Shifting From Startups to Real Estate featuring David Levine

There he is. Hello. I'm going, I'm going on focus mode right now. All right, we're good. What's up, man?

How are you?

Oh, doing good. God, we— how long has it been since we talked last?

It's been quite a while. It definitely— I mean, I feel like I talked to you maybe when I was at DraftKings. That was a long time ago.

I think so. I think this was back in like 2012 when we were working on StoryApp. Like, I remember—

I definitely remember that. Yeah. And you were like, damn it, Snapchat ripped me off.

Yeah. And I remember because I think I talked to you and it was almost the same day that Apple was doing their big yearly event, which must have been like iPhone 5. I don't even know when it was. We've both been in this world for so long that I've come— I've been confronted with like really bad actors. And what it's actually done is it's become very clear what my values are and what my values are not. And like very, very clear. So like I put that up on my site now and it's like, yo, this is where I plant my flag. These are where my lines are drawn. And like I'm on this side and if you're on that side, like enjoy it, but we are not—

In terms of building product and things that you're willing to do versus not?

No, I mean just like treating people how you treat people, right? Integrity, confidentiality, like, because, and I think as I've thought about it more and I talked to an old colleague yesterday about this, I think it comes from a background in human capital consulting that I had and it was a, it was one of the largest like HR consulting firms. So like people, I mean, I cut my teeth in the place where like people are valued as like without people you don't exist, the company doesn't exist, you fail, right? So I just see all these things today now too, which is like this pump and dump, like let's hire 10,000 people and then lay them off 3 months later. It's like you guys—

I was also too young to know any better and I was still so new to tech that I didn't really have any ideas on, you know, what was going on. And, you know, you just don't really know, right? Even if you are slightly on the older side. I mean, I think I was like 29 or 30 at the time, but still, that's still young. Like, you hadn't been in the tech game long enough, considered young. You don't really know and you don't really understand vesting schedules and all that sort of stuff. And people definitely will take advantage of you. Yeah, make no mistake.

Yeah. And it's not okay. Like, I'm here planting the other flag, which is like, hey guys, this isn't okay. Like, we live in a new world now. Yeah, you will get turned up on social. Like, oh yeah, yeah, like it's brand new.

I was scared. I was scared to say anything though. I was scared. Like, I, I can remember it had blown up and I had reporters contacting me. They were like, you used to work there, what's going on with this company? They had something going on with Twitter and some sort of inside something going on. And so reporters called me and I, I couldn't say anything because I had signed an agreement and They're like, it's off the record. And I was like, I'm just a kid. I don't know what's going on.

Yeah, yeah, right? Yeah, man.

So, I mean, anyways, that was a while ago.

So. Yeah. And then you, I mean, look, it's, I think it impacts us subconsciously too. And like, here you are now and you're like, you know what? I'm kind of out of this game, this whole startup thing. And what now? I mean, you just told me like you're in real estate, like doing the family thing. Like, I wanna, like, that's my, like, what has that been like? That transition?

It's been wild, to say the least. You know, obviously I was in tech for quite a while, about, it was all in all about 10 years. You know, I've been doing the startup thing for a while and most recently I was a product manager for property operations software in the vacation rental industry called Breezeway. And I was running their operations product. And so it's all about how to, you know, get vacation rentals clean, right? And turning things over and task management. I have never been in real estate, but through building product for that type of market, I was starting to learn sort of, okay, these rules can be applied to a long-term rental, which is my family business. And so I was learning I was using my skills in tech and knowing that it would eventually translate over. I just didn't realize that I'd be moving to the family business this quickly. You know, my mom was basically just like, okay, I think I'm done. And we had no one to steer the helm. And so I was just like, I guess I'll do it. I'll see how it goes. So I spent a couple months just coming into the office, just Not even really fully committing, just seeing what it's like.

Yeah.

And it's kind of, it's like a startup in the sense that it's a business that's been around for 40 years or so, 50 years. Building is 40 years old, but my grandfather started the real estate business maybe 50 years ago.

Wow. So 3 generations then, because you're the third.

I am a third generation. Yes. Nice. And where am I going with this? And he ends up, you know, passing it on to my mom, and my mom is passing on to myself, my brother, and my sister. And so we just need someone to sort of take over. And, you know, we don't have any software. Everything is sticky notes, pen and paper. You know, there's nothing. And I'm like, What the hell is going on here? Yeah. And I start freaking out. I just have stayed, stayed away from it. And as, as a PM, and you know, you have to have your super buttoned up.

Yeah.

And this is how this feature is gonna work, right?

Yeah.

And you have to convey that. And then to come in and everything is just shooting from the hip, it's like it was night and day. And so as Many heart attacks, but I'm starting to get there. I've implemented software and so that's where we're at right now.

Well, congratulations on digital transformation.

Thank you.

I mean, yeah, it's interesting. It's like small and medium-sized businesses. I mean, it like drives our economy and it's like the last bastion of tech. So like, what was the first thing you did? Did you go straight to the CRM? And start entering data? Or was it like, did you at least have like a QuickBooks accounting system? Or was that like paper ledger that you were going through?

We do have paper ledger and we do have QuickBooks, but the QuickBooks was about 7 months out of date. No one was keeping up with it. And so we did have a paper ledger that I reviewed and was like, there's no transparency here. I don't know how to use this system. It was only the person that created it. Who is my aunt, who's, you know, you know, needs to understand software a little bit more. So, um, yeah, so, uh, we, we do have QuickBooks, but the, you, the question was the first thing that I did.

Yeah.

Yeah. So I, I, um, I started interviewing software property management companies.

Got it.

And I knew of a couple just from working at Breezeway. I knew the, the long-term rental players. And so I, I just wasn't sure of the capabilities of the software and they're more on the accounting side, not so much the operations side. And that's really what we need. So I had to, you know, interview a bunch of salespeople and, you know, go through that whole process and it was very interesting to be on the other side of things.

