He Built a Simple App and Sold It for $200 Million⏐Ep. #242

Summary

The Koerner Office: He Built a Simple App and Sold It for $200 Million | Ep. #242

Date: November 3, 2025
Host: Chris Koerner
Guest: Dan Porter, CEO & Co-founder of Overtime

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Episode Overview

In this episode, Chris Koerner sits down with serial entrepreneur Dan Porter, the creator of Draw Something, which sold for $200 million. Porter discusses his eclectic career journey, core principles behind building hit products, and the pivotal role of creativity, risk-taking, and relentless focus. The conversation is full of candid, practical entrepreneurship wisdom, deep dives into the creation and meteoric rise of Draw Something, perspectives on the evolving creator economy and AI, and unique takes on business idea validation.

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Key Discussion Points & Insights

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Dan Porter's Unconventional Career Path

• Background: From high school teacher to music business, gaming, and now sports media as CEO of Overtime.
  • “Everything that I do is almost like a combination of all those different experiences. It’s really not a straight path.” (01:05)
• What Differentiates Dan:
  • Relentless focus and not giving up, playing only games he can win.
  • “Maybe I’m an out of the box or disruptive thinker…Maybe I don’t understand the way things are supposed to be done, so I come up with my own ideas.” (01:40)

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The Value of Creativity & Diverse Experience

• Creative Problem Solving:
  “Some people…play the guitar with both their hands…they create entirely new music. Maybe they just never learned the other way or that felt natural to them.” (02:17)
• Education & Out-of-the-Box Thinking:
  – Laments that the education system does little to encourage creative risk-taking, which he sees as essential for innovation. (03:10)
• Interviewing for Depth:
  – When hiring for his gaming company, he valued candidates who displayed deeper thinking:
  “Those people really think deeply about games and game design. And those were the people that I hired.” (05:14)

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Breaking into and Succeeding in Gaming

• Entering Gaming:
  – Inspired by the cultural relevance of gaming and seeing firsthand its dominance among youth.
  – Took an 80% pay cut, quitting a job at Virgin to run a fledgling gaming startup.
  – “I was like, there’s so much I don’t understand about this. Like, I want to figure it out. And I’m like—this is hard.” (07:34)
• Product-Market Fit Discoveries:
  – Realized the actual players of their games were 14-year-old girls in California, not the cool NYC adults they expected.
  – Adjusted branding and product to better serve this customer base.

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The Draw Something Phenomenon

The Messy Middle & Finding Breakout Success

• Early Struggles:
  – Company at crossroads after missing tech shifts (e.g., Facebook-platform games, Angry Birds). – “It’s kind of like the messy middle…Not like you have no users, but it’s not like you have a zillion users.” (10:34)
• Iteration and Breakthrough:
  – After initial failure, a technical fix sparked viral growth:
  “Shot to number one and stayed there every single day for six months. 25 million people a day were playing it. It’s the number one game in 60 countries in the world.” (00:09, 11:19) – Sold for $200 million to Zynga. (00:23, 23:05)

Why It Worked: Simplicity and Social Mechanics

• Design for Simplicity:
  – “I’m not a game designer, so I made something that was so easy to understand and play…very collaborative…not based on winners or losers…more social.” (14:01)
• Crucial Product Tweaks:
  – Only allowing play among friends (to combat toxic behavior common in open internet spaces). – Streaks—borrowed from a real-life observation with his son—transformed the mechanic:
  “A streak is a way that two people can play a game and be on the same team and not be competitive.” (20:43) – Playback feature by teammate Will Chen brought games to life:
  “If I drew a picture … you watched me draw it. It felt live.” (21:24)

The Power of Small Tweaks

• Multiple Ingredients Needed:
  – “If you miss one of those…You take the yeast away, now you have flatbread and it sucks. You take one of those four key ingredients away, then it’s a nothing burger.” (23:07) – “Sometimes you’re one tweak away from $200 million.” (00:04, 24:47)

Outsider Advantage

• Benefiting from Lack of Preconceptions:
  – “Sometimes you have people who are from outside of an industry who are good at making something.” (18:21)

Experimentation and Execution

• On Research vs. Doing:
  – “The building of the thing is the best research you can do. Building is the research.” (19:34) – Learning comes through trying, not just planning.

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Post-Draw Something: The Creator Economy & Overtime

WME & Digital Creator Boom

• Building Digital Talent Management:
  – Signed 250 YouTubers, laid foundation for the creator economy:
  “Everything that we think about creators now was doing 2013-2016…” (26:09)

Overtime: Reinventing Sports Media

• Genesis:
  – Founded Overtime after noticing young people weren’t watching live sports, despite loving online creators.
  – Did not rely on user-generated content; instead, created a paid network of 800 iPhone ‘filmers’ with proprietary software.
  – “Today, every week, a quarter of a billion people watch a video that we make. We have over 110 million followers.” (30:34)
• Finding Talent:
  – Frequently hires filmers as full-time employees.

Trends & Business Opportunities

• Future Areas Porter is Bullish On:
  – TikTok Shop and creator-driven product commerce. – NCAA Name, Image, Likeness (NIL) and the transformation of college athlete branding.

