Ep. #2, The Pre-Keen Years

Kevin Wofsy: Welcome to Data Science Storytime. I am Kevin Wofsy.

Kyle Wild: I'm Kyle Wild.

Kevin: We are here to talk today about whatever comes to mind. We're going to start. I'm going to ask, Kyle, when did you decide to become an entrepreneur?

Kyle: Whew, that's a good one. When did I decide to become an entrepreneur? I'll flip it around. First of all, when I decided, I probably didn't have that word in my vocabulary.

Kevin: That's probably true. I grew up looking at comic strips that showed kids with lemonade stands, and I thought, "I've never seen a lemonade stand in real life." But that seems to be the image that we have of kids who start a business. You put out a cardboard box and you put a thing of lemonade on top. And I'm wondering, did you have a lemonade stand? And if not, what did you have?

Kyle: I had so many things like that. The very first one, I think, is probably third grade or something in that range. I grew up in rural America, kind of middle-of-nowhere, hour-drive-just-to-get-groceries kind of place.

Kevin: How many people in your town?

Kyle: Now? Fewer than a thousand. At peak, maybe closer to 50,000. It's kind of a ghost town.

Kevin: It was a ghost town when you were growing up?

Kyle: It became a ghost town before my very eyes, in almost about 15 years.

Kevin: A great place to start a business.

Kyle: A ghost town, but there were guns, though. A ghost town with guns. So what do you do? The grocery store's an hour away, so you've got to buy more groceries, right? Where I live now, grocery store's across the street. I go over there and I buy one avocado, and I go back home and eat it.

But if it's an hour away, you've got to stock up. So we had a Sam's Club membership, which is kind of like Costco for people that don't know what Sam's Club is. So, at Sam's Club you buy 36 of whatever, 48 of whatever. So we'd buy the 36 Famous Amos cookies.

Kevin: Okay.

Kyle: And they're delicious. Everybody loves those little Famous Amos cookie bags. Those little bags of cookies are the best. It's like 12 fucking cookies, 12 cookies, and we would buy so many of them. As I was packing my lunch before school, I would just pack two of them. And I built a little bit of a business where I would sell one and sometimes both of them for a quarter each.

Kevin: How did you decide on the price?

Kyle: I don't know. I don't remember. It's been a long time, Kevin.

Kevin: Okay.

Kyle: It's been like 25 years. So, I was selling them for a quarter each, and it was kind of a great business because we never ran out. Any time we got low on Famous Amos cookies, those would go into the next time we go out to Sam's Club, my parents would buy--

Kevin: Right, you wouldn't buy them.

Kyle: Buy more of them, and it turns out they were paying more than 25 cents each for these cookies. But I wasn't paying anything. So it was a beautiful business.

Kevin: Wait, wait. Were you aware of this financial fact at the time?

Kyle: No, no, no. I learned this after the fact.

Kevin: Okay.

Kyle: When they found out about my business, my dad was like, "This doesn't work. You can't just take shit from the family and then sell it for less money." We were not a rich family. We were a scraping-to-get-by kind of family. So that's probably the earliest. I had a bunch of these.

I had one, and this was fourth grade, I remember this was definitely fourth grade. I remember the teacher which was I found that there were a few people in my class who were really good at drawing comic strips but not very good at writing them. They weren't funny enough and they weren't interesting.

So I decided to join forces with them, and we took requests from people in the class for things they wanted to see, usually about this teacher, or Ninja Turtles was a big one, sometimes combined, and we would take requests.

I was kind of the creative manager, the band manager and sometimes the copywriter.

Somebody would say, "I want a comic strip that does this." And they'd give us a dollar, and I would be like, "Hey, you should make this comic strip. I will give you a quarter for this." So I did that for fourth grade.

Kevin: I'm sorry, combined the teacher and the Ninja Turtles? Can you give me an example of a storyline that would be requested?

Kyle: I can give you one.

Kevin: Make it up if you need to.

Kyle: Yeah, I was going to say I have to make it up. I don't remember specifically. But something like, the principal stepped down, he was still kind of around, he was super old, just like make him Splinter, that kind of thing. He's like teaching karate

Kevin: Splinter...?

