Road Work Ahead

#10 - Henry Shapiro: Reclaim.ai, AI Scheduling & Time Management

• Waypost Studio | Sam Gerdt • Season 1 • Episode 10

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Welcome everybody, once again, to Road Work Ahead, a podcast that explores the unmapped future of business and technology. My name is Sam Gerdt, and today I'm talking to the co-founder of a company that has, without exaggeration, changed my life. I'm talking about Reclaim.ai, and my guest is Henry Shapiro.

Most people are familiar with the negative impact of meetings stacked on meetings or poor time management in the workplace. As our jobs get more complex, so does the task of managing an effective schedule.

Reclaim is an AI scheduling tool that does the work of time blocking for you. On top of this it gives you tools for managing meetings and establishing habits, guarding your time against the invading forces that so often steal your lunch hour or pull you away from deep, meaningful work.

Henry and his co-founder Patrick built Reclaim as a solution for teams to minimize disruptions and do more meaningful work, but Henry admits that no one expected such an overwhelmingly positive response to their product. Even in our interview I found it hard to contain my own enthusiasm.

Also, just a quick note: Henry says reCLAIM, I say REclaim . . . Potato, PoTAHto. Enjoy the interview! 

Sam Gerdt:

Welcome everybody once again to Road Work Ahead, a podcast that explores the unmapped future of business and technology. My name is Sam Gerdt, and today I'm talking to the co-founder of a company that has, without exaggeration, changed my life. I'm talking about Reclaim. ai, and my guest is Henry Shapiro. Most people are familiar with the negative impact of meetings, stacked on meetings or poor time management in the workplace. As our jobs get more complex, so does the task of managing an effective schedule. Reclaim is an AI scheduling tool that does the work of time blocking for you. On top of this, it gives you tools for managing meetings and establishing habits, guarding your time against the invading forces that so often steal your lunch hour or pull you away from deep and meaningful work.

Sam Gerdt:

Henry and his co-founder, Patrick, built Reclaim as a solution for teams to minimize disruptions and do more meaningful work, but Henry admits that no one expected such an overwhelmingly positive response to their product. Even in our interview, I found it hard to contain my own enthusiasm. Also, just a quick note Henry says Reclaim. I say Reclaim, potato Patato. Enjoy the interview, enry. I think I'm most interested to hear about those early conversations around Reclaim and how you intended to build this product. What was the problem that you saw and what were some of the solutions that you were thinking about at that time. Then let's get into how Reclaim actually came to be.

Henry Shapiro:

My co-founder and I, Patrick, we met one another at a company called New Relic where we were both product leaders. I think experienced firsthand this challenge that I think a lot of busy middle managers, middle to senior end, just lots of professionals experience inside of companies where, especially as companies get bigger, people's calendars get less and less aligned with what their actual priorities are and what the teams and companies priorities are, and more and more aligned with meetings. A lot of the important work that I think we were focused on was happening in our off hours, in the evenings and after work and on the weekends. I think we just felt that crunch and that strain and also were people who never had the benefit of executive assistance and wondered about whether there was a better way for us to help people with that problem. I'd say also, the other piece was just more at a kind of philosophical or maybe more conceptual level.

Henry Shapiro:

I think we were really intrigued by this idea that we have all these systems in our lives that are either partially or very intelligent, that help us to automate and orchestrate all kinds of infrastructure that helps us get through our days. The systems we use to manage our time have been using the same data, the same data model, the same metadata for like 30 years now. They basically all operate on this idea of you're free or you're busy In our world. We understand that there's a lot more nuance to how our time operates than that. Our belief was that if we could bring a lot more intelligence into the calendar and a lot more context about what mattered to people, we could make their calendars and their lives better, solve that first problem. But we could also start to unlock some really interesting challenges that just hadn't been solved around how people find time with each other.

Sam Gerdt:

You're probably looking at your bosses and seeing them with their personal assistants and you're saying I want that for me. I see the benefit that that would bring to me.

Henry Shapiro:

There were two processes that really stuck out to us, I would say. One was I noticed that all of the executives that we worked with you had EAs, had this weekly process, and sometimes multiple times a week, where they would sit down and their EA would say, hey, okay, so what are your priorities? They'd look at, they'd have the calendar pulled up, they'd have a task list or some kind of like scratch pad pulled up and they say what are your priorities? They would literally go through the calendar and try to go through this kind of process of striking things through on the calendar that were sort of like okay, that's lower priority, let's push that, let's punt that, let's delegate that.

Henry Shapiro:

The other thing they would do was if that executive were trying to get six people in a room that were all super busy in the same week, that EA's job was to go around to each of those folks and say, hey, it looks like you've got an event here that I'm pretty sure you could probably skip or delegate or you could maybe decline if you need to. Are you okay skipping this in service of getting this more important critical meeting scheduled? Those are really the two workflows that we thought about as like we could definitely automate that. Those are two things we could at least help people to do on their own.

Sam Gerdt:

You started out as an AI company.

Henry Shapiro:

We started out as an AI company. We started about four and a half years ago. I'd say we'll get into it, I'm sure a bit more. But our perspectives on AI I think we're very much like there's kind of this balance, I think, especially with calendaring, between sort of black box AI, where you don't necessarily know what the knobs and dials are doing under the covers, and this sort of more deterministic sort of rules based or business logic based AI. We really focused, I think, initially more on the latter, mainly because we felt like people are pretty new to this idea of putting a bot on their calendars or putting some kind of automation in their calendars, and people are. They want to have control over their calendars.

