S10E7: Enabling Scheduling Mastery for Every Professional with Matt Martin, Co-Founder of Clockwise

The lesson that people would try to teach me, and I don't think I really valued it until a little bit later in life, is it really is about the friends you make along the way. That's true in the companies I've been a part of. The most value that I've got out of a lot of those experiences, I've met the right person at the right time. If you just kind of embrace the moment to some degree and the people that are around you, it usually pays dividends.

Welcome back to Season 10 of The Room Podcast. Claudia, can you believe it's been 10 seasons?

Madison McIlwain truly cannot believe it will be 4 years of The Room with you this year. I'm thrilled to be back behind the mic with you for season 10. For all of our listeners since season 1, you truly have been with us for some formative years.

If you're new here, Claudia and I started The Room podcast with the mission of opening the door to the room where it happens, in turn sharing the stories from some of the world's most iconic founders and funders. All in an effort to inspire and educate the next generation of entrepreneurs. And thanks to you all, we were recently listed on the Forbes 30 Under 30 Media list for 2024.

So why us? We're two best friends who met as product managers in 2018, then realized as we were making career transitions into myself, founder, and Madison, funder, wanted to talk to the entrepreneurs that had built great companies. Since starting the podcast, I founded Pryve, a commerce payment startup. Raised venture capital and have faced a ton of challenges. Madison became a partner at Defy VC, was the first investor in my startup, and is now at Harvard Business School and is a pair VC scout coming to the table with the fresh funder perspective.

Over the course of 9 seasons, we've had over 88 guests amassing over $50 billion in enterprise value, ranging from conversations with the former founder and CEO of Zillow, Spencer Raskoff, to Michelle Zatlin, the founder of Cloudflare, Grammy Award-winning artist Sierra, and the creator of Next.js and CEO of Vercel, Guillermo Rauch.

Looking forward, as we continue to expand both online and offline, we are excited to announce the Room Podcast Summit in summer of 2024. The best way to stay in the loop is to subscribe to both the podcast and our newsletter, which you can find at theroompodcast.com.

Before we dive into today's story, we have a few short messages from our sponsors.

Silicon Valley Bank, now a division of First Citizens, remains fully committed to serving founders, executives, and investors across the innovation ecosystem. As the largest banking team focused on technology, life sciences and healthcare, private equity, and venture capital, SVB is uniquely positioned to deliver specialized lending and financial solutions clients need to reach their ambitious goals. Find out more at svb.com.

Perkins Coie is a leading full-service international law firm known for providing high-value strategic solutions for startups and investors. Lawyers in Perkins Coie's emerging companies and venture capital practice support the most innovative entrepreneurs and investors in fast-moving and high-growth sectors across the country while addressing the myriad of legal needs that arise when fundraising and scaling their business. The firm's tailored legal services are informed by an understanding of each client's discrete needs. To learn more about Perkins Coie, visit PerkinsCoie.com. Welcome back to The Room Podcast. Today, we're thrilled to have Matt Martin, the CEO and co-founder of Clockwise. Matt joins us to share his journey and insights on optimizing team productivity through smart calendar management. Clockwise is not just a tool. It's a transformative platform that leverages artificial intelligence to help streamline the scheduling process and free up time for focused work, all while fostering a more productive work environment. Fun fact, Claudia used this product in her early days as a product manager at Uber. Matt opens with sharing some personal anecdotes from his undergrad at Dartmouth, early career in tech, his stint in politics, and how a deep-rooted love for technology turned a personal dissatisfaction with existing calendar systems into a better way to schedule. For anyone interested in technology's role in enhancing productivity, or those just curious about AI's growing impact on traditional business tools, this episode offers a wealth of knowledge and practical advice. Insights and themes include the importance of mentorship for fueling your personal growth, knowing when to go from free to paid in a viral product, and changing how we perceive and manage our most valuable resource: time. Let's open the door.

Matt, thank you so much for joining us in the room today. We're thrilled to have you.

Thank you so much. I'm thrilled to be here.

We always love to start at the beginning with our guests. So before we dive into the founding story of Clockwise and all of the incredible stuff that you've been up to, let's rewind a little bit. Tell us, where did you grow up and how did that shape your view of the world?

