How Acuity Scheduling grew 5X in 3 years (and was acquired by Squarespace)

Joining me is someone who was a Mixergy listener and whose software runs our entire booking process for guests.

I love what he built for so many reasons but about a year ago I read that he sold it to Squarespace! He bootstrapped the company so I want to find out his motivations for exiting.

I asked him to come back to the podcast to tell me how he grew since the last time we talked, how the sale went down, and how his life has changed after the sale.

Gavin Zuchlinski

Gavin Zuchlinski

Acuity Scheduling

Gavin Zuchlinski is the founder of Acuity Scheduling, online appointment scheduling software.


Full Interview Transcript

Andrew: Hey there, freedom fighters. I am so excited about today’s interview. My name is Andrew Warner. I’m the founder of Mixergy, where I interview entrepreneurs about how they built their businesses. Joining me is someone who listened to Mixergy interviews and more personally to me, his software interacts with every single one of my freaking guests. A long time ago I realized I had a hard time booking guests on Mixergy, not just with me, but we have two producers here. At times, we’ve even had three producers here. And I needed an easy way for a guest who said yes to get on a call with a producer. And often they don’t even want to schedule a call with a producer because what’s an extra step for? They just want the attention. They just want the link. But I need them to talk to a producer so that we can get some information about them, prepare them, and prepare ourselves for them.

And then I need them to schedule with me. And again, at times, that’s a little bit of an extra step for them. I needed to make it super simple. So I signed up for this software, Acuity Scheduling, happened to be created by somebody who listened to why interviews. And what I liked about it, loved actually, was I could put in all of our producers’ availability into a calendar, let them all have their own quirks, and then let the guest pick from all of their calendars in one spot. And then, if there was a problem, like a guest forgot to show up to do an interview with me or to a pre-interview, we automatically would go back into Acuity software and create, like, a reminder email or adjust the process. And it’s such a set it and forget it system that I sometimes forget that I use Acuity Scheduling to book all my guests. Well, about a year ago, April 2019, right?

Gavin: Mm-hmm.

Andrew: I was reading in the news that Gavin Zuchlinski, the founder of Acuity Scheduling had sold his company to Squarespace. And I said, “What? The guy didn’t take funding, he has no reason for an exit. And what is Squarespace, the company that helps you build websites, have to do with scheduling?” So I said congratulations to him. For some reason we celebrate internally even though I’ve got no stake, no skin in the game, but I don’t know why. I think Gavin’s just a likable person. So we celebrated, like we had, like, a stake in it.

And then I waited and I finally said, “Hey, Gavin, it might be time. Can you come back and do an interview and tell me how the sale went down, how you grew the business since our last interview, where you talked about how you launched the business, talk about how you grew it, and then a little bit about how life changed after the sale?” So he agreed to do it. First, he ran it by Squarespace’s, which has got to be a different feeling for you, right, Gavin?

Gavin: Oh yeah. There’s a lot more moving pieces right now.

Andrew: Yeah. I had to, like . . . I said, “Gavin, do you want to do the interview?” He said yes. And I said, “Let me check.” And then I talked to Squarespace and they said, “Yeah, sure. Go ahead, Andrew.” So this interview where we find out about how he built his business, why Squarespace bought it, how the sale happened, how life had changed since the sale and so much more, it’s sponsored by two phenomenal sponsors. The first is a company that Gavin and I both use to hire developers. It’s called Toptal. And the second, if you have a team of people, writers, and other people on your team that you want to all communicate in the same way, I’m going to tell you about a company whose name you’re probably going to forget until you realize, “Oh, I need them.” It’s called Qordoba, but I’ll talk about those later. First, Gavin, welcome.

Gavin: Thank you for having me on here. It’s really fun to be back and to reminisce about everything again. This is my first interview since the acquisition.

Andrew: I’m so psyched. How much did you sell for?

Gavin: That I can’t share.

Andrew: I kind of knew you weren’t going to share it. We talked about it before, but I thought it was important to ask. Do you remember the day that the sale happened? I will ask you about revenue, by the way. But do you remember the day that the sale happened or is there a memorable moment when life changed?

Gavin: Oh my gosh. It’s such a long process to go through an acquisition. And really, like, the very first moment when Squarespace approached me about it, it was back in, gosh, like, September 2018. I was in New York City. I came into the Squarespace’s offices. They obviously don’t tell you, “Hey, we’re going to approach you about an acquisition.” They just happened to set up a meeting with, you know, the CFO, the CEO, and their brand new corp dev person. So you see the guests listed and you kind of know that something interesting will happen. We had a partnership for a couple of years beforehand. And superficially, it was about seeing how that partnership had gone.

So I met with them, which is just such an incredible experience. Like, the culture here was amazing. And I get along exceptionally well with Anthony, the founder of Squarespace. They approached me about the acquisition, just saying, “Hey, would you be interested in talking more? What sort of numbers are we looking at here?” It was phenomenally fun. I went back to my wife. We celebrated that night. I had some wine. The very next day, I happened to have a meeting set up with a private equity firm about potentially doing a secondary round for Acuity for de-risking. That went exceptionally well.