Sam Gerdt:

Ultimately, Well, absolutely. I think there are a few people that I know who have brought on EAs into their business owners. They're busy, they run their business and they don't have time for things like email. They don't have time for the lower level tasks. There's this huge mental hurdle that they have to get over in order to entrust something so personal as email or their calendar to someone else. Everyone I know who's done this. They talk about how the first month is just torture. It feels like it's never going to work. It feels very uncomfortable. There's all kinds of things that slip through the cracks After a month. There's just this switch that flips and all of a sudden now everything is running so much smoother than it ever has. It's super interesting to think about bringing the executive assistant down to lower levels. Most of us don't have access to that kind of resource, but through artificial intelligence, all of a sudden we're gaining access and it's unlocking all of these crazy things for us.

Sam Gerdt:

Hey, everybody, just a quick note here. We're about to get into some questions that talk about my own enthusiasm for reclaim as a tool to deal with some of the problems that come up for someone with ADHD. One thing that you may remember about me from a few episodes ago is we talked about how I struggle with ADHD and ASD. A big part of that struggle is time management. Before we get too far into it, I just wanted to make that clear.

Sam Gerdt:

The enthusiasm that I have for this product and the way Henry talks about this product, you'll see that there's a little bit of a difference there. I don't want my own comments to get in the way of Henry explaining what is truly a revolutionary product for all kinds of teams in all kinds of industries. One of the things with reclaim that I'm really curious about and I'm wondering how you talked about it in the early days and maybe even how you talk about it now. The tool is really helpful for people who struggle with time management. Specifically, I think about people with ADHD who listen to people like Cal Newport. They're familiar with concepts like time blocking and they want that so badly for themselves, but they're just terrible at doing it. I fall into that bucket of horrible time management and that's why reclaim is so valuable to me. You guys don't market yourself as a product for people who suck at time management or people who have ADHD or any of that, whereas you've got direct competitors who are doing that. They're saying we are an ADHD product.

Henry Shapiro:

I'm curious why that is yeah, I mean I would say there are a couple reasons. The first is maybe somewhat personal, although I guess maybe it's somewhat personal in the sense of I have a lot of people in my life, including my partner, who are pretty severely ADHD. Seen the ways in which it pretty uniquely affects all kinds of stuff Time, blindness and the feeling of getting over focused on tasks and then the whole day windows away. I don't feel great at some level and I think we have talked about it internally and I think we've said we don't really feel great about leveraging that to our advantage in a way I don't know quite how to put it except the feel that it just felt didn't feel right. Occasionally I would look at some of the posts from certain competitors where they were marketing themselves that way and I would look at comments and I could tell that there were a number of folks from the ADHD community that felt like they were being a little pander to. Perhaps I think that was part of it was just feeling like we love that people and we hear it from tons of users in our user base who tell us about the fact that the tool really, really uniquely helps with ADHD. There are even folks who, independently, have gone out and told that story for us, and we're actually really happy to have them be telling that story, because I think the other piece of it is like it's sort of like speaking to the problem when you don't yeah, when you don't have that connection to it, I think is really important. But I'd say more so than that, even just at a just pure business level, I guess Our belief is that this is like this is a very universal problem.

Henry Shapiro:

I think that it's a fair statement, although ADHD is a very unique sort of scenario. I would make the argument that we are all kind of living in this era of a ridiculous amount of distraction and a ridiculous amount of chaos. I mean these sort of externalities that people have to deal with on a day to day basis, as well as all of the just fatigue from all of the ways in which we're being constantly drawn in like 20 different directions. I think it's really hard for me to envision a person today who doesn't have some kind of like schedule, time management problem, and so I think our goal is actually to kind of bring more and more of the market and more and more of kind of the audience.

Henry Shapiro:

Right now I feel like just based on thousands and thousands of conversations with people over the past few years, there's kind of three segments to this market. There's 5% of the world that sort of is really really open to this idea of having, like an AI assistant or like a smarter calendar at their fingertips. There's like 15 to 20% of people who are even open to tools like Calendly that are like highly sort of structured they're basically just a scheduler that sits on top of Google and then the vast majority, I think, of people are like their maturity around calendars is super low, and so our goal is, I think, to bring as many people into that category of folks who understand that they have a problem and also understand that there are smarter solutions out there to it.

Sam Gerdt:

Yeah, it makes so much sense. What you're saying definitely resonates with what I know, and that is the majority of people either are on top of their calendar game, they're Type A, they're super organized, or it's just a mess. And what's really interesting is for a tool like Reclaim, which in some sense takes control of your scheduling. If you already have control of it, you end up hating the product because you feel like you're playing tug of war with something that you didn't ask. You're not ready to delegate those tasks. But for those of us who love the idea of time blocking, maybe we even have prioritized task lists, but we struggle with whether it's time blindness or bad task management Our schedules are constantly changing on us and we don't have the time to adapt and build out a new schedule. A tool like this is absolutely life-changing For me. It was life-changing. I've shown it to other people in our company. It's life-changing. I've shown it to other people who are friends and they're just.

