More Time Less Hassle

Hosted By Matt DeCoursey

Full Scale

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Matt Martin

Today's Guest: Matt Martin

CEO & Founder - Clockwise

San Francisco, CA

Ep. #1191 - More Time, Less Hassle

Today’s episode of Startup Hustle features Matt DeCoursey and Matt Martin, Co-founder & CEO of Clockwise. Their conversation revolves around creating more time and less hassle and discussing the economic and personal impacts of scheduling meetings correctly. They also share their experiences and thoughts on the complexity of making a schedule for clients and team members. Plus, Matt and Matt discuss the benefits of placing buffers around your schedule and the challenges of educating your customers.

Covered In This Episode

Time waits for no man, and it is a commodity that you can’t buy. However, you can save it through Clockwise, an AI-powered calendar software that optimizes daily scheduling to create more time.

Listen to Matt Martin describe his journey to Clockwise and the problem that the software is trying to solve. They include time zone issues, calendar syncing, and customer education. Matt and Matt agree that efficient time management can help reduce hassle and create more opportunities. They also discuss how AI integration can help manage the complexity of scheduling meetings and events. The conversation then turns to the economic and personal impact of scheduling software.

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  • Matt’s journey to Clockwise (1:29)
  • The problem that Clockwise is trying to solve (2:23)
  • More time, less hassle, more opportunities (5:27)
  • AI integration (7:47)
  • The level of complexity in scheduling meetings and events (10:27)
  • Setting up buffers around your schedule (15:39)
  • The technical challenges in scheduling: Time Zones (22:22)
  • The challenges in calendar syncing (26:24)
  • The challenge of customer education (29:30)
  • The economic and personal impact of scheduling software (38:52)
  • Building and growing a team is vital for any business (41:28)

Key Quotes

One of the core insights for Clockwise is that time is really personal. That’s where you get to see my day. It’s when I get to see my kids. It’s become a shared asset. You know, people are asking you about your time, all throughout the day, whether it’s in a meeting, event itself or whether it’s in an Asana task, or whether it’s getting pinged in a dock or getting pulled in an email or Slack, you’re constantly being asked for your time.

– Matt Martin

When I talked to small business owners and just what I experienced and witnessed and everything that so many of them were chained to their businesses too. If you’re a sole proprietor and you want more time and less hassle, online scheduling is a must. I think, in 2023, that it’s an expectation. So, you talk about more time, less hassle, how about more money, less hassle because in this day and age, if you don’t have these kinds of options available, you’re just missing opportunities.

– Matt DeCoursey

As business owners, managers, and people inside a company, it is so easy to forget the cost of meetings and our schedule overall. There’s the meeting itself, which is really costly, you can think about multiplying the salary of everybody involved. Another thing is the productivity blast radius around every meeting. So thinking holistically about how you’re running your team, how you’re running your company, and what kind of productivity standards you are setting is critical.

– Matt Martin

Sponsor Highlight

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Rough Transcript

Following is an auto-generated text transcript of this episode. Apologies for any errors!

Matt DeCoursey  00:01

And we’re back, back for another episode of Startup Hustle, Matt DeCoursey here to have another conversation, I’m hoping helps your business grow. Alright, so we’ve all talked about scalability and accessibility and a lot of different stuff. But one thing you can’t scale is time. That means you got to learn how to do more with it. So we’re gonna talk about more time with less hassle today. And before I introduce today’s guests, today’s episode, Startup Hustle is powered by Hiring software developers is difficult and Full Scale can help you build a software team quickly and affordably and has the platform to help you manage that team. Visit to learn more. There’s a link for that in the show notes. With me today, I’ve got Matt Martin. And Matt is the co-founder and CEO of Clockwise, it’s a software development company in San Francisco, California. And you can visit and learn more about what they do at There is a link in the show notes for that as well. So do me a favor once you scroll on down and give that a click so you can learn more about what they do and how they do it while we talk about it. Without further ado, I guess I should probably say, Matt, Welcome to Startup Hustle.


Matt Martin  01:08

Thanks so much for having me. Happy to be here.


Matt DeCoursey  01:10

Yeah, it’s a as mentioned, before we hit record, I’ll be able to remember your name a lot easier. So. So there you go. You know, why don’t we just get things started today with a little bit more about your own backstory and what brought you to Clockwise and and how that journey has been?


Matt Martin  01:28

Absolutely, yeah. So I have a little bit of a weird background, I started my career in kind of politics campaigns, decided I wanted to be an attorney. I went to law school practice as attorney and a large law firm doing kind of pretty boring corporate litigation for a little while and then decided that I really didn’t like that. And build on it about 13 years ago, came out to the Bay Area and jumped at the startup, startup ecosystem. And I knew a little bit of coding, Matt, knew enough to be dangerous. So I found some early startups that are willing to take a risk on me. Got more into software engineering. And that’s what I’ve been doing ever since. Software engineering, software engineering management. And that started Clockwise about six years ago.


Matt DeCoursey  02:17

What was the what was the main problem you wanted to solve when you started Clockwise?