They were fantastic people too. And then the following day, found out that my wife was pregnant. It was like a whirlwind of all of these crazy things. And then it turned out, went into Squarespace the very next day and said, “I am very interested in the acquisition. Absolutely love you all. But tiny little thing, there’s going to be a time limit on this. We’ve got about nine months to figure everything out and close, hopefully less than that so we can actually onboard and be successful. And I want to make sure that I am there for my family and that my quality of life too.” And they were exceptionally receptive and so warm to that.

And that was one of the things that, not just like the initial honeymoon period, but starting to know like there’s something bigger happening and to see how they react to it too, and not just thinking about the numbers, but the people behind it. That ended up making me very fulfilled and knew that I was going along the right path. But that was just the beginning.

Andrew: How long did it take from that first conversation to closing?

Gavin: Oh my gosh, way too long. So first conversation in September, we had a quiet couple of weeks. It’s kind of nerve-wracking. You get very excited about it, and then you start talking numbers, and then they just go silent. And I wonder like, “Wow, are you actually . . . ? Did you just, you know, try to stir me up? Were you just trying to get some company internals as we, like, solidify this? Like, are you actually going to just build your own scheduler and you were stringing me along?” But no, then they came, it was the very first acquisition. Things were moving a little bit slower. Yeah. And it went from September all the way until April. We had lots of ups and downs along the way. Things took so much longer than expected.

Andrew: So about nine months?

Gavin: Yeah, we went up to, like, the very end right there. That what was . . .

Andrew: So the day after or . . . ?

Gavin: I don’t recommend doing that.

Andrew: Soon after you closed the deal, you ended up with the baby and taking paternity leave.

Gavin: Yeah, yeah, yeah. I was like, thankfully my wife was a couple of weeks late. That actually made it a little bit better. But yeah. And then I ended up taking a four weeks of paternity leave and completely unplugging while we were trying to figure out how to integrate the products. And yeah, everything went incredibly smoothly.

Andrew: You know, I’ve got a note here from the last time that you were on where you said that you would only disclose that you had a mid-seven figures revenue business. A lot of people wonder how I get guests to be so open about their numbers because I respect the boundaries, but within the boundaries, I feel like there’s something that we could learn. So where were you at the time of the sale compared to that?

Gavin: Oh gosh, I can’t share exact numbers, but we’re about five times bigger. We had been doubling every year at a minimum for a while. And then with scale, that slows down a little bit. But yeah, the business is still growing steadily. And that was one of the interesting things you touched on in the introduction too was that Acuity was growing quickly and actually quite profitable. When we did the sale, we had around 50 employees and exceptional. I think we had about a 40% net profit margin at the time too, which was very nice. So we had the capital to keep growing on our own and we had a good, sizable base of users and good momentum going into it too.

Andrew: I should say that interview happened in 2016 so that’s phenomenal growth for that period of time. 2016 is when we did the interview. 2019 is when you sold, so you’re talking about 5X in that period of time?

Gavin: Oh yeah.

Andrew: You know what? One of the things that I was wondering about and I didn’t know how you would take it, but you said you’d be open to talking about it. Calendly, when I first discovered Acuity, you were basically the only game in town. And then I started noticing people using Calendly, a competitive product for free. It had stripped down features, easier to use, nice design. I wondered if like, maybe that’s why you sold. Maybe you guys were starting to be overtaken by people who are going free. You’re laughing at that. You weren’t?

Gavin: No. Yeah, Calendly is an exceptional product. I think that they did a great job. Just in general, when we started out, there was, I don’t know, one or two other products that were extremely bloated, difficult to use, not really . . .

Andrew: By the way, I’m hearing some banging as we’re talking, just like the clicking. I don’t know what it is, but I hear it right now.

Gavin: I’m sorry about that. Yeah. I’ll stop smiling. I think it’s my headset whenever I smile.

Andrew: Oh, you can’t stop smiling.

Gavin: I know. So, anyway, yeah, with Calendly, I think that they hit a different end of the market mostly because of all of the bundled products that we started seeing. We started seeing scheduling start to be bundled with many different things.

Andrew: Like HubSpot would start to be include it.

Gavin: Yeah. Like HubSpot . . .

Andrew: Pipedrive, I think even has it. The CRM, if not Pipedrive, then other contact management software has it.

Gavin: Yes, CRM and then we see it too. Like, we’re having to kind of the healthcare area and there’s a lot of tools where you track patient records. They also have scheduling. It’s very poor quality, but the poor quality bundled with the other things is really good. And especially if it’s just very easy to get started, that’s what a lot of people need.

And Acuity, we used to be the smaller, easy to use one and we’ve been . . . But because of just the incredible amount of competitors out there, prior to the sale to Squarespace, we were starting to move up market as a strategic move, adding in more features to support larger businesses. And our focus shifted from just anybody who needed to schedule an appointment to more and more focusing on businesses whose day to day really revolved around appointments. And if they’re not scheduling appointments, they’re not making money.

