Matt Martin On Raising $76 Million To Help People Manage Their Time

In the vast landscapes of Minnesota, where winters are cold, and summers are serene, Matt Martin found his roots. In a recent interview, he took us through the remarkable journey that led him from the world of politics to the heart of Silicon Valley, sharing insights and pivotal moments that shaped his career.

His venture, Clockwise, has attracted funding from top-tier investors like Accel Partners, John Lilly at Greylock Partners, Ajay Agarwal at Bain Capital Ventures, Lucas Swisher at Coatue, and Steve Loughlin at Accel.

In this episode, you will learn:

• The journey from rebellious beginnings to a successful entrepreneur underscores the importance of resilience in navigating career transitions.
• The years at Sequoia provided invaluable insights into the world of venture capital, shaping an understanding of visionary entrepreneurship.
• Rejecting a lucrative acquisition offer and persevering through market challenges showcased the strategic decision-making and long-term vision for BigPanda.
• Building a resilient organizational culture requires a careful selection of executives aligned with core values and a commitment to the “first team” philosophy.
• BigPanda’s mission to empower teams with AIOps reflects a visionary approach to automation, envisioning a future where human efforts focus on innovation rather than operational firefighting.
• The emphasis on cultural fit and “first team” thinking serves as a lesson for aspiring entrepreneurs in curating effective leadership teams.
• Entrepreneurs should be meticulous in selecting executives, ensuring they not only bring expertise but also align with the company’s values and foster a collaborative leadership mindset.

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About Matt Martin:

Matt Martin is the Co-Founder and CEO of Clockwise, the smart calendar company that’s reimagining the way people work.

Clockwise is an intelligent calendar assistant that frees up your time so you can work on what matters, using artificial intelligence to understand your work and life commitments and automatically organize your calendar to help you focus on your priorities.

Prior to starting Clockwise in 2016 with co-founders Gary Lerhaupt and Mike Grinolds, Martin was an engineer at RelateIQ, a relationship management software firm that was acquired by Salesforce.

Matt earned a BA in government at Dartmouth College and a JD from the University of Pennsylvania Law School.

Connect with Matt Martin:

• Crunchbase
• RocketReach
• LinkedIn
• TheOrg

Read the Full Transcription of the Interview:

Alejandro Cremades: All righty hello everyone and welcome to the deal maker show. So today. We have a really amazing founder that you know we’re going to be definitely talking about the rocket ship that he’s building but there’s a lot you know to really unpack on our on our episode today. You know from. Being a lawyer to all of a sudden becoming a software engineer and now running his own startup being part of an acquisition. You know he was part of the team of this company sold to sell to Salesforce and then also figuring out monetization as well as the emotional roller coasters that you deal with as a founder. So without further ado. Let’s welcome. Our guest today Matt Martin welcome to the show. So originally born in Minnesota give us a walk through memory lane. How was life growing up.

Matt Martin: Thanks for having me all Ajandra I’m happy to be here.

Matt Martin: Ah, you know Minnesota is one of those places where it is a fantastic place to live despite the weather. Um, great, upbring. Great place to grow up. Ah you know, great friends. But also you know there’s not There’s not a lot that I can tell you like you got to come here for this, you got to come here for that and the lakes are great. Um, but it’s mostly just so you know it’s a wonderful place to to grow up um, cold winters lot of sledding nice summers and that’s about it.

Alejandro Cremades: That’s amazing now in your case you know, eventually you know you went to dartmouth for the undergrad. But 1 thing that is very interesting is that you got into the whole politics. How did you get into politics how how did that happen.

Matt Martin: Ah, interesting. Yeah, so you know look I think that one of the things that actually came with me from Minnesota is that we have ah a tradition of kind of pragmatic progressive politics. Um, it’s going to all the scandinavian blood that’s out here. And I just saw the value of when people come together. You can actually do big things. Um I think in a weird way. It’s actually what inspires me to be in software as well is having an impact on a large scale. You know can push a piece of software to the web anybody can access it and in politics it works the scale of changes I think even larger even though. Time to change is much longer and slower. Um, and so I just got really fired up in high school and then in college I ended up interning with my then senator and just kind of got the political bug couldn’t help myself um and ended up ah working on a few senate campaigns. Ah with ah. Now senator Amy Klobuchar worked on her first senate campaign worked on L Frank has campaign. Um, but also you know when you’re a young when you’re a young person. It’s just ah, you know you’re surrounded by really sharp really motivated really high energy young people that are getting paid nothing. Um, that are working hard to kind of pursue a vision. So it’s it’s just a fun environment.

