Henry Shapiro and Patrick Lightbody on Revolutionizing Productivity with Reclaim.ai

#66. In this special episode of The meez Podcast, host Josh Sharkey welcomes Patrick Lightbody and Henry Shapiro, founders of the revolutionary app, Reclaim.ai. Unlike the typical focus on the restaurant and hospitality industry, this episode dives into the realm of digital hospitality, exploring how Reclaim exemplifies excellence in this space.

Patrick and Henry share insights into the creation and impact of Reclaim, an app designed to optimize work habits by intelligently managing calendar events. They discuss the transformative power of Reclaim, explaining how it helps users prioritize essential activities like strategy sessions and exercise, ensuring a balanced and productive schedule.

Listeners will gain valuable knowledge about product development as Patrick and Henry discuss their approach to building Reclaim, including how they prioritize features, gather and synthesize customer feedback, and stay grounded while planning for the future. This episode offers a unique perspective on technology and product innovation, providing lessons that extend beyond the restaurant industry.

Tune in to learn from Patrick and Henry's experiences and discover how principles of great product development can be applied to any field.

Where to find Henry Shapiro:

• LinkedIn

Where to find Patrick Lightbody:

• LinkedIn

Where to find host Josh Sharkey:

• Instagram
• LinkedIn
• TikTok
• Twitter

In this episode, we cover:

(06:05): Why Reclaim was built
(13:01): Reclaim.ai 101
(22:19): Henry and Patrick's thoughts on alternative checklists & tasks
(29:23): What to think about when building great product
(51:13): Problems that Reclaim.ai aspires to fix
(1:02:14): Reclaim's future vision

Transcript

[00:00:00] Josh Sharkey: 

You're listening to season two of The meez Podcast. I'm your host, Josh Sharkey, the founder and CEO of meez, a culinary operating system for food professionals. On the show, we're going to talk to high performers in the food business, everything from chefs to CEOs, technologists, writers, investors, and more about how they innovate.

[00:00:19] 

And how they consistently execute at a high level, day after day. And I would really love it if you could drop us a 5 star review. Anywhere that you listen to your podcast. That could be Apple, that could be Spotify, it could be Google. I'm not picky. Anywhere works. But I really appreciate the support. And as always, I hope you enjoy the show.

[00:00:45] 

Alright, ladies and gentlemen. This is well, this is a special episode, I would say, in that it's untraditional in that the guests today have basically nothing to do with the restaurant industry or the hospitality industry other than, I would say, that what they've built totally exemplifies great hospitality, at least in the digital realm.

[00:01:07] 

The guests today are Patrick Lightbody and Henry Shapiro, and they are the founders of This app that if you've been listening to the podcast or maybe other podcasts that I've been on, you've probably heard me talk a lot about this app that I use called Reclaim, and it has really changed the way that I work.

[00:01:24] 

in a really positive way. It allows you to create all these habits within your calendar that get moved around. So you make sure no matter what, you always have the time for things like strategy or, you know, exercise or all the things that are not booking a meeting on your specific calendar. And still a lot of people to book your book time on your calendar and everything gets prioritized.

[00:01:46] 

I'm doing probably a terrible job of explaining how incredible this app is, but we dig really deep into it. I have to tell you, it is one of the best applications that I've ever used that has a significantly big impact on the way that I work and the way that I just generally run my life. We are going to talk a lot about what it's like to build product and how to do it.

[00:02:06] 

Patrick and Henry think about prioritizing what to build, the heuristics that they use to think about what features to build, how they synthesize the feedback of their customers. Generally speaking, how they sort of think about the future of what they're building, but still stay very grounded. And of course the history of how they got to where they got to with this product generally and with their careers.

[00:02:27] 

And it was for me an incredible learning experience of how folks outside of the restaurant space approach technology. And I learned a lot. I think you will too. And I know it's not specifically about food, restaurants, or hospitality, but I think everybody can learn a lot about how to think about building great product, whatever type of product that you're building, how to have the right sort of first principles to make decisions and how to continually iterate and get better.

[00:02:53] 

So, thanks Patrick and Henry for taking the time to come on board. I definitely cold emailed them and asked them to come on. So I was really appreciative of that. And as always, I hope that you enjoy the show as much as I did.

[00:03:12] 

Man, I'm so freaking excited to have you guys here. I don't know if you know this, but I talk about you guys all the time. So this is kind of like a fan boy episode. I have to be really careful. One thing is like, you're probably wondering like, why am I on a, hospitality, you know, I mean, we are a tech company, but like, you know, I'm a chef, I was a restaurant in most of my life and, and, and most of the folks that listen are in the restaurant business.

[00:03:35] 

And you're probably why you want to, why am I in a restaurant podcast? But I'm just obsessed with your product. So I'm going to try to not have my like tech hat on. To just ask you guys a million questions about technical things, because I'm just enamored, but I, at least in 10 episodes, I have mentioned your product.

[00:03:54] 

I also just like posted something about it on LinkedIn a while back, and I just love it. I don't tell you why I love it. And then we can get into you guys. Cause you know, that's obviously what's, what's most important, but I've been looking for this product forever. You, you know, and I can see, I think I have a sense of like the trajectory of what you're building, but I'm a big believer that doesn't matter how big of a, of a list of things you have to do, or even if you have like an asana board and it's organized really, really well of like, you know, a backlog and in progress, there's only so many hours in a day.

[00:04:26] 

And this becomes even more and more like a parent when you start having, obviously, if you're an entrepreneur, if you're a CEO, if you have like a, you know, a job that's very busy, and then you have, I have two kids, a wife, and all that other, other stuff going on where like time gets crunched and crunched and crunched.

[00:04:38] 

And it's like, it, it's irrelevant how, what your list looks like, unless it's correlated to how many hours you have in a day and when that's going to get plugged into, you know, to your calendar on top of that, I mean, I have an assistant that helps me with my calendar because my calendar is like, I've always been maniacal about measuring, The time I spend on each thing and looking back over time and seeing how much I spend on this versus that and what's driving energy or what's driving output, which is obviously a whole other thing that I don't have to worry about now, but I have these blocks of time that are just like, I, I know I needed to spend X amount of time on strategy.

[00:05:15] 

And I know I need to spend X amount of time on, you know, just team shutouts, where I'll just spend like 30 minutes where I just want to work on like things for my team, or spend time on product ideation and things, independent of like all the things I have to do, just like I block those times. And before it was, it was in my calendar.

[00:05:30] 

And then I would have to, like, delete that event, or move it around, and it was a mess. And then you guys built, we'll talk about the product, but you solved that problem for me. And, man, it's just like a game changer. So, first of all, thank you. It's, it's awesome. And the new, I, I actually just started using the tasks as well, which is killer.

[00:05:49] 

I don't know why I didn't start using that earlier, but. We'll get into that more. I just wanted to give a quick, you know, like recap of like why you're on, because I just really love the product and I wanted to totally meet you guys. Patrick, I already met with you because of the refactoring, but I'll, we'll get into that.

[00:06:02] 

But why did you guys build this product? 

[00:06:05] Patrick Lightbody: 

Yeah, first of all, can I just say, you know, if for any reason, you know, The food business does not work out, you know, you're always welcome. Just come and join our sales team or our marketing team. Uh, cause, uh, I was ready to buy this product they were describing. So I'm all, I'm all in.

[00:06:19] 

I'm glad it's, uh, I'm glad it's working for you. And you did a great job, uh, describing kind of some of the intent that we were, we were going for when we built this. Yeah. Henry, do you want to, do you want to kind of tell a little more of our origin story and how we met and why the hell we did this thing?

[00:06:34] Henry Shapiro: 

Yeah. Yeah. I mean, well, and yeah, echoing Patrick, thank you for, for all the kind words about the product and it's, uh, it's, it's always really cool to meet people who are. using it in their daily lives and to hear about kind of the impact it's having. And that's, you know, that's ultimately what kind of gets us up in the morning and keeps us going because startups are hard, as you know.

[00:06:52] 

Yeah. I mean, honestly, a big, a big driver for us. I mean, there's really kind of two, two parts to our origin story. I'd say one was Patrick and I met when we were both product managers at a company called new relic, which interestingly, our background has nothing to do with productivity tools or scheduling or calendars.

[00:07:11] 

Like this was not our. Space. So to speak, it's not like our DNA. If you will. We were actually very entrenched in the world of like DevOps and monitoring and observability. And I'll come back to that because I think that's actually part of why we ended up building something that we think is pretty unique in the market.

