Founders & Friends with Scott Orn

A Startup Podcast by Kruze Consulting

Startup Podcast by Scott Orn

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Posted on: 08/31/2020

Matt Martin on Clockwise's smart calendar assistant that frees up your time so you can focus on what matters

Kruze Consulting's Founders and Friends Podcast · Matt Martin on Clockwise's smart calendar assistant that frees up your time

Matt Martin

Matt Martin

Co-Founder - Clockwise


Matt Martin of Clockwise - Podcast Summary

Matt Martin tells the Clockwise origin story, beginning with RelateIQ. Then Matt shares how Clockwise optimizes your calendar for thinking time via smart meeting re-scheduling.

Matt Martin of Clockwise - Podcast Transcript

Scott: Hey, it’s Scott Orn at Kruze Consulting and welcome to another episode of Founders & Friends. And before we start the podcast, let’s give a quick shout out to Rippling. Rippling is the new cool payroll tool that we see a lot of startups using. Rippling is great for your traditional HR and payroll. They integrate very nicely, but guess what? They did another thing, they integrate into your IT infrastructure. They make it really easy for when you hire someone to spin up all the web services in their computer. Which sounds like not a huge deal, but actually we did the study at Kruze. We spent $420 on average just getting a new employee’s computer up and running, and their web servers up and running. It’s actually a really good deal, it saves a lot of money. And the dogs are eating the dogs. We see a lot of startups coming into Kruze now using Rippling. So please check out Rippling. Great service. We love it. I think we have a podcast of Parker Conrad. You can hear it from his own words, but we’re seeing them take market share. So, shout out to Rippling. And now to another awesome podcast at Kruze Consulting’s, Founders & Friends. Thanks.
Singer: (Singing) It’s Kruze Consulting, Founders & Friends with your friend Scotty Orn.
Scott: Welcome to Founders & Friends podcast with Scott Orn at Kruze Consulting. And today my very special guest is Matt Martin of Clockwise. Welcome, Matt.
Matt: Thanks for having me Scott. Happy to be here.
Scott: Oh, this is a pleasure. I’ve been looking forward to this one. I told Matt, I sent Matt an email before we go on that I was going to have to calm myself down here and not get too overly enthusiastic. Matt’s the founder at Clockwise. Do you want tell everyone about your journey and how you had the inspiration for Clockwise?
Matt: Yeah, absolutely. And I have to start by saying Scott, that we’ve only had a couple people make YouTube profiles of us before. So, we’re huge fans of yours as well, that’s awesome to see.
Scott: I’ll give the quick, Clockwise allows you to dynamically rearrange your schedule and the schedule of people that you work with. So, it frees up a lot of time in your calendar. So, I started using clockwise and all of a sudden, I had these one-hour, two-hour blocks of time where I could actually think and actually write and get stuff done. Instead of half an hour here, half an hour there. So, anyone that gets interrupted a lot, you know what this is like. That’s been my entire time at Kruze Consulting. So, I started using Clockwise and I was like, “Oh my God, this is amazing. It’s a new world.” I like to do videos. So, I recorded a YouTube video talking about you guys.
Matt: Yeah. Music to my ears. Our mission is to help the world make time for what matters. And we’re happy to hear that we’re doing that for you. Zooming back out to myself and a little bit of the story of Clockwise. I grew up, I love building stuff. I grew up building websites. I was a huge Apple nerd before that was a cool thing. Before Steve jobs came back, making HyperCard stacks. And I came out to the Bay area about a decade ago after bailing on an early career as a lawyer. Made the hard switch back to tech. And worked at a variety of startups small, medium, large. And ended up at a company eventually called RelateIQ. And RelateIQ is an important touch point for us as a company because it’s where some of the inspiration for Clockwise comes from. But it was also just as you had mentioned Scott it was a hot bed of talent, just incredibly great people. And it’s where I met my co-founder Gary Lerhaupt. He was actually my boss at the time. Very first engineering hired there, VP of engineering post acquisition. I was heading up front end engineering and we were purchased by Salesforce in 2014.
Scott: By the way Kruze Consulting was a proud subscriber to RelateIQ. It was revolutionary that you could send someone a link or send them the times that you had available. And they could just book it, oh my gosh, talking about time savings there too. So, I followed the RelateIQ story for a really long time. Before turning on the mics we were reminiscing because I used to work with Elise, who was one of the people that you worked with at RelateIQ. She started a company called Stride Software, it was a Kruze client for many years. So, we have a lot of common friendships and I really respect the journey that RelateIQ did. It’s pretty awesome.