Alejandro Cremades: So then in your case you know, eventually you um, you went from that to law school. You know like what? what? what puts you? what push you into into law school.

Matt Martin: Oh man, that’s a good question if I could tell myself now if I if I could tell myself then what I know now would say you know save the money. Ah, but I think it was the political bug I mean you know look like I was I was working on these campaigns I was in these circles where.

Alejandro Cremades: Um.

Matt Martin: You look at kind of the career path and either you flame out or you end up, you know, kind of going down a policy route and I I was motivated by having that level of change by being involved in those circles by being involved in those big decisions and so law school just looks like a natural next step that you know you you pull your head up and you look around. You’re surrounded by lawyers and you think well. Maybe I’ll be one of those um and my intent going to law school was to come out the other side and do something in government or in ah public policy or in politics. Ah but I was ah graduating from law school kind of during the height of the legal recession which kind of. Trailed the you know the o Eight Zero Nine Ten recession a little bit. Um and just not many places we’re hiring but places that didn’t make money certainly weren’t hiring so governments were kind of on a hiring freeze public policy shops for hiring freeze. But that is what got me in um, but I ended up being a. Litigator in a large law firm which really wasn’t my intent.

Alejandro Cremades: I Mean that’s a quite the transition there now being a litigator. Obviously you were able to you know at least see the bad and the ugly when it comes to the corporate side know so so over some of the things that they.

Matt Martin: Now.

Alejandro Cremades: Perhaps you you learn there. You know about things going south when it comes to business.

Matt Martin: Yeah, you know it’s interesting I mean one of the things about being a litigator that you have to wrap your head around is you are always trying to give your client The absolute best argument you’re trying to you’re trying to position their facts and their circumstances in a way to provide the best advocacy and so I Think. You know you can either kind of go off the deep end and convince yourself that you’re always right? Um, which is which is a strategy that some Attorneys take? Um, but I think what for most Attorneys or litigators realize is that every situation is nuanced. Every situation has sides to it. Every situation has you know sides where you probably are in the right where you’re probably in the wrong. Um, and at realizing that you know this is all business. Um, at least in the context that I was working in I was a litigator not in a criminal sense but in a civil Census who were doing civil litigation for large companies. You realize you know look. It’s business. There’s nuance here. Some people got to write some people got it wrong. It’s rarely black and white but you try to give you try to dig in find the best facts and figure out how to provide the best ah advocacy for a client I think that was a interesting ah education for me as somebody operating in. Commercial Sphere is you know, look like you can look from the outside and you can handicap these things but people are making the best decision they can at the time and every once in a while you encounter a truly bad actor but most of the time It’s just things going off the rails or not going the right direction people not seeing eye to eye.

Alejandro Cremades: Now in your case at what point you know now that you are a corporate attorney and and obviously you know as an attorney you make good money but at what point does the live crisis hit you to start thinking what the hell am I doing you know I may I may have to maybe explore a different path.

Matt Martin: Yeah, well fortunately hit me relatively young. It wasn’t midlife. You know look so being an attorney you’re right it it is it is especially in a large law firm. It is stable. It is a pretty good salary. It is a pretty good lifestyle you work your ass off, especially as a young attorney. Um, but I think if you get into it and you’re on this path that’s kind of something you enjoy you might have a screw loose in that regard. What drove me nuts more than anything else. Actually I did not hate the work There are some attorneys who just like fight in a bore I found some of this stuff pretty interesting and pretty engaging. But what drove me nuts is that stability. You know I could look down the hallway of this law firm and I could see partners who had been there their whole life and I could kind of see where I might be when I’m forty fifty sixty years old and that just ah, frankly, scared me. Um I like. Ah challenge I like volatility I like change I like grappling with new circumstances. Um, ah that that sort of kind of stable tried and true path just was no interest in me. It didn’t seem like a good way to spend my few years on this earth and then in combination with that. You know one side that um on my life that doesn’t come up in my bio is I love making um I was always kind of a you know drawer painter ah and as much as somebody might try to convince you that writing a legal brief is a creative process. It is not it is.