Matt Martin  02:23

Yeah. So I mean, it’s a, I love our problem space because I think it resonates with everyone or at least it usually does. I was working, I’ll give you a little bit background, though. And some of the elevator pitch version. So the last company I was at, a company called RelateIQ. It was an intelligence CRM, so we would connect to your email. And that would pull out information about who you’re talking to as a salesperson. In order to power the CRM, the customer relationship management database that was acquired by Salesforce, and actually was kind of one of the initial investments that Salesforce had in AI led to their Einstein platform, which they continue to develop to this day. So here I was, I was leading our front-end engineering team. Getting kind of sucked up into the mothership of Salesforce and by the way, like, realistic view at the time was about 60, 65 people. Salesforce was, you know, 20,000, 30,000. I mean, they’re larger now. So we’re definitely getting ingested into their culture, and a lot of lessons there. But for me, at the moment, I was just kind of pulling my hair out trying to manage my own time and my own calendar. Getting pulled in a lot of different directions. And when I tried to best manage my team, I was trying to help with the integration process, sync with other people inside of Salesforce. And I think at the time, you know, I kind of had the wrong attitude about it. And we can talk about this more, which is, I said, you know, whatever it is my job. I’m a manager, I guess I just have a crazy schedule, I’ll just do it. But I was also seeing it on my team. So software engineers, you know, they need a lot of time to go heads down, get into the zone, start coding, I mean, you know, this, and their schedules are getting kind of Swiss cheese as well, with all these different meetings, whether it’s, you know, siyncing with their team, whether it’s been pulled in an interview. And at the end of the day, they just won’t get as much done. You know, these are software engineers, Silicon Valley, and it’s expensive. You’re paying pretty good salaries, benefits, for people to come in and not be able to be productive, they want to be productive. So long story long, I was looking at the mess of all this and thinking like there’s got to be a better way. And one of the core insights for Clockwise is that time as personal as it is, and it’s really personally that’s where you get to see my day. It’s when I get to see my kids. It’s become a shared asset. You know, people are asking you of your time, all throughout the day, whether it’s in a meeting, event itself or whether it’s in an Asana task, or whether it’s you know, getting pinged in a dock or getting pulled in an email or slack, you’re constantly being asked for your time. And yet, there is no tool that helps solve at that shared space level. And so that’s what Clockwise used to do. We seek to connect to your calendar, help automate it to make more productive time by looking at the intersections across everybody you work with and how you need to work as a team.


Matt DeCoursey  05:27

We’ve got a lot of scheduling familiarity on the show today, as you know, someone who built GigaBook, wanting to solve the same problems, you know, at the time and 2012. I just sat back and I realized, like, how much time is wasted with Hey, Matt, when are you available? I don’t know. When are you available? How about Thursday? No, Thursday is not good. How about Friday at two? No, that’s not gonna work? How about too, you know, I mean, you talk about like, the same way that you that you’re using AI to find little bits and pieces and pick up time. You know, I felt the that was a ton of wasted time. But the main thing with, you know, you talked about more time, less hassle was, you know, when I talked to small business owners, and just what I experienced and witnessed and everything was that so many of them were chained to the business too. You talk about, like, if you’re a sole proprietor, and you want more time and less hassle online scheduling to must, and it’s almost I think, in here in 2023, that it’s, it’s an expectation, and so you talking about more time, less hassle, how about more money, less hassle, because in this day and age, if you don’t have these kinds of options available, you’re just missing opportunities. And most of the people that I talked to that, that own small businesses really did feel like captive to the business, because, you know, they’re up at 11 at night answering text messages and emails, and, and you know, really, in the end, kind of losing opportunities. And I think that too many people like kind of like, you mentioned that, with your engineering team with it being really expensive. Too many people don’t understand, like, as a business owner, that saving money is making money and freeing people up to do their jobs. You know, when you have if you have a meeting with 10 people in it, and they all get paid pretty well, that’s a pretty expensive meeting. Totally look at it. So what are you accomplishing? And how are you doing it? Now? With that with you guys using AI. And let’s talk about that for a second. Like what what are the what are what are you guys doing that becomes intelligent or the efficiencies that’s picked up? I see you’ve got some, some GPT integration and stuff like that. Explain to me what you’re doing there and how that’s helping your users?


