Reclaim // a smart calendar assistant helping find time for your real priorities [UP089]

Jay Clouse 0:01
You know, Eric on the show time and time again, founders talk about the importance of hiring great employees.

Eric Hornung 0:07
And they always say it’s so hard and so important early on to hire the right person.

Jay Clouse 0:12
It makes a lot of sense that it’s difficult because most founders don’t have experience doing high level searches or hiring top level talent.

Eric Hornung 0:19
And they’re also limited to their local talent pool a lot of the times.

Jay Clouse 0:23
That’s why a lot of founders choose to work with SPMB, the one of the fastest growing executive search firms in the country. For over 40 years. SPMB has specialized in recruiting upper management and board members to early stage VC funded startups and larger growth stage companies do.

Eric Hornung 0:38
They bring the knowledge of a large global firm and combine it with the personalized service and attention of a boutique.

Jay Clouse 0:45
They have a dedicated team focusing on the Mountain West and Midwest emerging tech markets. So no matter where you are in the country, if you’re trying to hire top level talent SPMB can help you out.

Eric Hornung 0:56
If that sounds like you, you can go to upside.fm/SPMB to learn how they are closing hundreds of C level searches annually.

Patrick Lightbody 1:11
The lightbulb kind of started to click I wouldn’t say it was like an instant on it was more like a warm glow. But where where we realized that there’s all these competing priorities that leadership at companies know nothing about.

Jay Clouse 1:27
The startup investment landscape is changing. and world class companies are being built outside of Silicon Valley. We find them, talk with them and discuss the upside of investing in them. Welcome to Upside.

Eric Hornung 1:55
Hello, hello. Hello, and welcome to the Upside podcast. first podcast finding upside outside Silicon Valley. I’m Eric Hornung, and I’m accompanied by my co host, Mr. Host with the most himself, Jay Clouse.

Jay Clouse 2:10
We are back with the Upside outside addition, on the patio, hosting you, Eric hosting you in our home, I’m looking down at the patio rug. We had a little fire last night. And I’m seeing that a renegade Ember has burned a hole in this rug, just like it’s burned a hole in the cushions of some of this outdoor furniture.

Eric Hornung 2:35
But I love the fire last night.

Jay Clouse 2:36
But the fire was nice.

Eric Hornung 2:37
I’m so happy that I was able to get down here a day early. We were able to hang out in person, I was able to see the house. And I am so impressed with you and friend of the podcast, Mal’s ability to host on a whim. I don’t even tell you I was staying here.

Jay Clouse 2:52
You know, it was good, though. Because if you hadn’t done that, I probably would have continued working last night, I wouldn’t have had a fun time I wouldn’t have had a memorable time. I would not have been as present here with Mal. And I would say you really helped me to reclaim some of my weekend.

Eric Hornung 3:08
You sometimes you got to schedule time for yourself, Jay you guys schedule some personal time.

Jay Clouse 3:12
But sometimes you forget to schedule personal time and it’s helpful when somebody essentially does it for you.

Eric Hornung 3:16
And that’s where Reclaim comes in. Today’s guest is Reclaim.AI

Jay Clouse 3:21
Patrick Lightbody is the co founder of Reclaim.AI, which Eric we got in touch with because we were talking about how much we love SavvyCal for the show. Listeners of this show, SavvyCal is a new sponsor that we’re very, very excited about. And if you need scheduling help, you might want to go to upside.fm/SavvyCal , but Reclaim another interesting innovation in the scheduling space that at first I thought was a competitive of SavvyCal and quickly realized, Oh, no, this is actually very complimentary, and probably something I should download and start using right now.

Eric Hornung 3:54
I love when I run into people on Twitter, I was talking about my SavvyCal zapier setup, my work versus personal calendars. And Patrick just popped into the comments and said, you really should try Reclaim it’s what I use and it worked perfectly with SavvyCal.

Jay Clouse 4:09
Founded in 2019. In Portland, Oregon. Reclaim is a smart calendar assistant that blocks flexible time for anything you care about. Reclaim is intelligence and automation for your calendar that aligns your priorities. The time you spend every week empowering you to rapidly rebalance your schedule and defend your time to work on what matters. This is essentially Eric a well it’s AI little robot in my calendar that actively blocks time off for things that I continuously deprioritize like lunch, like exercise, like morning and afternoon catch ups on email.

Eric Hornung 4:45
And those things are really important. If you want to live the one life you have the best way you can.

Jay Clouse 4:49
It’s true and if you dear listener are trying to live your life the one life you have the best way that you can, you might want to visit our friends Ethos Wealth Management at upside.fm/ethos. Eric, Reclaims this point has raised about one and a half million dollars that happened in December of 2019. And on their website, they say that Reclaim is free right now through 2021.

Eric Hornung 5:13
I’m on board, you’re on board. And dear listener, if you’re on board with Reclaim, let us know shoot us a note @upsideFM, or something a little longer at hello@upside.fm stack, Reclaim together with SavvyCal and join the Upside scheduling stack.

Jay Clouse 5:33
Eric, we got to make some big changes to how we do operations here at Upside.

Eric Hornung 5:37
This feels like an intervention Jay.

Jay Clouse 5:39
It’s a bit of an intervention, I have to give you some tough love. We’ve had some calendar problems over the last couple of weeks.

Eric Hornung 5:44
I’ve had some calendar problems, youdon’t have to throw the third person on this.

Jay Clouse 5:47
I do like to take the blame for you. But this one is on you. And Eric, I think we have found a solution to our calendar and scheduling problems.

Eric Hornung 5:55
But there are 101 scheduling tools out there Jay that can help you avoid the awkward dance of finding the time to meet.

Jay Clouse 6:01
But this tool is by far and away the best one I’ve seen and I have looked at a lot of scheduling tools. And I am talking about SavvyCal.

Eric Hornung 6:09
SavvyCal makes it a collaborative effort allowing you to personalize links and allow recipients to overlay their own calendar on top of yours.

Jay Clouse 6:18
It’s going to make booking guests for Upside and even just one on one conversations a complete breeze. You gotta see what this looks like you got to see how it works. Because you’re going to ask why wasn’t it always this easy?

Eric Hornung 6:28
You can sign up for a free account at SavvyCal.com/upside. That’s SavvyCal.com/upside. And when you are ready to test out a paid plan, use the code Upside to get your first month free.