Matt Martin: I Mean at the margin sure but you are not putting something new into the world something that you created and so just that like I don’t know that creative Zeal I Just that combined with kind of the I don’t know the the stale security of it I Just it was driving me bonkers and so I was like I got to get out of here.

Alejandro Cremades: So then tell us about that moment where you make the decision I got to get out of here what happens after.

Matt Martin: Yeah, yeah, so so this is embarrassingly cliched for a Silicon Valley founder but I I will cop to it I was in my office and Steve Jobs died and ah I had always been an Apple guy and like to look like. Um I revere steve jobs but I also know he’s a human he had a lot of downsides and a lot of bad behavior but look that guy changed the world and he was always an icon for me and he he died and I was in my office watching his Stanford commencement address. Um. And in that address. Ah you know he has a line essentially to the extent of like you know, the only way you can do great work is if you’re doing something you really love and ah deep down I think we all know what that is it just we find reasons why we can’t do it and for me, it was just. I had been building a software company on the side. Yeah, it wasn’t going anywhere I mean I I was a full-time attorney I was trying to do this in law school. It was kind of a hobby but I loved it. You know I always loved putting stuff on the web I I always loved creating software I’d always loved actually engineering software engineering be able to put. You know fingers to keyboard and create something new and just remarkable and I was just sitting there and going you know he’s right I got to I make excuses I got to go so I left and came to the bay area and um took a job I don’t have a cs degree.

Matt Martin: I you know I don’t have an Mba um I don’t classically look like anything that a startup needs. Um, and so I just hit everyone that I could to try to find a job at anything I could you know it took a huge huge huge pay cut initially to 0 because I was just trying to find something.

Alejandro Cremades: Ah.

Matt Martin: Um, but you know, kind of weasel my way in a few startups and then prove myself and prove that I could actually you know do a little bit of coding and ah wean that in the next thing and I was you know off to the races.

Alejandro Cremades: So obviously 1 thing led to the next and then you ended up in relay iq which really gave you access to seeing also the full lifecycle of a company. No and really experiencing that because the company ended up getting acquired by salesforce but.

Matt Martin: Am man.

Alejandro Cremades: What what was that journey like of of really being able to experience that and and having that type of visibility to to what the full cycle looks like.

Matt Martin: Yeah, um, so I’m to I’m to get to relate q in a second but aahjandra when I whatever I’m on these podcasts I I always like to pay it forward a little bit um in not papering over that transition. Ah because i. I have been on the other side of that coin where you know I was trying to break through into software and it looks like it should be easy or I hear these stories it just happens for people. It was really hard and so if anybody’s out there who’s trying to make that transition themselves who’s trying to break in. Um, especially if you don’t have a cs degree or if you don’t have a cs degree from ah you know one of the top 10 cs schools. You know it’s it’s hard it is really hard to break through um and I would just advise people that if this is your passion. This is really what you want to? do you got to dig in and prove out. How you can add value. You know, push that um side project. You know, really push yourself to the limit in terms of domain expertise in an area that you’re really excited about prove yourself take that take that job that you know maybe you? Um. Don’t quite have the financial wherewithal to take but take it for a couple of months to try to prove yourself. Um break it any way you can and stay persistent with it and if you ever want to chat about it. You know, hit me up. Um, but let’s move out of related q.

Alejandro Cremades: So So so walk through us, you know, walk us through how you know what’s that experience for you having that level of visibility now of not just startups like you you know had been experiencing but now after especially you know like hitting it on the software side but more On. Being able to see what a really good company has to be able to reach the finish line.

