Despite early interest, Matt didn’t initially pursue a career in computer software because he didn’t have any role models for that path.
An interest in politics led Matt to start a successful blog, MN Publius, giving him first-hand experience with the power of the internet as an information sharing platform.
Initially, Matt’s diverse career path was a barrier to getting his first job in software engineering, but once he got his foot in the door that experience proved to be a benefit.
Clockwise was born out of the idea that time is a rare commodity, so it’s important to protect and enhance your use of time in your work and life.
IVAN STEGIC: Hey Everyone! You're listening to the TEN7 Podcast where we get together every fortnight and sometimes more often, to talk about technology, business and the humans in it. I'm your host, Ivan Stegic.
My guest today is Matt Martin, who is the co-founder and CEO of Clockwise, a service that manages your calendar for you so that you have more dedicated focus time in your life. In addition to being an entrepreneur, Matt is also an attorney, and a Minnesotan, who has provided political analysis for various publications. Hello, and welcome to the podcast, Matt. It's so nice to be talking to you.
MATT MARTIN: It is fantastic to be talking to you, Ivan. And it's really fun to be on a Minnesota centered podcast. This takes me back and I am excited to be here.
IVAN: It's lovely to have you on. Tell me about how amazing the weather is in California would you? Because you're out there.
MATT: It is a very typical San Francisco day, which means that the fog has rolled in and it's just slightly chilly. It's kind of like light sweater weather, which is about par for the course over here.
IVAN: So, I found out something that I didn't realize was a thing this week. Gray May and Gloom June, I think. Do you know about this? Is this California terminology for May and June?
MATT: I actually have not heard about that Ivan. Although having lived here for a number of years now I can definitely pattern match off of both those statements being true.
IVAN: [laughing] I didn't know it was a thing. I just thought it was always sunny out in California.
MATT: It is not always summer, and it is not always warm. The kind of apocryphal quote is “the coldest winter I ever spent was a summer in San Francisco”. Much debated about whether Mark Twain actually said that. But it is true. It is remarkable how August can be the coldest month of the year here just the way that the fog can play.
IVAN: Okay, clearly, people like Mark Twain have never spent 30 degrees below in Minnesota in the winter [laughing] if that's the coldest they ever got.
MATT: We both know that's not even close to true, but it's a nice quote. [laughing]
IVAN: That's awesome. Well, let's go back a little to where you grew up, which I understand is somewhere in Minnesota, and where you went to school. So tell me about that.
MATT: I was born at the Fairview Hospital, around Southdale in Edina. My first home was in Bloomington. So, I grew up in Bloomington until I was five. Both my parents are from the Twin Cities and my dad actually grew up not too far from that home. We moved out to the western suburbs, when I was around five years old, moved out to Medina, Minnesota, on the edge of Plymouth and that is where I grew up all through elementary school, middle school, and my parents still live there today. I moved out to the east coast when I went to college, but I also came back to Minnesota after college.
IVAN: And you went to one school for your whole education before you went to college. A school called the Blake School.
MATT: That is correct. Yep, I am, for better or worse, and I'm sure that there are many opinions out there in the audience on the Blake school, but I do have to say I feel lucky to have gone there and really enjoyed my education there, enjoyed my time there and spent all the way from first grade to 12th grade at the Blake school.
IVAN: So, you're what they call a lifer. Right?
MATT: That’s right. Well, now Ivan, this is actually much debated. Funny enough, I didn't go to kindergarten at Blake. Here’s my argument, I didn't go to kindergarten anywhere. I went to Blake and they put me into first grade. So I think I'm a lifer. But the hardcore among us might disagree.
IVAN: Okay, I totally can see that. Yes, I think I would agree with your logic. If you didn't go to school anywhere, and you started at Blake as your first and you didn't need to go to kindergarten, then I would qualify you as a lifer.
MATT: That's right. And my wife reminds me all the time that I really missed out on kindergarten because I never learned how to share and that haunts me to this day.
IVAN: [laughing] So apart from not learning how to share at the Blake school, how do you think it actually did prepare you for college and for your life now and what you're doing now?
MATT: I think that one of the things is that I really truly find myself to be lucky in life in myriad ways, but as it comes to Blake, I had excellent teachers. It's not without exception. There are some areas of Blake's overall academic portfolio that I think are not as strong as others. But the teachers that I had there were really pretty amazing. I'll go all the way back to my first grade computer teacher. We had a computer lab in first grade.
For me, this was in 1991, so I mean not a tremendous time ago, but at that time, not all elementary schools had computers available to them, but we did. I had a computer teacher called Miss Kelly, and she really saw that I liked computers, that I gravitated towards it and really took me under her wing. I spent first through fifth grade with her, and I loved to go into the computer room. I loved picking up HyperCard. HyperCard, I still remember it. A light bulb lit up in my head what you could do there, and I actually ended up working for her over a summer, working with her in the computer lab. She headed up IT overall in Blake eventually.