It allowed us to, you know, start to include features where it was an incredibly detailed thing, something like that that we introduced just with minimizing gaps in the calendar where when you enable this setting, you can make sure that appointments are back to back and your schedule is optimally stacked, and you can have larger gaps. So if you say, travel to an office, you can make sure that you travel to the office, you have all of your appointments back to back, and you have a large enough break, that you’re actually able to go away and do errands in between your next batch of appointments afterwards.

Andrew: You know what? I didn’t know that was a feature because that does frustrate me. I from time to time, will say to anyone in my audience, “If you want to talk to me, like, I’m available.” I’ll give them a link. And I might have one person in the morning, another person come in at, like, 11:00, another person come in at 4:00, and I’m basically in the office all day waiting for these appointments when I’d rather . . . They don’t care. They just want talk. I’d rather have them at 10:00, 10:30, 11:00. And you’re saying you automatically will do that?

Gavin: Yeah. Go to availability, schedule in the limits and then you can choose to minimize gaps . . .

Andrew: Doing that right now.

Gavin: . . . and you can choose the amount . . . If you want to allow any gaps in your day two, you can choose how big to make them too. Yeah. Yeah. But features like that on the lower end of the market, when you only get a couple of appointments per week, much less valuable. It’s the intense people like you who like really revolve around appointments that we were starting to go after. And I think that Calendly had a great fit in the market where they did an exceptional job. They had a very good free product too, but mostly for folks whose day revolved a little bit less around appointments too. And that way we could go after businesses too, which is of . . .

Andrew: How? How did you know that that was it? I was kind of thinking when you said we started to focus that you were going to say, “You know what? I’m going to focus on massage therapists,” like your mom, who inspired the creation of the software when she needed a way to schedule appointments or I thought you were going to say, “I focused on salespeople.” Basically, I thought you were going to go with a job title, instead you said, this broader group of people who, some of them might be massage therapists, some of them might be salespeople, but what they really all have in common is they need a packed schedule. Their work is their schedule. How do you figure that out?

Gavin: It’s interesting that you mentioned vertical because it seems like people jump to vertical as the automatic categorization for businesses when Acuity had been cross-vertical for so long. And we find vertical is the wrong categorization for businesses, that within a specific vertical, there’s more similarity between people at different behavioral levels like a solo massage therapist who might, you know, travel to different sites is much more similar to maybe a car repair person than they are to a massage therapist who is in a spa with five other people, and rooms, and everything else, where that spa might be much more similar to a Pilate studio too. So we found behavioral categorization was much more accurate and it allowed us to be much more cross-vertical, increasing our overall TAM.

Andrew: How did you know that? You’re right. We always do think about verticals. What’s the one group of people, you speak their language, you talk to them, you go to their conferences? How did you know to go beyond it and then how did you find those people?

Gavin: That’s a great question. Really just intuition because I think the advantage was, Acuity took so long to get started. It started around 2006. It was just myself. I was doing all of the customer support. I was doing all of the development. And thanks to that time, I absolutely love doing customer support. But because of doing that, which I recommend every founder do, like wait, if you can, to outsource that because it’s such a valuable source of insight. It connected me a lot closer to the customers too. And then over time too, we found just the most likely people to churn out of Acuity, the biggest reason for churn is that people just aren’t getting people booking with them. And generally, the reason they’re not getting people to book with them is that they don’t have clients.

So we really wanted to get people who Acuity is a good fit for them and those people with clients. And then as we started to dig into there, we found that there’s a higher willingness to pay if you have more appointments. You see a lot more value out of it. Our value metric is generally calendars, the number of staff that you have and the pricing of Acuity goes up with there. So, if you have a lot more appointments, it’s very nominal cost for us to support more appointments, and you see significant more value, and you’re more likely to stick, we’re able to add more features to support you in that business in a much deeper way. And as we move into that area, we’re able to differentiate a lot more and still maintain a very large market.

Andrew: So, when you said that they churned, that they canceled because they didn’t have enough bookings, you don’t mean because they couldn’t use the software to get enough bookings. You mean they just didn’t have enough customers?

Gavin: Exactly.

Andrew: They had maybe five customers a week and that’s not your sweet spot. That’s where you realized, instead of trying to figure out how to tell them to get more customers, how to make it easier for them, how to go lower price for them to keep them going, you said, “They’re not us.” I even saw your eyebrows rise, as I said lower price to make it reasonable for them. That’s not you.

Gavin: When we shifted to that strategy, we actually raised prices. We raised from $10 on our lowest plan from $10 a month to $15 a month in order to set a clear signal that we were different than some of the things that we . . . We didn’t want to be so low priced where it seemed like people were comparing us to other schedulers at the lower end of the market because there’s a giant gap between the folks at the low end of the market, where we were sitting with our pricing and folks at the higher end of the market that are hundreds per month. So we wanted to set a signal that we were more applicable there. And then that also gave us the revenue to start to fuel those deeper improvements that would be difficult to justify for like the very different behavioral use cases of somebody who is booking, you know, yeah, just a couple of appointments per week versus somebody who is booking, say, 50 or more appointments per week.