Yeah.

It was really cool. I loved it. I loved grilling them and like I knew to like, you know, wait till the end of the quarter and like, Get the discount.

Yeah, we use all the tricks of the trade.

Exactly.

Vendor selection process. Yeah, that's, that's cool. That's good. Well, how many, how many months in are you in your new life?

3 months.

Oh wow. So it's, it's fresh.

It's very fresh. Yeah, I'm still in the, in the, in the onboarding phase of the new software. I just got most of the accounting up to speed. I just launched the tenant portal 2 days ago. So we have people paying online today. Today's September 1st. Today's the first time we've had online payments.

That's good first 90 days. You got new, like, scalable payment system.

It's huge. It's huge for us. And it's amazing. I've been learning bookkeeping as I'm going because I I didn't really know, you know, I took an accounting class, you know, in grad school a while ago, but I don't remember any of that. So I'm reteaching myself all of this bookkeeping and I'm like, oh, okay, that makes sense. And I'm like, okay, so something comes in, you log it and then, and it's like, wow, we should have had this so much, so many years ago.

You know what it reminded me when you said your aunt was doing the books? I remember, have you seen the show Marvelous Mrs. Maisel?

No.

Oh my God, it's, it's actually really good. It's like one of my favorite shows. It's hilarious. The lead, the lead actress is phenomenal in it. But anyways, um, her husband in the show, his father and mother own, um, like a, like a wardrobe company. Like they make dresses and all this sort of thing, but the mom kept the books. And so the son came into the business to like take it over, and he looked at the books and it was just like horror. And he's like, I can't understand any of this. And she had this like crazy encoding concept with like sticky tape and bubble gum, and then like reference this thing over here. And literally nobody could make heads or tails of it except for her. But for her, it was like, what is— it's perfect. It was like the perfect system.

I like to call that tribal, tribal knowledge and all of that and the single point of failures. And as I was evaluating everything, they're all over the place. And I keep running into these dead bodies and I keep uncovering them and I'm like, I need to figure this out. And so as I'm going along, it's like a startup. I'm telling you, it's like a startup that I get to— it's stable.

Yeah.

So stable considering it was So rocky. I know it's, it's, it was so rocky. We had a lot of vacancies with the pandemic and the foundation is here, just the operational processes need to be improved and just really tightened up. I'm really loving the, I think you'll appreciate this, the sort of dollars from the bottom up rather than the top down.

It's just like a real product that real customers purchase. Yeah.

It's just like, that's something— it's like not like smoke and mirrors. It's just, okay, you give me money, I give you this space, and you can live here. And like, that's it. And like—

It's weird, right? Isn't it a weird feeling?

You're bizarre.

You're like, someone's paying money for this. This is bizarre.

Right. I will say a tough adjustment for me has been dealing with people. Um, that's just, that's just hard, right? Dealing with people is really hard. And for a lot of these folks, this is their home, you know, and a lot of them have been, you know, severely under market rate. And, you know, they see a $100 increase and they're, you know, they're like bulls in china shops and, you know, they're just throwing their hands in the air and, you know, it's tough. And I'm learning that side of things and dealing with, you know, consumers face to face. You know, first is I could, before I could sort of hide behind a screen more or less. And then, I mean, I'm hiding in the back office, but—

We won't give away your address so they can find you.

Yeah. Oh no, I live here too. So—

Oh, there you go. Hey, you're dogfooding your own product. That's great.

I am. I did. I moved in on day one and, you know, I did that just to see what it would feel like to live here. To see what it would be like after hours in the hallways, doing laundry. I really wanted to kind of see, you know, what the tenant experience was like.

Good, good for you, man. Like, how many people just don't care, you know? And like, just, I mean, that would be great if I had you as a landlord. And I mean, heck, maybe I'll just come move in at some point. And where are you? Where's the property located?

Watertown, Mass.

Okay, I love it. Yeah, East Coast, close to Boston. Yeah, man. How many units?

Um, we're 115.

Got it. And this is like apartments, like a year-to-year lease kind of thing, or—

Yep, yep. I've teased the idea of like maybe taking a couple units and doing some corporate housing, or maybe even an Airbnb, obviously with my Vacation rental background. But the deeper I got into the business, the more I realized it was just in dire need of just professionalizing and stabilizing what it already is. And so that's really, I'm treating it like I'm treating product. I have a roadmap. I'm like, here's the things that I'm doing this year, you know, because I don't know how else to do it.

That's right.

That's the way.

It's been ingrained in you. Yeah, it's hard to— yeah, it's hard to give it up after a while.

It really is. Yeah.

Are the— do you have the whole team on Slack now? Or do you still— do you have to send like handwritten letters? Or what's the—

I'm doing handwritten, handwritten stuff, sticky notes still. I, you know, tried to get Slack's not working yet. That's been slightly hard to adopt. I've got my maintenance guy, I'm getting him on the software next week. Well, for the meantime, what I'm doing is I'm just taking the maintenance requests that I pick up on the phone.

Yeah.

I log them in the system. I print them out, and then I give it to him.

Oh yeah, you're just getting it in there to get.

I'm just getting it in there. Yeah, exactly. And then I'm like, cool. Did you do this thing? And he's like, yeah. And then I mark it as complete in the system. And like that's step one.

Yeah. Jane has learned.

It's really hard. And he's been here for 29 years.

Yeah, that's— yeah, that's gonna be a tough nut to crack.

Yeah.

Who are you? You whippersnapper, wet behind the ears?

Like, well, I mean, he, he knew my grandfather, you know, and he lives in the building too. So, you know, it's really a family-run operation. And, you know, there's— we have that sort of loyalty. We have what we like to call our lifers here. Yeah, they really are lifers.

They've lived in the building like for 20 years.

Yeah, we have tenants that have been here for over 20 years.

