In this episode of the Founder Origin Stories, Sherry interviews Clay Collins a co-founder of Leadpages. They talk about his early entrepreneurial endeavors, his departure from Leadpages, and his hopes for the future.

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Episode Transcript

Speaker 1:This week in our continuing founder origins series, Sherry interviews Clay Collins, the co-founder and former CEO of Lead Pages. I’ve had the pleasure of knowing Clay for several years online, and we first met in person maybe eighteen months ago when Clay was about four or five months into the negotiation process for Lead Pages to acquire my company Drip; and it’s been great to get to know Clay on a personal level and I would consider him a respected colleague as well as a friend.
 Clay Collins came on the scene teaching internet marketing years ago and had a podcast called The Marketing Show that was one of my favorite podcasts to learn about tactical marketing, and then he teamed up with two co-founders and started Lead Pages in January of 2013. His origin story is fascinating; he grew up in California and later moved to Minneapolis and has really had a major impact on a lot of peoples lives by starting this company and bringing more of tax startup scene here to Minneapolis. If you haven’t heard him talk about his childhood, growing up being homeschooled and basically the story of becoming an entrepreneur, it’s quite engaging and I think you’re gonna enjoy it.
Sherry Walling:I think it was about, very close to a year ago, to the day, that I interviewed you from the closet of my new house while the movers were moving my stuff in.
Clay Collins:Nice, the closet interview.
Sherry Walling:Yeah, like literally I was in the closet; I was like hiding from everyone.
Clay Collins:Yeah, stuff was banging around in the background.
Sherry Walling:You were so gracious, you were like “We can reschedule.” And I was like “Oh, no, no, no, no. If I do one more thing related to moving or boxes, like I’m just gonna go crazy so please talk to me about some other part of life.” So I was in the midst of a giant transition the first time we did an interview and now you are in the midst of a giant transition; although not hiding in the closest.
Clay Collins:Absolutely true.
Sherry Walling:So what’s the big news? What’s the big transition?
Clay Collins:Yeah, so, the big transition is that John Tedesco, our chief operating officer has been appointed to be CEO of the company, the board and I did that after a search kicked off by myself. And I’m moving on to be a chairman of the board, but my day to day role in the company is no longer, so I’ll still be in the office probably on a weekly basis. Certainly every other week I’ll still be involved in high level strategy, and of course I’ll still be on the board, but my day to day operating role is no longer and it’s really exciting. It’s the right thing for the customers, the right thing for the company, it’s the right thing for me and it really happened in a genuinely organic way.
 John Tedesco, back at the end of 2013, started advising us just free of charge. We would meet for breakfast and we would talk about a number of different things and it almost felt like there was almost a karmic imbalance and Tracy and I offered him advisor shares … You know in the company he became an advisor and a little bit later on, I just started realizing how much we were leaving on the table by not having him, not having that level of advice and experience inside the buildings so we made him a job offer and later on he took it. He started off as chief customer officer then became chief operating officer and really everything he touched was better and then at some point I found myself on a leadership meeting where he had offered he put the agenda together and was driving everything. And I found myself essentially after every end of discussion just kind of turning to John and being like “So what do you want to do?” And then he’d make his recommendation and I’d be like, “Yeah, ok that’s what we’re gonna do.” So the transition over time was really organic and at the time that the transition took place, over 80 percent of our org directly, or indirectly, was reporting to him, so it was just a nice organic thing and I couldn’t be happier with how it’s turned out.
Sherry Walling:Good. I think about who knows John knows that Lead Pages is in great hands, but I can’t imagine what this must be life for you to have had this business be your life, your heart and soul for five years or so? And now obviously you’re still gonna be involved and Clay Collins has his mark on the company but your role, as it’s been is ending. How does that feel?
Clay Collins:It feels great. Lead Pages has certainly been my baby, but at some point that baby grows up and it’s time for it to go to college. (laughs) And you’re excited to be an empty nester again and I think that’s an appropriate analogy here. I know what to do, from zero to fifteen million in revenue. I like companies as they kinda get up through around eighty people and at some point I realized that a lot of the things that I needed to do, I no longer got energy from.