On Upside we’ll start with a background of the founder details about the history of Patrick.

Patrick Lightbody 6:59
Yeah, and thanks for having me on here. I don’t know I’m a I guess a computer scientist turned entrepreneur turn Product Manager sort of that last part, I’d say, you know, when people ask me like so are you an engineer? Are you are you in product? I’m like, Well, I sort of fell into product management. But I don’t identify as a career Product Manager, even though for the last prior to starting Reclaim. That was kind of what my thing for, I don’t know, eight or nine years. But no, I’m I grew up in the Bay Area and did some computer science and you know, kind of classic stuff, you know, trying to build video games, and you know, what kids often do and how they look, get into tech, and started doing some some software, you know, real software and like C in high school. And then I went off to college and thought, you know, hey, I’ve already learned a little bit of software, why don’t I try hardware. And so I briefly majored in electrical engineering, and I totally failed out of that, like that was just it. Once I got into analog, it was like no bueno. And so I switched back to computer science and graduated and kind of just went and did a career of the short career of professional software development for a couple startups. And is at that point that I got the itch to do my own startups and and so I did a couple from there, really oriented in testing and monitoring and kind of performance space. And that kind of set me on my career trajectory until Reclaim, basically, because I did a startup that was cloud based browser cross browser testing. And it wasn’t called Cloud at the time, they didn’t know the word hadn’t been created, because this is like 2005, I believe 2006. And so it’s just a VMware hosted on an on a server, and then did another startup that was cloud based load testing. And then eventually, after I kind of got through the arc of those two startups, found my way to a role as the first product manager at New Relic and I was with that company, as it grew its product portfolio and went through its IPO and then continued on there actually left and then came back for a little bit, but that’s a story that doesn’t really matter. I’d say it’s a it’s a blip in the career arc and then ultimately settled it on Reclaim. And we can talk more about why I did that.

Eric Hornung 9:15
When you think about leaving to start something new. Are you doing kind of nights and weekends hustle until you feel like it’s right or are you like, Nah, I’m just gonna cut this clean. I got this idea. I’m gonna run after it.

Patrick Lightbody 9:27
Yeah. Like my brains going bad pausing because I’m like, Okay, can I rewind and remember the transition when I was at Jive software, transitioning to my first startup. And I want to say there were some definitely like a little bit of prototyping but but absolutely not a complete product or even a, you know, 1% complete product. It was more like just making sure kind of the concepts could roughly work. And I can’t say if that was work that was relevant to the startup or work that was relevant to My just general Open-source contributions, because I’d say that’s the other part of my career that that kind of threaded through everything is that I was involved in Open-source, most of that time, especially kind of out of college, and then up through my focus on performance monitoring and testing. And just naturally, when you’re kind of doing Open-source, it’s it is a hobby, it is nights and weekends. And so, you know, I found myself especially with those first two, where it was, it was about one of the Open-source projects, I was involved in one cross browser testing framework called selenium, you know, that work was was intertwined with the Open-source work to some degree, and it was me experimenting, but I’d say mostly, I just took the plunge. And especially so with Reclaim, that was a little different, you know, it’s kind of thinking about the first two, because I can imagine myself kind of doing some of that hustle on the side, it was very different coming to my third serve, because there’s about a 10 year gap between my second and third startup. And during that time, you know, bought a couple of houses and had mortgages and moved a couple times, you know, and had three kids and a dog. And just like all the life stuff that kind of happens in your, your middle ages. And so there was no bandwidth, by the third time to do something, you know, significant on the side, what there was, was a little bit of discussions with venture capital, but nothing in terms of actually building a we didn’t actually build until, until we, you know, basically a month after we both left our jobs.

Eric Hornung 11:31
I want to dive down a quick rabbit hole here. Maybe not too quick, who knows, you don’t actually know where rabbit hole gets you. But open source, I think you’re the first person we’ve had on the podcast to has talked about it at all. And I’m not familiar with the general culture, how do you get involved with open source projects, the open source community? And like, Can you describe a little bit of the open source culture.

Patrick Lightbody 11:56
My description could be dated, although I suspect it’s pretty much the same, except the replace like IRC with Discord, or Slack. But you know, and I guess it, you know, now there’s like, pull requests, and there’s a whole culture around, like, you know, if you just send a blind pull request versus like, if you kind of like ingratiate yourself with the developers a little bit, but for the most part, I imagine, it’s, it’s pretty much the same as it was 20 years ago, which is, you know, you find a project, you initially are using it, you find opportunities to improve it, and, and you kind of start to connect with the the main developers behind it, you know, slowly, slowly, but steadily kind of become a familiar voice in that in that little community. And these can be very small communities. I mean, they might be, you know, five or 10 people for certain projects. The main one I was involved in was a collection of open source projects, that was called Open Symphony. And it was, I forget who exactly founded it, but it was, I want to say it might have been the at least Co, sort of Co founding rights might have been the the co founders of Atlassian, Mike and Scott. But it was definitely a small group of people like those guys, me, some folks from thoughtworks, that consulting agency, was really heavy on agile. And we all hung out in IRC in on F net, hashtag Java, and just chatted about things. And I’d say, you know, there were like the regulars in that community who were all sort of becoming contributors to Open Symphony. And I don’t know, I mean, that was basically it, there was a lot more community building back then I’d say, that’s probably a little different. And you can emphasize, you can kind of focus more on the code and the relationships back then there was no GitHub. And so, you know, literally, there’s a lot of infrastructure to build the community. And that was, even after I long after I was done contributing code, you know, meaningful code to the community, I still spent like another, I don’t know, five or 10 years, like sort of feathering down my involvement. And all I was doing was like IT administration and keeping the, the website updated just as a way to stay connected and kind of feel like I was, you know, contributing something, even though I didn’t have code contributions as much anymore.

Jay Clouse 14:15
I’m gonna pull us out of this rabbit hole, Eric, I’m sorry. Because we spend the entire time talking open source for sure. I want to hear what brought you to Portland. And how difficult of a decision that was to move from your your home area of the bay area to Portland.