Matt: Yeah. And a small shout out to Elise Bergeron just incredibly talented if you ever have the chance to work with her. So, at RelateIQ, a little bit of background for your listeners. What we did is we connected primarily to email, and then we would use the analysis out of the data in your email to supercharge a CRM experience. So, you had to do less manual data entry. You could more easily collaborate with your colleagues, fantastic product. It was acquired by Salesforce, as I said, and it always happens, post-acquisition, people start to talk about different ideas that they have. We had, I think almost a dozen different companies spin out of that early crew at RelateIQ.
Scott: Amazing. Amazing.
Matt: I know. Out of 80 people at the time of acquisition, I think there were about a dozen companies. What I was seeing along with my co-founder Gary is just nothing new, I think, to anybody in your audience. But just how difficult it is to get time for your priorities in the modern work environment. It’s so easy to slip into this reactive flow where you’re bouncing from meeting to meeting. You’re trying to sneak in email triage in different parts of the day, respond to Slack messages and not having that time to actually go proactive, to do the really difficult parts of your job. The idea just stuck with me because a small anecdote here, I would every afternoon I would go to this coffee shop in Palo Alto. And I would always see members of my team that were sitting hunched over a coffee table.
Scott: I love it. I love it. That was like a getting away kind of thing and actually getting work done.
Matt: It wasn’t always the same person, but there was always somebody. And I started to ask them every time I’d see somebody on my team I’d say… It’s a startup, “We have Aeron chairs and nice desks a block away. Why are you hunched over at a coffee table?” And the answer is always, “I’m just trying to get work done. I’m trying to keep in my flow and try to get people out of my space.” And you see that enough times and you start to look at what is getting in their way. And it’s this constant drum beat of meetings getting popped onto their calendar. An interview, somebody tapping on your shoulder, putting you in a room. People started to take work home with them. It hurts morale. It hurts productivity. I think the real realization for us was, A, it’s a personal problem; B, it’s a universal problem, but C, the real insight is that as personal as time management is… As much as me going to a coffee shop is a personal experience. It changed the flow of my day or me getting on a podcast with you this is what I live. Inside a modern environment the real blocker is at the network level. It’s the interchange between people. I can be the best master of getting things done. And if my boss slaps a event on my schedule in the middle of the afternoon, that’s it I’m going, there’s nothing I can do about that.
Scott: Well, instead, another way, like that network level, it’s a problem that everyone has. So, what Clockwise does it doesn’t just improve my life, but it improves my coworker’s life too. Because they have the same exact problem they want to get work done too. And that meeting that I have, that I schedule with them it may be inconvenient for them. And so, by making that dynamically changed, it just improved to people’s lives or three people’s lives. I was telling you before I turned the mics on one of the things I love about it is that the more people I invite the Clockwise, the stronger it gets, the more benefit I get. And that’s the very definition of a network effect. You got to be so fired up because your growth is probably insane right now. Because I think I personally invited 10 people inside of Kruze Consulting to start using it, and now they’re using it and they probably invited another 20 people to start using it. So, it just makes everybody’s life better.
Matt: Yeah. That is one of the core principles of the product. And one of the amazing things about working in this space is that it really does… It’s not networks effects in that it’s beneficial for us as the business Clockwise to have more people on, it’s beneficial for every new user to get more users on. And to your point, the growth really has been pretty tremendous. We’re completely virally distributed. We’re still a relatively small team and we don’t pay anything for advertising or anything. It’s all word of mouth and people bring it into their organization. And it’s precisely that Scott is that sigh of relief. It just like, “I got an afternoon back.” And who doesn’t want that?
