#23 - Disney for Dogs

Who's that good looking boy? We're gonna be opening our first bar box for my dog, Russian. I believe the box was $22 for a month in subscription, so let's see what's inside. I made my first million by trying to make a Disney for dogs.

I think when you build a big business like we have now, you wanna try to come up with these glorious stories about how insightful you were. It wasn't really a big deal. I think it was kind of like the shitty idea of the day. We definitely didn't think of you a big business.

I think what we saw pretty quickly was that he was working. You guys are doing somewhere on the order of $250 million in revenue annually. $5 million is not a month. $10 million.

$20 million. $50 million. $250 million. One or two people in a bedroom actually put the rest of these giant multi-million dollar companies because you have creativity and you have nothing to lose.

Add another zero to that price, buddy. Add two more zero. Hi. First person.

New media. Every week we sit down with self-made millionaires and ask them, how did you do it? I didn't start a podcast. I started my own personal business school.

And the teachers are the successful entrepreneurs behind the biggest brands and businesses that we find today. I wanted to know the real stories, all the details. Like, how did you get your first hundred customers? What did it feel like in a shit?

I asked them, how'd you spend your money now that you're rich? And what would you do if you were starting over from scratch again? If you're like me and you want to own your own business, instead of living a nine to five job, this is the podcast for you. The hustle presents my first million.

We're here. It's nice to meet you. Thank you. I'm excited to talk to you.

So let's tell the people what it is that you did and what you've built. So tell us, how did you make your first million? I made my first million by trying to make it Disney for dogs. Disney for dogs.

I think that was always kind of like the idea. I made my co-founders and we love our dogs and we wanted to make cool stuff for them. And so that was the premise. Is that like, are you a massive Disney fan?

What do you like about Disney? I think any sane person is a massive Disney fan. I think from a business point of view, though, what's fascinating with them is that it's a little bit tough to pick what they are. They make toys, they make theme products, they make content, they make all these different things.

And so I think what was intriguing for a slightly kind of neurotic entrepreneur like myself was this idea that you could anger your business as not in a product that you were making, but in a promise or a problem you were solving for your customer. And we wanted to make our dogs happy. Were you a dog person on a scale of one to crazy dog person? Like I have a dog.

I'm crazy about my dog. I see people with dog park who are like, they own four dogs. They eat off the same plate type of things. Give me a sense of the spectrum.

Where are you at just before you start this business? Was that your life passion or? No, I think maybe appropriate, you know, Monday morning confession. I think I'm a little bit with you.

I love my dog. My dog is my little child and I would do anything for her. I'm not necessarily somebody who would have a hundred dogs at home. And so I think in many ways, it's the same way that I have a kid.

I love my son, but it's not that I'm going like, you whoo, there's like 20 babies on the plane. So I think for me, we obviously in the company have a lot of different kind of permutations of crazy dog people. I think the craziness for me is in the togetherness between me and my dog. But before that, you know, I guess like my wife and I was foster parents for a lot of dogs.

And so we would help dogs from the south where there's a lot of kill shelters up to New York and we would then host them for a few weeks until they could find an F.I. ever home. And so I guess in that way, I probably skew more into somebody who loves dogs than like the average person. But you know, like I'm not the one who kind of have like pictures of dogs everywhere and a bone in my key chain.

So given that, where did the initial idea come from? Where were you? What were you doing before this? I wish you didn't know where I was.

Because that's actually an embarrassing story. Let's start with the embarrassing story for sure. So the headline was that I was the first time I ever met my founder was waking up in a hot shaped bed on a cruise ship in my boxers. And that sounds not as appropriate.

It's a little bit less on a private story as it might sound. So first we're three co-founders, Matt Callie and I. And Matt and I were both kind of working in kind of like in between type of roles. We both built startups before and exited them doing our next thing.

So Matt was at kind of like an incubator type place called Dog Patch Lapse. So he was running that in New York and I had started a kind of halfway home for Entrepreneurist called Pre-Hype. And we were on a summit series conference. And so many years ago, they had one on a big cruise ship.

Yeah, I remember that. And so if you were a little bit of a cheapskate, you would pick the cheap ticket which would like randomly being paired with somebody else. And so Matt and I were randomly paired and I checked into the cabin before he did and they have taken this hot shaped bed and they pushed it apart because it's too random people. I thought we had Lara support them back together.