Matt Martin  07:47

Yeah, I mean, it’s so so many good things that you hit on there. I’ll jump right into kind of how our intelligence is powering the whole system. So we’ve been doing this for six years. And so prior to the recent Advent and LMS, you know, huge explosion in terms of that technical logical space with GPT, ChatGPT coming forward, and then GPT 4 making a big difference, at least in our flows. But even prior to that, you know, Clockwise, is an intelligent system. You know, we’re looking across, and we’re a little bit different than Matt, GigaBook, and that our audience, our customer is usually kind of mid market to enterprise side technology firms. And so they’re largely looking at their internal time. How can we make sure that we’re using this really valuable resource, as you know, to its most productive end? And so we comb and analyze millions and millions and millions of calendars of events every day. We’re processing every single calendar event inside of an organization to understand, you know, when is a bad time for this event? You know, when is it interrupting somebody’s flow time? When is it actually double-booking them? Do they need time for lunch? Have they been in back to back zoom meetings for too long? And so pulling all that information together, processing and applying some weights and biases to those different events in order to find the best times for them? It’s kind of at the core of what we do. Now, on top of that, there was the move from Open AI’s GPT 3.5, which is what Power Chat GPT and what led to kind of this explosion of interest when people went in and you know, figured it could figure it out that it could write a funny Limerick to GPT 4 was actually a big shift for us a clockwise because between 3.5 and four, it became quite good at understanding time based information. And so we’re previously we kind of botch whether 10:30 on Tuesday is after 10pm on Monday. It now can reason about that. Now it does doesn’t have the intelligence are Clockwise in terms of scheduling and understanding how to put something on the calendar and it can hallucinate. The last thing you want is, you know, to put a hallucinating event on your schedule at the wrong time. But we figured out that we could marry that really simple, easy, intuitive interface of just saying, hey, I need time tomorrow with my engineering team, and then help understand how to make that a reality. And that’s actually what we’re working on right now. And I’m pretty excited about it.


Matt DeCoursey  10:27

Yeah. And that’s, I mean, that’s a level of complexity, the, you know, like, you look at all the there’s a lot of scheduling tools out there, you know, and a lot of different things that do similar stuff, they all kind of have their niche. GigaBook, when it’s fully customizable, which I’m looking back at, it might not have been the greatest trajectory because you have to install a hell of a lot of bells and whistles and variables and stuff like that. And, and you’re right, I mean, it’s a lot different like yours. I really like what you’re doing because you talk about that, like that, that level of, oh, gosh, we were talking about the inefficiency of asking one person for a time they’re available, trying to figure out when’s the best time when eight people are available. And I like that, that more in depth look of like, has this person been in three meetings in a row, or whatever. And keep in mind, like, if all if your people are just in meetings all day, they’re not going to have time to do the work. That’s what that’s what drives me nuts about like, we’ve really cut down on a lot of the meetings and stuff we do at Full Scale. Because if you have six hours of meetings every day, all day, you don’t have any time to actually do the follow up, do the work. They’re they’re taxing, they’re, you know, and there’s a lot to be said with that. And, and I liked the empathetic nature of like not, you know, just like, hey, you need a lunch break. Yeah, and these are, these are the things that I think that people don’t really think about. Scheduling can be remarkably complex. Now, the act of putting a singular item on a single calendar on and off is not that complex. But when it’s connected to invoices, reminders, notifications, you know, knows, man like some of you also have have things involving groups of people, which by the way, booking a group of a group type event is a completely different set of logic than booking a singular appointment. Yep. Because it’s the group fall, is it, is it like a standard booking calendar like GigaBook or Calendly, or something like that just shows holes in your calendar? Yeah, it doesn’t give that empathetic feel of like, this person’s done three things in a row here, they might not be a great participant, if we put a fourth one in there and like, I have a lot of appreciation for the for the, for the for what you’re doing there. Because like, there’s a lot to be considered. Now, do you have to do you have to build and and essentially kind of like, create, for lack of a better term personas that? Like, you know, like you said, like, I just different flags are like, how do you know what like, do you look just literally look at this person has been in this kind of a meeting three times in a row? Maybe the fourth one isn’t, isn’t a best bet, or?


Matt Martin  13:11

Yeah, I mean, we have. So a lot of it comes back to having smart defaults, you know, we want to make the prosecuting setup with Clockwise really easy, and it is really easy. But then you can really dial it in. So we first we learn about your calendar, and kind of how you’re you’re meeting when you tend to have meetings when you tend to not. But that’s not always the best indicator of what you actually want, you know, those can be different. And so we allow people to dial in, you know, when do you prefer to have heads downtime, when you prefer to have you know, lunch is a really minor example in terms of what we do, but it’s kind of illustrative of the overall system. So you can come in, and we default to saying, hey, it’d be great for you to have 45 minutes for lunch, somewhere between 11:30 and, and 1, but you can dial that in. So it’s, you know, I only need 30 minutes, I would prefer to have 45, make it somewhere in between here. And then we’ll actively bump that around automatically in the background. And I want to hit on something that you were talking about, Matt, which is just the the, you know, as business owners, and as managers as people inside of a company. It is so easy to forget the cost of meetings and our schedule overall. You know, it’s like there’s the meeting itself, which is really costly, kind of you can think about multiplying out the salary of everybody involved. But then I think another thing that people lose sight of is there’s kind of a productivity blast radius around every meeting. You know, if if part of my job is getting back into the flow and delivering impact for the business whether, you know, I’m a manager working on a strategic strategy for next quarter or I’m a software engineer going head down a code. I’m coming out of that meeting, thinking about the meeting, recording tasks about the meeting, following up, you know, there’s at least 15, 20 minutes there that shot around that. And so like, if you only have an hour between meetings, it might sound like a lot of time. But you know, you’re spending 15, 20 minutes getting out of that last meeting, you’re left with, you know, 40 minutes, 40 minutes. And then there’s again, what can you really get done before this next meeting, and you just go back into email triage mode, you know, let’s, let’s run down the burner list. Just keep on processing stuff. So thinking holistically about how you’re running your team, how you’re running your company, how what kind of productivity standards are setting, like is really, really critical and can be huge, huge return on investment in terms of getting back to the productivity of the organization.


