity, which is now focused on helping entrepreneurs enable and get their support

done quickly, providing great customer support, all leaning in to this AI revolution we're living in. On that note, David, Bridget, are you ready to take us to

the top?

Let's do it. Let's do it.

Alright. Well, David, first off, what's the announcement? What happened recently?

I am really excited to announce that Capacity has acquired YouCanBookMe. This brings world class online booking into our, collection of AI powered, platform pieces. And so one of the biggest use cases we've had for capacity is when folks want to automate their booking process. And now, we're able to do that on the tune of a million bookings a month.

That's incredible. Now, Bridget, I thought it would never happen. I'm going, there's no way. It's just this is never gonna happen. She's got profit sharing plans set up. You know, she's in full control. She's doing this with family members. This is great. Help us understand sort of, what what... Right before you guys signed the M and A deal and it closed, what did you grow revenue to, and what ultimately made capacity the right fit for YouCanBookMe?

So we had... We've got YouCanBookMe running at a really nice $5,000,000 a year, profitable, as you know well. You know, I've spoken a lot about creating profit, which you need to do if you're bootstrapped over long term. You need to start making money to make it worthwhile, frankly. So we've got to that stage. And, really, at the end of the day, I'm looking for how do I get YouCanBookMe to the next level?

How do I get this, you know, this business that we have built, which has has got to a point which is really exciting, really something that, you know, means something for our team, our company, but also our customers. How do we get it to the next level? And, actually, there's a combination of reasons why. And and, I should say at this stage, you know, we didn't go through a process. We weren't for sale. We didn't put

some some big estate sign, you know, up in our in our lot. Capacity approached us, and, we like... We really liked the offer. We liked we liked the fact that they're in customer support, an AI for customer support. It's a huge problem that needs to be solved. We know it. We feel it inside YouCanBookMe. So I knew that, you know, what they, are doing, what they're what they're building for their own customers is

a really strong product offer that we know our customers could really benefit from. There's a huge amount of synergy, as David was saying, that, all of those guys need scheduling, and, we need, you know, we we need to find a vehicle to scale and grow what we do. So there was a lot of synergy there. And I think also that the team itself and the way they approached us, it was really respectful of us being a

bootstrap company, of us having our own, you know, our own engine that we grow through product led growth and self serve. And there was something very kind of obvious about the deal. I mean, it's one of those things where as we got closer to the deal the day before we signed and everything else, it got easier and it got more exciting to look forward to the day that we were closing as opposed to harder. So I

suppose, you know, when you're selling away your life, you might, at the point of... About to sign, sit there and go, am I doing the right thing? You know? Is this a disaster? And, actually, genuinely... And there's a story to tell you about it, Nathan, but, genuinely, the night that we signed it, we were so happy that we just got to the point where we we know that this is the right thing to do for us.

And what night was that?

You were at a Paul McCartney concert that that night.

We told the lawyers on the day... It was it was just before Christmas. We told them on the day, we have to close today because we're gonna see Paul McCartney tonight. And no matter how important, you know, the capacity team are and the equipment with team and all the lawyers and how expensive it all is, Paul Paul McCartney is more important. And so we went off to see Paul McCartney in the o two. It was obviously

an amazing gig. And we were on a train on the way back from London to Bedford where I am now, And the whole thing happened over a call, you know, on our train back full of drunk people coming back from London. But it was... So it was a fantastic night for both weeks.

December what? December 22, twenty third, something like that?

Eighteenth. Eighteenth.

Yeah. December 18.

And then we've been in we've been in hibernation, Nathan, since then. We've been sort

of reeling from the shock. Yeah. No. It's great. Now before I jump more into the story, the backstory, the negotiations, you know, things to look out for both on on both sides, the acquirer and the one... The group being acquired. Bridget, is this... Are we pretty much on the spot here in terms of revenue growth or any corrections you wanna stick in here?

Yeah. No. No. We hit 1,000,000 sort of much more in the 2016, 2017 mark. So it's a bit it's a bit more sort of... It's it's less of a hockey stick and more of a of a of a nice a nice hill.

