I Taught Myself To Code in a Dunkin’ Donuts | Ishmael Samuel

I was born in a country called Sudan. It's just like a very war-torn country. My family and I moved in as refugees when I was pretty young. We came to the United States. Literally the first day that we moved in, the house got shot up, and that was like the welcoming. Oftentimes, like, you don't know what the thing that you need is, but you know what you shouldn't be doing. I just couldn't see myself sitting in a classroom for any longer. Started teaching myself HTML, CSS, JavaScript, and I was like a 19-year-old with no job, like negative $200 or something, and I was like, I don't know what I'm gonna do. I walked around really scared and confused, and then Something just kind of snaps. The only thing that made sense was being a founder of a software company.

So what is Paragon?

Paragon is an embedded integration platform. I've raised about $22 million in funding.

If people listen to this whole podcast, if they forget everything but they remember one thing, what would you want them to remember?

Welcome to The Maker Podcast. My name is Matt Carley. I'm here with my co-host and co-founder Max Hellerstein. On the show, we basically just interview the top founders under 35 that have raised at least $1 million for their companies or are doing over $1 million a year. And we just try to have really honest conversations, hear where they came from, what they've built, how they've built it, and the highs and lows along the way. And excited for you to hear it. So thanks for tuning in.

Ish, welcome to The Maker Pod.

Are we getting started?

Yeah.

No, no.

Hey guys.

Welcome, man.

Thank you for having me, guys.

Of course. Thanks for doing this.

Yeah, absolutely. I, I just want to say, Ish, I feel like getting to know you the past, what, 6 months? Been like 6 months since February.

I think probably. Yeah, 9-ish.

Wow, dude, it's felt like 10 years, honestly. I feel like you have had such a massive impact on me as a friend, as a founder, hearing your story, just like the way you operate, everything about you is just so interesting and, and equally inspiring that Max and I were both just like so stoked about the idea of having you on.

Such a no-brainer. We were like, oh, we got to have Vish on this.

Oh, thank you guys. I appreciate it. Maker has changed my life. I've said it time and time again, but it's like one of my 3 top decisions of the year joining Maker.

I've met so many amazing people.

Yeah, exactly.

That was literally what I was thinking. I think it goes without saying that you've also just been such an active member of the community and helped so many founders. And so like, I'm just really excited for you to talk a bit about your story that we, we actually, Matt and I, get to know, but now we get to share with like the world, that is just so fascinating. And like, I think just is so clear that your, your story is just not only unconventional, but like really makes, I think, you appreciate where you are today and where the business is today.

Thank you. Thank you. Yeah, I'm excited to share.

Why don't we start with the origin story? Kind of like tell us, set the scene, like where were you born? What was life like early on? Talk about childhood. Like, just give us the, you know, we'll get to all the company stuff, but I'd love to know just like Start us from the very beginning.

Yeah, so I was born in a country called Sudan before, you know, they split. Um, I was born just outside of Khartoum. Um, and Sudan, as many people might know, is just like a very worn, torn country. Um, politics, resources, tribal warfare, um, genocides in Sudan. It's just like a very desolate place. And, um, unfortunately, my family and I, uh, escaped as refugees when I was pretty young. Spent some time in Egypt in a refugee camp for some time, uh, and I spent some time in my youth there. And my mother, she actually escaped, um, first and found a church to sponsor us. Um, the context is that I have 3 big sisters and her and my father were trying to decide who should stay back at the refugee camp. And they had decided it would actually be safer for my fathers to stick around because I had 3 big sisters and we were all under like 10 years old. I was 2 or 3 at the time. And so she traveled like hundreds of miles, found a church to sponsor her. She came to the United States, worked as a nanny, and then through saving some funds and another church in the US sponsoring us, we're able to come across and ask for Deacon.

How much of that do you remember?

I only remember like a few flashes. There's exactly two scenes that I remember before I came to the US. One of them, is a pretty happy scene. I just remember laying in my mother's arms in this house, like on the porch. And, uh, it's like a wooden, wooden house. And, uh, the other is not so pleasant. Uh, yeah, it's actually pretty gruesome.

Oh man.

Yeah.

And so you were at this refugee camp and then you're out, you're 2 years old, you said?

Yeah, 2 years old.

Wow. Got you. And then, and then where does life take you?

Yeah. Um, so. We came to the United States, spent a little bit of time in Minnesota and then moved to Nebraska when I was 3 years old. So we came across in 1996 and I spent pretty much my entire youth from 3 years old until 17 years old in Omaha, Nebraska.

Why Nebraska?

You know, that's a good question. So fun fact, Nebraska has the highest density of Sudanese people in the country. Wow, really? My take on it now as an adult is that it's just when people immigrate, they go to where their people are. Um, and so numerous times, like I remember, you know, when we came in, we stayed with the family. They all moved into, you know, one room. After a while, my parents were able to get jobs. You know, we got a house down the street. Several times growing up, we'd all move into one or two bedrooms. The family would stay with us till they got off their feet. They'd move next door. Then we'd see the same thing several times. Full circle of life. Yeah.

And then so what is early life, childhood in America, going from Sudan to America? What was your, what was life like? How was the integrating into that?

I think it was, it was difficult, particularly where I grew up. Um, I grew up in a really, really terrible neighborhood and I, you know, shared this story a few days ago at the Maker Retreat, but, um, the house that I grew up in was like deep in gangland and literally the first day that we moved in, you know, like the house got shot up and I remember, um, my father.

The house got shot up the first day you moved in?

The first day we moved in. Yeah. And that was like the welcoming. And I remember my father like holding me and my sisters down, like, while, you know, like they threw rocks and, you know, shot at the windows. And that was, yeah, that was like our welcoming into the neighborhood.

Yeah. And you remember this?

I do remember that.

Like vividly?

So this happened when I was like 4 or 5. And so we spent maybe like 1 or 2 years hopping around houses. And before we moved into this house that I spent, you know, from 5 until, you know, 17.

I guess when you're in a situation like that, I assume your dad is just like, we're just going to make it work. Like, you know, this is our only option, even though it's, it's obviously clearly unsafe to live there.

Yeah, I think when, you know, you come across like that and like, you know, he was working as like both the pastor and he was working at like restaurants, you know, he didn't make more than like $50,000 a year. He had like 4 kids to raise. Like, he can't just, you you know, even like get a mortgage, you know, or anything. I remember the house that we moved into is actually built for us by Habitat for Humanity. And so I've got a special place in my heart for that organization. And so between like having the house built for us and just very limited resources, there's really just not a choice.

And so you're growing up as a teenager, you're in a good school. What's schooling like? Like what's life like? What's your friend group like? What's going on in your childhood?

Yeah. So, you know, while the neighborhood I lived in wasn't great, my my parents made a pretty good decision in sending us all the way across town for school. And so I spent pretty much my entire youth, like, all the way on really like the white part of town, you know, going to school, going to church, etc. And so I was like the token Black kid for a very long time. I mean, like, all my classes, I was, you know, the only colored person. Wow.

How did that feel?

I think it was difficult. I just always felt that I stood out and didn't really have a place. And I think even as like, as children, like you recognize people that don't look like you. And so people naturally bully and things like that.

And so children are the worst too. Like, oh yeah, I would say anything that comes to mind.

Um, but you know, the education was really great.

And did you do well in school?

I did, uh, surprisingly so. Uh, my father was very strict, uh, because of the neighborhood that we lived in. And on top of that, being not only a pastor, but a first-generation immigrant. If you ask any first-generation immigrant, um, especially if they're in a bad neighborhood, we got our asses beat for anything. Uh, if I cursed, if I got, you know, nothing but— besides a perfect grade, I fell asleep in church. Yeah. You know, if I tried to braid my hair, you know, anything that was outside of the norm.

Why is that? Like, why? Where was that coming from?

I think it's a, it's a few different things. Like, one big cultural difference I have from you know, like my parents and really first-generation immigrants is that there's a really strong sense of cultural, not just identity, but conformity. Like it's really strong pack mentality to the point that self-expression is really looked down upon. So the way that you dress, the way that you look, you know, long hair, jewelry, all these things are not things that you want to deviate from. You want to be like a good member of the tribe. So I think that's, that's part of it. And then two, in most of these countries in Africa, if you have braids or long hair or any tattoos, you're associated with gang members. And so African parents interpret really any self-expression as deviance.

You made a comment the other day where you said, um, your dad was the only person who could tell you what to do. Talk about that.

Yeah, I mean, he was just really strict. He was very strict. And, uh, to the point that I feared him. Like, I deeply feared him. Um, and yeah, I just, I just, I never wanted to get in trouble because, like, it meant violence. Um, and so later on when he left, I didn't have that fear of, you know, corporal punishment. And so I rebelled very, very hard. I was like, no one else can tell me what to do. And by that I mean no one else can beat me.

What does rebel look like in Isha's world?