Matt DeCoursey  15:39

Yeah, well, I’ve been quoted as saying, you know, overbooking is the enemy of creativity and innovation. Yeah. I mean, it really is for the reasons that you just mentioned. And it’s, I’ll give you an example. So I block off an hour, an hour and a half to record a 40 minute podcast, you know, and some of that’s, you know, a few minutes on either side to talk to the guest. And then the rest of it is exactly what you said, it’s clearing that headspace because it’s difficult, I think that if you create a rushed scenario for yourself are your employees. So let’s just just picture yourself being booked in 30 minute increments for the entire day, that actually becomes a precision operation at that point. Because if one thing spills over, you’re going to have to steal that time back from all the others, you know, one of the one of the ways that I’ve handled that and, and hey, you don’t need GigaBook or, you know, Clockwise or anything to do this, stop scheduling 30 minute meetings, make them 20 minutes. Like, everything, it’s an we kind of inherently as people want to put things in 15, 30, and 60 minute blocks, don’t get them at 10, 20, and 40. And that creates this little buffer, you know, one of the things that GigaBook does, or any service or any kind of booking option that you have in there as you can set up a buffer around it, you know, because like, that’s like one of the things it’s like, let’s just take this down to, like, the sole proprietor kind of level. If you’re a massage therapist, and you’re doing one hour sessions, you can’t book every hour, unless you’re going to cut people short or do whatever. And, you know, so you need the those automatic buffers in there. I just put him in there just on everything that I do. Like, cuz I think the reality is, is things always take longer and, and I just don’t like feeling in that situation. I don’t like have that feeling like where I’m rushed, and I’m behind. And now it’s like, Hey, I gotta cut this short because you know, and then. And here’s the thing is, if you’re trying to build relationships, you’re trying to provide quality service, you’re trying to be there for your employees, that isn’t really the right mindset to have during that situation. Because it shows. People, I’ve literally been in that spot people, you seem like you’re in a hurry, like, do you want to do this another time? And you’re, like, no, yeah, I kind of do. But I don’t want to tell you yes. Because I know it’s like a jerk. So


Matt Martin  18:10

Oh, man. Yeah, there’s so many interesting things in there. I mean, one is kind of the the human psychology of it. And so to plus one, what you’re saying about shorter meetings. So if you’re, if you’re a sole proprietor, you’re the I love the massage therapist example. Because yeah, you make that 45 minutes and actually get 15 minutes kind of reset, go on to the next client and actually increases the overall economics of your business. If you’re now that plays on the psychology of people expecting to arrive at a certain time, but then need the buffer between. If you’re inside a company, if you’re in a kind of more knowledge work, we’ve found that the opposite becomes true. So it’s better to start the meeting 5, 10 minutes late, intentionally. Because people think, again, your point, they always think on 15, 30 minute increments. So I’ve seen folks and I’ve tried this myself, where you start a meeting at 10am. And you try to end it at 10:20. Well, guess what everybody in the back of their head is thinking that it’s going to 10:30 anyways, so it ends up running over your buffer time. And you end up going at 10:30. So if you see some of the offers there, yeah, if you start at 10:10, you know, the odds are, the other person shows up at 10 AM. and is like, whereas the other person, but they’ll get used to the fact that you’re starting late, and you have that buffer baked in, and then you run right to the 30 minute mark and say, you know, hey, I gotta run to the next thing. But you still have your buffer baked in.


Matt DeCoursey  19:40

One thing I immediately noticed when I made those changes, and like the times that were offered was that the people that I was on calls with like, I mean, I noticed this like day one. We’re all started saying, oh, I see we’re about out of time. Yeah, it’s like the other person knew like it shows it sets that fence around it. Yeah. And like I said, it’s just it really, it gave me a lot of time back. Because the problem is, is you get back into that, like six straight hours of booking. I mean, I get 100 to 200 emails a day. Yep. A bunch of other crap. I got two kids, you know, there’s a lot of stuff that can boil in there. So sometimes you talk about, like, what can you get done in five to ten minutes, you can answer a couple emails, so you don’t have a pile of them at the end of the day. Couple Slack messages here and there, it makes it pretty easy. You might even find a few minutes to go to, where you can find expert expert software developers, all you need to do is go to Or you can build a software team quickly and affordably. You can use Full Scale platform to define your technical needs, and then see what available developers testers and leaders are ready to join your team. Go to to learn more. Once again with me today, I’ve got Matt Martin, co-founder and CEO at Clockwise out of San Francisco go to get You know this? Alright, so let’s talk for a second, let’s share our grief of as people that have built so you gotta gotta comment?