Scott: I was telling you that after our podcast because of Clockwise… And for people that don’t know, I think it runs at 4:00 PM the day before. So yesterday at 4:00 PM, it consolidated all my meetings today. And so, there’s two software specs I have to write. We have two internal improvement projects that we’re going to build next week, probably start on. But after I’ve finished the specs for those, there’s no way I would have time to actually write… That’s not just email triage. That’s real thinking, and probably screenshots, and arrows and workflows that your product is going to let me do today. And it’s like, “Oh my gosh.” And you made the point earlier that people take work home when they don’t get a chance to do it. That’s such an amazing point. And at Kruze, we really promote work life balance. The days of we do not want people getting burned out or burning themselves out. And so, we want them to have balance, but you know what, honestly, I probably would have done those software specs tomorrow. And instead I get to play with my kid. I would probably feel guilty the whole time I was doing it. And now I just get it done on a reasonable time frame.
Matt: The mission at Clockwise really is to help the world make time for what matters. And I think it’s one of the things that really excited me about this space and about devoting a huge part of my career to it. Is the ability to have a piece of software that simultaneously helps organizations be more productive, higher velocity. But also helps individuals not just feel like they can finally state what they need to do, but actually have it respected. Because there are all these silent preferences in the organization they don’t live anywhere. Like the preference that you need to get home to spend time with your kids. Maybe people know that about you because they work with you. But when they go to schedule that doesn’t exist anywhere.
Scott: The other thing that I think… These silent preferences is such a great term or said another way Clockwise gives me permission… It allows me to give myself permission to block time off. Like for example, I never take lunch. I used to never take lunch, but since I started using Clockwise, there’s actually a feature in there that says do you want to break for lunch? And how long and between what time periods. And now every day for the last… Because I’ve been using Clockwise probably for six weeks, maybe two months. So, two or three weeks ago, I turned that on. And now I just take a breather for 30 minutes, and it’s a little easier because I’m at home. So, with COVID, I can just make lunch. But I sit there, do not do any work. I don’t eat at my desk; I don’t read anything; all I do is just decompress. And what I’ve found is it makes me so much more productive. It recharges my decision-making engine in my head. Without that permission and default setting that Clockwise enables, I just would have never done it. I’ve worked here for five years. And I never get it ever. It’s crazy.
Matt: There’s a lot of magic to being able to offload some of the, for lack of a better word, social complexities of this stuff onto Clockwise. And we’ve discovered that, it’s very intentional. Things like lunch, people, it’s too bad they feel this way but it’s human. You feel like you’re being selfish somehow by stating that you need lunch on your calendar. And it’s not selfish, it’s important. You need to have you recharge.
Scott: [crosstalk] that somehow, I got to work thing. But I did get away from it.
Matt: And it’s just easier to have Clockwise create the space for that. And then as more people join, it creates the shared dynamic where it’s like, “Oh yeah, of course clockwise makes time for lunch.”
Scott: The other feature or the other thing I like is, and this is I think in a lot of calendar programs. But because you guys are moving stuff around, it’s really helpful in that I can set the parameters of my day. And I was someone who was guilty of despite having a young child, if someone really needed to talk to me early in the morning, I’d usually do it. But now what Clockwise does is takes that meaning and moves it out of my two early zone. And because I don’t have to do any work to do it. It finds a zone that works for me and the other team member. And so, it saved me from this is like… Sometimes I joke Google Maps must have saved so many fights between husbands and wives driving. Do you ever think about that? So, Clockwise actually saves many fights slash stressful moments with either my wife or my kid. It would be with my kid because my kid’s just doing something, and my wife would be getting mad at me because I’m trying to go to a call when I shouldn’t be going to a call. So, there’s this relationship preservation that you guys are doing.
Matt: Let me share this use case that my co-founder uses Clockwise for. And it’s a little bit of hacking together all of our feature sets. So, you have to be a pretty pro user, which of course my co-founder is.
Scott: I’m getting there. I’m getting there.
Matt: We have a feature called personal calendar sync. And what this does is I have a calendar with my spouse where we share different family obligations. And different people have used this in different ways. But what it does is one step beyond what you can already do in Google Calendar Outlook, which is it actually sinks in real times, the events from your personal calendar to your work calendar.
Scott: Very nice. Very nice.