Kyle: From the Ninja Turtles, the rat sensei.

Kevin: Oh, I see. Okay, got it.

Kyle: It would be something like that, or there'd be something, people in the class, like four boys want to be the Ninja Turtles, they want to be dressed up like the Ninja Turtles.

Kevin: And then do they each pay, or is it a flat fee, or is it a dollar each time?

Kyle: Yeah, you know, the business model, I didn't take very good notes or records. Which turns out is important because I also didn't pay taxes, and you don't want a record if you're not paying taxes.

Kevin: Okay, it was an all-cash business that you were running.

Kyle: Yeah, my first businesses were all very much all-cash businesses.

Kevin: Although the first business was stealing from your family and selling at a loss.

Kyle: Stealing from my family and selling at an infinite margin, because, not a loss for me.

Kevin: Not to you, correct. I mean, if we already write off the fact that it's stolen, then you're right, it's an infinite margin.

Kyle: It's like what today a cloud company builds their whole company on free credits from Amazon or whatever. It's kind of like that. It's like, "Hey, free credits and then you sell stuff."

I don't think I was ever like, "I will be an entrepreneur." What I was thinking probably at that time was, "I want to buy a baseball card, and I don't have any money. I'm going to get me some money." And oftentimes, entrepreneurship and "I need to get some money"...

Kevin: And you wanted the quarter more than you wanted the cookie?

Kyle: No, I had it both. I had it both ways. I had all the cookies I wanted.

Kevin: Oh, that's true, because you had a 48 pack.

Kyle: Yeah, it took a while for them to sort of do the math. So that's in terms of the sales side. There's a whole bunch of, I grew up with a brother, you know my brother, we both eat a lot, or we both have strong appetites.

Kevin: Yes, you do.

Kyle: So, my brother, Dr. Pepper and Coca Cola. I was the only one that liked Dr. Pepper, but we would always have a 24 pack of each. And then I realized, "What I'll do is I'll drink Coca Cola for the first few days when we get back to the store. We'll run out of those and then I've got the market cornered on this Dr. Pepper. Nobody else wants it."

So I would drink my second favorite while it was competitive and then I would drink my favorite once we're out of the Coca Cola. And these kinds of weird life lessons actually do translate into life.

Kevin: I don't understand that one. Where's the benefit to you of drinking the Coke?

Kyle: We'd go to Sam's Club every Sunday after church, right? We come back home with all the supplies, and we've got a week and we buy Corn Pops and Dr. Pepper and Coca Cola, whatever. Well, it turns out we only had 24 Coca Colas, and I was competing for those.

The way to maximize my soda intake was, "Well, no one's going to drink the Dr. Pepper besides me and sometimes my friends." So I could compete with my dad and brother over the Coca Colas while that market was competitive until they're all gone.

Kevin: And then you're the only one in the house with a soda

Kyle: And then I'm the only one who has soda for awhile, so I'm just kind of enjoying my Dr. Peppers, three a day for the last few days, because who cares? Five, whatever, it didn't matter. I had friends over, I'd give them Dr. Pepper. I always had that stuff. So no money changing hands, but there's an entrepreneurship. I don't know how to describe it, but it sounds like an entrepreneur. I don't know exactly what words to put on it.

Kevin: It's certainly sneaky.

Kyle: Is sneaky one of the ways, is that one of the entrepreneurial traits?

Kevin: I don't know. You tell me.

Kyle: Strategic? Asset allocation? Whether there's cash changing hands or not, is certainly part of the gig. I kind of always knew, when I was a kid, I wanted things and we didn't have a lot of money. So they'd have to tell me we can't get those things and they would joke about it, my family would joke about it, like, "Man you better grow up to make some money, because you have expensive tastes." Because I wanted like Red Lobster or whatever.

Kevin: How far did you have to go to Red Lobster?

Kyle: Red Lobster was about an hour. The nearest one was probably in Carbondale, about 60 miles north.

Kevin: And that was your favorite?

Kyle: Red Lobster was my favorite. That was my birthday treat.

Kevin: And what'd you order?

Kyle: The main thing that I remember the most was probably Seafood In Every Bite Pasta... I see the advertiser in you cringing, like, "That's such terrible branding."

