Andy Sparks on Writing, Entrepreneurship, Success & Life As A Lake

[01:34] Paul: Just wanted to jump on before the episode and give a quick update. I've been spending the last month working on a new course. It's called Reinvent, and it's a combination of contemplation of what is the role of work in our lives, And how do you actually create and move forward given the new state of the world and ways of working? I'm super pumped to be building it. I'll include a couple links where you can follow along some of the content creation I've been doing. I've been doing it in public and a link if you're interested in signing up.

Here's my conversation with Andy Sparks. Hope you enjoy it.

[02:16] Andy Sparks: Today I'm having a conversation with Andy Sparks.

[02:21] Paul: He is the co-founder and CEO of Holloway, a publishing and technology company that creates comprehensive practical guides, research written and refined by experts. He is motivated to give people tools to turn their brains on instead of off. Prior to Holloway, he co-founded MatterMark, a data platform for venture capital firms. We'll dive into his story and some of his views and perspectives from his journey and on work. Welcome to the podcast, Andy.

[02:59] Andy Sparks: Awesome. Thanks for having me.

[03:00] Paul: So I want to start in college. You ended up starting a brewery at the age of 19, which you later found out was illegal. I'd love to hear more about that, but first just want to start with where did this entrepreneur drive come from?

[03:19] Andy Sparks: Yeah, that's a great question. I love the setup too. I love that that's like some kind of random decision I decided to make when I was 19 and I get to tell a fun story now. I think it started with probably my dad. Um, my dad grew up pretty poor and he— when I think there was like this day that I came home from school and I wanted to buy a pair of copper wash jeans. From Abercrombie Fitch.

My dad used to work as a welder where his jeans would get ruined with rust dust. And so when I wanted to buy a pair of jeans that were purposefully dirty and expensive, he was just like, put his foot down. He's like, "No, I'm not buying this for you. But if you want to buy these, if you want to buy anything beyond just basic stuff, then I'll come up with a list of tasks." I can pay you, or you can go do stuff in the neighborhood. And so I actually started a little lawn mowing company when I was a kid with my dad's lawn mower. It had an aggressive name for it.

I was so naive. I went around the neighborhood and hung up flyers on everyone's doors that said, All American Mow and Blow. Wow. All we had was American stationery, like American flag stationery. I figured, why not call it All American? I was like 12.

My mom had to explain to me what that meant after that, after she came in the door crying laughing.

[04:48] Paul: Oh, wow. Wow. So you had no idea what you had written.

[04:51] Andy Sparks: No, I didn't. I was offering $20 mow and a $5 blow to everyone in the neighborhood.

[04:57] Paul: Oh my God. That is pretty good. Did you get customers though?

[05:02] Andy Sparks: Yeah, I did get customers. I think there are a few neighbors thought it was so hilarious. Uh, but that was my introduction, I'd say, to just what it was like to actually earn kind of your own living. I was also privileged enough to grow up in a family where my dad could give me a list of tasks and pay me money to do them. That was pretty cool. But it was, it was, I guess, that first taste of agency and freedom for me as a kid that if there's something that I wanted to do, this was a pathway towards figuring out how to do that.

Then when I got to college, I just— that's a complicated path, but a friend of mine just came up to me at the tailgate and was like, "Hey, have you ever— what do you know about the microbrewing or microbrewed beer?" This was 2008. I was thinking I was probably holding a Bud Light in my hand or something like that. My dad had homebrewed beer a little bit growing up and it was enough to get pique my interest, and we both started doing a bunch of research, and it was just frankly more interesting than anything I was studying in school at the time. It was like a very applied learning project where, hey, start— what's starting a microbrewery? What does that take? And it took me down all these different roads from market research to branding and opening up Photoshop and designing beer labels and trying to understand some of the chemistry.

And it was, it was really interesting as I look back, just how you took, or how it took me as a kid that was trying everything that I could to stay out of class at the time, and suddenly I found this thing that I loved learning about and I was willing to do work to, to dig into. So it was a really fun experience. My favorite part was the market research though, which was going and buying a bunch of beer from the corner store and sampling all the different beers to find out what we wanted to do.

[06:51] Paul: What was the moment like when you found out you were illegally running a brewery?

[06:57] Andy Sparks: Well, I think we always knew.

[06:58] Paul: You just didn't want to face the facts.

[07:02] Andy Sparks: Yeah. I mean, it was like, is this technically illegal? I don't know. Because it wasn't, let's go start a microbrewery. I mean, it was, hey, let's homebrew beer for a while and find out if we can do this, see if it's any good. I think this is probably the origin story of almost every microbrewery.