But about but about 5,000,000 at exit? Yeah. Yeah. Yeah. So, David, let me pivot over to you in capacity because you told me in our pre call you have a thesis. You built a list of 24 key items you think every company needs when they think about inbound and customer support. And you said, we're gonna go build or buy in all these spaces. Which of those 24 items led you to searching for booking tools and then ultimately led you to email Bridget?

Yes. So when we think about the 24 steps of the customer experience journey, we can kind of divide them into three buckets. You've got self-service. So that's where a consumer can get help, from an AI agent without having to talk with a person, without having to fill out a contact us form, without having to place a call to a human. That's where we started. That was kind of capacity's bread and butter. It's where we have a

lot of, product entry points in that part. What we realized as we got into it though, and that was kind of the original thesis of capacity when we launched back in early twenty seventeen. Big thing though that we realized is that no matter how good your AI system is, you have to be able to handle the questions the AI doesn't know how to answer. So the second big pillar that we focus on is this whole agent

assist concept. How do we help support teams do their best work when something does need to escalate up to a person? As we got into it, we started working with a lot of these support teams, particularly marketing and sales support teams. They're like, our biggest workflow is being able to get leads into our business, being able to book appointments, being able to bring people in. And so our third bucket are those kinds of campaigns and workflows.

We have other types of campaigns we do, SMS campaigns, voice dialer campaigns. We have multiple types of workflows we support, but scheduling is one of the biggest ones, that we've been handling for years starting internally and then going externally. And so we looked at this and said, wow, if we could find a company that's doing this well at scale, I think there's a great opportunity to combine our self-service AI and our agent assist tools together.

Mhmm. Bridget, I'm gonna keep asking David questions while I'm doing that, though. Can you open up your email inbox and search his email and and go... When you find it, read to me the subject line of the first email he sent you? Okay.

Nobody's asked me that, Nathan. You ask me so many unexpected questions.

Well, David, you know this. Like, right... I mean, someone like Bridget is busy. Right? So, like, you're sending out these emails to potential people to acquire, and you gotta get the response. You've gotta say it in a curious way that gets her to say, okay. I'm interested when she's, like, been all against her of exiting. Right? All against the VC world and just wants to bootstrap. What what was

That's true. And... Well, no. I... Well, I was gonna say the first time they contacted me, I said no. So there you go. Well, what what was your

email subject line was. But, David, what what do have? Okay, David, do you have a process? Did you only reach out to Bridget or did you reach out to 15 companies in the scheduling space?

Yeah, so the first thing we do is we use competitive research tools. I know a great one that has a lot of great stats around SaaS companies that you might be familiar with. So we use tools like GetLatka to go look at who Oh, nice. You know what? I gotta give the plug. Right?

No. I appreciate that. Thank you.

To go look and see where where people are at. And, you know what, every data point isn't always a 100% accurate, but it's directionally correct and enough for us to know, are we going to talk with someone who's at, 50 of ARR, someone who's at 50,000,000 of ARR, probably outside the range in either side of what we can go do. Let me make our list. And then I I will go through and look at each individual

website to see if there's anything amiss. And just just to make sure it looks like there's a heartbeat and a pulse there. Then we have a process where we send out a bunch of different types of reach outs, some by LinkedIn, some by email, occasionally we'll also do some calls. And the idea is it's like, hey, here's what we're doing. Founder led company sold my last company for north of 900,000,000. We're in this AI powered support

automation space. Would love to talk and see if there's any ways we can work together. And sometimes it might come out of that and it's like, not a good fit. Or sometimes it come out, I would love to acquire them, price isn't right. Sometimes we come out of a conversation, it's like, there could be a partnership there. And then every once in a while, we come out of a conversation like that, let's go turn over the

next cards. Doesn't mean that we're the right fit for them or they're the right fit for us, but there's a there there worth at least exploring and having that conversation.