So that was a big influence on me. I think the second part of it I would note is, really great teachers know how to get their students excited, they know how to pull them in to not just the subject, but the curiosity to learn about what their world is like to learning about how they can apply their interests to the world around them. As trite as it is, it is kind of a trite phrase, it really does start a lifelong process of learning.
For me, I'm a very curious person, I love to learn, I still love to learn today, and it brought me through a couple twists and turns in my career so far, but I love starting a company partially because so much of my job is learning new things and learning how to function in new areas that I've never had exposure to. So I think that that process started early with me and I'm really grateful for it.
IVAN: Do you feel like you thought you would be in computers when you first had that first grade class with Miss Kelly? Did you know, that's what you wanted to pursue or did you want to be something else when you grew up?
MATT: I did not. And I'm curious Ivan what this was like for you because for me at that age, in Minnesota, the role models that I had weren't computer centric. Computers felt to me like a fun toy almost. It felt like something that I would go to that was just really cool and was a side interest. I never saw the career path. I had no software engineers in my life. I had no creators.
IVAN: I think I feel the same way. I didn't have any role models, either, but grant it I was programming computers a little sooner than you were, maybe five or six years. It was the early to mid-80s when I got started. Obviously no internet, small Zedex Spectrum 48K. I also saw it as a hobby, I think. There weren't any software engineers. I did not study any software engineering, or any computer science classes in school or in college. Everything that I've learned has been for my own benefit, because I was interested in it. It'd be interesting to know how that compares with now because there's so many courses right now, and as early as kindergarten.
MATT: I think for me, I've always been a pretty ambitious person, for better or worse and there are real downsides to this. And so, I don't think that I had the courage when I was in high school or even college to pursue something just because I was interested in it and pulled into it or I might have had a different career path. It was for me, the lack of understanding and the lack of connection between that interest and a career path that I could grow into. So, I think these days again, for better or worse there are a lot of examples of people who have really had very interesting, compelling careers in computer science, in building software, that pattern matching today I think I probably would have gone into software much earlier.
IVAN: Yeah, I think I would have to. But, you spent the standard number of what, two, three years at Blake in the high school doing some college counseling, and I'm sure you had a number of schools that you were applying to. But you ended up going to Dartmouth, you ended up studying government. Tell me about how that happened, how you ended up in government studies?
MATT: That one is interesting. I wouldn't say that it was deliberate. I like so many other people who go to college, you go to college, and then you're expected to make a choice about what your major is, and I had no clue. I was actually debating a little bit about computer science, about economics, and that one for me was really just an interest level. I've always been fascinated about how people organize themselves, and the capacity for large social level change through systems of government, which for me is really about collective action. How do we get together as a group of people, and choose how we're going to shape our society and how we're going to shape the rules in society? I find that endlessly interesting. It's an intersection between history and public policy and kind of our aspirations as a people. So I just find the narratives and the stories and the history there to be so rich and interesting that it pulled me in.
IVAN: Did you know what your career path would be?
MATT: No, I did not. Another thing that happened at a similar point in time is that in high school I had gotten very interested in Minnesota politics. For me at the time, and this has changed a little bit, and we could probably spend a whole podcast series on this, but Minnesota had always had this very kind of pragmatic, progressive strain of politics. I wouldn't call it highly liberal, although there are certainly strands of that. I mean, there are strands of everything, it’s a large state.
But it was centered around, we can get together, and we can get stuff done. Like if we put our heads together, we can make this better for everyone. I think it is rooted in a little bit of a Scandinavian tradition, so you see weird things like the Democratic Farmer Labor Party and the DFL instead of the standard Democratic Party, and I love that. I love coming together to make things better for everyone. You know, Paul Wealdstone, saying, We all do better when we all do better, and that spirit of being able to come together and make things better for everyone, it motivated me and inspired me.
So when I went to college, I did find that in some ways leaving Minnesota crystalized for me, the exceptional parts of that tradition, and how that felt so functional in contrast to some of the things I saw in other states, and the comparative studies of how different state systems evolve was really interesting.
This is fun because most people aren't interested in this stuff and most people won't have the reference points, but your audience and you do, which is at the time I interned for Senator Dayton. I went to Washington, DC, and I spent a term in his office with him.
It was a great experience. I was talking to his chief of staff at the end of my internship, and I was saying, You know, this is great. I really love this. I love Minnesota politics. How can I stay involved? I'm in New Hampshire. I'm out in Hanover. How can I stay involved in Minnesota politics? And he said, and this is a good bridge to something else that we can talk about, but he said, You should start a blog.
IVAN: [laughing] So you took his advice.