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Building and Launching 67 Water

• Viral Launch:
  – Created a water brand based on a meme; tens of thousands sold, 41,000-strong waitlist. – Leverages field customer development rather than traditional research:
  “It starts as this kind of instinct…But now a lot of the decisions are being made because people on the street are spending time … and seeing what they’re buying and asking them why." (34:10)
• On the Meme’s Inclusivity:
  – "Everyone can say it and everyone is in on the joke…there's actually not a lot of things that are really inclusionary, like on a broad level” (36:11)

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Teaching, Mentoring, and Student Wisdom

• Spotting Potential:
  – “People ask good questions…they think differently, rate at a different level. Like, they’re confident about the knowledge, they’re engaged, they’re not asking if it’s going to be on the test.” (38:44)
• Misconceptions Among Students:
  – “Whatever you major in does not matter. Your grades do not matter. And whatever your parents tell you, you should probably not listen to them because it’s your life.” (45:18) – “You can either live somebody else’s story or you can write your own story. And it’s way scarier to write your own story…” (46:22)
• Creativity in Childhood:
  – “Five year olds are crazy creative … and it just kind of all goes like this…if you can break out of that, there’s so much crazy potential in the world.” (46:33)

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Entrepreneurship Philosophy: Focus, Passion, and Obsession

• On Focus and Obsession:
  – Goes deep on any problem, even home internet wiring:
  “I’m not giving up. Like I just will not give up.” (41:11)
• On Chasing vs. Focusing:
  – “When people are like, Oh, I own four businesses … I don’t know how they can be great, because for me, I just gotta be obsessed and all in…” (43:16)
• Culture as Entrepreneurial Inspiration:
  – Sees business lessons in pop culture and broader trends—not just tactics.

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Reflections on Passion and Profit

• Nuanced Take:
  – “You can have passion for things that you do. Accounting, marketing, talking to people, sales, live events. As you get out in the world, you’re just like…what drives that passion? A lot of times you’re good at it…separating that idea that the passion has to be your interest versus the thing you might actually be really good at…” (47:16)

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Notable Quotes & Memorable Moments

• On Entrepreneurship:
  • “You can either live somebody else’s story or you can write your own story.” (00:00, 46:22)
  • “Sometimes you’re one tweak away from $200 million.” (00:04, 24:47)
• On Product Creation:
  • “If you take one of those four key ingredients away, then it’s a nothing burger.” (23:07)
  • “Building is the research.” (19:34)
• On Navigating the Messy Middle:
  • “So you’re somewhere in the middle. Like, it’s not like you have no users, but it’s not like you have a zillion users.” (10:34)
• On Student Potential:
  • “Some people ask bad questions and other people ask really, really good questions. And people ask good questions, you get it. They’re just people who…think differently.” (38:44)
• On Culture:
  • “Great products feel great even around the edges…all of those little things make a difference, but they all have to come together.” (23:49)

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Key Timestamps

• 00:00 – “Live someone else’s story or write your own story.” (episode’s thematic bookend)
• 08:07 – Realizing their true customer base
• 11:19 – Draw Something’s viral breakthrough
• 20:43 – Discovering the “streak” mechanic’s inspiration
• 23:05 – Discussing the $200 million sale
• 24:47 – The importance of little tweaks in product and marketing
• 30:34 – Overtime’s business model and scale
• 34:10 – Building 67 Water and how customer feedback drives iterations
• 41:11 – The value of obsessive focus for entrepreneurs
• 45:18 – Student misconceptions (“major doesn’t matter; grades don’t matter”)
• 47:16 – Passion vs. profit discussion

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Final Thoughts

This episode is a treasure trove for anyone interested in entrepreneurship, creativity, or product-market fit. Dan Porter offers unvarnished stories and actionable wisdom on how serendipity, scrappy iteration, and relentless focus can converge to produce outsized startup outcomes. The discussion is also a testament to the enduring importance of creative thinking, self-directed learning, and the courage to write your own story.

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Dan Porter on Social: Find him at @tfadp on Twitter and all platforms.
Chris Koerner: For more, visit TKOPOD.COM

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Transcript

[A]

You can either live somebody else's story or you can write your own story.

[B]

Sometimes you're one tweak away from $200 million, right?

[A]

Yeah. If they don't say that, the app doesn't blow up and the company goes out of business. It shot to number one and stayed there every single day for six months. 25 million people a day were playing it. It's the number one game in 60 countries in the world.

[B]

And what did you end up selling it for?

[A]

$200 million. I mean, I was a high school teacher. It is all of those little things that make a difference, but they all have there.

[B]

Okay, well, why don't you start by just telling us who you are and what you do, Dan.

[A]

My name is Dan Porter. I was on an episode of the career ladder on TikTok, and I am the CEO and co founder of Overtime, which is a big sports platform that we started in 2016.

[B]

Okay, and what would you say makes you different from your peers, your contemporaries?

[A]

There are a lot of answers to that. I'd say, number one, the nature of my career. Like, I've. I've been a public school teacher. I worked in the music business. I run a gaming company. I'm in sports. I've just done a lot of different things. And so everything that I do is almost like a combination of all those different experiences. It's really not a straight path. It's probably, number one, I'd say, number two, I'm very relentless and focused and I don't give up. I don't play a lot of games, but I try to only play games that I can win. And I think number three is that you could say that maybe I'm an out of the box or disruptive thinker. And I'm not trying to compliment myself in that, but more just like, I don't know the way that I think of things. Maybe I don't understand the way things are supposed to be done. So I come up with my own ideas, but I tend to approach problems probably a different way than other people do. So probably those three things, plus occasionally I'm very funny.

[B]

Do you think you approach problems differently because of your breadth of expertise? Are they correlated?

[A]

It's a good question. I'd say half of it is that I just have so many different experiences I draw from, and half of it is probably like, I'm just really stupid and I don't know the right way to do it, so I just come up with my own way to do it. Sometimes, like, you see people who, like, play some musical instrument in a really weird way. They play, like the guitar with both their hands or something like that, and they create entirely new music. And maybe they just never learned the other way or that felt natural to them. But I think in general, I don't know if through school and college we do enough collectively to promote kind of creative and different thinking. I think we tend to optimize towards people who think alike. That's why we have tests in school. Tests are like, tell me what the right answer is. That's the right answer. Everyone is like, they're like going right towards the tip of a triangle. I love music. I was a musician. I focused on improvisation. I took a lot of creative writing. I think just taking inspiration from writing and music and arts and all the different way that people have thought about, you know, recreating all kinds of music and even writing and stuff like that is probably part of it. But I don't think we do ourselves any favors as a system in this country and promoting people who are either think creatively or out of the box. And I think most people in college, I took painting, I took photography, I took poetry, of which I was truly terrible at. And luckily, none of those poems survived. And I took either two or three semesters of creative writing. And I just think learning those things, if I ask kids today, they take computer science and economics and there's nothing wrong with those. That's what I think.