Sam Gerdt:

Usually, as soon as I mention it and there are a few keywords, people will perk up Really and it's funny to see what they are. It integrates with Todoist and they're like really. Or if you get sidetracked or derailed and something doesn't get checked off. You don't have to go back and re-block your time, it just does it automatically. Really, you've got something that everybody wants, but not everybody's articulating it in the same way. It's so interesting, but because there's that disconnect between the people who really want it and the people who really don't want it, I've actually found it very difficult to incorporate this as an app for whole teams. Usually, whole teams aren't interested in using it because you have at least a couple of type A's on your team and they're like I don't want this managing my calendar. So it does seem to be something that's more supplemental to the tools that we're already using. Is that accurate? Is that something that you guys consider?

Henry Shapiro:

Well, I think that even within the type A group because I know definitely the group you're talking about and we have quite a few of those folks in our user base I would say People who are very on top of their calendars were on top of their calendars before they started using Reclaim, but they still recognize, just like any toilsome job, that there's a way in which automation still helps people who are type A. They may not view the product in the same way, they may focus on different types of features within it, but I think even something as simple as I have a personal calendar and I have a work calendar and I want to make sure that my work calendar gets blocked out for personal events that is an automation job. That's the first feature we ever built, and the reason we built that feature was because we felt like this is one of the most understandable and it's kind of one of the safest problems that we could start with. It's not asking people to change massive behaviors. It's literally like here's a job to be done. It's super annoying. Whether you're type A calendar management guru or not. It's just stupid. You have to go and create multiple events and keep them in sync. You're not a computer, and so I think those types of features, as well as things like habits, even for people who are like I block my lunch out every day. It's like cool.

Henry Shapiro:

Does reality ever get in the way of that? Do you ever find that your lunch gets overbooked? And then what do you do? All the other meeting time around that lunch event got overbooked, and so they kind of see the ways in which I think we lean into. Things like flexible availability, automatic rescheduling and those types of benefits also kind of, I think, can be helpful for those folks, even when they're fairly on top of their calendars already. So I think we went over a decent amount of those folks. But there's definitely, I think, also folks who, the same way that you mentioned that person who gets the EA, and maybe it's months before they actually really trust that person with their calendar there's also folks who I think to that earlier point about having to bring more folks into the fold who I think are just maybe not ready to get there yet and our hope is that over time enough people starting to use tools like these will sort of prompt them to move in that direction.

Sam Gerdt:

How does it affect the, I guess, the company culture, the vibe, whatever, I mean all the work that you do? When you hear the people say this product moved the needle in my life in a significant way, Was that expected? Did you expect to build a product that could do that?

Henry Shapiro:

No, I would not say so. It's really been. Honestly, it's still to this day and we get feedback like this on a weekly basis, sometimes daily basis, because we have a fairly active support process where people can chat with us and talk to us. That was a thing very early on. That was very important to us was, as we grew, continuing to have really personal and deep relationships with our users, to understand A how we're able to make the product better and let them know that there's a team behind this that's there to help and make their lives better.

Henry Shapiro:

Patrick and I worked on monitoring software for a very long time developer tools and you would hear things from those developers that were like oh, I really like XYZ tool, it's really nice, it's really cool, I use it in my work, but we've never worked on products.

Henry Shapiro:

I think that never worked on a product that has gotten to the types of things that we hear, like Even things as simple as hey, I ate lunch five days, you know a week for the last six months, and I like haven't done that since I started working professionally.

Henry Shapiro:

Or I just had like my most productive work week ever and I'm really excited for next week. Like it's still pretty mind blowing and we have a, you know, obviously a whole channel and space where we share that with the team and I think it's really for all of us like the thing that keeps us really motivated and it's very unique for us. I definitely was not something, I think, that we anticipated or expected and still, I think to this day, very much surprises us because I think it's we know and hope that the product is going to. You know, we took a lot of care to build the product and we invest a lot in trying to make our users' lives better, but the impact that you can have on people just by doing simple things for their schedule or, you know, complex but simple things for their schedule is pretty astonishing.

Sam Gerdt:

You're coming from a place where you're building tools for developers and you've had startups in that space. You've had products in that space. You're coming to this. It's much broader market. How has that changed just in generally? How's that changed your thinking and what are the challenges associated with switching like that?

Henry Shapiro:

Yeah, I mean, when we first started the business, our original intent we actually didn't even start with the idea of building a calendar product, believe it or not had nothing to do with calendars. Initially, our focus was the question we were asking was how would we make teams, product teams in particular more productive and what metrics would we look at and what things would we automate? And we, being DevTool people, started with like GitHub and Peter Newdy and all these things that we think of as like developer toil, showed it to a bunch of engineering leaders, showed it to a bunch of product leaders, and they all kind of said like meh, like that's cool. But, honestly, if you were to ask me why I'm struggling to be productive, it's because I'm in like eight hours of meetings a day and there's no time for me to get worked on. There's no time for me to, like, spend time with the team or work on design sessions or do the things that I know are really important, and then I'm drowning in email and notifications and all the rest of it. And so that's what led us to the calendar, as we sort of said like okay, that's so, that's where that data lives and that's where that's where all the action is happening, and so we.