Matt Martin: Yeah, so re relatedtaqueue is kind of like lightning in a bottle. Um, you know huge credit to the founders there. so so Steve Laflin and Adam Evans Ceo and cto those guys had a vision. Um. From day one of what could be possible in terms of enterprise software and it was just you know it just hit the market in a way that people are like yes yes that resonates and and ah and ah, explain to the audience I mean basically. I won’t get the snappy version of the vision I’ll give the I’ll give the raw version internally is that they saw that inside enterprises. There’s all this raw information that is basically kind of like data exhaust off of other systems and there were. Initially exploring some of the different ways that they could go about ah utilizing that but then they came to one which is okay out of email. There’s all this rich information about the relationships inside of an organization. You know who’s emailing whom who’s talking to whom what’s the cadence of that conversation where do things drop off etc and eventually. Um, figured out that okay we could actually map this into a crm in a way that’s pretty potent and I think the additional insight was seeing now this is you know this was founded in 2012? Um, so about a decade ago.

Matt Martin: Um, and things have changed a little bit but also seen the opportunity to provide really best of class design and software inside that enterprise environment and so what they what they had there was a piece of software where you would sign up with your email address. Um, and it’s a serum customer relationship management platform. So you know you might be at a sales environment or Vc Environment you’re looking to track kind of leads and ah, um, and accounts. But it would automatically pull in from your email information about those accounts you didn’t have to fill in the data. The drudgery of kind of like ah you know, filling out all these fields. And then it would track it over time like what’s happening in that you know who’s talking to them if you’re working on a multi-person sales team or in a large organization like you can see who’s the closest connection inside this account and what really stuck with me is a couple things. 1 is. If you provide a piece of software that makes the user feel like they’re running downhill when usually they have to run uphill, it’s magic. You know if you can create that feeling of you know this used to be you know a pain in my ass I used to have to do a lot of work to get this in but man I’m just moving its magic. And then if you marry that with a design and interface that emphasizes that feeling that makes it feel you know approachable easy to use that really amplifies that so there are the product learnings on that side and then culturally and I’ll let you choose Aljandra where you want to die but culturally.

Alejandro Cremades: Um.

Matt Martin: I Think their ability to push that vision into the market and really kind of amplify Beyond the team we were our presence in the market and and the market’s belief that this is the future was really um, inspiring.

Alejandro Cremades: And obviously you know this allowed you to to see how a large corporation like salesforce because I mean you were part of that the transition to air with salesforce but 1 thing that is really interesting. There is now you’re in an amazing organization. Really big. As part of the transaction and and and at what point do you realize? I think I’m ready to really go at it and and bring this new baby to life. You know how? how did that happen.

Matt Martin: Well well a ah hundred I’m going I’m going to hit on that but well let’s touch. Ah, just one second on that salesforce transition. So salesforce came in and they had hitlayq a couple times with ah possible acquisition and 1 of the lessons I think for the folks who are listening if you’re an entrepreneur is. Stephen Adam the founders at relatedqueue given how they had pressed that vision and and made the future so clear salesforce paid a price that was really representative of them buying the future. Um, it was a good acquisition relative to the stage we were in terms of revenue. Um.

Alejandro Cremades: Close to 400000000 correct that was close to four hundred million first

Matt Martin: And won’t reveal any $400000000 acquisition. Yeah, and I won’t I won’t reveal any of Stephen Adams secrets on how much revenue we had at that time. But um, you’ll have to get them on the podcast but it was it was definitely you know Mark Benny off and the salesforce team were buying the future and. I think that ah you know one of the lessons that I take home. There is that you know there’s an aspect of building a startup of building an enterprise of building a company that really is getting out of the market and making making sure that people see what the path is you’re creating because if they believe it they feel it. You know they’re going to pay a premium. On current status because they see that that path is there they see where you’re going. They see that they want to get it before it’s too late. Um, so that that was also another thing that I took home. But then so we we got purchased by salesforce 400000000 at that and that was had then stop prices. That’s really, um, yielded. Ah, ah. Kuris to to Steven Adam I was not a co-founder there. So I wish I had co-founder level ownership. You know we might be taking this podcast from a different location. Um, but I was there after ah, the acquisition I was managing our frontend software engineering team and.