Kevin: No, I'm remembering the day, because you say you grew up poor and that Red Lobster was a special treat. In my family, I wanted to go to Red Lobster, and my parents said, "That's too expensive. That's too fancy for us." And then I never went to Red Lobster until the one time you took me there when I was in my 30s. And you said, "We're going to Red Lobster."

I couldn't go that night and I said, "But that's my dream." I didn't even know it was my dream until you threatened to go without me and you were kind enough to postpone it. You said, "You know what? We'll go to Red Lobster tomorrow so you can come." And as I recall, none of us enjoyed it very much.

Kyle: It was terrible. It was really terrible. The place has two stars on Yelp, I think, right now, the Red Lobster in San Bruno. I mean, I grew up certainly not poor, certainly scraping, but Red Lobster was sort of in my teens, like 13 or 14, we'd done a lot better as a family. Eventually my parents retired early and bought a house with a pool and an RV and stuff, so.

Kevin: I'm really glad that stealing those cookies didn't bankrupt the family.

Kyle: No, no. But it was very often, I'm from the Midwest, blue-collar family, kind of the first generation to go to college were my brother and me. So there's this interesting thing in the value system in the Midwest, and certainly the Bible Belt, sort of toward the South, which is, "Hard work and discipline, and don't complain." And that's the value system, right?

My dad, bless his heart, he always tried to teach me those values. And if you know me very well,

I do as little work as I can. And I'm not particularly disciplined. And I complain quite a bit.

So it didn't work, didn't take. But you try to use how you're raising your kids, you know, chores, allowances, tying chores to allowances, and that kind of thing to teach these kind of lessons. And I just always, I didn't want to learn the lesson that I should go mow the lawn in 105 degree weather, 100% humidity.

We had huge lawn and a lot of it wasn't even ours. It was just attached to the woods. But I'm going to mow that, too. I didn't want to learn the lesson that I'm going to do that and get like three dollars. That's not a lesson I wanted to learn. But what I did figure out was I could get three dollars a whole lot easier and pay somebody else to do that. So what I learned was, "Oh, three dollars is going to get me out of the work." What I was supposed to be learning was the work would give me three dollars. I never learned that lesson.

Kevin: You paid some other kid to mow the lawn?

Kyle: Yeah, I figured out at a pretty early age, at about 13, I figured out I could make a whole lot more money on the internet than my whole month's allowance just by making websites, putting some ads on them. At peak I made $300 a month through one summer, just from a website about video games. It was all fun. I was learning a new program. I'd put stuff on the internet, put some ads on it, people would click on the ads, I get money.

Kevin: What do you mean it was about video games? It was just you rating them or what?

Kyle: Yeah, I made a website called Final Fantasy Fever. There's a bunch of nerdy Japanese nerd games called Final Fantasy. At first I just sort of, there's no two ways to put it, I would pirate a bunch of content other people had written about these games, and I would grab all the music and MIDI files and all the art, and I would just index it all and put it on the site.

Then I conned my way up to the top of Yahoo for Final Fantasy, so people would always find my site. And then eventually I wrote my own content as I got older and could actually contribute. But I was honestly just taking content from other sites and putting them in one place and I would make 40 times my allowance doing that.

And then I could just pay somebody to mow the lawn, and my parents were like, "You don't get it. You're not getting it." And I was like, "I think I am getting it." I think I learned the lesson. I don't want to have a job where I mow the lawn, so I better figure out how to get three dollars or whatever the dollar figure was.

It turns out a lot of entrepreneurs have that weird set of stories from that age range, where it's just a mindset that there is an equivalency between labor and capital.

You could use your labor to gather the capital and then hopefully you can get some vacation time. Or you can retire, which means you're not forced to work just to eat. I rejected that mentality. I was like, "Well, I could also just get out of labor by finding other access to capital."

Kevin: What about, aside from the money, you say that you made your way up to the top of Yahoo. I bet there was a certain competitive streak there, just to see your site gradually crawl up through the rankings. Am I right there?

Kyle: A little bit competitive. I never got to the top. The top was the actual website for Final Fantasy, the actual game studio's website. So it got to number two, the first of the "not official." A little bit competitive, yeah. I'd say I was a little bit competitive with a few other sites. I still remember them all by name.