[B]

Yeah, well, creativity, it's more important than it's ever been, and it's more rare than it's ever been.

[A]

It's a differentiator. I think about, like, you know, when people apply for jobs, sometimes you interview for a job. You interview people. Maybe you're interviewing a salesperson. And it's like everybody worked at a similar company. They all have the same title. They've all sold a number of big deals. How are you going to differentiate, like, 10 people who come in and have an interview with you or zoom in an interview with. And I think there's some element where, like, a lot of times I'll ask questions. When I was in the gaming business, when I ran OMG Pop and I used to hire game designers and builders, software developers, I really used to only ask one question. And the question I asked is, like, what is your favorite game? You tell me. Final Fantasy or whatever. And then I would say, why is that a great game? And people would say, it's fun or whatever. And, you know, one out of every five people would say something like, oh, the way that like, this mechanic works, and they describe some intricate part of the game. And you just think, oh, those people really think deeply about games and game design. And those were the people that I hired, someone that.

[B]

That looks at it differently than everyone else.

[A]

You're able to understand why things are the way they are.

[B]

Yeah.

[A]

And is. Is a thinker, and some of that is creativity, and some of that is thinking. But I feel like those people, they can have an impact on you and your company, but you can appeal to them to try to make something bigger and better versus people who do less. So. And I think that even though some of that is natural, we can all always be better at learning how to do that.

[B]

Yeah. How did you get into the gaming business?

[A]

I was working for Richard Branson. He was a very successful and famous entrepreneur. And part of my job was kind of helping him make the Virgin brand relevant to a whole new kind of generation. And I just thought, let's go to the roots and do music. So we did music festivals and other stuff like that. And I kept reading at that time maybe 20 years ago, like, the gaming business is bigger than the movie business. It's bigger than the music business. And in fact, funny enough, I have two sons, and I took them to an outdoor concert that I put on, and they spent the whole time playing the Nintendo DS backstage. And I just kind of was like, wow, Gaming is kind of relevant to culture in a way that music probably was in the 80s and 90s. Not that music isn't, but gaming is. So. It's so widely played, and it's so pervasive. I don't know, 90% of kids play play Roblox or anything else like that. I just kept thinking about it. One day this investor said to me, oh, I know this guy. He's starting a gaming company. Could use some help. So I met with him, and I honestly didn't understand anything that he said to me. I didn't understand his website. It literally made no sense to me whatsoever. And so I quit my job and took an 80% pay cut and became the CEO of the gaming company.

[B]

That's a big leap.

[A]

Yeah.

[B]

You just thought. You just thought, this is a tidal wave that I want to be riding, so it's worth taking this big pay cut to ride it.

[A]

Yeah. And also I was like, there's so much I don't understand about this. Like, I want to figure it out. And I'm like. I was like, this is hard. They know a lot about something I don't know a lot about. I Clearly get where gaming is going. And it was, it was before we had digital goods and everything else. But he understood that stuff was going to come from China and from other places in terms of a business model and come here. So I just jumped and took a risk.

[B]

And what happened after that point? How did you get from that point to draw something?

[A]

He was a really cool guy and everybody worked at a company, was super cool and lived in New York and Williamsburg and like went to coffee shops and like made like really cool games for people like them. And it was a really multiplayer game site. It was one of the first chances that people could really play online with each other as opposed to by themselves. There was no iPhone or anything else like that. And I said, who are the users? Who are the customers? And they said, people like us because that's what we make games for. Got deep into Google Analytics and so forth. And I realized that the customers were actually almost entirely 14 year old girls in California.

[B]

They were just assumed.

[A]

Yeah.

[B]

And they were wrong.

[A]

That's who was playing the games for five hours a day. And I was like, well, maybe that's our customer. And then the name of the company was I'm in like with you, which is really funny.

[B]

And that matches with a 14 year old girl.

[A]

I mean, well, I realized that when people typed it into Google they misspelled it and we were losing traffic. So we changed the name, we understood who the audience was and we started to grow and we added more and more games and built just kind of like a gaming site where people came and played with each other. And the guy who started was enormously creative and just, just visually talented. Like everything about the games were really great. I remember once we did a talk at a conference and he got up and he just said, my goal is to make a game that's so good that some kid mows lawns to make money to pay for it. It was good. And then we were successful with millions of users. Average time on site was four and a half to five hours. And then farmville came out and farmville was built on top of Facebook. All of a sudden they had 100 million users. We had like 3 million users. All of a sudden we were big and then we were small and the whole world was playing FarmVille and other Facebook games and the iPhone had just come out. And I was like, wow, we missed Facebook. We didn't make Angry Birds. Sometimes you wonder if it's too late. Sometimes it is, but sometimes you feel like it's too late, but it's Not. We started to make some iPhone games and then it's like there's a hard part where you don't fail, but you don't succeed. So you're somewhere in the middle. Like, it's not like you have no users, but it's not like you have a zillion users.

[B]

It's kind of like the messy middle. Like, yeah, you're not uber Valley of.

[A]

Death or something like that.

[B]

Or worse. Yeah.

[A]

Long story short, we had a drawing and guessing game that we had tried to make for Facebook and we had made for our site and I decided to try to be the game designer and work with a couple people in the company. And we just made it as an iPhone game and we released it and it did okay. And then it kind of bombed. And then some of our developers were like, I think there's a lot of people trying to play it. I think there's a technical problem. And they worked all weekend, they fixed it and it shot to number one. And it stayed there every single day for six months. 25 million people a day were playing it. So the number one game in 60 countries. Countries in the world and a quarter of a billion people downloaded it. Oh, okay.