MATT: I took his advice. It was such a funny piece of advice and it just hit all of the notes for me, because, you know, as we're picking these threads together, I had built websites, I love building websites. It was still a hobby for me at that time, but I loved it. It sounded so fun for me to get in. I like writing. I was really interested in staying connected. And so, while I was in college, I did start a website that was a blog. At the time it was Minnesota, mnpublius.blogspot.com, and then we eventually bought the dot com to just make it MN Publius, but that was a really fun experience.
IVAN: Tell me why you called it mnpublius.
MATT: So super nerdy, government major reference. The authors of the Federalist Papers when they were published, Alexander Hamilton who wrote most of them, John Jay and James Madison, they published them under the pseudonym Publius, so they did not individually sign the papers, they signed them all from Publius. I used Publius as a reference to actually a Roman citizen, but I used Publius and framed this as Minnesota Publius. At the time there was this website called Minnesota Democrats Exposed.
IVAN: I remember that actually. [laughing]
MATT: Yeah, and who we now know to be Michael Brodkorb, who actually I know personally; interesting guy. I actually have to profess I like him a great deal, he's an interesting guy. But at the time he was publishing that completely anonymously, so I thought, hey, you know, it'd be like, I want this to be a little bit more highbrow, like, I want to, I want to engage on policy, I don't want to just take people down. But I do want to write this anonymously, because I don't know where it's gonna go. And you know, Michael kind of carved the course for the right leaning side of it being anonymous and so I thought, Oh, what a clever reference Matt. [laughing] I was like, I’m going to use the pseudonym that they published the Federalist Papers on but it's going to be Minnesota.
IVAN: Well, this is a great piece of information. I have to be honest and say I did not learn that from listening to Hamilton many, many, many times as a musical. [laughing] But I did know that Hamilton wrote most of the Federalist Papers, so at least there's that. [laughing] So what do you think you were trying to accomplish? You started this in around 2005. It lasted through the great recession and Obama's first term. You faced a great deal of challenges. It ran for how long? How long did it last? And what were you trying to accomplish through these years?
MATT: I was super actively involved from 2005 to about 2010, and by super actively, I mean, for a period I was the sole writer, and then I was kind of the person who was managing it a little bit, and then writing among several other people. Then when I went to law school, I'll come back a little bit to why and what changed over that time period, but just getting to the chronology of it. When I went to law school, I wanted to break from it. It felt like a new chapter in my life, and I didn't want to carry it forward by myself, so some other folks picked up the day to day writing, and I kind of stepped back involvement from 2009 or so. Then I can't recall honestly when we finally shut the doors completely, but I wasn't involved at that point and there just weren't writers left. I think that was probably around 2012, 2013 or so.
IVAN: And was it revenue neutral? Or was it a money hole? How did it fund itself? Was there even a business model around it if you were doing it for yourself at the beginning?
MATT: At the beginning there was none at all, I was just doing it for myself. The initial motivation behind it was really the chief of staff in Mark’s office having inspired me to kind of think this would be a good way to stay involved, and it was, it was great. I find that writing is so important for clarifying your thoughts and also by writing you engage yourself in the issue at a deeper level than just talking about it. It’s really easy to have a back and forth about it at a high level but when you write you have to get into the nitty gritty of it. And so, for me initially, that's what it was, but then started to get some traction.
It was a very small community at that time and still is really. When you think about a state legislature, there’s not a lot of coverage of that, especially with the collapse of local news, even more so today there’s not a lot of coverage of it. And at the time I found pretty quickly I was getting an audience among kind of the Politico's inside Minnesota, so not really at a national stage but at a local stage, and that is, for a government major holed up in New Hampshire, that is catnip. It was so cool to be able to write something and see people who might be able to actually have an impact read it.
IVAN: Then talk about it.
MATT: Yeah. It was really, really interesting and how the web enables that in order to have that platform of your own creation, really interesting. So, it sort of gained more and more of a following and we found that when it came around election cycles, we would just get a spike of traffic. So, the business model, we did find that we could eventually sell ads, it was never self-sustaining. It was literally like Zach Stevenson, who's now a state legislator, out of Coon Rapids, he's in the house, and a wonderful person, he and I would write, and we would get, like pocket money. It was nothing or like, maybe, Zach, and I would buy a round of beers, but it was fun. We were getting this audience and we could talk to a lot of folks who were interested in talking too.
IVAN: Yeah, and very different times then times right now. So, I want to ask one more question here and then we'll move on because I have so much more to ask about. When you were doing this blog and selling a few ads to by yourself and your friends some beer, you had a certain number of issues that you were dealing with, a very different ecosystem of blogs and news and local news in 2005, compared to right now. If you had started this blog today, those challenges would be very different. Would you be discouraged doing it?