Start from the very beginning. I grew up in the Twin Cities in Minnesota, western suburbs of Minneapolis. It's funny that you ask because I think Minnesota actually did have a pretty big mark on me as an individual, and not just because of who I grew up with and my friends and my parents, my family, but the place itself. Minnesota at least when I was growing up, this has eroded a bit, but we have pretty strong— this is a stereotype, but it's also true— a pretty strong Scandinavian presence. There's a lot of immigrants that came more from Scandinavia, ended up in Minnesota for some reason, or the Upper Midwest. And it informed a lot, kind of like the communal values and to some degree the politics, just a strong sense of like communalism and that we can all help each other out. Early in my career, I got involved in campaigns and politics. And so there's a very direct path, but also in my ethos and how I approach the world. I think that's still there.

That's incredible. From early childhood to where you are now, oftentimes the story falls into place, hindsight 20/20. But when you were younger, did you always think you were going to become a founder?

It went in waves. I was a huge Apple nerd and this was dating myself a little bit. This was mid-'90s. I'm outing myself as like a huge nerd. For 8th grade, we had to do a speech to the whole middle school. It was like a, like an end cap on your middle school. You had to pick the topic. Most people who are sane and rational picked a topic that was like, I love dodgeball, or like, this baseball player is really cool, or like, this music is awesome. I picked the history of Apple computers, and this was before Steve Jobs had even returned, and so it was really in the dark days of Apple. I've always loved computers and I've always loved technology. And so there's a part of me that's gravitated to that. Did I in that moment think that I wanted to like start a company or lead a company? No. I don't think I had a concept of what that was until much later, but that love of tech has always been there.

Yeah, definitely. If you're obsessed with Apple, you have to have some entrepreneurial bent and innovation-first mindset. I'm loving this community-first value set that you felt like you had growing up in Minnesota. You went on to Dartmouth for undergrad. Go Big Green, which is a huge community-first experience, not too akin to a cult, some have said. I don't know. And there you studied government and went on to UPenn for law school. So tell us a little bit about that plan going in and out of those institutions, coming out from your upbringing, what that early career path looks like for you.

Yeah, there's a component of this that's not that interesting, which is I went to a good school. I mean, a good high school. I was driven. And so there's a tier of institution that I gravitated towards, and whether that's right or wrong, I think we could have a really interesting conversation about. I think in a lot of ways it is wrong, but like it's a standard high-achieving Type A personality stuff. And so going to Dartmouth, there was an element— it's funny that you point that out, Madison McIlwain— like it was an element of the community vibe of it. It wasn't as cutthroat, and it felt like there was a sense of place and belonging there. Unlike some of the other schools that I joined. And so that was compelling for me. And then undergrad, I was always a computer nerd. And so like I thought about doing computer science, but that the political side was really my passion at that time. I had interned for my then state senator in DC and continued on with a degree in government, which is not worth much in practical application, at least. And I came out the other side, worked on a few campaigns, worked on Amy Klobuchar's first Senate campaign, Al Franken's campaign, a few others, got to know the political community in Minnesota pretty well. And that pushed me towards law school.

I'll just plug the Dartmouth entrepreneurial ecosystem for a second to say that I do think that has carried over into post-undergrad where I've backed Dartmouth founders and I do feel like the venture partners on my side are more collaborative, more willing to not be as cutthroat, to use your word. And it's interesting to see how some of those early ties actually can translate even to like a deeper sense of community post a campus experience.

The lesson that, at least when I was growing up, that people would try to teach me, and I don't think I really valued it until a little bit later in life, is— this is the corniest way to put it— it really is about the friends you make along the way. You learn all this stuff, and that's true at Dartmouth, but by the way, that's true in the companies I've been a part of. The most value that I've got out of a lot of those experiences, I've met the right person at the right time. That was able, unbeknownst to me at that moment, to then plug me in later in a way that was really beneficial. And if you just embrace the moment to some degree and the people that are around you, it usually pays dividends.

I think we finally found the pull quote for this episode that we will market.

There is a joke, and you could use this in the podcast, but we had this little session that was labeled, "What is Clockwise?" And it was meant to be like, uh, we're 7 years into this, and so I think we have a good grasp on what Clockwise is, but we're kind of reevaluating a bunch of things. We want to go back to basics. And somebody was giving a summary of like, what is Clockwise? And one of our employees who I love dearly, and it always cracks me up, instantly put into the Zoom chat, he's like, it turns out Clockwise is the friends we made along the way the whole time. And so that, that phrasing is just in my head right now.