Matt: What my co-founder has done with personal calendar sync is he’s actually made a childcare calendar with his wife. Literally she’ll have a video conference call, so Gary has to be on childcare duty from 1:00 to 2:00. She can just put it on that Google Calendar, that’ll get synced to his work calendar. And then here’s the kicker, Clockwise will then automatically move meetings off of it because it sees it, and it will auto pilot away. So, she just changes the childcare and then all of a sudden, his work calendar responds to it.
Scott: Especially in time of COVID where everyone’s like… We’re very lucky in that our nanny is still operational. But there’s a lot of families that have lost their nanny with small kids. And so especially a lot of Kruze team members, actually, because we have a remote workforce. People who have small children like working at Kruze especially because they have flexibility in their day. And can be at home and get rid of the transportation cost to work. But if you don’t have childcare trying to work with your two-and-a-half-year-old in the house really doesn’t work. So, one of the spouses is having to watch. So, one of our team members has been doing an 8:00 to 11:00 PM shift just to be able to get his work done because he’s doing a lot of childcare during the day. So, I can see that feature being so helpful because if Paul needs something moved around, or Paul’s wife needs something moved around Clockwise can just handle it for him.
Matt: The childcare complications with COVID have just been very intense for a lot of our users. And so, any way that we can help, we’re always happy to do so.
Scott: It’s amazing. And I don’t want to give away any secrets or something like that, but how were you able to network these calendars. I know Google calendar has open APIs. I’d always heard Outlook was pretty difficult, or Exchange was pretty difficult to work with. How did you guys make that technical leap to be able to put all this stuff together?
Matt: Well, one benefit that we had is that we had done elements of this at RelateIQ as well.
Scott: That’s true.
Matt: The primary point of integration was more on the email side than the calendar side, but it’s a shared API for most… You’re working with Google or you’re working with Microsoft and I have the scar tissue on Exchange. Definitely. [crosstalk 00:16:50].
Scott: There was a company called [inaudible] that I was always talking to back in the day, and they really demonstrated how difficult Exchange was for me. That’s been stressful even just thinking about it for your company. You guys made it work like it works, right?
Matt: Yeah. At a technical level I could go really, really deep here and so feel free to press at a deeper [crosstalk 00:17:11].
Scott: Not really. I know that too but I don’t want you to give anything away either because you guys are a business, and you need to make money and be profitable and all that stuff.
Matt: But what we do is it is quite intense. We are creating our own visibility layer onto the calendar completely on our side. Because what Clockwise does at the core is we’re processing your calendar and scoring it almost every minute of every day for a priority fit.
Scott: Wow.
Matt: And it’s a priority fit based on the content of the meeting, who you’re meeting with, when you tend to have meetings, the inferred preferences that we pull out of the data, but also your stated preferences. So, if just by way of example, if you are jammed on Friday and you only have 30 minutes from 12 o’clock to 12:30, where you could possibly have a lunch and somebody schedules another meeting there, we’re going to penalize that meeting.
Scott: That’s awesome, that’s amazing. It’s almost like a defensive line or offensive line protecting your lunchtime.
Matt: That’s right. But we do that across dozens of sets of preferences. And the cool thing about Clockwise at the core is that while we have manifested those preferences as specific ways for the users right now, it is very generic in how it’s actually engineered. So, you could imagine in the future, you might have a preference, and by the way this is not on the roadmap, but just to illustrate how specific you can get. You might have a preference that I have my most important outside client is Kathy at IBM. If Kathy at IBM is anywhere on my calendar that’s the number one preference. And so, you can gear in those knobs, however you want. But the system itself is very generic into scoring the priority. And then using that to represent how are we going to rearrange things in order to get the best output. Not just for Scott, but for everybody on the meetings.
Scott: Yeah, that’s really cool. I like that because we’re client service. I always tell founders they have the bat phone, they can just call myself or things like that. Because I do make time for our clients like that. So that is really cool, picking up on those little subtleties. And we want to talk about the Series B in a second, but if I may, the only other feature request I’d love to make would be a scheduling link on Calendly or RelateIQ because it would be all combined in one system. But I was thinking about that before we got on the podcast. I was like the same virality I initiated inside of Kruze Consulting just because I invited people. That will unleash a whole other level of virality amongst all the Kruze clients. There’re 250 clients that will start getting me my Clockwise link and then all of a sudden, they’re going to be on it. I’m sure it’s super beneficial to you, but it would actually make my life a lot easier too.