[B]

All right. I want to get to that before we get there. I find it so interesting that, you know, Facebook releases games and you suddenly feel like a very small company and you are compared to farmville. It made me think, like a lot of times we talk about platform risk, like platform risk to watch out for those platforms. You know, don't want to be relying on one platform. But that same platform risk can put like non platform businesses out of business because that platform is so big and strong and scary.

[A]

Right.

[B]

It's the other side of the argument.

[A]

You know, I'm trying to reach young people. So I built this website and I was like, who goes to a website? Like you think they're going to your website? Like, have you ever seen a young person open a browser on their phone?

[B]

They don't go to a website only to do homework. Yeah, exactly. Why didn't draw something for as a Facebook game work, do you think?

[A]

I know exactly why it didn't work. It's kind of not working. Inspired the thing that made it work. So basically on Facebook it's like Pictionary. It's like a drawing guessing game. So it's open, you go into a lobby and there's three other people there and all of a sudden the word comes up and you draw it and people guess. Well, if you put people in a lobby with three strangers, they're either going to draw anatomical body parts or they're just going to be rude. And what could be really fun was basically kind of toxic most of the time. Not all the time, but most of the time. And so when we made it for the phone, we only let you play your friends because we were like, we can't stop people from drawing funny things or being annoying phallic things. Yeah. But if you know that they're with their friends, their friends are either going to say knock it off or they're going to think it's funny. And so I think what didn't work is kind of like a wide open space worked amazing on a friendly basis.

[B]

It's almost like a version of niching down, like preventing other people from playing it. Kind of like Facebook in the early days. Right. Like you have to be a Harvard student.

[A]

It's like you couldn't solve changing people's bad behavior on the Internet. So it wasn't like you could then penalize people and they could report them and everything else like that, but you could solve just not having it open to everyone on the Internet. So it was easier to solve that than it was to solve the former.

[B]

Yeah. And then you, you have a built in virality because you can invite all your friends in your contact list, right?

[A]

Yeah. I remember somebody told me I'm getting invites for draw something on like people that I was on instant messenger with that I haven't even talked to in five years.

[B]

Yeah. What. Aside from like the built in virality of it from a base principle perspective, why do you think it resonated so well?

[A]

I think it was really simple. I'm not a game designer, so I made something that was so easy to understand and play. Number one. I think it was very collaborative. It was funny. It was the first thing to use your finger on the phone. It was tactile, was what the phone was meant to do, not be a joystick replacement. We didn't make it based on winners or losers. You tried to have a streak with the person that you were playing with that made people feel like they weren't competing with each other. But it just was like a little more social. It was actually, in a weird way, it was just very. It was social at a time when most games were not social.

[B]

Yeah. Do you think at the time there was less competition for people's attention on.

[A]

The phone at that time? I would say that maybe seven of the top ten apps were games. I'd say now zero are. They're mostly either Uber or Instagram or TikTok.

[B]

Short form video.

[A]

Yeah, short form video. So that was a moment, probably from 2010 to 2015, when games just dominated the phone. That's what you did. And then I think social media really knocked that out. And game discovery was like, people would be like, what are the new games? All the time? And there's not a lot of games. There's not a lot of mobile games that, like, since then, like, people still play. They might play that. They play Words with Friends or Candy Crush or whatever. But in the last five years, I'm not sure there's been a mobile game that I can think of that's just, like, taken over. And everybody's done it because most of their attention is on social endeavors.

[B]

I'm just continually amazed at how innovative and addicting short form video is. Not just the medium, but the algorithms that drive it, and just how accurate it is at showing me what I want to watch.

[A]

It's scary. Yeah. I mean, you know, technology is good and it knows you. I uploaded 50 essays that I had written into ChatGPT and I said, I want you to reverse engineer my writing style and then I'm going to give you a prompt and I want you to write it like I write it. And I'd say It was like 90% of it literally sounded like I wrote it.

[B]

Oh, man. In your story, I think you glossed over something quickly. And let me make sure I get this right.

[A]

You.

[B]

You were running the company initially, right?

[A]

Yeah. I was a CEO.

[B]

You were not a developer by any means.

[A]

I'm not a software developer.

[B]

And you had this idea, and for some reason you said, I want to build this one. Is that because you. You just wanted to learn how to build games or you were so passionate about it, like, you just wanted to own it?

[A]

In the movie version, it's because I'm so passionate. But in reality, I just think, like, we were starting to be like, we didn't make Angry Birds and we didn't make farmville. Like, are we effed? Like, what's going to happen to us? I was like, maybe we're going to fail. Like, if we're going to fail, at least maybe I could try to make a game.

[B]

Yeah. So it wasn't like, this is the best idea I've ever had. This is going to save the company. Let me go on the front lines and do it.

[A]

It's more like 90% of the company was working on other games.

[B]

Yeah. So you're like, all right, we're kind of in flight mode. We're in survival mode right now. I have this idea and you weren't thinking, like, this is genius. This is for sure going to work. I'm fully confident. But it was kind of like, I think there's something to it. But I don't want to distract my team. They're just trying to keep their head above water. So why don't I try to build it?

[A]

I had no idea if it would work. Also just was like, I don't know. I just want to try to make a game. I do overthink some things. In this case, I didn't really overthink that. I just was like, I think I can make something that. It's funny because the company that bought us was called Zynga and they were the makers of Farmville. Ironically, I went to the offices in San Francisco when we were in the process of contemplating an acquisition and they had all this stuff on the wall and all these game designers were reverse engineering the game and trying to figure it out why was it successful. And I went over and looked and they were like, oh, you made the game. And he's like, I just have this question for you. Like, why didn't you use XP in the game? Experience points? At that moment I thought I forgot I didn't use it. But it just like totally slipped my mind. And now whatever.

[B]

Like that.

