My First Million: #23 - Disney for Dogs

All right.

Quick break to tell you about another podcast that we're interested in right now, HubSpot

just launched a Shark Tank rewatch podcast called Another Bite.

Every week, the hosts relive the latest and greatest pitches from Shark Tank, from Squatty

Potty to the Mench on a Bench to Ring Doorbell, and they break down why these pitches were

winners or losers.

And each company's go-to-market strategy, branding, pricing, valuation, everything.

Basically all the things you want to know about how to survive the tank and scale your

company on your own.

If you want to give it a listen, you can find another bite on whatever podcast app you listen

to, like Apple or Spotify or whatever you're using right now.

All right.

Back to the show.

Who's that good-looking boy?

Today, we are going to be opening our first box for my dog, Rustin.

I believe the box was $22 for a month 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 want to 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 least shitty idea of the day.

We definitely didn't think it would be a big business.

I think what we saw pretty quickly was that it was working.

You guys are doing somewhere on the order of $250 million in revenue annually.

$5 million is not enough.

$10 million.

$10 million.

$20 million.

$100 million.

$150 million.

$150 million.

One or two people in a bedroom actually put threats to these like 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 zeroes.

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 with all the details like, how did you get your first

hundred customers?

What did it feel like when shit hit the fan?

I asked them, how did you spend your money now that you're rich?

And what would you do if you were starting over from scratch again today?

If you're like me and you want to own your own business instead of living a 9 to 5 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.

And why Disney?

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 peck what they are.

You know, they make toys, they make theme parks, 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 is 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.

You know, I see people in the dog park who are like, they own four dogs.

They, you know, eat off the same plate type of thing.

Give me a sense of the spectrum.

Where are you at just before you started 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.

Like, I love my dog.

Like, my dog is my little child and I would do anything for her.

I'm not necessarily somebody who would like have a hundred dogs at home.

And so I think in many ways, it's the same way that I have with my kid, right?

I love my son, but like, it's not that I'm going like, ooh, there's like 20 babies on

the plane.

So I think for me, we obviously in the company have like a lot of different kind of permutations

of crazy dog people.

I think the craziness for me is in the kind of togetherness between me and my dog.

And 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 a forever home.

So I guess in that way, I'd probably skew more into somebody who loves dogs than like

the average person.

But I, you know, like I'm not the one who kind of have like pictures of dogs everywhere

and a bone in my key chain.

And so given that, where did the initial idea come from?

Where were you?

Where were you?

What were you doing before this?

I wish you didn't know where I was because that's actually a somewhat kind of 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 shape bed on a cruise ship in my boxers.

And that sounds not as appropriate.

It's a little bit less on appropriate story as it might sound.

So first we're three co-founders, Matt, Kali and I.

And Matt and I were both kind of working in kind of like in between type of roles.

We'd both built startups before and had exited them or kind of like doing our next thing.

So Matt was at kind of like an incubator type place called Dogpatch Labs.

So he was running that New York and I had started a kind of halfway home for entrepreneurs

called PreHype.

And we were on a Summit Sierra conference and so many years ago they had one on a big cruise

ship.

Yeah, I remember that.

Summit at sea, right?

Summit at sea.

And so if you were a little bit of a cheapskate, you would pick the cheap ticket, which were

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've taken this hot shape bed and they pushed it apart, right?

Because it's two random people.

I thought we had hilarious to put them back together.

So I put them back together and kind of redid 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, we were like in this kind

of awkward under one duvet kind of like, hello, my name is Henry.

In many ways, like I think it's formed the DNA of the company in the sense of 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 in East 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 spitballing.

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, like 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 brainstorms, anything on the second

Friday or just a little bit, well, I love my dog.

By that time I was fostering and Matt has a dog called Hugo that he is obsessed with

and like real obsessed as an insane, crazy dog parent obsessed.

It's a big, great day and it was tough to find good stuff for his dog in New York City.

So we're like, hey, 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, 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 is trying to make dogs happy, dogs and their people.

We have a number of different products and services.

The ones that...

I like that you said dogs and their people instead of people and their dogs.

That's good.

Well, they come first in our world, right?

So the product that we're best known for is either BarkBox or SuperTruer.

Those are two boxes, one of these subscription boxes with treats and toys and chews that

gets sent.