So I put them back together and kind of read it the bed and then I went up to get a drink I guess and then I got back pretty late and Matt had gone to bed earlier. And so literally the first time I ever shake this guy's hand and we're like in this kind of awkward under one dew rake. Hello my name is Henry. In many ways, I think it's formed the DNA of the company in the center.

We then just sat and talked for a long time and then we figure out that while we're very different people, you know, I'm from Copenhagen and East from Iowa. We shared a lot of the same values and I think had in many ways tried to build like fast growing venture businesses before and was a little bit fatigued around that. So that's kind of like how the idea came around. We were just sitting in the bowling.

So it was during that first cruise that you guys actually came up with the idea or you had the idea. To be more concrete, I think what I tend to do with the stuff I do is I find somebody that I think I want to hang with for a long time and then we just organized I think it was Friday rainstorms and then on the second Friday or just a little bit. Well, I love my talk. At that time I was fostering and Matt has a duckled hugo that he's obsessed with and like real obsessed as an insane crazy dog parent of that.

It's a big great dame and it was tough to find good stuff for his dog in New York City. So we're like, maybe we can make like one of these boxes and do that. And what was you know the inspiration was there another subscription box that was doing well and we should tell people what it is. We'll give the people those sort of 60 seconds.

What is the product high level of review of the company and then we'll go back to the story. So bark is the company that's trying to make dogs happy. Dogs and their people. We have a number of different products and services.

I like these like dogs and their people. They're people that are dogs. Well, they come first now. So the product that we're best known for is either a bark box or super sure those are two boxes of these subscription boxes with treats and toys and juice that gets sent their themed.

So there's something funny for both the dog and their parents. We also now do dental products. And so we've kind of like branched out from being kind of like a one product company. And so the core thing that kind of helped you guys break through was the 20ish bucks a month for the bark box and to give people a sense.

I think the last numbers I saw was like you guys are doing somewhere on the order of 250 million in revenue annually now. So built a very big business off of this. Okay. So that's the about the company.

I want to go right back to where we were. So what boxes were you looking at at the time that you're like, Hey, could we do this for dogs? So the only box that really wasn't around at the time was Birchbox. So it was out of New York and I knew off Katya and Haley was kind of like in the area and in kind of like the community.

And so we were like, Hey, maybe there's like a Birchbox ish kind of thing for dogs, but where instead of getting what we might cannot do more thematic and stuff like that. And so practically I wanted to respect full of them. So I cold emailed them and said, Hey, I met them a few times. I wasn't completely cold.

Just saying, Hey, we're thinking about doing this thing for dogs. We think of you have a little thing, but I want to be respectful and combine. Tell us what you're doing. And if we can at all like do something together as in, if you wanted to be advisors to a business, we'd love to have you.

And so they were incredibly helpful. Like they didn't take their advisor shares, but like they did kind of help us out with advice on what pick pack and logistic partner we should have. And I'm very grateful for all the help that they provided. Amazing.

Okay. So decide to start this thing. And when you were doing this, what was the second best idea that you guys were brave? What was the name of your co-founder?

I met me, Gary and Carly. So I think it was Matt at the time that you met in the heart shaped head. So what was the second best idea you guys had? You know what?

I don't think that was one. I think when you build a big business like we have now, you want to try to come up with these glorious stories about like how insightful you were. It wasn't really a big deal. Like I think it was kind of like the least shitty idea of the day.

And it was a Friday and then over the weekend I would build the prototype and WordPress. And it was kind of like shit. I think it even calls something really stupid like doggy-backy. So I would send that to Matt and we would both kind of start to go like we should see people like it.

And so then next week when we met people they were saying, well, what do you think of entrepreneurs doing? What do you think of what do you work on? I was like, I'm working with this thing. And Matt started by somebody saying, hey, you should sign up when you're ready.

And he was like, well, I have to square my phone. I can just take a credit card right now. Let's see if this is polite. Exactly right.

And so I think we got to like 70 accounts and then we're like holy moly now we actually have to ship something. And so at the time Carly was at started Uber in New York. And so she was like running around and signing up and she was hanging a lot in dark patch laps. And so we were like, hey, maybe we should get somebody to help us.

We have to make some boxes. So we learned her into a little three people and then she really just ran with it. And so Carly is this amazing person who is very efficient of getting everything done. And so I kind of blinked twice and suddenly there was boxes appearing in front of us.

And so this is how we were just packing the boxes ourselves. Carly would run down and get some product and we got the brown boxes you can buy in the most office and then we started packing and I'm just like, dang, so I brought happy holidays with two L's and like help 70 boxes and they were shouting at me. And then we're kind of off. Right.