[A]

It's like. And they just couldn't believe that that was the case. That was the honest answer. So it's like, I don't know. Sometimes things just work themselves out or it's good enough as is. And sometimes you have people who are from outside of an industry who are good at making something. I had, I met up with a friend of mine, had been the Internet business, and then he was in the fashion business outside of the United States and he came back to the United States and he's like. I said, oh, what are you up to? He's like, let's catch up. He said, I'm making like a sparkling water. Like a SodaStream competitor. I was like, you worked in Internet and fashion. What do you know about sparkling water? Like, and he goes, I don't know anything about it, but I'm an entrepreneur. That's what I do. I learn about stuff.

[B]

Yeah.

[A]

Whoa. It's pretty powerful.

[B]

Outsiders are powerful. Like, you could have gotten hung up on adding XP and that could have like held up the whole project. And then you move on to something else and maybe it never happens. Or maybe you added less fun. It could have made it Less fun could have changed the whole dynamic of the game, the whole culture of the game.

[A]

80 year olds played my game. It was so simple.

[B]

Yeah, I say this all the time, but people get so hung up on researching and doing market research and talking to people and what features do I add when, like, the building of the thing is the best research you can do. Building is the research.

[A]

Right. I think that everything is like, it's like an idea. Like, I'm going to make a brand new toothbrush. I have an idea, but it's just a premise and it's just an excuse to get started. Sometimes your assumptions are wrong or sometimes you discover something else, but you need something to get started. You need an idea and a premise. People like, I'm pivoting. I'm like, pivoting is like, you know, when you start out in the Internet business and all of a sudden you're in the underwear business, like, that's a pivot. But like, everything else is just, you're testing, you're learning, you're getting visibility into what's happening. People are giving you feedback on your idea and telling you what works and doesn't work, or you're observing that and, you know, you're building it going forward. And I don't think that's a pivot. I just think you need that first premise and you just need to pay attention.

[B]

Yeah. What first gave you the idea for Draw Something? What was that moment?

[A]

It was the third iteration of the game that we had made for ourselves and for Facebook. So I had thought a lot about why it didn't work. And then the inspiration really was I went to park with my son and his friend, and they were playing catch, and I was like, if you guys can catch the ball back and forth 50 times, I'll buy you an ice cream. And then I was like, oh, it's like a streak. And then I was like, oh, a streak is a way that two people can play a game and be on the same team and not be competitive. And that was like part of the core insight.

[B]

So the triggering event for the idea was the feature of the idea. And then you built the actual core idea on top of the feature.

[A]

It was fixing something that other people had built and designed, but I had thought a lot about, and it was that. And then there was one thing that I didn't have anything to do with, but one of the developers, Will Chen, did, which was he figured out how to play back the drawing. So if I drew a picture of a house and I sent it to you to guess. You watched me draw it. It felt live. You could see me erase money versus me. Just sending you a picture of something. And that aspect of it, which I didn't create at all, it just made it feel so alive and so different. And I think that a great game, a great car, a great product, a great jacket, whatever it is that you experience, like, it has to make you has to feel amazing. Like, I own one suit that I've owned for 12 years. Somehow I still fit into it. And when I put it on, I'm like, this suit makes me feel amazing. Yeah, I look good. I feel like it's great suit. The cut so works. I have a car with a really nice steering wheel. It makes me feel amazing. And that aspect of the game just made it feel great.

[B]

First question, how successful do you think draw something becomes if you never incorporate that feature of, like, seeing it drawn live? Do you think that was a core part of it?

[A]

A hundred percent. I think it does not become as successful without that.

[B]

Yeah.

[A]

All those things, streaks, lack of competition, solving the toxic part, and that everything came together to make it work.

[B]

And what did you end up selling it for?

[A]

$200 million.

[B]

And I feel like if you don't have all of those ingredients right, it's not like, take away the streaks, we sell it for 160. Take away the live feature, we sell it for 120. It's kind of like if you miss one of those. Yeah. If you take one of them away, it's kind of like your bacon bread. You take the yeast away, you're like, it'll just be a little smaller because there's only 1% of this is yeast. It's like, no, now you have flatbread and it sucks. You take one of those four key ingredients away, then it's a nothing burger. You never get off the ground.

[A]

Right.

[B]

I agree on the pessimistic way of looking at that is like, well, that's kind of depressing. I have to, like, put all these ingredients together, and I don't know what will work. And I look at that, it's like, that's freaking amazing. You're a chemist in a lab.

[A]

It were that easy to make a great product, Everybody would make a great product. But you've got to assemble all those things. It's like you asked me about myself and my career. I assembled all of those different things from my different experiences. I mean, I was a high school teacher. Every single thing, you put something together. Like, great products feel great even around the edges. Like when you buy a shirt or you buy like a really beautiful shirt, you'll notice the stitching on the beautiful shirt and everything else like that. Like, it is all of those little things that make a difference, but they all have to come together.

[B]

I mean, you said too, like, your developers are like, dan, I think people are trying to play this, but something's broken, right? What if that conversation never happens? Like, the. The optimistic way that I look at your story is that all these little tweaks make such a difference. And sometimes you're one tweak away from $200 million, right? Yeah, one tweak away.

[A]

Let's say that the app doesn't blow up and the company goes out of business.

[B]

I feel like it's never been that critical. Little tweaks and changes since before the age of the Internet. Like, if I'm running a Facebook ad campaign with a big budget and I check a box that says optimize for conversions, optimized for add to cart, that could be the difference between me spending $10 to acquire a customer and $100. That could be all the difference. So in this Internet connected age, these little tweaks are everything. And so we don't want to over optimize everything and tweak everything to death, but we want to just keep testing everything, right? Yeah.

[A]

It's kind of like yoga, or if you work out, like, most of us end up doing it wrong. So you're doing some pose, and then the instructor comes over and they say, actually your hips have to be forward. And you're like, oh, I was just wasting two weeks thinking I was stretching when I wasn't really doing anything.