Andrew: So you know what? With a little bit of guilt for our friendship, I said to you that I did use Calendly and I paid for it, by the way. And I used it when I went to . . . Where was it? It was Australia. And I needed a day of interviews with four interview slots and nothing else. And so I went to Calendly, I set that up, and then I created another account so that my assistant could also book it and adjust it. And we used it for that. And then once we were done with that, we canceled it. There was not a lot of complication involved. It was just this one thing. That’s not what you want to be. If Andrew’s only going to travel to Australia or Argentina, somewhere and do an interview for a day, that’s not your thing.

Gavin: Yeah. Well, I want to travel with you. That sounds great. I will set up your schedule for you.

Andrew: It was so much fun. If you’re good at going out, oh, you’d love it.

Gavin: Yeah. Yeah, exactly. Yeah, we did . . . And I realized in retrospect too, at the time when we decided to do segmentation based off of behavior, it didn’t seem like that drastic of a thing. But when I tell people, everybody has the same reaction of thinking about vertical-specific. But just thanks to talking with so many customers, we understand that there’s many more similarities cross-vertical than they are within one. So yeah, and it aligns with the value that people get. They see a lot more value with the higher number of appointments.

Andrew: I noticed that there’s branding at small points. If you’re looking to figure out who did our calendar, you can find out, right, that it’s Acuity. It occurred to me that that’s got to be where the majority of your customers are coming from. Right?

Gavin: That’s definitely one way. It has changed over time how we’ve grown Acuity. Oh my gosh, until the last couple of years, we really did no marketing at all. Early on in Acuity, it was SEO and word of mouth and over time, really just word of mouth. That powered by Acuity has definitely been a decent area of acquisition. But it hasn’t been as big as you might expect. Mostly because we’re pretty subtle about it. Like we’re not in your face showing you our branding as much. The intent is that it’s for, if you’re actively interested in how the hell Andrew actually books appointments, you’ll be able to find it, but it’s not like a brand awareness area for us too. So it’s really been SEO.

Andrew: Your competitors have a free option that intentionally is heavy on branded. You guys have a free option. Is that one of the reasons why you have it and then what goes into the free option?

Gavin: Yeah, it’s funny enough, we’re very flipped on our freemium model. Only about 15% of our users are actually on free accounts. It’s an 85% are on paid accounts. The free account was originally on there, yeah, with that intent that we would be able to get a much larger user base, and get more word of mouth, and promotion, and advertising through there. And it does work like that a little bit. The branding is just a little bit more obvious on our free account.

And what we have found though is we offer three paid plans, $15 a month, $25 and $50 a month, really scaling up as your business and your number of employees grow. And the free option too. And we found that the free option is not what most of our users need. But it does provide a level of comfort when you start out that for certain use cases, very, very small businesses, people who are much more on the casual side, and it’s a good fit. But it seems to provide comfort with people that if we . . . We’ve experimented with packaging, like how we show the free plan in slightly different ways.

I ended up finding that people are less likely to sign up for any of our paid plans too. It’s not just that we lose signups because people miss out on the free plan, but they miss out on the option. People who would have tried out a paid plan also actually don’t go to a paid plan if we end up hiding the free plan from our pricing in page too, which was an interesting finding for us.

Andrew: You mean the people who were paid, still want to try free to get a sense of what you’re like and then they switch?

Gavin: For new users who start out, what we found was that if we hide the free plan on our pricing page, that it’s not just we see a decreased number of signups, but not just a decrease number of signups equivalent to the number of users who would have gone to free and don’t have that option, but we also lose a number of people who would have gone to a paid plan, and also don’t sign up too.

Andrew: Oh wow.

Gavin: It’s very interesting. We’ve repeated that test multiple times to try to figure out why. And digging into it, it seems to be one of those levels of confidence too that you say, “I’m going to try out a paid plan.” Turns out that they end up sticking with it, that it’s a perfect thing, that the cost is still very low and, like, the power is so much in there. But we find that people find there’s a comfort in knowing that, “Okay. Maybe I’ll just end up going with the free plan in the end, but I can try out more features right now just to see what it’s like.

Andrew: I went through it and one thing that stood out for me was . . . I just went through it right now. Oh, it’s just changed. At the top of the page, it said, “Need help, call Ghostbusters and then in parentheses . . . ” Just kidding, press here.

Gavin: Oh yeah. I love our help button. We have rotating fun copy and, like, if you hover over the logout and some of the login messages too. We had a lot of fun with that. The help button too is actually very practical though because we did rotating fun copy, which adds more personality to the application, but it also shifts the size, especially as they’re starting out, it calls more visual attention to itself as you go between the pages.

Andrew: Yeah. So because if it was just a help word throughout the experience, people wouldn’t notice it. They’d get blind to it. Right now I just hit refresh again. It says, “Admitting it, I need help.” It’s not a help button, it’s just like text on the page and I can click it. All right, I should talk about my first sponsor. It’s a company called Toptal for hiring developers. Before we got started, your eyes opened up when I said Toptal. You had experience. What was your experience with Toptal?