[00:07:28] 

But we kind of started with two main problems. I mean, one was Why the hell is it so hard for us as busy middle managers to get time for the stuff that we know is important every week? Like, why is it that every single week it feels like our calendar is like a debt we have to pay down every week so that we can do our real work instead of a thing that really actually should be a pretty perfect encapsulation of what we're supposed to be working on.

[00:07:53] 

And that was kind of the personal problem or the individual problem, which I think you're kind of doing a good job of capturing. And then I say the the broader issue that I think got us really excited about it as a business was thinking about the impact this has on teams and companies and organizations where the calendars like this totally ignored.

[00:08:13] 

Like people have project management systems, as you said, they have their Trello boards, they've got their Asana boards, they've got. All these databases of like stuff we're all supposed to go do and then the calendar is actually where all this other stuff comes in, like some of those things find their way to the calendar, but for the most part, the calendar is kind of full of like my to do list by personal life, random sales calls, random distractions, random meetings, and we felt like You know, organizations just don't pay enough attention to this thing.

[00:08:41] 

It's been the same standard for like 30 years and no one questions it. No one really spends time thinking about it. No one really spends time trying to make it better. And our belief was that it This didn't get better by just building a calendar app. This didn't get better by just like putting a new coat of paint on what was there.

[00:08:58] 

It really got better by the calendar sort of starting to get smarter about what it knows about you because that's really the core problem, right? Is humans are making all these decisions themselves. They have to do all, not only the moving events around part, but the cognitive part of like, If I trade this thing off, what's the impact on all the other stuff I'm trying to get done?

[00:09:17] 

Like what, how am I negotiating my time around my priorities? And so I think a big part of our kind of mission here was to really think about Reclaim is more of like an intelligent scheduling engine or like almost like an operating system. As opposed to like, let's go build a productivity tool and and because we were people with this big background in instrumenting complex infrastructure systems and instrumenting applications and like our whole orientation of the world was how do you get visibility into these systems?

[00:09:46] 

How do you make them automated? How do you take all the toil out like all the stuff we did for developers? We were like, we can do that for time and I think that's again. I think that's part of why what we landed on was a little different than what you see in the market because. I think I'm not saying anything disparaging about anyone else out there, but I think a lot of people look at this problem and say, Oh, what we really need is like a calendar with keyboard shortcuts and it's like, yeah, that's that will solve a problem or a set of problems.

[00:10:10] 

There's definitely room for better workflows there, but That core issue of just like, why is it really hard for me to express the complexity of what I'm trying to get done and what's important to me and my team to this system that's supposed to determine where I spend my time like, why is that so hard?

[00:10:27] 

And we believe it's it all comes back to making the calendar smarter. 

[00:10:31] Patrick Lightbody: 

And I would just add briefly, just say, in addition, we founded a company called reclaim.ai well before people were talking about GPT. Obviously AI has been a broad topic for a while, but we felt very strongly that everything Henry said had to be underpinned.

[00:10:51] 

With action, the actual, you know, assistance and automation. And that was why we named it reclaim, which kind of speaks to the, a lot of what Henry is speaking to and what you were speaking to, you know, reclaiming your time, being more intentional on your time and AI together is really key to it all. 

[00:11:09] Josh Sharkey: 

Yeah, no, I love that. And it's funny because I don't even think of it as a calendar app. I think of it as just like a, a way for me to continually prioritize And reprioritize my time and, and take ownership of my time because it's such a battle all the time. I don't know about for everyone, but, you know, obviously for a lot of us where, you know, you have these calendar links.

[00:11:28] 

And that's another thing that you guys have, or just like Calendly, like where you can get a calendar link, but here they're, they're much smarter. They're more prohibitive, which is great. Meaning like you can determine when someone can book, not just like in terms of your availability of hours, but how far out and what types of things and different calendars and, And for me, like it really unlocked this ability for me to actually kind of like have a weight off my shoulders of I don't have to worry about who's going to take up my calendar anymore.

[00:11:54] 

You know what I mean? I know if I have like things that like are table stakes part of my world, I have to have strategy time. I have to have family time. I have to have time to read. I have to like those things. Maybe they get shuffled around, but they never get, you know, removed and people have to work around that and not the other way around.

[00:12:11] 

And my assistant doesn't have to work around it either, which is great. Yeah. So I, I love that. It also, like, you both are engineers or product people, you know, and I don't know if you ever read Mythical Man Month, one of my favorite books, and I'm a chef, so it's like, why would, why would I love that book, but it, like, blew my mind when you think about, like, the challenge of time, of, like, humans are terrible at estimating how much time something will take, and the surface of that is, like, just take a week.

[00:12:36] 

You're like, I want to get all this stuff done this week. Well, guess what? You don't even have enough time to do all the things that you want to do this week. Yeah. And I think that's been a huge part of what you guys have been able to solve for, which is awesome. So, you know, like why you started and I, and I realized now we've just kind of like been spouting off for a while, at least I have, and then you talked about your origin, but maybe just for the audience, like just talk a little bit about like what reclaim is at least how you talk about it. And then, and some of the features. 

[00:13:01] Patrick Lightbody: 

Sure. Yeah. Yeah. You know, kind of continuing from Henry's origin story. A lot of our initial inspiration was very much of the features we built and I'll go describe them kind of as we built them was really anchored in real life kind of needs and jobs that had to be done that we were already doing in some way.

[00:13:21] 

I also say Henry and I are very pragmatic people. We call ourselves meat and potatoes kind of people, meat and potatoes entrepreneurs. We just like keep it real simple and just build and iterate. And as someone who's been using the product, you've probably watched it go through those iterations. The first thing we launched was maybe, gosh, I want to say it's like one month before the pandemic, uh, it was like right as the pandemic was opening up and we called it life work calendar.

[00:13:45] 

It wasn't even reclaimed yet. And it was a tool to make sure that your work calendar appeared busy whenever you had a meeting on your personal calendar, it's just as simple as that. And I'm guessing a lot of your audience that that resonates to them in some form, right? Everybody is maintaining at least two kind of lives and schedules in some form.

[00:14:09] 

They intermixed together and as the pandemic, you know, really started kicking off, it obviously got even crazier. But even before the pandemic, this was, this would be a problem for, for busy professionals. It'd be like, Oh yeah, I said, I meet you. I do that meeting with someone at work. And Oh crap, I forgot. I actually have to take my kid to soccer practice at that exact moment.

[00:14:28] 

And so now I've got this little micro stress that is building up in my life around making choices of, Who am I going to disappoint my kid, my spouse, or my, you know, business partner. So we just started with simple jobs that people needed to be done around their schedule to build trust and confidence and kind of this reliance that yeah, there is, there is a technology solution that can help you manage your schedule and help you be a better version of yourself.

[00:14:56] 

So we started with one of our most popular features is called calendar sync. And that's the one I just described. Along the way, we discovered that it is massively popular with people who maintain like consulting practices or side gigs, because it turns out in addition to your personal calendar, sometimes there are people out in the world who have three or four or five separate work calendars and life is even crazier for them because.

[00:15:21] 

People in one organization think they're free when in fact they're actually busy because they have, you know, double or triple bookings going on all over the place. So we, we synchronize that. That's one of our like most basic jobs in the like hierarchy of calendar needs. That's that's kind of the baseline from there.

[00:15:37] 

We have a feature called habits and you alluded to some of that. And that's really about being intentional and making some time for goals that you want to achieve on a regular basis. And they can be sometimes very necessary habits. Like I need to take a break in the middle of the day so that I can feed my body with some nourishment, aka have lunch.

[00:15:56] 

And they can be more, more kind of tactical in nature. You know, I want to catch up on my inbox every morning and afternoon. Or they can be strategic in nature. You know, I wanted to invest in recruiting or learning or exercise. And so they can be both work and personal. Now, the thing about habits and that make really kind of starts to like.

[00:16:19] 

Help people understand what reclaims doing that's unique here is that they're not just like some time block that's fixed on your calendar They're actually Adapting to your changing schedule and you can express them in the way You would you would normally express something like if someone asked you like, hey, what do you eat lunch every day?

[00:16:37] 

You wouldn't say, Oh, I eat lunch Monday through Friday, 12 o'clock to 1 p.m. Right? You know, that might be how it manifests on the calendar. If you put a block on there, but typically what people would say is like, you know, often I often have a busy schedule. And if I can steal away half an hour on a busy day sometime between 11 and 2, I'm pretty happy.

[00:16:58] 

If I can get an hour sometime between 11:30 and 1:30, that's even better, you know, and, and they describe things in a more fluid way that's, that's humane and representative of their, of their busy life. And what we do with habits is we let the user express those things and tell us what matters to them, express those ranges of time, those priorities and, and set those priorities relative to each other.