I think there's a lot of things. You know, one, I was really angry. I was very angry. Just like, you know, I didn't have really my parents. You know, my father had left, my mother She was deeply ill. She had manic schizophrenia and, you know, a lot of other health issues like diabetes and things like that. And so she was just constantly medicated, just in the basement sleeping all day. And so I didn't really have figures to talk to about anything going on. And so I was just really angry and frustrated at my circumstances. And so, you know, rebelling, I was like angry. I'd lash out at school. I was kind of like a class clown. Would pull pranks on teachers. Yeah, I would just get in trouble.

And so did you finish high school? Did you go to college? Like, what ended up happening?

Yeah, so I finished high school and I decided not to go to college. At that point, I was very, very jaded with school and I just didn't really see a path for me, you know, continuing school.

Why were you jaded with school?

I think I just, I wasn't happy, you know, at home. I had left, you know, my house and I just didn't really see a path for me. I started doing job shadows. I started visiting colleges, not because I wanted to, but because, like, the few adults in my life were like, you have to, like, you can't just, you know, end up on the street. And as I looked at, like, different jobs and careers and schools, it just— it deeply frustrated me that this was going to be my future and that I had to put in more years. I just couldn't see myself sitting in a cubicle or sitting in a classroom for any longer.

So in your, in your mind, like, what is the alternative?

You know, the thing is, like, I didn't have any role models. Like, the only role model that I had was my dad up until he left.

Like, no fictional role models? Like, no one that you'd even, like, picked up from childhood that you're like, oh, wow, like, I, this guy seems cool, or this girl, or what, you know, whatever it is.

Yeah, I mean, in my neighborhood, like the only people that we looked up to were like rappers and basketball players. And, you know, I wasn't going to play sports and I didn't rap.

Wow.

And so the first person that really inspired me as like a— I don't want to say young adult because I was a teenager, but like as a teenager was Alexander Supertramp. So I read and watched the book and movie Into the Wild with a friend of mine, my then best friend in high school. And Essentially this guy who has a deep resentment for society and just wants to escape into the wild. And so he takes a backpack and sets off to Alaska and hitchhikes all the way there. And unfortunately he dies, but you know, up until that end, and even with that, I was like, I was like, that's the coolest fucking thing.

If you're going to go, you might as well.

Yeah.

Have you seen that movie?

I haven't. Have you?

Really good.

Okay, nice.

We made us watch that in English class for some reason. Uh, really good.

It's great. Yeah.

He gets all these offers. Like he gets into Harvard, right? Is that what it is? Like he is, I remember him, he, there's a scene of him sitting down with his parents and his family and he has like this path for him. That's like every, you know, conventional person's dream. And he's like, I don't want any of that. He's like, I'm going to like sell my car. I'm going to like literally move and like go into the forest.

I should go back and rewatch it.

Yeah. It's inspiring. Cause he, um, he's just like detached from everything that I think society places so much value on and just like does his own thing. Granted, he dies by eating poison berries, but not to spoil it for anyone who hasn't seen it.

Kind of ironic. And so, so you watch this film and does this inspire you? Like what, what goes, what happens after?

Yeah, I was like, this is the only thing that makes sense. I was like, nothing else makes sense. And, um, so maybe 6 months, uh, 6 to 8 months, probably 6 months before I graduated high school, I was like, this is what I'm doing. And so, you know, I told everyone.

What is this?

I'm just gonna backpack around, you know, the country. I'm just gonna hitchhike. I'm gonna travel.

And your friends are all going to college.

They're all going to college. Yeah. So how does it even start?

Like you just literally step outside your door, got a backpack on, just put your thumb up? Like, how do you actually go from where you were at to trying to travel?

It's interesting. So I like, I bought like a ton of stuff off like Craigslist. And so I had like a backpack, I had like a tent, I had all this stuff. And so I'm with some family friends all the way in Massachusetts. And up until that point, like, I was so set on it. I was so convinced this was the path for me. I had no fear. This is the path for me. Then one day, you know, I set out and I get maybe a block away and I just start bawling. I just like start crying. So I realized I was like, I didn't have a phone, you know, at the time I didn't have internet, no smartphone, no laptop, no nothing. And I was like, where am I going? I just knew I was heading west. I was Massachusetts and I was going to California. So it's like, how am I going to get there? That's crazy.

So wait, you set out, you're like, I'm going to California.

Yeah. Yeah.

Could you imagine?

I cannot even imagine that.

Wow.

Yeah. So I just, I just started bawling. So I was like, oh man, it like, it all hit me all at once. And it's one or two blocks away. And, you know, I, I just have to figure out what I'm doing. I realized like, man, like I actually don't have any food.

Was your family supporting you?

Forgot the food.

You forgot the food. Was your family like, yeah, we support this?

No, they hated it.

Okay. They hated it.

They hated it. Everybody hated it.

Even you kind of hated it.

Yeah, I mean, up until that moment.

You really are living this Into the Wild journey.

Yeah, I just, I didn't think it through. Yeah. Um, but I think that was really, it was, it was a great experience because like, you know, I cried while I walked, but then I had to figure it out. Like my backpack was heavy and I had this like really big guitar and the case was super heavy and like my arm got tired after like 3 or 4 blocks. I was like, I can't.

3 or 4 blocks?

I was like, I can't case California.

Right?

And so.

What'd you do with the guitar?

I found a pawn shop, um, and I was like, man, actually, so at that point I didn't even have a tent.

I thought you said you bought a tent.

No, no. So, so right here. So I go to a pawn shop and I find a pawn shop and I sell, cause I have a really nice guitar. It's like this, uh, really nice Fender acoustic guitar. And so I sell it and they give me like a few hundred bucks. And then while I'm in the pawn shop, I buy a tent and a sleeping bag there. Um, and then I use that for a very long time and I buy, you know, some supplies and then, you know, I got some cash on me.

Yeah.

You know, I find like a grocery store, you know, get PB&J.

What is the feeling you like, are you excited to be doing this? Are you like, oh my God, freedom. This is the greatest thing ever. Even if it means I'm gonna sleep on the ground.

Oh, totally.

Really? Okay. So you're like highly motivated. This sounds like an epic adventure.

It was terrifying for like an hour.

Yeah.

Yeah. That first hour sucked.

And you're like, wait, no, this is right.

Yeah. I was like, this is what I told myself I was going to do.

Have you ever felt called to do something like this?

Uh, no.

And you? Uh, No, I don't think so. Maybe like, maybe when I was in like high school living in Montana, but, but, but, you know, to the degree that you've, you've done it, I do relate with you on the taking the unconventional path.

But I think that regardless of the path you choose, it's the— if it's unconventional, there's like the conventional one and there's the unconventional one, and you pick the unconventional one. And I think I relate on that level and that I just didn't do what everyone else was doing with all the pressure and the people around you saying, you got to go to school, you got to do this, you got to do that. Fortunately, both my parents were very supportive of my journey. But I think that a lot of people around me were looking at me like, oh, like, you know, what's he doing? Is that the right decision? Or he'll, or he'll just give— he's going to do this for a month or two and then he'll be right back with the rest of us.

Yeah.

Yeah.

It takes a lot of courage.

Yeah. And then a lot of idiocy too. True.

You got to be a little irrational, a little, a little kind of like deer in the headlights.

I think the thing that I learned, you know, through that is that Oftentimes, like, you don't know what the thing that you need is, but you know what you shouldn't be doing. And so oftentimes, like, if you're— whether you're like, you're, you know, like traveling or trying to find a job or you're an entrepreneur and like you're trying to build out the path, like you can look at something like, nah, this is all wrong. That doesn't mean you have the answer. Right. And so oftentimes if you don't have— for me, I didn't have a good influence. Like there were no entrepreneurs where I was at. I had to go out and find that thing. And so there's some exploration involved. But I, I just know the feeling of going to college and, you know, putting it— that just— it— I was so repulsed by it. And I was so aligned. I felt so free doing this thing. It was just this huge weight off. Like nothing else felt more.

So how long do you end up hitchhiking for?

Yeah. So I travel for pretty much like 2 and a half years. I do—

What years are we talking?

This is from 2010. 2010 to 2012.

2 and a half years.

Yeah. And so I do settle down for like months at a time, you know, here and there. For the first stint, I did like 6 months nonstop. Took me about that long to get to California.

And you're living off of like how much money? Like a couple hundred bucks?

When I left, I had $0. And then I just had my guitar and I would play music on busy streets. Would that work?

People give you money?

Yeah, I got really good at it. When I left, I had a terrible voice. And then after, you know, a few weeks of singing regularly, because I'd sing to myself, um, I developed like a pretty good voice. And if I was in like a pretty busy place, like I'd make, you know, $100, $200 an hour and I could do that.

Yeah.

Yeah. Whoa. Yeah. And so I get—

but you sold the guitar, so you ended up selling the guitar and then buying a new guitar, getting a cheaper guitar.