You know, it never really was like, let's start a company. It was more like, let's just try to kind of stumble ourselves into this. Yeah, I was listening to this talk by the guy who started Stripe, Patrick Allison, and he was saying, when you're actually out there doing the thing, there's no like cinematic soundtrack happening behind you, showing how epic this is that you're doing and that this is the moment and all this stuff. It's like, it felt very normal, almost mundane for a long period of time.

And it wasn't clear that this was going to be a big thing. It wasn't clear that these decisions were important and all this stuff. I think we definitely didn't think it would be a big business, right? You know, we were like, we should never raise a venture.

We should do a sale that would be a side-side hustle and all those things. I think what we saw pretty quickly was that it was working. And in many ways, I feel now that I've started a few things. Success kind of like is somewhat obvious pretty quickly if you have a product that customers really care about.

And it's a little bit more like the unsuccessful stuff that's a little bit more pick. So we put this product online and like it wasn't like obviously like we skyrocket the next day, but like it was a real traction, like you could feel that people were into it. So what happened to you? Those first 70 customers, those are friends and friends of friends basically.

Yeah, like people we ran to meet. Yeah. So what were the next 700 people? How did you get that next level of traction?

Yeah, next time again, like very basic. We had no wordpress based website and we were fortunate that we kind of got in the early Facebook days. We have a product that is very suited for Facebook, right? Because we can show pictures of dogs.

So the next 1000 customers were early Facebook ads and kind of like Instagram kind of stuff. Again, like we were one of the few ones. I think we were one of the very early brands that really kind of leaned into it. I have a background at MTV and I think in many ways one of the takeaways from there was that when making content or talking to customers, if you can kind of talk to the lifestyle of what you're doing instead of kind of like the thing, then it's easier for people to associate with an easy for them to want to share it.

Give us an example. What does that mean? So you're not talking about your product. You're talking about the lifestyle.

What is it? Give me a different example besides your own. I think our content would be more about like what do you do if your dog doesn't like your boyfriend than it was about like, five way to clean the paw of your dog. And I think everything, I think, tend to be pretty utilitarian because most product owners are entrepreneurs are like, well, I need to sell my stuff and so I need to tell you why this is amazing.

I think in many ways what we were trying to do was just to tap into this dog having a steam. And again, like we didn't think it would be that big. So in the other days we were just posting stuff that we thought was funny and we thought, you know, we need to pretend that we were dog controlling people on Facebook, right. And so we would go into political forms and go like, from a dog's point of view, I think that.

And so all those different things kind of like, I think just created an atmosphere of playfulness and I think in many ways that's what we've been relying on ever since. Yeah. And so what you said were MTV before, we don't MTV. Yeah, my background is kind of missing.

I thought I wanted to be a radio journalist and I started out at BBC and radio journalism and then got offered to, did a radio documentary about MTV and then got to hang there. And then what's kind of funny was I was then sitting writing my final thesis and everybody at work thought I was working really hard because I didn't have computer homes so I would write my final thesis at work. And so the bosses would come up like, you know, when they were going home and I would still be there and they'll ask about it. Now I was a super nerd back when I was young and this is like when the internet was just materializing, right.

So this is like 90s. And so they figured that out and said they were asking, can you help us build a product or TV show about like this internet? This is before we had a website and doing it. And I was like, okay, I'm up with this idea, which now is pretty stupid but obvious but it's kind of a UGC but if to show that on air is really difficult because like the visual clash and so I had to basically write this code that would take a camera and then kind of make the percent of look like she was a flash animation and then show her in the same environment and the other thing.

So I came up to the idea of my boss, he was like, oh, interesting but and then he pitched a little bit around everybody thought it was a video. I cut it because it ran through Windows 95 computer and the engineers like there will never be Windows 95 computer running like a live TV show on the channel. So I got a little bit stubborn and figured out that all the offices was wired for broadcast. And so I bribed the transmission engineer and I went live at two in the morning from my studio without permission.

And so back in the days that didn't kind of land you in jail at MTV. So the next morning everybody's calling and like what the show I've never seen the show before. It's amazing. We're going to see it and everybody in terms like I haven't heard about it.

So just hijacked MTV. It's a good morning. And so the boss at the time which is this wonderful guy called Brent Hansen, new ceiling guy. He basically emailed me and said, Henry, question mark and I replied back.