[B]

Yeah, yeah. So you sell for 200 million. What do you do after that? What's next?

[A]

So I work for the company that bought my company for a year because that's how those things go. And then I end up meeting Sky R. Emanuel, who's the founder of Endeavor, William Morris Endeavor, famous talent agent. And long story short, he pitches me and I say no, and he keeps pitching me, and I end up joining wme, as it's called, which is the biggest talent agency in the world, is their head of digital. And I build the foundation of the modern creator economy by signing, building, signing 20 agents and 250 YouTubers. And, you know, everything that we think about creators now was doing 2013-2016, and a lot of people who I worked with, who worked for me, all those are now run digital for companies all.

[B]

Over the U.S. what's an accessible version of that business today, if you were to keep all your skills, you're 20 years old and you want to make money in that way, kind of in that industry, how would you go about it?

[A]

Like, I would try to be a creator in a niche that I could own. So either you're broadly popular, or there's creators whose specialty is talking about how to be successful on YouTube. There's finance, there's cooking, there's health, there's exercise. I mean, they're all crowded, but there's always room for people who are creative and, and a lot of people under the age of 30 rely on other people to help them filter information. So if I'm walking down the street and I see some restaurant or coffee shop and there's a massive line, pretty much 100% of the time someone's like, oh yeah, that just blew up on TikTok. This one person went there and talked about it. Now everyone's gone there. So I, I would think about that. I mean, listen, what do they say? 40 of Gen Z wants to be a YouTuber. So it's just a different form of being an entrepreneur.

[B]

How do you think AI plays into that with AI generated content? Do you think that makes like unique creators even more valuable because they stand out even more or less valuable?

[A]

I don't have a perfect answer for that because a lot of what we see now is probably only the tip of the sword. I do think that humans are able to make connections about what resonates with people and what's different and what's distinctly human better than AI. But I think AI can accelerate their ability to create it. I think, like I'll teach a book in my class. Let's say I picked a book, I've assigned it, and now we talk about it and whatever the reality is, I could also just go to ChatGPT and say, Hey, I just read this book. What do you think it's about? It does this ask me some questions? I could talk to over two hours and have a really in depth conversation about the book. But does anyone want to go and just talk to ChatGPT to learn books all day, or do they want to go to class with a professor and other students and feel different way and read body language and everything else like that. So I think there's a role for both.

[B]

Yeah. And as you're reading that book, you're thinking, oh, this character reminds me of my mother. Or in chatgpt doesn't know that your students, they want to know from you without even knowing it. They Want to know from you, like how that book ties into your life experience.

[A]

Right.

[B]

And you're able to deliver a unique experience there, whereas anyone could just regurgitate the chat. GPT summary. Just like spark notes, Right.

[A]

Yeah, it's. I'm going to be more likely to have an opinion which they might agree or disagree. I'm more likely to say, hey, in my life, when I made this game or I signed this YouTuber, I was reading this book and it made me think about X, Y and Z. So I think we are trained to think in this world that B is going to replace A and C is going to replace B. But I think there are ways that it is additive in a lot of different ways. So I think that human creativity is still going to be important. I think there's a lot of AI creativity. I mean, sometimes we'll be working on a project at work and we're like, we just don't have a good name for this competition we're doing. And sometimes the names that come out through AI are amazing and everyone's like, that's perfect. And sometimes they suck. But it's just like, it's a tool. But I don't think we're all gonna just be sitting at home.

[B]

Yeah.

[A]

Because AI is making amazing YouTube videos and other content. But I think it's, you know, it's gonna, it's gonna work together.

[B]

Tell me about the genesis of Overtime and what overtime is.

[A]

Overtime is a sports platform sports brand for next generation of sports fans. I was working in sports at my job at the talent agency and I heard from a lot of sports leagues that young people weren't watching live sports. And I'm like, they're all watching all the YouTubers that I work with, but they're not watching live sports. I wonder if there's an opportunity. So again, I just quit my job and I was like, if we can start a company to figure out how to get every young person to care about us. Oh, by the way, we have no highlights, no live rights, we can't cover any pro sports. But still, we're going to figure it out. And that's ultimately what we did. So today, every week, a quarter of a billion people watch a video that we make. We have over 110 million followers. We have a basketball league that kicks off on Halloween this Friday, the 31st. We have a football league, we have a girls basketball league. We're in a bunch of different league and event businesses, media businesses, and we've created a really dominant brand and maybe the Largest kind of creator in sports.

[B]

Tell me about the crowdsourcing side of that. How do the, how does a kid with an iPhone play into your business model?

[A]

Yeah, honestly it doesn't. I think it's a misconception about our business and I don't know how to get people to stop writing that. But I think the perception was we just used UGC videos, but we didn't. What we did was we built our own camera technology for the iPhone and then we paid people $20 to go to certain games and film stuff that we then published. So it was actually an end to end network where we had a deployed army of maybe 800 iPhone filmers who used our software, tagged it and did it. But for some reason people thought that that was ugc and that part I'm. Look, I'm answering your question and I haven't even published a UGC video like that for nine years.

[B]

Over time, of these 800 kids, are you able to find ones that are just like spectacular and you're paying them more, you're giving them more roles? I feel like there's a lot of surface area for finding rock stars.

[A]

Yeah, some of them work for us now like full time and they started when they were 16, just like filming games for us. But over time we also ended up starting our own leagues. So I didn't need to have 800 people, but there's definitely people work at the company and that's how we know them.

[B]

What kind of business ideas or other opportunities has working within overtime shown you that you're too focused on to chase after?