Wow.

So you were, you were pretty crafty though. You're like, I, I can sell this expensive guitar, get a cheaper one and a sleeping bag and a tent.

Yeah. Yeah. Yeah. I felt like I was on some RuneScape stuff. Yeah.

I was going to say, this is like Yeah. Matt could talk to you about RuneScape for a long time.

Dude, RuneScape was my shit. Yeah.

He was hitchhiking while you were playing RuneScape.

I was indoors, air conditioned, playing RuneScape. He was living the real RuneScape. You were living RuneScape.

Yeah. Yeah. That's really funny. I remember thinking that to myself a lot. You know, it's cool.

It kind of gamified it.

They kind of based the game on me.

Yeah. Wow.

Okay.

So I'd go to pretty big cities. I'd go to like the downtown areas or wherever there's like the most traffic. And then I'd play. And granted, it really depends on the time. What I found worked really well was farmers markets. And so if I was in a city for, you know, 2 or 3 weeks at a time, I'd figure out where the farmer markets were, play at those. Yeah, I only had to play maybe twice a week and then I'd have everything I needed for, you know, several weeks.

And were you comfortable just getting in front of a bunch of people and playing guitar? Like, was that just natural to you or did you have to work some courage to be able to just do that? When I started, I couldn't absolutely Absolutely not.

Yeah.

But then something motivated you, right?

Like, clearly I love music, you know, I think like music, music at the time, like, became my life is the only, the only thing that really made sense to me. Wow.

Did you consider yourself to be a musician at this point?

Wow. Yeah, 100%.

Were you like, I'm going to be a musician, like, that's going to be my life?

I don't think I had a plan. I think that's where I was going for sure. And for a long time, like, music was just my life and how I supported myself. Thoroughly enjoyed learning about it. And so when I'd be in the middle of nowhere, I bought books on music theory and I would just, you know, read and teach myself new things. And that was my hobby.

Were there ever moments where you're like, oh, this sucks. Like, I just want to go back home.

I never thought like I want to go back home. I did think many times like I want a home. That's real.

Yeah.

Because there were times where I'd be out in the rain. I slept in caves, you know, I slept in abandoned cars. I slept in abandoned houses. Um, yeah. And if, if I was in like a city and it was like raining and my tent was terrible. So if I slept in my tent in the rain, like I would get completely drenched. So I'd be walking from gas station to gas station at like 2 or 3 AM, you know, just like trying to stay moving, you know, because if you're in the gas station, like you're walking around, like they won't kick you out. That for, for a very long time.

And then where does that journey end? Like when, when do you start to like truly settle down somewhere?

Yeah, so I decided, uh, it was late 2012 and it was a funny story. I had, um, snuck on a train from Oakland, California all the way to New York. It was Amtrak. They have a line that goes through it. And at the time I only had like $100 in my account. And so I sneak onto the train. Well, I walk onto the train, but then I hide in the bathroom. And I'm really in the bathroom for 3 or 5 days or however long it takes to—

Literally standing on the toilet or something, or?

Yeah, they're like these like small bathrooms and I just like move from bathroom to bathroom, like waiting, um, ensuring I'm safe.

You just spend all day in that bathroom.

Yeah. I remember getting a phone sometime in 2011 or 2012. It'd been a year or two at this point. And, um, I get hit with all these roaming charges and my account overdrafts. So I'm like negative $200 or something. I'm in shambles as like a 19-year-old with like no job. And I knew I couldn't play guitar there. I was like, man, like, I can't support myself. And I've just been doing this for too long, like way too long. I don't know what I'm going to do. And it's funny because it's only like 15 minutes. It wasn't that long. I walked around really scared and confused and then something just kind of snapped and I was like, all right, Enough. It's time for the next stage of my life. I need to take control of my life because I've been, you know, even though I'd been supporting myself, you know, I was living off the goodwill of others, whether it was hitchhiking, you know, someone letting me take a shower at their place, busking, playing music on the street. I wanted to have ownership of my life. And so I thought about it really not that long. I just thought about what I wanted and just kind of like the constraints. And I knew that I couldn't have a relationship between my time and my income because I had done all these minimum wage jobs, like herding cattle.

Can you explain that? Like, what do you mean by that?

Yeah. So, you know, over the course of, you know, my travels, anytime I had a consistent job, like not just playing music on the street, like a consistent job, you know, I'd essentially make like $4, $5 an hour. and it would take a long time to be able to really get ends meet. Uh, and yeah, for anyone that's like worked minimum wage or close to it, you know, you just, you can't support yourself and it's really exhausting and you spend so much of your time and energy just like trying to stay above water, just barely stay above water and you can't really do anything meaningful. Um, and so I knew that I couldn't do anything hourly. Right, that I needed to create something where my income was not tied to the time that I put in, right? It's tied to like the value that I created.

Is that instinctual for you or did you read that somewhere or did you just kind of know?

At the time I just reasoned it. Yeah. Then I knew I couldn't. I was broke and I didn't have any money.

But I think so many people who are broke would just say, I'm just going to get a job, I'm just going to work harder. But you clearly had— you could distinguish what working harder meant versus working smarter, right? That, that, that wasn't obvious.

Now thinking about it, there was one person that really, really inspired me, um, and helped me think, uh, like as a reference at this point, this became like a role model. And, um, during my travels, I came across this guy, Mohamed, Mohamed Hafez. To date, I still love this guy. He's so cool. Shout out, Mo. Um, I met him in 2010 when I got to Santa Barbara. And when I first met this guy, He was living in a bus and he comes out in robes, right? And I remember thinking like, who's this like homeless guy? But he was so funny. He was so cool. He was like so down to earth. I get to know him and turns out like he's an engineer. He's a software engineer, software engineer, and really kind of like built a life for himself and like, you know, built apps and all these things. And, and another story now, he's like, he's killed it off of, you know, this app substitute that he built years later. And we've stayed in touch over the years, but I remember thinking, you know, he was able to build a life for himself as like a software engineer. And while he was working hourly at the time or salary or had been, I knew that you could create a life for yourself like as like a software engineer. I was like, this kind of makes sense, but I didn't want to work for a company, right? And so I knew that I wanted to be able to continue traveling. And so not being tied to location. And so I was like, you know, software checks off that box. I didn't have any money and I didn't have anyone wealthy in like my family or anyone that I knew. So I needed to be able to do without any startup capital. And as I thought about everything, I thought about everyone that I had come across. The only thing that made sense was being a founder of a software company. So I was like, I'm going to teach myself how to write code.

So this guy inspired you to want to become a founder of a software company?

Yeah, yeah, yeah.

And so you're in New York, you're kind of, you've overdrafted, you're in this tough position, you've had this 15-minute, like, revelation, and you're now thinking about wanting to start a company. How does that, where does that begin?

Yeah, so I started thinking about ideas. Um, well, first I needed to get a laptop. Um, I had no money. And so I got a job on Craigslist. I found a guy in New York who, he was kind of like an Amazon wholesaler. And so what he would do is like he would get all the stuff wholesale and then he would pay me like $5 an hour, $6 an hour to break it down into smaller boxes, put labels on it, ship it out. And so I started working for him a few days a week. I, after the first like 2 or 3 days, I had like $100, $150, took that, went to Craigslist, got like a really cheap Dell laptop. and I continued working for him for a few months and I'd work, you know, 6, 7, 8 hours a day and then I'd go to this Dunkin' Donuts down the street and I'd be there, you know, 6, 7, 8, 10 hours. Um, got a membership to, lynda.com, uh, which was, has since been acquired by LinkedIn, but is like the Udemy.com of like that time.

Like a learning platform.

Sure.

You could like learn anything on there or just program?

Everything.

Everything.

Wow. Yeah, yeah. So, you know, got a subscription and started teaching myself HTML, CSS, JavaScript and, um, at the time I didn't have any ideas, but I was like, I know this is the direction that I need to go in.

Were you pretty naturally good at that? Like, so obviously some people can write code, others can't. Like, did you—

I tried like 5 times, 5 separate times to try to teach myself. Just gave up every time.

Yeah, me too.

I just, I couldn't get into it. It was just wasn't natural for me.

I was good with HTML because I would edit my MySpace layouts.

Okay.

And I was like, that was how I would get like scrappy. I'd like be hiding things on my MySpace and stuff and you have to go into the HTML to edit it. but anything past that, I was like, oh, this is like one level too deep for me.

Totally. It just, it felt like that was not what I was put on this earth to do or be good at. And so I just realized that like my, my skill strengths, whatever, are better, better elsewhere. But, um, was it obvious to you? Like, were you intellectually stimulated by the idea of learning programming? Like, did you pick it up pretty quickly?

Yeah. So, you know, one, one other detail is, um, like I did, I did really well in school. Like I was in all honors and AP classes and I really got pretty much all A's with the—

while still being like this rebel. So you're like pissing off the teachers, but then you'd like go collect your like A+.