But it was just two of us homebrewing beer every weekend for a long time. And every time we'd go buy homebrewing supplies, the woman at the homebrewing store, you could tell she was— you could tell she knew that it wasn't illegal for her to sell us homebrewing supplies, but it was kind of like ethically questionable. But eventually we got into, hey, let's start a business with this thing. And we wrote a business plan and we incorporated. I remember buying a book from Barnes Noble on What's the difference between an LLC and a corporation and S corporation, all these different types of business entities. And yeah, we just kind of incorporated blindly.

That's just what you needed to do, right? And we figured if we wanted to raise money from investors or something like that, that we'd need an entity to take money. And then at some point along the way, I came across, you know, reading the alcohol laws that you can't own more than 50% of a company that makes most of their money from alcohol in the state of Ohio until you're 21.

[08:16] Paul: Sounds like there's some wiggle room there they leave for, uh, some opportunity. Um, so what was that like being in college? You're doing something entrepreneur, uh, you're embracing kind of your inner entrepreneur, you're learning things, and then you're going back to the classroom. How are you thinking about like your path, your careers, like what's next at that point?

[08:43] Andy Sparks: That's a great question. I took this class in college eventually called, uh, it was something really lame like Business Management 390. Ohio State was offering a new minor path called a minor in entrepreneurship, and they had a few classes, and this one was taught by a guy named Artie Isaac, who was a Former— he had just sold, I think it was like a creative agency that he owned called Young Isaac, and he'd been teaching at the art school at Columbus College of Art and Design in Columbus, and he started also teaching a business class. He taught art students how to make money off of their art, and then he realized that he needed to teach business students how to create art.

[09:28] Paul: I like that.

[09:29] Andy Sparks: That was the class that I took. And through that class, I got introduced to a pretty small, maybe 30 or 40 person community of students at Ohio State that were all interested in starting businesses of some kind. And they were kind of an antidote to the MBA type students, you know, like everyone wearing a suit and wanting to talk about how they wanted to go work for a giant company. The students in this club, it was called the Business Builders Club, which we sometimes joked around and called it a drinking club with a business problem. They were kind of a ragtag group of people who were just like, they didn't want to go work for a big company, but they were interested in being independent. And I loved that group of people.

And all of us ended up going on to really learn together. Two of the guys now work at a venture capital firm in Columbus. Another one has his own venture capital studio in Seattle and has started a few things. And quite a few people have gone on to work at startups and do pretty well for themselves. So it was cool to have that community. Arty's class was great because he encouraged all of us to just really think from first principles about what creativity is.

Forget about starting a business. He wasn't an academic in a normal sense. He was just really, really great at getting us to turn our brains on. And one of the ways he did that was he encouraged everyone to write every day for the class. Part of our textbook was this book called The Artist's Way.

[10:58] Paul: Oh wow.

[10:59] Andy Sparks: Some people may be familiar with it. And that was like part of the course curriculum, which I think was just really strange for a business class. But it was easily my favorite class that I ever had. But it was an absolute anomaly when it comes to classes. I remember as part of this business club, we went to a TEDx conference in Washington, D.C. that Google was putting on.

And I told my history professor that I needed to go to this conference as part of this club, and it was, you know, we're going to learn all this stuff about business. And she told me that, you know, I would get a, like, grade level, a grade letter lower in the class if I skipped class that week because there's nothing more important than my studies and I shouldn't be going and traveling and basically learning something else. And I just couldn't believe it that You know, here I was saying, hey, look, I'm still gonna do all the work. I just need to miss class because I'm gonna go, right, try to learn something new on my own and be a self-directed learner. And it just showed that, that, that was what I encountered a lot more. And maybe it's unique to Ohio State.

I doubt that it is, but oftentimes I found that the university essentially is a factory, right? That they're just trying to produce a certain level of mediocrity in a student that society can be basically prepared for. You know, what's a standardized product that a university can create?

[12:28] Paul: And I think the cool thing about universities is I went to a big school too. I went to the University of Connecticut, and they're big enough that there's enough of those weird professors, right, that want to really change people's life. I encountered a couple of those too, and I always wonder like, what if I didn't meet the, that professor, right? That really implanted a few different ideas in my brain. Are there like one or two things that stick in your head from your experience with that professor?

[13:06] Andy Sparks: Yeah, absolutely. Um, oh man. There's not just one or two, there's like 50. Yeah. He had us read Seth Godin's Lynchpin, or did he have us read that or did someone I met? First of all, I met 4 of my best friends in that class.

[13:22] Paul: It sounds like I'd really get along with this guy.

[13:26] Andy Sparks: Yeah, totally. He's super rad. He had us read some things from Buddhism. You know, one day the entire class for almost 2 hours was just, the prompt was, what is creativity? And everyone had to go around and argue, and it turns out no one had any idea what creativity was. Some people thought it was just bright colors of paint.