 So I think when you’re first starting a company, it’s about building the product, the vision, the strategy, you know, a lot of those early winds and at some point, I don’t want to say it’s less about the product, but it’s much about building the company that builds the product as it is about building the product; and at some point you go from unseating incumbents to being the incumbent and things just shift. So I think that introspectively I just started thinking about who I was, what my zone of genius was, where I was most happy, and this became not only a logical thing, but something that, in my heart, felt like the right thing to do and that has been confirmed at literally every step along the way.
 I think having seen the company go through a number of different phases and transitions, I’ve noticed that there are people that are perfect for one phase of the business that aren’t necessarily a match for the next phase of the business and sometimes we realize it and we have to part ways and sometimes they realize it and they go do something else and sometimes the whole thing just kind of drags on for a lot longer than it should and it’s just kind of weird and uncomfortable. And I could have made a role for myself. I could have been that co-founder that’s in the corner, popping into meetings and expressing their opinion and insisting on getting their hands into this, that, or the other thing and it just didn’t feel right. There’s a lot of things I’ve struggled with as the company has grown but this simply isn’t one of them.
Sherry Walling:This has felt pretty clear to you.
Clay Collins:Yup
Sherry Walling:So, usually in these origin stories conversations we kind of start from the beginning and I’m curious about that for you. What were the first moments of entrepreneurial spark in you?
Clay Collins:Yeah, a great question. It was probably growing up on a citrus nursery in Southern California and I remember going to a gardening supply store and seeing that dirt was for sale. I think I was seven, or between five and seven, and finding it really odd that people were paying a large amount of money for dirt. And my next thought was “Well we have dirt at home. I could package this up and sell dirt.” So I did that, and I had one buyer, it was my aunt, and I think she gave me two dollars for a bag of dirt that was just horrific, desert dirt.
 So that was probably the initial spark and then later on, my mom ran a fruit stand and I sold orange juice and I think it was versions of that all throughout my childhood; and then when I was fifteen, I sold computer lab management software to my high school and then later dropped out of high school to start a software company with some friends, again when I was fifteen we raised like 120 thousand dollars so I think I’ve always been an entrepreneur at heart, not only because entrepreneurial endeavors were exciting to me, but also it was a great way to opt out of the system and allow yourself to have success on your own terms. I’ve always had pretty bad ADD and whatever other co-morbid whatnot comes with that. Probably dysgraphia.
 And, as a child, I just needed to think and I would hide under the table in school. And so my mom homeschooled me. I remember winning the school spelling bee, but failing the spelling tests, ’cause orally I could do it, verbally I could do it, but in writing, I wasn’t as good. And so, the prospect of sort of rigging the game to play to my strengths instead of exhausting myself trying to compensate for weaknesses. That also really appealed to me as well.
Sherry Walling:What years were you homeschooled? Was that just elementary school on, or was that intermittent?
Clay Collins:Yeah, so, it was intermittent. I kind of attended a mixture of private school, public school, for like one semester and homeschooling but I was more homeschooling than anything else throughout my childhood. And then, you know, got into high school and I thought that sucked. But I actually did pretty well. In college as well I did pretty well academically also. But yeah, It was kind of off-and-on, but I took cumulatively, probably amounts to about six years of being homeschool.
 What I liked most about being homeschooled was that this artificial line between your learning environment and the rest of your life wasn’t drawn. I think people who are homeschooled often are likely to become entrepreneurs because, I think being homeschooled you’re forced to think a lot about what you do with your schedule. Are you quote-on-quote “keeping up,” and you have all this autonomy. I think if parents are doing it right you have all this autonomy and then you have to grapple with a lot of existential questions about how to use your time now that it’s yours. And a lot of insecurity around that, because you know everyone else has a set schedule and you don’t and so you think a lot about how to use use your time. I think in all respects it was a productive thing for me. It was one of the best things that ever happened to me, was that my parents decided to let me be homeschooled, which was almost entirely self-directed.