I don't know anything about it. He goes like, dude, don't ever do that again. But I want the show on here. And so I went from being a producer to basically run product development for old channels outside the US and I did that for eight years or so and MTV games and a lot of like, you know, it's a message TV and a lot of the stuff kind of outside.

Right. That's pretty cool. I think MTV especially during that era was so influential. It was like that was the pulse of pop culture and music and sort of that intersection between the two.

And so I think that would help refine your palate in terms of marketing and storytelling and building a brand that most people who sell things on like don't have. Yeah, I think we had a lot of like things that was kind of interesting. I also found out the fascinating thing is that Matt and Kylie always trusted my craziness but in a disciplined way. And so in the early days we would build whatever we wanted to do and then we would want it for a week and then on Sundays Matt would do day to day and if we had kind of dropped in numbers, we would just roll back a whole week.

Right. And so I think we always kind of like intuitive had this fascinating. We don't overthink what we try. We try like many, many, many, many things quite crazy things also but we're super disciplined about killing them very shortly after they don't work.

And I think I've served as well because we don't kind of overthink stuff but we also don't like the things way out if it's not very good. So what's an example of one of the off the wall things you guys tried that actually did work? Well, I think celebrity dogs was kind of like a great thing. What celebrity dogs?

I mean, like for a while these like the famous dogs on Instagram? Yeah, I think in many ways we grew up with it. I'm not sure we kind of like made that environment happen or they kind of were there and we just tapped into it but at one point I think we had 150 dogs on payroll and so like tune in the mail is my heart. So how does this happen?

So you see somebody else posting on their dogs account and you're like this has potential and you. We started to just answer or what happened? Well, this is back in 12, right? So the influencer thing is not really there yet and suddenly we see for example two emails my heart which is this wonderful dog that has like a very crazy face and coordinate the mom of this dog kind of like posting and she has this kind of very sweet story and she's a wonderful person and so we just reach out and say hey can we do something together and suddenly we start to roll up a lot of these different dogs and I think we started to get a lot of followers I think we have about 11 million on the brand page and so we start to promote all these dogs and in return they were promoting us and so it became like this very nice symbiotic kind of relationship between us and celebrity dogs.

That's amazing. Were you guys able to sort of track like now that you look back and I'm sure that's the at that era it was like probably the golden era of low cost, high return, how much of sales do you think came from something like that? I don't know because a lot of these things I think in the early days was tough to kind of like shoot people directly right but we've always been pretty disciplined by having a cat that we stick to so I would imagine it was like within those I don't know what it was back then like 20 bucks 30 bucks or whatever it was that we would offer these celebrity dogs if they convert into a cell. Back then you could be a little bit more like hey we only pay for subscribers I think these days like you have to pay for a lot of pay to play.

So I think we've always done a lot of that we've done books we've done 10,000 people, Coachella for dogs events we've done. When was that? This is like something called Fox Fest we still do some of them not as big as we found out that was a little bit too many dogs in one place but we have comedy nights we have movie nights we write all these different kinds of like if you search for dog mom rap we have hundreds of millions of users from each and seeing their love songs to dogs and so we always been kind of like pretty out there and kind of what we tried to do. Yeah that's good I like that.

What other companies or brands do you think do a good job of this? When you were talking I had one that came to mind so if you can't think of one I'll share it with you but is there anybody that you look at and you say man they're doing a really good job with this sort of creative marketing really sort of like understanding the customer and delivering them happiness in all these different ways. When that comes to mind which is kind of odd is that in New York City there is a home storage kind of thing and they have these hilarious kind of like you know we're into space kind of like funny kind of statements everywhere and often they change them up so they're kind topical. Yeah and you said something actually at the beginning you said you guys have both come from a venture back startup and this is sort of like a refresher right you were like I'm going to work on a product I love for a customer I love and let's not raise a lot of money let's just kind of bootstrap this thing.

What was that thing you did before is that actually where you made your first million like I think a lot of our listeners really like to know when somebody started this one what was their circumstances were they you know doing okay financially we did they have a job what was your tracker before this. I started in London I was part of the founding team was something called Juiced which was an online video kind of portal like Hulu before Hulu and we raised a lot of money because my co-founder that started it had done Skype and so it was I think it was $50 million seat round kind of thing and Sequoia and Index and everybody else was involved and I think in many ways we hired in 200 people in nine months I understood you know like how that type of game was being played and Matt had been more successful than I and in startup world he was part of meetup and was a co-founder of that and then I went out to join a small team in Brooklyn afterwards called Hot Potato and then end up sent to Facebook and Matt ended up joining I think a few other startups and so we've just been like in the venture kind of like run startup world for a while and I think we were like a little bit of like hey wouldn't it be nice if you could just build a business that was making a moment of spending and so it was a little bit of like a whole school process. Yeah the classics. Maybe we should try to make somebody.