Matt Martin  21:09

What I just kind of say, Matt. I mean, this is how I know you’re a true professional and that you’ve been in this podcasting game. That was the smoothest transition, though, that was amazing. Well done.


Matt DeCoursey  21:18

By the way, I take a lot of pride in that my other co-hosts on the show, always, always show a little envy with that. But yeah.


Matt Martin  21:27

I’m a podcast addict, really. And you know, there’s nothing


Matt DeCoursey  21:31

Ads are annoying, dude.


Matt Martin  21:34

It’s jarring to when you have this, you know, you have your host, they’re talking. And all of a sudden, it’s like hard stop pre recorded move. Nicely done.


Matt DeCoursey  21:43

I try to work it in there. That was that was a medium one. I’ve done better though. I’ve done better. So back to sharing grief. You know, like with this, so you talk about, I think, we I would be missing a great opportunity to, to expel some scheduling demons from my thought process. So what what what were some of the hardest, or what even continues to be some of the hardest things that you deal with when it comes from like a programmatic and technological standpoint when it comes to all the scheduling stuff? Because like I said, it’s a lot more complex than people think it is.


Matt Martin  22:21

Yeah. We know the standard standards spec for meeting recurrence, labels, probably better than almost any other shop on the face of planet. Because we were often dealing with recurrences instead of single one-off meetings. And the way that that spec is implemented and understood is just all over the place. It is, it is it’s kind of brutal. So from a highly nerdy technical perspective, that’s one of the biggest, but then I have to say, just in terms of user experience, it’s time zones. It’s always time zones, you know, I mean, like, it’s wild, Matt, like, I’m sure that you’ve seen this too. But you know, all of a sudden, Brazil will implement a new non-standard one-off time zone, it’s like, you know, you gotta go, you gotta go fix that in their code right away.


Matt DeCoursey  23:14

We deal with the with the Philippines because you know, Full Scale, it’s got over 300 employees there. And one time of the year, it’ll be a 13-hour time difference. They don’t do daylight savings time. Yeah. So some of those things are kind of tricky. And you know, the, the nations and governments of the world have a tendency to, to change this. Thanks. So one of the things that’s been kind of a challenge to talk about internationally is, in the United States, we have a very set and complete list of government holidays. At the beginning of the year, that I don’t expect any new holidays to come up, not so much over in the Philippines. So we use GigaBook is a big driver of the Full Scale platform when it comes to both internal and external scheduling and that timezone and those holidays. So, you know, that dude, it’s crazy, that it’ll be Monday, and they’ll announce it, but we’re gonna have a holiday on Friday. And it’s like a real holiday. It’s not like, you know, like, like Labor Day or something where people are just like, wow, that, you know, so that that throws curveballs at us. And then, you know, you talk about that timezone recognition, you can do that pretty quickly and easily. Like, if someone’s visiting a booking widget, you know, because you can detect their IP and just see where they’re at. It makes it pretty easy. It’s even got a little correction drop down. I can only imagine that that’s got to be a pain in the ass. If you’re just connecting a bunch of Google calendars or, you know, intranet, kind of talent. Everyone has their settings squared away in the same, same way.


Matt Martin  24:51

One hundred percent, I mean, Clockwise, like, so. It’s great because you can install it side by side with Google Calendar and a Chrome extension. So we do have Have a friend and experience. However, a lot of the automation and a lot of the values driven server-side. And so we don’t always have updated information about where the client is where the customer is. And that can be brutal. We’ve found various mechanisms throughout the years to make sure we’re getting the best information we can. But even if even once you correct all of the technical issues, which are many, and I always joke like, you know, just to make my life really easy, I decided to start a company. And then I decide to start a company that drives behavior change. And then I started a company that drives behavior change, where time zones is a big technical limitation. But so there are a lot of like complications. But then you get to the human side, and like, Look, you have folks in the Philippines and, and what’s great, they often, having worked with a lot of professionals in the Philippines. It’s not uncommon for them to work US hours, which is great for Full Scale is business great for your clients. But let’s just say you have somebody in the Philippines working local Philippines hours, then you have you in Kansas, and they have somebody in London. Well, you know, look, I can’t change the physical realities of the globe. Now you only have a really tiny window where all three people can meet. And often somebody is getting up early, or somebody’s going to bed late.


Matt DeCoursey  26:22

Yeah, and then, you know, I think one of the things that’s the that’s challenging about this is, God forbid you mess up someone’s calendar. Yes, like, I mean, you want to talk about pissing some people off? Yep, leave it you may use the term a hallucinated event. So your calendar syncing is a real pain in the ass when you talk about like putting like a Google calendars in interesting bridge because if you can connect to Google Calendar, then you can connect to a lot of different things. But you just talked about this complexity of like what, you know, Microsoft calendar wants, and I don’t know, there’s a ton of different stuff out there. And, and you know, so the order of operations that exists with putting something on a calendar sometimes has to be thought of backwards if you want to take things off. Yep. So with you guys moving stuff around all day, I can only imagine, like, there was probably some anguish along the way, when it came to figuring that out.