[00:17:21] 

And then reclaim start scheduling it. And what's beautiful about it is it adapts. So if someone invites you to a meeting at 12 o'clock, that lunch block might move to 11:30 or one o'clock, depending on what's most ideal for you. And what's even more beautiful. Is it actually kind of like a circuit breaker does for, you know, your electrical panel, it will naturally defend the time by marking it as busy on the calendar or marking it as free.

[00:17:50] 

If you have lots of flexibility and the benefit of that for busy professionals who are trying to meet with other people is availability is an important communication tool on the calendar, how available you are to your coworkers or your customers. Impacts your job for for a lot of people. And so what we do is we naturally choose whether to make those things free or busy based on the holistic schedule and the holistic priorities that our customers are interested in so that, you know, those two are like our kind of most popular features today.

[00:18:23] 

And they're really about like intentional time and defending of your time, but also leaning into the idea that meetings are okay, but so is some time for yourself and you've got to be able to defend it and adapt it. And then all of this is in the backdrop of a scheduling assistant that's reacting in real time.

[00:18:40] 

So when a meeting lands on your calendar, you don't wait a day or a week to see things adjust. You don't have to take action. reclaim's working in the background. And so usually within a few seconds of accepting a meeting invite, you'll see things adapt. 

[00:18:52] Josh Sharkey: 

Yeah. The way I learned about reclaim originally is some people on my team, I didn't know what they were, what they were doing, but I started seeing all this like decompression time on like before and after meetings, they would have these things that just like decompress or, and at first I was like, what's going on here?

[00:19:09] 

And then I was like, Oh, that's nice that they're, that they're setting that for themselves. And I was like, that's a lot of work, but cool. So I could tell they were like putting time before and after meetings to just like decompress. And then my, actually it was my, my director of CS, Sarah. I asked her about it, and she's like, oh yeah, we use this thing called Reclaim.

[00:19:25] 

That's how I found out about it originally, because you also have these things called buffers, which is like, if you're traveling, you can set settings to say, hey, make sure that, like, someone can't book a meeting with me if I have a meeting away from my home office, or away from where I'm working or living, because I obviously have to travel there.

[00:19:40] J

And so there's all these like buffers that I think are really helpful as well. Also, it's interesting, like so much of this product, and I think this is what I love about great product is it really touches the human nature and philosophically how we think, because I don't use deep repression times. Cause I don't want to, I want to optimize my schedule.

[00:19:59] 

So like I don't have before and after resting, you know, I put time in my day. In reclaim, there's like a personal reflection for five minutes while just stop and meditate or do something, you know, but that's just sometime in my day. It's not before and after meetings. And you can see how different people think about how they manage their, their time.

[00:20:19] 

And it is so, so much of it is like, how do you, How do you value the, the, the way you spend your time in a, in a given day? And, and I think that's what is cool about this product is, is that it allows you to, to take action on that and, and also see in a week at the end of the week, Hey, by the way, this is how you spent your time this week.

[00:20:37] 

This is how many people you met with, and this is how much decompression time or personal time. And last week, Sarah like gave a shout out in the, in the all hands, because like, she was proud of like how much, decompression time she had or something like that. That's what I find really helpful. Look, there's a lot of other things we could talk about in the product and I want to because I think there's some just some really interesting things that have been like bulbs for me about how I, I, I now, I've been an Asana fanatic for a very long time and now I just moved over to using reclaim.

[00:21:07] 

It's a cleaner way for me to like actually understand how much work I have. Let's talk about task lists for a second. And then I actually want to talk about creativity and Building in general, because I want to, I think that's, you guys obviously think about that a lot. Task lists, checklists in general.

[00:21:21] 

have a lot of flaws for sure, right? You just write a whole bunch of things that you need to get done and then there's no correlation to how much time it's going to take, which one is the most priority versus the least amount of priority, what is the context behind it. And so I moved over actually pretty recently to tasks and I started putting, you know, I moved over from Asana and put my due dates and about how much time I thought it would take, which It's the first time I've been, I've done that.

[00:21:42] 

Like, Oh, I think, cause it asks you how much time will this take? And I was like, Oh shit, I'm not going to get that thing done. Like I'm flying to Chicago this weekend and I have to go to Michigan after that. And I have this thing I'm working on. And it was like, I actually don't have time in my calendar.

[00:21:57] 

Now to get that thing done that I need to get done. And so I had to, it was a real light bulb. Cause it was like, Hey, you're not going to get this thing done. And I realized that that would never have happened if I hadn't moved over, you know, to task lists. So before we get into that, just like, what is your thought on Checklists, task lists, things like that.

[00:22:12] 

And is there anything that you like about them or are they out the window? No one should use them and that's why you do, you know, built what you built. 

[00:22:19] Patrick Lightbody: 

I mean, Henry, I'm certain you've got lots of thoughts here to add as well. I will just say, one, it's a deeply personal thing. Like, I mean, some people just literally work best with sticky notes around their monitor or rewriting their task list 10 times a week on different script pieces of paper.

[00:22:38] 

And just the act of writing it is calming and helps them kind of, you know, center, center themselves. And so I would never judge or, or discourage anyone from using whatever system works best for them. Definitely the classic adage, you know, what is it actually now I can't remember the classic it's a planning planning is everything the plan is nothing.

Is that right? Or is it? I got it backwards. 

[00:23:03] Henry Shapiro: 

Plans are useless. 

[00:23:03] Patrick Lightbody: 

Plans are useless. Planning is everything. There you go. And I will say having at least being being able to start to think about, you know, the actual bounds of the time to your point around like, Oh, how many hours do I need to write that post, you know, or, or research that market or whatever it might be, just the act of putting it down and then, and then letting reclaim try to fit it on the calendar is illuminating for a lot of people because it's easy to say like, Oh yeah, I've got these 10 things I want to do and they each take 10 hours.

[00:23:37] 

And you don't really appreciate that you just booked up your entire month. And so we do like that we're, we're in the business of helping people understand that, but I wouldn't say that our mission is to replace all forms of checklists and tasks by any means.

[00:23:52] Josh Sharkey:  

It is a checklist. What's in there is a checklist. It's just behind the checklist is all of the magic that's happening.

[00:23:58] Henry Shapiro: 

Yeah. And I think maybe even just returning to your original question about like, what is reclaim? And you brought it up in the form of like, It's really dependent on what people's calendars look like. The reason we didn't go down the path of, I don't know, there's products out there that are really dead set on like the thing you should aim for is maximum focus time, minimum meetings.

[00:24:20] 

You know, you're all your meetings should be batched together, and that's like what we're going to try to optimize your calendar for. And that maybe makes sense for certain types of people, but not for everybody. Similarly, there's products that are really oriented towards tasks like it's all about replacing to do list or replacing your task list.

[00:24:37] 

And, you know, we've taken a strategy that's a lot more about we want to be a system that makes sense for any type of calendar. If you're the kind of person who takes a ton of meetings and you can only squeeze in like a couple hours a week for focused work because your calendar is just bananas like we want to help you get that time.

[00:24:53] 

And we want to sort of acknowledge that. It's not that meetings are inherently bad and focus times inherently good. You just have a different view of the world, right? Your priorities are just different than, say, a I see engineer who maybe has two meetings a week and has the luxury of like a pretty empty calendar.

[00:25:09] 

So with regard to, to tasks, I think the way I use them and the way that I think a lot of our more sort of manager oriented folks use them is a thing graduates to a reclaim task when it is something that is going to get stolen from my calendar if I don't make time for it. So like I need four hours to go write my investor update.

[00:25:30] 

I know that if I don't get it on the calendar and start having reclaim manage it for me, I'm going to do it at night and on the weekends and I'd like to make sure I have time set aside for that for the like, I need to respond to this thing, do something I use habits or I'll even I'll still use checklist for certain things because to me, I don't think of it in terms of it.

[00:25:50] 

I want to block out every single moment of my day. I think of it more in terms of what are the things that if I don't make time for them are inevitably going to get chipped away at. And so there's these universal concepts and Patrick alluded to a lot of them, you know, automation, flexibility, extensibility, being able to integrate with other sources, prioritization.

[00:26:10] 

There's these universal concepts we think are relevant for any person who has a calendar, but what you end up doing with those things, which features you end up using more or less. And, Which ones you kind of end up getting more value out of can be really dependent on on what kind of schedule you have and what kind of role you have.