They're themed.

So there's something funny for both the dog and their parents.

But we also now do dental products.

We have membership subscription parks and all these other things.

And so we've kind of like branched out from being kind of like a one product company.

So the core thing that kind of helped you guys break through was the 20-ish bucks a

month, BarkBox.

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 about the company.

I want to go right back to where we were.

Okay.

So were you looking at at the time that you were like, hey, could we do this for our dogs?

So the only box that really wasn't around at that time was BirchBox.

And so it was out in New York and I knew off Katya and Haley, who 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 we're, instead of getting, you know, where we might kind of like do more thematic and

stuff like that.

And so practically, I wanted to be respectful of them.

So I cold emailed them and said, hey, I've met them a few times.

It wasn't completely cold.

Right.

Just saying, hey, we're thinking about doing this thing for dogs.

We think it'll be a little thing, but I want to be respectful and come by and tell us what

you do.

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 we were very grateful for all the help that they provided.

Amazing.

Okay.

So decide to start this thing.

Yeah.

So doing this, what was the second best idea that you guys were brains with?

What was the name of your co-founder?

I met Mika and Kali Strife.

So I think it was Matt at the time that you had met in the heart shaped bed.

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 he even called something really stupid, like

ducky baggy or something like that.

So I would send that to Matt and we would both kind of start to go like, we should just

see if people like it.

And so then next week when we met people, they were saying, well, what do you think,

you know, as entrepreneurs do, like, what do you think and what do you work on?

Yeah.

It was like, oh, we're working on this thing.

And Matt started it by somebody was saying, hey, you should sign me up when you're ready.

And he was like, well, I've square on my phone, I can just take your credit card right

now.

Yeah.

It's a life.

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, had started Uber in New York.

And so she was, I can't remember the 11th high or something like that in all of Uber.

So she was like running around, kind of like signing up limousine drivers.

And she was hanging a lot in dark patch labs.

And so we were like, hey, maybe we should get somebody to help us.

Like actually, we have to make some boxes.

Deliver on this.

So we learned her into kind of like a little three people founder team.

And then she really just ran with it.

And so, you know, kind of is this amazing person who are just very efficient of getting

everything done.

And so I kind of blinked twice.

And then suddenly there was like boxes appearing in front of us.

And so this just that way, we were just packing the boxes ourselves, right?

You know, Carly would run down and get some product and, you know, we got the brown boxes

you can buy in the post office.

And then we start packing.

I'm a dyslexic Dane Sauver at Happy Holidays with two L's and my 70 boxes and they were

shouting at me.

And then we were kind of off, right?

You know, it never really was like, let's start a company.

It was more like, hey, 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 Hollison.

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 the 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, you know, these decisions were important and all the stuff.

And so.

The only thing I would say to that is that I think we definitely didn't think it would

be a big business, right?

You know, we are like, we should never raise a venture.

We should do it ourselves.

It'll be a side-to-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.

This 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 epic.

So we put this product online and like it wasn't like, obviously like we skyrocket the

next day, but like there was real traction, like you could feel that people were into it.

And so what happened to those first 70 customers?

Those are friends and friends of friends, basically.

Is that right?

Yeah.

Like people we randomly meet.

Yeah.

And so what were the next 700 people?

Where did they come from?

Advertising, 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 we're talking to customers, if you can kind of like 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 it and 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 you

boyfriend?

Then it was about like five ways to clean the paw of your dog.

And I think everything, things tend to be pretty utilitarian because most product owners

or 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

this theme.

And again, like we didn't think it would be that big.

So in the early days, we were just posting stuff that we thought was funny and we thought,

you know, it'd be funny to pretend that we were a dog and trolling people on Facebook,

right?

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 you said you were at MTV before.

What were you doing at MTV?

Yeah, my background is kind of messy.

I thought I wanted to be a radio journalist and so I started up at BBC doing radio journalism

and then God offered to did a radio documentary about MTV and then got to hang there.

And then it was kind of funny story was I was then sitting writing my final thesis and

everybody at work thought I was working really hard because I didn't have a computer home

so I'd 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 late 90s.

And so they figured that out and so they were asking, can you help us build a product

or TV show about like this internet?

This is before we had a website in MTV.

And I was like, so I came up with this idea, which now sounds pretty stupid, but an obvious

but it was kind of UGC.