Yeah, I did really well.

Wow.

And I remember I did all these AP exams, but I never checked the scores because I was like, I'm not going to college. Right. And so when I was trying to decide this, I had taken computer science and I remember really enjoying it. And so I emailed, I found the email of my high school teacher and I was like, hey, do you, do you have like my AP, you know, scores? I'm just, I'm just curious if I was like good at this. And he sent them to me. He's like, man, you got like nearly a perfect score. And I, and I remember we had to do it by hand too. Like we'd have to, um, and so I remember I thought about it when I was, you know, thinking about this. I was like, man, like I was good at programming and I enjoyed it. I remember building games and like all these things. And so I was like, along with, like, the lifestyle that I want to build. You know, I think I have a predisposition to this. Let me try this.

And so there were some signs.

There were some signs. There were some signs. And so I remember I actually waited probably 2 or 3 or 4 days until, like, I got that email and I saw this and I was like, all right, cool, cool. So got the laptop, started teaching myself HTML, CSS, JavaScript, probably like a month or two before I was, like, decent enough. And this was, you know, working like 7 days a week. at least on the courses. And after like a month or two, I was like decent. And, I started working on ideas.

And what was the first one?

Uh, the first one was called Jailbreak Mecha, jailbreakmecha.com.

Like jailbreak your iPhone?

Yeah, yeah. So back in, uh, this was 2012.

Did you ever jailbreak your iPhone? Wait, you're jailbreakmecha.com?

Holy shit. Must have been like one of two people that visited the website. Really?

I actually think I might have went on that website.

It was like the thing at the time. Everyone was jailbreaking their, uh, their iPhones and So I was like, yeah, this, this is really cool. You know, I was jailbreaking my iPhone. And so I put together a website with all of the cracks and instructions and everything. And yeah, put the website up and then I put ads on it from Google Ads Manager, you know, whatever was going on at the time. And I remember it took me like a month to work on the website and I was so convinced I was going to be a billionaire. I was like, this is it. Really? I'm going to be swimming in it.

Wow.

Everyone's going to be jailbreaking their iPhone.

Like as soon as you published the website, you just thought the money was just going to flow in?

I pushed the website and I was like, Calm. Calm.

I totally relate. Have you had that feeling?

Many a time. Many a time. I'm like, oh, this is it. Yeah, I should just— this is it. That's all I have to do.

That's it. That's it.

And then you're also looking at the world like, oh, it's so easy.

You're like, why can't everyone else do this?

No one else figured this out. It's so easy.

I've cracked the code.

You get humbled very fast.

But, uh, yeah. So I put on ads and I think I made like 3 or 4 cents. Let's go.

In a day, a week, a month?

Probably throughout all time.

All time? Okay.

I spent more on hosting. Yeah, yeah.

Got it.

Got it.

I was like, damn, I'm overdrawing again.

So, you know, I think the interesting thing about that is, uh, that was the first of many quote unquote failures, which I didn't even see as a failure. I was just like, you know, I learned a lot, you know, and it didn't, you know, hit. Um, and I never thought to market at the time. And so I was like, I'll just build the next thing. But like, I didn't tell anyone about it. Like, I didn't, you know, I was like, why aren't they coming?

Yeah, I think as when at younger ages, we don't recognize the value of distribution. We don't understand what distribution actually means. We sort of just think if we build it, they will come. Yeah, but we have to learn distribution by trying, right? Otherwise it's not, it's not intuitive in that way.

100%. Yeah. I often say that I spent the first probably 2 or 3 years of my career learning how to build products, which is just, you know, writing code, architecture. And I got like really, really good, you know, down this path. But then I spent all the years after that learning how to build companies, which has much more to it than just the thing that you build. You have to tell people about it. You have to iterate on it. You have to like build a team. You have to build culture. You know, you have to set pricing. Branding.

So you're tinkering with these ideas, you're hanging out at Dunkin' Donuts.

Yeah.

Let's talk about how you meet your co-founder. How does that happen?

Yeah, yeah. So I love my co-founder. We've been friends for 13 years now. So I met him, I met him in 2012. So this was when I was still doing my vagabond stuff. I was an avid chess player, loved to play chess. I had a chessboard and I used to travel with it and I would often sit at a coffee shop and just like put up a sign. I wanted to kill time and encourage people to play me.

The guitar, this is a theme here. Yeah, yeah, yeah.

Walking the streets.

Oh, um, I kind of built a reputation for myself in Santa Barbara. I was living in Isla Vista, um, at the time. It was like a college town.

Isn't that the college town that's like insane?

Oh yeah.

Yeah, it's like insane. You know about Isla Vista?

No, totally not.

Oh, it's actually crazy. It's like a, actually you should tell us, what is Isla Vista-ish?

I don't remember the year, 2011.

Got it. Like, imagine an island that's literally just college kids.

Wow.

It's the entire— everything is run by college kids, right?

Yeah. It's crazy. I forgot children and adults existed. It was just such a bubble.

And everyone's just partying constantly?

Just partying constantly. Just drinking and like surfing. And that was like, that was my life for a while. Wow.

So, um, I did not know you lived on Ilovestad.

Yeah. Yeah.

Sounds awesome.

Great times. Great times. Yeah, I found that. I was like, this is paradise. I'm never leaving.

I made it. I don't need to be a billionaire. I can just live here.

And so, you know, I hung out in Isla Vista for a little bit and it actually became my home base while I travel and come back. And I'd built kind of like a reputation for myself because I'd play and I would, I'd always bet when I play people. And I would say I'll bet anything but money, um, also because I was broke, but it was also interesting. Um, and so at the time I would bet small acts of humiliation.

Small acts of humiliation.

Yeah. Okay.

What would be an example of that?

Um, for example, like if I, if I win, I'm going to put you on a leash and, uh, take you to the park and walk you around in front of everyone.

Wow.

And you did that?

Oh yeah. Great.

Yeah. How many people did you do that with?

Dozens.

Yeah. There's a different podcast we should do talking more just about that, but.

Yeah, yeah, this is great. Um, and so, uh, dozens of people you walked around a leash. No, no, it was always, it was always a different thing. Um, but like all equally humiliating.

Okay, got it.

I had a friend shave his hair, had a friend like break into someone's house.

Oh man.

Wow. It's crazy. I was like 18. Um, so I'd kind of built a reputation, you know, for this. And, uh, my now co-founder also lived in Isla Vista at the time. Uh, he was an undergrad and, uh, he was throwing a house party. So one of the guys that I had beat gives me a call and he's like, hey, you know, I'm at this guy's house and we're playing chess and, you know, he's just, he's talking a lot of shit and being like really cocky. You should come over here and like show him what's up. I was like, that sounds like fun. Isle of Vista is super tiny. It's like 1 square mile. And so I look up the address and it's like 4 blocks. Yeah. So I grab my skateboard, go over there, you know, walk in and it's one of those towns, like everyone's door is open. You can just like walk into like any place. I walk in. He's like, "What's up, man?" And I was like, "Hey, you know, I hear you guys are playing chess. Yeah, can I play?" And he's like, "Yeah." I was like, "Well, you know, I came all this way. Let's make it interesting. Let's bet something." So we decided just like on a 6-pack of beer. Yeah. So I beat him. He's like, "Double or nothing." Yeah, beat him. Double or nothing. Beat him. Double or nothing. Beat him. So we're at like 48 beers and he's like, "Double or nothing." Okay, he's hammered at this point. So we're playing shot chess. So it's every 3 points you take a shot of soju. And like, I'm beating him. And so it's getting easier for me. And so every, you know, 3 minutes he's like, double it up. I'm like, hell yeah, let's go.

And, uh, so how far does this go?

So, you know, after like 48 beers, um, you know, I was like, let's, let's do other stuff. So I take a guitar amp and I start taking random stuff and he has this like really nice guitar and I was like, that guy. And, uh, his, uh, roommate at the time steps in. It's like, no, I like, I can't let this go on. Uh, so. I remember taking the guitar amp and leaving, and I give him my contact info. I was like, hey, if you want to give me the rest of the stuff, here's my info. If you don't, like, that's cool too, you know, I'll catch you around. And so he hits me up a few days later and he's like, hey, I think, you know, I owe you some stuff. So he comes over and brings all this beer, and I was like, hey, you're pretty cool, man.

Wow, that's pretty noble for him to just, you know, take it on the chin and show up with all the stuff.

Yeah, he's super cool about it. He wasn't salty or anything.

He just kind of like an interesting early signal for a future co-founder, right? Like the kind of person that would do that is probably somebody with some values of sticking through what they commit to.

I will say, I think to date he is probably the most high-integrity person I know. Like he is.

That's what I mean, is a high-integrity person would do that.