Were you after those first two were you in a spot where you could just work on whatever you want for as long as you wanted or was like singles and you were searching for a home run what was your mindset and where was your life at that time. I think I've always been pretty frugal so I've probably been never like had the million and so it was always really about having enough run rate that I didn't have to do stuff I didn't want to do so when I learned my come as my wife to kind of move to New York it was like well that's what I think it was a hundred thousand dollars into kind of from our savings and we were like okay if you spend this then this game over like we're back and so luckily we made some money kind of like along the way it wasn't kind of like I've always had a good job at interview and so I wouldn't say that I was kind of like struggling I was kind of like probably wasn't rich but I wasn't poor either. Yeah that's helpful and it sounds like you had a mindset of you wanted to own sort of your time to work on what projects you found interesting and that's kind of what I'm reading from. Yeah and I was doing consulting at the same time right and so in the early days of pre-high you know we were really helping big businesses figure out how you could start new businesses and so that kind of created some cash flow and really gave me kind of like the time to not have to rush.

Right and so what was the last job you had that you hated for fifteen? You weren't the first or anything? Yeah I was a dishwasher and I was an usher in a movie theater and before that I was thinking I was like a livery guy for flowers but I don't know why I always like love those things like you like to make a dishwasher I've washed dishes and I hated it. You know what like it was in a restaurant and everybody was really nice and because it was such a hard work and maybe it was because of the demo I just felt it was like I think it was like I don't know eight bucks an hour seven bucks an hour which was like you know twenty years ago like and it's seen amount of money for like a fifteen year old and so I just remember like getting that cash it was just like an unwell it's unbuffled amount of money right now like then having to go back and wash yourself down and kind of dishwasher soap because you had so much of the grease on you like what's not this down.

But I don't know like I've always enjoyed being in an environment where there's other people and you had a little bit of a mission and so I always enjoyed working. I don't think of anything like that. I've definitely kind of like been introduced to projects or companies where they're like hey you know you should do this and I'm like I'm not sure that would be good for me but I've always loved my work. One thing I liked about was doing a little bit of research on you last night when I was a young man and you were going to chat and I said what do I find most interesting about this guy.

I liked that you took sort of a systems approach to things so tell me how did you find your way. You didn't sort of just allow Cupid to shoot his arrow you were intentional about it. Tell me why you were intentional and what you actually did. I think people will find this interesting.

So I had been single for a few years and kind of felt that experience to be both kind of like intriguing because obviously it's a seductive lifestyle to run around and meet a lot of interesting people but I kind of wanted to settle down and so I got a little bit kind of a little bit about it so I started to study all the books I could find about relationships therapy and longevity and relationships and I tried to understand what is actually the background kind of for all these dating algorithm at that time. I've been married to my wife for 10 years so back then it was like really E-Harmony that was out there and was publishing some of their data. And so I basically created these 30-40 properties that would increase the chance of whoever I met if she had those kind of properties that would be a good chance it would stay around for a long time. So what's an example?

Well there's one of the two ways of thinking about it. At least thing I'm no expert that's just like my best concern for me. I think you find somebody who's very similar so very similar upbringing very like similar culture stuff like that. Oh you find somebody who's very compatible so I don't know my bricks I think that's been debunked by now but like somebody who kind of like compliments you up.

And for whatever reason I thought that it's similarity thing was kind of like that is statistically etch and so I know it's not for that. The problem obviously with features of a person is that it's difficult to map out rapport or just chemistry. And so the thesis I had was that if you had somebody with a centipity would be a good proxy for that. So if you like somebody they probably hang around people that you also like.

Now the problem is that I think most people if they're single they kind of like mind so to speak kind of their peer group and so you need to go like one step out. Right. You need to go to your friends friends not just your friends. Exactly right.

So I mapped out who had met who had these properties that I really really liked. What were the three properties that you really cared about for example. That one was the H range. That you need that to be that.

Another one was kind of like for me it was like where they kind of like cultural background and because the statistical kind of element of that. You looked at your friends who matched that. Yeah. And you said okay these are my friends that share something attributes.