Holy moly.

Yeah.

Wow. Yeah, no wonder they're like fighting inflation because 20 years to 20— from 2000 to 2022 and then the recent run-up, like, yeah, on the business owner side.

And they haven't been raising rent, so it's like, uh, your rent is artificially Very low. I'm sorry. So, but we're trying to help people too. So.

That's good. That's good. Oh man, I, I don't know anymore. I, I mean, I said the other day, it just kind of came out. I was like trying to make a dent on the internet, but I've been doing that like, I don't know, since I was a kid. Yeah. So I don't know. I think it's one of those things where I just can't It's sort of built into me. I just, it's like my hobby, my entertainment, my job kind of thing.

Yeah.

So I always just like tinkering around on the internet and I think I've just gotten to this place where it's like, how do you create art using the internet? Not art on the internet, but operate between all these different things that we've played with over the years and like product management and being in software, being on the internet. And use that to create some type of weird different experience that's more artistic that people have never seen before. So I've been toying with some ideas and just playing around with some stuff on like distribution. Like this podcast is totally, it's just totally an experiment. I was just messing around and it was really like, okay, what's the thing that I can choose that I know I'll just keep doing? And then I wanted to use it as a way to reconnect with with people that I like, like yourself. I mean, we haven't talked in so long and it's like, this is the perfect opportunity to be like, let's take 30 minutes, an hour, let's chat, we'll throw it out there. If we've got some stuff we want to talk about, help the world and hell, if you got a vacancy, like we'll send some people your way.

Right.

Yeah. So by the way, I was gonna ask you, what product did you end up choosing for the software?

It's called AppFolio.

Okay, I've heard of it. Yeah, I ended up, this is kind of weird, but I ended up doing an M&A due diligence on one of these property management software things in the last month. So it's actually kind of fresh in my head, which is—

What did you look at?

Well, I can't talk about it because it's under NDA. Okay. Yeah, but yeah, but it's cool. I mean, the company had been around for a while and some really intense software and it's like every one of these industries, like these super niche industries have like this whole niche industry around the software too and just so custom built. So yeah, it's so cool. I mean, the internet's so big, it's like 5 billion people now and so many companies and like everyone's got a startup and everyone's got a VC firm now that it's like you can't keep up with it. Like there's just no way you just, You have no idea what's out there.

Yeah. I, when I was, you know, obviously through being in the industry, I was able to, you know, cut down on my list of vendors that I knew of. But even when I was interviewing them, because I'm not a property manager, you know, I could look at it from a product lens, you know, but that's not a property management lens, right? And so I think that it was a little bit harder for me. I wanted to get in and use it. And, you know, as I'm using it, I was like, okay, this is like, I was like, you know, does this load asynchronously? I was like getting really technical and I was like, but that doesn't matter.

Right.

Like, do property managers really care about that? And so I think I've, you know, struggled a little bit in that regard, you know, trying to figure that out. But we ended up, They were an accounting— they started out in accounting. That was sort of their core competency. And that was really attractive to me that their accounting side was built around property management.

Right.

And recurring payments and that sort of stuff. And that's really what we needed. And then having the online portal was huge. So, you know, there was a couple other players in there and You know, I'm sure that they all have their own bells and whistles. You know, we went with this one.

Yeah. No, good so far. Good so far. Yeah.

Yeah. Next, next step will be online leases, you know, and right, right now we're still doing paper leases.

Yeah. Just like, yeah, that's interesting. I mean, not just sign it online, but scroll through the whole thing and like purely digital. Digitize.

People expect it. People expect to be able to pay online. We've had tenants come here that are like, wait, you don't have online payments?

What's a check?

I don't have a checkbook. We've had people had to go get checkbooks. They don't even own checks.

Yeah.

So it's like crazy. Like, yeah, you gotta get a checkbook.

I mean, that's me though. Let's be honest. I like go to the bank maybe once a year. I'm like, hey, I need 3 checks. It was, it was really funny. I forget what it was. It was somewhere here in Tennessee. Somebody was like, oh yeah, I take checks. I'm like, wow. I mean, that's just like so insecure. I could just write a fake piece of paper. And I was like, do you have Venmo? And they're like, no, we take checks. And I was like, I don't know what to do. Do you take a credit card?

Yeah.

And then like I had to find some cash. And isn't that so funny? Like how things have changed over the last Since we were kids.

It's wild. People are afraid to use the technology too, and then when they do use it, they're just like, oh wow, this just makes my life so much even easier. Even here in the office, even, you know, people that are working here in the office, you know, my aunt who's, you know, doesn't want to use the new system, right? And now she's like dying for it because she sees us and how excited we are about it, how much automation it has around it.

Yeah.

She is just like, okay, like, why are you all so happy? Like, you know, tell me like what's going on. And, you know, we share where we're like, oh, well, someone paid this thing online and then it automatically attributed to, you know, the payment and, you know, and it just locked everything for us. And she's like, really? Because she's— she was the one that created the paper process.

Right. You know, so It's, that's so fun to hear. I mean, that's the stuff that I love where it's like you initially, I think it's like the block to change. I've done this so long that like, oh God, I'm gonna have to like learn this new thing and it's gonna be worse off. And then it's like magical on the other side. That's, I mean, that's the white whale I've been chasing my career is like, how do you just create that magic where it's obvious before you experience it.

Yeah.

Like, that's so hard. And I think to your point, it's— I used to call it method acting, but you have lived the life of your user now. And it's a completely different— like, figuring out what matters is the only thing that matters. And you were like, asynchronous, like architectural decisions doesn't matter. I just need timely payments that don't fail. And like a maintenance system that people remember the URL for and can log an issue.

Anything is better than what we were doing, literally anything. And, you know, someone that deeply cares about design too, right? You know, that was my first sort of trade.

You're a designer.