And you've... Just to give you some credit while Bridget continues digging through her her, I'm sure very busy Gmail or inbox... Email inbox, I wanna make sure we get your story sort of plotted accurately as well. So based off our research, capacity has acquired, I feel like, six companies, including the the Lumen Box in in 2016. Is that right?

I think the total number is up to, I think, eight or nine at this point.

Eight or nine now. Okay. And do we we generally have your revenue profile accurate? You broke the 5,000,000 mark in 2019 and now we're at about $4,045,000,000, 50,000,000?

We're right at about 43,000,000 to end end last year. Correct.

Okay. Four... Okay. Great. Great. And is... Did I get the 5,000,000 right in 2019, or is that too early?

I had to go back and look at it. It sounds directionally correct. Somewhere

Okay. And where did you... You know, there's a lot of people listening right now that potentially wanna sell to a group like Capacity or wanna bootstrap like Bridge. There's also folks that wanna go start their own version of Capacity, maybe, like, with a search fund. Where did you get the initial capital to get going on this? You you weren't the original founder at answers.com, so I don't know how much you actually made when the company did

the secondary sale for $900,000,000, but where did you get the original capital?

Yeah. So I was the original founder of a company called Announce Media. We acquired answers.com. We did a international take private levered transaction for that. We had some private equity sponsors to help us there. So I did well in the answers.com exit. Didn't make as much money as the private equity guys did, but I I did well enough that I could use some of those proceeds toward future endeavors. And so when we started Capacity, our first

seed round was basically just insiders, my business partner and I, and then team members early on who wanted to invest.

And David, did you sell like most people in the seed round? Mean, you're selling 15% to 20% of the business. Were you in that same range?

Yeah. Somewhere in that range.

Okay. And was that the 1,600,000 in 2017?

That's correct. Yes.

Okay.

And then the idea was that we didn't wanna go take outside money until we had revenue customers and proven that we should exist. And then when we did that, we were able to have a much more sizable valuation in that next round. And, I wasn't pitching people an idea. I was pitching people a business. And so one thing your listeners who are super on the early stage, of their journey, my considers whatever you can do to

raise as least money as possible in order to get to that first dollar of revenue. I highly recommend that because you can keep more control, you can keep more, ownership and you don't have to give up the farm when you're still in the idea phase.

Mhmm. What did you pay though for LumenVox? I mean, was that a company you launched from scratch or you purchased? And if you purchased it, what was the total cash you had to pay to get that business under your belt?

Yeah. We we don't disclose the acquisition prices for deals partly because we've got a combination of cash, equity, seller notes, earn outs that we do. So we don't ever disclose what we pay for these things. But at a really high level, you can think of it as up through right around the pandemic time. We were a single channel web only customer support and employee support platform. So if you wanted to go automate support for team members

or customers, we could help you with When our biggest market at that time was in the mortgage space. And if you remember, mortgage was white hot, interest rates were free. And then pretty soon after Powell hit the brakes on, on the whole economy. And then we were on calls with clients that were getting fired in the middle of our calls. So we went from being 75% mortgage tech at that time to saying, okay,

we're gonna need to diversify the categories we're in. We need to go after... Because it wasn't our fault. Mortgage was a cyclical market. The second thing though is we need to we need to be able to go after the highest value highest value types of activities as possible which means we either need to get into a more expensive support which led us into voice, or we need to get tied back to revenue, which is why plugging

in with bookings and scheduling makes makes a ton of sense.

Mhmm.

So we went from single channel, web only, largely concentrated in one industry to saying we're gonna go and be diversified across industries, diversified across channels. And that means we're gonna need to support SMS and voice and social, and anywhere where you might get an email or a ticket or call.

Mhmm. I wanna go back to Bridget because I'm sure she's found the original conversation. Before I do that, though, David, just to sum up. So we talked about revenue and the number of acquisitions at capacity. You've raised... What's the total you raised to date for capacity?

It's just under 100,000,000.

Okay. And the last run was, I believe in October for 26,000,000 a series D?