MATT: I still believe very strongly in the web as a platform, I think especially the open web. Being able to spin up a website and put words on a page that you can distribute to as many people as have internet connections is truly an amazing thing. I feel really lucky that I was born in a time where I have access to that, so I still have a lot of respect for that. I think one of the things that is tricky and, I don't know how I would react, to be honest, I'd like to think that I'd be above it. But I was 20, 21, 22, I was still pretty immature and that feedback loop that I had at the time of writing something interesting and seeing people who can make an impact read is a positive form. It had negative parts and I'm happy to talk about that. It's a positive form of the same sort of feedback loop that can happen on Facebook or Twitter, where you're trying to get an audience.
But the feedback loops now incentivized pretty bad behavior and so to get above the din of the regular conversation, you're incentivized to take a more extreme stance, to break through, to aggravate people so that you get a response to create conflict in order to entice somebody who maybe has an elevated platform to pull you in. And there was a little bit of that at the time.
One of the ways that we built our audience, I would go through the comments on other people's blogs that had a larger audience, and I would comment, but for me, personally, sometimes it was about picking a fight, and I want to embrace that. I did do that. But it was usually in the spirited way of picking a political battle instead of a personal fight. But I could easily see in this environment, how that could take a very negative turn. I would like to think that I would resist that, but I don't know. It's a different environment.
IVAN: Yeah, it's been sensationalized in this day and age. I feel like the fights you would have picked would have been over ideas and over political constructs and I don't see you as going ad hominem which I think is way too prevalent in our discourse today. If you don't agree with me, then we just go ad hominem and like that basically shuts the whole conversation down.
MATT: And this is something that I look back on and I'm proud of. There was a little ecosystem of more liberal bloggers, and we had a pretty big audience in that crowd. I think that in some ways we're a leader in some ways we were kind of the young kids that were like, Oh, these little guys, you know, why do they have more viewers?
But, uh, I get together with them periodically, and I liked a lot of those folks, but they viewed Michael Brodkorb as just the devil. Michael was sensational. I mean, he picked a few battles that I think we’re a little bit beyond the pale, but I would also go out and grab beers with Michael because we were in the same field, he really loved politics, and we found the internet interesting. I disagreed with him on almost everything, but he’s made some bad choices in his life, both inside and outside the blogosphere, but I consider him to be a good person at the core.
I think I would have resisted the kind of sensationalized ad hominem attacks that you see now. But you never know, those feedback loops are really strong, and it's really intoxicating, especially when you're young.
IVAN: Those endorphins are strong. [laughing] They really are. So you spent college working on your government degree, and then you went to law school. While you were in law school, I believe it was when you founded Inbode, which is how we met. What was Inbode? And why did you start another company?
MATT: There’s the part of me again going back to where we started a little bit is that long term just love of learning. I just can't put my hands down. So law school is very busy and I enjoyed it for the same reasons that we talked about with the government degree. I really enjoyed kind of the historical intersection of how people organize themselves, which is really what the law is all about, and researching that, and getting to know and getting to understand it. But I love creating and my very close friend, he’s still a close friend, his family is in kind of the mid-market of apartment rental management, and there's very clearly a hole in the market between tools that might help an individual kind of investment landlord or somebody who just has a couple of units, and a really large scale institutional landlord, of which there are many in the country.
And, after talking to a few people and doing some research it felt like a really interesting space. Now, that’s a little bit of hindsight 20-20 on the problem, because I think that if we had articulated the problem that way, we would have ended up in a different space. For myself and my friend at the time and coming to you, Ivan, we were kids who were in our early 20s. What we experienced was how difficult it was to find an apartment, and so we were trying to find this angle where yes, we saw that enabling the midmarket, rental owners would be a good business, we really wanted to solve the problem of how to find an apartment. And I think there is an intersection there, but I think that it was too diffuse of a problem to address.
IVAN: It was a really interesting problem. I remember when I saw you guys, and we talked about how you wanted to fix it, it made perfect sense that this would be something that would absolutely be a success in the market. And it was great to work with you then. We sort of lost touch after that project, and you ended up moving out to California and getting another job and working for a whole bunch of different companies before starting yet another company. So, tell me about why you moved out to California? And what led you to starting Clockwise?
MATT: I hesitate a little bit because there were multiple reasons that we moved out to California. The story that I'd like to tell you is that I was inspired, that I really wanted to get back into software, and that is true, but there’s a legal term, the “but for reason”, it means like but for this we would not have moved to California is that my wife was finishing medical school and she was looking at matching and the match process is really interesting. You rank where you want to go, and then you just get matched, and you go. And, if you don't go you basically have to take a year off. So, it's kind of this weird national matching system and she was debating whether or not to rank University of Minnesota one or to rank Children's Hospital of Oakland number one.