Yeah, some people thought it was, you know, it's— and it's— and you— and that was an eye-opening class to me though, because I had not really thought much up until that point about how we all use these words. We like walk around every day and we all use these words like we all have a shared understanding of what they mean. In reality, that's like We did not. He was great, and I asked him about this business that I was starting, this microbrewery, which he thought was hilarious, and he gave me practical advice and gave me the time of the day. My favorite thing that he said in the class was, "What you guys don't realize is that I work for you. That every day, each of you or your parents or the bank is paying thousands of dollars for you to be at this university, and you're my customer.

I'm not yours. Like, each of you is an adult. You're over 18. You're paying money for a product. And so if you're not getting something that you want out of me, then you should be raising hell about it. And that was so inspiring to hear as a 19-year-old, because no one talks to you that way at a university.

You know, most people at a university are telling you that you need to sit down and shut up and listen do it this way or that way. And he was basically saying, you guys should go make some trouble. And I loved that.

[15:04] Paul: Go make a ruckus, as Seth Godin would say.

[15:07] Andy Sparks: Yeah.

[15:09] Paul: I resonated with some of your writing about your early career experiences. I, similarly to an experience you had, had someone tell me you didn't go to the right schools when I was trying to break into strategy consulting. I think as a young guy with an ego, that really kind of pissed me off and made me super competitive. I really just wanted to prove people wrong. And you've written about you having a complicated relationship with status and confidence as well. Maybe you can talk to me about a mug you got from Harvard Business School.

[15:49] Andy Sparks: Yeah. My roommates and I were just talking about that mug yesterday. Let's see, my parents both went to the University of Iowa. When I was applying for schools, I never really got any encouragement to apply to, you know, a big Ivy League school or anything. I don't think my family valued that, and I also don't think that they thought that I was going to get into one of those schools. You know, I kind of like coasted through high school.

I loved going to Ohio State. My dad said, just, I don't care where you go, just go somewhere big and cheap. And in retrospect, so thankful that he gave me that advice.

[16:21] Paul: That was my strategy too.

[16:23] Andy Sparks: But then when I got to San Francisco, I had just shut down my first company, I guess my second company if you count the brewery. And I was interviewing with a few people or even informally interviewing. And I was talking to a couple of venture capital firms and pretty good ones. I don't know if it would have seriously led to a job offer or anything like that, but I remember speaking with one person in particular who I'll never forget. That he, when I shared with him that I was speaking with these two venture firms, he was like, wow, I'm surprised they're even talking to you with a background like you have. And I still to this day hold a grudge against this person, um, just because it was such an elitist, petty comment to make about, you know, that he— the guy didn't know anything about me.

He just knew that I hadn't gone to one of these big fancy person schools and Anyway, so the mug. So I started Mattermark and we had a Harvard business case about that company and we got our picture taken there. And my grandmother who lives in Jackson, Mississippi, she wrote me this letter basically saying she couldn't believe that someone from her family was even allowed in the building at Harvard. And I don't know, it was just such a precious moment for my grandmother. And then they sent me a mug as thank you. And then that mug, every day that I have it is kind of like this this egotistical reminder that, hey, even though I didn't go to Harvard, they invited me to come talk there.

[17:51] Paul: That's fascinating. We, we have a weirdly similar path in that I also took some mugs from like places I worked and grad school and kind of had all my mugs. I ended up getting rid of them last year, half in a moment of just why do I care so much and half in a moment of minimalism. But also experienced a similar thing, have this complicated relationship with status. I ended up going to MIT for grad school. And I think the coolest thing about that was neither of my parents went to college.

So them being able to just be like, yeah, my son went to MIT because so many people have given them crap. For not going to college, right? It's such a scene as like, oh, you didn't go to college. Um, and it wasn't like that 40 years ago, but it is now. And it was just kind of this, um, I guess, F you. But yeah, definitely have a complicated relationship with this status and confidence as well.

[19:03] Andy Sparks: Yeah, it's amazing how different it is from generation to generation. It wasn't until I was 26 that I found out my grandpa didn't even graduate college. And my grandmother was the only daughter in her family, I believe. And her parents paid for everyone to go to college except for her because she was a woman. And even though she's, you know, I think she's smarter than my grandfather is.

[19:30] Paul: Even still, I think 25% of Americans now have a college degree.

[19:35] Andy Sparks: It's a crazy low number. And less than— I think I saw some number, and it might be wrong, actually. I have like 50% chance this is wrong, but it's like less than 10% or less than 5% of human beings. I was reading a book maybe a year or two ago about different Greek schools of thought and going all the way back to the origin of academia and where does that word come from, right? And Plato's Academy. And Plato's particular brand of philosophy was very disconnected from practice.