Yes. Hesitated there. Extended that a little bit because we had some... We raised a little bit more on top of that, but yes.

Okay. And most people, once you get past series B, series C, you can get down to the point where you can negotiate, especially with your background and answers and you're only selling, call it maybe four or five, six, 7% of the business. Were you sort of in that range for the series D?

So the way that we think about it is we

looked at doing our capital raise in a totally different way than most other companies do. So most companies, you start out, maybe you have a seed round, then you go off and you go bring on a VC, then you're maybe trading one VC, early stage VC for a late stage VC. Sometimes you're going into a third, a third VC at that, at that point. And then you end up with this scenario where the founder is diluted.

The founder doesn't have board control. And then when they want to sell or buy or raise capital, they get squeezed. I've seen this store. It's like, it's like one of those,

Well, David, this is why I'm asking. I can just cut to the real question, which is how much equity of capacity do you still own?

I own just under a third.

Okay. And you still have board control?

I own a third of the of the equity, and I have my business partner and I have complete board control.

Okay. That's awesome. Great. Okay. Bridget, subject line. What was it?

Just on that last point though, Nathan, I mean... And this is kinda counterintuitive to every single corporate lawyer doing d and d. The fact that David and Chris have complete control of capacity was a plus point for me and Keith, not a negative. Because for us, we feel like we're we're whole... You know, handing over a Founder led company to a Founder led company, which is

really important for pushed on this because I'm going, has David actually gone through a series d and still kept more than, like, 10... I mean, most series d founders I interview, they have, like, 5% of the company left, 10% of the company left. So it's great that David and crew have done that. And, obviously, basically, you... It's way more aligned with how you think about business building too.

Yeah. That's it. I mean, the lawyer said, are you sure? They have complete control. It's like, well, we have complete control. So, you know, as long as you're comfortable with that. Do you want me to share my screen? Because I found it. It was on LinkedIn.

As long as David and you are both comfortable, of course. This is awesome.

Right. This is this is it. This is what I got in LinkedIn. This was in March. This was March 2024. I sold my last company for 960,000,000, Nathan, do you have to put that into your book? And started a new one, capacity to help automate support. We have around 2,000 clients across the globe. Given the overlap with what you're doing, I love to sync up repartnership or m and a opportunity up for a quick call, David.

And then, this is the best example advert for my tool. I just sent him my scheduler. Get him addicted plus one user.

Did he convert the paid account?

I think I think Marcus

capacity people move over to paid accounts pretty quick.

Yeah. Marcus upgraded. Okay. So the next the next call I had them with him was was a bit of a support call because, you know, Marcus upgraded. He wanted to ask a few questions. So, yeah, I mean, that was that was it. And that was in March. So there was there was some way to go. And, again, I wanted to emphasize for your audience that, you know, we weren't running a big process. We weren't sort of

trying to kind of get out at any cost. We we we sold because it was the right thing to... Because that approach, it didn't... We didn't sell in March, but it it started a relationship and a conversation that then led to another couple conversations in September, October that led to, you know, Paul McCartney Paul McCartney Day.

Yes. You you you tech... I went back and looked through our text, Bridget, and this is why I love doing what I do at Founderpath. Right? We're helping founders keep equity as they grow and hopefully make more when they exit. We did not have the privilege of backing Bridget, and YouCanBookMe with debt because she just didn't need it, and they were very happy, and it is what that is. But you did text me

October 7. You said, quote, I have an acquisition offer I'd love to chat with you through to get your advice. If you're in London, we could do face to face. And so, David, she was very good about holding back all the names and the details, but I do remember, Bridget, we had a really good brainstorm, and you were asking really good questions. I could tell you were seriously considering it because of the quality of questions you

were asking. When did, though, push come to shove? Right? When did the... No. David, to your point, there's the total deal price, and then there's the structure, and these are very different. Right? The total deal price could be 60... I'm making this up $50,000,000, but the structure could be 10,000,000 cash, 10,000,000 stock, 10,000,000 earn out, seller's notes, etcetera. When did the total just deal price, not the flavor of the deal, but the deal price, when did that really come out?