That's incredible. Let's like zoom in a little bit to your journey post-law school. Pre-Clockwise. When you were at law school, you really did start dabbling in tech. Your love of Apple transcended those many hard years of professional studies. You founded a company that helps manage online apartment listings. Tell us about this first entrepreneurial endeavor and how that influenced ultimately Clockwise.

I wish that I could tell the audience that there's some deep lesson here, like follow your interests. I think there's some truth to that actually, but it's really just a series of accidents that in retrospect I can stitch together into a story, but I think it would do a disservice to anybody who's listening to think that there was much logic behind any of this. What actually happened predates that inbode experiment. So when I interned for that senator, I was leaving. Dartmouth has this weird system where you can take off a term, an off-term. And so I was in DC during the winter. Nobody interns in the winter. It's a weird thing to do. And I got to know the staff pretty well and I was leaving and I was like, this has been an amazing experience. How can I stay connected? Like I'm in Hanover, New Hampshire. Like what should I do? He's like, you should start a blog. This is the chief of staff of my senator out of left field. I was like, okay. And so I started a website because I knew how to do websites and that blog ended up being quite popular. It was fun in a lot of ways. Got me connected, got me on the front page of the New York Times at one point, which is still probably the most impressive thing that I've ever done. And that was a complete accident. But tinkering with that and running that website, that was the seed really. Because like I started to figure out how to build websites. I started to figure out, oh, they're like— I grew up around a community where the only people that I knew that worked in tech were the IT people that worked inside of my parents' organizations or at my school. And so I didn't understand what it was to build. I read about it. I read about Apple. I read about this other stuff, but it seemed like a universal way and seemed like I could like build something and put on the web. It was really eye-opening. And so that InBoat experiment, which was a totally failed experiment, by the way, this is the apartment listing company, was just a progression of scratch that itch. It was like, oh, I can make this website that covers political news and all of a sudden thousands of people are reading it. I really hate looking for apartments. Maybe I can do something there. Turns out the answer to that one was no, I can't. But again, it seeded that and part of the journey. And then when I left law and moved to the Bay Area, I had just enough, like just the bare bones minimum enough of understanding an industry in apartment listings to be able to convince another company to let me join. And it's just like those weird coincidences, cuz I had no skillset at that point. Any company that was hiring me was like, who's this weird ex-lawyer from Minnesota that wants to be part of a startup?

I think it's so apt for you to call out looking backwards, you can craft the story, but in many ways it is just a series of accidents that take you from point A to point B. And I think that's in many ways super encouraging for our listeners who are trying to craft their careers and often get stressed that they're doing something that might not be their eventual ultimate goal, but all of that really builds towards what your career arc and what your human experience is. And so, I'd love to just fast forward a little bit. Tell us a little bit more about the aha moment that ultimately manifested itself into you saying, I'm going to quit software engineering at other companies and start my own business solving this specific problem that I see in the world.

One of the threads that is definitely there that's not invented is I have always had a problem with authority. I was the kid who was at camp, who was annoying to their camp counselors because I would never do what anybody asked me to do. And they're probably like, just listen. And so I mentioned that because like there's a part of me that always wanted to do my own thing. I loved working at RelateIQ, which was the company that I was at before Clockwise that was acquired by Salesforce. It was a great acquisition. I got a lot of opportunity there. I owe a lot to that company in terms of the connections I made. There's part of me that always knew that like I wanted to start something. I wanted to start another company. I'd done it before to little success. I wanted to do it again. And so there's an aha moment, Claudia, in terms of Clockwise is the idea, which I'll press on, but I just want to cop to the fact that like it was no surprise, I think, to anybody around me or to myself that I wanted to jump ship and start my own thing at some point.

You're talking about this challenge to authority and the aha moment of really wanting to start something. The product today for Clockwise, as I understand it, is that you optimize team schedules to create more time in everyone's day. That's a pain point I think all of us have experienced in some true form. If you've worked in corporate America, maybe since the dawn of time, how, how did that pain point just keep you up at night?