[00:26:28] 

Yeah, so I think we have some users, for example, with tasks who are their whole asana list, their whole to do is list their whole clickable list. It just gets imported directly into reclaim and they use that as like their Bible. Like that's what they're they're really spending their whole week around.

[00:26:42] 

But when you talk to those folks and kind of look at schedules, you're like, Oh yeah, like that makes sense. Like you're really into having everything plotted out. And there's not a lot of other things competing for your attention. It's really more about you having a plan for every day, which makes perfect sense.

[00:26:56] 

And then again, those managers are more like, I just love that I can squeeze like six ish hours a week to just get something done that isn't going to hold my meetings. 

[00:27:05] Josh Sharkey: 

Yeah, it's the, it's the, it's the whole Paul Graham maker manager schedule. Exactly. Yeah, exactly. At the end, I wanted to do a little segment on some ideas.

[00:27:15] 

Yeah. So, we'll get to that, but let's, I want to talk a little about just like how you all think about building product, because as I've learned more about technology and And building, you know, product and UI and tech, you know, my whole life has been as a, as a chef and mostly in the fine dining world of, of, of cooking.

[00:27:33] 

And even when I owned restaurants, I was still very culinary focused. And so I've always been kind of like, I like to create and build and that's always manifested in food and only, you know, recently in the last few years in technology and man, I love it. Like I love building product and there's. There's a very similar, like, I don't want to say, uh, like, gratitude or that you get when you build something and you see the emotion that can be elicited from the thing that you build and the feeling and then, of course, the problems that you can solve is great as well.

[00:28:02] 

And then there's even these levels of, like, hospitality. In technology that you can do where people are like, oh man, I don't have to worry about that. Wow, I, they thought of that too. And like, there's this guy named Will Guidara, you guys know him. He has a great book called Unreasonable Hospitality and had the number one restaurant in the world and when you eat in his restaurant and similar restaurants, you might have experienced it before.

[00:28:23] 

You walk in and, you know, like, they already know everything that, you know, about you and what you've, you know, had before or what you like and you sit down and you forgot your glasses and they bring you a pair. If you can't read, if it's raining, they give you an umbrella on the way out. Everything is thought of.

[00:28:39] 

And there's a similar sort of parallel with tech where you can create those experiences. And so I'm teeing that up because I want to, we'll step aside from just like the, the specifics of reclaim for a minute and just talk about what makes great product in your guy's eyes. And then also, And this is still something I try to figure out is like, what makes a great product manager in your eyes?

[00:29:00] 

And we're going to have to talk a little bit about what is a product manager because it's, it's foreign to the restaurant world. Because I think in technology, you have someone in product that's like coming up with these things and speccing what it should be and why. And then you have engineers that are implementing this thing, and sometimes they're getting into the more of the details, you know, I'd love to, like, understand what maybe some one of the heuristics that you think about when you build product and what makes a what turns a good product into a great product?

[00:29:23] Henry Shapiro: 

I think there's a lot of product management gospel, and I certainly read a lot of it when I was, like, learning how to be a product manager. I actually started working in product management roles and realized, like, there's actually all these things that no one talks about that make you successful in that role and make you successful at building product that are sort of unintuitive, I guess.

[00:29:44] 

And I feel like, I mean, in terms of product, it's like, I think the thing we talk about a lot is, like, details matter. I think it's really cool to have a strategy and it's really cool to sort of talk about, like, Leveling up and people get obsessed with this of like, you know, I want to be really high leverage and pull big levers and have big things happen.

[00:30:04] 

And they get really caught up in like the, I just want to make five big decisions a year. And that's all that really matters. And it's like, no, like you got to like really dig into the details of every single little thing. And you brought it up around hospitality. It's like, that's the stuff that's delightful.

[00:30:20] 

And it's why in the really early days, We put intercom in our product and had live chat and still have live chat to this day because we think A. it's a wonderful way, especially in a space where people are like trying something really different out for the first time to stay close to folks and make them feel trusted.

[00:30:39] 

And we, you know, we get, we get very high marks on that experience. But also you, you will learn, I think, far more about what the hell, you know, people are doing with your product and running into with your product by talking to them directly in a support queue than you will by looking at even like user data or even watching like user interviews and user research and walkthroughs and stuff like those, those have value.

[00:31:03] 

But I think that live interaction with people is just there's no substitute for it. Yeah, I think that's been a really big part of our journey and it's part of why also I think we tend to be more incremental in the way that we work because the idea that you're going to get something right on the first go around is just, it's just not, this is not how it works.

[00:31:21] 

And the beauty of software is you get to iterate on it like infinitely. You can, you can ship something that's. Just barely scratching the surface of the problem and learn from that. And it can take you all sorts of interesting directions. And you know, if you look at what habits was Patrick, I don't think mentioned that the name of it, but it was called lunch buddy.

[00:31:39] 

Literally all it did was schedule lunch and it was a hard coded 11:30 to 2 p.m. You know, if you look at that product and you can, if you go on product on and look for lunch buddy, you'll see it. I mean, the screenshots of that thing, you can see the kernel of the idea in there, but all of like the stuff that we've built around habits as a platform.

[00:31:57] 

Now it's been years of just chipping away and chipping away and chipping away at it. And so I think that's, I mean, that to me is also what makes great product managers is that they just, they stay very hungry and they, they kind of get obsessed with, you know, the details. There's obviously danger in that too, but I think, you know, you, you really try to be careful about all the little decisions that get made because you know how much that impacts the experience.

[00:32:22] 

And also, It's like eating a whale. You know, you just want to, you want to do it one bite at a time. So yeah, we're, we're not big on the like go stealth for two years and come out with the perfect product thing. I mean, which is an approach that's out there and some people operate that way, but not as much.

[00:32:36] Josh Sharkey: 

That's part of what I love about technology. I did, I never knew it took me a long time to learn is that notion of almost like the, the Kaizen sort of approach of like just constant iteration over time. And, that doesn't happen so much in the culinary world to be honest, like you have to one because like you're gonna eat a dish and you paid for it and you know, you might not ever come back and it has to be at least pretty darn good.

[00:32:59] 

And so we tend to do R&D in the background for a very long time before we put something out and then and then we can iterate on it. There's some threads I want to sort of pull on there, but I think. One thing that, that I really love about, you know, building technology that I wanted to ask you about was like, I totally agree and I love that you said the details matter because they do, they matter just as much in food, especially when you only have like three things on the plate, like they have to be, those three things need to be put together.

[00:33:22] 

Perfect, because you can't hide behind those garnishes and things like that. And in technology, yeah, if you put out, like, whatever that thing is, the first version of it that you can iterate on, you have to know, like, what is the distilled down idea that is, like, the, at the root of the thing that you're trying to solve.

[00:33:40] 

Yeah. And just that, and that is so hard, you know, to do is like, what is like this, like, you know, the, the purest thing that I'm trying to achieve here that I can iterate on. And I'm curious, like one, how you, how you navigate that. And then just generally speaking, like, how do you prioritize what to build next?

[00:33:59] Patrick Lightbody: 

Yeah. Yeah. I mean, it's, it's this funny thing where my version of the answer that Henry gave would be, you know, good taste, innate curiosity and ability to be comfortable going back and forth between tactical and strategic and being okay with operating in the here and now and also having an eye towards the faraway future.

[00:34:25] 

I think that's especially important in, in a, you know, the entrepreneurial kind of product creation, like we've been going through the last few years, but I think it applies even for mature products, you know, to kind of back that up. I think it would help. To explain, you know, when I said our first product was our calendar sync feature, it's actually not technically true.

[00:34:46] 

We built something that we threw away and never shipped. And it's actually much closer to what we, where we are kind of now. Like it took us five years to get back around to where we are now. When we first started reclaim, we built a prototype where we asked users to type in their priorities in their own words.

[00:35:06] 

And then go tag every calendar event with those priorities. And then we would make some recommendations and hopefully rearrange their schedule and, and kind of shock them, you know, hold the mirror up and be like, Hey, did you know that you're spending only 5 percent of your week on your number one priority?

[00:35:21] 

Don't you feel bad? And we, we built a rough prototype quickly. And what we discovered was People were really stressed out about that. Like the met. And so when, I think when we talk about like good taste and curiosity, like it was disappointing to find that answer out to find out that like, we were asking a question that was making people uncomfortable to the point that they weren't engaging in the early version of the product and having a little humility to step back and say, Yeah, Okay, this is going to take longer than we thought.