Matt Martin: You know, after an acquisition like that there there are a few different different passs that he can take if you’re somebody like me who is antsy. You know you go back to that kind of ah realization as I was looking down the hallway at the partners at my law firm. Um Salesforce is a dynamic organization. It’s not like law firm. But ah. Yeah, where I’m I’m now kind of in the belly of the beast is’s a large organization. Um, very successful organization. Very inspiring organization I have a lot of respect for it. But I get antsy I Just like you know it just it just it’s not my product. It’s not my company. Um, you know I’m not. Ah. I’m not a pirate anymore you know I’m kind of in the Navy and so I started looking around a little bit antsy about Okay, what’s next?? What’s next but I wasn’t seeing it I Just you know you don’t want to jump too early. Um, you don’t want to jump out of that antsiness you want to you want to jump to something not from something and so but I was keeping my eyes peeled.

Matt Martin: And ah I started having conversations with a lot of my peers. Um folks who had come over from that acquisition who were also feeling a little bit antsy and entrepreneurial and the 1 thing that we kept on knocking around is just as participants. This organization as employees as managers as I see engineers as cross-functional leads as people are interfacing with salesforce corporate. It seemed like none of us had a schedule that supported. What we actually need to do in the week you know I’d hear from my engineers. You know they’d come to me and say hey Matt um I have to work at night I’m not getting what I need done during the day I was seeing the velocity of our shipping you know, just felt like kind of like you know it couldn’t quite get there. Um, and you know we hire brilliant people. It’s one of the true privileges I think of the software industry and especially in Silicon Valley you work with really smart motivated people. They want to get in. They want to code they want to deliver. They want to ship. Um and yet schedules seem to be getting the way and for me as a manager.

Matt Martin: I’m interfacing with you know dozens if not hundreds of different people. My schedule is kind of a nightmare I don’t have time to focus I don’t have time to get ahead I feel like I’m always wrap in and it it kind of comes back to Ajandro that ah learning fromlqueue.

Matt Martin: The magic of taking some of this data exhaust and making it feel like people are running downhill instead of uphill because me and a couple of colleagues specifically Gary Lairhopp who is my cofounder you know he was identifying like we have all this information in the calendar about. Where people need to be what their schedules look like ah where their limitations are who they’re meeting with you can get the network of the organization. You know who are they meeting with how are they meeting? Um, but you can also make it more efficient and that’s when it really started to click with me. Um. I think to get a little philosophical on you time is you know, existentially our most valuable resource. But even in a corporate environment. It is the most expensive resource because payroll is the biggest expense you know good people cost a lot of money. Um, and yet we don’t use it very efficiently and why like that’s the question that kept me up at night like why? Why is this really expensive resource that everybody values used so portly and I think the answer is because in modern organization. It’s become shared nobody controls it. I schedule with you now we have a joint time together. My whole day is set up from schedule is other people requesting my time I go in between meetings and I have slack messages I have emails I have docs to respond to. We are constantly asking each other of time.

Matt Martin: And yet there’s nothing that coordinates or regulates that it creates a classic econ 1 onone tragedy the comments you have this really valuable resource. There’s no regulator, there’s no coordinator so everybody just grabs at it and exhaust it and that was the moment where on the backdrop of having taken. This other company using the data exhaust from corporate systems to provide a better experience and the realization that nobody was solving this at the system level where you actually could coordinate time that was where it’s like oh man we got to do this. We got to jump on this.

Alejandro Cremades: So then you ended up jumping on this. So what happened next.

Matt Martin: all right? all right we jumped on it. So ah, there are all sorts of different founding stories sometimes people come out of this and they have like a fully fledged vision. They’re like I know exactly where we need to go I just need the resource to do it other people jump into it and they’re like I just really want to start a company and i. Kind of have an idea but they end up pivoting a million times we were the flavor where we have this insight and that insight has remained true. Ah time is using efficiently. It’s because it’s shared. It’s because there’s no coordinator. Um, we can make it better and if we can make it better. For individuals we can give organizations huge huge value. It makes them more efficient makes them faster makes them more productive ultimately makes them more competitive on the market. It’s hugely valuable. But what we didn’t know yet is how to bring it to market how to productize that what form it would take. And so while that insight was clear where the vision of where we might go is clear the actual how to put you know into the market was not and so the first thing that we did is we quit and then we started to test out. Um, algorithmically is this even possible. You know if we get access to calendar information. Can we actually improve it. Algorithmically can we look at it analyze it and more efficiently schedule because to to nerd out for a second it it is a classically mp hard problem.