Yeah. I think the first thing that we did was just focus on, is this the right fit? And I I don't I don't wanna, like, jump past that because I'm a like both at individual level and at the company level. I've worked with brilliant... Like just a quick story. Worked with a brilliant product person at one point and he came from a larger organization and was an awesome fit for a large organization, but

couldn't multitask at a small scrappy startup. So wasn't, was a bad person or I was a bad boss. It just wasn't the right fit. And so when we, when we try to look at which companies we can go partner with, we need the people. And so part of it is like, we got to find people where, where there's a good mutual fit. If, if the company we're trying to acquire doesn't view us as being the right fit, there's no way it's culturally going to work.

And Bridget, how many people are you full time?

We're about 22 people full time. And we have, we actually have an overall headcount of around 35 people if you include all of our contractors and things.

Okay. So David, back to the people side. Yeah.

After you've determined, Hey, I think there's a good cultural fit here. I think we can work together. Then it's like, well, what are the, what are the, hot button items? We have some companies we've acquired where they had existing debt we had to go take on.

Have some Wait. Let's... We have a real example here. Let's try to use real... Wait. And what... Bridget, what were the hot button items in this deal?

So for us, the... It was... So if you'd asked me a couple of years ago, Nathan, if you and I had been talking about about us being acquired, I would have told you a 100% that I would have wanted to sell and walk away. I would have wanted a 100% cash on close, and I'm I'm, you know, I'm riding off into the sunset. Because I believe that that that that was the only way that made sense

for us to... I'm either running my company or I'm not, but I'm not gonna go in for some sort of hybrid deal. Now as we got to know David's offer and the... You know, he's obviously got a team as well that was working with us, and it it did evolve. We did go back and forth. There were certain things about, you know, exactly, you know, how much equity, how much cash, all the rest of it. But

at the end of the day, what I actually felt quite comfortable was was the fact that we're not riding off into the sunset. We're becoming investors in capacity. So it was really important to us that we like the team, that we like the founder, that we like, you know, as I said, I'm in I'm in favor of founder led companies. I'm in favor of founders having a 100% control. And for me, the hot button topic was

I didn't want to feel like we were selling YouCanBookMe, and we were... I don't know. That we were slinking away. Like, actually, idea that, like, oh, I don't I don't wanna do that anymore. I'm off. I actually wanted... I started to strongly feel that we needed continuity. I needed the story of YouCanBookMe in the company and the product and everything we've worked towards. There needed to be some continuity there that

I could be a part of that I liked. So, essentially, it was almost like... And we did feel a little bit like this on the day that... The day after close. All of us have felt like we've applied for a job to work for capacity. You know, we're all... We... We've all started to work for capacity now, and that needed to be as good and as important for me and Keith as anybody else. So I did...

So the alternatives for us would have been private equity. You know, all of these huge vehicles that come along and try to scoop up loads of SaaS companies at about our kind of level. And we all know their names. You know, they're absolutely massive. And for me, I think I'd always have felt like even if they'd given me double... If even if I'd got double double the amount, I'd all... I would always have felt like I

was walking away from something that I helped create that I think I'm very proud of. This way... And so I I never did it. We got offers. In fact, got offers... Over the last couple of years, we've had quite a few offers, but I never wanted to do it because I didn't want that feeling. And I think that the the point that I realized we could sell was actually... Was when we went to St. Louis in

Missouri where capacity is based, me and Keith flew out. So to try to reduce the amount of time for DD, we did a face to face, which I'd never done before, but I 100% recommend it. So me and Keith went to St. Louis. And on the first day we were there, obviously, everybody's a little bit trepidatious. I do my presentation. We meet David. We meet the team. They do their presentations. And everybody was so enthusiastic, and

there was so much energy. And we just wanted to crack on with scheduling and customers and support and what we're doing. Me and Keith went back to the hotel that night, we stared at each other. We're like... We just basically said this is on. This is on. You know? They they wanna sell to us. They wanna buy to... They wanna buy us, and we wanna sell to them. And I think there is... It's an

important thing.