[00:35:55] 

What can we do that is a first step on that long north star direction that we want to go towards that will bring us there inevitably? And that's been, I'd say, I'd say as a person who's hired a ton of product managers over the years, and as someone who's been with Henry in the trenches for the last five years, that has served us really well to always be keeping an eye on what that north star looks like, but willing to step backwards a few steps and and build something that that puts us on that trajectory and sometimes even acknowledging and we have to say it out loud.

[00:36:32] 

This is a slight detour from on that journey, but that's okay because it is directionally going in that where we want to go and it's fueling our business and it's opening us up to new opportunities. So, yeah, it's hard. Like, how do you, how do you collect all those, those skills? There aren't a lot of people that have them all innately.

[00:36:52] 

And so then the next step is like, well, how do you develop those skills? And usually you find like some product managers and entrepreneurs and product designers, you know, are naturally better at, at some than the other. I might be projecting a little too much, but I will say. You know, I would agree with Henry's point that there was a natural disposition, especially in the tech world where you can go read Twitter and read all these essays from highly influential people and kind of try to distill it down and be like, Oh, cool.

[00:37:21] 

I just have to make some long term bets and it all works out. So I will say we tend to find in the wild product managers who are a lot less kind of ready to get their hands really dirty and be okay with that tactical work. And so I would say anyone who's interested in tech and interested in building products in, in, in this model.

[00:37:43] 

You know, try to fight that urge and it's not to say the strategic mindset and, you know, kind of begin with the end in mind is not a valuable skill, but it turns out there's a lot of people who have that, I guess, you know, in some ways it just kind of comes back to your classic, uh, inspiration, perspiration, you know, kind of thing you gotta, you gotta grind it out to 

[00:38:03] Josh Sharkey: 

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[00:39:11] Henry Shapiro: 

Yeah, and sometimes I think also, I mean, part of what, Patrick, you reminded me of is like, what is literally your vision? Is so often not the thing that actually helps you to prove the thesis of what you're trying to go build. Yeah. Like what calendar sync, AKA life work calendar, what it proved was people are open to the idea of a little bit of automation in their calendar. It was the first proof point of like, we can do a job that humans currently do manually that sucks.

[00:39:40] 

And it's a, it's a tiny little step towards them getting comfortable with. A thing we think at the time we called it reclaim bot. I mean, it was basically like a thing, a thing in the background that's kind of constantly watching and getting your back on just this little job that you're doing all the time.

[00:39:56] 

And we really badly at the beginning wanted to go straight to the jugular of like, okay, it's all about priorities and time. So let's build a thing that combines priorities in time. Yeah. And and ultimately that didn't help us to really prove what we believed, which was, yeah, to really solve that problem.

[00:40:13] 

It's not just analytics. It's like it's action and we have to get people comfortable with this notion that that they should trust us to manage their calendar for them. And that's a big that's an even bigger leap than getting comfortable with the idea that your priority should be aligned to your time.

[00:40:27] 

Everyone sort of agrees with that in spirit. But getting something that starts doing it through software is kind of like that's the that's the whole bet. And yeah, and I think that portion of I was kind of thinking about like what the equivalent role would be. My stepdad growing up was a GM at restaurants in New York for a long time.

[00:40:43] 

And I sort of like for some reason, I've always thought of like the product manager role as like somewhat similar to that role where it's like he worked with a whole bunch of different, you know, managers and GM's over the years, like some of whom really exuded that sort of like, you know, I don't need to be in the details like I'm here to like work with the work with the partners and like, you know, make sure the front of house is doing well, but I'm not going to like, you know, deal with this, you know, mess.

[00:41:07] 

And then there's like the guys that like are, you know, there's no problem too small kind of thing. And I, I think that kind of, I think the best product managers we've worked with over the years have been above all, like willing to kind of carry the water and, and be the folks that kind of, yeah, dig into the details and have an immense amount of like humility about what they're building. 

[00:41:27] Josh Sharkey: 

I love that. But I think also what I'm hearing from you all just when I hear you talk about it is The first thing when I think about a good product manager is Ben Horowitz, good product manager, bad product manager, a lot of that's very tactical, you know, but I'll put the link in the show notes for anybody that cares.

[00:41:41] 

I hear a lot of like emotion in what you guys are talking about. I mean, even just like the, the idea that you had, you then saw how it made people feel. And you had to change course and then it really resonates honestly a lot with me as well because I basically like divested from my restaurants sold them and said, I need to build this product because I, I want this thing and it doesn't exist and no one's building it and no one really cares.

[00:42:03] 

And I was like, I want, I want to make sure people can be creative or when I say people, like I want to make sure the culinary folks can be creative and profitable. How do I do that and build this sort of universal recipe medium and The way to go about that on the surface level would just like build a really cool recipe like you know platform that does all the features that you need for it to you know cost and train all these things and then you know very quickly in the way we realize oh actually one people are very particular about like their recipes to You know, getting the shift from moving from, you know, a Google sheet or a Word doc to software, even though Google sheet is software, isn't just a technical barrier. It's an emotional barrier. I've been doing this my whole life. 

[00:42:47] Patrick Lightbody: 

It's a safe space that I've built up. Yeah. 

[00:42:49] Josh Sharkey: 

And I created these formulas and I, and I did all these things and like, don't touch that. I want it to be just like that. And we realized like, okay, we actually can't think about any like business features for years.

[00:43:02] 

All we're going to do for the next. However long it takes, you know, is adoption. How do we get people, how do we build technology that lets you take your stuff and put it in here and it magically is even better than it was before, but you, but still familiar. And that was not the plan originally to build like a language model, to parse recipes from all the disparate formats and make sure that they still have all the, all the things plus more.

[00:43:26] 

And that was not what we had originally set out to do. And we had to spend an insane amount of time and money to build that and still iterate on it, you know, every day. And I would have just started building all this like menu profitability things right right away. It's really cool to hear you say that, but I also I have to imagine it's a blow to the gut.

[00:43:45] 

We're like, Oh man, this is a much harder problem than I thought it was going to be. 

[00:43:49] Henry Shapiro: 

Yeah. Yeah. I think we coming from monitoring Patrick and I. When we first started working on this thought like this should be really easy like monitoring. There's no harder problem out there than developer automation and developer tooling.

[00:44:03] 

And that is a hard space for sure. But you mentioned kind of the emotional side of it. And I think that's something that's been pretty unique about this space is We didn't build a lot of products. I think over the years that people had a deep enduring kind of emotional attachment to, you know, they use them as part of their work.

[00:44:22] 

They relied on them in their in their job. They liked them. That wasn't like they didn't have any sentiment. But this, you know, this idea that you're building something that it. Literally is going to control how people spend their time and and help them to feel in control of their time or out of control of their time.

[00:44:41] 

Um, and and hold up a mirror to them in certain circumstances. I mean, We see it both in the sort of positive and negative sense, right? Like along the way, we've had been really lucky to have, you know, tens of thousands of people that, you know, proactively reach out to us and tell us, you know, what an impact we're making on their lives.

[00:44:59] 

We've also had people have reached out to us over the years and said, Oh, my God, you completely annihilated my calendar and, you know, it was due to a bug or some issue. It's like the margin for error here is so, so, so, so low. And so it's really been an interesting kind of challenge and figuring out how to build something that also works for.

[00:45:19] 

And you kind of brought it up in the scope of like people who are used to doing it their own way or have a system already or have a way that they've kind of embraced it for a long time. You know, building something that can kind of accommodate different styles of working and different styles of kind of doing this job, I think, is is challenging, but it's part of why we didn't go down the road of saying we have really strong opinions that it should be that the perfect way to manage your time is like Eisenhower Matrix or it's Pomodoro's or it's eat the frog like you can use reclaim for all that stuff.

[00:45:51] 

If you want to build your schedule that way, But we really didn't want to come in with this perspective that like this one person got it totally right for everybody, you know, near I all totally nailed it and therefore we're just going to take all of their ideas and push them in. I think we take inspiration from like hearing from our users and seeing ideas that we're like, oh, that's that's something that's kind of generally useful and could be reapplied to lots of different methodologies, but that isn't like embracing one way of doing things, you know.

[00:46:22] Josh Sharkey: 

Yeah, and I think a really great lesson for, for everyone, and this actually applies to anywhere, it definitely applies in restaurants, is you can build a lot of, you know, resilience of the things that go wrong when you, when you do things the right way, like your product is very thoughtful, very clear that like there's a lot of, you know, every detail is thought of, and then of course you have like live chat, you have all these things, you have all these things.