Yeah, if you go to like an office party and it's at any organization in the United States that has more than 50 people and you start to complain about your calendar, you're going to find an audience. It is a shared pain point. So there's that starting point, which is you spot a pain point that's so common and it's like, why is it still— why is it there? What is so deep about this that it persists? I was living this experience. We got acquired by Salesforce. We're in a huge company and there's a lot of intersections. It's a great company, but it has the same problem that a lot of others do, which is there is what seems like a rush on everybody's time and there's nothing to gate it. Like you just like are inundated. And that was true even of the software engineers that I was managing. We had the luxury of hiring some people who were really motivated, wanted to do great work, wanted to come in, wanted to go heads down and deliver. And yet, they would come to me and be like, I don't have time in the day to do my job. That's not the point where I decided that I wanted to go after this, but that's the point where it started to keep me up. I just couldn't stop thinking about like, we pay a lot. For the time and energy of these employees. Why are we not solving this problem? What is so deep about it that it continues and that it's the butt of every joke?

And so what was that MVP product like when you said, okay, I, I can't go to sleep anymore, I have to start this company? What was the first instantiation of that problem and product?

Yeah, the breakthrough moment where I realized that I really want to start a company around this, I really want to do this. I had a couple other people that I was working with at RelaticQ and then Salesforce, and we're just jamming on this idea. And one of the insights was that RelaticQ was a product that was ingesting a lot of information on emails in order to power a more intelligent CRM and great product. People loved it. I was ultimately sucked up into Salesforce and discontinued, but one of the realizations like it's not novel anymore, but I think at the time it was. There's a lot of data exhaust out of these corporate systems that can be used to power a really intelligent— and because it's intelligent, a really wonderful user experience. You can take that email information and you can power a CRM to do a lot of autocomplete so you don't have to manually enter information. You can surface insights. It's not that far of a leap to look at calendar. There's a lot of data in the calendar, like a lot of data, a lot of rich information. Is there a solve there? And I think that the match of this deep pain with thinking through the data and what could it be used to power in Calendar led to the realization that I still feel today, which is that the problem with calendars and modern organizations is that it's become a tragedy of the commons. You have this really valuable resource, which is everybody's time, but there's individual ownership. Not shared ownership, because everybody's sitting there thinking like, this is my calendar, my time. And so there's a lot of personal effort around protecting it. But the problem is that everybody's grabbing each other's time. It's become networked because we can all look at each other's calendar and just grab it. And through transforming it over the years from a personal resource to a shared resource, you've created this environment where you have a shared resource and you have nobody that's regulating or managing it. So that's where it's like, oh shit, there's an insight here that this has become a network problem. And what are computers really good at? They're good at solving network problems, especially where you have a plethora of data. So it's like, I don't know what the sequence of events that led us to that insight was, but that was the initial aha moment. We have this problem that feels intractable. We think we have a unique angle at understanding why it feels intractable, and we think we have a unique angle of solving it, which finally gets back to the answer to your question, which is the initial MVP was connecting to a friend's calendar at a company and just running an algorithm on it, seeing if we could crawl that data and then algorithmically move meetings just with the calendar data and no user input to see if we could make more efficient schedules. And that was it. It was like a visualization of being able to take the data in and spit a better schedule out. And that was the original proof of concept, I guess not an MVP yet, but a proof of concept.

My brain is spinning cuz I just love this applicability of insight around a fundamental shift in how we work and what the perception versus reality use of the calendar is and has evolved into being. And 2016 was 8 years ago now, thinking about how that's only just accelerated exponentially through COVID and through other products like Calendly, which allow you to externalize your calendar in a really unique way. And like the scheduling nature has just only compounded on itself. The pain point I'm sure you've seen has only just gotten more acute, which has allowed you to leverage your go-to-market strategy once you had that initial product. And assuming you validated it and got it to market in a reasonable amount of time, you're at tens of thousands of organizations leveraging Clockwise today with Uber and Netflix and Twitter. These are hallmark names. How did you go from this MVP product, pain point we all are aware of, to selling into these large tech companies?

People often come really motivated to start a company, really motivated to pursue an idea, and there are a couple of sticking points that they have. One is coming up with that initial idea, which I don't have a magic solve for. Some people have an equation, but for me it was a little bit of like lightning in a bottle. We had this idea, we gotta go do it. But the other one that I think you really can evaluate is what's the market that you're ultimately going to sell into and what does that look like? For us, that was formed not concretely. I don't want to overstate our certainty, but we had pretty strong intuition about the market that we'd be selling into from day one because we'd observed in the calendar market this dynamic of individual time was what most people pursued and it led to failure. Everybody talked about Sunrise Calendar being so great. There are tons of attempts to solve calendaring or solve time management. And if you focus on an individual consumer product, they either are a lifestyle business, which is fantastic. Some people use that pejoratively, but like truly, if you start with like, I want to bootstrap this thing and keep it to 5 people and throw off a profit, like that could be awesome and really lucrative, but there's no scale to it. Or they're, they fail because nobody pays for it. And so we from day one knew that like the angle had to be inside of enterprises. We had to find a way to accrue the benefit to the enterprise itself. And so we never actually, and to this day, it's actually a problem now. We don't allow you to sign up with a Gmail credential. It has to be a Google Workspace credential. And so, you know, you have to try to sign up with matt@gmail.com. I wish I had that email. If you sign up with that, we'll just say sorry. And so we always sold in a business environment. That helped a little bit with that process because we're always looking at how do we spread inside of enterprise organizations? How do we spread inside of established organizations so that we can gain some sense of scale? That's only the starting point. The process of trying to figure out how to monetize this, how to sell it, like that was a long journey.