And I didn't love being a lawyer. I did like it, and we can talk about that, but it wasn't my life's calling and that was clear. I really loved my time that I spent with you and Charlie on Inbode, and I wanted to get back to creating and so when the opportunity presented for Ashley to just nudge that match ever so slightly to put Children's Hospital of Oakland number one and the University of Minnesota Children's System number two and roll the dice to see if maybe she gets her number one pick, I wanted to jump on that and she felt comfortable doing that too, and she matched here and we moved.
IVAN: Wow, that’s serendipity is what it is. Kind of little bit of influence from the things you can control, the levers you can control and, and out you went to Oakland.
MATT: That's right. The interesting thing about that serendipity is that it could have easily been Minnesota. I could easily be still an attorney at a large law \firm at, now I think Faegre, Drinker, Biddle. The name has changed several times. [laughing] But we moved out to California, and it was an opportunity for me to make a clean cut with law. I could just move, I had a clear reason for leaving, I had a clear reason for changing careers.
And one of the things that came out of Inbode was I did have some, not incredibly deep, but I had some domain knowledge in the apartment rental space. So, I went out to California and there’s this company called Lovely. It was at livelovely.com and doesn't exist anymore, but they were doing this better version of what Inbode hoped to be. It was a great portal for searching for apartments. The big innovation at the time, which is what Charlie and I wanted to do with Inbode, if you remember Ivan, is, at that point, and this might be crazy to some of the audience, nobody put the listings on a map.
IVAN: Right. [laughing] That was the feature that was Inbode, right?
MATT: Yes, that's right.
IVAN: Like the apartment search using a map.
MATT: That's right. And it sounds so basic, but it was like, nobody put it on a map. And in fact, it wouldn't be years until Craigslist had a map view. That’s what Lovely did, they put it on a map. They took a different approach than we were taking Inbode, but they had some venture capital funding, and I convinced them to take me on, talked my way into position there, and was off to the races.
Looking back, it was [laughing], you know, I don't know how they took the risk on me, but they saw something they liked and so they brought me in, and I got to do a little bit of business development, a little bit of product development, and then more and more software engineering, and bounced around a few different startups building out my software engineering credentials.
IVAN: So, there's an interesting perspective here because you talk about how you don't know what they saw in you, right? And you talked your way into it, and they let you do some business development. But you're a CEO of a startup company now that's gone through $18 million of Series B funding, right? You're on the other end of that coin now. So, I'm sure you can think back from the perspective of the CEO who was hiring you or the business manager that was hiring you and think about, Oh, this guy, he's got so much potential, we totally need someone who can figure things out. Right?
MATT: Yeah, and that’s absolutely well stated. There's a lot of imposter syndrome I think, in general, and in our industry specifically, and definitely in me where I feel like I have gotten lucky to have the opportunities that I've had, and I look back on them with a great deal of respect and admiration for the people who took some risks on me. But yes, I am in a position now where you look at that decision and it does seem rational. Here’s somebody who's hungry. Here's somebody who has an interest in the space. Here's somebody who can problem solve, who's tried it before. We don't know quite what to do with him but let's give him a spin. And we do that at Clockwise as well.
I love just whenever I have a platform or just talking about that transition, for those out there who really find software engineering interesting but don't have a traditional degree, that was a really tough transition for me. I have a lot of respect for the folks who do that. I want people to know that there's a path, but it is hard, and it takes some perseverance.
So, after that apartment rental site, I went to a legal startup, another person took a chance on me. But there's this difference that happened Ivan where when I was starting out in the Bay Area I looked like this kind of weirdo, like a lawyer who was really interested, high potential, would hustle, would take any offer they could find. But you could look at my resume and you knew that you were taking a bet on me versus when I got out the other side of the legal startup, I was a software engineer, I was a front end software engineer, but I had no traditional training, I didn't have a CS degree, so I got evaluated as a software engineer. And that transition was really difficult.
So, I would just fail a lot of those interviews. The thing that I would isolate for those who are kind of in this process and searching for themselves is, once you get your foot in the door somewhere, that's the toughest thing. I got a job at this company called RelateIQ, they took a risk on me, and then I was off to the races, because now I'm a software engineer. And so, perseverance, trying to find that first job through your network, trying to focus in on places that you really like and just beat down the door.
I found that a good way was maybe trying to de-risk yourself for the company by saying, Hey, let me contract. Let me work on a project with you before you take me on full time. I encourage those who really do want to get into software engineering, it's a great career. I love software engineering. You get paid to problem solve, and to troubleshoot on your own time with a keyboard. It’s great. Just grit, perseverance, it took me a while, and it was really hard to break through. I almost got lost in the wilderness and I was lucky to come out the other side with a career I'm really proud of. But it is tough.