Sherry Walling:Yeah, you really learned to be the master of your own time and your own day when you’re homeschooling. Not unlike what it’s like to be an entrepreneur. So, I mean, you’re painting a little bit of a picture, and correct me if I have this wrong, but, I have someone who, for a variety of reasons really didn’t fit in a typical kid system. You know, whether it was ADD or academic learning differences or good old-fashioned, like, a little bit of deviance. Just not someone who was able to or wanted to tow the line of what everyone else was doing.
Clay Collins:Yeah, I think that’s spot-on.
Sherry Walling:How did that play with your family?
Clay Collins:Yeah, great question. On the whole, I think I have a great family. I was always, I think, a bit of the black sheep. There was a lot of television watching in my family. I think we were like a traditional family. You know, I grew up on a farm, but a lot of the childhood was spent living in the suburbs and I don’t know that outside of a very enlightened decision to homeschool me, I don’t know that our existence was that outside of the proverbial box. So, I mean, it was fine. I think people just trusted me. And that was nice. I never, I think, growing up, my parents were never like, “is your homework done?” They just trusted that I was capable of setting my own agenda and that whatever issue there was to figure out, I would figure it out.
 And there wasn’t this incessant anxiety parents have about their children turning out okay that caused them to force me to do X, Y, and Z. They just kinda were like, “That’s Clay. He seems to think he knows what he’s doing with his life and we largely trust that.” And that was awesome. I mean, it was really incredible. I think kids pretty much turn our great on their own if people, like, don’t fuck with them.
Sherry Walling:If people let them.
Clay Collins:Yeah, if people just let them do their own thing.
Sherry Walling:I have to imagine that your decision to drop out of high school, did that at least give them pause, or was it so clear at that point that this kid’s got skills, this kid has it figured out. He can just do what he needs to do.
Clay Collins:Yeah, so I not only dropped out of high school, I dropped out of high school and moved two hours away to live with the business partner that I had found at that time. So it was quite a leap, and a lot of people I think questioned my parents, primarily my mom. And I think again, she just sort of erred on the side of trusting me. You know, I think it takes, back then, at least, before Waldorf schools and all these sort of non-traditional private schools kind of emerged. Homeschooling was really weird back then, and I think she was questioned a lot on that, and I was questioned a lot on that.
 Like, “Why are you being homeschooled?” You have to answer that question over and over again. I was like, “Well, why do you go to a public school?” So you kind of, I think, get comfortable with living a non-traditional life and with all the questions people ask about that, and the unease that comes from that, and you kind of get used to being a weirdo. And at first that’s odd, but I think later on in life that actually becomes an asset. That you can decide to do things really however you want. And there’s just been so many different ways that in the rest of my life or later on in life, getting comfortable with living in non-traditional ways has paid off. So I’m glad my parents started me off doing that really young. Because it would have been a lot harder, I think, had I had to do some of the things I ended up doing later on without that.
Sherry Walling:It does sound like such a precursor to being an entrepreneur and to founding your own business. People are like, “Well, why don’t you go to school? Why don’t you go get a job?” I mean, you’re basically practiced at saying, “No, I’m gonna do it this way. I’m gonna do it my own way.”
Clay Collins:Yeah. It’s like, I’ve always been weird. This isn’t some break with anything. My friends are used to it, my family’s used to it. Everyone just accepts it at some point.
Sherry Walling:And what a treat that you’ve found a way for your weirdness to pay off.
Clay Collins:For sure.
Sherry Walling:Has it ever not worked out? Has your sense of, “I’m gonna do it my own way, I’m gonna go against the system and find my own version of life,” has that ever been painful, or has that ever come back to bite you?
Clay Collins:Not in any significant way that sticks out. I think if I were doing some of this stuff because I had a chip on my shoulder and I had to prove something or if I was motivated with any of these big decisions by doing anything other than marching to the beat of my drummer. I think that it would’ve been problematic, but as long as I’ve been true to myself and who I am, then the lessons, even when things don’t go how I initially anticipated — in fact, almost nothing goes how you initially anticipated. You know, those lessons end up being the reward.