[A]

I think TikTok shop is super interesting. I think that a lot of products are going to be driven by creators. I think that product categories are going to change over time. I think we're in a like a food product world where functionality is a huge aspect of that. So I think that's pretty big. I think that second, colleges which engage nil name, image, likeness to play a part in attracting athletes. There's just going to be a lot of change in that space. I mean, you know Reggie Bush lost his Heisman trophy and then four or five years ago, now people are making millions of dollars in college playing sports. I think it's an incredibly growing and disruptive space. So those are two that I would think about where I it's not on exactly for the business, but I think there's the opportunity there.

[B]

What about the genesis of 67 water? How did that come about and where's it at today?

[A]

Similarly I oh, there it is. You Know, we built a water brand off of a meme. I picked water because it was just easy to make and we didn't have to do testing and tasting and stuff like that. We turned around the whole thing. In eight weeks, we've sold tens of thousands of them. We have 41,000 people on our wait list. We're one of the most followed water brands in the world. But right now, we have a couple interns who go to gas stations and bodegas in New York, and they just talk to people and they're coming back and they're saying, you know what? I think we need a flavor. And this is why. So, like, it starts as this kind of instinct. We're sitting in a room and we're like, this would be crazy. Let's do it. But now a lot of the decisions are being made because people on the street are spending time with bodega owners and talking to kids in middle school who come in to buy a drink and seeing what they're buying and asking them why. So I wouldn't call it market research, but I'd call it, like, customer development and a deep understanding there. And that's going to drive the product innovation, as it should.

[B]

Yeah. Are you still looking for distributors and you're still trying to scale that?

[A]

I'm really focused on distributing it in Kentucky, where Taylor Kenney, who is the main athlete who started this and started 6, 7, and everything else like that, lives, A, because he's from there, and B, because I feel like everyone who makes a product tries to launch it in la, San Francisco or New York, which is a really hard place to get traction. So I just somehow feel like maybe Kentucky's the right place to launch it.

[B]

Yeah, it's so funny. Like, I thought that thing was going to die. The 6, 7 was going to die a month ago. Six months, five months ago, like, a month after it came out. I have four kids between the ages of nine and 15. And so when I. When I heard you on MFM, like, explaining to them what it was and what it meant. Doesn't everyone know this? Like, I hear it ten times a day. It's everywhere.

[A]

Yeah, I mean, you know, I think always think, like, culture is at its peak, and then it gets to a higher peak and a higher peak. Definitely, when it's in the Wall Street Journal and on the Today show, we might be towards the end, but when we started this, we were not there at all. And I also think there's aspects of culture that are exclusionary. If, you know, you know, and there are aspects that are inclusionary. And I actually watched this TikTok from this mom, and she was saying, like, the thing about 6, 7 is everyone can say it and everyone is in on the joke. And there's actually not a lot of things that are really inclusionary, like on a broad level, where if you're cool or you're not cool, if you sit in the front of the class or the back of the class, if you're a jock, if you're not a jock. So I think that in a way, looking back at it, there's a deep understanding that there was some power to it that just, it was just funny. And I, I think, you know, the idea of, like, monoculture, like, we're all watching the same thing, or everyone's going to see Taylor Swift or whatever, those things or the super bowl, like, those things are less and less than I think when we were kids. But when they happen, I think it's just funny. I mean, my grandparents were still alive. They would probably think it was funny to say that. I don't know those types of things on a participation basis. Like, people are too obsessed with the fact it doesn't mean anything. Nothing means everything. Everything is a word, is just a symbol with an arbitrary meaning attached to it. So, like, that's not the point of it. The point of it is it's fun, it's funny, it gives people a way to be included. I wrote this on LinkedIn, but I forgetting that it, like, comes with the hand gesture. Like, I can say, what's up? But there's no hand gesture. So, yeah, sometimes you like, I'll watch like a baseball game or a football game. People are doing this in the background. You know exactly what they're doing. Even with the sound off. It just, it was meme, so to speak, that just was built for video social school camp, everything.

[B]

Well, it doesn't hurt that the two numbers are right next to each other. So we're going to be hearing them together forever. And it's going to be hard to, like, untrain our brain to not hear it in that tone. How many students have you taught, give or take, roughly?

[A]

Probably 400 to 450.

[B]

When you talk to a student, you're five sentences into the conversation. What's something that you hear or notice that just signals to you, this kid's got it, he's going to make it, he's going to be okay.

[A]

Interesting. I thought you were going to ask me a different question, which is like, what are all the misconceptions about life they have.

[B]

I'd like to hear that too, but.

[A]

It'S hard to know that unless you're talking about like a specific assignment or anything else like that. If you look at a class, most people don't ask any questions. Some people ask bad questions and other people ask really, really good questions. And people ask good questions. You get it. They're just people who, they think differently, rate at a different level. Like they're confident about the knowledge, they're engaged, they're not asking you if it's going to be on the test. It's an in person class. So I'm biased because people with interpersonal charisma I make, I run out of time every year, but I try to make every student stand up and tell a personal story about something that happened to them in their first year in New York City. And sometimes you just realize like, some people are just really gifted and or some people are just really fearless and the rest of them are just like, is it going to be on the test? Or I go to do the grading and I'm thinking like, I don't even know who this person is.

[B]

What's a category or an industry that you have no experience in but just kind of you're obsessed over for some reason, something you find interesting.

[A]

I pay a lot of attention to skin care and beauty. I don't really know anything about it. On the influencer side, it was the first business that influencers were really, really successful in. It feels like cutthroat competition. Like this is the brand now, it's not the brand. I really like packaging and like visual communication, information. It's fascinating to go into a Sephora and look at all the design stuff. I like functionality and health. So trying to understand what's functional and what's not functional. And then I like the idea of products that make like clothing or makeup or that, you know, they'll be like skinny leg, wide leg, like it's not trends. It's like, what are we all doing together to express who we are or who we aren't. And I think those things are super interesting.

[B]

You mentioned early on that you're very focused. Like you focus on things. You also have a broad array of knowledge. You've been in different industries. How does that balance? What are your thoughts on focus? When is the right time to focus? When is the right time to chase the shiny object?