IVAN: I wholeheartedly agree with the way you describe de-risking yourself for others. That's sort of what the process is to engage with TEN7. If we're going to hire someone, we have a contract to hire model. And we want to contract with you so that you know what it's like to work with us, but also so we know what it's like to work with you. When we do that on real projects a little bit at a time, we can either scale up or scale down depending on how it's working out. So that's attractive to me as an owner and as a company leader. So, I think that's a good piece of advice.
MATT: I would also say that for people who find companies like TEN7 and leaders like yourself, Ivan, if you see that contract to hire, I would jump on it, because what that represents is that somebody is willing to take the time to engage with understanding your skill set, and it’s actually quite valuable from the other perspective from the employee as well, because you might think, Okay, I'm on a contract, there's still a lot of risk here. I'm not full time. But there's a dual sided investment there that I think is really great. Whereas if you manage to get a full time position somewhere, full time software engineering position, that can be great, I'm not gonna say don't go for that. But you can also get lost a little bit, you can get thrown into the thick of it, and nobody's really checking in or taking the time to engage with you, at companies that don't know how to do this well. And so those contract for hire positions, those are just wonderful opportunities for folks who are trying to break through.
IVAN: And perseverance as well. If you don't get that first contract to hire, keep doing it, keep persevering to follow the desire that you have and learn and read and implement as much as you can.
MATT: Okay, Clockwise. [laughing]
IVAN: Clockwise. [laughing] So you RelateIQ, I think is what you said. And then you were at another company before Clockwise, and so tell me about that nugget. Tell me what got you started thinking about a new company.
MATT: So, a couple things. The company that I was at was acquired by Salesforce, and I actually worked my way up to Engineering management, and then managing managers. Another thing that I would note related to our last topic is that once you do break through, you'll find that your ceiling is higher because you have a diverse set of experiences.
And so, I found that entering a company, my weird past experience as an attorney and having formal training and having managed people before was a real asset. So, I end up in software engineering management, and two observations Ivan. One of them I think is relatively unique and the other is not unique. [laughing] The first kind of non-unique, non-insightful one is just inside of a monitor organization like Salesforce, it is so damn difficult to get time for your priorities. You just kind of play whack a mole with your schedule, people are trying to get time with you all the time, it's hard to find time to be proactive, it's hard to find time to sit down with somebody on a code review or think about next quarter strategy.
The schedule really kind of conspires against you. You have to take active steps to make that time for yourself. I'm a nerd on this stuff, I’m a nerd in a lot of ways, [laughing] but on productivity, I would try to coach people up on time blocking and different processes for making sure that you're blocking off time and you're auditing your calendar to make sure that you get time for those priorities that you want to set aside. And those are great, those are important; personal discipline, getting a process that works for you, I would counsel anybody to do that.
But, as personal as time is, when you're inside a large organization, or even a medium sized organization these days, you hit the wall of the organization’s schedule. You can be a master at getting things done. You can have a black belt and time blocking, and when your boss's boss schedules a three PM meeting with you, you're going to go. It doesn’t matter.
IVAN: Right, there’s no choice.
MATT: There’s no choice, yeah. So the cadence of the organization around you, the PMs that are taking time from you, the other folks that you're trying to collaborate with, the flow of Slack messages, the flow of JIRA tickets, all of this stuff comes together and creates an environment where, what I found, and this is the second insight is, time has really become a shared asset. As personal as it is, it is something that we are collaborating on. It is the core building block of how we orient ourselves inside of companies is having a shared asset of this is the time we have together and we're not treating it like a shared asset.
And what happens here, and this goes a little bit back to my government training is, it looks like a classic, there’s both a public policy and an econ concept of a tragedy of the commons, and a tragedy of the commons is both a real observed phenomenon, but also kind of an economic construct where back in the 1700s or 1800s, you'd have a central commons in the center of town, and it was usually used for grazing before these were turned into parks. It’s a shared resource for the whole town and if you don't regulate it, if you don't state who gets to use it when, you end up grazing all down to nothing.
The tragedy of the commons is that when you have a shared resource that's highly valuable, and it's not regulated, it ends up getting consumed by whoever can consume it fastest, or whoever can run it down the quickest, and then incentives are all off. It’s a classic scenario where you need regulation or government. Now in an organization, time has become a tragedy of the commons, everybody's taking from it because it's scarce. There are only so many hours in the day, you need to meet with folks to move your projects forward.
You need time in order to get your job done. And everybody's vying for it, but there's no coordination and there's no regulation, because we haven't embraced that as a shared asset. So stating it in a completely non wonky way and more basic is if we want more time in our day for what matters, we have to coordinate better. Inside of an office environment where you have tens, hundreds, thousands of people working together, that's a network problem. It's a network problem across those individuals, and for a network problem where you're trying to coordinate software's a really good tool. So that is the inception of Clockwise.