Very much. Very much. Yeah. So he's an inspiration in more than one way. Um, but, uh, yeah, so that, that happened in 2012 and then independent at the time, neither of us were like writing code or anything. Um, so fast forward like 2014, like 2 years later, and we're friends on Facebook. I've been programming for, you know, 2 years at this point. I guess he got into it and he transferred to UCLA. Uh, he recognized Santa Barbara as a joke, I guess. It was like, I need to do something with my life. And, um, so he transfers to UCLA, uh, joins Bruin Entrepreneurs, and, um, or actually starts Bruin Entrepreneurs.

Um, and the Entrepreneurship Club UCLA.

Yeah, yeah, yeah. So he's, uh, he's one of the founding fathers and they put on the first LA Hacks, which was, you know, like the biggest hackathon at the time. Um, and he was posting questions on Facebook about this website. And so I'm just answering and eventually, you know, I DM him and I was like, just, you know, send me the website. Yeah, I'm happy to do it. He's like, you sure? And I was like, yeah, I'm just, I'm really focused on learning right now. This is aligned with, you know, the things I'm doing. Just, you know, send it over, tell me what you want. I'll do it for free. So I do the website, send it back, and then he invites me to the event. At the time, I actually went back to Nebraska this time, and I had a— I was staying with some family friends because I told them like, hey, I need to just lock in for a little bit longer. And so I'd been in Omaha for a little bit, and I start working. I do this website. He invites me to LA Hacks, and I was like, oh, but I'm not a student. This event was for students only.

To participate in the hackathon.

To participate. And He's like, well, I'm the organizer and you built the website, so, you know, come on out. So I get a ticket, I fly out to Los Angeles, and suddenly I'm surrounded by, you know, 1,000, 2,000 kids who are all hacking and writing code and staying up until, you know, 5:00 AM working on all these projects. And now I was like, this is the coolest thing I've ever seen.

These are my people.

These are my people. All this Red Bull and no deodorant. So I moved to LA like probably 2 or 4 weeks after that.

Wow. You were so like, this is it. This is my place.

Yeah. Yeah. I'd been locked inside for so long while I was programming. I continued to travel for a bit. You know, I moved to Oregon, you know, I moved, you know, to Santa Barbara for a bit. I was traveling around like hitchhiking and teaching myself, you know, how to code still. And like, it just wasn't great. And so at this point, it'd been, you know, a year or two of traveling or a year or two post deciding to be like a software engineer. And so I, you know, call my folks and I was like, hey, you know, I want to teach myself how to code. I don't want to go to school. I want to teach myself. I just need a place that I can lock in for a little bit. This is, this is my future. And so like, all right, come on home. And so, you know, I go home and I was in Nebraska for a little bit before this, this happened.

And so you do this hackathon, you move to L.A. When does Company One form?

Yeah, probably like 2 months after that.

Okay. So your entrepreneurial bug is kicking still. You've got all these ideas. You've met this person who invited you and welcomed you to this L.A. kind of hackathon community. And now, yeah, talk about the formation of the first company.

Yeah. So, you know, I moved to L.A. and pretty much every weekend I spend in Venice at my now co-founder's house. We're really just like writing code and like we're building all of these things. We're building mobile apps, we're building websites, we're building programs.

And like an idea in mind, like, let's get rich doing this. Or like, what was the kind of like—

it was like we were just like hacking things that were interesting to us. You know, we started taking on like freelance work, you know, so people were paying us to build like their ideas. And I realized I was having so much fun. I was like, I love— like, we would be up until 3 AM, like, writing code and, like, drinking and, like, laughing together. We're all, you know, 20, 21 years old at the time.

And just you two?

Um, there was actually a lot of us.

Oh, wow.

Yeah, we built this, uh, this community. And so, like, the house would have, like, 10, 15 people in this cramped apartment.

No way.

It was so fun. Um, and so I looked forward to it every weekend. Uh, every weekend I would, I would go to this house and I just crash on the couch and we just hack stuff. And after, you know, maybe 2 months, he's like, we should start a company. And I was like, yeah, 100%. Like, doing this? He's like, yeah, an agency. I was like, done. I was like, but I don't have a place. He's like, stay on my couch. I was like, done. And so, you know, I think like a week later, you know, I moved on to his couch and I stayed there for, you know, 6 months and we built this agency, Ctrl+LA. and that was, that was my first like real company.

Company is an agency that makes software for other small businesses. Are you guys just like selling to nearby folks that need it? Like how, how did you build this?

Yeah, so this is around 2014. Um, this is 2014. And at the time everyone and their mama has like an app idea, you know, like Uber for X, Tinder for X, you know, it's like we're going to take Tinder, but like for dogs and they'll pay us, you know, $50,000, $100,000. So we're like, heck yeah.

Or like Uber for pizza.

Uber for pizza. Uber for photographers, you know, whatever.

You don't care what it is. You're just happy to get paid.

There were some that we didn't do because they didn't align with our morals. But, you know, generally, like, as long as, you know, it wasn't—

Tinder for dogs.

I'm trying to hook them up. And it was a lot of fun. And then so primarily startups, but, you know, we sold to, you know, larger companies as well. We were able to build stuff for Universal Studios. For Uber, for a number of celebrities. And it was great, like really learned how to, you know, sell, how to, you know, negotiate, you know, build contracts. You know, we built a dev team.

How did you guys divvy up responsibilities? Who did what?

So we were all technical and so we were all, you know, writing code at the time. I was primarily backend and he was in love with iOS. And so he did like the frontend in Swift.

But who was like selling and pitching these clients?

He's naturally good at pitching. So it's interesting. This is our second company together. We've never ever had a conversation of like who's CEO and who's CTO. Never had that conversation. Really? To me, it just made sense like that he's a CEO and it just made sense that I'm the CTO. Got it. And yeah. And so I'd watch him sell and I was like, he's great at it. Yeah. And so I was like, this, that's just what he's supposed to do.

That's the best when it just works. It makes sense.

Yeah.

And so you do this agency and then how do you end up at Paragon?

Yeah, so, you know, we built the agency and what we wanted to do, like our vision for it was to essentially get paid to learn. We were having a lot of fun getting paid to learn how to build stuff, but eventually we wanted to build a SaaS company. And so we were friends with a lot of agency founders and there's this running joke that every software agency or marketing agency, the founder really wants to build SaaS. That's like their, their dream. And so we're waiting for the right idea to hit. you know, get some, uh, enough like revenue where we could bootstrap it ourselves. Um, and after maybe 1 or 2 years, I came down to like a few ideas and one of them was an email client. Um, and, uh, that was like the running idea. And, um, I thought about it and that just, that wasn't the problem that I wanted to work on. And so we went our separate ways. I continued to run the agency and, uh, uh, he, uh, ran this email client, but we stayed really good friends. We lived together, you know, I wrote some code, you know, for the company Polymail, actually really, really well-known mail client. They went through like YC back in summer '16, I think. And so we stayed like really, really good friends over the years, continued to travel together, you know, dinner, you know, whatever. I continued working on the agency and from 2000, maybe '15, '16 until 2019, I would, I was still looking for different ideas to work on. During this time, I probably worked on like 100 different ideas. Wow. Um, you know, I'd get paid to build these apps and all the while I was trying all these different things and learning a lot. Um, but I also kept a list of people that I wanted to work with. So as I, you know, sold to businesses, as people, um, came to me with different ideas, as I made friends with different founders, engineers, etc., I built a really, really huge Rolodex of people, uh, in LA.

Yeah, it's actually a fantastic way, honestly, to start a startup is to start an agency like that because you're attracting and, and I mean, all sorts of interesting people. You get all these ideas, you get to work on your own ideas, you become a better engineer as a result. You're just getting so many reps in and building such strong intuition on like what works and what doesn't. And then you're also getting money in the door where you can like start your own thing. Like you don't even have to raise if you don't want to.

Yeah.

And I think you put it really well, getting paid to learn. Like how awesome is that?

You get to figure out what you what you like and what you don't like.

You can choose to take on jobs or not, or whatever.

So I will say, like, at the time while I was doing it, I was like, this is 100% the best thing I could be doing because I'm meeting so many people, I'm getting paid to learn, etc. In retrospect, now having run Paragon for, you know, 6 years and some change, I have learned more in every year of Paragon than I have in that entire 5, 6 years of consulting.

No way.

Yeah, it's like when you're working on like really, really big ideas, you just, you learn so much more, even if it's the wrong idea. Like you learn more.

The velocity of learning.

Yeah. If I could go back in time, I would have done it for about 2 years instead of like 5 or 6. And then I would have just started working on venture ideas.

We didn't even really talk about this, but like you also now are making a salary and you're like probably living much more comfortably than you were. Is that— was that like, did that make sense to you or were you kind of like, whoa, I actually can afford to eat where I want to eat now and fly to where I want to fly? Like, what was that? Just even that like change in your like financial life like?