Henry Shapiro:

Originally our theory was this is going to be really useful for product teams. You put something out into the world and it turns out what we were really building, I think, was this more kind of flexible platform that could be utilized across a whole bunch of different use cases, and before we knew it, we had students and consultants and people in sales and people in engineering, and executive leaders and frontline managers and senior ICs, and it's a universal problem. So I think, in some ways, I think our emphasis has had to be on continuing to build a platform, and that is also. That is a. It's a, it's a benefit and it's also, I think, it has a challenge associated with it.

Henry Shapiro:

If we were working towards like a single optimization, if we were like, hey, we're a product that really embraces eat the frog, or we're a product that really embraces Pomodoro, we could build all of our workflows around that, but we would very narrowly focus ourself on the group of people who care about that one type of optimization, and we'd have to have this like really strong opinion that that's it.

Henry Shapiro:

We have a strong opinion that your calendar should be aligned to your priorities, but then we try to give you a set of flexible tools that can help align it to that and schedule around that. And so we have to kind of continue building a platform, I think, in order to aid as many types of people as possible. And then from a go to market standpoint, I think the you know challenge, and I'd say the way we've kind of weathered it is really by focusing our efforts on the two groups that have kind of emerged as our sort of top two kind of enterprise use cases. One is sales and specifically pre sales, and the other is engineering. Those two groups, you know, together make up about 60 ish percent of our user base, so it's a relatively strong concentration. But then there's of course this long tail of folks who get value out of the product for all sorts of different reasons.

Sam Gerdt:

There's like you mentioned. There's that there's that subset of people, that 40%, who are using it as part of either a personal or a small team's tech stack. What's your vision, then, for the product? Does it continue to like fit into a tech stack, or does it become its own platform?

Henry Shapiro:

Well, first I'd say you know, our belief has always been that enterprises might buy software. But people use software.

Henry Shapiro:

And so we've always built and I think we'll always build with the individual in mind. I, my belief, is to your question about. We get asked this question all the time for users like hey, are you going to replace Asana someday? Are you going to replace, you know, Todoist someday? And we like to think about it in terms of, like, we're a small team. We have, you know, just like any small team. You know only so much we can focus on and do well at a time, and so we really think about, like, what's the biggest set of like unsolved kind of green field problems where we think we could add value and differentiation? And for us it always comes back to scheduling.

Sam Gerdt:

Do you guys know what a green field problem is? Because I didn't. I had to look it up. A green field problem is a problem where there is very little or no work that you can build upon. So in this case, Henry is talking about scheduling being a green field problem, and the idea is that the available resources that you have to draw from is so limited that you're essentially starting from scratch.

Henry Shapiro:

Project management, like there's lots of interesting problems in project management, but there's also some some pretty well worn tracks out there and there's a lot of work that would go into us being a true project management platform or being a even the subset of like meeting agenda. You know products that are out there. There's a lot of work and workflow that goes into those things. It's very people are always like we just throw projects in there and put a con bonboard in, you're done, and it's like, yeah, okay, until there's like a 300, I've seen Jira's feature request board, so I think I think for us it's really going to be about how can we be the smartest scheduling engine first and foremost period, and our belief is like these big databases we use, these project management systems we use, that are basically just collection of work, like they help you capture the work.

Henry Shapiro:

They don't help you get the work done and we would be like we would like to be the product that helps you get the work done. Does that, on some timeline, lead us to a place where, because we're the downstream platform that helps you get the work done, we maybe start to dip our toe into project management? Like, sure, potentially, but I think there's so many interesting problems for us to work on around meeting and sort of product productivity scheduling use cases that I think we feel like it's a that's where our focus is going to be for the foreseeable future. What?

Sam Gerdt:

sold me on reclaim was its integration with Todoist. Not, when I. When I first started using the product, I had a zero interest in inputting tasks directly into reclaim none. I was already very pleased with Todoist and the way that reclaim seamlessly integrated with Todoist was the big seller. There was no weird setup that had to happen, it was just I could put it into Todoist and it would be on my calendar where it needed to be. That frictionless integration was what made your product to me so valuable. Is that something that you guys continue to look at and work on? What should we be integrating with?

Henry Shapiro:

Yeah, absolutely. I would say the next kind of frontier for us is likely going to be CRM. There are all sorts of interesting workflows that come out of those products. I mean, those products have tasks in them as well, which is something that you know. If we, if you've never worked in sales or or or haven't known people who do, you almost wouldn't know that or like think like well, what do salespeople use for project management? They use Salesforce or HubSpot. That's where they keep all their tasks and projects and they've got like.

Henry Shapiro:

Gantt views and project management views the same as anyone else, and and so there's there's tasks that come out of those systems that are really interesting, and then there's also other types of scheduling workflows that are really kind of fascinating to us. We've been making a lot of progress over the past few months and just recently put into private beta this kind of new prioritization system that we've been working on for a while. But one of the things that we've been looking at is how to be basically how to use that priority to send more or less availability to people based on how important the meeting is. And so there's all these interesting use cases that flow out of that around customer and sort of you know, customer facing types of meetings, where urgent meetings kind of get higher priority and higher billing and get more availability and lower priority, you know, sort of opportunities or things that are just further out on the calendar, just not necessary to happen this week.

Henry Shapiro:

Those get a little less availability, and so there's just all these interesting ways. I think that we could start kind of digging into CRM. So probably CRM is really the next big stage for us.