Gavin: Yeah, we had an R&D project when we were in an independent Acuity and we needed contractors in some specific . . .

Andrew: Sorry, you needed what? We were just losing you. You needed . . .

Gavin: To scale up the team and . . .

Andrew: You needed contractors and . . .

Gavin: Oh, we needed . . . Yeah. Yeah. We were looking for folks with some specific technologies, with Laravel and React experience. And we went to Toptal and were able to find actually the perfect developers very, very quickly, much, much easier than hiring people on. And just the flexibility of working with them made it a perfect match for our business goals at the time.

Andrew: Perfect. And I can’t say it any better than that. If that’s what you’re looking for, go to And here’s the thing that, Gavin, you may not have gotten, if you use that URL, they’re going to give you 80 hours of Toptal developer credit when you pay for your first 80 hours, in addition to a no-risk trial period of up to two weeks. Don’t worry. The developer will still get paid, but you won’t have to pay if you are not satisfied. Toptal, that’s, I notice you’re drinking Hint water. That’s very, like, tech of you. Is that what it is? It is, right?

Gavin: Yeah, it is. I’ll be honest. Normally I drink Hal’s seltzer when I’m here, but I would be burping this whole interview.

Andrew: Here, meaning in this Squarespace office?

Gavin: Yeah. Yeah.

Andrew: Now that you’re in as part of Squarespace, were you a cheap, like, entrepreneur who prided himself on, like, not paying for the expensive water and now you’re getting the expensive Hint water?

Gavin: You know, Acuity was an entirely remote team because of our profitability. If we had an office, we would have tried to get a very nice one, but I was drinking tap water out of my house.

Andrew: And now you’re drinking Hansen’s. Living it up. You guys work quirky. I kind of mentioned how the help line says, “Admitting it. I need help.” Give me an example of the quirkiness that I may not see or may not notice as I’m looking at your company.

Garvin: Oh, man. One of the most important things to me is just, when I started Acuity, I had another day job with the government that I absolutely loved. And when I left that to do Acuity fulltime because it was starting to grow enough that it needed the fulltime love, I wanted it to always be somewhere that I would enjoy working. And one of the most important things is the people that you work with. So it was very intentional about personality. Like, the culture and building that out, even from the very early days. And we had an exceptional culture that over time, starting out with just a couple of people has ended up reinforcing itself too.

So as we grow and especially having a remote team, getting people who are naturally comfortable to just share and go out, and then what we end up finding too is, in our support, I hate the canned replies that some companies send out. And we are such a support focused company and such a customer-focused company. We do all-hands support. And one of the key things in there, for me, is that we sound like humans and people are comfortable sharing their personality, that they don’t feel constrained by canned replies. And that comes out, I hope to our customers when they’re interacting with our support, they know that they’re interacting with a human and that personality.

Andrew: I’ve got an example. I keep wanting examples. I’ve got one. I remember one of the first . . . the few things that stood out for me. One was I was getting lost because I was with your software since early on. And as you kept iterating and my business kept iterating, I feel like I’ve made this big mess. I asked a couple of questions and then you jumped into support and said, “Andrew, we’ll just take care of it. Tell us what you need and we’ll set it up that way.” And I said, “I have these producers, I have my own calendar.” And then you guys did it and you came back to me. That was a nice touch that you actually were there and noticed it.

The other thing that stood out for me was I got a response from someone and they had a link to a video of themselves with some funny something or other in the video. And I said most people don’t have the comfort to get in front of a camera, let alone to be interesting and funny on camera and the feeling that they have permission to not just say, “I’m here to help you out,” but instead say, “I’m here to help you out and here’s some wacky thing.” That is a uniquely Acuity personality. What am I not seeing has been building? Maybe beyond customer support.

Gavin: April fools is my favorite holiday. And we just started our April fool’s planning. We’ve done some fantastic things over the years. Last year, we have an expert’s program where you can hire an expert to set up your Acuity account and do all of these things. And we introduced the Acuity no show bounty hunters, who would go and chase down your no shows, and we did landing pages for them. And we had Alethea, the 85-year-old bounty hunter that would go and chase down your clients with her hearing aid and her dog. And that was such a good one or a kittens for calendars in a past year, which some people took way too seriously where we said you would mail in your paper calendar and we would mail you back a kitten. And people got very upset that we would mail people kittens without checking their background. That tickled my heart. So that’s one of those things that’s such a big one for us. And we try to reinforce, like, that type of thing all the time, getting everybody involved, and brainstorming, and thinking up the ideas. And yes, and ours this year will be very fun too.

Andrew: So that feels like a fun thing to do. How does it make you, like, day to day enjoy the people you’re working with more, enjoy your culture more?

Gavin: Yeah. And trying to get people to actually talk to each other in a remote team, you have to be very intentional about that. It’s not like you’re randomly running into people as you’re grabbing your Hint waters or anything else. So we try to connect people together to just, like, chat and to get to know each other, to have them introduce themselves, get to know the quirks about each other.