I remember using Clockwise back in 2018, 2019 when I worked at Uber as a product manager. My schedule was always chaotic and so were the schedules of pretty much every stakeholder I worked with. And I really found Clockwise by having other PMs evangelize the product internally, which was super interesting because it seemed like Uber had access to Clockwise and it spread from there by by just virtue of you encountering it through other people that you worked with using it. Selling into enterprises is something that I think every startup founder struggles with out of the gate, especially oftentimes having a technical founder, first-time founder, et cetera. I would love for you to break down the go-to-market strategy of how did you drive the sale into an Uber, and then how did you drive adoption of your product?

Those are very separate, the sale and the adoption. And I'll tell you why I think it worked for us. So don't look at gift horse's mouth, but I think we monetized too late. It led to a lot of contortions inside of the business. It led to a lot of weird pockets where we had over-optimized or under-optimized. So we launched this thing publicly in 2019 and we didn't charge anybody except for like small little one-offs until 2021. So it was 2 years in market before we were charging anyone. That's why I say at Uber specifically, but for a lot of the early companies, we grew free for a long while. So the motion inside of a place like Uber was that we started to turn on paywalls and we, you know, at Uber we did it very gradually and like try to find the right people. So like we don't want to burn any bridges or turn off what we knew would be a huge account. But fundamentally what we were doing was just saying, your usage threshold is so high, you're far beyond and into this bucket of enterprise purchase. And that pushed internally for some evangelism and some identification with the key stakeholders who could actually make that happen. But it was a weird journey inside of Uber where, and this is, I think, a struggle for a lot of early founders of finding who the buyer is. Who is that person internally that can write the check? And that is just so different for productivity software than it is for a vertical line of business. We don't sell into sales. So you end up with this weird pattern where you have to identify your advocates and the champions who will bring a deal internally, who will say, I want this, and I will go through the internal rigmarole to advocate for it. And ultimately the person who's going to be responsible for provisioning and procurement of it, which is Often with productivity software, some sort of centralized IT.

Total aside, rigmarole is one of my favorite words to use. So love to hear another person using it out in the wild. But in all seriousness, I think that's a really important distinction. And I just want to double-click on the callout around monetization timing and just say thanks for sharing that because it is a really slippery thing, especially when your tool is getting such traction on that B2C motion. When do you turn it B2B and appreciate you elevating that story for you guys.

Yeah, there's a little bit— one of the tricky things about venture-backed startups is like you're ultimately trying to create a company of massive scale that's going to create a return for everybody involved. But the sequence to get there requires additional funding unless you're cash flow positive for some reason early on. And if you are, the question is going to be, why aren't you throwing more of that into the growth and investment of the business? So you do have to for better or worse, as a founder, if you are taking a venture-backed path, you also have to think about what are the milestones along the way that are going to validate and support additional funding. Because part of your job as the CEO, co-founder is to make sure that you can keep the lights on. And if you're not profitable or at least cashflow positive, like the only way you're going to do that is with outside investment. I think we, the point of me going there is that I do think that we monetize too late. However, we had a very keen eye on what do we need to validate in order to keep this thing going? And in the early days, that was the expansion and growth of the product. We knew that the only way that this works is if we can grow exactly how Claudia stated, which is like word of mouth inside of an organization, people using it, seeing other people's calendars. And so by validating those early on, we were able to sustain the business through outside capital and funding. And we made the choice through those early rounds that like, we're gonna put all of our energy over there and not into monetization for now, or to hold off. In retrospect, it worked, but I, I do think it led to some real problems inside the business. Yeah.