Yeah, that was me first before I got into product and I Even that, I'm just like, I don't, I just need a system that just like works and an all-in-one solution.

Yeah.

Because, you know, and, you know, there, I, you know, obviously my eye and, you know, you, I'm sure you see it too and in systems that you adopt and, you know, it's tedious, but if it works, at least at this point, I'm like, oh, thank God it just works.

So it's true. It's true, just reliability is such a big deal. Like, just let me do my thing and get out of my way. And I think so often it's just, let's just keep adding more features and it's gonna get better. And it's like, I've rarely seen the product team that removes features.

Yeah.

Because it's like, oh, I don't wanna give up that, that one MRR customer because we're backed by investors and we gotta grow to the moon and It just, well, it's also, it's probably tangled with other parts of the product too, right?

And unwinding things is just spaghetti. It's just awful.

Yep. So what do you, what do you think has been like the biggest or hardest transition? I mean, you've done, let's see, you've done design, product, property, SMB, high growth VC startups.

Yeah, it's the hardest transition. I thought the jump to design to product was a lot more challenging than I was anticipating.

Really?

It could be because I was doing everything. So at Breezeway, it was the last company that I was at, their designers and product, it was all all one person. So I had a Scrum team and it could have been too the scope of work that I had as well, which was the entire operations product. And then, you know, the team was, the engineering Scrum team was slightly understaffed. So that was a really tough position for me. So that was a pretty big jump. So I don't know if it was the actual role or not. It's interesting going from that to this though. I just have such a better grasp on how to attack problems now. It's like I see a problem and it's just like, okay.

Because of product?

Because of product. Because of being in product and having such really, really, really difficult problems to solve.

Yeah.

Like, okay, I mean, I just learned bookkeeping. If you told me 2 or 3 years ago that I was gonna learn bookkeeping and accounting, I would've told you you're crazy. But I'm like learning a whole new system. It took me about, it took me about 3 weeks, you know, and I'm not, I'm not, I'm not very good, but, you know, I can do it. I understand the basics of it.

Yeah.

You know, and I don't think I would've had that sort of confidence, right? If I hadn't had a previous position that pushed me to the ultimate. So I think the product management, going to product was pretty tough.

Yeah. Well, is it, I mean, I've joked about this, but I was like, what's the definition of product management? Because nobody can tell you and it's always different from everybody. And I'm like, I'll make it easy on you. The definition is everything. Yeah, everything, like, because that's the expectation, that's the requirements, like, do everything. And then what it really is, is like, you're a founder.

Yeah, you're based.

And so I think maybe that's why, as you jumped from being like a designer to like a mini founder, and then now when you are operating in like a founder role, it's like, oh, well, yeah, I mean, this isn't—

It feels the same. And now, you know, now I really do feel like I have the autonomy to make the decisions that I want to, right? And to do things the way that I want. And I know how to do it, or at least I know how to troubleshoot through things and work with the team. It's like I've got my resources, I've got my timelines, you know. All right, let's go. It feels so similar. It really does. Just a different industry. So I totally agree. It feels like I'm like a, like a, you know, Not a founder, but I'm in that operator type role.

Yeah, yeah, you've got, you've got Runway. You basically walked into Runway, but you're like operator. I mean, yeah, what's the, what's the transition period like? Is it like a year? Is your— was your mom the primary operator?

No, no. So, um, my, my, uh, my cousins here are the operators. My mom's been more of like an owner role. And so now I'm sort of taking a hybrid approach to that.

Yeah.

I'm like owner-operator. So my plan is to, um, you know, professionalize and stabilize for like one year. We were just basically in kind of like chaos triage mode, essentially. And just like, what do we do? Right? And then it was like, get all the units rented, let's get software. All right, now I gotta like tighten things up for the next year, and then I've gotta get rent roll. That's gonna take me like a year or 2, and then after that I'm looking to grow.

Do you know what— go ahead. Do you know what's interesting? I don't know if you've realized this, and I'm gonna say it and you tell me. Um, you, you've basically become private equity. What you just described, you've moved from venture capital to private equity and the process you just described is the exact process of private equity. The only difference is you didn't quote like raise a bunch of money and then use that money to do a buyout.

Yeah.

Essentially, you skipped that because it was your family and you just sort of like walked in. So you skipped the financing piece of it more or less. I mean, we won't get into it, but Yeah. And then you started, you looked at it and you're like, okay, we gotta do like da da da da da da da to optimize and then we're gonna grow.

That's exactly what it is.

Yeah, it's private equity and then you don't have an exit path or you don't, or you're not looking for an exit or whatever.

No, but that's exactly what I'm doing. You're 100% right. And, you know, trying to wrap my head around things and seeing what needs to be tightened up and what we're doing well and I'm evaluating everything all all the angles of the entire business. And then, you know, as I'm doing that, I'm also thinking about the future and where it is that we're going and, you know, the growth or a potential sale. Like, I, you know, I'm not exactly sure.

Yeah.

But well, either way, nothing can be sort of explored until we understand like what it is that we actually have right now. And I don't even know what it is. I'm still trying to figure that out, you know, and I think the future is going to be growth and that's really what I'm excited about and why I made this jump. Like, yeah, the property management stuff is okay, but like, I'm really excited about leveraging the asset, maybe like buying another building and, you know, doing what we do well, which is— Owning property and being a property manager at the same time.

Yeah.

Not, not being a property manager, that's different.

Yeah, right.

Property managers sometimes have to deal with owners, right? We don't have to do that here. So that, that, that's a challenge for today's property managers, right? But if you're in this position, it's slightly different. So I'm hoping to do that, but we'll see.