And then basically look like either will they be able to invite me to a dinner with some of their peer group or do they have siblings that would allow me to do that. And so the second dinner was I used to go out with this guy. I was on my street and he's an awesome dude unfortunately completely unbrothers store. He unfortunately died in a traffic accident.

None of that's incredible guy. And I thought well he has a kid sister and has all the properties. And so I basically said hey I'm in town next week. I'm going to bring some of my single friends and then maybe bring some of my single girlfriends.

And I met my wife. You were hosting these mixers or dinners or something like that. You would say hey I'm hosting a dinner for single- Very uncomfortable. It makes me feel like a very kind of like.

I think it's great. I think it's awesome. What would you feel like I'm for what do you think? I don't know.

It sounds so non romantic. But in many ways I do think that it's such an important thing in your life. I hope that I will be with my wife forever. And so there's very few things that you can do that as permanent as finding a partner.

And so it's a big decision. And I think in many ways if you're a product developer and you're trying to get new customers and you go on a random site that's nothing to do with it, you're just less likely to be successful. And so I think this idea that you can just walk out on the street and walk out to a random bar and put yourself in a position to be lucky is a little bit naive. And so for me it's a little bit like I enjoy thinking about systems or frameworks for how I do stuff.

And I did feel that this was a good way for me to put myself in a position where I could meet somebody. And ironically I think that she, my wife met a, it's not somebody I think I would normally walk up to in a bar. She doesn't look like what I normally would go for. And she definitely thought she would think I was way too annoying to me when I met her in a bar.

And I was meeting her and then we met. And I knew pretty quickly like I think within three months I decided to propose. I didn't have systems so I waited for a year. We've been happy now.

We have a little boy now. I like the things I like about this is that it's such an important and big part of your life. You can leave it completely up to chance or you can have some intent. Some people's intent looks like I'm going to download this dating app.

I'm going to go to events. I'm going to go to a speed dating app, whatever it is. So people have different ways that they sort of try to help engineer a little bit of serendipity. And I like that what you didn't do was say cool here's the formula and if somebody satisfies this checklist great, let's do it.

You engineered serendipity. You did some work but then you let real life take over and fake take over in a way where you said I don't know who I'll connect with but I'm just going to put myself in positions where maybe I can increase the odds of getting lucky. Totally right. And I think this idea of being purposeful is important.

I now like with most elements of my life sit down and try to think about how can I become better of doing that thing. Being it from health, being family, relationships, what have you. And so I think a lot of us kind of like we go a bit headless into the world and then we go like oh why doesn't this happen to me? Oh why does this always happen to me?

You're kind of like you're standing inside the road and while it's raining. Like chances are that somebody will splash water on you. So what are your other systems you said health? You said some other frameworks maybe.

You know what recently I talked to a friend of mine Dan Shipper and he wrote a framework that I use and I didn't really think that again I thought people would be completely crazy for using this framework but he wrote a lot of people seem to like it so I'll share it. So I have this thing I call the A plus one framework and the A plus one framework is really about the core elements that I'd like to kind of like be quote unquote successful in. And so the boxes are what I call transact which is really how do I make sure that I make sure that I make enough money to find in my life. It's a invest.

How do I make something that have compounding interest over time. It's assist. How can I be helpful to call this for people. I like more on the business side.

Then it's learn which is about how do you become better at understanding what you do as an output and then become more efficient at making that output and it's health. How do you make sure the software and the hardware works right. You know how do you make your mental and your physical health up. And then it's family.

How do I maintain to be a good dad and a good husband. It's a relationship. How do I get to allocate time with people that I like to hang with either because they're smiling at me and I learn from them or they're fine or whatever and then it's ego or self-kinkness. So how to make them.

Now the most important box that's eight boxes. The most important box for me is the ninth which is really spending time thinking about this. I have a grid or something you have a way that you lay this out. I have a grid.

I'm sure people Google can find it. So I put this out and then every week I spend an hour or so actually I do more often. I use this as a way to not be worried that I'm missing something and then a little bit like a growth hacker. I look at these different elements and I think about what experiment can I do next week that could increase the chances of having a positive outcome.

So let me take a moment to everyone. Let's take my kids for example. I have a five year old who I'm obsessed with. I know that in weekends we would play in this playroom and I get a little bit more and so I take my phone and you would call me on it and it kills me.