Kevin: Let's hear some of them.

Kyle: RPGnet, eventually later on, I became a writer for RPGnet. I'm Facebook friends with the creator of that site. He's still in software. RPGamer, RP means role player. These are all role playing games. RPGamer, which eventually beat me.

Let's see, there was this thing called Korra Fire's Squaresoft Homepage. Squaresoft was the name of the company that made these games. Turns out that guy lives a couple blocks from me in San Francisco. He's a programmer. We'd known each other online for years before we figured out that we knew each other online 20 years ago when we were kids. But I was competitive with that one. If I remember them by name, yeah, I bet I was competitive.

But honestly, first and foremost it was looking out for number one.

The more traffic I got, the more people looked at ads on my site, the bigger the ad revenue, the bigger the check was that came in the mail. And I would just take it to the bank with my parents and spend the money. I didn't know about taxes, incorporating an entity. I didn't do any of that.

Kevin: And how old were you?

Kyle: This was from 13 to maybe 15. And then somebody made an offer for the domain in like '01, so I was maybe 16.

Kevin: Oh, so you sold the business?

Kyle: Yeah, well, I sold the domain. There wasn't a business really to sell. There was no legal business.

Kevin: Did you negotiate?

Kyle: Not really, no. At this point, the ad revenue, even though my traffic was really high, my ad revenue had come down to $30 a month, and I couldn't figure out why. I thought I'd done something wrong. I became obsessed with analytics, trying to figure out, "What the hell is going on with my money? Why am I not making ad money now? I've got way more people on the site."

Final Fantasy VII and VIII had come out the biggest, Final Fantasy VII is still one of the biggest games of all time for consoles, and there's so much more traffic and the server bills had gone up a little. They still weren't very big, but the ad revenue kept coming down, and it turns out, I now know, there was this whole thing going on out here in the valley called the bubble. It had popped. The people buying those ads were like Webvan. They're not real businesses. They just had a bunch of fake money they were spending on ads.

Kevin: And vans.

Kyle: And vans. And so the whole thing was propped on this venture economy that I now know intimately well, but I had no concept of this.

Kevin: I lived here at the time. I was a working adult at the time. I lost my job in the midst of that. But you were just a kid.

Kyle: Yeah, in a way, I lost my job. In a way, because I had told my parents by then I was never going to go to college, I was like, "I'm not going to go to college. That's stupid. This site took me this many hours, and now I have $300 a month forever. If I make 10 of these sites, I make more than you, and you're a nurse. You work all the time. So I just need to make 10 sites. So I'm not going to go to college." And I had this whole roadmap of different game series I was going to go after and make websites.

Kevin: So,

the reason you went to college is because there was the dot-com bust of 2001 in Silicon Valley?

Kyle: One of the reasons. It's complicated, but that's definitely one of the reasons. I guess, at its core, I went to college to come out to Silicon Valley. And the original cause was the Silicon Valley bubble burst. There was no opportunity here at the time.

I never really thought about it like that, but I became obsessed with knowing what was going on and why was this happening, and I couldn't figure it out. I was like, "Well, somebody made an offer. Sports Illustrated or somebody inside of Sports Illustrated made an offer on the domain because the domain was "thefever.com," which was a decent domain.

Kevin: Oh yeah.

Kyle: And then I sold it for like $2,500, which I calculated was more than I would ever make again based on the pattern of more people coming to the site and clicking on ads. It went from, I would get like $4 a click to like 4 cents a click. It was night and day. It was crazy how quickly all this stuff changed.

Kevin: Yeah, I went from getting a paycheck every month to being out of work, so.

Kyle: I had heard of Silicon Valley. I didn't even know it was related to what I was doing, because I'd seen this TNT movie called Pirates of Silicon Valley about Steve Jobs. And I watched it and I was like, "I want to go to Silicon Valley and be a pirate and I want to start a computer company in Silicon Valley." But I didn't know it was actually related to this.

Kevin: I'm showing you right now that thefever.com is not being currently used, so I think you sold high. I think you did a good job.

Kyle: I think I sold high.