Matt: Well, I definitely have good news for you it’s something that we think about a lot.
Scott: All right. [crosstalk]
Matt: We’ll get there. One of the things that’s interesting about Clockwise that we’ve learned over time is because we are providing value at the preference layer… And because we’re providing layer at, “What does Scott need?” The level of complexity for new features is a little bit higher, not insurmountable, but when you think about external scheduling and we’re thinking about this a lot. What we want to provide for you is of course a link scheduler, but something that layers onto that, just nudging, according to what you want to do. If you have a founder and they need to meet with you anytime of the day, that’s a priority, of course they should have access to that. But all things would be equal if they can do that at a time that doesn’t Swiss cheese your afternoon, that’s even better. And so, building the product experience to nudge them in the right direction is what we think a lot about.
Scott: I’m sure it’s super complex because you’re also layering in all of their preferences and their organizations unsaid preferences… But your network effect is going to get insanely big that’s really cool. Maybe talk about the Series B a little bit. Like congratulations, first of all, that’s a lot of money and I’m sure it was really hard to do. But you probably have great numbers, and you’re looking good, and you’re an experienced team. How did it go down, how’d you make it happen?
Matt: Well, this is an interesting story because we started to form this relationship it started to raise it right as everything was falling apart in terms of COVID and shelter in place. Looking back on it was a fascinating period in order to go out and raise new capital because nobody knew what was going on.
Scott: With the stock market with valuations.
Matt: Oh man. Yeah. Yeah. I feel like we still don’t know what’s happening, it’s all over the air still but it’s a little bit more solidified. And what occurred was I’ll try to make this short and sweet, but essentially, we were capitalized to be able to last out the year and end at 2021 just fine. So, we weren’t thinking about raising anytime soon and the growth had been truly fantastic throughout 2020 and continues to be. So, we thought, momentum is there. Let’s just sit tight. We’re going to continue to go. We know what our product roadmap is, we’re locked in. But the growth had teed off a bunch of VCs because they have investments-
Scott: They’re using it. And they’re probably using it.
Matt: Yeah, that’s right. And so, they were seeing it inside their companies. They’re seeing it on their calendars. And so, a one investor specifically Bain Capital Ventures. And I don’t mean this to sound arrogant at all. I think a lot of founders will empathize with this. You tend to just get a lot of inbound discussions from VCs and you discount an email… It doesn’t necessarily mean that there’s intense intention-
Scott: I was an associated at a VC firm too. So, I know, you reach out to a lot of great companies, you want to have the conversation because you’re gathering information. It doesn’t mean the founder wants to have that conversation.
Matt: That’s right. Yeah, that’s right. And it doesn’t mean that a deal will happen or anything of that nature. I had been very used to just batting those away because I wanted to focus on product and we weren’t thinking about diving in. But then Bain actually started to do due diligence on our customers. And we caught this because one of our customers said, “Hey, why is Bain Capital Ventures reaching out to me.” And we’re like, “Oh, that’s interesting.”
Scott: That’s a little aggressive actually, but hey.
Matt: It is. But you know what? I really respected it because when we started conversations, they came to the table with stuff that was informational for us. They actually brought information about, and we’re a very customer centric company-
Scott: That’s a really great observation. Like they were almost like a market research survey for you. And giving you that for free.
Matt: And of course, they were doing it in order to formulate their thesis about us. But they were very transparent with it. They were very helpful in terms of coming to the table. It made for an interesting conversation, and it was just a really great way to break the ice. And then I got to know Ajay Agarwal there. We basically got to know each other over Zoom, which is an interesting process in of itself. And there were a couple other firms that I was talking with relatively intensely who had the same insight. But Ajay and the team that he was working with at Bain Capital Ventures put themselves in pole position with the market research that they had done with our customers. And we set up a bunch of meetings. What’s interesting Scott is when we raised the A, we were running around Sand Hill Road all the time. It’s nice that the VCs are all in one place.