Sam Gerdt:

Hey everybody, just a quick note that I'm about to derail this interview once again with my own enthusiasm for the product. Henry just got done, saying a lot of very good things and my response was essentially yeah, but here's what I want from it. So, anyway, I hope you'll indulge me and forgive me just this once I'll try not to do it again. Keeping in mind that whole personal assistant thing, I would love to see more integration with those stacks that people are using to kind of build that personal assistant out in their own lives. Sales people do have HubSpot and Salesforce and we all have some form of task management, project management, but we also have email integrations that we want to see I would love to see. One of the big things that I always look for in products today is some sort of natural language UI. Yeah, ever since Chad GPT kind of hit the scene and blew up, natural language UI is just it's one of my favorite things to see in a product. So, yeah, keeping it in that direction too would be like I'm rooting for you guys to keep that.

Sam Gerdt:

I do want to talk a little bit about the brand, because this is something that's come up a lot in the interviews that I.

Sam Gerdt:

This podcast tends to focus on technologies, but it's always fascinating to see how brand comes into it. One of the things that we want to do with these interviews is point people to where they should be thinking or what they should be doing in the face of disruptive technology, and the thing I keep coming back to over and over again is like I really feel like the most important thing a person can do right now is focus on their brand. It's just give the brand the development and the love that it needs to become a conveyor of the emotion of the company, of the value of the company. And so I'm really curious to talk to you a little bit about how you built a brand in the AI space, which is kind of a. It's a newer space, it's a more competitive space, a lot of new companies coming in and it's a startup. So there's always that you're trying to push product, but you're also needing a brand in order to push product. So I'd love to hear a little bit more about the origins of the Reclaim brand.

Henry Shapiro:

Yeah, I mean I think from the very beginning there were kind of a few kind of tenants. We really looked at one of our favorite brands from a just corporate branding and, I would say, founder led branding standpoint was actually Atlassian. That's probably one of the biggest inspirations for us. Patrick, way back in the day, was an early. He actually built the original Gira workflow editor with Mike and Scott and co-authored a couple books with them in the Java realm, and so he had very early exposure to Atlassian. I think was very kind of inspired by their kind of approach.

Henry Shapiro:

And I'd say that the things that really stuck out to us about their brand that we wanted to kind of emulate were kind of transparent. No BS Like that was a really important piece to us. We didn't want to sell fluff, we didn't want to overmarket our solution to the point of sort of losing the context of what it really did. And the transparency also manifested itself not just in terms of, like what we put on our website, but how do we write about what we do, how do we support customers, how do we kind of talk about the problems that we're trying to solve, and so I think that was kind of at the core of it was like we really wanted to be a brand that came across as highly transparent, obviously trusted, but sort of transparent and no BS. I think there's a kind of humility. I think also that both Patrick and I tend to have especially, I'd say, in the realm of founders, where that is not always in high supply and I would say that we really wanted that to come through as well. I mean, I think sort of a sense that there's a sort of small, scrappy, hardworking group of people behind this. And even as the company grows, I think we still want people to have that impression that they're kind of, they're doing business with and working with a team that responds quickly, is pretty agile, changes direction when they need to, but isn't like thrashing the product or thrashing the direction, has a vision of where they want to go.

Henry Shapiro:

And I think the last one was kind of like playful fun, like we wanted to be a brand that people didn't view of, like there were so many products coming out at the time that we're all going after the superhuman interface and superhuman is an awesome product, don't get me wrong but it was all everyone trying to build like black and white apple style kind of branding very kind of slick, think, you know brushed metal branding, but minus the skeu-morphics and we were very like no, we kind of want to be a little like fun and colorful and we want people to feel like this is a problem that isn't about being overly kind of rigid and, you know, sort of gray.

Henry Shapiro:

We wanted people to feel like this is a problem they can have fun with and a problem that actually they can sort of dig into and feel like good about. And that was part of where, like, the onboarding came from and a lot of the colors and animations and brands me a lot of that stuff really kind of came from our feeling of like we want this to be a fun brand too, because we also want it to be a fun company for us.

Sam Gerdt:

You can kind of tell when a company is trying to bring another brand into their own. I think about, like you know, open AI has a very distinct look their website, their products, their all their design, very distinct look, and I see that look more and more incorporated into other AI startups who are kind of trying to latch on and convey that feeling. When I look at Reclaim, I don't really see any of that and in interacting with the brand you're right, it does come across as being a very scrappy team, like I've never had any problem talking with people at the company, like whether it's through the Slack community or, you know, on social media, it seems like there's always somebody who's available. I think I've even posted about Reclaim in the past and gained followers from the company through those posts. Yeah, like your team seems genuinely interested in just being being people connecting with people.

Sam Gerdt:

There's there's so much out there. How do you differentiate yourself from the next guy? Is it just? Is it just chasing that human connection? Is it being humble or is there like I mean, what would be the Reclaim playbook for saying we don't want to look like the average AI company. We don't want to get lost in that noise?