Kevin: I should probably buy that. You can buy it back.

Kyle: I almost cried when you showed me that.

Kevin: I know. I think you should buy it back before we air this episode.

Kyle: Right, this episode is going to be wildfire

Kevin: And thefever.com is going to be the thing.

Kyle: Yeah, it's going to be huge. I heard Beyonce wants to buy it.

Kevin: You didn't hear it here. So, that was high school. Then you did go to college?

Kyle: I did go to college.

Kevin: And you've now sold thefever.com, so you're without a business. Does the itch strike again in college?

Kyle: Yeah, to some degree. One of the things that happened in college was I had a little bit of a burn rate. My parents helped out as much as they could, and I still had to cover some stuff. So I ended up working a couple jobs.

It's kind of interesting, the amount of risk you'll take when you've got to cover your food, water, shelter, your bases. You won't take as much risk.

Instead of scamming my way into zero-labor, four-hour work weeks, those spam emails that are like, "I make $100 a day on the internet without doing anything," that was my mentality before. But once I got to college, I was in the dish room making $5.15 an hour, which was minimum wage at the time, which is very different.

I was kind of learning that lesson that my parents wanted to teach me, which was you got to go and do awful shit and get barely paid for it, and that's life. And there I was in college for engineering school.

University of Illinois is interesting. It's the local state school. It's a good school, and you've kind of got pretty bright but not particularly wealthy kids, like a lot of my friends. And then you've got kids from the suburbs whose parents did very well and they're going there because it's a good school. And there's clashing.

So I was in the dish room, covered in slop making $5.15 an hour. And some of the kids in my class didn't have to do that, including my co-founder Dan, who didn't have to do that, if he's listening to this.

Kevin: We'll get to his side of the story.

Kyle: Yeah, eventually. But we would do things. We would throw these college parties. We had a big house junior and senior year where we'd throw these parties and we'd always try to cover the kegs and then make as much money as we could. Basically, we threw illegal underage drinking parties.

Kevin: I think,

the statute of limitations, we'll make sure it's passed by the time this is aired.

Kyle: Yeah, because we were the only ones at the University of Illinois doing that. And then you'd sell these cups for $5 a cup, and it was like, we were underage, too. So it's not nearly as bad if you're also a minor. So whoever sold us the kegs, they were really breaking the law.

And then we would do all right. We would get to a point, sometimes, at a party you would sell 150 cups and you'd think, "Oh, that's like $700. The beer was only $150-200." But then we'd always get these noise tickets, and we'd barely cover the, there's noise complaints and all the other--

Kevin: You got away with the underage drinking and the selling of alcohol to underage, but it was the noise?

Kyle: Yeah, so, let me tell you something about Midwestern state school college towns. They don't really bust a lot of underage drinking, because it's sort of the economy of the entire town. This is a place, Urbana-Champaign, IL. Urbana's kind of like mature, because you have to be 19 to get into a bar, whereas in Champaign, it's 18 to get into a bar.

Kevin: Wait, I'm sorry?

Kyle: Yeah, exactly. You can't drink or be served.

Kevin: But I thought Urbana-Champaign was one place.

Kyle: No, it's two towns, two cities, kind of a twin-city thing.

Kevin: And are they in different states?

Kyle: And it's maybe 100,000 people, but 40,000 of them are students. So it really is the economy. So, no, I don't know if I know anyone who got an underage drinking ticket. But things like noise complaints, things where you can get a little bit of revenue so you can have your minor drink party...

Kevin: And wasn't your other, I mean, I know you went to college with the other co-founders of Keen. But were you all in on this cup racket together?

Kyle: A few, yeah. Ryan and Michelle and I were definitely at the--

Kevin: The apex of it?

Kyle: Yeah, we were the masterminds of it. Micah, our designer, was part of it. He moved in senior year and he was a big part of it, big party planner. So yeah, a lot of people from the Keen world.

Kevin: Dan has clean hands about the cups?

Kyle: Dan has never broken a law once in any fashion. I swear by it.

Kevin: Yeah, sounds plausible.

Kyle: Yeah. He drives, he speeds, he drives really fast. So, we did those kinds of rackets. I had all kinds of little schemes here and there, but honestly, the game I was scheming was, "How do I get a degree and do as little as possible?"