Scott: This is the point I’ve been making to some of you, I’ve actually been more active on business development during COVID than before because I can do without the transaction cost. I think this is where you’re going with this, the drive over to this meeting, and grab a parking spot, and then grab coffee and then do all these five things. Actually, takes a lot of time, where with Zoom I can actually just touch people and talk to people so much faster. It sounds like that was what was going on with your VC round.
Matt: Totally. It reduces that complexity where you have to… And on both sides. So, it’s not just for me that it reduces the travel time on their side. All of a sudden, partner meetings can happen any day of the week. They don’t have to be on Monday, but it does up the intensity because now you’re just go, go, go, go, go for basically a week, I was just like running mad.
Scott: We do a lot of fun funding. It’s like how it is, but that’s just part of life. That’s part of being a founder. You got to take the money when it’s there. Especially for you guys, you would have been safe through all 2021, but who knows? We were all fortunate that the stock market came back during COVID, which meant VCs felt good about writing checks. There was definitely a six-week period where no one knew what was going to happen with evaluations and everything was locked up. When that spigot opens up, it’s your job as a CEO to make it happen.
Matt: Yeah, that’s right. It’s interesting to talk about the fundraising in this context because it was so uncertain and it was a new experience. For us, I think you also have to be really careful as a founder, as the leader of a company. The capital in is critical because it’s existential, but it’s just fuel. The challenge is still the same. We’ve got to deliver for our customers. It allows us to grow faster to hire and the capital is essential, but the objective is still, we want to help people make time for what matters. We want to deliver a great product.
Scott: Well, and the way I think about it with a company like yours, I don’t want to put the carpet for the horse, but it feels like you have a winning product. So, you’re spending way less time, trying to figure out product market fit or try to figure out, “Can this work or will this work.” It’s always an obligation to raise money, but you owe it to not just the employees and the company, but all the users. We can all use Clockwise for two days and know it’s going to be very, very helpful. So, like, “Hey man, hey Matt, don’t let me down… Don’t let Scott Orn down.” I need this. I think it was smart. Have you guys even got together in person yet, or is it still all Zoom with the pandemic.
Matt: I did have the good fortune of… I met Ajay in person for the very first time, the day we closed our office for shelter in place. So, we did have one meeting in person, but I’m still waiting. We’re both very eager to share a drink in person at some point in the future.
Scott: I love it. Well, hey man, this has been really good. And again, I don’t want to come across as super promotional. This is just a product I believe in. It’s made my life a lot better. And thank you for spending time with us. Do you want to give the audience… Tell them where they can find a Clockwise and how to reach out?
Matt: Absolutely. So, if you’ve liked what Scott and I have been talking about, I would love to hear from you personally. Feel free to email me directly at Matt, M-A-T-T @getclockwise.com, G-E-T clockwise.com. I’d love to talk to early founders, if you’re starting something out. I love to talk to people who are thinking about time management, or just customers who want to talk about the product. And then if you want to install Clockwise and get up and running. Completely easy to do, it takes all of a minute to get it up and running. You just connect your calendar. You go to getclockwise.com, G-E-T clockwise.com or just Google Clockwise. You’ll find us. You’re going to be saving time in a matter of minutes.
Scott: It’s really fast. If I can just put a little plugin. Before you even really get it going, just invite three of your close coworkers. Because it actually works a lot better if a bunch of people are using it. Our whole onboarding and sales team uses it now and it’s so much easier for everybody. Well, congratulations. Especially in the startup world, there really are no overnight successes and your overnight success of like… It’s perceived maybe that Clockwise is an overnight success, but if you really rewind the tape all the way back to RelateIQ. And even before that, you said you were a lawyer before we were recording, there was a long journey to get to this point. And not everyone gets to this point, so it’s really special. So, enjoy the journey and I’ll look for that little link, you’re going to really make my week, as soon as I get that scheduling link.
Matt: Awesome. We’re excited to do that for you.
Scott: Awesome. All right man. Great talking to you.
Matt: Thanks so much, Scott.
Singer: (Singing) It’s Kruze Consulting, Founders & Friends with your host Scotty Orn.

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