Capacity Acquires $5m ARR Bootstrapped YouCanBookMe To Build AI Support Mega Platform
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Folks, I am grinning big today because we have a real treat. Over the next 25 minutes, you're going to learn the story of that grind, that 12-year bootstrap hustle from zero to five million bucks of revenue competitive space from Bridget Harris, who cut her teeth in politics before launching You Can Book Me about 12 years ago. They're about to make an announcement, which I'm not going to steal the thunder from. They'll do it in a second. But she has now teamed up with David at Capacity, who's a seasoned entrepreneur, a

cut its own 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 800, 900 million 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. All right. Well, David, first off, what's the announcement? What happened recently?

I am really excited to announce that Capacity has acquired You Can Book Me. 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 going to happen. She's got a profit sharing plan 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&A deal and it closed. What did you grow revenue to and what ultimately made capacity the right fit for You Can Book Me?

So we had, we'd got You Can Book Me running at a really nice $5 million 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 You Can Book Me to the next level? How do I get this, you know, this business that we have built, which is

has got to a point which is really exciting, really something that 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 I should say at this stage, we didn't go through a process. We weren't for sale. We didn't put up some big estate sign up in our lot.

capacity approached us. And we really liked the offer. We liked the fact that they're in customer support and AI for customer support. It's a huge problem that needs to be solved. We know it. We feel it inside You Can Book Me. So I knew that what they are doing, 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 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 engine that we grow through product-led growth and self-serve. And there was something very kind of obvious about the deal. I mean...

As 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 know that this is the right thing to do for us

And what night was that? You were at a Paul McCartney concert that night. We told the lawyers on the day, it was just before Christmas, we told them on the day, we have to close today because we're going to see Paul McCartney tonight. And no matter how important the capacity team are and you can book me team and all the lawyers and how expensive it all is, Paul McCartney

is more important. And so we went off to see Paul McCartney in the O2. 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 reasons. So December, what, December 22nd, 23rd, something like that? 18th. 18th, December 18th. And then we've been in, we've been in hibernation, Nathan, since then. We've been sort of wheeling from the shop. Yeah.

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 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 want to stick in here? Yeah, no, no. We hit 1 million, so much more in the 2016, 2017 mark. So it's a bit, it's a bit more sort of, it's less of a hockey stick and more of a nice hill. But about 5 million 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, quote, we're going to go build or buy in all of these spaces. Which of those 24 items led you to searching for booking tools and then ultimately led you to email Bridgette?

Yeah, 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 spread 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 2017. A 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, David, our biggest workflow is...

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 kind 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 here.

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. Bridget, I'm going to keep asking David questions while I'm doing that, though. Can you open up your email inbox and search his email 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, because David, you know this, right? I mean, someone like Bridget is busy, right? So you're sending out these emails to potential people to acquire and you've got to get the response. You've got to say it in a curious way that gets her to say, okay, I'm interested when she's been all against sort of exiting, right? All against the VC world and just wants to bootstrap.

What was it? Well, no, I was going to say the first time they contacted me, I said no. So there you go. But that was months ago. I'm curious to know what the subject line was. Okay, I'm going to find out. 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 GetLodka to go look at who... Oh, nice. I got to give the plug, right? No, I appreciate that. Thank you. To go look and see where people are at. And you know what? Every data point isn't always 100% accurate, but it's directionally correct and enough for us to know, are we going to talk with someone who's at 50K of ARR, someone who's at 50 million of ARR, probably outside the range on either side of what we can go do.

Then we make our list and then I will go through and look at each individual website to see if there's anything amiss. And 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 million. 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, eh, not a good fit. Or sometimes it comes 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, like let's go turn over the next cards. Doesn't mean that we're the right fit for them or they're right fit for us, but there's a, they're there worth at least exploring and having that conversation.

And you've just to give you some credit while Bridget continues digging through her, I'm sure, very busy Gmail inbox or inbox email inbox. I want to 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 taste, including the Lumen box 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 generally have your revenue profile accurate? You broke the 5 million mark in 2019 and now we're at about 40, 45 million, 50 million? We're right at about 43 million to end last year. Correct. Okay. Okay. Great. Great. And did I get the 5 million right in 2019 or is that too early? Yeah.

I have to go back and look at it. It sounds directionally correct. Okay. And where did you, you know, there's a lot of people listening right now that potentially want to sell to a group like Capacity or want to bootstrap like Bridget. There's also folks that want to 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 weren't the original founder at Answers.com. So I don't know how much you actually made when the company did the, you know, the secondary sale for 900 million bucks. 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 an 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 did well enough that I could use some of those proceeds toward future endeavors. And so when we started Capacity...

We, 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? I mean, you're selling 15 to 20% of the business. Were you in that same range? Yeah, somewhere in that, somewhere in that range. Okay. And how was that the 1.6 round in 27 million in 2017? Uh, that's correct. Yes. Okay. And then the idea was that we didn't want to go take outside money until we had, uh,

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. Yeah.