[00:46:42] 

And it's the same in a restaurant where, like, shit's gonna go wrong, right? Something's gonna get burned or somebody's gonna get the wrong thing and somebody's gonna get something that they're allergic to. That happens, right? And usually it can cause a storm, like a shit storm. But if you created that sort of trust, that level of trust, because you know, like, okay, this place clearly is thoughtful, is clearly thinking about, you know, is thinking about me, they care, and their food is awesome, or whatever the thing is that's really good, then.

[00:47:09] 

Okay, I can, I can get over this and I'm gonna, you know, I'm gonna react differently. I remember when you guys moved to the new format. Actually, that's how I met you originally, because like you moved to the new format and I was all set up with my calendar and then everything changed and I was like, Oh my God, you know, if it was a different app, I would have been like, what the F, you know, but you know, we, we solved it quickly and Patrick actually got on the call and helped exit, you know, at least help me understand.

[00:47:33] 

And then it sort of fixed itself, but that that's so important because all that stuff is going to go wrong. You're going to, you're going to have another bug. You're going to release something else and it's probably going to, you know, screw something out. Yep. When you build that trust. 

[00:47:43] Patrick Lightbody: 

One thing I would add to that is with technology, I'd say even more so, I mean, this, this applies with, you know, physical buildings, you know, architecture, you know, almost any business, I'm sure, I'm sure in the, the restaurant industry as well, you know, designing recipes and dishes.

[00:48:00] 

They can have fallbacks. It's like, oh, shit, we ran out of this ingredient. This fish isn't available today. So we need to switch to something else. You know, you want to have those contingency plans. It matters a lot, for sure. I mean, what you were talking, what you're describing resonates a lot with me. And Henry, I don't know if you were thinking about when Josh was mentioning some of that first thing that came to my head is, you know, We made a very, very intentional choice and it's so low level, like so low level, but the ID patterns that we use for the events that we put on on people's calendars.

[00:48:33] 

It happens to be that Google Calendar lets you either say, Google, you make an ID randomly for me, or Google, I will supply you with an ID. And I know it sounds really low tech for your, for your listeners. But one of the things we did is we chose a pattern that basically is our fingerprint on those, on those events.

[00:48:52] 

And it gave us so much confidence. In doing the right thing for them because it meant that we knew every single thing that was on the calendar that we created and that we didn't create and we could put into the code logic that would say never ever touch a meeting that we are responsible for because like the cardinal sin of our product would be canceling a meeting with someone they care a lot about.

[00:49:15] 

And so it's this funny intersection of humane design and having this like emotional connection to the user, but also coming up with technical solutions that can underpin that and guarantee that promise in the same way, you know, you can have architecture that's beautiful, but might kill everyone if there's ever an earthquake.

[00:49:36] 

And so you need both, right? You need, you need a beautiful architecture that also is resilient and designed to, to be functional and, and survive. Uh, any sort of unexpected disaster. That's like the love of technology and entrepreneurialism is that with software, you get to iterate your way through that and learn every day with architecture.

[00:49:56] 

For example, you do not. And even, even in the restaurant industry, I'm sure, you know, a bad weekend because you hadn't planned for that could be devastating to certain businesses. 

[00:50:06] Josh Sharkey: 

Yeah. Yeah. I don't know how much you think about this because it was, it was definitely like a culture shock for me. We started releasing, you know, in the kitchen.

[00:50:13] 

You create a dish, and, I mean, you plan beforehand for, you know, sometimes for a long time, sometimes for, you know, sometimes for a year, sometimes for a month, and then you put it out, and you're like, that's my food. This is, like, I've created this thing for you, and this is the final thing, and here you go.

[00:50:27] 

And in tech, you know, I find myself always on these conversations when I'm talking to someone and, and usually they're like, Oh man, I love that thing. And I'm like, in the back of my mind, I'm like, it's not even close to what I want it to be. There's so many more things I want to build. I hate that feeling.

[00:50:42] 

So my question for you is, it sounds like you, that resonates with you, but are there things right now that you can think of you're like, I know this needs to be in the app and it's just not there yet because we just haven't had time to build it , and it's like, yeah, we could probably spend the next hour on this, pick a couple that are like, you know, the most.

[00:50:58]

Yeah. . It's the worst feeling. By the way, I didn't know this because I don't come from this world. I'm like, every time I have a conversation and I'm like, yeah, but you know, it needs this and, but like, you shouldn't be needing to do that thing and we are gonna, we're gonna solve that. Yeah. 

[00:51:13] Patrick Lightbody: 

Yeah. I'll let Henry rattle off, uh, his few favorite, but I will say that you're absolutely right and

[00:51:19] 

I think a defining human characteristic that can help an entrepreneur in technology, I think any entrepreneur, but especially one in technology is just kind of unbridled optimism and an ability to kind of stop and reflect and appreciate the progress you've made. Because, I mean, I can tell you like today, today's a stressful day for me.

[00:51:42] 

And we've had a number of, you know, bugs and issues pop up and you look at them and you, and they hit right in the bullseye of like, Oh God. Yeah. Like we could have done better there. We need to do better there. Yes. That was a thing we cut, you know, it's on there. It was on the cutting room floor when we launched that feature.

[00:52:02] 

And now I'm regretting that decision, you know, and it's so easy to fall into that because with software, you, you've got, you know, people that can potentially be using it. So you're getting feedback all the time. If you've had even a remote amount of success, you're, you're, it doesn't take very long before you have thousands, tens of thousands, hundreds of thousands of users.

[00:52:23] 

And if you form that emotional relationship, they gladly tell you all their feelings. And so you can feel it. And if you're someone who cares, you feel it heavy in a very heavy way. What counterbalances that for us all the time is. You just take a moment to step back and henry and I, as partners have been, you know, established a good ritual doing this.

[00:52:42] 

When, when things get tough as you step back and say, wow, think about how much like, look at all we did in the last year. Like that is just so much more than we ever expected and it's You know, there's a lot of these cliches, but they're cliches because they're real, like where, you know, people are terrible at estimation and they often overestimate the things in the short term, but they often underestimate the things in the medium and long term that they can get done.

[00:53:07] 

And when you go and you take that medium to long term, look back and if you've been, you know, hustling and working and grinding, you find that the list is huge. 

[00:53:18] Josh Sharkey: 

Yeah. 

[00:53:18] Patrick Lightbody: 

And that really helps center things and remind you that it's not always going to be this way. At least for these things, they'll just be the next thing and the next thing and technology is moving so fast that will always like our product will never be done.

[00:53:30] 

Literally, it will never be done. It is impossible for us to outpace the advancements of technology and the demands of our customers. But what needs to be done is, is always changing. And that's what drives us. 

[00:53:43] Henry Shapiro: 

Yeah. I mean, I think that the same is true of even like building organizations or building your team.

[00:53:48] 

And I think that that's another thing that I certainly think about a lot is, I mean, our team was, Less than half of the size that it is now a year ago. And you think about like, all the great people we brought on board, all the great things that they've built, all the things that they've kind of iterated on and that it shows up in the product.

[00:54:05] 

And every so often I'll find myself like, In Google Drive and I'll like pull up some doc somewhere that was from like 2020 and it's got like designs and stuff that we had that we were really stoked on, you know, and now you're like, oh my God, like what a like what a difference a few years makes on this kind of thing.

[00:54:23] 

And so I do think there's a definitely a value in zooming out and and I think that. Also, the other value, I think of having really deep connections to your users, and this is something you don't get as much in really big organizations. And I think it's another wonderful thing about being at a startup is you can trust when strangers tell you that they love what you're doing.

[00:54:44] 

You should trust it. And even though you're in the inside and you're like, you have no idea how much I hate the thing that you're talking about, how much you love it. It's like, You really like you should internalize it as like we have made some success. They're not saying it's perfect. It's not like they have no feedback.

[00:55:00] 

But what they're saying is like it scratched an itch for me. It really made a difference for me. And that like tells you you're moving in the right direction. And as far as like things that we want to have in the product. I mean, it's like there's at the level of the details. There's probably literally hundreds or thousands of things that are like.

[00:55:18] 

You know, all these little my new things and and that's, you know, Patrick's referring to the anxiety. It's like when you're in support and you're in the queue and you're looking at the ticket list and you're looking at the bugs, you're just like it like suddenly start swelling up. You're like, oh my God, it's not just these two medium sized objectives in the next few months.

[00:55:35] 

Like we have to fix like yeah. Hundreds of these things that have been sitting dormant for, you know, weeks or months and we haven't made any, you know, we need to really address this thing and your head can really spin around it. But I think just generally it's like to the point of Patrick, you know, saying like our product will never be done, you're never going to fix every bug.