But if to show that on air, it's 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 percenter look like she was a flash animation and then show her in the same environment

as the other thing.

Anyway, so I came up with this idea, pitched my boss, he was like, oh, interesting, but

and then pitch a little bit around everybody thought it was idiotic cut it because it ran

through a Windows like 95 computer.

And the engineers were like, there will never be a 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 is amazing.

We're going to see it.

And everybody in turn was like, why haven't we heard about it?

So you just hijacked MTV into the 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, Henrik question mark and I replied back, I don't know

anything about it.

And he goes like, dude, don't ever do that again, but I want the show on air.

And so I went from being a producer to basically run product development for all channels outside

the US.

And I did that for eight years or so and then MTV games and a lot of like, you know, SMS

to 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 yeah, I can imagine how that would help, you know, refine your palette in terms

of marketing and storytelling and building a brand that most people who sell things online

don't have.

Yeah.

And 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 have 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.

And so I think we've always kind of like intuitively 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 if they don't work.

And so that kind of like bipolar kind of like attitude, I think have served us well because

we don't kind of overthink stuff, but we also don't like let things play 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?

I think celebrity dogs was kind of like a crazy thing.

Like we were.

What celebrity dogs?

I mean, like for a while, at least like the famous dogs on Instagram.

Yeah.

I think in many ways we grew up with an nursery.

We kind of like made that environment happen or they kind of were they and we just tapped

into it.

But at one point, I think we had 150 dogs on payroll.

And so like, you know, tuna mills my hot and so how does this happen?

So there's, you see somebody else posting on their dogs account and you're like, this

has potential and you as an influencer 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, tuna mills my hot, which is this wonderful dog that has

like a very crazy face and Courtney, the mom of this dog, kind of like is posting and

she has this kind of very sweet store and she's a wonderful person.

And so we just reach out and saying, 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, you know, a lot of followers.

I think we have about 11 million on the brand's page, 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, and

celebrity dogs.

And that's amazing.

And were you guys able to sort of track like now that you look back and I'm sure that at

that era, it was like probably the golden era of like low cost, high return.

How much in sales do you think came from something like that?

I don't know.

Cause a lot of these things I think in the early days was tough to kind of like attribute

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, back then like 20 bucks or 30

bucks or whatever it was that we would offer these celebrity dogs if they converted into

a sale.

Back then you could be a little bit more like, Hey, we will 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?

It was like something called box fest.

We still do some of them, not as big cause we found out that was a little bit too many

dogs in one place, but we have standup 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 views of comedians singing their love songs to dogs.

And so we've 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 that 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.

The one that comes to mind, which is kind of odd is that in New York City, there is

a home storage kind of thing or like, 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 of topical.

Yeah.

And you said something actually at the beginning, you said, you guys had both come from a venture

back startup, and this was 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?

Did they have a job?

What was your track record before this?

I think I started, in London, I was part of the founding team of something called Juice

Juice, which was an online video, a kind of portal, like Hulu before Hulu.

And we raised a lot of money because my co-founder, guys who started it, had done Skype.

And so it was, I think it was $50 million seat round kind of thing, right?

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 am in startup world.

He was part of Meetup, and was the co-founder of that.

And I went out to join a small team in Brooklyn afterwards, I call hot potato, and then ended

up selling 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 more money than it was spending.

And so it was, you know, it's just a little bit of like an old school approach.

Yeah, the classics.

Maybe we should try to make some money.

And 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 were those 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.

And so, you know, when I learned my, convinced my wife to kind of move to New York, it was

like, well, let's put like, I think it was $100,000 into kind of like taking from our

savings.

And we were like, okay, if we spend this, then it's game over, like we're back in Europe.

And so, loggily, we made some money kind of like along the way.

It wasn't kind of like, I've always been lucky I had a good job at MTV.

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

whatever projects you found interesting.

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-hype, 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.

And so what was the last job you had that you hated?

For 15?

You know what?

You know what?

Yeah, I was a dishwasher and I was an usher in a movie theater.

And before that, I was think I was like a livery guy for flowers, but I don't know why.

I always like loved those things like that.

You liked being a dishwasher.

You know what?

I've washed dishes and I hated it.

You know what?