Patrick Lightbody 14:30
Yeah, you know, it wasn’t a hard decision. But it was also a decision that I totally thought was going to be a two year stint. I was at a startup right out of college, I worked during college at Cisco Systems, which helped me come out of school debt free, which is pretty awesome. And so I’m forever grateful to that company. But I also knew like, yeah, this is not the kind of like environment I want to work in. I want to be in something you know, much smaller, much more, you know, direct connection to the customer. And so I Immediately was just like looking through, you know, job listings, I, I don’t know, this could be my memory just playing tricks on me. But I swear, I was looking in classifieds. But you know, I’m not that old. And so I don’t think I was, but I have a memory of seeing Spoke Software and like, you know, tiny little like newspaper print. But whatever it was, I found them a small startup in Palo Alto. And it was a lot of fun. And we were this close to using my fingers here to being LinkedIn. And it was actually a pretty important, like business lesson for me. Because I’d say the biggest problem was the business plan. And in particular, we thought it was just this example of like having the right tech, but just the wrong distribution channel, we thought that people really valued their privacy and would want a, you know, close network for each individual enterprise. And that there you sort of have like LinkedIn enterprise, you know, for every company. And then we spent all this time building like wide area graph, like shortest path graph stuff, so they could still connect with each other. Turns out, nobody wanted that they wanted just an easy to use website. And so that company struggled and started falling apart. You know, amazing people came through there. And might like, Mike, my cube mate at the time was Chris Kelly, who left and spoke to become the Chief Privacy Officer of LinkedIn. So we were all kind of like figuring out what to do. And I happened through those open source connections, I happen to know they Jive co founders, because they were using a lot of the open source tech that that I was working on. And they were 10 people, 8, 9, 9 people, something like that. And they just moved the company from New York City to Portland, they were kind of had concluded, too expensive in New York, let’s go find somewhere else to go. And they were there. They just moved the company there. And they asked if I want to join. And I said, Sure, because this company doesn’t seem like it’s going to be around much longer than I’m currently working at and what the hell, this sounds like an adventure. And I’ll be back in a couple of years. And clearly that wasn’t the case.

Jay Clouse 17:07
Well, let’s, let’s fast forward, then you spent the next well, up to today. So like 15, 16 years in Portland, going back to New Relic at one point, but then looks like in 2019, you started Reclaim. So talk to us about what started Reclaim for you, and what convinced you to take the leap and go full time on that?

Patrick Lightbody 17:26
Yeah, I’d say there were a few motivations, a few sparks that kind of got that fire going. A couple of them were really early on in my career, actually a little bit of time at Spoke Software. Yeah, something that sat with me for a long time was the power and the value of the data that just comes from people using everyday collaboration software. You know, in the case of Spoke, we had an outlook plugin that watched how people were emailing each other. And one of the unique things I still think is missing from LinkedIn is this idea of understanding how strong a relationship you have with someone by observing how much how frequent and what times you communicate with them. And so you know, that kind of just planted a seed in the back of my head for the last 20 years of like, you know, there’s I want to do something with that more down the road. Then I went to Jive Software, and, you know, Jive was very much in kind of split between internal and external collaboration. But it got me excited about, you know, the value of collaborative software, and productivity software was, you know, closely adjacent to that, and kind of embedded in a lot of the collaboration tools. And so that was another one of those like, okay, store that away, let’s, you know, maybe we’ll come back to that at some point. And so those are, for me for my kind of personal motivations, from a kind of more professional and shared motivation. Henry, my co founder, who I had met at, at New Relic and worked with for a number of years, he and I both had one just kind of decided, you know, our time here at this company is coming to an end. And it would be a lot of fun to work together. And, you know, pretty quickly you realize, like, there’s not a lot of places that are both looking to hire two VPs of product management concurrently. So you know, what can we do there? And obviously, you start up and seem to be the, you know, quick solve for ensuring we are both working together. And then there’s sort of like the idea behind it. And initially, we weren’t thinking about doing anything around productivity or calendars or anything like that. We were actually thinking about, you know, kind of, let’s take what we’ve learned from New Relic, and kind of extend it, and it, it wasn’t the kind of natural thing that I think a lot of folks would have thought is like, Well, why not just go do another monitoring kind of startup? And God knows we got that same question thrown at us by parade of investors along the way, but it was more like we were taking a strategic look at the market and we were asking like Okay, look, it seems like with Cloud and Open Source, the world that New Relic and Datadog and Grafana live in is going to be challenged not not not, I don’t mean to imply like it’s a bad market to be in. But it’s going to get compression, it’s going to get term. And so, you know, if we were kind of going out and setting something out, they could kind of benefit on this, like, all this turn, what would that be? And we concluded, like, it’d be something that’s about the workflows and interactions that are just a little upstream and a little more removed from the actual telemetry data that those businesses were collecting. And so initially, we, as we kind of pulled on that thread, we initially were thinking something closer to like, a platform for Site Reliability engineers, where they could respond to incidents, and kind of bring people together into a war room, there been a couple startups kind of like that. And then we were kind of envisioning, like, all these workflows that could kick off, including, you know, scheduling meetings to do retrospectives, and things like that. And so that was, that was kind of where we started. And we were just, like, casually talking with, like, friends and acquaintances about the idea. And saying, like, you know, do you think we could do something that would help your teams be more efficient and be more productive, and what we’re hearing from them, it’s like, you know, like, that’s cool, like agile, DevOps, Cloud, Open Source. All those things are, like, nice and nice, sprinkle them into my team. But you know, honestly, the number one driver for whether I have a team that’s really effective or not, is how involved my engineering manager, my product manager, and my design manager are in the team’s like, day to day. And that resonated a lot, because in our role, where we were kind of, you know, senior leaders, but not so senior, that we were disconnected from, like, you know, teams on a pretty regular basis, we do a lot of operational reviews of teams, and you’d kind of hear, you know, you’re a director of engineering or Director of Product Management come in and say, Okay, I’ve got these three teams, and, you know, this one’s going really well. And the common thread was always like, high engagement from at least one of those, those three roles. And so when we pull the thread on that, what we found is, you know, when we went and talked to those people, they’re like, I would love to be, you know, pm classic pm answer would be, I’d love to be involved in more of the day to day with my team and be in the, you know, in the room with them, you know, physically or virtually. But you know, I get pulled into sales escalations, I get pulled into, you know, project management reviews, I get pulled into all these things. And, you know, the light bulb kind of started to click, I wouldn’t say it was like an instant on, it was more like a warm glow. But where were we realized that there’s all these competing priorities, that leadership at companies that know nothing about they, you know, every day, it’s like the meme of the, you know, the guy sweating is trying to press the button, then it’s like, except this meeting or except this meeting. And it’s a decision that in isolation is small, right, a single choice of an hour where you spend your time is not going to make or break a company. But over time, those choices wear down the employees and also result in fragmented focus for for companies themselves. And that got that’s our getting us really excited because it’s starting to sound like, hey, this, this might be something we can pursue, that helps make individual people happier, but also, like, help solve inefficiencies at the kind of the enterprise level. And so that that was what we decided, let’s go do this.