 I think the only time it hasn’t really paid off was kind of an attempt to maybe live a more traditional life after the company that I started when I was 15, I left that. The company essentially failed. And I was really sick of this whole thing around being so independent or doing things so differently that I ended up swinging in the other direction. So I went to college. I ended up graduating top 5 in my class. To this day, my biggest regret of my entire life, really, is that I studied so hard in college instead of just really enjoying college. I was so motivated my doing well in school and then after that I started a PhD program in developmental neuropsychology. And that didn’t work out. So I dropped out of, well, I hopped on another adventure there. And that was the fun part, was the adventure that took me out of graduate school and then I started graduate school again and then dropped out of that.
 You know, I learned a lot from that period of my life, but that was kind of, if you look at the trajectory, the narrative arc of my life, that was when I went astray, was when I tried to fit into the traditional academic system again. Then when I finally broke free of that once and for all, that was when things started to work out again for me.
Sherry Walling:It sounds like that was the season of life for you. You had something to prove. Whether to yourself or to other people. And as you said earlier, living out of that kind of pressure or that kind of internal dynamic is pretty toxic for most of us.
Clay Collins:I think so. It was less about me doing me, it was more me proving to myself that I could thrive within a traditional system. Arguably, on paper, I think I thrived, but internally, I was hating it.
Sherry Walling:You know the difference.
Clay Collins:I do.
Sherry Walling:How did you encounter technology? Like, how did you start with computers?
Clay Collins:Yeah. Great question. When I was pretty young, my parents had an Apple IIc, you know, they used it for the spreadsheet function when they had a business. And I just fell in love with it, even though I had to spend almost half my time swapping out floppy disks, and it was there that I learned a little Basic and started drawing shapes and playing around with conditional logic and stuff like that. But I just loved it. I felt so empowered. I felt so many of the things that felt laborious to me when I was trying to operate the physical world, when I was playing with atoms instead of bits like all those things just sort of melted away in front of the computer; it was easy to sort of imagine things and rewrite and it just felt like it was this space that was really accepting of how my brain worked and that was really awesome.
 So it was pretty young, I’d say seven, eight, nine, we had a computer that was an Apple 2C, and then eventually we got a 386 that ran like MS DOS 6.2, and Windows or 6.1 or something like that, and then Windows 3.2 and a friend of mine at school started programming things with visual basic and like that looked super fun, so I ripped off his copy of visual basic and started writing things in visual basic and that graduated to something similar to a visual basic called Delphi, which is based on Pascal, which is a kind of an earlier programming language and then that turned into a database programming and web stuff and I paid for part of college by working full time at a research institution writing web apps for querying databases. Yeah, it just kind of escalated from there but I’ve always been with technology; it’s always felt really empowering, up into the point where I got a smartphone and then it really feels like a burden and I hate it.
Sherry Walling:You’ve crossed over to the other side.
Clay Collins:Uh, God, yeah. I have this kitchen safe that I lock up my smartphone in; I can just put it in for like, I can set it for five hours and just drop it in there and it won’t allow me to get to it and that’s awesome, but I digress.
Sherry Walling:Or maybe not, I mean it’s an interesting problem in which technology is now taken over so that we have to lock up our weapons and our phones. Those are the dangerous things in the house.
Clay Collins:Oh my gosh, yeah, absolutely.
Sherry Walling:Do you regularly take space from technology?
Clay Collins:I do, not as much as I’d like. I’d say that this safe that I have that’s really designed to keep people on diets from eating cookies or whatever, you can set a timer. That has really been the biggest help. I used to go backpacking by myself and it was kind of forced because they wouldn’t have cell towers in the places I was camping and now the places that I go camping have cell access so I have to lug up my kitchen safe up there and I’ll lock it when I go on these kind of solo camping trips by myself. I’d say a couple times a week I’ll go for 8-12 hours without a cellphone and then maybe once or twice a year I’ll go for a couple of days, but it’s not as much time as I’d like and that’s something that I’d like to be more deliberate about now that I no longer have a day job.
Sherry Walling:What feels different? What happens in you when the phone is in the safe?