Henry Shapiro:

You know I'd say generally speaking, and then I'll speak to the AI piece. Generally speaking, I would say that our it kind of comes from. We built this culture, I think, and Patrick and I still to this day we both answer support tickets. Like we spend time in support. We spend less time than we did a year ago, but if you look at the stats on the board, like we probably still have more support tickets closed than anyone else in the company, because in the early days that's what we did was was we talked to every user that came into the system that would write into support, would talk to either Patrick or myself, and so part of it, I think, is staying really close not just to the problems like that you're hearing about in the ether, because there's lots of interesting problems out there that get discussed in the world and then there's also a lot of like echo chamber stuff that gets discussed and people forget about how complex and nuanced these problems really are. Like they're not. As soon as you pull a thread on anything calendar related and think of a space where, in addition to it being a very complex workflow, the margin for error is incredibly low. Like you, cannot you mess up one event on the calendar and, understandably, someone loses a lot of trust quickly. And so I'd say it really comes from listening to our users and hearing the good things that are happening, the bad things that are happening, the way our brand showed up to them, the way that they interpreted something that we showed to them in the self-serve process, like we listen to those things and we try to tweak them and make them better and make them better and make them better.

Henry Shapiro:

And there is no, as far as I know, there is no magic lever to it. It is just like keep, keep, poking on it and poking on it and poking on it until it's better. And there's going to be these big moments, you know, for us as a company, these big releases and big. We have big ideas of things we want to do. But it's those, it's all those little tweaks and all those little interactions with people that I think compound into something really great. And there it's also the reason that I think we have people on the team who also internalize that for themselves, because I think they recognize that that's that's part of the fun of working at Reclaim is like you build something. It gets out to customers within seconds. You have hundreds of thousands of people using it and they're all giving you feedback and the iteration cycle can be really fast and it's like that's. That's fun for developers too. It's fun for people on the team who build anything here.

Sam Gerdt:

Did you hear it? Did you hear it? I heard it. We've talked about this before. You don't just add a technology because it's there to add. You add a technology because it helps a person. You add a technology because it helps you fill that brand purpose. It helps you accomplish your overarching goal, which should be rooted in the good of humanity.

Henry Shapiro:

On the AI front, I think there's a little bit of a solution looking for a problem in some cases with certain types of you know applications of this stuff, like people who are just kind of like slap a slap a generative AI or slap a GPT on it. And so I think, like the critical thing for us is always thinking about so GPT, just as one practical example is really good at doing things like you know, taking a bunch of event data or a bunch of calendar data and trying to understand what that date, what that text is saying, you know what, what's the priority of this event, who, you know which of these events might be flexible or might be movable, like it's actually pretty good at doing that. It's actually alarmingly bad at doing normal, just basic scheduling. It has no real, like some of the examples that are provided in some of the, the white papers we've read through and some of the tests that we've done, it's it's not very good at doing like bin packing math. Yeah, the good thing is we're really good at that.

Henry Shapiro:

And so I think the the opportunity, I think what I would be looking out for as far as like differentiating ourselves, is really thinking about those interfaces as primarily great engines and great ingestion sort of points for calendar, event data, email data, slack data, all sorts of stuff that gives us context, and that context is what we want to use to drive better scheduling on the calendar. Because, again, our, our contention is that most of the time, scheduling is not a math problem, it's a negotiation problem, and so that's really how we think about splitting the market. I'm very wary of companies that are pitching the executive assistant thing and where it doesn't appear that they've done a whole lot more than, like, basically just put a wrapper around GPT, yeah, and I think that's where, like, you have to look at a company that has been sort of thinking about this also from a business logic, core services standpoint, to kind of drive those workflows.

Sam Gerdt:

So two weeks after this interview was recorded, open AI announced a new product that essentially allows you to take your own training data and train chat GPT on that data. It's very easy to do you don't even need to be a developer to do it. But what this means is that all those companies who built a custom interface for what was essentially chat GPT those companies are all now instantly irrelevant and we're going to see a lot of them going bye bye really soon. In my own pursuit for that AI executive assistant, it's been very simple to realize that there's no one solution, especially something like GPT. But you see glimmers in all of these little things and you recognize okay, well, as long as the integrations hold together, I'm going to get a little bit further with a new tool here, a new tool there. That was what was so very exciting about Reclaim the idea that it just worked with the few other apps that I was already using. I don't know why that's so unusual, but as somebody who is working on text acts for businesses all the time, I can tell you it's incredibly unusual to just plug two pieces together and have it just work the way you want it to. When I see these pieces of AI appearing here and there. What I'm rooting for, what I want to see is I want to see people see the good part of it. I want to see developers see the good part of it and say, well, we could use that to make our product a little bit better, rather than looking at it as a standalone product.

Sam Gerdt:

And I think there's, like you said, there's been too much taking it and making it a standalone product with a new brand slapped on top of it. That's why I mentioned earlier GPT is a good UI. I love chat GPT as a UI because I don't need my mouse and keyboard anymore. I can just talk to my computer. That's the big reason why I've always loved Todoist is because they give you a single text box and then they give you just it's really easy to ingest a complicated, complex task with one text box. So all of those little things coming together being plugged in together to make that that personal assistant we're getting. We're getting ever closer to that, just little by little. I'm really hoping that we can see products like Reclaim, take, take the good from these AI technologies that are coming out, apply them thoughtfully and and just very modestly, very humbly improved to the point to where you're saying you know I wouldn't use Reclaim for everything, but I would certainly never lose it, like I would certainly keep it plugged in.