You're spending time but it's like how many times can I build these same blocks? How many times can I read the same book? Next time I said that on purpose we'll also play. I should try to figure out what experiments can I run that basically has a better output of that interaction model.

And so something as simple as oh you know when I was about five I thought to play ping pong. So I bought a ping pong table right though like a little thing that you put on top of your dining table. And so next weekend I didn't get someplace I put in my little air table with my experiments. And then I went down to try that and he left it and so now we had a thing that we could do that wasn't the bad thing that we used.

You're not checking your phone now. Exactly right. So you know if it's every Friday day night or if it's you know making sure that if you don't like to do exercise in the morning you try to figure out you can do dance lessons. So really brainstorm different types of experiments that you can apply to all those different boxes.

And I think you know for me at least that's made me much more purposeful and much more kind of like stuff away. Like how do I try to kind of like become better of the things I like to do? Yeah. Can I tell you my system?

Yeah. I don't think I've ever told anyone this. So this is good. But I'm similar to you and then I'm weird and want to get better.

Like the phrase I really like is that life is not about what you get. So it's not about the accolades, it's not about the stuff you accumulate. So life is not about what you get. It's about who you become.

And so then I believe that's my truth. So I asked myself well who do I want to become? What is the next version of me? What does your two point look like?

And then how do I work towards that? And so I wrote out for this year. I wrote out four boxes. I don't have eight because I don't think I could juggle that many things.

But even four I thought was too much. And so the four categories that I had was like fitness or health because after my last startup I got so fat I basically put on like I don't know 30, 40 pounds in three, four years of like just doing this company and I was like shit. When I looked at the mirror I was like who's this guy? I don't like this guy.

The second one was building my money machine. So how do I make it so that cool we sold our company. I got this cash inflow. How do I set this up so my money will go work for more money?

And I start to automate that. So I hadn't had enough money in the bank to care about that. But now I could literally live off the interest if I set this up properly. So let me set it up properly.

The third one was learn. So how do I learn as much as I can this year? And the fourth was be a great dad. So I just had a daughter like six weeks ago and I knew that was coming.

So I was like okay how do I set myself up to be a great person? Great. Yeah. First one.

And so decided on my four boxes and I was like these are the four things I care about. Okay cool. I need to like score myself. And then also how do I plan to improve all these?

And so I was like well I need to set up some kind of system that does not require willpower or like remembering to go do some work. And so I just set up this thing that would email me every morning. So I wrote down I was like okay for fitness. That's the most important thing I could do.

Eat clean. Great. And then the second part of that is like exercise. Great.

Not rocket science but I just need to do those two things. And so in my email I'll get an email that has four or five questions. It says are you going to eat clean today? I just reply yes or no.

Are you going to work out today? And what time? And I say yeah I'm going to try to go at 1 p.m. And the second one is like what are you going to do for your family today?

Are you going to set yourself up there and I'm like the last one is learning. What's something you're going to do to expose yourself to something new where you might learn? You say you're only a fool but I think you're getting to the end. I have five actually.

You contribute is a new one because I have this friend Ramon who is such a good person. He helps everybody else out. I saw that I was like okay I need to add that. I need to add that to my things that are important to me is to give to others.

And then an even email to me back my answers and it just says how do you do? I just see I stick to my work. Did I actually exercise or did I say I got too busy and skip? And so that's my whole system was just that like just a little email reminder loop in the morning and in the evening and it's been so amazing.

And I just like if you're out there you go set this up. You're a simple. It is really improved the quality of my life. Is Trello all my the system I have is that every time I have any idea in my head it goes into basically a Trello inbox and so I have an app on my phone that has the only purpose of sending it to that thing.

Or I mean if this and that kind of like Alexa or Google home things. Wherever you are you can quickly input. And so and then I have those different categories kind of like out in the board system. A basic triage kind of like at the end of the day all these kind of different things I had in my head and then I just put them in there.

You know I remember the site it's called Superorganizers. That's the one that Denship is doing and he's basically interviewing people like you and me and there seem to be more than like a thing that was the last one that kind of have all these systems for trying to optimize their life. Yes I did read that. That's where I read about you.

Superorganizers. Check it out. It's a good interview with you. The founder of Forceware I think he had a good one too.

Yeah like it's basically what weird systems have you hacked together to try to improve yourself. That's one of the things that at least like I aspire to be kind of pretty good at a lot of things or like average good at a lot of things instead of like they're good at just one right I think for music sets doesn't look like necessarily a million bucks but if that means that I can't hang with my son right or that I can't be a good husband right or. And so in many ways I think a how can I score as high as possible on all these eight boxes. Right.