Kevin: Well, that's college.

Kyle: Then I found out that there was a GPA requirement to get into Google, which was a company I wanted to join. And so then I was like, "How do I boost my C+ GPA up to where they need it, while doing as little as possible?" It was really still very "hack the system," entrepreneurial, but it was much more about that. That was the whole reason I was there.

Kevin: I just want to interject a second to say the way you're talking about "hack the system," I get it. But I also think of you as a very idealistic person. It's two sides of a coin. You also talk often about a better way of doing business and a better way of working and treating people better and being honest.

Kyle: Yeah.

I'll be the first to tell you that it is stupid that there was a GPA requirement, for instance, to get a job at Google.

That's stupid, really stupid.

Kevin: Why?

Kyle: Well, there are a few reasons. One of them is that they were actively, and they still, they don't have that GPA requirement anymore. Actually, I think it was Larry Brilliant, their Head of Talent, who wrote a piece on why they were getting rid of it. That piece actually points to a lot of the reasons it was stupid.

But in my own words, they're looking for divergent thinkers, and if you only get 4.0s from the top 10 schools, you're going to get convergent thinkers. Overwhelmingly you're going to get people who are really good at, you're selecting on "really good at following the rules and following a syllabus" and then you get in the workplace and there isn't always a syllabus. Some jobs there is, but not in all jobs. That's number one.

Number two, it's regressive, right? Like, yeah, I was lazy, yeah. I didn't go to class all the time and I partied. But I also had two jobs, and in addition, that makes it harder to kind of grind out the GPA. I was a cart boy at Sam's Club. I was working at the dish room. It's regressive in a fashion.

I think what they're trying to select for is people who were smart enough to get a 4.0 but it turns out, most people who get into a good school are smart enough to get good grades at that school or talented enough or diligent enough or whatever, all other things being equal. But the reality is all other things are not equal. I'll be the first to tell you the system is broken.

Given that the system's broken and I'm in it, I'm still going to play the game.

Kevin: Is the cups the last of your ramshackle businesses? I want to round out today with, this is the early story, the pre-real business story. So, what comes after the cups, or is that the end of it? Is it that straight to Keen?

Kyle: No, you know what? There are probably 10 more, but we did, in college, we did a software company where we were making something, code name was called Dork Board which was basically a way for teams to communicate and collaborate in real time, chat based, very sort of like Slack today and a little bit kind of like Google Wave.

If you follow the brief life of a thing called Google Wave, where you can message your coworkers but then fork off and branch off subconversations but they're kept tidy instead of it kind of polluting the main thread, which was way ahead of its time. But it's funny, we talked to some venture-y, entrepreneurial advisory people on campus, and they're like, "I don't know how big the market'll be for that." Slack is worth quite a bit these days.

I had another thing called IndieCab. Really, I just bought the domain, indiecab.com, and then I built out the business model which was, I had a car and I had no money and I had a lot of friends who needed to get around. And I was like, "Oh, I could just rent out shotgun." I also thought about calling IndieCab "Shotgun": "You can just ride shotgun with me and you give me some money, and IndieCab will take a little bit off the top."

Obviously we're talking about Uber, UberX, Lyft today. At the time I abandoned it because actually my cofounder Dan, his dad told me, "You'll never be able to get around the taxi laws." Literally, this happened in like maybe '05, and I was like, "Oh, that's probably true. I don't know anything about taxi laws. I'm not going to pursue this one."

Kevin: Have you taken that up with Dan's dad since then?

Kyle: No.

If you start a company, lots and lots of people are going to tell you not to do it. The blame doesn't sit with them.

The status quo is the status quo because it protects itself. There's an immune system of the present. Anything new, we tend to criticize.

Kevin: It is true there has been a lot of fighting about the taxi laws.

Kyle: Yeah, it is true, and it's on me for not pursuing those things. With the chat system, actually, that's the farthest we got. We built a bunch of stuff, piloted stuff, but then people started graduating college one by one. I think Dan was the first, then Michelle graduated, my brother was on that company, he graduated.