Henry Shapiro:

There's all these actions that you take inside of our product today. You know you're familiar with them because you use tasks. You know, if you want to say I want to kind of change the order of this task and reschedule this thing and start this thing and like right now, that's a whole bunch of like button clicks and so, like, some of the most immediate use cases for us are literally to your point about user interface is just like just give people the ability to express what would be a fairly complex instruction set and let Reclaim sort of work it out through. You know, touching all the. We already have all the services that drive all the stuff. It's it's just a matter of chaining all together.

Henry Shapiro:

You know the actions based on a prompt. And so I think, like our first, our first kind of interest is around like how can we reduce just friction in using the product? And that's really, I think, where we see the big opportunity around GPT right now is like there's certainly a intelligence component to it, like we could learn more about the calendar, we could do less, put less manual tagging effort on the user, and that's also part and parcel of the equation. But I think there's also just these workflows, whether they're meeting scheduling or task scheduling or whatever, where you're trying to tell Reclaim to do like 15 things and rather than you having to go and individually tell it to do 15 things, just tell it to do one thing and or several things within one prompt and let us let us go sort it out and preview it for you. You know the sort of idea of a I need to get time with these six people by the end of the week and then a bot that is sort of going around and querying individuals, you know, sort of automatically, and they're all having conversations to the side, and then that thing coming back to you and saying like here's what I found and here's, you know, here's the re, here's the kind of recon that I've done.

Henry Shapiro:

There's something really magical about that and it in some ways, it's kind of like. I think a really good way of thinking about some of these kind of problems is is like, does this feel? Does this feel human? Like does this feel like a thing that I was already doing? It's just a little faster, a little smarter and significantly cheaper and in both in terms of time and actual dollars, to to pull off. And that workflow I just described is one that I mean. That's what people are doing today. They're just doing it with each other or, if they're lucky enough to have a full time executive assistant, they're doing it with that person sort of in the mix in like a slide room or an email thread.

Sam Gerdt:

As part of a small company, with a small team, we still we're not even in a big space and we still struggle with that to coordinate, say. Say that you want to get three people in a room together at the same time. It's it's becoming more difficult to to accomplish that, as you know, as teams grow, as they get more busy, especially if you're trying to pull in people from maybe different disciplines, different departments. So, yeah, it's really interesting to think about how an artificial intelligence can take that legwork and and and, silently, just maybe maybe it's not even like it's accomplishing it for you, but it's presenting you with options. Who are you listening to in, in kind of in this space, as you as you're, as you're looking out there? Who are you taking inspiration from?

Henry Shapiro:

I think that the you know there are definitely some people in this space who I think of as really smart in and around scheduling as it relates. So there's a company called Calcom. I probably shouldn't promote them because technically there may be a competitor, but they have a founder this guy, pierre Richardson, who's a bit of a curmudgeon but also like really smart on scheduling and just really gets like this space in some pretty fundamental ways. We're in very different parts of the market. He's looking at this kind of like open source in you know calendar as infrastructure opportunity and I think we're thinking a lot more kind of like we're integrating with the services that enterprises use, like Google and Outlook, and trying to kind of build a business around that.

Henry Shapiro:

But certainly like that, you know, in the scheduling space specifically, he's a really interesting voice and really just like appreciate the work that that they're doing there. Really interesting company too. And then you know, I think we, we we listen to there's a couple of folks on the kind of productivity front, one of whom is actually an investor of ours, this guy, john Zeratsky, and which they started a small fund called Character. It's based out of Milwaukee and they run these really amazing like design sprints for their companies and also are just. He wrote a book called Make Time a Long Time ago and was one of our earliest investors, actually as an angel. We connected with him because he sent out a newsletter that we subscribed to and we poked him and said, hey, we're building something that's kind of like what you talk about, except we're trying to build it into software.

Sam Gerdt:

If you've never heard of the book Make Time by Jake Knapp and John Zeratsky, can I just say go read it. Let me read you something from their website. Make Time is not about crushing your to-do list, optimizing every hour or maximizing personal productivity. It's about rethinking the defaults of constant busyness and distraction so you can focus on what matters to you every day. The book is like five years old and it is still so good. This is exactly the kind of mindset that we need in tech. This is the kind of mindset that we need in work. It is exactly what I needed to hear several years ago when I read it for the first time. I cannot recommend it enough. You guys need to go to the website maketimeblog. You're going to find a lot more about them there. Go check it out.

Henry Shapiro:

He's just got a ton of really awesome perspectives on like he's very much. He and his partner, Eli, are both just like really important, like kind of mentors for it Not mentors, advisors for us as we think about the company, but also advisors for us as we think about product concepts and how they affect different types of users. And then I'd say, first and foremost it's kind of cheesy, but our customers, our users, that's who I would say we take the most inspiration from and we listen to the most, because they're the people who I think are best positioned to kind of influence our thinking and they're closest to the metal. I mean, there's no one closer to the metal than the person who's using your product, especially the person who's using your product completely unassisted by you and running into all sorts of oddities and problems and things that you can make better for them.

Sam Gerdt:

So for my part, this has been a bit of a personal journey for me, this whole idea of kind of it's almost like you're facing your demons. You have to figure out, like, how you work and how to optimize because there is so much distraction coming in. So on that front, I think of that book, john and Jake, and that book and as a designer I started as a designer I read Sprint and they've done a lot of excellent work. But then also, like Cal Newport, the way he talks about productivity has been particularly helpful and a lot of times it's really frustrating. A lot of times you read these guys and they're dead on, but then you go to execute. Like Cal Newport, he's always like you just got a time block and then that's the extent of it, like he'll show you how to do it, but then you go to actually do it and it's like well, I can't.