IVAN: And how do you make a business out of a Chrome extension? Because that's what the product is, right?
MATT: Yeah. So, it took us a while to slow it down. A couple of things here. I'm a front end engineer, I love building product. There's a part of me, Ivan, it pains me in my heart that we're a Chrome extension. [laughing] Pushing ourselves into this sidebar alongside somebody else's screen real estate, we initially were thinking of being a calendar and that's all to say that (a) that's not where Clockwise starts, but (b) it’s also a hard one, strategic choice, which is Clockwise is about building out that platform for coordination. We need to access people's time inside the organization.
We need to connect to calendars, connect to Slack, eventually connect to Asana or JIRA, to understand what your priorities are, what the flow of your day is, to get you onboard and understand how you want to manage your time. So the platform is really what's essential, and we found that the lowest friction way and the fastest way to gain adoption is, let's not reinvent the wheel, let's not build a calendar because people have a calendar they're comfortable with, let's just augment it and the best way to augment it is with the Chrome extension.
And that distribution methodology has really paid dividends because we don't have to convince somebody to switch, we just have to convince them to augment. And so, what happens in terms of business model is we get really broad based distribution. Clockwise is pretty viral. It is pretty viral inside of an organization, and we get a lot of users and we start to drive real productive time back to the calendar. We make people's days better. It turns out when you make people's days better, they're willing to pay you.
And so, we have a subscription model that is per user per month. It’s entirely a business tool, so this isn't something we ask individuals or consumers to pay for this out of pocket. The bill is usually footed by the team or the department or the organization as a whole and Clockwise is then implemented across the team or across the department or across the organization to help everybody coordinate better, and ultimately get a better schedule.
IVAN: It sounds like exactly what I need at TEN7, and I'm very excited to try it out in the next couple of weeks here. I know we are having a couple of little issues with it right now, but I'm looking forward to trying it out. The thing that really attracts me to this company and this product is the fact that it works best when you don't notice it. So, like even if it is a Chrome extension, that's okay. If I am magically having my calendar rejuvenated and rearranged without even knowing and everybody else is okay with it, and I'm getting valuable time back for my own needs, the fact that it's not there, that’s like magic. Right?
MATT: One hundred percent. And, you know, there's an interesting yin and yang here. So, on the one side, that's exactly what we provide. So, our setup is relatively extensive, because we want to get you set up correctly and get you setup, right. Completion of our onboarding is really high and it's surprising because our onboarding, and I’ll own this, is relatively long. We have a lot of tools that we can get you up and running with, but once you're up and running, you get the recurring benefit, day after day, without really having to monkey with much. You can come in and you can dial things in, or you can change it, but we just help you out in the background, which is magical, and that's the experience that our customers love and that's the experience that ultimately that they're paying for.
IVAN: How long has Clockwise been around? It feels like you’ve been missing from my life for too long.
MATT: So, the company was founded right around the beginning of 2017, so going on about four years here. But we've only been publicly launched for about a year and a half. I like to remind folks when they join Clockwise of this, which is that we're in the business of category creation, for better or worse, and there's a lot of better than this, but there is some worse. Category creation is really, really difficult. The upside of it is it's really exciting. We get to create something new that people haven't seen before. We get to imagine things from the purest of first principles. We get to create in the kind of the truest sense of that word. The downside of it is that we can't look over someone's shoulders. So RelateIQ, one of my past companies, we were building a CRM, a more intelligent customer relationship management piece of software.
And so, you know, anytime that we had a question about business model, or about feature set or about functionality or even about UI, we can kind of go peek over the shoulder of Salesforce like okay, what are they doing? Or we can look over at one of our competitors' bases and like, Whoa, what are they doing? With Clockwise, we really don't have any direct competitors. And then on the business model side, and this is a really tough one, this is really tough about category creation is that we're not a line or replacement spend, there is no existing budget on somebody's spreadsheet inside of a large organization that says, time optimization software, x $1,000 a month, and so we had to go, and we had to make the business case and we had to carve out budget for ourselves and we had to translate that into ROI for the business. And so, it's fun to be a trailblazer and I wouldn't have it any other way, I find it so exciting, and the team is remarkable. It is really fun. It's really hard, but it's really, really rewarding. But I do have to emphasize the difficulty of it, and so it takes some time.
IVAN: So, what do you attribute the incredible growth that you've had? I read that you do no sales and no marketing?
MATT: Yeah, well, that's changing a little bit, because we're seeing the growth from the early stage be so attractive that we're building out a little bit more of a marketing muscle, although that marketing muscle is really oriented towards a product lead growth model. So, there's kind of a new world of the Slacks, the Notions, the inner tables of the world where marketing is less about having a billboard and it's more about understanding the journey of your user and making sure that you're staying in touch with them at the right time.