Like I, it was in a restaurant and everybody was really nice.

And because it was such a hard work and maybe it was because it was in Denmark, I just felt

it was like, I think it was, I got like, I don't know, eight bucks an hour, seven bucks

an hour, which was like, you know, 20 years ago, like, and it's seen amount of money for

like a 15 year old.

And so I just remember like, like getting that cash, it was just like an un-thrull.

It's un-thrull the 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 necessarily, but I don't know.

Like I've always enjoyed being in an environment where there was other people and you had a

little bit of a mission.

And so now I always enjoyed working.

I don't, I can't think of anything where like, oh, that's, I've definitely kind of like

been introduced to projects or, 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.

And one thing I liked about, cause I was doing a little bit of research on you last night

when I was, when I knew we 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 wife?

Um, you did do your research.

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 cause obviously it's a seductive lifestyle to, to run around and meet a lot

of interesting people, but kind of wanted to settle down.

And so I got a little bit kind of analytic about it.

So I started to study all the books I could find about relationship therapy and longevity

in relationships and started to try to understand, well, 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 like back then it was like really e-homony that was out then 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, if she had those kind of properties, they'll be a good chance that we'll stay around

for a long time.

So what, what's an example?

Well, there's fundamental two ways of thinking about it.

This thing, I'm no expert.

This is just like my desk disorder for me, either you find somebody who's very similar.

So very similar upbringing, very like similar culture and stuff like that.

All you find somebody is very compatible.

So I don't know if my bricks, I think that's been debunked by now, but like kind of like

somebody who kind of like compliment you well.

And for whatever reason, I thought the very similarity thing was kind of like, had a statistically

edge.

And so I kind of was going for that problem obviously with kind of like features of a

person is that it's difficult to map out rapport or like just chemistry chemistry.

And so the thesis I had was that if you had somebody with serendipity would be a good

proxy for that.

So if you like somebody, they'd 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 mine,

so to speak, kind of their, 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 I'd met, who had these properties that I really, really liked.

What were the three properties that you really cared about, for example?

The one was the H range.

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.

So you looked at first your friends who matched that.

Yeah.

And you said, okay, these are my friends that share some of these 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 grow up with this guy, Rasmus, on my street.

And he's an awesome dude.

Unfortunately, he's completely on, on Relative Store.

He unfortunately died in a traffic accident, none of that's incredible guy.

And I thought, well, he has a kid's sister and has all the properties.

And so I basically said, Hey, you know, I'm in town next week, you know, I'd love to bring

some of my single friends and then maybe you can bring some of your single girlfriends

and, and I met my wife and we've been you were, you were hosting like these mixers or

dinners or something like that.

You would say, Hey, I'm hosting a dinner for single people.

Very uncomfortable as it makes me just feel like a very kind of, I think it's great.

I think it's awesome.

Well, will you feel uncomfortable?

Why do you feel uncomfortable?

I don't know.

Like it's just, it sounds so non romantic, but in many ways I do think that it's such

an important thing in your life, right?

You know, I hope that I will be with my wife forever, right?

And so there's very few things that you can do that as permanent as, as finding a partner.

And so it's a big decision.

And, and I think in many ways, if, you know, 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.

Like you're just less likely to be successful.

And so I think this idea that you can just walk out on the street or walk out to a random

bar and then kind of put yourself in a position to be lucky is a little bit naive.

And so for me, it was a little bit, as you say, like I enjoy thinking about systems or

frameworks for how I do stuff.

And I did feel that this was like a good way for me to put myself in a position where I

could meet somebody.

And ironically, I think that she, my wife, uh, Metta is not somebody I think I would

normally walk up to in a bar.

Like she doesn't look like what I normally would kind of like go for and, and, and she

definitely thought I, she would think that was way too annoying or I met her in a bar.

So I was grateful for kind of like meeting him there.

And yeah, then we met and I think, you know, I knew pretty quickly, like I think within

three months I decided to propose.

I didn't have a system.

So I waited for a year.

But yeah, we've been happy now.

We have a, we have a little boy now and that's amazing.

I like that, you know, the things I like about this is that you're right, 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, you know, go to a speed dating thing, whatever it is.

So people have different ways that they sort of try to help engineer a little bit of serendipity.

And I think 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, right?