It's really interesting. I agree with you. I mean, the fact that what you're trying to do is really get a handle on like the valuation of your asset and like whether the levers that you can pull on, but I think it's really smart. I mean, there's only so much planet Earth to go around and everybody needs, I mean, it's oxygen, water, food, shelter. And so it's not going anywhere. Sure, price volatility, but Yeah, it's interesting. I mean, I've kind of stayed away from the whole world for a long time, but we ended up buying our first house a couple of years ago, like right when COVID hit and ended up doing like full renovation, which has been like running a startup while running startups, multiple startups, which has been like, like stick your finger in the light socket and fry yourself for a couple of years and that's what it feels like.

Yeah.

But yeah, I think it's super interesting because, for example, the banks as well, like they look at that type of asset versus, let's say, a stock or a business which can be more volatile, go up and down. Businesses can go bankrupt. But I don't know if you know that on the land, you don't have to talk about it, but it's like I see you being this like vertically integrated real estate private equity owner-operator. And I think that that gives you, it gives you a ton of really interesting leeway. Like, you know, I wouldn't be surprised if you get to a point where you start creating your own very simple product, like software product to help you run your thing. And you basically, because you could write the spec, you could design a couple wires and then you could just like throw it over to a simple team to just build it out and then you're using your own product and you're getting rid of all the garbage that you don't want to manage all of this stuff. And then like you would end up running both the real estate side and the software side. So you have exposure to both internet growth and that recurring revenue stream. And I think this is me, I think the business model of the future is this bootstrap business model where you have 2 things. You've got the cash generation engine and then you've got the capital allocation flywheel, right? And they feed each other and that's what you do with the excess cash, right? And then so you just start building your fortress, so to speak. So yeah, I think you're gonna have a blast, dude. I think the next like 20 years are gonna be kind of fun, not without its challenges or gray hairs, but—

Right.

Yeah, to folks like you and me, it's just, it's like they're our video game, Right?

It is. It really is. I come in, I'm like, oh, let's see what I can do today. Like, you know, my, my, on the AppFolio, I was able to get 35% of people, 35% adoption to the tenant portal within the first day.

Of your tenants or your team?

Of my current tenants.

Oh, wow. Out of 150, you got 35%?

At 115, yeah, 35%. So it was huge. And now I just told everyone, I was like, if we get this up to 75%, we have this like Italian restaurant.

Pizza party.

I was like, yeah, I was like, yeah, I was like, we'll go to Fiorello.

Book it. Everyone gets a chicken parm. Chicken parm on the house. That's amazing. Yeah, you're, I mean, you're doing products, you're trying to move the metric, man.

Yeah, that's it. Yeah, it's literally, I'm, I'm running it like a product manager, 1000%.

I mean, I, I gotta tell you, I think it's gonna— you were like, oh, it's like a year, year and a half. Like, you might be 9 months in and be like, Jesus, okay, what do I do now?

Because that's what I'm afraid of. Yeah, it's real fear that I have that, is this enough for me? Uh, and it's like You know, am I gonna end up going back to product? Like, it's possible.

Like, you take a, you take a part-time gig just to like get rid of the nervousness.

Yeah, I thought about that, Sean. I, I kid you not, I've thought about that. Um, you know, I've thought about maybe advising or maybe taking up a small like contract, but contracting PM, I feel like that would be really hard. Maybe I could contract as a designer, but I don't really wanna do that. I'm kind of tired of the design world.

Yeah.

Um, but yeah, like if I had this and it's like I oversee everything here and then You know, do some advising or maybe build my own thing on the side. There's another world here for sure because I'm not gonna be the only operator here. I just need to make sure that things are, you know, we've got our roadmap, we've got, you know, things are moving in a certain direction and I'm overseeing it, but I'm not gonna be a daily operator forever.

Yeah.

So that's the plan. Honestly, I just don't know what the next thing is.

I think you'll get to the point. It's basically, I mean, you might just have to take like a week vacation and then just let all of the stuff like the sediment in the water settle and then have that quiet place and just see what that inner, that inner pull, that inner voice like takes you to. Because that's why I say, I mean, you're a creator, right? Like you're a builder, I think, and you've got the skill, right? You've got the design, you've got the product, you can do the business side. I think, I think you should just let that creativity just sort of see where it takes you on your own. If you've got that extra cycle time to just play, I mean, just throw open Figma and like mess around with a couple wires or something, right? And I bet you'll end up with something kind of rad. Like, what's property management software in the metaverse look like? Like, let's go 3D, baby. See, there you go.

I like it. Yeah, that'd be pretty sweet.

Yep, that's cool. I like it. So what's, uh, what's on the docket this weekend? You got anything fun going on? What's the— what's the life side like instead of the work side? How's that all going?

Oh, life. I mean, I'm dating, um, this girl Rosie. Her and I were actually— we talked about vacation. We are headed to Spain September 15th.

Nice. Where in Spain are you going?

Going to Madrid for 3 nights, then we're taking a train down to Granada, southern Spain, spending 2 nights there, and then a train to Sevilla, 2 nights there, and then back up to Madrid for another 2 nights. So we're doing a nice little loop and then back, back home to Boston.

I love that. The trains throughout Europe is like such a romantic proposition. I'm, I'm so about that versus like the subway in America, you know. It's like, it's like just the brake dust versus like the countryside in, in southern—

Have you, Sean, have you ever been to Boston? And have you ever been on the T if you have been to Boston?