Micah and I graduated a year later, but as people graduated from college, I found that they stopped working on our little startup because they would go get real jobs that paid them quite a bit, whereas this little thing, we didn't pay anyone anything.

Kevin: Indiecab.com redirects to dorkatude.com.

Kyle: I still own that one.

Kevin: So you still own it? Right on.

Kyle: Yeah, I saw the future.

Kevin: And you still have your piece of that?

Kyle: Proof I'm not full of shit and thefever.com, by the way, that's in Time magazine. You can look that one up. There's evidence. But I don't own it and I'll make sure I own it before this podcast goes out.

Kevin: Awesome.Good luck.

Kyle: But if anyone wants to spend more than $2,500 on it you just let me know.

Kevin: So does that bring us to the end of part one of the entrepreneurship story, the pre-Keen business life?

Kyle: "The Pre-Keen Years."

Kevin: The Pre-Keen Years. It's our version of The Wonder Years. The Pre-Keen years.

Kyle: I mean, there were a bunch more. The three of us that started Keen, about a couple years before, we spent winter break making this thing called IOU, which was kind of a bill sharing and settling up and receipt splitting--

Kevin: Sort of a Venmo?

Kyle: Sort of a Venmo.

Kevin: I like that you've basically been everywhere first and have not much to show for it except some domains.

Kyle: Yeah, that's one way to describe the narrative. Another is I went into places where there was clearly enormous opportunity, and my execution was just so poor that I couldn't even capitalize. I couldn't even sail a ship with a giant tailwind, is one way to look at it.

The first job after I quit Google, I was the first engineer at a company where we made a mobile social network for emerging markets and replaced the SMS systems in those markets: Sub-Saharan Africa, Indonesia, the Philippines...

Kevin: You mean like WhatsApp?

Kyle: Like a WhatsApp. In fact, this weekend, I had whiskey with the founder of WhatsApp and described it, and he was like, "Oh yeah. You started that when?" And I said, "'07" And he was like, "Yeah, we started in '09, but if we had started '07, we would've died because there's no way to raise venture in 2008." And that's what happened to us.

We died in June 2008 trying to raise venture-round despite massive growth. We needed the venture-round to cover the server bills, because this thing was hyper viral. Because in all these countries, people would send one text message to their friend and be like, "Hey Kevin, this is the last text message you're going to get from me. Sign up for this thing called Mobile Play. We're going to message for free from now on," like WhatsApp's viral distribution model. That's only the biggest venture acquisition of all time, like a $19 billion company. Again, timing or poor execution despite an awesome tailwind.

Kevin: That's what I think is so great about you and so different about me, is you don't dwell on the past. You're looking to the future.

Kyle: I mean, I look to the future. I don't dwell on the past. I'm mostly motivated by learning. I learned some things from these experiences. Like, with Dork Board I learned, I better figure out, new founders talk sometimes about this in literature, this catch-22 problem or chicken-or-egg problem where you need talent, you need people to build a product, you need a product to make the revenue or traction. You need the revenue or traction to raise capital and you need capital to pay the people, so where do you start?

With that Dork Board thing, we were working for free while we were in college. But then as soon as they graduated, I was like, "Oh, they stopped working. Maybe we should figure out how to pay people. Maybe I'll figure out startups or something, like venture or something." Because venture, the promise of venture capital, is you could raise money on just the vision and then use that to pay people to help you build the vision. But it took me 12 years from that point when I first learned that lesson to actually be able to use it. I don't dwell but...

Kevin: But you learn.

Kyle: Yeah, and there is a certain bitterness with each of these lessons.

I don't think a lesson is real unless it's kind of painful, when you think back to it right before you learned it.

It's like, "Wow, that guy was an idiot right before learning this lesson." So I don't really dwell, but there's pain. That's for sure. I'm like, "Oh, yeah. Uber, Slack and WhatsApp would be cool to have under my belt at 32. But no."

Kevin: At least you have the cred of the actual WhatsApp person saying, "Oh yeah, you were there 'first.'"

Kyle: Yeah, he's like, "Oh yeah, glad I didn't have to raise money in June 2008."

Kevin: Well, I think that brings us to the end of part one of the entrepreneur story of Kyle Wild. I'm excited about part two.