Yeah. So that, that was, that was a huge change for me because growing up, I never traveled, right? I didn't eat good food. I never went to restaurants. I remember being like 20 or 21 years old and I was with some friends and we were at a restaurant and like the waiter asked like, how do you want your steak? And I was like, what do you mean?

Just like, I just want it.

Yeah. Like cooked. Yeah.

Yeah.

I just, I never had, you know, I never had sushi growing up. I never had, you know, steak and And so suddenly, you know, I'm 21 years old making six figures. Like, I balled the fuck out, you know? And so I start traveling, I start eating well, you know, I'm buying flights last minute. Like, man, it was just a completely different life. Like, I'd like, I bought everything on Amazon that I saw left and right. I didn't—

How'd that feel?

It felt really good. It felt really good. It was freeing. Yeah, I felt like I was making up for a lost childhood. And yeah, and I didn't have to ask anyone, you know, for permission to buy something. I just, I just balled out for a very long time.

What are your parents thinking at this point? Are you telling them about this?

At this point, they're both passed.

Yeah.

And my father passed when I was 18. I found out while I was traveling and I hadn't seen him or talked to him in several years at that point. And my mother passed when I was 21. And so— I'm so sorry. Okay. Yeah. So unfortunately they didn't get to see, you know, um, what I made of my life.

You're living this life, you're making 6 figures, you're kind of balling out. For you, was that your ceiling or were you like, oh, I'm going to do so much more than this?

At the time, I'm still living in scarcity, right? Like I, I'm having a lot of fun, right? But I'm thinking to myself, this gravy train is going to stop at some point. I need to figure something out. Um, and that, I think that's why I kept trying ideas. You know, and I was like, I need to secure the bag. I need like a certain amount in my account if I'm, you know, to see tomorrow. And so while I'm having fun, I know that I need to do something.

Probably serves you to some extent to be thinking that way, right? To know that not like I need to get to this amount as soon as possible, but I need to build something that, you know, you can work on for like a very long time that can continually grow.

Yeah, I, to be honest, like, I think it took me a long time to get to that mentality.

Oh, really?

Yeah, for a long time, the mentality I had was like, I need to get rich quick. Um, you know, like, I need to squeeze out every dollar from this. Yeah. Wow.

And so your co-founder is building a different company. You're now co-founders building a different company. You're running this agency. At what point did you guys converge to start Paragon?

Yeah. So during my agency days, I built a really, really large Rolodex. and I would regularly follow up, you know, with people in like the top 50. And I had a rule that anyone in the top 10, if they ever became available, I would drop what I'm doing. And for co-founders, for co-founders, 100%. And, and so he was actually number 1 for pretty much that entire time because he constantly referred me so much business. I really enjoyed working with him. I trusted his judgment. And I had worked on so many things and experienced a lot of things. I trusted my own judgment. but I said for a long time, the only person that I would trust to start a company and be CEO besides myself would be Fu, right? And so, I was on the investor update list, not because I was an investor, but, you know, just because I was like an early user and, you know, good friends with, you know, the co-founders and all that. Um, and so I got an email that he was leaving the company. Um, so I texted him, you know, immediately and was like, hey, let's grab lunch. And so we get lunch and I give him an Airtable with like 100 ideas. And I was, I was like, this is every idea that I've been thinking about for the last, like, you know, year or two. We can work on anything. I just know if we work together, it's going to work. So didn't care about the idea. It was just the person.

Yeah.

Right.

And did you feel like, again, you just come from running this agency. Were you prepared to drop that agency for this if there was heat there?

Oh, 100%. Yeah.

That was clear to you?

100%. Yeah.

And was he ready to do the next thing?

He was. He was. He, uh, so I remember this was at the beginning of the summer. Um, and so you want to take like a little bit of a sabbatical. Um, so he did that. Um, but we met probably weekly and just talked about like different ideas. Um, and at the time, like, I, both of us were still kind of like co-founder shopping, but we knew both of us were our top picks. Um, and so as we evaluate different ideas and we looked at different opportunities where, you know, both were like, all right, like we're definitely going to work together. Let's just like pick an idea and let's do this. So that process was probably, you know, 2 months of us just like regularly following up with each other, touching base. Like, you still want to start a company, you know, you ready? You ready? You ready? And then—

so what is Paragon?

Yeah, Paragon is an embedded integration platform. So we sell to B2B SaaS companies and we are their infrastructure layer for integrations. So you could think of it like Zapier, but instead of for internal business automation, it's customer-facing. Customer-facing product integrations.

Okay, so explain that to me like I'm 10 years old.

Yeah. So our thesis is that every company today is a software company, whether you're a restaurant or a marketing agency or a traditional software company. Um, each of these companies use 100+ different softwares, whether it's like payroll, um, or like benefit software or payment processing software or internal company chat, right? Or, you know, Google Sheets, a CRM, whatever. Typically, as a company, if you are buying a software, uh, like maybe a payroll software, you expect it to integrate with the other tools you use. Um, so if you say buy a payroll software, you expect it to integrate with maybe like your benefits software, right? And if it doesn't integrate, that's going to be a strong reason why you might not buy that software. and so we sell to those software companies that want to integrate their products with other, uh, software, uh, platforms.

Cool.

So what would be like an example use case?

Yeah, um, these days, you know, we sell to a lot of AI companies. Um, so maybe, um, let's say, you know, you're, uh, an AI company and you're building an AI sales copilot, um, and you want that copilot to be able to talk to your, uh, your customers and figure out like what's in their pipeline, interact with like their Salesforce. Maybe you want it to interact with their calendar and, you know, book events on their behalf. And so those are like agentic actions. And our platform would manage those connections to your customers' Salesforce or calendars or other integrations. And we also equip tools for those AI agents to be able to take those agentic actions. We also do, um, we have a product Managed Sync, which is large-scale ingestion. So maybe you're building an enterprise search product and, uh, you want your customers, um, to be able to search things like across their Notion, across their Confluence, across their Google Docs, all that stuff. And so, um, your customers would connect their Google account, their Confluence account, their, uh, Notion, et cetera. And then it would ingest all of the pages and anytime there's an update, uh, you want to be able to automatically ingest that, um, and then, uh, index it so your LLM, um, has that context. And so that's, you know, another use case. Really cool.

And so tell me about the company today. How big is the team? How much have you guys raised? Like, give us the scorecard.

So we were founded in August 2019. Um, about 50 people right now. I've raised about Uh, $22 million in funding. Um, just got some very good news. Um, I'll— we'll be announcing it very soon. Um, but it's related to fundraising. Um, and so over, uh, really the next 3 to 4 months, we probably expect to grow to like 100 people. Wow.

Exciting. And sorry, did you say the revenue?

I forgot. Yeah, we're about to cross $10 million.

Oh my God. Congratulations.

Thank you. Thank you.

Um, it's great when it works. Yeah. Um, and so What have been, would you say, the takeaways now? Same co-founder, obviously. So what have been the takeaways from company 1 to company 2? Like, what have been the learnings from each one? If you had to summarize the last 12 years of your company building journey?

Yeah, I think the who is so much more important than the what. The problems will always change, you know, based on like the market, based on the timing, based on the positioning. And you should instead invest in the people who can adapt with you across those problems. Um, I know, I knew, and I still know that any problem, I will be successful with my co-founder. Um, we can navigate disagreements, um, we can think about, you know, the best path, we can divvy up responsibilities, um, we have high integrity, high ownership, you know, etc. We don't have to watch over each other's shoulders, we just know what to do and then it just gets done. Um, fun fact, we have one-on-ones, like, you know, once a week, probably like 15 minutes. Right? And, uh, we're able to completely run, you know, our departments just off of, you know, 15-minute conversation with him. Like a once-a-week 15-minute conversation. Wow. To me, that just represents like really, really high trust.

Yeah.

I don't have to, you know, look over his shoulder and see like what's going on. I just know that it's being done and I look at the numbers and I'm like, yep, up and to the right. So people over product, um, you know, work on hard problems, um, with the agency and all of most of the ideas that I worked on, like they were pretty small problems. Um, and one of the best pieces of advice I got was that no matter how big you're thinking, add a zero, at least a zero, maybe two zeros, probably two zeros. Um, and so that's like in terms of, you know, the TAM that you should target in terms of how long you might think it'll take to get there, how long you should be investing in the business. Um, people think, oh, like maybe I'll work on this for 3 months, maybe a year. And you should think, am I willing to work on this for the next 10 years? you know, is this a big enough problem space for me to work on in the next 10 years? Um, yeah. And, uh, yeah, just focus on big problems.

Um, maybe taking a further step, like, what do you wish you knew before starting Paragon, uh, that you know now?