Jay Clouse 23:29
So how has Reclaim? How is the product changed over time? Because when I was doing research for this episode, you know, I wouldn’t have thought that you were doing helping enterprise customers, help their teams prioritize their time better, necessarily, to me, I thought it might even be a consumer play. So talk to me about how the product has changed over time and and what the strategy has been.

Patrick Lightbody 23:53
I mean, the short answer for that is because we’re not yet and although that is our long term mission, it doesn’t make a lot of sense to put that on our website, not because it’s some secret, but because we’re trying to appeal to the, the prosumers I guess, not the consumers, but you know, the the professional individual workers who are inundated with with demands for time. So our first mock ups that we were we started with, and then ultimately went into, you know, prototyping, we’re really oriented around this idea of meeting the fragmentation and meeting and time alignment to your priorities. And it’s a it’s still something that’s really important to our mission in the like, medium term, maybe even near term now, but we did we learn something along the way I’ll get to in a second about and why for why we didn’t launch with that capability. But the basic idea was, you know, fire up Reclaim, and write in your, you know, up to five stated priorities and whatever. Whatever scope and orientation and time duration that you wanted. And they can be personal or professional, we had sort of advice like, you know, ideally most of them are professional. And ideally, most of them are measured in like weeks to a few weeks to a few months, you know, evergreen goals, this is kind of like stuff I was bringing in just from like coaching, you know, other leaders in New Relic, like, an evergreen goal of build a great product is not really going to orient you around, you know, thoughtful decisions around how you spend your time. And, and then similarly, you know, a task is not really going to be helpful, like that’s not a priority, and it’s not thematic. And so we asked our, you know, about 100 or so users we recruited to the prototype, to write these things in, and then they could go in with color coding associate the the time on their calendar with those priorities, and then they get back some analytics. And that was basically what we built. The idea was that eventually we’d make recommendations around how to, you know, move things around, or how to, you know, say no, and give you some kind of like, initial canned responses that can help you save some of that political capital. But but also give a little more context to why you were declining or, or delegating, you know, requests for your time. You know, it was interesting, I think it’s still something that, I mean, those ideas are not bad ideas, they’re things that high functioning executives do all the time. But it wasn’t, we learned pretty quickly, it wasn’t the right place to start software, because it asks a lot of a lot of information upfront, I mean, in a sense, it wasn’t that much information, you know, writing five things in, and then associating your week’s agenda with those five things is in, you know, in a way, from a data entry standpoint, a lot less than, say, getting started with an advanced email client, where you might label you know, half a dozen labels, and you might have hundreds of things to rip through, or 1000s, or look, or infinite, depending on how you’ve been managing your backlog. And so in that sense, from a manual labor standpoint, it wasn’t that much more work. But these were like, these were like, really intense questions to ask someone actually, like the moment like we would watch our users and they just freeze, they wouldn’t know what to say. Because I mean, the reality is, is like, even if you ask yourself some weeks, no matter how high functioning you are, some weeks, you’re just like, God, what is the top two or three things that are most important today?

Jay Clouse 27:27
So this was gonna ask , what are those? What are those intense questions that you’re asking?

Patrick Lightbody 27:31
I mean, that’s literally it is like, what are your most important things? And it sounds so simple, but distilling it to a list of say, three to five, is actually pretty hard for people. At least when it’s like scoped, right? You know, I mean, it’s pretty easy to say, like, you know, learn, grow my career family, but those aren’t gonna like help you make any thoughtful decisions about how you, you know, how you might better architect your time. So yeah, that would have been kind of fall 2019. And we concluded that the best thing for us to do was to get to action much faster, to do something to meaningfully help the user in some way, that that an analytics, initial MVP, that was just analytics was not going to be compelling enough to keep users to come back to the product on a regular basis. And more importantly, to promote it, it would just kind of go to the back of their mind. And you know, all the classic startup stuff of like, you know, a lot of people, we talked to our friends. So naturally, they told us, you know, how great of an idea it was, but you could observe in the behaviors that they weren’t coming back to try it out week, you know, every day or every week. So I don’t know if you’d call it a pivot, as much as you’d call it initially, sort of an additional like we had initially, initially, we had the idea that that was our pro version of our product, and that was going to kind of keep building along. But we would go make like a free utility, even actually, under an entirely different brand to start, that was easy to search and discover. And that would be kind of a feeder, into into Reclaim the pro version of the product that we were building. And that was where what we call life work calendar was born. It wasn’t work life calendar, because we couldn’t get that domain. And we were we were low on funding and scrappy. So we went with life work calendar, and to this day, you can go to lifeworkcalendar.calm, and it’ll redirect you to Reclaim and we decided to just like do one thing that we knew we could do action on. That was like a meaningful problem that all the people we’ve been talking to had, which was the issue of blocking out time for personal commitments. You know, I’m sure you both have this challenge as well, right? You probably have more than that too. You probably have like your work calendars and projects like this and you know, side gigs and personal calendars, like, you know, two is a minimum for most people. And then some some people have many more than that. You know, I could empathize With the stress of it all, as silly as it is, it’s like those moments where you’re like, driving to the dentist office. And then like a sales rep calls you is like, Where the hell are you, you know, the the customers here, I’ve got the lunch platter set out, you’re supposed to be giving a session and you’re just like, Oh, my God, how did I, how did I screw this up? And so we just said, let’s just like build something that we can we can automate. And that will keep us like in people’s minds on a regular basis. And it’s like, you know, there was a executive at our New Relic Hillary who joined it from it was she was our president and CFO for a number of years, she came from Salesforce. And she would often talk about the stick in the eye problem, you know, what is the thing that is most acutely painful, and like this was one of those simple, simple pain points that we could solve pretty quickly, we’d already built up the infrastructure to sync with calendars. And so it wasn’t a big leap to start taking action. And so that’s where we got started. So in in February, I want to say is February 2020, maybe late January, we launched that product on Product Hunt, and started, you know, getting real users.