I don't hear that many people who talk about like being kind of like super average in that way or super average. Right. But in many ways like I would rather do that than work myself to death or. In one of those categories.

Yeah. Yeah. What's the right way to think about that? Some people say work life balance right they want they like to be balanced but balance is very hard to achieve in some ways like you said you want to level all those it sounds like you don't think that there's like a finite amount of time or energy you don't feel like restricted it sounds like you think you can level them all up to the point where you want them to be how do you think about it and if somebody's out there struggling to say oh man it's really hard to balance this and that and this other thing and I'm like I heard this guy's doing eight things.

What's the right way to think about balance? Well then do all eight things at the same time right. So I think obviously first with the disclaimer like you know I have the system it works for me like if that's one thing I learned about entrepreneurship and a general life advice is that just because it works for one person doesn't mean that it has to work for everybody else and so take it as inspiration rather than kind of like a description a few things I think you can take these boxes and you can overlap them and so for me for example like I work with people I really really like Matt and Kyle. So friends or coworkers you get two for one.

You get relationship and you get transact right you know sometimes if you saw a young thing you get transact and invest right because you often make both some salary and you have some stock options and so there's a way I think of kind of like making sure that you take a lot of these elements you know you have a business meeting it's easy to say you know let's just walk around the block and then suddenly specifically in San Francisco like you got your hot rate up because you're working over hill and so I think there is ways of trying to kind of compact these kind of different things and get a little bit more of that and then also it's a little bit about just being realistic with how much to achieve in the different ones you know at a short period of time these things all relative like you all want to be healthy but one of the issues we have is like we don't know what a hundred percent healthy you look like and so I definitely do that I stress all the time like you know what I work out two or three times a week is that enough you get a number you have high cholesterol and you're you know what I mean and like you know I'm going to die tomorrow and so I don't think this is there there's a unique answer but one hack for me is to try to kind of like overlap stuff sometimes the trick is to separate them so for example sometimes I mean people have really good jobs that they like whether they make a decent amount of money and they go like well I should really leave and join us not up to get equity and I was like well maybe you're just going to spend some of the extra cash you made and invest in some things so that you don't kind of like take the risk on the cash situation and so sometimes I think it's also about separating the boxes instead of collapsing them. Right I like that. Alright so we'll finish out with a couple of my favorite questions just to round it out. So if you were 21 years old again today and you couldn't work on the business you're working on now what do you think you'd be interested in doing?

What business? What idea? What space would draw you in if you're 21 years old today? I think that innovation is exponential and so I think a lot of us is kind of like chasing the vision of the products that we've thought about the last 20 years on the internet and so I think some of those areas that I think just kind of like might just completely turn everything upside down is the stuff that I think everybody's always thinking of biome stuff like microbiome thing I'd like to understand better.

It seems that there's a lot of kind of like movement there so I think I would maybe study some biology or you know like when it's in fiscal but I do think there seems to be a new space age coming you know there's talk about Mars and I think in a world where everybody is so depressed there's some nice positivity about like we can conquer new things but it's a very unique American thing like in Europe you like very inspiring yeah because in Europe we go like why would you do that? Here's like yeah that sounds incredible and so you know I definitely went through my 20s and 30s being like super anxious about you know everything and so you know running into a calm app my five year old now he listened to headspace to fall asleep and I think like being able to kind of like become much better of understanding your thoughts like if you could learn that in your 20s and 30s I think I would have superpowers right instead of just kind of like randomly sweating nervous chasing everything. Okay like it and if somebody's listening to this and they're like hey Henry is great love what they're doing at bark love his philosophy love his a plus one framework what's the best way to follow you get more of you whatever you get more your thoughts more your ideas you have your podcast so shout out how people should connect with you and then lastly who should reach out to you who are you looking to get in touch with who do you want to hear more from if you're recruiting for companies or deals you want to do whatever it is. Well obviously for bark we are always looking for good people we have a lot of open roles you go into bark.co for such jobs there's a lot of open roles anybody who would like to build the next Disney for dogs about to hear from Twitter is at wordlin I check that too much and so so if people want to get connected that's probably the best time and obviously I have a podcast called Pre-Hype where I really talk about people who think in systems and so people intrigued of that world that you check that out.

Great awesome thank you for doing that this is good. Of course thank you. I need the color color color. Let's go down.

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