Clay Collins:I think there’s a certain space, or there’s a certain cognitive door that gets shut. Even when the phone is available, you know, I’ve read studies that essentially say that if you’re having dinner, just the presence of that phone on the dinner table changes the way people interact with each other. I think when the phone is in the safe, I don’t have an option to look up something that just happened to float into my ADD brain. I can’t check messages; that’s not even an option. And I think I start to just go more internal. I think I start being a little more at peace; I’m not always if a message has come in or a voxer has come in or if someone’s tweeted something. You know back in the day, when we were first starting, I’d be worried about the servers going down or something crazy like that. Those things, I think, come into my head and they just leave a lot quicker because I know that they’re just not, it’s just not an option to explore those things. That is just such a gift. I think it feels like freedom, it allows me to be more present.
Sherry Walling:Empowering to take some of your mind back.
Clay Collins:Exactly.
Sherry Walling:I mean you described so articulately what it felt like at first to begin interacting with technology and almost like it was a native language that you were learning as a young child. I think a lot of young, maybe boys in particular, but youngsters who have brains that work really fast or work somewhat circuitously do super well with technology because the tool can keep up with the nature and function of their minds versus sort of a very linear human interaction or something that is not as flexible and not as fast. I guess I’m wondering if technology felt like a native language to you, when you were first encountering it.
Clay Collins:It did. I think part of having ADD is maybe having less working memory and so to have this place where you can sort of output your thoughts that’s pretty stable while your mind is racing in 100 different directions, you can always be anchored by what’s on the screen or the last five things you’ve written, you can write, you can rewrite and that’s a stable while what’s in your brain can be ephemeral so I think you can sort of flex the logic muscle a lot more because of the stability of what’s on the screen. So that’s really what it was like for me and I think it really helped me become a writer.
 I think growing up, especially early on, I would not have anticipated that I would, or I don’t think anyone, I was too young to contemplate such things, but I don’t think anyone who knew the early me would have anticipated that I would have been into technology. I really just like sitting out into a field, staring into the sky, being alone with my thoughts and just thinking about things, and to this day I think I’m probably-I’m a huge introvert even though I enjoy public speaking and writing a lot and interacting with people. My favorite thing to do is just kind of sit in a room by myself and just kind of think about stuff so I don’t know that that necessarily screams technology. I think that’s probably one of the things that, in retrospect, might have been surprising.
 I think another one is just how much I enjoy story telling and that wasn’t something that really came to light until I started blogging. I never wanted to be a writer growing up or thought that that was a strong suit; in fact, I think I was really bad at it because almost all of the writing I did in classrooms was with kinda the blue notebook and it was about what you were able to pull off under a lot of constraints, and a timed test, and I had a crappy handwriting and I was left handed and it would take so much time to actually physically write what I wanted to write, much less revised or get the spelling right that I just always assumed that I was a really crappy writer and speaker because of those things. But that ended up not being the case, and I think that’s another thing I owe to technology.
Sherry Walling:The ability to hold your thoughts together and tell a story in a way that surprised you.
Clay Collins:Absolutely, yeah.
Sherry Walling:So we’re talking on a Thursday and I’m guessing that you don’t really have to go to work on Monday. What are you going to do?
Clay Collins:Yeah so on Monday, I heard maybe you might come, but actually Monday is my last official day as an employee and then we’re having a party here at my place, or at my man cave.
Sherry Walling:Yes, the man cave, the party place.
Clay Collins:Yeah, the party place.
 So, we’re having a party here and that’s my send off, so I think Tuesday morning, I’m probably gonna sleep in and I’m gonna wake up, and instead of maybe racing off to work, I think I’m gonna feed my kids or my wife and I will go out to breakfast and probably do that in the morning and then when the nanny comes I think I’m probably gonna read some technical white papers, play around with crypto currencies, and I have some books on economics I want to start reading. I bought this domain name that I’ve had in my back pocket for a long time; it’s just nomics.com, like instead of economics it’s just nomics.com and so I think I might just start blogging for fun. Who knows where this will take me; it might not take me anywhere, it might just be five essays and that’s it, but I think it’ll be nice just to have this space to fill.