Matt Martin  27:26

Oh, man, it’s it’s so what are the what are the other aspects of Clockwise, and I think any company, you know, GigaBook, Calendly, any of these companies that rely on the calendar is that, as you noted, you, you kind of have to operate conservatively, which is not how you want to operate as a startup that’s trying to move fast, but you know, look like you mess up somebody’s calendar. You not only burn that bridge, they’re gonna tell your friends about their friends, you burned your reputation company. So one of the biggest inflection points for the business was very early on, we have this core technology called Flexible Meetings, and a Flexible Meeting is one that we’ve identified or you’ve elected doesn’t have to be exactly at 10 AAM. You know, maybe it can be anytime Tuesday morning, or it can be anytime in the day on Wednesday. There’s some flexibility, the timing of it, and we will automatically manage that. So that puts us in a little bit. You know, it made us nervous, it puts us in a little bit of a zone where we could really piss off a user by moving it to the wrong time. And, you know, again, as you noted, we’re doing this for hundreds of thousands events every day. And early in the lifecycle of business, we decided to start turning some of those on by default when a user joins, and we show it to them, and they can turn them off. But we were really nervous about turning them on by default because we thought we’re gonna piss some people off and God knows we have. But the impact we can make the calendar, the impact of that we can make the schedule far exceeded the few times that, you know, users were unexpectedly, you know, pissed off, and then when they are mad, we can learn about that, correct for it. And so there’s this constant balance between the velocity of that business and making sure that we’re taking care of our customers. And hopefully, in most areas, those are aligned. But sometimes you got to push a little bit into the area that makes you uncomfortable, so that you can learn and build in the right way.


Matt DeCoursey  29:30

Overall, people don’t like change. You know, meaning human psychology just isn’t really built for change. I mean, we are very comfortable with things that have become routine. And you got to build a new routine with that which psychology says can take up to 30 days to, like, truly build a new habit. I think it’s one of the things like early on, if you look back like here we are in 2023, like even, you know, 2016 when you started Clockwise, the the booking link or the online calendaring, I would send it to people and people like yeah, I don’t do this stuff. Yep. Yep. And we’re like what? Like you just click a button and pick a time and put your name in. It’s not that hard. Like, you’re not, this isn’t this isn’t AI. I’m not asking you to program anything like click, click boom, and it’s that simple. But now in 2023, I think that the the booking link in general has, like if you’re not using them, alright, why? Yeah. Because I mean, I’m almost like, offended a little bit. If you’re asking me when I’m available. And like, you know, it’s like, there there. There are use cases for things like Clockwise and GigaBook, but there’s no reason why anyone can’t have a simple anything clicked in and yeah. And someone’s out there listening, they’re gonna wait is GigaBook and Clockwise competitors now, not even close. Like, it’s different shit, it’s different stuff. It’s the same thing with Calendly. Like, if you just want a simple, I tell people this all the time, I’m like, if you just need a simple calendar option, that can actually get it done for you. But it’s not going to do a whole lot past that. There’s not like a lot of data collection. And there are some things in there. But I mean, if that’s if that’s all you if $0 is all you have a budget for, you can still get some of that done. And I’m just telling you, you’re gonna win your time that we’re talking about more time, less hassle, that’s the way to do it. You know, if and if we were wrong about that, like the next, the next thing to build might actually be kind of like Amazon that one click purchase, click a time and boom, you’re in you know, now. I mean, there’s there’s options out there for stuff like that. But yeah, the I think that, that customer education was a challenge too. God, God knows we’ve we’ve had some, like, we had one instance that I won’t get too far into the details for privacy reasons. But we couldn’t figure out why someone kept double booking some stuff. And because when you go to Schedule, GigaBook will tell you, so you have a conflict here, right? Now, sometimes you want to put two things on your calendar. So there’s an override button, but oh my god, we went crazy for like three months. We’re like, why is this wrong? Oh, the customer had been clicking override had been double-booking themselves. And then every single time was reporting the double-booking to us. And we’re like, oh, man, but you know, some of the stuff can be a real hassle. But that’s, that’s that habitual nature of things trying to get? Do you have a hard time getting people to understand the AI component or is it? You do?


Matt Martin  32:38

Yeah, I mean, there, there are a couple of great things that you hit on in there. I mean, I think that, you know, this, all this whole area is so ripe because I think we’ve all been somewhat set in our ways. You know, calendar is such a huge area of how we drive our business, how we drive our life. And yet, there hasn’t been a lot of innovation there. And so to your point, like with these with the links that are sent out an email to book times, there was even an uproar over this like a couple of years ago, where like, it’s rude, dissented, yada, yada. Well, you know, Calendly has made such a space for it, that it’s becoming more normalized. And there’s still a lot of folks that aren’t, as in the tech ecosystem, as you and I are, that are still a little bit apprehensive about it. So but but the point being is that, you know, we all grow this pie together. You know, as more people learn that there’s a better way to do this, there’s more opportunity for everybody to build a subsequent business and the use cases can become more specialized. And so, we have found that, you know, building that habitual habit, helping onboard people, helping them understand it is a huge part of what we do is a huge part of what we do, because it is anytime you’re automating something as critical as the calendar, there’s going to be a little bit of fear and apprehension on the side of the customer. And so, we we found myriad ways to, you know, help people dip a toe in the water and help them get comfortable, but also just educate them along the way as to the benefit they’re gonna get on the other side, which can really be pretty profound.