Matt Martin: You know you can’t get to a perfect optimization and will um, exhaust compute it. It is it is is is too tough and so you got to take different strategies so we went out and talked to our network and we found some people who were friendly enough to let us connect to their calendar system and then we would ah. Spend our all day every day in our nights and our weekends trying to test out different strategies of how we might optimize it and then we we knew that people would have to see it. They kind of just see the numbers so we built out a little visualizer to show how it could work I showed it to some of those folks, especially leaders and um. You know the moment I knew we had something is when I saw still remember ah we were in segments offices and we ran this. We showed them the the optimization you could see the events moving. We had. We had kind of like stitched together this little visualizer that kind of looked like a calendar but it was across. Ah, you know thousands of events and you could kind of like see them moving and mass and optimizing and that would ratchet up the efficiency that was gained and you could just see like his eyes widening as he was watching this the leader at segment Andre like you know if we could build this for you would you pay for it. It’s like. Ah, yes yes I would I’d pay you a lot. Um, and so we then leveraged we went on and collected a few of those stories along with the visualization. We leveraged that to get a seed round. Um, so we get a little bit of funding. This is all effectively pre-product I mean we had um.

Matt Martin: You know some of the foundational code that’s still with us today but we had not productized the um but that was the start and we raised a seed round from excel partners in early Twenty seventeen

Alejandro Cremades: And what was the journey of finally you know like getting this thing done and most importantly, figuring out how to monetize it.

Matt Martin: Ah.

Matt Martin: Oof. Okay, so you know I envy those going back at Tick I Envy those who have a clear vision out. They’re going to bring it to market exactly who they’re going to sell to exactly how they’re going to sell it etc because we spent we spent a while trying to figure this out. Um, and you know there were moments that were really fun. But collectively. There’s a lot of darkness there because we had that initial ipo moment where like we know we know we can provide the organization value. We know that we can deliver a huge amount of roi but nobody’s trying to buy this thing. You know this isn’t something that people are going out and searching on Google you’re an engineering leader. How can I optimize calendars. Um, so there’s noneexisting product category that we can just play in. You know there’s no gartner quadrant that we can fit into um and and then additionally to actually have this thing work. Um, you need to get the buy-in of individuals. You know. It’s to maximize the productivity of the organization. The individuals got to be okay with it because it’s their schedule. You know they have to they have to say okay, this is actually better for me. Um, otherwise it’s very easy for that individual to just reject the thing or say you know no way so we had to experiment. A lot. Yeah and it was um, not easy I mean a lot of the times it looked like there’s just no way this thing is going to work because you’d go in our initial attempts were to bring an individual in and give them recommendations.

Matt Martin: And there were good recommendations about how you might improve your schedule but they just weren’t you know they weren’t tactical enough and you know we weren’t we weren’t providing enough value to that individual to come back and so I I remember one winter where I was just like this is never this is never going to work. Maybe we should just close the door. Get back the money and get on with our lives because we just couldn’t crack the nugget but then there was a moment. Um right before a board meeting where we flipped in onboarding and onboarding the product. I won’t go into the the details because it gets a little bit into the particulars of our product but ah essentially we flipped to default instead of but giving the user recommendations having them opt in we took a set of recommendations and opted them in and they could opt out and it. It’s so obvious in retrospect, but at the time you know, look like we’re moving meetings and and this ah this opt in ah it was an opt in to move the meeting automatically like the algorithm would take over and move your meeting for you which we had heard from a lot of people that they were scared of and rightfully so you know you don’t want your meeting to move at a bad time. And if we do it at a bad time. You know we’re to get a terrible reputation there fire us. They’re going to go on Twitter and say bad things. Um, so we’re nervous about it. But we flipped the default and it worked ah it worked. Um, we had massive more adoption in terms that core feature set.