And the implication behind that insight for you, for future founders, is know the trade-offs of taking venture capital when you take it and how that might impact your go-to-market strategy and ultimately profitability strategy. So speaking on your own fundraising journey, congratulations, you've raised over $76 million from venture capitalists who are top-tier names— Bain, Cap Ventures, Accel, Greylock— and that was totally a choice. And it really does take a partner to say yes to some crazy kids from RelateIQ and a big idea. So curious, who was that first person to say yes to investing in you and Clockwise?

Yeah, I would love to give you a story that's like, we were just so brilliant and obviously so charming and amazing entrepreneurs, technically just out of this league. But the reality is, again, going back to where we started, relationships. We got lucky. The founder CEO of RelateIQ left days after we decided to leave because he was obviously so heartbroken that his all-stars had left. He was like, I'm out, and became a partner at Accel. And he was our first investor. Steve's a really bright guy and has made some incredible investments. He wasn't going to You know, it is relationship-based, but he wasn't going to invest in anything. He was really excited by the idea, but that relationship, obviously foundational. Like we had that door open to us and we could have that conversation.

We talked about a lot of different moments in the founder journey for you, a lot of the tactical side too, maybe more at the high level. In your own founder journey, there's often high highs and some low lows. It's been 8 years for you with Clockwise. Maybe tell us about a time that just didn't go as planned.

Oh my God, how long do you guys have? Joking aside, uh, it rarely goes as planned. I look back and the contours of what we built and like the direction we've gone generally aligns with where we started, but the way you get there, it's just this weird curvy path of like insights and failures. And I'll share with you both publicly on a podcast that'll go out to people, something that I haven't shared with many people, which may or may not be wise. We were in like our first year of going after this. We'd taken the money from Accel, and so we knew we were on the path, right? We knew we were on the VC path. We knew that we had to hit a milestone in front of us and just like nothing was working. And I don't mean like we were getting some adoption inside this company, but like the curve wasn't right. I mean like nothing was working. We couldn't get traction anywhere. We couldn't get it out the door. We didn't know what form it should take. We had tried a bunch of different experiments with a website version. None of it was taking. And I remember walking down Townsend Street in San Francisco. I'd gotten off my bike because I was calling up Steve to be like, we just had to shut this thing down. Like, this is just a waste of all of our time. This is just like, I can't make this work. This will never work. It's too crazy. People don't want their meetings managed by a piece of software. Like, it's not going to work. And Steve, to his credit, was like, hey, you want to shut it down? Like, we'll shut it down. But I got to tell you, I think you need to take a beat. Think about it and like look at the vision because your vision is right. This is the right play. And the lesson that I have from that for other founders that might be listening or aspiring founders or people who are in the journey is the managing of your own personal psychology is actually a really critical part of this overall journey. It turns out that I was wrong in that moment, but I could have been right. But the point is that I was coming from a really emotional place. You invest everything in yourself in this damn thing. And like when everybody's beating you down, it's easy to go to a place of negative self-worth. I'm failing. This is bad for me. I'm doing a bad job. Like, I'm not thinking about this right. It's an emotional spot, and you'll end up making poor decisions because you're going to a place that's not rational. And the other part of that's just as important, if not more so, is you will burn yourself the fuck out fast. You will not have the juice to sustain. And so figuring out how to manage your psychology. And like, that has been a journey for me. Like, figuring out how to manage those ups and downs, I think, is probably the most important thing that you can do if you really want to make a go of it over the long term.

That resonates so deeply with me. Madison has seen me over the past 3 years through some serious peaks and troughs, and I think there's this really unhealthy perspective for folks that are just starting that you need to work the hardest by virtue of hours and depriving yourself of anything that brings you joy. Otherwise you're not trying hard enough. You have to have inspiration, you have to have energy in order to think clearly. You have to enjoy life, otherwise the thought of continuing is depressing, which is ultimately not good for the business and the team. So it's a really apt thing to call out as just struggle that every founder deals with.

And if I can just also say, like, I've been so honored on the investor side. I'm a proud investor in Claudia. When she does trust me with these more vulnerable moments. And I think there's a bit of a dynamic sometimes with investors where you are afraid as a founder to say what you're feeling because there's this long time horizon and there's these expectations. Thank you for sharing that you felt comfortable with Steve to have that moment of vulnerability and he could see you through it.