And then on the sales side, we're just building out our sales team. So for those of you interested in joining [laughing] a very compelling company, we are expanding our sales team as well, because we turned on those revenue levers. But in terms of the growth, it comes back again to those strategic decisions around what's essential here. And one of the things that's essential for Clockwise is not that we own the whole UI, not that we're the complete calendar, but one of the things that is essential is that we build trust, because we're going to move your meetings, which is crazy [laughing].
IVAN: Totally crazy, yes.
MATT: [laughing] Totally crazy. And so, we need to build out the trust that you understand how the system works. And what that means for us is that we have to go person by person, and if you go person by person, if you're not hiding behind a sales team that pushes a top down, or if you're not looking at a centralized administrator to roll it out, you've got to really stay close to the user, and you've got to really make it something interesting that they're excited about using. It turns out if you do that, people like to spread it, people like to evangelize it. And lastly, it, of course, doesn't hurt that going back to kind of the core thesis around Clockwise and why we started it, calendars are networked, Clockwise exists on that network and so you can spread on that network as well, which has really been essential to our growth.
IVAN: Let me see if I can give a very short explanation of what I think Clockwise does, so that our listeners can understand and then you tell me if I got it right or not. So, you built this piece of software, and you started a company to do it. This piece of software connects to your calendar, you're using Google Suite, it connects your Google Calendar, and it gets used internally with the team or the whole company where you're at. You tell the software which meetings are important to you, when you would like to have focus time, which meetings could be moved, and presumably other people in your organization and on your team do the same thing.
And then you trust the software Clockwise to just go back in the background, and actually move meetings around so that you get larger swaths of time to yourself for focus thinking or for strategy work or for doing the work instead of being in the meetings? How's that?
MATT: That is dead on. Nicely done. We're going to hire you for our marketing team to make sure that you give the introduction.
IVAN: [laughing] That's amazing. Okay, good. I love this idea. Tell me about the expansion. What happens once internal companies or companies can fix their meetings internally? Do you start leveraging that network effect and go outside of your company with other companies or maybe with other software platforms like the Microsoft Office platform?
MATT: Yeah. So, stated otherwise Ivan, kind of synthesizing what Clockwise is, it’s a smart calendar assistant that frees up your time so you can focus on what matters. And so, we, exactly how Ivan stated, we open up focus time for you through moving meetings to better times, and you get a lot of controls, what we move, when we move, but we can help to do that across the organization. That gets better as more people inside our company use it. It's great.
If you're a single person and you come into this, nobody else in your company is using it, you’re going to get a lot of value out of Clockwise. We have a lot of features that are great for just a single user, whether that's personal calendar sync, where you can pull in your personal calendar, your work calendar, completely private, completely obfuscated from your colleagues, but still allowing you to share that, you need a Slack sync, but the real core of it, that coordination gets better as more people join.
And so that tends to push it throughout the organization. Now, when you hit the walls of the organization, you're right, Ivan, there's not a natural product way for Clockwise to spread right now. And so, the way it spreads between companies is one really fun one is, if somebody changes jobs, they tend to bring Clockwise with them. Word of mouth on Twitter, we have a lot of user love. We also are present on a lot of channels, like on Product Hunt and so areas that people are shopping for software, and just kind of word of mouth throughout the ecosystem of friends, talking to friends about solutions.
That is where marketing needs to play a little bit more of a role for us, is getting out the word about Clockwise so that we can make those hops from company to company. And on the product development side, you’re absolutely right, speaking of things that pain my heart, the number of users that come to our homepage really want to use Clockwise, they’re excited about the premise and can't because they're on Office 365 or they're using Outlook, we will correct that. For those users out there on Microsoft platforms stay tuned, we'll have something very exciting for you within the next year.
IVAN: That's awesome. I'm glad to hear it. I have so many other questions, we have run out of time. Will you come back so we can talk some more?
MATT: I’d love to. This was really, really fun. I’m always excited to talk about technology, software, Clockwise, but especially when those things intersect with Minnesota. That is just wonderful.
IVAN: [laughing] That's awesome. I'm glad to be talking about it as well with you. It's been so awesome spending time with you, talking about your history, how you started Clockwise, all the things that you've done before that and I hope to talk to you again soon. It's been a great pleasure talking to you.
MATT: Great. It’s so fun to be here and thank you for the time and thank you for the platform.
Until next time, this is Ivan Stegic. Thanks for listening.
This is Episode 119 of The TEN7 Podcast. It was recorded on May 14, 2021 and first published on May 26, 2021. Podcast length is 55 minutes. Transcription by Roxanne Chumacas. Summary, highlights and editing by Brian Lucas. Music by Lexfunk. Produced by Jonathan Freed.
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