Eric Hornung 31:10
I wish I would have found that product in January 2020. When you said we both have calendars, the way we met was literally on Twitter, I think I laid out that I have multiple calendars, and it sucks, they don’t sync, and you responded. So definitely a something that I feel deeply, personally.

Jay Clouse 31:30
Talks me, Patrick about, since since this is an audio medium, and people can’t see the gifts that are on your website, walk me through a user’s experience using Reclaim and how that looks for them.

Patrick Lightbody 31:41
Well, literally, the onboarding process walks you through, basically the three major features we have today. There’s a couple other sort of, I call them minor features. But the three things we asked you to do are well, one, you know, you got to connect your calendar. So there’s got to be some element of trust. It’s it’s a less sensitive data source than say email, but it’s still a pretty sensitive data source. You know, lots of people have different opinions about you know, who can see what on their calendar but ultimately Reclaim need to see all of your work your at least your work calendar and and have full access to it. And so, you know, there’s an element of just what the hell’s this crazy robot going to do to my calendar? And is it gonna just cancel all my meetings or something like that? So, you know, a couple steps are just building trust, you know, part of why? I mean, some some parts of like brand and design are just also trusts exercises to make sure people feel like we’re we’re not this like rinky dink operation. Joke’s on them, we’re only eight people. But no, I tease. So then once they’ve connected their calendar, then we just ask them three questions. I mean, it’s literally just three questions do you want to have Do you want us to block out lunch for you. And we give them a little animation, that just shows how, with Reclaim, we will adapt your lunch meeting that we put on your calendar each day. And we do some clever things there. It’s not necessarily obvious with the first animation, but people kind of discovered us as they use it for a few more days, not only are we moving the meeting, we are throttling the free and busy time on the calendar so that we can deal with the core tension that we set out to solve from the very beginning, which is busy, especially kind of that middle that meeting middle management layer at companies, busy professionals are in this constant battle between demands for their time from other people, and demands for their time internally to get heads down work done. And often they’re they’re comfortable trading off a little bit of those demands for their own kind of internal time, as long as they still get it done at some point. And so you know, the classic example is lunch, right? Most busy professionals are okay, eating their food, you know, they one they usually do eat their food, not always, but they try to, and they’re okay kind of shifting it around sometime between say, like 11am and 2pm. So we asked them, Do you want you want us to do that? And a lot of them say yes. And then we asked them, Do you want time to catch up on your inbox, because that’s another one of those universal pain points. And we show how we, there’s kind of two blocks at the beginning in the end of the day that again, will kind of dynamically move around. And then finally we asked them, Do you want us to block out time for your personal calendar? And if they say yes, then we need to date we need to connect the second account, and then they get a little confetti pop, and they’re in the product. And when they go look at their calendar, they start to see, you know, blocks of time. That’s a personal commitment and lunch and catch up. And, you know, it’s generally a pretty delightful experience for them.

Jay Clouse 34:53
I feel like I am right in the wheelhouse of who you’re talking to here. So I’m gonna ask you questions as a user here.

Patrick Lightbody 34:59
Yeah.

Jay Clouse 34:59
If you’re let’s say I start the onboarding process, and I say, Yes, actually, I forget to eat lunch every day, I would love for you to give me lunch. But I have a standing meeting once a week with like my leadership team at noon, right? So does Reclaim move that without asking me or prompting me. Do I have to be the calendar event creator to move that, how’s that working,

Patrick Lightbody 35:22
We don’t yet mess with moving meetings around. That’s naturally in our in our trajectory, because our long term vision is kind of aligning the time of an organization to the to the highest priorities of an organization. And while still kind of respecting the needs of the individual people and their priorities, and, you know, trying to get the best path forward for everybody. And to do that, we’re going to have to orchestrate meetings. But today, we only mess with and that’s part of I think, why people are comfortable getting into our stuff is that we can say confidently, we will not we will not mess with your meetings that stand up, for example, will not be touched. Instead, your lunch will move around the stand up. So if you ever convince the rest of the team and say, you know what the hell everyone this is my lunch hour and you can move the meeting, then Reclaim will jump in and take that slot. But But until that day, will be before after it. Those are called habits and they can you can set policies you know, kind of what’s the min and max duration, your you’ll be comfortable having what’s the you know, earliest starting time, the latest ending time, which days of the week? Do you want those things to happen on that kind of stuff?

Jay Clouse 36:34
I’m literally working through the onboarding right now, as Eric asked his next question it’s interesting, because the first question, I was like, sync your work calendar. And I feel like I prioritize work and personal independent work kind of the same. So I had this like immediate question of like, Well, which one do I do. But I’m going full on work first, and I’ll check back in after Eric asked whatever next question he was asked.

Eric Hornung 36:57
How’s the, like, initial response of the market to this? Because when I first looked at it, and I think when Jay first looked at it, like, Oh, it’s a calendar app, and there’s all of these calendar apps, there’s Calendly, there’s SavvyCal, there’s all of this stuff that’s going on out there, people tend to lump it in off the bat with it’s another calendar app, or how’s how’s that felt from both investors and users?