Andrew: Why? What does that do for a company if you know each other’s quirks?

Gavin: You know, it’s interesting. Once a year, we get together. We’re a remote company, a hundred percent remote. We have people all around the U.S. and internationally too. Once a year, we get together in person. And I love seeing people come together and just everybody hugs, like old friends and they feel like they’ve seen each other every single day because we have that human connection, even though we can be thousands of miles apart . . .

Andrew: Who cares? Like, why does that even matter for a company? I have that with my friends are going to come over tomorrow night or Friday night, we’re going to hug. It’s going to be great. Why does it help a business? Why does it help you to have this environment where people feel like they can hug each other?

Gavin: Very selfishly, I wanted a place that I would enjoy coming into every day. And I feel like if you have people who are just in it for the paycheck, I’m not going to enjoy that environment. But it also turns out too that if you start to look at studies, people will stay with the company because of their coworkers. We end up having phenomenal employee retention where we’ve had next . . . I think we’ve had, like, one person leave on a voluntary basis over about eight years, which is absolutely incredible. And I think part of that is making sure that you have a good work culture and that you enjoy the people that you’re working with, that you can be happy every single day. And I think we ended up achieving that and really finding the people who are the right culture fits, and finding the ones who I add value to there and, like, bring joy to everybody else, and not just so focused on the numbers or anything else, but focused on, you know, hopefully improving our customers’ lives, and enjoying our own time along with that.

Andrew: And how do you guys communicate? Are you a Slack company? Is there something else you’re using?

Gavin: Yeah, Acuity was a Slack company and Squarespace also uses Slack too. So that’s our biggest way. And like us right now on Zoom calls is a very important one too and Slack calls now as well. But yeah, getting that face to face. But really inside of Slack, we have just, like, a bunch of channels for things that are serious. You know, our developer team and our support teams are broken out into different channels, but then we just have, like, water cooler channels or, like, family pics or offices where people share, like, pictures of where they’re working from for the day. And it starts to get you to, like, know the other person and feel like they maybe are more along the lines of, you know, a friend, somebody that you can get along with. You’re more likely to approach them. You’re more likely to enjoy your day to day and your job too.

Andrew: I was wondering why Squarespace would want you guys. Like, it if feels to me that they’re about simple. Why do they need a tool that’s so robust? It’s Squarespace. Why couldn’t they just build their own scheduler, the way other people did?

Gavin: I asked myself that same question too. Why didn’t they just build their own? And I think, well, it turns out building your own scheduler is incredibly hard. I think they explored that a little bit. And Acuity is absolutely one of the best in class tools out there with the power of it. And Squarespace is such a beautiful tool but also incredibly powerful and really one of these tools where they’re developing more and more to support in, like, this all in one platform for independent businesses. And they’re very well-known for websites but they also have quite a bit more in their, like, e-commerce.

They recently launched an email campaigns product to send email blasts out and our analytics in there as well, and more tools to try to support businesses. And it fits actually very nicely into there. We’ve had a partnership for two years prior to the acquisition, where we were inside of their website builder to be able to easily add Acuity. So we knew that there was a strong connection between our customers prior to that. And we had a good amount of data with that. And now that we’re part of Squarespace too, we launched an integration called Squarespace Scheduling, which is Acuity within the Squarespace platforms that you can have scheduling included, you know, right in your website, where it’s very easy to add. But also you can get started very quickly with your same account attached to your websites with your contributors on there and everything else. And we’ve seen amazing adoption since just launching that in January.

Andrew: And the integration was done really well that I was prepared to be frustrated that there was any integration. And then I saw the login screen change to a Squarespace login screen and I said, “But no, now I’m going to have to create a . . . No, my username and password just works.” I said, “All right. Nothing’s different. I don’t even have to go . . . ” I don’t even go into Acuity anymore.

Gavin: Yeah. One of the major things with Acuity being a successful business too is we know it’s a phenomenal product. We know that we’re very good at acquiring customers and we want to make sure that Acuity and Squarespace, they work really well together, and that we’re not frustrating our users at all, and we’re providing everybody a good experience. We did some redesign of the application of that was a necessary thing in order to support the integration, and make sure that we could run seamlessly off of one code base, and feel like an integrated product, and also support our new branding. But when we did that, we tried to do it in a way that the information architecture stayed the same, that it was more of a visual change. So that existing users, that we would always respect them and provide a great experience.

Andrew: All right, I’m going to talk about my second company. You didn’t know who they were, so I’m going to open your eyes to a new company, a newish company. It’s called Qordoba. You know, you guys have a brand voice. There’s a way that you communicate at Acuity Scheduling. Do you guys have, like, a style guide somewhere?

Gavin: We don’t, actually.