I think a few things. I think, like, I made the right choice with the co-founder, but when I look back at, um, you know, the team, um, I wish I would have went with like more senior people early on and given more ownership and accountability to more senior team members early on. I think one of the mistakes I made was putting myself at the center, you know, so much. And it took me years of developing the skills of being able to like truly delegate and empower others. But once you put yourself in a position where you're not just an IC, an individual contributor, but Rather sitting up, you know, higher up and leveraging, you know, more people, you are able to accomplish much more as a founder because you have all these people who are, you know, working and thinking about a larger scope of things.

So for the founders that are listening to this right now and thinking about their assembly of their team, and they think, oh, we don't want to get somebody too senior because we worry they're not going to be like startup, they're not going to have startup shop. And I need to be in the middle of all this because I have to be product obsessed and customer obsessed, etc. What do you, what do you say to those sort of two pushbacks?

Yeah, I would ask like, you know, why do you not trust your people, right? Is it that like you made the wrong hires, right? Is it that you're too controlling? Is it that there's not enough process or the right processes in place where people are able to make these decisions? I have found that when you hire the right people, the things that you can accomplish that you will accomplish you would have never dreamed of. The things that they come up with, the impact that they have is beyond your wildest imagination.

Can you give an example? Here's what that looks like.

You know, our director of product, Ethan, he joined the company very early on within like the first, within the first really 6 months. And he started as a software engineer and he's now the director of product. And, you know, I credit him more than myself for our Series A, right? You know, he was able to talk to a lot of our customers and, you know, find this go-to-market that we pivoted to and this positioning that was a much, much harder problem than we originally arrived at. And yeah, like if it wasn't, you know, for his insights alongside my co-founder, like, you know, we'd be a very different company in a very different place. Yeah, there's, there's, there's a number of other people in the company where They've brought these innovations, have completely shifted our direction, our velocity. And I just, I wouldn't have been able to do it by myself because there's so much I'm already thinking about.

Yeah. Have you had any moments in your company where you have wanted to either work on something else or just shut the whole thing down? Like, when have, when have you felt like, damn, I just don't think that this is, this is the right path for me anymore?

I think for me, it's always been tied to my mental health. Right, based off of what's going on outside the company. When I look at all those times where I didn't believe in the companies because I didn't believe in myself, I had bad relationships, I didn't have the correct work-life balance, I wasn't eating right, I wasn't sleeping right, and so I wasn't thinking right. But whenever I fixed those, whenever I surround myself by the right things, then my approach to the company was fundamentally different. Yeah.

And I mean, just again, you've shared your story, but how do you think that that early childhood, that upbringing has shaped the way you think about company building? Like, were there lessons from your teenage years when you were, you know, when you were traveling the country that have almost come back full circle and how you think about decisions you make now?

Yeah, I think one, I'm very comfortable with uncertainty.

Um, I'm gonna say life begins where your comfort zone ends. That feels like your motto in this.

Yeah, I think, um, I think that that's where a lot of people struggle as founders. It's in choosing the path forward. And as a founder, one of your jobs is to find certainty, a direction in infinite paths where there's infinite options. You look at them all and you say this way, right? Even if it doesn't make sense and you have to say that with conviction and bring all these people with you. Um, and so I had to learn how to think for myself when I was traveling and taking care of myself. And I've very much taken that mentality into, you know, company building, product building. Also feeling— and this is a dangerous thing that takes, takes nuance— but feeling confident in going forward where people are telling you this is the wrong path. right? Where the, the norm, how people are doing it today is this one way and your intuition tells you, no, no, I, I think it's this way. I mean, honestly, that's where a lot of opportunity is. If you look at, you know, like the graph of, um, common sense, uh, like everyone believes this thing, um, contrarian, um, uh, so if, if, if you're very contrarian, um, that's often where opportunity is.

So Isha, I think one of the things that stands out the most about you is your routines and your systems and just how you operate as a person. As a friend, I am very envious that you have just like superhuman discipline. And I've honestly gained a lot just from like listening to, you know, what that routine looks like. I've implemented some stuff into my own life and it's, it's really made a difference and I'm curious if you, if you'd be willing to share, like, in detail, how, how did you get yourself to a point where you have this sort of operating system? And then also, what does it look like for everyone listening?

I think the reason that I'm so strict with myself, before, you know, getting into the details, is that I know what life looks like without discipline for me, right? I built a life where I could do whatever I wanted. And that meant I did whatever I wanted. I was drinking at like 7 AM, right? I would, you know, eat the crappiest foods, you know, taking and abusing substances. What were you eating? Man, Taco Bell like crazy, bro. Like they should sponsor me. Like just—

How often?

You should see my DoorDash from like back in the day. It's disgusting.

Really?

It's disgusting.

Once a day, twice a day?

Sometimes a few times a day, or I'd just order like a huge order and just like eat that order for like, like 2 or 3 days. You know, it's like, it's bad. It's bad. Wow.

You said you were doing substances.

What? Just abusing. Yeah. Abusing all types of stuff. Wow. I, yeah, everything. And I think the, for me, being young in Los Angeles, with so many people doing those things around me and still being successful, I didn't have any of the feedback mechanisms that told me that I was abusing these things.

Right.

Because it didn't affect my social life. Because, like, I'm a happy drunk, right? I didn't really make a fool of myself because it didn't affect my work because I didn't have a boss, right? Because Um, you know, yeah, it didn't affect my relationships, um, productivity, etc. Um, I just went deeper and deeper into these bad habits to the point that it really, really affected my health, to the point that, I mean, at some point I was very much on the path to destruction, like death. Um, and so seeing what my life looked like without discipline, I know that I just feel better, I think better. And if I don't set those boundaries, no one in my life will. No one, no one's going to tell me, do these. My employees won't, you know, my friends won't, um, you know, I don't have a family that will.

If you had to strip away a lot of the things that you do and boil it down to one or two things that you think are like most critical for your own, like, well-being and day-to-day, what would those things be?

Um, I'd say one, prayer slash meditation. Um, and so for me, uh, being able to really clear my mind and connect with myself is really, really important because there's just so much noise coming from all these places— social media, um, work, even our own thoughts— just drowning everything out, being this cause of anxiety. And like, you can't even really control those thoughts, they just kind of come at you.

Totally.

But you can choose whether or not to focus on them. So one, the meditation, the other side of that is prayer. Yeah. So connecting to my God, putting up my thoughts, my wishes, and really just expressing gratitude.

When you say my God, like, who are you referring to?

Yeah. You know, the only God above and the creator of all things. Yeah. Yeah. My, my savior.

Were you always religious?

My dad was a pastor. And so I grew up in the church. I went to church like twice a week, you know, growing up. I went to Bible camp, uh, every summer for like 10 years, mission trips, you know, all over. It was very, very strict. And then when he left, I became atheist for a very, very long time. And it wasn't until the last really Yeah, 8 years that I've started revisiting my spirituality and I found it.

Did something happen that got you to do it, or?

Um, it started with, uh, me getting into Buddhism. I had all this unresolved trauma, um, from my youth. I was still very angry, uh, at all these things I just didn't understand in the way that it manifested. Um, just wasn't healthy. And I started looking into why I was so angry. And looking for tools to help me get to the source of all that. Through that, I found Buddhism and I was able to look inside and ask myself, you know, why do I suffer? Getting to the root of my personal suffering and then finding the truth, the enlightenment as to how to escape that suffering through detachment. And then through that path, I started identifying as a Buddhist for a very long time. And I think Like philosophically, I'm still aligned, but spiritually it opened the door to the idea of oneness to me. And I think through the idea of oneness, I opened the door to God and my connection to other beings, and that opened the door to Christianity to me.

You've talked about this idea of the second mountain. What is your first— what was your first mountain and what is your second mountain? Help us understand. What is, what is that?

Yeah, yeah. My first mountain was trying to chase accolades, trying to chase financial success, proving to myself that I was capable, that I was worthy of love and all of these things, trying to prove to others that I was worthy. It was a bottomless black hole that led to unhealthy actions and unhealthy attachments to work, to sex, to relationships. That mountain, it doesn't have a summit. If anything, it just drives you deeper.

Or a treadmill.

Yeah, it's like a hamster wheel or a bottomless pit. And then through my spirituality, my path, my journey through that, as well as my journey through fitness, I started realizing that there's just like more, more to life than just a dollar, chasing money. More so, I think also being in venture capital, like money isn't real. It's just— sorry. My relationship with money—

Why? Just because there's so much of it, you're saying?

There's just— there's so much of it. And Yeah, it's just interesting. Like, my net worth, you know, has changed over time. You know, my, the amount that I have access to at any given point, you know, has changed significantly over time. You know, my personal, you know, like the cash that I can personally use without going to jail, you know, that's changed. Um, but it's just like, it's just agreements. It's just agreements. Like you convince people of things and, um, as long as, you know, and I guess that's what currency is. It's just a ton of agreements. And if you're really good at talking, um, then you're given more. And if people agree that you're worth this much or your company's worth this much, then you'll be worth that much. Um, but throughout all this, like I've been able to survive. And so I just, I just, money's like an illusion. It's just this, this thing in, in the background now that You know, it's generally going up, but I'm still in a one-bedroom apartment.