Matt DeCoursey  34:14

Yeah, I think the you know, if you want to sell more just got to make it easier for people to buy stuff. It’s the same thing with scheduling. So yeah, I can only imagine, like, it terrifies me to try to build what you’ve built. Because I’ll tell you what, like the phone would never really ring that much at GigaBook, but when it did it, it would ring a lot. We’d be like, Oh, God, something’s broken. something’s broken. Yeah, you don’t hear from people they’re quiet and unassuming until you break their calendar and or don’t let it come in. And


Matt Martin  34:49

Yeah, I mean, as an example, all of Ubers engineering department, you know, runs on Clockwise. And so, you know, we have if we have a bug where all of a sudden something bad that is happening, we are definitely going to hear. So it is one of those areas where unfortunately, you know, because we’re such a critical system, we do have to be a little bit more conservative with how we build and deploy to make sure that we’re taking care of folks.


Matt DeCoursey  35:15

That’s how you know what you build is important though. I know that sounds like weird, but when it breaks, and like that was I remember the very first time that this hasn’t happened in a long time, here I am knocking on wood. But you know, that I remember, like, the just were like, shit, we really got to get this movement gotta get the spirits like, this is a problem, the phones rang. And, you know, this was like years ago. And I remember having sitting there with the team and saying, well, I think the moral of the shining, bright point of today was you realize how crucial the system you’ve built is, when people immediately don’t have it and they’re immediately like, whoa, and then you’re like, oh, wow, what we felt really is significant, it really does matter, you’re going to see as we kind of approach the landing the landing strip here for the end of the show. You know, I think that I’ve always taken a ,we don’t serve as nearly as many users as you do. But I’ve always taken a sense of pride in building something that helps small business owners and, you know, you’re you have an enterprise solution. And if you’re not aware of like that difference, like GigaBook is, like good for like, to me, it gets that you have a vastly different system, user interface, user experience, everything, when you get past about 20 people, and something dropdowns get incredibly long, you got to like really do a whole, there’s a whole lot to get to different kind of product. But being able to help small business people and you know, all these years later seeing like, like, you know, I think eight of the 10 first users that we had are still users. And that’s like, you know, looking at that, and when you actually think is founders and CEOs and entrepreneurs, we don’t always talk to our users enough, you should, because when you talk to them, and you say, Well, how are things going, and they’ll tell you things, it’d be like, man, I wouldn’t be able to do what I do and stay sane without this. So you realize you’ve, you’ve really built something that’s useful that solves a problem. And I think the first time you talk about more time, less hassle, I think the first time you get a paid booking, like, what you don’t have to talk to the customer, you don’t have to talk to whoever it is, they pick a time, you get an email that collects a payment, and you just show up and provide service. And I think once that occurs a couple of times, it’s real easy to wrap your arms around that. Now with that the problem is, is if you want to make this stuff you have to go, you may have to go through a short period of tough love with your existing clients and users that have been used to calling or texting or getting a time. Don’t be afraid to retrain them, including the people in your organization where there’s something like Clockwise, which is more across your organization, or it’s client-facing. You gotta have a little bit of tough love in there. You know, like we go through that with with Full Scale, which has GigaBook it integrated into all the employee profiles, which you know, people like, Hey, I’d like to interview this person. How do I talk to him? You’re like, you just clicked the time right there on the profile? Well, I’m available at these times. Are there? I don’t know. Have you checked the profile? Yeah. And that sounds like kind of an a whole kind of response. But the thing is, is you’re actually doing your clients, users and co-workers a favor, by training them to do that and showing them so like, if you want to really make this stuff effective, you can’t be afraid to push back and say, hey, look for your, for more efficient and better use of your time, my time, everyone’s time. This is the way we got to do it.


Matt Martin  38:52

Yeah. Yeah. I mean, I, and I would note, you know, both for GigaBook and Clockwise. I mean, it’s one of those rare circumstances, I think, in software, where it’s both economically impactful, and personally impactful. Yeah. Yes. You know, when you were talking about earlier with, you know, somebody solo proprietors who are running their own business, you know, always be on the clock, always having to answer for the customer, always having to respond to the email. You know, alleviating some of that is really meaningful. And it also improves the loss of the business because now you’re not blocked from making that booking, you’re not blocked if you’re out with your kids. For Clockwise is kind of similar, where, you know, we the real ROI we provide for the business is helping the business move faster because people are able to get more stuff done, they’re able to get the meeting with the person that they need, they’re able to get the heads down time to make the impact. But also just feels better. You know, if you get to end your day, where you actually got to ship the code you wanted to ship instead of spending in meetings, or if you actually got through your day without being double-booked and feeling like you’re running around with your head cut off. That just feels better as well. So, I couldn’t agree more getting out talking to customers hearing those stories, it is so energizing, especially when you’re a business like ours, where you get to ship impact both for the user and for the business.