I have— I haven't been on the T, but I have been to Boston. Um, so my partner Mia, she was going to Harvard for a little bit. And we ended up doing a campus visit. And it was actually one of the most— okay, I'll tell you a little personal story. It was one of the most incredible art experiences I've ever had. So this picture, this one right here, it's a print. It's not a real Jackson Pollock. I don't have that kind of money floating around. But inside the Harvard Art Museums, I didn't know what to expect. I'm just like, oh, just some random, like, little tiny, like, What I, I just don't realize these things. It's like Harvard. I just, it's like some community college, you know what I mean? And they have, they happen to have like this little room full of like art from the kids or something. I don't know why I think this, but this is my mindset walking into this place. And it's like free with our student ID. And then I guess they have 3 different museums, which is why they call it art museums, not museum. So we walk in. And I walk into this room and I'm, I'm like kind of, you know, like not paying attention. And then I'm like struck. It like hits me in the face. I'm surrounded by masters. Like, here's a self-portrait of Van Gogh. Like, here's a Monet over here. And then here's like this incredible Jackson Pollock. And I'm— and then here's a Rodin. And I'm just like— and I was never— I don't know, I guess I know a little bit, but I've never been like this huge art aficionado. But for some reason, you just kind of soak it up over the years. And for some reason, there was this really long Jackson Pollock painting and I just, everything clicked. Like I stood in front of it for like 30 minutes and I was just like, oh my God, like I get it. I get it. All this stuff.

Yeah. What was it? What helped me understand it?

I saw the craftsmanship. I saw from a creator perspective, from an artist perspective, I saw, you know, when you hear about these artists, like musicians, artists, painters, actors, Yeah. They, they aren't creating their thing. They're like a channel or a vessel upon which the universe uses them as the paintbrush, so to speak. And I could see that channeling come through his paint drip technique because he had layered it with different colors at different, um, like velocities, but also depth, and then spacing without— within the canvas. And it was, it was like imperfectly perfect. And I realized if I tried to do it, it just looked like I dumped out garbage onto a piece of canvas.

Right. So you were able to appreciate and figure out what this person had done based on your background.

And as another step further, so I was deep in this world of studying connectomics, which the connectome is the brain and nervous system of all animals, humans, everything down to like a 300-neuron worm. And I was struck because I was like, my God, this is like Connectome on canvas. This is the universe. This is dark energy. This is a fractal. This is everything that he just put on a, on a canvas. And I've even contacted the museum afterwards and like, can I get a print of this? Can I even get a high-res photo? They are so locked down about the rights to that painting that the only thing you will find online is this tiny, like, 300 by 300 pixel resolution image. There is nothing out there, and I ended up getting a picture of it. So it's like on my Instagram, and it's stored, and I look at it. And so, like she got me this one as a present. But yeah, for me, it was just so needless to say, like that's my like like Boston story. So I have a really special place in my mind and my heart for that area of the United States. That's great.

That's excellent. Yeah, well, you know, if you want to come back and check out more art, you're gonna have to reach out.

Yeah, dude, for sure. I want to do a little road show like later this year and hit up the East Coast. I got to go to New York, see some friends, DC. Yeah, um, need to hit up Boston. Yeah, definitely sit down, grab some grub and coffee or something and talk shop or just Do jump high fives or something.

What's next for you, Sean?

I don't know. I'm kind of just, I'm helping a couple of people do their thing, which is really rad. I enjoy it. It's good people. I love who they are. I'm kind of just doing this exploratory phase with the extra time I have, like this podcast. I mean, it's wild. Like you said, you can't turn off the product brain. So In 3 weeks, I think the number of unique IP addresses hitting this podcast RSS feed went from 0 to 4,000. So the growth rate is like insane every day and every week. So it's like, okay, just keep investing in growth. Yeah, see what it does. It's resonating. So something is going and I enjoy doing it. So it's like, okay, let's keep doing it.

But Yeah, I get to catch up with old faces at the same time.

Exactly. It's like win-win-win-win for me all the way around. So yeah, I think I'll probably keep doing that and I just like building stuff on the internet. I like building technology that helps people. So I know I'm gonna just continue to do that and I like hanging out with good folks to build stuff. So, you know, here's my ultimate dream, right? Like all the people in my network, I somehow find a way to get them all together to create the ultimate Transformer Voltron product, you know what I mean? Like the product of products. And, and then we release it onto the world and it's like Bill and Ted's Excellent Adventure where one song changes the world, you know?

Yeah, that'd be excellent. Yeah, that'd be cool.

Far out, dude. Yeah, buddy. Yeah, man. So something along those lines. I don't know. I think it's have fun, do good work and work with people you like and good things happen.

I think, yeah, that makes sense. We'll see if I miss it. I think I'm headed in the right direction. I like, you know, not working for VCs.

Yeah, it's not easy.

Different. Yeah, it's definitely different. You know, I like being my own boss. So that's nice.

I had this one thing we were growing. I don't know, we were growing at like the 95th percentile and the message from the board came down like you need to grow 6x in one quarter. And I was like, you do realize that that's not possible, right? Like nothing, nothing grows at that rate, like 6x in a single quarter at a completely different slope, like mostly like this, which is already 95th percentile. And then you want to go straight vertical. It's like, I mean, I get it. I want to, I want a billion dollars in the bank and like go make my friend's movie, but I'm not doing that right now. So it's just weird.

Right.

It's a weird Yeah, I don't know.

Yeah, I'm happy with the small business thing though. I really am. It's good for at least right now. We'll see what happens though, you know. I'm sure I'm gonna have the itch that like the creator stuff, that's what I sort of realized the other day is that all the tasks here, everything, it's the same. It's just creating a process and tightening that thing up and that's it. You're not, I'm not creating anything. Unless I get into growth mode, which is the most exciting thing for me.

Yeah.

If I end up getting into building, which would be really cool, I could get my contractor's license and go in that direction.

Interesting. You're thinking like acquiring multifamily and then reno and then do more rental?

Sure. Maybe.

Yeah. I don't know. You need— you know what would be fun? Not that you would ever make business decisions this way, but to put one of those like Wheel of Fortune things with different ideas and then just spin it and then whatever it lands on and just see how that feels like, oh, now I gotta go do that. Like, oh, why not? That does feel cool.

It's not a bad idea, honestly. I don't know how else I'm gonna pick. So it's either deep thought or Sean's Wheel of Fun.