[00:55:54]

You're never going to address every single issue in the product. And so we try to focus our energies on what would be the best things the best kind of medium sized things we could deliver to customers in the next three to six months like for our business. But also like what would make the biggest impact for people?

[00:56:09] 

I think of it at this stage in terms of like calendar real estate. We at this point can schedule almost every single thing that goes on your calendar. The one thing that we are still really obsessed with is this this workflow that we hear about. Every single time we talk to customers, which is the I need to get six busy people in a room this week.

[00:56:29] 

Oh, yeah, that's a pain. I know if I look at their calendars, there's no actual free time. So it's not a scheduling link thing and it's not really even a like a priority. It's kind of a prioritization thing, but it's like it's going to require some iteration. Like we got to Go back and forth on some times and there's got to be this like assistant in the middle.

[00:56:47] 

That's kind of managing it. It's a complicated workflow. And the reason it's complicated is it's complicated for humans to like the way humans do this is It doesn't happen in the calendar. It happens over slack and email, you know, and that one for us I mean, there's other big rocks that we're trying to move on all sorts of different parts of the product But that that issue is one that we think of as being Tremendously underserved and if it is served It's usually in the scope of like external meetings like meetings with people outside your company but the inside the company pain is like It's it sucks.

[00:57:21] 

I mean, that was like our Patrick in my entire life for a good long time when we were inside of a new relic. So that's the big one that we're kind of focused on right now. And and in between, it's kind of like be opportunistic, you know, when you see an opportunity to make something better when you when you're like, Hey, I think we I think we kind of talked about this thing as a group and we got a good decision that we can roll with.

[00:57:42] 

And I think in like two days we can make. Some good progress on this little issue, like let's just do it, you know, it's like don't wedge yourself to your road map and your north star and your media, your big objectives like be be opportunistic to find those moments to make the little details better. But you can't, you can't fix all of it and you can't address all of it.

[00:57:59] 

So you just have to kind of find the, you know, find the balance, I guess. 

[00:58:02] Josh Sharkey: 

Yeah. Can I share a couple? Please. And I, I have to imagine because this is how it works for me. Like whenever I'm like on a call with a, with a customer, cause my, my CS team and sales team, obviously they're, they're mostly talking to customers.

[00:58:15] 

So when I'm talking with them, it's, it's more often than not just like, we're just like, you know, catching up or chatting and they're like, well, you know, I need this feature. And I'm like, me too. I know, like, I want that thing. Like, can you please, like, add that to our thing so we can get another upvote on it?

[00:58:31] 

And there's very rarely a feature where someone's, like, asking for it. And you never say, like, oh, I thought of that too, but probably have. But these you probably have. But some of the things that, like, I'm finding now, like, one is, the smaller ones is, like, a dynamic scheduling link. You know, you have, like, the, you send a link to somebody, here's my calendar.

[00:58:50]

Very often, I'm like, okay, I'm For this one, I actually want you to wait three weeks to be able to book. And for you, I want six weeks and for this, because for different things. And I'll usually like send them my link and say, Hey, by the way, the next two weeks are a little crazy. Cause I'll have some free time, but I know I don't want to.

[00:59:06] Patrick Lightbody: 

We might have that solved for you already today. Go explore the personalized workflow on when you're sharing or when you grab a link. And it's in the little dot, dot, dot menu. We've been there. Same thing is like, sometimes it's either priority based or literally time based. You're like, this topic is not relevant for two weeks.

[00:59:26] 

Like I don't want to meet before two weeks from now. And so we built a feature that handles this, this personalized experience. And what it does is it takes your. You're scheduling like that. You're sharing someone and basically creates a derivative, a unique URL link you can share and embed into an email and even select some times that you want to share.

[00:59:45] 

If you want to like recommend and nudge someone to a specific time and you can personalize it and override things like the priority. The time ranges that are, that where it's eligible, like it shouldn't be available past this time or it shouldn't be available before this time, whether it is, maybe, maybe it's a normal link, but you have a very specific, you know, location you want to do that.

[01:00:09] 

And so you can override the location. Oh, man. Yeah. There's a lot of, a lot of nice little features in there. That's actually one of our challenges is we've, we've got this broad platform that we built over the last five years and our customers rarely know about all of it. And so, uh, communicating that is one of those things we, we, we need to work on and do better with.

[01:00:30] 

But I think the personalized one will help you out. And protip, it also can natively integrate right into Gmail, both on desktop and mobile. And so you can initiate that workflow right from your, your inbox. 

[01:00:44] Josh Sharkey: 

Okay, cool. I use superhuman? 

[01:00:46] Patrick Lightbody: 

Oh, yes. Yeah. No, superhuman is as soon as they have a platform we can build on.

[01:00:49] 

We're, we're friendly with that team. And as soon as they have a platform we can build on, we will, uh, we will integrate better there. The other one that I would personally love is, uh, messages. I do a lot, you know, I've almost given up on my inbox. I'm at that stage in my life and I do a lot more texting with people.

[01:01:07] 

And so being able to write an iMessage kind of to go through those same workflows is one I'm, I'm very excited for. We don't do it yet today though. 

[01:01:13] Josh Sharkey: 

I like that. I mean, there's a hundred more of that, but I won't share them here just to, just to spare everybody, but I am curious. Two things one just generally how you like if you have any sort of methodologies around how you synthesize feedback And then I don't know if you are familiar with the 11 star experience exercise you know the Brian Chesky sort of like what Airbnb is like the five star experience is that your room is available and it's clean and Everything that they said was there is there and like the it sort of goes up to the 11 star experiences You know, it's a private jet that picks you up and drops you off and there's a parade waiting for you and all your favorite foods are waiting for you there and your favorite actor.

[01:01:49] 

And it's like, you know, sort of like this exercise of what was, what is the, most insane, incredible vision of the thing that you build, because you can use that as a way to sort of come up with, how could you accomplish some of that? I'm curious just, and sort of take this however you want, but how you decide to feedback or just generally speaking, like the vision of this product, obviously there is no end state you're, you're continually iterating on it, but sort of a future vision of what you're doing.

[01:02:14] Patrick Lightbody: 

Henry, do you want to take, I'll let you pick a, you've got good thoughts on both of those. And on the feedback one, we should also make sure a link gets added because Henry wrote a very nice blog post about the mechanics of how we track some of our, uh, feedback, but there's more to it than that. Or you can share our, uh, our North star vision.

[01:02:31] Henry Shapiro: 

I'll start with the synthesis problem. I mean, I think we we have a pretty great way of of tracking and to some extent it's a little bit like what we were talking about earlier with regard to like things we want to see in the product and I think actually this goes to the heart of being a product manager to there are the kinds of features out there.

[01:02:49] 

This is just my perspective. I don't know, Patrick, if you share this, but like and actually I'm thinking about road mapper the tool that Patrick built this tool when we were at New Relic, which was this thing that would take feature requests and you could add like ARR to it and you could like sort of see like How many requests does this thing have and how much revenue is tied to it?

[01:03:04] 

And it was it was a cool cool little utility that like now we sort of do in the form of a linear to intercom integration. But my read on those systems is always like, when you think about the details, and I'm thinking like, I don't know, you know, uh, add a new option for tasks that allow them to auto reschedule less than one hour from now.

[01:03:23] 

I mean, we're talking like very granular, like this is not like a roadmap visiony thing. This is like, do this thing that like 50 people have requested. Those are the kinds of decisions that like, they kind of make sense as a thing you would consider based on volume, like within reason, you'd say like, yeah, like if a bunch of people request this thing, the cost to build it is pretty minimal.

[01:03:42] 

It's not like a massive strategic undertaking. And so that's like a reasonable way to synthesize and kind of prioritize feedback is is some combination of like instinct and volume, but 

[01:03:54] Patrick Lightbody: 

and I just want to chime in there and I'll say we have a tremendous, tremendously good system for tracing customer feedback back to these things.

[01:04:04] 

And yet I will tell you. We almost never go look at the sorted list and say like, Oh, let's pick that. Not that thing with the most votes. I don't know if we've done that ever. And so it's, it's very art and science. Often when we decide to go do a popular feature request, it's kind of like, it's been washing over us through feedback.

[01:04:29] 

And we know instinctively that it's got lots of votes. We don't have to consult it, but we, we finally, it's sort of like now feels like the right time to do that. And so, yeah, it's, uh, it's very art and science. The thing I just want to like underscore here is that, that connected, like, well, why then why bother linking all those feedbacks back up?