Sam Gerdt:

My brain stops there, and that's why you look at reclaim and it's like, well, let me do that for you. And it does it really well. That's the other thing that just I'm always. I'm a little bit amazed constantly at how well it works. I've kind of grown accustomed to it now, but like it's always fun just to see how well it works. Sometimes I go into my day and I'm just like is it going to know that I really need to do that thing for most of the day, because I know I gave it a lot. Is it really going to know? And sure enough it knows. And even when it misses and maybe it puts something else there, I always find it's like, yeah, I guess I should do that thing too, though.

Henry Shapiro:

Like.

Sam Gerdt:

I'm zeroed in on something and it's saying yeah, but you really ought to give 15 minutes to that other thing over there. So you know, I find myself arguing with it sometimes, but then I have to admit the feet usually because it's like I can't argue with a math based entity.

Henry Shapiro:

Well, some days you'll be able to.

Sam Gerdt:

Yeah, but I'll still be wrong.

Henry Shapiro:

Yeah, you know, I think one of the things we loved about Make Time and about John's book was just the degree to which I think you know he's somebody who has been in big, busy software companies with crazy, hectic, terrible schedules and I think his emphasis on simplicity and sort of like pick your, pick your top, like pick just theme your day around, like the top couple things you need to get done. It's super powerful and it's one of those like yeah, no duh things, but people really overengineer this stuff. And that was what really resonated for us was this idea that it was like look it's, it's really complex, it's very nuanced and hard. It's not to say this is easy, but it really is to some extent as easy as saying like ground yourself in the most important thing and many other things will flow from that and don't get too caught up in, like the mechanics of it and where it gets challenging. And I think why you know oftentimes you know the the plan doesn't survive.

Henry Shapiro:

Contact with the enemy, so to speak, is you're in a vacuum with a calendar that has no inbound commitments and no inbound conflicts and no inbound requests for time. Time blocking would work perfectly. There probably be no need for something like reclaimed. Besides the pain of moving things around, it's the it's this tension that we're all facing between. Ok, I need to be available, but not too available, so that people can find time with me and they don't slack me all the time. So my calendar isn't completely full, but I need to have like a little bit of leeway to get my work done. I need the ability to kind of be agile when things change and have things move and kind of truncate and shift around as needed, and I need a way to kind of express when my own priorities change. And doing all of that yourself on your own calendar is really painful in a busy organization.

Henry Shapiro:

I think that's what we really appreciated about John's perspective was it was coming from somebody who really had lived that life and, I think, understood that there wasn't. There was this real set of tensions between what people know they should be doing and what happens in reality when they when they actually get into it.

Sam Gerdt:

Well, it was. It was a concept, though, that saw people as being human and, and you know, human in their capabilities, but also human in the sense that there's more stuff that they want to do than just work. And so the idea of embracing all of the things that you love and asking that question well, well, like what, what do you want to do today? You know they. The book is made up of. I could talk about the book for a long time, but the book is made up of. You know 100 or so strategies. You know little little tactics that you can use, and you're not expected to use all of them. You're expected to mix and match, because everybody's different.

Sam Gerdt:

Yeah, but one of the tactics was, you know, ditch the to do list and create a might do list. You know, yeah, yeah, it's, this is my might do list. This is a list of all the things that eventually have to get done higher and lower priorities, but this is not my overlord. Yeah, and I feel like that's. I feel like reclaim has has done a good job of merging the to do list with the idea of you're a person, who, who is going to just do some work today, and we want to chip away it as much of it as we can, but obviously it can't all get done today and we're not going to make it your overlord.

Sam Gerdt:

It's such a comfortable place to be and I feel like it's really nice to find a tech company an AI company, you know, a scheduling company even who is saying let's just treat people as unique people and give them a tool that takes friction away from them having a really good day with whatever they're facing. It's such a powerful purpose. You know, remind me, do you guys have, do you guys have, like a codified brand purpose? I don't know if we've ever sat.

Henry Shapiro:

I mean, I think one of the things that we, you know, talked about for a long time, was a more perfect work week. You know, I think we probably haven't spent as much time as we probably should around establishing like a snappy snappy brand purpose statement. It's sort of evolved and changed, I would say, over time. I can't recommend enough the platform. I continue to talk about it with other people.

Sam Gerdt:

It's. It's an excellent tool. I'm really honored that you would be willing to come on here and talk with me about it. This is it's a little bit of a. It's a little bit of a, I don't know. This was a special interview for me. This was an awesome, awesome interview.

Henry Shapiro:

And I really appreciated the opportunity to come on and really truly appreciate the investment that you've made in in our product means a lot, and and the degree to which you've incorporated it into your life and the degree to which it's impacted you is, as I said early on here, it's still something that, to this day, is it makes a huge difference for us. It's it's you know why we get up in the morning, and so I thank you for for taking the time and for having me on. Yeah, well.

Sam Gerdt:

I mean, I can't again. I can't express the change that you know. It saves so much time and it turns planning my day, something that I dread, to something that just doesn't even it's it's, it's fricking crazy. It just doesn't even it's it's, it's frictionless. So yeah, it's my pleasure, absolutely my pleasure. Thank you, sam, appreciate it.