Wheel of Fun and Fortune. Just one legal disclaimer I have there is that Past performance is no indication of future performance and I hold no liability about what happens from your wheel of fun and fortune.

Fair enough.

But I'm happy to help. I'm happy to help, man. Yeah, just be— my one advice is be very careful about the contractors because we've been through some very rough situations. Oh yeah, right.

Yeah, it's no joke. You gotta keep your eye on them. Big time.

Absolutely.

It's hard to find workers too. I'm surprised you were able to.

Oh, it was tough because pandemic, it was like, one, hard to get people to come out. You've got to be really safe. 2, supply chain shortage. You can't get anything. I mean, we ordered some new cabinets and it took 9, 6, 9 months for them to show up. I mean, we Here's the reality. It was, yeah, it was 2 years without a kitchen because we had a bunch of issues. We had to replace every appliance, the water heater, the floor, the walls, like the entire kitchen, take out a wall. We, I, we were doing dishes by hand in like a little tiny sink off to the side for 2 years.

Yeah.

We just got that done in like I don't know, over the summer and it's like, wow, okay, what's a dishwasher?

Lead time is crazy right now for cabinetry. It's wild.

Yeah, it's nuts.

Especially if you got custom stuff too and things are just expensive and help is hard to find. Yeah, I'm struggling with that right now. That's a hard reality I'm facing, you know, like fixing things and stuff. So Yeah.

Well, just my advice to you is don't live in it while you do it. That was tough.

Fair enough.

Yeah. But you know, like you can do that, you could do anything like do a couple startups and a home reno at the same time. Boy, that'll stretch you. That's like David Goggins, man. Like I was sweating.

Yeah. It's funny, the startup things is, it's, I feel I feel like now I'm like catching my breath right now and I feel like I, I think I will be ready to, to do something again soon. Right now I'm def— definitely just like catching, catching my breath.

Sustainable. Yeah, it's smart. I think it's really smart because burnout will sneak up on you and it'll just, it'll crush you. It'll crush you.

Has that ever happened? Has it ever happened to you?

Oh, a couple times. I put myself in the hospital when I was younger a couple times. Wow. And then I've also experienced extreme level after the last couple years, like Mood changes. I mean, you just can't help it. It's like everything's frustrating, you know? And so you just, yeah, this, I kind of reset the decks on my 41st birthday and over the summer and kind of started fresh from scratch on everything. And yeah, like, yeah, it's, it's definitely—

That's where I was at my, my, the last PM job. And, you know, I've been using this job to kind of just, you know, reset and kind of figure out what I wanna do and, and, and do all this and It's been good. It's, it's a mental shift is needed sometimes.

Yeah. Yeah. And you're like happier, you do better work and you, it ends up, it feels less hard, but you end up doing the same or better or faster quality work, which is weird.

Yeah.

It's like an inverse relationship.

Yeah. Yeah. It's so weird. I'm, I'm, I'm slightly stressed, but it's in a different way now.

It's, uh, the owner stress kind of thing.

Yeah. Yeah. Yeah. It's stress in a different way. I can't explain it.

Like, if I don't do it, it doesn't get done, or if I don't like push on it, it won't happen kind of thing. Is it that?

Yeah, yeah, something, something like that. Um, versus maybe before I had to have like, um, yeah, I just, I just felt like I was doing a bazillion things at once as a PM and it was just, It was just chaos. And then— True.

Just proves your point.

It proves your point. Every time you interview a former PM, everyone says the same thing.

Everything chaos. Yeah. Yeah. Your job is to keep—

It's like, it's slightly like controlled now. I feel like I'm, I'm, I can see it and I'm like, oh no, no, no, we're not going down there. We're not going down there. I'm like, I got everyone on Notion. I'm like, write your tasks down. We're gonna lay it all out. There's no deadlines. Yeah, like, this is easy. Yeah, we're easy living here.

Yeah. Yep. Yeah, it's time matter. It isn't like an extreme sprint from the moment you wake up until the moment you go to bed.

And yeah, like, yeah, tenant, tenant screaming something. And, you know, I see my staff getting upset or something. Don't worry about it. Deal with it next week.

Yeah, we're good.

It's fine. We're— the building's still here. Yeah, they'll be fine. Yeah, it's like I never had that. So now I'm just trying to create an environment that's like super chill, really calm. It's like, no, we do work. We do like fantastic work. It's like buttoned up. It's precise, it's accurate, we're responsive, but we're chill. When we do the things that we do, it's done well, but we do it on our own time.

Yeah, I think it's— yeah, I love that because it's that metaphor, like lay every brick perfectly and then you don't have to go back and fix the wall at the end.

Exactly. Yeah. Yep.

Yeah, and it's slow and steady wins the race. And don't worry so much about like getting all the bricks out of the, out of the truck and just throwing them on top of each other, right? Like fall over if someone like breathes on it wrong.

Right. And I'm like, hey, hey, chill, we're laying, we're laying bricks here one by one. We're laying bricks.

We're gonna go get some pizza and some chicken parm.

Right.

I love it. Oh, that's great. So are you, are you rocking the Whoop? I think I saw the Whoop on your—

Sure am. Yeah.

The Whoop. Is that what version is that? 3.0 or 4?

Absolutely. Come on now.

Absolutely. You know me.

Yeah, this is 3.0. What do you have?

Oh, I'm doing the Apple Watch, you know.

Oh, I got that on my left wrist.

Do you have an Oura Ring though at the same time? All 3?

I, I should.

Okay.

Do I?

I need to, I need to intro you to my buddy Antoine. He was my first guest. He's a rad dude. He's in DC, but he's been doing research in like wearables and testing like everything for years and years and years. Like even the Snapchat Spectacles, the Oura Ring comes very highly recommended from a number of people that I know that have used it really well. Like sleep tracking, very, very good. Doesn't give you the EMF tingles like some people that have some sensitivity to it or can feel it. I'm thinking about doing it too, but I like the Apple Watch because one reason, for the better part of 20 years, I wanted to just like go running or work out without wires or a device or a phone or a Discman back in the day. And being able to pop in like AirPods plus this and go running.