Matt Martin: That core feature set was able to drive more value over time. Um, and we’re kind of an automation product ah product so we exist the background so flibb that default wasn’t just about that point in time of getting that value. It allowed for consistent value over you know the following days weeks even months as that user engaged clockwise and that started. This flywheel of people using it getting value inside the organization and spreading and it was that really that flywheel of kind of organic product like growth that got us the next stage where. We could continue on. We could see the path. We could see the excitement. We could see how this thing could scale and that scale isn’t just important for startup scale. You know we all want to scale out our startups. We all want to get to massive adoption. But again going back to the mechanisms of the business. It’s critical because that’s how we provide value that scale is a prerequisite. Inside the organization for us delivering value. You know today we’re wall-to-wall inside of Uber’s Engineering Department Netflix Pinterest instacart etc but we need that scale in order to go to that department and say hey you know here’s the value here’s what we’re providing for you so that was a key key un lock and it. Man I mean you know look I’m not going to bore your audience with all of it. But you’ll find on these journeys and you’ve talked to some of the best founders of the world. It’s these little moments where you you switch a default or you make a tough decision that feels like it’s you know one-way door.

Matt Martin: And you find yourself on the other side of it. You’re like oh holy shit like that. Really that was the inflection point. That’s what made the difference and the only thing that’s different about that decision or others is that it worked you make tons of these that don’t work you know and you you don’t look back on those as being inflection points because they didn’t work but you just got to you stick to your guns. You keep experimenting you keep trying you take a few bold calls and eventually you find one that clicks. Hopefully you find one that clicks and for us. Um, that allowed us to get to that next stage.

Alejandro Cremades: So as we’re talking about getting to different stages life cycles. You also bring a financing cycle. No with the right people with the right you know also network to help you to get to that next day to alock that next stage. So I guess in that note. You were talking about a excel a earlier. How much capital have you guys raised today and how has it been also the journey of of going through all this financing psychos as well.

Matt Martin: Um, about $76000000

Matt Martin: It’s interesting. Every round is is different. Um, it’s been. You know I think we’ve been incredibly fortunate ah because the quality of investor that we have on our board um is fantastic. You know working with. Ah, John Lily Ajay Agarwal Lucas Swisher Steve Lawughlin worked with an alassia and orthodo slack fund. We’ve had some fantastic investors and I think they’ve all rallied around the expansiveness and the scope of the vision. You know if if you can help solve the issue of. Ah, productivity inside of organizations and having um, bad fragmented schedules that people aren’t happy with obviously that is a massive massive opportunity. So um I feel very fortunate in that regard. But every round is different. You know sometimes. Sometimes you approach around and it’s out of necessity and sometimes you approach around it’s out of opportunity. Um, and those are very different postures and I’ve been in both of them.

Alejandro Cremades: Now obviously you know like with investors of this caliber. You know vision is a big one. So let’s say you were to go to sleep tonight Matt and you wake up in a world where the vision for clockwise is fully realized what does that world look like.

Matt Martin: So we’re going to create this world. Um, and I don’t think it’s that far off I I want to create a world where you alejandro can have this schedule that you want to make you the best version yourself and every facet. Um, I mean eventually we focus on work today. But I mean eventually in work and personal and in the combination of those 2 if you need to go heads down to deliver a huge project. We’re going to enable that for you if you need to get time to go take your kid to school where to and get that for you and. Our vision is to give every knowledge worker on the face of planet schedule they love and I really mean love something that makes you feel better when you go home at night. Something makes you feel more productive and through the combinatory effect of that we’re to make organizations more productive ship faster deliver more drive more revenue what that looks like on the ground I think. Is every single person has a personalized calendar assistant that helps them navigate their workweek and get what they need. Ah so if it’s it’s everything from the little simple stuff like. Hey Alejandro it looks like you missed as um, adding a Zoom link to this meeting on friday. Do you want me to add 1 for you all the way the massively complex which is hey you know let me know what your goals are for this quarter and I’ll make sure to help you track them and make sure that you have time and you’re addressing them. Mom.

Matt Martin: And on a weekly basis hey a hundred looks like you don’t have enough time this week to go heads down. Would you like me to move some of these meetings around to to facilitate that for you and then I can block it off and make sure it happens or you know hey this meeting is at Nine Zero P M and it actually looks like you’re supposed to go to dinner with your wife that that evening let me fix that for you right away. I think that we can enable that world where you don’t have to expand mental resources. Um or time in a wrangling or facilitating that schedule and by giving everybody in an organization. Ah that capability were able to coordinate amongst people. Again in that shared space as a coordinator as a facilitator to make sure that everybody is getting maximally what they need and that the organization is getting the most on the schedules to their people.