Yeah, I had to go back a beat on that. I think having the right investors, sometimes you don't have a choice. Yeah. That's brutal. You gotta swallow it and you keep moving forward. But I implore everybody to think really deeply about who they're partnering with. It definitely reveals itself in that Steve moment, but it also reveals itself even in that journey to monetization. If we hadn't had buy-in and alignment with our investors of what the journey and vision for Clockwise is, it gets very easy and rational, by the way, for like those investors to be like, charge, charge, charge, charge, charge. That may have been the right advice, but like the point being is that if you enter that relationship with mismatched expectations, even if you get the capital in, You're going to drive yourself up a wall while burning the cash that you just got in the wrong direction. And so having that alignment, having that clarity of like, who is the person that you're sitting across the table from is really important. And then last note on that, Madison, like it's amazing that you have that relationship with Claudia. I value deeply my relationship with Steve. You don't need that at every investor either. That's not like to other founders that are out there, like you're not necessarily, if you can get that, it's fantastic. That sort of like transparency. And authenticity is so valuable in relationships, and I'm fortunate to have that with several of our investors. And so you can find it and it's great. But also like what you really wanna know is this person a true partner? Are they there because they believe in your vision and where you're going? And do you have alignment? Or are they just there because they think there's a pot of gold at the end of the tunnel if they can make and push the company in the right direction?

Man, I wish there was a magic wand that told you which kind of investor you were speaking to, both on the investor side and on the founder side. I'm sure even more.

Thank you, Matt, for just all of that wisdom. It's incredible to just like hear these reflections after quite a few years into the journey. Let's switch gears a little bit and talk a bit about the future and where Clockwise is going. On the product side, GenAI, it's been a huge piece of Clockwise's recent product innovation. Tell us a little bit more about the history of leveraging natural language models in managing calendars. And why the time is now for a true AI calendar innovation?

Oh, great. This is an excellent question. It's fantastic. It's interesting. So when we started Clockwise, there were a couple companies that people might recall. Some of them are around, some of them aren't. One of them was Clara. Another is x.ai. x.ai is still around. And they had similar visions, which was, we are going to use ML. We just rebrand AI every few years. We're gonna use ML and NLP to create basically a digital executive assistant. You could CC them and they would try to respond to stuff. And they didn't work. They didn't work well. They didn't work nearly well enough. And I think that vision is not necessarily wrong, but we saw it and we took a hard line. I think this is some of our early decks. We're like, we are going to augment and assist. We're not going to automate or replace. We believe so strongly that the tech wasn't there fundamentally. That personifying the technology and trying to make it into assistant was not just folly, but inevitable failure. And now I think very differently. I think the thing that's different about Gen AI is that for the first time ever, we have something that doesn't just process language, but actually you can call it reasoning. Maybe that's too anthropomorphizing. Who knows what it's doing under the hood other than probabilities, but like does a good job of sussing out and interpreting human intent. What does the human want out of this? What is the human trying to say? And very good at that with human language because of the way that they're created. We've been monitoring this since day one. We used ML to categorize some of the early stuff. It's important for the underpinnings of Clockwise work, but we never quite saw the breakthrough moment until GPT-4. And there was a very big upgrade from 3.5 to 4 that probably not everybody felt, but if you work in calendars, you sure did, which is that it became for the first time it could reason about what a user requesting in a temporal sense. And they— OpenAI actually put this on their website, like they had an example with calendar. And so we saw that and we started to play with it and run with it. And it's been a wild journey since. We initially hoped that we could take our scheduling engine, which I think is fair to say I'm biased, but I think is the best in the world. Nobody else has ever tried to automate events using calendar data. And we do that and we understand events, I think, at a deeper level than anybody else. And we have an engine that parses them and moves them real time. I think we're very good at that. And marrying that with a chat-based experience that you could talk, we thought like, this is gonna be amazing. We're about 8 months into that and we've learned a lot on the way. And I think one of the mistakes that a lot of companies continue to make is that it's rare that the use case for GenAI is so transparently good and matched to the chat format that you can just take chat and create the workflow. You need to apply GenAI to a native workflow. And that's why the best copilot out there, in my humble opinion, but I think shared, is GitHub Copilot, because it's native to the environment you work. You work in the text, you work in the code, and it's right there alongside you. Now, trying to get data analysis out of a chatbot A little bit different, but still works. Often you might make that request to somebody else and like you're trying to query, like there's a query essence to it, but trying to just state to Calendar what you want, users need to see and validate and trust that system and they need the calendar side by side where they need to have a visualization. And so our journey has been one where we see the power of this thing, we see where the world is headed, we see that clearly, like it's so obvious to me that Everybody inside of every organization is going to have a personalized assistant that understands what you need and going to help you get the best schedule that you want. And we think that needs to be built native to the interface that people are familiar with, which is a calendar. And I think you'll be pretty pumped to see what we come out with this year.