You did some work, but then you let real life take over and fate take over in a way where

you said, you know, I don't know who I'll meet, 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 sort of odds

of getting lucky.

Totally right.

And I think this idea of being purposeful is important.

Like, you know, I now, like with most elements of my life, sit down and try to think about

how can I become better of doing, you know, that thing, you know, being it from health

or being family, relationships, what have you.

And so I think a lot of us kind of like we are, we go a little bit headless into the

world and then we, you know, go like, oh, why doesn't this happen to me or why does this

always happen to me?

And you're kind of, well, you know, kind of, you know, like you're standing on the side

of a road and while it's raining, like chances are that somebody will splash some water on

you.

Right.

What are your other systems?

You said health.

You said you have some other frameworks, maybe.

You know, recently I talked to a friend of mine, Dan Shipper, and he wrote a framework

up that I use and I didn't really think that, again, I thought people would thought I would

be completely crazy for using this framework, but he wrote it up and 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 enough money to finance my life?

It's invest.

It's how do I make something that have compounding interest over time?

It's assist.

How can it be helpful to causes for people?

So that's kind of like more on the business side.

Right.

How do you learn, which is about how do you become better of understanding what you do

as an output and then become more efficient of making that output?

And it's health.

How do you make sure the software and the hardware works right?

You know, how you keep 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

smarter than me and I learned from them or they're fine or whatever.

And then it's ego or self-kindness.

So how to make sure.

Now, the most important box, that's the old eight boxes.

The most important box for me is the ninth, which is really spending time thinking about

this.

Right.

And do you actually have like a grid or something?

You have a way that you lay this out, these eight boxes?

Yeah, I have a grid, but I'm sure people Google that can find it.

Yeah.

So I put this out and then every week I spend, you know, an hour or so, actually I do it

more often.

I use this as a way to kind of like not being worried that I'm missing something.

And then a little bit like a kind of like a growth hacker, I look at these different

elements and I think about it.

What experiment can I do next week that could increase the chances of having a positive outcome?

So let me take a non-intuitive one.

Let's take my kids, for example, like, so I have a five-year-old who I am obsessed with,

right?

You know, my little boy Anton.

One, at times I notice in weekends, we would play in his playroom and I get a little bit

kind of bored.

And so I take out my phone and he would call me on it and it kills me.

Right.

You're spending time, but it's like, how many times can I build these same boxes?

Same blocks.

Exactly.

How many times can I read the same book?

Next time we'll set them.

It'll be purposeful.

I should try to figure out what experiments can everyone 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 started to play ping

pong.

So I bought a ping pong table.

Right?

That was like a little thing that you put on top of your dining table.

And so next weekend, I didn't, again, because I'm slightly crazy, I put in my little air

table of my experiments and then I went down to try that and he loved it.

And so now we had a thing that we could do that wasn't the bad thing that we used to

do.

You're not checking your phone now.

Exactly right.

And so I think, you know, if it's every Friday date 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, like, you know, 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, like that's made me much more purposeful and much

more kind of like self aware of like, how do I try to kind of like become better of the

things I'd 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 that I'm weird and want to get better.

Like I, the phrase I really like is that life is not about what you get.

So it's not about the accolades, 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 to be true.

So I asked myself, well, who do I want to become?

What is the, you know, the next version of me?

What does Sean two point and look like, and then how do I work towards that?

And so I wrote out for this year, I wrote out my four boxes.

So I don't have eight, cause 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 a shit.

When I looked in 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, you know, inflow.

How do I set this up?

So my money will go work for more money.

And I, and I start to automate that cause I hadn't really, 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 first one?

Great family man.

Yeah.

Oh, 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, you know, sort of score myself.

How am I doing in each right now?

Let's be honest.

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

to 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 and it has, you know, four or five questions that

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 one PM today.

Then the second one is like, what are you going to do for your family today?

How are you going to invest in your family today?

Another one is how are you going to invest in others today to contribute?

And the last one is like, what are you going to do for your money machine today?

How are you going to set yourself up to earn more money?

And the last one is around learning, you know, what's, what's something you're going to

do to expose yourself to something new where you might learn.

You say you only have four, but I think you're getting to the eight that I'm also doing.

I have five actually.

Contribute is a new one because I have this friend Ramon who is such a good person.

He helps everybody else out.