Patrick Lightbody 37:22
Yes, they do. And, you know, there’s, there’s lots of calendar and calendar adjacent applications and services. But we’re in a, you know, a small group, where I wouldn’t say we’re in our own group, but but it’s like, on one hand or less, that you can count that are doing what we’re doing. There’s a lot that are in the scheduling space, you know, you mentioned Calendly, and SavvyCal, and x.ai. And Mixmax, there’s quite a few that are in kind of like meeting, note taking, you know, kind of productivity, those would be like the fellow app, you know, Navigator. And obviously, there’s calendars themselves, you know, Fantastical than Cal. But there’s not too many that are kind of in the business of orchestrating the time on the calendars. And we’re in that category. And so the first thing is, it’s not well understood. I mean, that’s not a thing people have really ever considered that robots might move events on my calendar around on my behalf. And so right off the bat, there’s an element of like, tied it, you know, people don’t search for that robot and robotic calendars or calendar automation. That’s not a thing they search for. Two, there’s the trust and comfort element of it. And so, at some point, we’re going to have to go on the offensive a little bit more and do a little more education. But at the moment, there’s enough kind of early adopters, people like you all who want to find it kind of intuitively grok it that that keeps us you know that we get enough signups just from that to keep us going for a while. So yeah, and then there’s naturally kind of questions like, how do you relate to these other things? Why aren’t you a calendar app? You know, that kind of stuff? And we have answers for all them. I don’t know if we have enough time to, for me to give you all the answers. But ultimately, I will say, we concluded that the external scheduling space, the callin leads of the world, you know, there’s there’s a lot of really great companies out there. And we didn’t, we didn’t feel like we had anything new to add to that problem. But we did feel like we actually had something that could make that solution better. All that throttling. I mentioned the free busy time really works well with with those services. It’s like peanut butter and jelly because now you’re offering up a lot of availability and then Reclaim kind of sets in steps in with like circuit breaker logic and kind of blocks out the rest. But we didn’t feel like we had anything new to add directly there. And then on the app front, because our ambition is to be an enterprise software solution in the long run. We had to ask ourselves like what’s the best way to get wide adoption. Frankly, it’s really hard to come in and offer an alternative, either front end or full front end plus plus platform of any of the core productivity software. I mean, that’s partly why Slack was so impressive because they, they built a new platform, and we’re able to kind of own that whole experience. But the reality is, is very few other companies that had traction doing that quick, you know, founded by, you know, one of the best technologists that are and entrepreneurs out there, you know, and had a great exit of like, I don’t know, $800 million, or something struggled, really displacing any sort of office productivity. There’s, there’s so many calendaring apps out there, there’s one called woven that just recently announced that it’s shutting down, you’re just not gonna find success, I don’t think getting all the employees of a company to use it. And if you build features that depend on everybody using that software, I think you’re you’re asking for trouble from a distribution standpoint. So we decided what we wanted to build was something that could work with whatever calendaring app you use, and worked with whatever scheduling service you use, and that we could kind of slot in and be compatible, but still have some viral properties.

Eric Hornung 41:10
You also have a integration with Slack is the goal to have integrations with whatever messaging service you use to?

Patrick Lightbody 41:16
Yeah, eventually teams will be added there as well. We’re kind of focused on kind of that Google, I don’t think there’s an acronym for it. But the workspaces, Slack, whatever, whatever stack? Yeah.

Jay Clouse 41:28
I just finished the onboarding, beautiful experience, very easy to understand. As I’m putting this together, you know, if if the first thing I connect is my work calendar, and then I connect that to my personal calendar. Who’s able to see that, like, if my work calendar, is an organization on G Suite? Is my employer able to see everything on my calendar and understand how am I spending my time if I signed up as an individual?

Patrick Lightbody 41:51
A quick aside, the topic of privacy and visibility and calendars is, is one that there’s a ton of education that still needs to happen? I mean, it is, it is not easy. And Google struggles itself. Yeah, because there’s sort of the calendar privacy level. And then there’s the individual events of privacy levels. And then there’s the topic of like, when you bring a third party, like, like, Reclaim into the mix, you know, what can Reclaim, see what can the organization see, at the end of the day, whatever you connected as your your work calendar, we call it the Reclaim calendar. That’s the thing that that we keep data on. And I can, I can just refer folks to our website, if they have questions about our privacy policies, and security and all that kind of stuff. But but we take that seriously, all the other calendars, we don’t actually even store in our database, it’s all ephemeral. So just when we see something changed, whether it’s a side gig or a personal calendar, just as it comes through, we kind of push it into whatever destination it needs to go to your work calendar being one source, but we actually support if you go into the calendar sync settings, you’ll see you can kind of set up sync policies and every which which direction. And in there are some privacy questions. I think this gets to kind of some of the interesting stuff we’re doing around privacy, because you can either block it out as just a simple busy block, and then your work would never know that you have a job interview. You can block it out as a personal commitment. And it’s funny, we’ve heard from some users, they’re like, yeah, I didn’t want to do personal commitment. Because if there was because that one’s marked actually as public. And they’re like, they said, like, I worry that if my employer sees I have too many personal commitments, they might realize I’m starting to job search. And so then then you can also bring the full details over. And we try to caution folks to be careful with that, like in that model can work really well. If you’re say bringing your work calendar into your personal one, or say you’re a consultant and you have three or four account, you know, work identities, and you’re bringing it into your consultancy account. Those models work great, but you probably you might not want to put your personal calendar into your work calendar verbatim. You might also not want to bring client eighth data and event details into client B’s calendaring system. And so you know, we’re still working with customers, we hold like regular office hours, and we’re pretty active on support. But I think there’s still work to be done to answer those questions for for users.

Jay Clouse 44:20
So right now I see that this is free the try through the end of 2021. What is this look like beyond 2021? Is this you know, you mentioned you’re going to the prosumer first, do you see this as being a direct to consumer company or do you see this being a tool that you go to the corporations and they they pay for and give seeds to their their people?

Patrick Lightbody 44:43
A bit of both not unlike, you know, I’d say Atlassian was one of the early pioneers of that model Salesforce to some degree, Slack as well. You know, our vision is people have a need, they find us they should be able to sign up and use either our free products or pay for with their own credit card or a corporate card, and just use it as an individual for a while. And then from there, you know, we see expansion into teams, that’s pretty common, you know, we’ll see on our signup list for the day these like bursts of activity from a single company. And it’s, you can kind of almost tell exactly what happened behind the scenes, you know, somebody Slack, sent a message, say, I just found this cool thing. And then more people sign up. And you can see this in our pricing plan. Even though we are not charging this year, we want to give people competence and understanding of like, where it’s gonna go. The idea is that eventually, a team leader, maybe like a director, or VP, could buy a number of seats still on that same card, but buy, you know, five or 10 seats for their team, and then just do kind of one expense, running it through. Once we’ve had enough adoption. You know, we’ve got some companies that are, you know, hundreds of people and we’re, you know, we’re coming on half of the employees are on board, where we can go call those people up and say we have a meaningful percentage of your employee base signed up for us, you know, why don’t we talk about an enterprise plan, and that would be where a more traditional enterprise motion would come in, but it’d be very well seated, I’d say, in our broad space, the closest comparison would be someone like Calendly, who, you know, for years has gone kind of to the individual, but they’ve got a small sales and marketing team oriented towards enterprise. And they’re growing that really fast now too. Who incidentally, by the way, the CRO there was the old CMO from New Relic. So we’re very friendly with those folks, just because I love love Patrick, the CRO over there.