And so one thing your listeners who are super on the early stage of their journey might consider is 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. What did you pay though for Lumenbox? 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 don't disclose the acquisition prices for deals, partly because we've got a combination of cash, equity, seller notes, earnouts 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 business.

customer support and employee support platform. So if you wanted to go automate support for team members or customers, we could help you with that. 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 going to need to diversify the categories we're in. We need to go after, because it wasn't our fault. Mortgage was a cyclical market. Second thing though, is we need to be able to go after the 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 a ton of sense. So we went from single channel, web only, largely concentrated in one industry, to saying we're going to go and be diversified across industries, diversified across channels, and that means we're going to need to support SMS and voice and social,

and anywhere where you might get an email or a ticket or call. I want to go back to Bridget because I'm sure she's found the original conversations. Before I do that, though, David, just to sum up. So we talked about revenue and the number of acquisitions, that capacity you've raised. What's the total you raised to date for capacity? Just under 100 million. Okay. And the last run was, I believe, in October for 26 million, a Series D? Yes. You hesitated there. We got 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 4%, 5%, 6%, 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 look at...

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 VC 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 story. It's like one of those... Well, David, this is what 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 equity and I have my business partner. 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 kind of counterintuitive to every single corporate lawyer doing D&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 handing over a founder-led company to a founder-led company, which is really important to us. This is why I 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, it gives you way more line 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. Yes, as long as David and you are both comfortable, of course, this is awesome. Yeah.

Right. 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 million, Nathan, so 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'd love to sync up, re-partnership or M&A opportunity up for a quick call, David.

And then this is the best example I've ever heard from my tool. I just sent him my scheduler. Get him addicted. Plus one user. Did he convert to a paid account? I think Marcus... Yeah, Marcus upgraded.

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

get out at any cost. We sold because it was the right thing, because that approach, we didn't sell in March, but it started a relationship and a conversation that then led to another couple of conversations in September, October that led to Paul McCartney Day. Yes. I went back and looked through our text, Bridget, and this is why I love doing what I do at FounderPath. We're helping founders keep equity as they grow and hopefully make more when they exit. We did not have the privilege of

of backing Bridget and you can book me 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 7th. 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 now, 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. Fifty million bucks. But the structure could be

10 million cash, 10 million stock, 10 million earn out, seller's notes, etc. 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 don't want to like, jump past that because I'm like, both at the individual level and at the company level, like I've worked with brilliant, like, just 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 it wasn't he was a bad person or I was a bad boss. It just wasn't the right fit. And so when we tried 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 there's a good mutual fit. And 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 how many people are you full time?

We're about 22 people full time. And 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. After you've determined, hey, I think there's a good cultural fit here. I think we can work together. Then it's like, okay, well, what are the hot button items? We have some companies we've acquired where they had existing debt we had to go take on. Wait, we have a real example here. Let's try to use real. Bridget, what were the hot button items in this deal?

So for us, the... It was actually... So...

If you'd asked me a couple of years ago, Nathan, if you and I had been talking about as being acquired, I would have told you 100% that I would have wanted to sell and walk away. I would have wanted 100% cash on close and I'm riding off into the sunset because I believe 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 going to go in for some sort of hybrid deal. Now, as we got to know David's offer and he's obviously got a team as well that was working with us,

And it did evolve. We did go back and forth. There were certain things about exactly 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 favor of founder-led companies. I'm in favor of founders having 100% control. And for me, the hot button topic was, I didn't want to feel...

Like we were selling You Can Book Me and we were, I don't know, that we were slinking away. Like actually this idea that like, oh, I don't want to do that anymore. I'm off. I actually wanted, I started to strongly think

feel that we needed continuity. I needed the story of You Can Book Me and 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 after close. All of us have felt like we've applied for a job to work for capacity.

You know, 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 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, even if I'd got double the amount, 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 never did it. We got offers. In fact, we 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 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 and we stared at each other. We just basically said, this is on. This is on. They want to sell to us. They want to buy us and we want to sell to them. And I think it's an emotional feeling. And when was that trip?

That was in, when was that, David? That was in October, end of October. It was Halloween. Halloween. It was Halloween. It was Halloween. It was Keith's birthday. They're off our UK friends with Halloween. That's right. David dressed up as a sheriff on the day. Yeah.

But it was Halloween. 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 the joint plan. We like the vision. And what I've said to the team, it's like 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 much larger, bigger operation so we can keep going with it.

Now put a, put a cherry scroll 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, uh,

Great for Bridget. Great for us. We both feel good about it in both ways. Because you got to remember, it was a mix of cash and equity. But anytime we... If you're not going to give me the top line multiple, because my audience will kill me if I don't get something from you, can you at least show the percentages of how it was split? So for example, 10% cash, 30% equity, whatever, whatever. 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...

Virgin, are you comfortable with this? I don't mind. But these are David's numbers. I know the number, David, if you want me to. I know the split. So it's 50-50, 50 cash, 50 equity. And that's what we were happy with. And did you start there? Was that the initial offer? Or did you have to work to get to that?

We negotiated. There was quite a few different terms that we negotiated. But I want to 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 fully invested in the success of You Can Book Me Inside capacity, but also because we're bootstrapped.

So for me and Keith, as founders, we could take 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 last thing I just kind of leave us with, because I know we're hitting time, is Nathan, from our perspective, whenever we work with a company like You Can Book Me, what...

If the company isn't convinced that Capacity's 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 standalone. Yeah. Well, guys, I want to 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 2X on 5 million. That'd be a 10 million deal price. And if it was 50% cash,

That's 5 million cash to a bootstrapper, right? A bootstrapper team and Bridget, right? And then 50% equity that can go for the ride after that. That's really what you want to build, right? 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 St. 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. Thanks very much, Nathan. Thank you.