So the second mountain, if you had to title it, would be what?

Yeah, I think it's, for me, it's very much chasing a life of service. Um, yeah, also, but that service is targeted towards my communities, to the people around me, um, to God. Um, it's trying to just make the world a better place. Make people feel better. Yeah. So they don't chase the same things that I did. They don't feel the same things that I did.

And what role does God play for you now?

Yeah, I think it's just my inspiration. I think everywhere that I go, I just feel so much gratitude for what I see, like the life that I've built, everything around me, whether I'm walking, you know, if I'm hiking, I just, I look at everything. I'm like, this is all so beautiful. Um, and so these days I just, I just have a lot of gratitude for, um, the things around me and then the life that I've built. And so the, the first thing, it's, it's, it's, he's, he's the creator of all things and I just feel so much gratitude to be able to witness and enjoy all this. Um, yeah, two, he's like my source of strength. Um, yeah, I just, as, as my faith has grown, like my faith in God has grown, my faith in myself has just grown. And there's that verse, like, you know, if you have faith the size of a mustard seed, you can tell a mountain to move and it will move. And that's what I've seen in my life, is my faith has grown. The things that have happened around me is unreal. Unreal.

What would you say is the biggest difference in how you operate now as like a Christian in terms of how you build your company versus like how you used to?

I think, you know, before when I started the company, it was like, let me get the bag as quickly as possible. Right? Well, me and my co-founder, I was like, as long as we're good, you know, um, well, obviously I didn't want to do anything that, uh, would hurt my, you know, team or anything that was against my values. I've always had a pretty strong value system. Um, but now it's, now it's different. Um, I, I've realized like a few things. Like one, if I exited today, I might take a few months to have fun, but then I would spend the next few years trying to get back exactly where I am today in terms of, you know, size of company, in terms of like impact that we're having, etc. And so now I'm trying to really align myself with having the most impact. And that's really like my metric of success, like the impact that I'm having and my personal alignment that I have, like morally and such with how I'm living my life. And so I see impact as a number of things. It's not just value that you're capturing, but it's how you're impacting lives. You know, are the employees at my company happy? Are they, you know, safe? Do they feel aligned, you know, with this thing? Am I doing good in the world? Am I taking the resources that I'm being given as like a salary or whatever it may be and going out and doing well?

You have this list of self-affirmations on your phone that you read every morning. I thought that was really interesting. I think people talk about this, but I know very few who actively practice it. Can you share what that list looks like, how it's helped you?

As I mentioned earlier, like, we're constantly bombarded from all directions of people, like, demanding things of you and people telling you what's important, people telling you how the world is and telling you what you are and, like, what you aren't. And so for me, it's really important that I remind myself of what I believe, what I believe about the world, what I believe about myself, and how I want to be in that world. And so my affirmations is my time before I give myself to the world, um, before I let the world tell me, you know, what it is. I tell myself what I believe and who I am. And so it's this long list that I've been working on for several years. And at this point, it takes me like a few minutes to read it. Um, but it essentially represents like my worldview and my relationship with myself. And so I read it and I say, you know, I have everything I want. I live in abundance. I can achieve anything and everything I put my mind to. You know, God is real and he is with me. Everything that I do is for the advancement of humankind. You know, I am strong. I am handsome. You know, I am successful. I am, you know, whatever all these I AMs and also all these I AM NOTs and I do not like, I do not cheat. I do not steal. I do not lie. I do not hate. Anger is beneath me. All of these things that are just reminders of who I am.

And you've noticed it's made a difference?

Yeah. Yeah. I think it's also, it's visible in a few different ways to me. Like one, how I think and talk about myself. You know, like I can say very confidently, I am an excellent human being because I tell myself that every day. And if there's a time during the day where I have the opportunity to do or, you know, say or maybe even like think something that isn't aligned with what I've told myself, I chastise myself immediately. Like in my head, I'm like, this is not who I told myself I am. And I don't do that thing. And so it helps me remind myself not just in the morning, but throughout the day of how I am. And it does, you know, slowly have very much become how I interact. Two, as I've given myself more grace, as I've developed more love for myself, I have so much more love and grace for other people. We're typically hard on ourselves, or we're typically hard on other people when we're hard on ourselves. And so I think it's really helped me show up better in my relationships.

Is you, you know, your story is just one where you got to ask him. I have to ask this question, which is like, do you— what's your view on luck? Like, Is it real? How does it work?

Yeah.

Like, do you make it? What's, what's, what's your view on luck?

It's always really annoyed me when I hear people say, you just got lucky, right?

You specifically, or just when people say that in general?

When you— definitely me.

Yeah.

But, you know, in general, for sure. Um, because, like, luck isn't just, um, you know, just, just random happenings. I think like you can create your luck. And so there's, there's this like saying by Naval or this, this conversation that he has, Naval being this prolific investor. And he says there's 4 types of luck. And oftentimes, usually people put everything into the first type of luck, which is like pure chance. Like if you win the lottery, that's probably pure chance. Or maybe it's fate, but you can probably attribute that to pure chance. Then there's luck that you create by kicking up dust. Um, and so if you, um, there's, there's this, uh, this woman that I really admire. Her name is Nancy Liu. Um, she's the CEO of a company, Unplug. Um, she would talk about how, uh, when she was getting started, she would go out to all of these networking events and she'd hand out 20 business cards. She'd get 20 business cards and she'd email everyone the next day. And throughout that, she met tons of investors and many of them invested into her first company. And so, you know, people could say, oh, well, she got lucky, you know, because she met those investors. Well, she put in the effort, like she created that luck by kicking up dust, by putting herself out there. Then there's, you know, luck that happens because you investing like in a skill. And for example, if you are the best scuba diver in the world, if someone comes to you and they say, hey, you know, you're the number one scuba diver, you know, you've built a really great reputation. I have this treasure chest at the bottom of the ocean. If you go get it, I'll give you half of it. Which sounds crazy, but that's like what CTOs are, right? You know, people come to you. For a long time, people were pitching me ideas like 5 to 10 times a week because I built a reputation for myself as, you know, a really great CTO that built all these products. Then, you know, there's, you know, luck that just comes from like, you know, like your character and like, you know, who you are. So when you have really high integrity and like values and people are like, man, like you got to know this person. And that's not just because of like your skill. It's not because you're like work really hard. It's, it's because of like your integrity and like your morals. Like this is someone that you should know. Um, and for my agency, like 90-something percent of my business was inbound, is from referrals. Um, and so I would say that multiple times a week someone is in a room that I'm not in and they're like, man, Ishmael should be here. Right. And then they would tell this person, you have to meet Ishmael. And, uh, they'd give my contact or, you know, put us in a chat and that would lead to, you know, a deal. Um, and so I'd build their app or at a certain point towards the end of the agency, I had too many of those coming in, um, that I started selling those referrals and I made like really good income just, you know, uh, selling referrals. But those, those are 4 types of luck.

And ish, I would ask you, like, if people listen to this whole podcast and they have to take away one thing, if you had, if they, if they, if they forget everything, but they remember one thing, what would you want them to remember?

Um, the first thing that came was, was God. Naturally, that's where my, uh, brain turns.

What about God specifically?

I think for me, um, looking back at everything that's happened to me, um, there are so many times that I could have been killed. I could have lost everything. Things couldn't have, wouldn't have worked out for me. And it's not just like one, it's not just like 10, it's like hundreds at least, at least, if not, you know, thousands. And so when I, when I just like look at all of that, I can't credit my success to my merit. Sure, like I worked for it. I, you know, I put in time, I took the steps forward. You know, I took that first step out with that heavy backpack and that guitar. Yeah, sure, I went to those events. You know, I bought that computer and taught myself how to code. But it wouldn't have mattered if I died any one of those times.

You had to have— be supported by something to keep you able to go do those things.

Something greater. Something greater. And so looking at that, like, I believe, like, you have to have, like, a really, really strong why and also just, like, recognize that. For me, you know, I credit everything that I've ever accomplished and will ever accomplish to my creator. I would not be here, you know, without him. And because of him, it's also just like impacted the grace and the things that I do in the world. And so, you know, if I could share one message, it's, you know, find God, connect to him, and that will and change your outlook and give you gratitude, give you a source of strength. There's nothing like the power of faith to power you through anything that you're going through. If there is one message, that's the one. Yeah, I give probably some founder advice of like, oh, well, you know, if you're in this situation, do this.

But we said pick one.

Yeah, but you know, if there's one, it's find God.

Ish, thank you so much for being on the pod. This is really fun. Your story is incredible. I can't wait for people to see this.

Yeah, thank you for having me, guys. Appreciate you. Yeah.