We're excited. Related to what you just mentioned, I'm sure you've seen a lot of shifts in how people use their calendars over the past 8 years. Tell us a little bit more about some of the behavioral changes you've noticed on a macro level, and how has that influenced your product roadmap moving forward?

So the wildest thing that happened was this impromptu global experiment we ran called COVID, um, and everybody all at once was like, we don't have a choice, we're all working from home now, we're going to all be remote. And I personally even got dragged kicking and screaming to this. We're now a remote company, and before we didn't even have the optionality for a flexible day. Maybe I'm a bad boss, but we all had to learn how to operate remotely, and you could see it in the calendar data. The number of meetings that people had shot through the roof. You also saw it in the behavioral reporting where people were getting burnt out because it's not just sitting back to back, but you're sitting back to back looking at this damn screen, looking at yourself all day, and it's a different mode of interaction. It's a different mentality that you bring to it. And so I think that one of the things behaviorally that we really emphasized over the last couple years is like we started to build in ways for people to make sure that they're getting breaks in between the meetings, making sure that they're setting boundaries, making sure that they're signaling and communicating through their calendar what they need and what they don't need so that when people try to schedule those meetings, they're there. Making sure that managers and organizations are empowered with the data that they need to understand to know that, okay, we have a problem here. But I do think that the next evolution with GenAI that it opens up is helping people to work in distributed environments and remote environments in a way that's much more beneficial to everyone. Because again, going back to the original thesis, this is a shared problem. You're not going to individually muscle your way out of a bad schedule. You've got to have something that's looking out for what's happening across your team, what's happening across the organization. And if you have a, like, a little buddy in your Slack or next to your calendar that knows everything about you and your organization's time. Turns out that's really a great way to help make those schedules better.

Pretty helpful. And honestly, thinking too about like the way we work today, being distributed allows for so much more flexibility on also what else you do outside of your core job. And honestly, Claudia and I doing this on the side from our careers, it's become a complement to our careers. This scheduling headache is super real because we have a separate calendar and her and I aren't in the same actual organization and We jankily use a Calendly thing. We could be doing that so much better. A, I think you have two new Clockwise customers on this call, but B, I think you're hitting on some of these fundamental shifts in how we work and play that Clockwise is so uniquely positioned to solve.

Thank you. I of course agree with that. Um, but I think that one of the things that you asked about earlier that has really hit home is how the demands on our schedules have actually gotten more complex. Rapidly, and remote is a big wrench in that. And we're, we have not figured it out. I think we've gotten better at it culturally, collectively over the last couple years that people have grappled with it. But just at a basic level, like trying to schedule across time zones is tough. It sucks. And you schedule across like 3 different people in 3 different time zones and it's just, it's logistically challenging.

It truly is. Thank you so much for sharing about Clockwise, where you've been, where you're going. In our last 2 questions, We'd love to start by touching on what's next for you personally.

Ah, what's next for me? I have a kid coming, a third kid. We have twin girls that are toddlers and number 3 is coming in May. Personally, that is like the start, middle, and end of that sentence on what's next. It's about to turn my life upside down, but we're excited.

Awesome. Congratulations and look forward to hearing more about that exciting journey of bringing a third on. I'm a one of three, so definitely know it changes the dynamic, but in great ways. Okay, final question, our hero question we ask all of our guests. Who is a woman in your life that has had a profound impact on you and your career?

Oh my God, I'd be a liar if I didn't say my mom. This not in a sappy way, but very deeply and genuinely, like she was a role model for me in a million ways. But I think one of them was that she was always a working mom. She was always juggling being present for me as her kid, but also just being frankly a badass. Like she's a leader in the industry. I aspire a lot to what she did, and I think she opened up a lot of lanes for me in terms of understanding how to strike that balance, how to do it properly, and also how to stay sane through it. Mostly sane.

Mostly sane. Moms are good at that. Matt, thank you so much for coming on today to tell us your unique story, Clockwise, and the future of calendling everywhere. We are looking forward to living in that future with you, and thank you so much.

Thank you. Thanks, guys.

Thanks, Matt.

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