Eric Hornung 46:39
How do you think about where you set the price, I see not, it’s scratched out, but $9 per user per month for pro and then $20 per user per month for team is just a stick in the air, this seems about right, or

Patrick Lightbody 46:53
We’ve had a decent amount of conversations with our early users, you know, kind of gauging value, there’s actually a kind of a product market fit survey that users will get when they sign up. And then there’s kind of relative comps in the industry, I’d say like Superhuman, for example, has set the high bar. And I would say it’s probably too high for the large scale adoption that we’re aiming for. So we kind of knew, you know, somewhere between zero and probably $30, for some element of productivity ish type of software was where we wanted to be. And then we kind of just, you know, work backwards from there. And we’ve gone through a few iterations of that of the segmentation and price fencing to kind of land on where, where, what you’re seeing today.

Jay Clouse 47:39
What is your vision for three to five years from now for Reclaim, and what needs to happen for that to be true?

Patrick Lightbody 47:46
Yeah, my vision is that hundreds of 1000s, if not millions, of working professionals view their use of Reclaim as a competitive edge to be more effective and more efficient and happier in their life and more more effective in their in their professional career. And, in large part, because of that corporate leadership, the C suite has access, you know, I’ll say it’s an early version of the product in the three to five year time horizon. But that corporate leadership also has access to an enterprise version of Reclaim, that gives them a sense that their company has a competitive edge, because they’re organizing themselves and making choices about where to spend their time and what programs to pursue, and more importantly, what programs not to pursue, that they that they view Reclaim as a critical tool for, say quarterly planning, annual planning, week to week operational reporting. You know, that’s a big vision, I think, long term that puts us in the same leagues have, you know, many it’s, I’d say it’s a new market, in a sense, but it’s broadly speaking, not unlike are somewhat adjacent to like project management and CRM type of software, where there’s this sort of system of record that executives go to to understand the health of their business, we think there’s a another and maybe even more important system of record, which is where people are spending their time and how it’s oriented towards the goals of the departments in their company. So that’s where we’d like to get to, there’s also, you know, those are like two nice goals, and they’re very one the enterprise one really needs the bottoms up data entry from from people to provide, but the same time, we can’t betray our customers trust, you know, they’re in trusting us to help make them the best version of them. And that might include making time for job interviews with another company. And, you know, obviously, we’re not going to share that information with their employer. And so we’ll have work to do to figure out like, Where’s the boundary and how do we do it in a way that that gives high trust and that is mutually beneficial, but generally, I’d say that the approach is going to be around work related priorities, you know, those are the ones that are pretty safe for a double opt in of people to say, yeah, I’m actually comfortable sharing, you know, with my employer, how much time I spent on program x or project y, you know, week to week to help the company be more effective. I think we’ll see some good traction on that. And, and that kind of work. You know, that’s like the, that’s the transition point. That’s where Reclaim, you know, I’d say in the next one or two years, we’ll start to build that enterprise version of that product, because we’ll then have, you know, a very complex and sophisticated graph of data. That’s the intersection of priorities, topics, people and time. And like, I mean, that’s basically what makes companies tick.

Jay Clouse 50:51
Well, Patrick, this has been awesome. I’m looking forward to giving Reclaim a spin myself. I’ve synced up my travel time, my catch ups, my lunch times. It’s all happening here. So thank you. If people want to learn more about Reclaim or try it out themselves, where should they go after the show?

Patrick Lightbody 51:05
Reclaim.AI.

Eric Hornung 51:09
Jay, what’s your favorite podcast app named after a fruit?

Jay Clouse 51:14
Gotta be apple.

Eric Hornung 51:15
Can you think of any other ones?

Jay Clouse 51:17
I tried really hard. But I didn’t want I didn’t want to wait for too long. I didn’t want too much dead air.

Eric Hornung 51:22
Hey, you know what’s worse than dead air? Not getting reviews on Apple podcasts from your listeners?

Jay Clouse 51:27
Oh, my gosh, it is the worst every day that I wake up and I don’t have a new review on Apple podcasts. I just look up the sky and I go, Ah.

Eric Hornung 51:35
I like how the first thing you do when you wake up is to look at Apple reviews.

Jay Clouse 51:39
If only I was lying, but I’m not. And I’m looking for new reviews for Upside on Apple podcast, Eric. And if you are listening to this right now, you could be that person that helps get the day started, right.

Eric Hornung 51:51
All you have to do is go to Apple on your iOS device or web browser, plug in and leave us a review. Five stars would be nice, four stars would be great. Let’s do five stars.

Jay Clouse 52:01
Let’s do five stars definitely prefer five stars. Even if you don’t use Apple podcast as your preferred listening app on an iPhone, please take a moment to rate us there anyway. It helps us bring on great guests. It helps us climb the charts. Our show will get better if you do this very simple act. So please, please.

Eric Hornung 52:25
Right, Jay, we just spoke with Patrick from Reclaim. We haven’t looked at or talked about our four outro questions in quite a long time, new listeners to the show might say what are you guys doing here?

Jay Clouse 52:38
What is this? What is this third segment of the show? Well, dear listener, it is emulating the four part process of a deal memo advocated for by Jason Calacanis, in his book Angel, and Eric off the top of our head, let’s go see what these questions are. How committed is this founder? What are the founders chances of success in this business? And in life? What does winning look like in terms of revenue and my return? And why has this founder chosen this business?

Eric Hornung 53:04
So a lot of those are founders centric. And we’re going to talk a lot about Patrick in this debrief. But I want to start with the business itself. Let’s talk about the product. Let’s talk about what return would look like how big is this problem? How big is this issue?