Alejandro Cremades: My god that that that sounds and looks like a beautiful world to me Matt so um, let me let me now ask you differently here because we’re talking about the future but I want to talk about the past but doing so with a lens of reflection because obviously you’ve been at it now for.

Matt Martin: Yeah.

Alejandro Cremades: You know your way to 8 years you know with clockwise which in do years you know in startup world is absolutely incredible. So so let’s say I was to put you into a time machine and I bring you back in time to that moment where you are going to be walking away from the you know whole experience that you had with salesforce and then also with relay iq.

Matt Martin: Um, yeah.

Alejandro Cremades: And let’s say you know you had the opportunity of stopping that younger self that was coming out of you know the salesforce you know umbrella and that that exact day when that happened and when you gave your notice and let’s say you were able to have a sit down just grab that younger Matt and. And sit down younger mat for a coffee and you were able to give that younger mat 1 piece of advice for launching a business. What would that be and why you know what? you know now.

Matt Martin: So The the piece of advice that I would give myself is your startup is not you you and your startup are different things and you need to appreciate that now that advice is easy to state I Think it’s really hard to internalize and I don’t know. Even now if I told my younger self that if I would be able to really feel that without having gone through the journey that ah that I’ve gone through with the startup and and let me unpack that a little bit because I have a conversation. Um I’m incredibly competitive like I want to win. I Want to win because I want to deliver the vision of the market. But I Also want to win just because I like winning and so it’s really tough for me and I see this with a lot of founders. A lot of startup leaders. A lot of ceos to separate out the business from my personal self-worth. From who I am from who I perceive it myself as if I’m losing I feel bad about myself if I’m losing I feel like I’m you know worthless. Ah, and that you know to some degree that’s motivating. But I think can be really paralyzing because you can get to a point where you’re operating out of fear or you’re operating out of loss aversion or you’re operating out of ah you know emotion and that is a bad place to be I think I’m at my best when yes I want to win.

Matt Martin: But I’m taking it with a business mind approach like we have resources on our back we have people. But yeah, we’re taking big bets and you know what look we’re gonna lose some That’s not the end of the world. We’re going to wake up the next morning we’re to try again and that’s not an evaluation on me. It’s not a vauation on my team necessarily sometimes it is ah but it’s It’s just part of the process and ah 1 of the pieces of advice I was lucky to get from another more seasoned founder at the outset. Um, it’s a little bit of a a little bit of a nerdy characterization which is true to the individual. But I really like it. You’re saying you know, look like if you think about this journey as you’re on, you’re on a boat. Trying to cross the ocean if you can control the amplitude of the waves just think about how much less distance you have to travel if you’re sailing on smooth seas. You know the nautical miles you’re traveling is way way shorter than if you’ve got these huge waves that are going up and down on. And that’s part of the founder psychology if you’re able to control those waves you know where those downs are so low and those highs are so high and you can even kill yourself a little bit. Um, the journey is much better and you’re a better operator and for me personally going back to the advice I think it’s about separating out that. That aspect of self-worth you know that load doesn’t have to be that low because it’s not about me. It’s not about me being you know a piece of crap or something. It’s about the businesses and do well right now? What are we going to do to solve it.

Alejandro Cremades: Wow I Love that I love that so mad for the people that will love to reach out and say hi. What is the best way for them to do so.

Matt Martin: Oh man isn’t that the question right now I mean what do we do x Twitter threads I have resorted to Linkedin I you know I found it. You know people are a little bit nicer in their professional self are attached to their profile. So find me on Linkedin. You can look me out Matt Martin’s clockwise. You’ll find me really easily ping me there. Ah follow me there. Um I would love to talk reach out anytime.

Alejandro Cremades: Amazing! Well hey Matt thank you so much for being with the deal maker show today. It has been an honor to have you with us.

Matt Martin: Thank you so much and thanks for what you do all hondra I love this series I love people speaking Authentically I think there’s so much value when we all talk to each other about the journey.

*****

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