Andrew: You don’t. People just know how to communicate. Well, for a lot of companies they want to have a style guide, they want to be clear. “Here’s the way that we talk, not just when we’re writing email to customers though maybe, but also when we’re writing blog posts, when we’re hiring outsiders to write blog posts with us, when we’re communicating on our website.” And so they might want to do a style guide but they never get around to it. And if they do get around to it, the people who write for them never think, “I got to go and look at the style guide to understand, how do we communicate?” And as a result, the language feels a little bit off. The best example that I always give is some companies that have two words, like Acuity Scheduling. If I go through their website, some people on the site write it as two separate words. Other people write it as one word, mashed together. Some have an upper case as for scheduling, others have lowercase. Right? Are you guys clear about it? How does it have to be? Acuity Scheduling, two words?

Gavin: It should be two words with both of them capitalized.

Andrew: And I don’t see an example here, but I don’t know how diligent you guys are about it. But little things like that are important to companies to have that sense of consistency and you also want everything to be written in the same grammatical voice. Well, what Qordoba said was, “You know what?? Come to us, fill in this form. We’ll create your style guide with your quirks. And if you want things like AP style guide in there too so that you have some formal set of writing instructions, great. Just check a box and we’ll make sure that it’s consistent.”

Then when your people want to write, instead of starting by writing in Google docs, they start by writing in Qordoba or they could even use the plugin and write whatever they want. But they could go to Qordoba, they could start writing. At the end, they could say, “Tell me my mistakes.” And it could be things like grammatical mistakes. It could be things like, “We don’t as a company say guys, it’s just not the way we talk. We say, “Y’all.” Y’all is fine here as a company. Little things like that matter to companies, especially in an environment where, in some places saying guys could come across as sexist, saying y’all could come across as disingenuous.

What is the word? The software automatically picks it out and says, “Here’s what we use. Do you want to change it?” The user can hit change, just like they do on spelling mistakes. This is brand new software. I think it’s a little bit tough to really grasp the power of it until you use it. So they’re going to let everyone who’s listening to me use it for free. And then if you decide to buy it, they will even give you 25% off. All you have to do is tell them you’re a Mixergy listener by going to this special URL where they will know it. It’s, again, I’m going to spell it. You know, there’s show notes now and all these podcast apps, but the podcast apps are hiding it. So we’ll include it in the show notes, but here it is for people who want to write it down, it’s, Very happy that they’re sponsoring us. You guys sponsored, I feel like we did well for you for a while and it didn’t work, right?

Gavin: Yeah. You of all the podcasts, Mixergy, I think we saw the best returns from because you do phenomenal reads and you engage your guests in them too, which I think helps.

Andrew: Love that.

Gavin: Yeah, we ended up, I think just saturating the podcast for a while where listeners hear the same thing over and over again. We sort of see this, where it goes flat for a little while as you’re just getting started and then you start to see a spike as listeners come in. That went really strongly for a while and then tapered off, which is why we decided to stop. We started doing more podcast sponsorships with Acuity for a period and ended up finding a good pattern was to sponsor for a period, stop for a period, and sponsor for a period, just as the listeners churn out and new ones come on, that seemed to get the best returns overall.

Andrew: What else worked for you? So podcasting, I didn’t realize that you guys had a whole podcasting strategy or you were . . . I didn’t realize you were buying ads anywhere except for me. But what else worked for you?

Gavin: I’m sorry.

Andrew: I hear you. I assume nobody’s listening to anything except for me.

Gavin: Cheating on you as a sponsorship. No, no, that was a phenomenal one.

Andrew: What else has worked?

Gavin: Yes, podcast sponsorships are very expensive too. You know, we started to get a few years ago more aggressively into marketing. SEO early on was great and then that sort of tapered off. We still have good rankings for things like online appointment scheduling. We found that there are some review websites, gosh, like G2 Crowd and some of them that you have to pay in order to get people to click through on links to you and Capterra. We found really good returns on those. Those are starting to diminish over time as they get more saturated, but they used to have phenomenal organic rankings. You would pay for your links in the listing there and normally get a sponsor badge. And we saw great returns from that for a while.

Good old AdWords though, man. They just keep . . . Like, that is probably from marketing our biggest fuel. But overall, word of mouth. People love Acuity and share it out. We have a referral program, where you can get up to $30 per referral, which works really well, but honestly, we find people just organically sharing out Acuity, even without participating in that program.

Andrew: You mean telling people to go sign up. It just makes sense. I feel like AdWords works really well for you because you’re at a higher price point than your competitors.

Gavin: That’s true.

Andrew: Right? There’s more of a budget there.

Gavin: Yeah. Yeah, that’s very, very true. And yeah, we’ve seen very good consistent returns for that and especially as the market changes over time. Acuity has been in this since 2006, where online scheduling was a very unknown type of thing. And people weren’t searching for online appointment scheduler as much. It wasn’t a known thing. And now, that’s changed over time. So I think actually AdWords has become more effective over time because there are keyword, there’s many keywords with, like, a strong signal of intent that we used to not have. So our strategies at the beginning, like things for SEO or just like talking to bloggers and search like that to get the word out there, now are less important and we can go after those high intent users through AdWords. And we tried paid social with Facebook in that and keep trying that and have such a hard time getting positive returns from Facebook.