Was in... When was that, David? That was in, October... End of October? That was

how old?

Because I Halloween.

It was Halloween.

Costumes the next day.

It was Halloween. It was Keith's birthday. Yeah.

Our UK friends with with

our David dressed up as a sheriff on the day. But it was Halloween. And and so that was what really clicked, that emotional feeling of, like, yeah, we can do this. This feels safe to do this. We like these people. We like this team. We like what... We like the joint plan. We like the vision. And what I've said to the team, it's like as we're the space shuttle docking on the International Space Station. You know,

the mission stays the same. We're still doing the same stuff, but we're basically joining a a a much larger, bigger operation so we can keep going with it. Mhmm.

Now put a put a cherry straw on top of this cake here. Share what you're comfortable sharing. My audience obviously loves numbers. Maybe I won't push you on a cash number, but, David, can you at least maybe share a revenue multiple you guys ended up trading at and getting the deal done at?

I would say we got to a number that was great for Bridget, great for us. We both feel good about it in both ways. Because you gotta remember, anytime we... It was a mix of cash and equity, but anytime we...

If you're not gonna give me the top line, like, multiple because my my audience will kill me if I don't get something from you, can I? You at least show the percentages of how it was split? So for example, 10% cash, 30% equity, you know, whatever whatever that... And then they can't do the math because we don't know what the total multiple is anyway.

Yeah. I mean, it's... Was it like a third

in Orgin, are you comfortable with this?

I don't mind. The... These... But these are David's numbers. If... I know the number, David, you want me to... I know the split. So it's fifty fifty, 50 cash, 50 equity. And that's what we were happy with.

We we were happy with And did you start there with that initial offer, or did did you have to work to get to that?

We we negotiated. There was quite a few different terms that we negotiated, but I wanna say this is really important is that we were able to take a really generous amount of equity that we're really super happy with. A, because it feels like we're we're fully invested the success of YouCanBookMe Inside capacity, but also because we're bootstrapped. So for me and Keith, as founders, we could take a, a hybrid offer much more easily

than so many people who, as David says, take on far too much complicated cap table nonsense at the very beginning. And I highly recommend it because as founders, as bootstrap founders, we were able to do a deal that exactly... When we got our number, Nathan, we got exactly what we wanted. We're really happy. But at the same time, we've actually now got this new relationship with Capacity and David, which makes it even better than what we were doing before.

Yeah. The the last thing I just kinda leave us with, because I know we're hitting time, is, Nathan, from our perspective, whenever we work with a company like YouCanBookMe, What if the company isn't convinced that capacities equity is going to be worth X plus Y in the future, then we're probably not the right fit. We want everybody incentivized to be able to say, Hey, look, we want to build something together. And that means, yeah, you

should get compensated for what you built and have a good outcome. But we really like aligning the incentives where we're building something together. And the combination of these companies is much bigger and brighter than either one of them stand alone.

Yep. Well, guys, I wanna be respectful of everybody's time for the sake of my audience just to run down the story. We don't know what the total sort of top line multiple was, but let's say it was something very conservative, like two x on 5,000,000. That'd be a 10,000,000 deal price. And if it was 50% cash, that's 5,000,000 cash to a bootstrapper. Right? A bootstrapper team and bridge it. Right? And then 50% equity can go for

the ride after that. That's really what you wanna build. Right? You look how happy she is. She has full control. She had no board. She had to convince it was her and Keith in Halloween costumes presenting in Saint Louis, Missouri to get the deal done before or after a Paul McCartney concert. David, Bridget, thank you so much for the details. Thanks for taking us to the top, and congratulations.

Thank you. Very much, Nathan. Thank you. Yeah.

Alright. Boom. We will cut. Guys, what'd you think?

Yeah. Great. It's good? You are good, Nathan. So tell us what you... So so I know you've gotta

jump