Jay Clouse 53:21
Well, as it stands, and since about talking with Patrick, I have been an everyday user of Reclaim for full disclosure. And I have to say, I did it on the call, the actual onboarding experience of the product is beautiful. This isn’t the question you asked, but I wanted to talk about it. Onboarding experience is beautiful. It very dynamically blocks time for me for the priorities that I say I wanted to block time for. And it’s great in that way. As I said in the intro product is free through 2021. So non revenue generating right now. And Patrick spoke about his goal of getting this in the hands of companies and businesses to help their employees be more productive. So when your market is companies, businesses, b2b, generally, my ears perk up a little bit, because I think that’s a shorter path to money to good money. But I don’t quite know the price point on this. But the market is very, very large. So how much does the price point matter? I don’t know what you think.

Eric Hornung 54:22
I came into this thinking that every calendar app is a calendar app. You know, everything’s trying to do the same thing, everything scheduling, but he made a very pointed distinction between scheduling apps like your Calendly and your SavvyCal’s, and what he’s trying to build with Reclaim. And I’ve never thought about the segmentation of the digital calendar like that before. So if we look at scheduling, there’s obviously a ton of money there. I mean, Calendly can be a billion dollar plus company and how many other scheduling apps are there? We have our favorite with SavvyCal. And I think there can be multiple billion dollar scheduling apps. On the productivity side. I’m kind of inclined to agree with Patrick but that’s a bigger market. Because it’s subject to, like scheduling is transactional, it happens once. And you can use the same links to schedule things. And it’s great. Both productivity, it gets smarter and better over time, the more you use it, and the more people that use it, so there’s some semblance of a network effect, maybe not a pure network effect there, which makes me feel like it’s stickier, bigger, and potentially huge.

Jay Clouse 55:24
I could see that you’re talking about Calendly. And its valuation. I knew I had actually seen a headline about this, even though Calendly has been a historically quiet and private company, valued in January of 2021. At $3 billion dollars, which blows my mind actually.

Eric Hornung 55:37
Bootstrapped.

Jay Clouse 55:38
Great, I agree with you on the productivity front. Also, if the company goes down a route of helping people be more productive, and, you know, wink, wink, reclaim their time, time is a very measurable value for businesses. So it gets easy to justify your pricing when you can point to the number of hours reclaimed, and tie that to people salaries, to hourly rates, things like that. So I could see it being priced higher than you might expect for what you may initially think is a scheduling tool for companies, but we didn’t quite get into that pricing model. So I’m kind of shooting the breeze on where that might land.

Eric Hornung 56:16
I think that it falls into our very large market space. And it would be nice to be able to do a bottoms up analysis, but we don’t have the data for it Jay. So we’ll say markets large, we’re excited about it, there seems to be opportunity for a larger turn here. And anecdotally, it is something that I would use I will use as soon as they launched the Outlook version of it. Because I think that there are a lot of people who don’t work in tech and don’t have Gmail based work emails, the majority of the old professional world is an Outlook based experience. And when that links together, when he can do Gmail and Outlook, there are a lot of people who just currently put busy on their calendar, who will use this product to make sure that they are communicating with their work calendar and not double booking themselves. As I do so frequently.

Jay Clouse 57:04
You sure do. But since we’ve moved our scheduling over to SavvyCal that has pretty much ceased to be an issue. And that’s a genuine plug for our friends over at SavvyCal upside.fm/savvycal, it has improved Eric and I’s scheduling relationship for the better. I guess that’s what an improved means. Improved means for the better,

Eric Hornung 57:22
Can you improve something to the worse?

Jay Clouse 57:24
I don’t think so.

Eric Hornung 57:25
Can you get something more negative and call it improvement.

Jay Clouse 57:28
Back to

Eric Hornung 57:28
I improved my I improved my losses. So I have a higher net operating loss going forward. Yeah, it’s possible.

Jay Clouse 57:35
It’s possible. Back to Patrick, the founder, spent a lot of time at New Relic in product management has a lot of great experience and skill built out of his product management and engineering background. And you see in the product, just how beautiful it is. And I know I know, we’re talking about a b2b model here. But at the end of the day, this is used by individuals, a lot of individuals who I think will probably have fairly high standards for what the experience looks like. And I truly, truly appreciate software that looks beautifully made. no small thing, but

Eric Hornung 58:14
Gorgeous.

Jay Clouse 58:15
It’s important.

Eric Hornung 58:16
Patrick’s a little different than the typical founder, we have an upside he is definitely much more in the true pure tech model. We talked a lot about open source in that model. In this interview, we talked about his time kind of hacking open source projects and codes. He’s also a third time founder. That’s a little different than the founder we tend to have on this show. We talk about starting on second base a lot on this show, simply Petrus kind of you know, round and second, maybe on his way to third. He’s built and exited two companies.

Jay Clouse 58:47
Which have I’m an investor that carries some weight, for sure. We haven’t talked about Portland, Oregon, on this show much Eric. We didn’t dig a whole lot into Portland in the interview, but wanted to call out new territory. We’re going to new ground.

Eric Hornung 59:00
We did talk to someone in Portland, Oregon. We talked to Periodic Edibles and off the record. I’ve been chatting here and there with the guys from Silicon Forest, which are building a media company focused on all of Oregon. So maybe we’ll have them on the show to talk more deeply about the Oregon ecosystem.

Jay Clouse 59:17
What does it mean when you say off the record, Boomer clearly on the record,

Eric Hornung 59:20
I said it off the record.

Jay Clouse 59:24
Well, dear listener, we’d love to hear what you think about Reclaim.AI. Give it a run. It’s free through 2021. As I said, I’m using it I enjoy it. It pairs well with your scheduling stack of SavvyCal or even Calendly if you go that way. But we’re SavvyCal people over here at Upside upside.fm/savvycal that’s SavvyCal. We’ll hear you think about this episode, what you think about Reclaim you can tweet at us @upsideFM or email us hello@upside.fm and we’ll talk to you next week. That’s all for this week. Thanks for listening. We’d love to hear what you think about this episode. So Tweet at us @upsideFM or email us Hello@upside,FM and let us know. You can learn more about us and browse our entire back catalogue of episodes at upside.fm. And if you love our show, please leave a review on Apple podcast that goes a long way in helping us bring high quality guests to the show.