Matt DeCoursey  40:12

Yeah, and you know that I mean, there really is like, I don’t know, I, I wake up every day just wanting to do impactful meaningful things. And sometimes these little things are what matters. You know, I got a quick question for everyone. Before we do the founders freestyle, do you need to hire software engineers, testers and leaders because Full Scale can help. We have the people in the platform to help you build and manage a team of experts. All you need to do is go to, you’re going to answer a couple questions. And our platform is going to match you up with fully vetted, highly experienced software engineers, testers and leaders. Full Scale specializes in long term solutions with teams that work only for you. Learn more at As a reminder, with me today, Matt Martin is co-founder and CEO of Clockwise, go to I mentioned the founders freestyle, I always like to offer I love having founder episodes, and I do the founders freestyle, at the end where I give you give you a little bit of time to vent or reflect or thank people or I don’t know what what stood, out what we forget, like, go ahead. It’s your mic first.


Matt Martin  41:19

Love it. Yeah, I mean, you know, their. Oh man, freestyle, like you go into a bunch of different directions.


Matt DeCoursey  41:26

And it has in the past, trust me.


Matt Martin  41:28

That, you know, it’s really easy to get heads down and kind of the competitive nature of building a business. And I think you know, any of us from small business owner, somebody who’s trying to run a venture-backed startup to somebody who’s run a fortune 500 business, I mean, you kind of have to have a screw loose. I mean, it’s, it’s stressful, it’s hard. The journey can be long, and there can be long days. I have found that one of the things that I really anchor in is just building a phenomenal team. The folks that I get to work with, and I’ve had the privilege of hiring are just amazing. I mean, I, you know, I cannot build this, I literally could not build this, to your point earlier about how hard some of this is technically. You know, we have some incredible people, both on this software development side, the marketing side, the sales side, and I’m just coming off of off site where we brought the whole company together, spent some time together. And just remembering that human side of it, building that team up helping coach them to become a great member of the team, helping to further their career and observing what they can do. It’s really pretty awe-inspiring, and in what it’s what makes for me, the day to day, the week to week, really energizing, really fun. Of course, we get to build great product, we get to ship to customers, I love seeing that impact. I know that will be a huge, huge business that every business owner will want to deploy. But in the meantime, you know, seeing people thrive and just, it’s just awesome. I feel really privileged that I get to do it.


Matt DeCoursey  43:01

Yeah, and you guys are doing a great job. You know, I think that the amount of capital you’ve raised, which we didn’t mention, you talk about things we forgot, I’m showing 76 million in raise. So that’s that’s a that’s a big validator for what you’re doing and the importance of it going forward. And you know, speaking of which, like, I think in this modern age of technology, and all of the mainstream niche and integrated solutions that you can get like you owe it to your your team and your company to find things that also focus like there’s nothing more annoying than a mixed up confusing schedule or calendar. Am I supposed to be here? Am I supposed to be there? Where is this? Is this publicly facing? Can I, you know, go in and see a lot of different things and stuff. And, like, you know, I really do have a once again, a strong appreciation for the complexity of what you’re doing because it’s like, I don’t know, I just remember when we built the the conflict detection and the which is also your double-booking protection, because double booking is the same as missing a booking in many cases. It’s an error. It’s an error that doesn’t go over well. It doesn’t make the client or the user feel good about what they’re doing. In fact, it makes them look like an idiot. So you try to avoid that. But, but yeah, but you look at these tools that are out there that can, that can just make things feel a little smoother and less congested inside your company. And they are worth investing in. It’s you know, you can look at things oh, it’s seven or $10 a user and I’ve got 300 people, you will spend more money on that the first time you mess up or miss schedule or over book or under book or move something. You’re going to spend that much on efficiency. Don’t be the founder and CEO that doesn’t try to save a little bit of money through efficiency. I, I’m just telling you saving money is making money and your your people are in too many meetings probably. And I love that what you’re doing with Clockwise was actually putting in blocks of focus time. Yes, you know, like, I got to kind of do that manually myself. I just blocked spots, I can get your book, you can just create a block pretty, pretty quickly, but you gotta have, you got to go in and do it. You got to have the wherewithal to do it. And you got to also kind of like understand being able to put focus time and to get things done is an important part of accomplishment. So, well, here we are, man, we are out of time on an episode that we talked a lot about time. So, I’m gonna catch up with you down the road, Matt.


Matt Martin  45:39

Great. Thanks so much for having me, Matt. Really fun conversation and it was helpful for people out there.


Matt DeCoursey  45:43

Yep, see you down the road.