Oh yeah.

It's like finally freedom, you know? And to me, that was like the thing I had been waiting for 20 years. So thanks, Apple. So that's— and then the step tracking and everything is rad, and the notifications become a little ridiculous, but whatever.

You know, the, the, the readiness score, that's what a lot of them are— have. I think Fitbit's got it. That's what it's all about. I feel like it's only a matter of time before Apple has A readiness, right? Your, your, your body is ready to take on strain or activity, whatever, whatever these companies wanna call it. It's all the same stuff, right?

Is it? But does it work? Do you, what are your thoughts on the readiness thing from your experience?

Yeah. Yeah. It, I mean, it's definitely accurate. I mean, if I am, go out the night before drinking, it's the next day, it's like, you should, you should not exercise.

You need to recover. Netflix and chill, man. Like literally chill.

Yeah, it's in the, it's green, yellow, and red bars. And like if you have a few drinks, at least now I'm gonna be 40 soon and it's like I have a couple drinks and it's like it's definitely gonna be red the day.

See you next week. Sorry about your beer.

But I use it now. I use it as my alarm. It vibrates and so I can give it a range because it's, it tracks my sleep. So it knows, you know, if I hit my sleep goal, wake me up within a certain range.

Right.

I, I, I love that. It's more of like supposed to be more natural, but you know, if I have to wake up at a, a specific time, I can set that. But yeah, you know, I, I'm liking it. So.

Do you, do you feel like the sleep and the rest and the recovery thing, do you feel like those Devices have made a positive impact on your health, or is it just kind of like data?

I think it's just, I think it's just data. Just knowing is really helpful. I think it's really hard to change human behavior. I think it, it can in the beginning. It's like, you know, it's, it's the novelty factor. Yeah, the novelty factor, you know, whatever you wanna call it. It's like something new and then that sort of wears off.

Yeah.

And then I personally like to understand the data just like I do with my Apple Watch too. I do the same thing. At, at first I was comparing them after every single workout.

Yeah.

I was like, oh, I was like, this one's like not, not 100 cal, it's 100 calories less. I'm like, that's bullshit. I'm like, I was like, ah, like I wanna like edit the calories on this one, you know?

Yeah.

But at the end of the day, it's like generally the same.

Interesting. Yeah, I've had a slightly different experience.

I think it's—

I started it just to track. I mean, after like such a stressful couple years, the reason I actually bought it was because I was worried about my heart. I hadn't had any issues, but I just, I just wanted to make sure, like that, you know, I had something that could alert me if there was. And so I ended up on my birthday, like when I reset everything, I ended up get like a full battery of like health tests, like everything across the board to see where I was. Luckily, like knock on wood, I'm a pretty healthy dude and everything was good. But that was the catalyst that made me buy the Apple Watch again. 'Cause I, I had one in the beginning. And then I found—

Knowing, just knowing.

Yeah, it was like a, I want to get alerted essentially if there's something that there is an issue. But then it became, it actually started to increase, you know, I paid more attention to it. So I started getting more activity. And then over the last like month or 2, 2 months, I've found that I'm actually, I increased my output physically by 50 to 100%.

Wow.

Just as a result of me tracking it and then keeping up with the streaks and then just like tracking walks with the dog, going running, lifting and exercising. So it was more of this like gamification, like streaks create boosts kind of thing.

Yeah.

Yeah. And so it's definitely been a positive, positive impact. But you gotta be careful 'cause the stuff can just like turn into an obsession and you just go overboard.

Like Yeah.

Gotta, but like 99, I gotta get to 100. But yeah, I mean, it's at the end of the day, it's like whatever.

I wish, I wish it, I really wish it would influence me a little bit more, especially right now. You know, I, I sold my place, I just moved. I up, I, it's like I have a whole new life right now. So it's been a little bit rocky on the, on the workout side of things. And I wanted to be, I just wanted to just like shout at me and be like, Dave, Get your ass to the fucking gym.

Do you think that would work for you? For a certain personality type, would that actually work for you, or it'd be like, go, go pound sand, get out of here, like throw it against the wall?

Probably. I mean, I don't know, I'd be like, I know that I have to do something. Just getting motivated again has been, you know, a struggle, I guess.

What if it just like whispered like, hey, Hey Dave, it's 4:30. What are you doing? Get up.

I'd be like, Sean, you're annoying me. Go, go do something.

Get out of my face, dude.

Right.

It's like that annoying little brother that like pops his head into the room. It's like, get out of my room, man. That's amazing. Well, cool, dude. Um, oh shoot, like we've been going for an hour. I, uh, I actually have to run to like my next one. Um, this has been, this has been rad, dude. I wanna— let's stay in touch. And then if I, if I get out, um, I want to, I wanna get out to the East Coast. I wonder if I could take a train over or something. I'll figure something out. We should like get together. No worries.

If not, we'll just stay, stay in touch on, on the, on the web, on the internet and the interwebs.

The internets. Yeah. Let me know how Spain goes too. I want to, I want to see some pictures and stuff. We're, we're headed out of, out of town next week, so that should be fun.

All right, good. So you're taking a break too?

Yeah, taking, taking a week. Gonna just like reset. Walt Disney World.

Oh, excellent.

Yeah, little magic, man, you know, pure escape.

Well, you have a fun time. There, and we'll definitely, definitely stay in touch. This is awesome. Really good. Really good to chat, catch up with you, man.

Yeah, for sure. And I'll— so I'll upload this, be private. You let me know if anything you wanna like cut out or whatever, and I can just splice it out. And yeah, cool, dude. All right, brother. We'll talk to you later. Have a great weekend.

See ya. You too. Bye.

Bye.