[01:04:49] 

Part of it is the relationship with our customers. We create lifelong fans. When we come back to them a year later and we say, Hey, remember that thing you asked about it's life, you know, and they are shocked when we do that. And it's one of Henry's favorite things to do is, you know, close out a popular feature request and then he gets to send out a notice to 300 people and these become our ambassadors.

[01:05:13] 

And so, you know, just. Just want to like highlight like it's not just blind math. It's it's very much a smart blend. Sorry, Henry. I totally took over and hijacked your answer. But no, I mean, I'm excited. 

[01:05:27] Henry Shapiro: 

Yeah, no. And I think, I mean, the closing the loop part of it is is huge. And I think that I think it's in some ways.

[01:05:33] 

It's I guess what I'm really getting at is there are things that users will ask you to build. And they're not far off from what you might actually go build. It's like, yeah, like that's a pretty reasonable feature request. That's like pretty cut and dried. And like, I don't need to do a bunch of like job to be done, persona analysis to figure out what we're doing here.

[01:05:52] 

And then there are all these things that you're like, I don't think people would ever tell us that we needed to go build priorities. For example, like that was not a thing that people were saying, like they were talking about all the symptoms. They were like, I don't like the way that tasks schedule and I wish I wish I could have like stack ranking for habits relative to one on ones and like they're bringing up all these different flavors of the problem and the way you kind of synthesize that as you say like okay we could go build all those little features and like make this super complicated system that has like A million different knobs and dials, like, or we could kind of just rethink how we do prioritization, which again was very aligned with kind of like our north star from the beginning and and I think everything we do as a company because we get we get also feedback stuff like, you know, I want you to link up with my fitness tracking app so that I can track, you know, my how many calories I burned during a workout.

[01:06:44] 

And it's like, It's a cool idea. I don't know that that idea is going to get us any closer to what we ultimately want to be, which is like an intelligent platform for teams and organizations and enterprises to manage their most complex scheduling challenges, which is really Ultimately, like a step along the way to this much bigger vision around how do we make organizations better at managing and aligning their effort to their priorities?

[01:07:12] 

Like, how do we make it so that when someone wakes up in the morning, what they're doing in the next five minutes is aligned to what their team should be doing in the next few weeks, which is aligned to what their management layer thinks they should be doing in the next few months, which is aligned to what company leadership thinks you should be doing in the next few quarters and years.

[01:07:29] 

Like, that's the. That's the world that companies want to live in. But where it is today is there's a bunch of discussion about what should happen in the next few quarters and years. And then there's all this fog about like how that translates to actual effort. And then there's a ton of people making like thousands of decisions every day about where they should spend their time.

[01:07:48] 

And so the fitness tracker app thing is like, That's cool. Like we don't like probably we're never going to build that because a we're pretty sure apple will solve it before we do and be like it's not really at the core of it's a reasonable request, but it's not like at the core of like how do we solve that problem specifically for teams and companies and individuals are sort of like the starting blocks for that kind of long term vision.

[01:08:11] Josh Sharkey: 

Yeah, it took us a long time to really learn how we want to synthesize feedback. And I think, you know, again, coming from the restaurant world, typically when people are giving you feedback, it's things that went wrong that you need to fix, uh, or just like things that they want different in the, in the restaurant.

[01:08:27] 

I mean, obviously they'll say. Nice things as well, but they're, they're somewhat binary in terms of like how you respond to them, you know, like, uh, the service was slow. Okay, we gotta, we gotta fix that or we have to find a way around that. But I find that like there's people either coming with ideas or problems and 99.

[01:08:43] 

9 percent of the time it's an idea. And the challenge is how do you detect the problem? Okay, your idea is that you want to integrate your workout app into, into reclaim. Why do you want to do that? Well, because like, I have to go somewhere else to look for that. And I look at all my like time here. Okay, well, why do you want to look at, you know, your time?

[01:09:00] 

Well, because like, I know that like working out is important to me. And so I want to make sure that I'm not doing that as much as I'm doing this other thing. Okay, cool. So workouts are important to you. Like what else is important? You know, like you get to like the, and it sounds like it's priorities, right?

[01:09:11] 

You can sort of distill it down. But people often time. don't necessarily know what they, you know, what they need. They just know what they right in front of them. They want. 

[01:09:20] Henry Shapiro: 

Yeah, I mean, I think sometimes even if the problem is one that we understand, this is the other part of being a product manager and entrepreneur is you have to say, that's cool.

[01:09:30] 

I understand the problem now and we could totally go build a solution. Maybe it's your solution. Maybe it's something else, but like it's literally not in our interest to go do it right. And that's always a really hard challenge, especially when you're an early stage business where you're like, You know, you're building your revenue base, you're building your customer base, you want to treat every single person as if they're the most important person, but you also have to be, you have to start to get to a place where you're like, there are moments where you have to start to kind of like narrow the narrow the scope of what you're doing because you could chase.

[01:09:59] 

I mean, if you go through our backlog and in linear, I mean, there's, you could build probably 20 different companies out of the set of things that are in there and it's not always completely obvious. You know, tasks are actually kind of a great example. Like tasks have the danger and have always kind of had the danger of drawing us really deeply into.

[01:10:21] 

I want you to become my to do list replacement and. There's some degree of like there are users in that cohort of people who want you to become to do list that do actually represent your ideal customer like there are people who are like, yeah, and I'm a VP of product at this company and I, you know, set up meetings using reclaim with all my, but I also really like your task feature and it's just missing these things.

[01:10:48] 

So it's like, yeah. You have those, those gray areas where you're like, it's not just one, you can't just say like, well, task is a trap and you know, it's never going to get us where we want to go, but you have to be really careful about how you invest in it and how you think about it as like a strategic pillar or a wedge if you don't think of it as like your, your core problem to be solved.

[01:11:08] 

So, yeah, there's, there's understanding the problem and there's also understanding like, is the problem even something that you should be in the business of solving at least at this point in your, in your journey as and that's. That's the other art and science, I think, of this whole, this whole endeavor.

[01:11:22] Josh Sharkey: 

Yeah. And that's also why I think the most important thing in any business for anybody is you have to, you have to know exactly, you have to know why you're doing this thing. Why did you start this business? What's the vision behind it? And then use that as a lens for all the decisions that you make.

[01:11:35] 

Because if you don't have that or it's wishy washy, then you could start to build all these things and do all these things and every, and that's not relegated just to technology. It's in any business. Restaurants are no different. It's like. Yeah, people can start asking for vegan things, or they can start asking for things that are just not why you started your thing, and maybe they are, maybe they're not, you have to know how to sort of have your decision matrix of how you do that, but yeah, like, if you don't have a really, really clear sense of why you exist, then man, it is so hard to know when to say no and yes to those things.

[01:12:08] Patrick Lightbody: 

And time goes fast. And you know, a year goes by, two years go by, and you're like, what was I doing? Yeah. You've got to protect that time. It is so important. 

[01:12:18] Josh Sharkey: 

Yeah. Well, we could talk for a lot longer, but, um, we probably all have things to do. And I'm, I'm just super grateful. One, for you guys taking the time to come on here and talk.

[01:12:29] 

And more importantly, just for the thing you're building. I think it's, it's amazing. And it's helping me get. I time back and, you know, I think that thing that you started many years ago of priorities, that's like rolling back around. I think everybody should also just think about that. You know, like I have like these at any given time, I only have three priorities.

[01:12:46] 

They call my, my MITs, my assistant sees them. And like, they're like, here's the three things that matter over the next two, three months. And everything that isn't, that should not be on my calendar or it needs to be sort of completely deprioritized as much as possible. And. The more that I 

think everybody is, I think that the more you're going to accomplish, right?

[01:13:05] 

Because otherwise you just, you know, you're just going to be sort of swimming in many, many different directions. So I'm super grateful and I'm excited to see what you all continue to build. And I'm excited to be a fly on the wall, just, you know, seeing it happen. So thank you. Thank you. Thanks for having us.

[01:13:20] Patrick Lightbody: 

Well, thank you for having us. Yeah. 

[01:13:22] Josh Sharkey: 

Yeah, absolutely. Thanks for tuning into the meez Podcast. The music from the show is a remix of the song Art Mirror by an old friend, hip hop artist Fresh Daily. For show notes and more, visit getmeez.com/podcast. That's G E T M E Z dot com forward slash podcast.

[01:13:40] 

If you enjoyed the show, I'd love it if you could share it with fellow entrepreneurs and culinary pros, and give us a 5 star rating wherever you listen to your podcasts. Keep innovating, don't settle, make today a little bit better than yesterday, and remember, it's impossible for us to learn what we think we already know. See you next time.