[A]

I'm very obsessive. So I have a mesh network in my house and like a D link in the basement with like 18 different ethernet cords that came in from when I renovated my house and put jacks and everything. And everybody complains the Internet sucks in our house, it's too slow and this isn't working or whatever. So I have this week, probably spent 12 hours like so deep. I just got one of those tools you stick in the wall and you measure the eight pins and whatever. And my son says to me yesterday, he's 24, he's like, why don't you just hire someone? Like, like you're spending so much time on like trying to figure out why the, why these are like full gigabit and these are not. And I was just like, I'm not giving up. Like I just will not give up. And then last night he's like, wow, the Internet. My room is really fast. Everywhere else it's slow, but at least in his room is fast right now. And I was like, no, I haven't figured out the other eight rooms in the house and I know I can always hire someone and then I'll give up. But I'm, I'm like crimping and cutting the ends off and yeah. Old things and whatever and I'll probably never use. I'm just like, I will figure this out.

[B]

Yeah, well, and you're going to appreciate the Internet even more when it's your Internet.

[A]

Right. That part I just don't, I don't want to lose. Like, yeah, I have like hundreds of chats with chat GPT where I take pictures of the back of the thing and I'm oh yeah, wrong with this wiring. Is it this end or that end or the other thing? I walk around with my laptop. So it's like, it's like starting a company or something like that. You just get so obsessed that you have to figure it out and make it work. And that's what it requires. When people are like, oh, I own four businesses. I'm like, well you own them maybe, but like I don't know how they can be great because like for me I, I just gotta be obsessed and all in and thinking about it non stop to make it great.

[B]

Yeah. Regardless of the industry.

[A]

You don't care regardless. I mean I, I care about like there, there's a limit. I, I'm not gonna do anything in, in like chemistry, for example. Like I will never understand it and there are things that I tap out on, but other things, especially things that are consumer oriented or culture or like I always say, like I learned so much. Like a lot of what I learn about business I learned from culture. Like I was a big watch of the Wire and Breaking Bad, and it's not like, oh, I learned tactics about how to start my own lab or how to sell drugs and projects. But I'm like, what is compelling about these stories and why do they resonate with people? What do they have in common? And even if you look at now, like, K Pop, Demon Hunters and Stranger Things are actually the same story, they both have an underworld. They both have kids who alert adults to what's going on in the world. They have all of these things that are very similar, even if they didn't watch each other's shows. So it says to me, like, oh, we live in this time of anxiety where young people don't trust that grownups are going to be able to figure that out. And when was that true? Also in the early 80s, like war games with Matthew Broderick. Like, those themes don't always exist, but they come and go at times when young people are like, I don't really feel that. And I tie that to, like, my overall thinking about, like, why are a lot of young people really into wired headphones right now versus AirPods? Like, I love AirPods. Well, I think to some extent they're just like, how long am I going to trust that technology is better for me? Like, what if I just have a bunch of headphones I don't need to charge, and one doesn't fall out when I'm riding my bike? And, like, I'm good. And so those, to me, are cultural indicators that I pay a lot of attention to and I try to feed back into what I'm creating or working on.

[B]

Yeah. Was there something that I should have asked you that I didn't? Anything you want to get out there to the world or anything interesting?

[A]

What are the things that your students ask you that or misconceptions or whatever?

[B]

I'd be curious to hear that as well.

[A]

Whatever you major in does not matter. Your grades do not matter. And whatever your parents tell you, you should probably not listen to them because it's your life. And I also say that saying that most people's parents still have probably had one or two jobs their whole life, and most young people are going to have 10 jobs given everything else, like, when you're 21 or 22 or you're graduating, like, you can either live somebody else's story or you can write your own story. And it's way scarier to write your own story. And it's way easier to do what everyone else is doing because the rules are really explicit and you know exactly how to do that. And it's way more risky to try to write your own story. But if you are connected enough to the world, it can be also way more rewarding. And I think like the beginning part of our conversation, School and education and a lot of, you know, functional things that we experience growing up, they tend to go like this. We tend to like, like five year olds are crazy creative and into dinosaurs and trains and I don't know what your kids were into, but like, it's all that stuff and it just kind of all goes like this.

[B]

We beat it out of it all.

[A]

In this little realm where we want to do this, we want to do that. And I'm just like, if you can break out of that, there's so much crazy potential in the world.

[B]

Yeah, Beautifully said. That inspires me to get my kids to do more weird things, honestly.

[A]

Yeah, 100%. Or just, I mean you, you probably do it, but it's like we all do as far as you indulge them. I mean, I used to know the name of every Thomas the Tank Engine train and whatever else. I could barely remember them. But like the passion of like a 5 year old who's so emphatic over something, it's like, it's incredible.

[B]

Yeah. So with that in mind, my final question. Passion or profit? Follow your passion. Follow the profit.

[A]

There's two aspects of passion. One aspect is like, I'm into poetry, I'm into music, I like sports. I don't think you have to follow your passion for that. That your passion may not correlate with a high likelihood of gainful employment. You might love poetry, but there's no job. You might love books, but you're not going to be a writer. And that, that industry is small. But I think you can have passion for things that you do. Accounting, marketing, talking to people, sales, live events. Like as you get out in the world, you're just like. And you know what drives that passion? A lot of times you're good at it. Like, I know people who have changed careers in their emergency room doctors, and they're just, you know, they're so good at it that that's what, that's what the passion is. And I just think separating that idea that the passion has to be your interest versus the thing that you might actually be really good at, because we're all really good at something. And it's just a process of unpacking that.

[B]

Dan, thank you. That was amazing. Where can people find you if they want to reach out or sell some water.

[A]

Tfadp on Twitter and on pretty much every social platform. All right.

[B]

What'd you think? Please share it with a friend, and we'll see you next time on the Kerner Office.