 One of the things I used to advise people, especially this kind of generation that’s kinda growing up right now, like 20 year olds that maybe read the 4 hour work week, I called them like- There’s this generation of people I call the lost boys of lifestyle deign, and maybe they read the 4 hour work week and they’re goal is to run a business from a laptop while going around the world in a balloon or whatever and they get kind of distracted by that dream and they end up just being really lost during that phase because I think society has failed them and education has failed them and a number of things have failed them during that phase.
 I often advise them to just sit in a chair with no technology around you until you have your first impulse, and that first impulse might be to just go to the bathroom, but it’s something you have to do, so go to the bathroom, come back, and you’re next impulse might be to eat or something like that, but you’re next impulse might be to write down something that just floated into your mind that feels really compelling but make sure whatever you do, it’s super compelling to you and it’s something you can’t not do. I think that’s sort of the bar, it’s got to be something you can’t not do and I think our jobs, this is a pretty privileged thing to say, but I have a ton of privilege so I guess I can just say it, but our jobs, when we do have free time and space to create, is less about the actual thing we’re creating and more about clearing out everything that we can’t not do; and waiting for the good stuff to fill in because in my experience, I mean this has been my personal experience, as long as we clear away the crap, the awesome stuff just flows in because nature pours a vacuum and if you set your standards high for what can fill that vacuum, you usually end up with something pretty awesome.
Sherry Walling:It sounds like you’re entering a blank canvas. You have some interests you have with a domain name that you’ve held on to. It sounds like you have some things you want to read about and research and do some writing about, but really there’s some open space that you haven’t had in a long time.
Clay Collins:Yeah, and I’m super psyched about it. I haven’t had this kind of open space for over five years and this open space, in a lot of ways, is what I live for. It’s the big gift homeschooling gave me; it’s the big gift that being self directed gave me and I think it’s much, in my experience with Lead Pages has been, one of the best experiences of my life; I wouldn’t trade it for the world; I wouldn’t trade it for anything, but in a lot of ways it’s like being strapped to rocket ship and growth has its demands, and skill has its demands and for those demands to largely fall away is just gonna be a huge gift so I don’t have, you know, folks have been asking me “What’s the next thing you’re gonna do?” And it’s like, I don’t know, and that’s what I’m savoring.
Sherry Walling:I love that answer. I love that answer, especially how well it connects to where you came from and who you are and your heart of hearts. The open space, the creativity, the tinkering, the time. I’m excited to see what happens with that, not what you do, what you produce, but just how it feels.
Clay Collins:Yeah, I am as well. One thing that I’m doing, this would have never happened even a month ago or two months ago, much less a year or two ago … I saw, there’s this venture capitalist, Fred Wilson and he posted to his blog that some folks he’s affiliated with were leading this free trip to a place called Zug in Switzerland, which is kind of the crypto currency capitol of the world right now, it’s where the Ethereum Foundation is based and the Tezos Foundation and a bunch of other really cool foundations and it’s a banking center in its own right and they were planning this 3 day trip out there, both between there and Zurich and you can meet with leaders of these different foundations and you had to apply; you had a group of 25 coming from all over the world and the first thing I thought when I saw that was “This would be so cool to go to. I wonder if I’ll get accepted.” The second thing I though was “Oh wait, I can’t do that. There’s no way I can justify that.” And the third thing I thought was “Oh wait, I’m not gonna have a job pay.”
Sherry Walling:Retirement’s sounding great.
Clay Collins:I know. So I’m going to do that and that should be fun and it’s just uncharted territory.
Sherry Walling:So cool, Clay, so cool. Well, I don’t want to take more of your time today. I know this is sort of the day that this announcement was made public, so I’m sure there’s lots of conversations that you’re part of, but I appreciate you taking the time to talk with me and talk about this story and the stories from the past and, as I’ve said, I’m excited to hopefully get to check in with you here and there over dinner and just hear how things are going as you enter this next phase.
Clay Collins:I would absolutely love to stay in touch about this and any number of other things, so thank you for having me on Zen Founder.