And I, when 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 in the evening, it emails me and just said, it emails, it emails me back my answers.

And it just says, how'd you do?

And it says, did I stick to my word?

Did I actually exercise?

Or did I say I got too busy and skipped it?

And so that's my whole system was just that, like just a little email reminder loop and

the morning and in the evening.

And it's been so amazing.

And I just like, if you're out there, go set this up, use Zapier.

It's so simple.

It has really improved the quality of my life is Trello.

So all my, the system that 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 made an, 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 guess you put them in there.

Yeah.

And so, you know, I remember the site, it's called Super Organizers.

That's the one that Den Shipper is doing.

And he's basically interviewing people like you and me.

And there seemed to be more than like I think Naveen was the last one that kind of have

all these systems for trying to optimize their life.

Yeah.

Super.

I did read that.

That's where that's the thing I read about you, Super Organizers.

Yeah.

Check it out.

It's a good interview with you.

Naveen, who's the founder of Foursquare, I think he had a good one too.

Yeah.

Like it's basically what weird systems have you hacked together to try to like improve

yourself?

Cause I think 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 very good at

just one, right?

I think for me, success doesn't look like necessarily a million bucks, but if that means

that I can't hang with my son or that I can't be a good husband, right?

And so in many ways, I think a how can I score as high as possible on all these eight boxes?

I don't hear that many people who talk about like being kind of like super average in that

way or super above average.

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 their life to be balanced, but balance is very hard to achieve and in some ways,

like you said, you want to level all those up.

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 oh my God, I heard this guy's doing eight things.

What's the right way to think about balance?

Well, I don't do all eight things at the same time, right?

So I think obviously first with the disclaimer, like, you know, I have this system, it works

for me.

Like if there'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 prescription.

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 Cali.

So friends or coworkers, you get two for one.

You get relationship and you get transact, right?

You know, sometimes if you start your own 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, right?

Then suddenly specific in San Francisco, like you get your heart rate up because you're

walking 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 out of that.

And then the thing 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 are all relative, like we all want to be healthier, but one of the issues

we have is like, we don't know what a hundred percent's healthier look like.

And so I definitely do that.

I stress all the time, like, you know, I work out two or three times a week, is that

enough?

You get a number and you have high cholesterol and you're just like, oh, you know, what does

that mean?

And like, you know, I'm going to die tomorrow.

And so I don't think necessarily 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 meet people who have really good jobs that they like where

they make a decent amount of money and they go like, well, I should really leave and join

a startup to get equity.

And I was like, well, maybe you should just kind of spend some of the extra cash you made

and invest in 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 like collapsing them.

Right.

I like that.

All right.

So we'll finish out with a couple of my favorite questions 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 were 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 obviously thinking

of biome stuff, like microbiome thing, I would 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 San Francisco, but

I do think there seemed to be a new space age coming.

You know, there's talk about Mars and I think, you know, in a world where everybody is so

depressed, there's some nice positivity about like, we can conquer new things.

Right.

It's a very unique American thing.

Like in Europe, people go like...

Very inspiring.

Yeah.

Like, why would you do that?

Here's like, yeah, that sounds incredible.

And so, you know, I definitely went through my twenties and thirties 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 twenties and thirties, I think I would have super

proud of us, right, instead of just kind of like randomly sweating, nervous, chasing everything.

Okay.

I like it.

And if somebody's listening to this and they're like, hey, Henry, he's 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?

Where can they get more of your thoughts, more of 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 or whatever it is?

Well, obviously for Bark, we are always looking for good people.

We have a lot of open roles.

If you go into bark.co, forward slash jobs, there is a lot of open roles.

So anybody who would like to build the next Disney for dogs would love to hear from.

Twitter is at wordlin.

I check that too much.

And so people want to get connected.

That's probably the best time.

And obviously I have a podcast called Prehype where I really talk about people who think

in systems and so people intrigued of that world.

They should check that out.

Great.

Thank you for doing this, man.

This is good.

Of course.

Thank you.

I need a dollar, dollar, dollar.

That's what I need.

Well, I need a dollar, dollar, dollar.

That's what I need.

Said I need a dollar, dollar, dollar.

That's what I need.

And if I share with you my story, would you share your dollar with me?

Machine-generated transcript that may contain inaccuracies.