Andrew: I was looking at SimilarWeb to get a sense of where your traffic was coming from and something stood out for me about where traffic goes. It seems like a significant amount of traffic from Acuity Scheduling goes to And that’s because you accept payment.

Gavin: Oh, interesting to see you see that. Yeah, we integrate with a couple of payment processors. We integrate with Stripe . . .

Andrew: PayPal is another one.

Gavin: . . . Square and PayPal, yeah, are our three main ones. And we have great relationships with all of them and have ended up supporting more and more features over time, like deposits and accepting credit cards on file and, like, letting you sell recurring memberships for appointments through Acuity. And so, payment processors, going back to the strategy about trying to support businesses. Payment processing is such an important thing in order for them to streamline their operations.

Andrew: And then for sources, somehow Uber is one of the top referrers. Is that because they’re a user or something else? You’re smiling, you know it.

Gavin: Yeah. Yeah. I never liked to share out our customers, but yes, they do use Acuity quite extensively too.

Andrew: Got it. Okay. All right. And that makes sense. So what was the deal that you had with Squarespace that led to this acquisition?

Gavin: Yeah, we did something interesting. I was trying a different experiment with them, which didn’t quite work out. We had Acuity, which was included in the website builder as a block that you could easily add to your website to add scheduling. And for Squarespace users, we gave away our lowest level plan, our emerging entrepreneur, completely for free. The idea was that . . . My hope was this was before we started shifting more and more upmarket was that we would reach a broader scale, that we would get exceptional lock-in.

So two things. One, that Squarespace would have no need to partner with another scheduler because we were giving their users such a good deal that every single Squarespace user who needed a scheduler would ended up using Acuity. And then second too, the hypothesis was by getting that mass reach, and especially having Squarespace, which has a more premium brand aligned with us, would end up getting us, you know, the scale, getting us more referrals but then we would also see a upsell to our higher-level plans, which we didn’t discount. I thought that Squarespace users because there was no free plan, would have a higher willingness to pay for Acuity. It turned out that wasn’t the case, that although people are willing to pay for Squarespace, that in the end, they were generally still on the very small businesses side where our emerging entrepreneur plan was perfectly good for them. So we did end up discontinuing that. But it was a great experiment and we still honor all the folks who had signed up for that at the beginning too.

Andrew: That’s why it’s even more baffling then that they decided to buy you because it’s not like this was a pipeline to new customers in a natural fit, the way I’d say email marketing would be.

Gavin: Yeah. You think . . . And especially, we ended up finding too, just Acuity way back in the day. I originally put out for signup because I had a web development business and I thought, “Oh, you know, businesses will need scheduling and when they start using Acuity, I can try to sell them on web development services,” which was absolutely incorrect. Everybody ended up having a website before they found Acuity. You start out your business with a website.

Yeah. So for us, I was interested in Squarespace. Actually for that same reason that Squarespace, when a business gets started, they get a website first. So it puts us up sort of in that acquisition stream for businesses and get us in front of them, especially people who might not be aware that online scheduling is even a thing. For Squarespace though, being able to sell services is they have their eCommerce store and trying to support businesses, and especially trying to provide a good integrated experience so that people can start, and really run their business on Squarespace and Acuity with supporting that. You know, more selling services online, selling appointments online, selling your time online was a great way to try to support that.

Andrew: Let me close out with this. I’m still curious what that clicking is. I can’t believe we can’t find it.

Gavin: I’m sorry.

Andrew: Thankfully, it hasn’t been going as much as it was before. I keep thinking about how your dad owned a restaurant. He would wake up at 4:00 in the morning to start cooking, sleep on the concrete floor, you told . . . Is my memory right about that?

Gavin: Yeah. Yeah. That’s exactly right. Yeah.

Andrew: And then you had a similar situation when you build Acuity Scheduling where you started working from home, you had very little in your house. You’d sleep on the floor for four hours, making sure that you were always close to your laptops so you can answer an email. I keep thinking back to that hard work. Like, it’s like your dad and then you repeating your dad’s difficulty, you built up something really big. What’s the best part of having sold this?

Gavin: You know, I love being part of Squarespace and I got to say, my dad had it harder. He slept on a concrete floor. I had carpeting when I had it for that time, but yeah . . .

Andrew: I mean, you had a job with the government. You could have lived really comfortably. You instead decided I’m going to suffer for a bit and I could see that other people are ready to take over that space. What’s the best part of all this?

Gavin: Really, it’s being part of the company and the culture right now, and being able to have other people supporting us . . .

Andrew: That’s it?

Gavin: . . . and our growth here. Yeah.

Andrew: All right, okay, I know people need to take that space. We are working at the Squarespace office. I’m going to thank you so much for doing this interview with me. Everyone else, go check out And I’m especially grateful to my two sponsors who made this interview happen, and Gavin, go ahead, run off, and give them their space . . .

Gavin: Thank you, Andrew.

Andrew: I’ll talk to you later. Congratulations.

Gavin: Bye.

Andrew: Bye. Bye, everyone.

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