It was all theory. And so what I took from that though is that there's kind of this 2,000-year-long running joke about academics and that academics have no connection to practice and reality. And, you know, all these business people and very hands-on people will make jokes at the expense of academics. And it just seems to me that, you know, that's the intention of what Plato's Academy was to be. It was to be disconnected from practice. It was to be theoretical.

And I think that that's where academia and our current education system can fail a lot. And where what you're saying, like, I have friends that didn't go to college too, and they can— they're more, most often, brilliant people. They just didn't get the same level of theory So I think that the university has gone too far oftentimes into that theory and way too far away from the practice.

[21:04] Paul: I think it jumps out for me. I read a lot about work, and I probably don't get the best ideas about work from academics. It's increasingly like philosophers, poets, literature, and especially people like in the, on the front line. A lot of times academics are looking at things, uh, and things they can measure, right? It has to be put on a spreadsheet and they're often missing very obvious but impossible to measure things like dignity, right? Like pride, competence, all these things.

Um, and I read a lot of research around work and it's like, okay, this makes sense, but you're not factoring in that this person doesn't have dignity, right? It's around like, you have terms like job crafting. It's like if people just crafted their jobs, it's like, okay, this is great, except what if the person isn't even showing up with like the dignity or honor of being proud of what they do?

[22:11] Andy Sparks: Especially my girlfriend and I were just talking yesterday about the education system and ever since No Child Left Behind, at least in the United States, education is so exclusively about what can you standardize. We were talking about how do you standardize teaching value systems? How do you standardize wisdom? How do you standardize things like that, exactly what you're saying? You can't. I don't know, even if you can, I don't think I'd want to.

And I think that that's where we've got problems. One of my favorite things, I actually go back and I taught classes with my dad at the University of Iowa and sometimes at Ohio State as well. And what I love to talk to students about is I'm like, have you ever thought about coming up with your own system of values? Take out your notes right now or your computer, whatever, and write down 10 things that you think you value. Here's a few examples: humor, risk, family. Just come up with a list of those things and then start to just think about why you value those and what you don't.

And the next time that you get into an argument with someone, ask yourself, what do you value that you're arguing about that maybe the other person doesn't value the way that you do? And that's something that, like, when we were coming up with our company values at Mattermark when I was like 23 or 24, I realized I didn't know what I valued, and so I sat down and tried that myself, and that was one of the most rewarding experiences. But you're totally right, like, a lot of the most interesting things don't come from academics. I think that you, you briefly brought up that writers and poets and literature, that those people, those authors and writers, have a lot of wisdom that doesn't get taught. Because it seems like artsy or something like that. Or I'm not even really sure why people don't think there's value in it.

But I talk a lot with friends about how often they read nonfiction, and I try to encourage everyone to read more fiction because nonfiction seems like, oh, it's a direct path to knowledge, right? And in fiction, there's so much good stuff.

[24:18] Paul: Yeah, I actually wrote something about this. I was saying, I think there's a lot of people that, the people that love nonfiction, right? I was, I am still one of these people, but there's almost a path. I was talking with a philosopher about this and saying there's almost like a step where you need to like read this nonfiction book that's like a pathway to like a little more nuance and perspective on the world.

[24:45] Andy Sparks: Uh, yeah.

[24:46] Paul: So I created these like 10 levels you need to like Escape the Corporate World, and it's like a slow progression. It's— but yeah, I think people are like, oh, read more literature, right?

[24:59] Andy Sparks: But do you have that posted somewhere?

[25:02] Paul: Yeah, I can share, share that with you. But as somebody that, like, my gospel were like these behavioral economic books, but I didn't have a sense of how the world worked yet. And it, it, I almost needed to read all these different, uh, books to get me to that. Whereas now I'm much more inspired by those deeper ideas. Um, I'd love to shift to, you wrote about doing it for the money and how you got that out of your system. Uh, I think we all, it's impossible to fully get that out of your system, right?

But I think a lot of people have this first chapter when they're going after traditional metrics. And that makes perfect sense as we're jumping into this business world, the real world, right? But how did you make doing it for the money maybe less important?

[26:02] Andy Sparks: Yeah. Money is something that— my dad is a huge figure in my life, and when I was, I don't know, 15 or 16, he and I would talk a lot. My parents were really open about alcohol. My dad would be like, I'd rather that you'd learn how to drink with me than go drink at a party. This is relevant, I promise. And so, you know, we, we had a hot tub at our house and my dad and I would just sit and have a beer in the hot tub starting when I was like 15 or 16.

And we would talk about life. It was really cool. And I feel really lucky that he did this with me. And one of the things that he told me was that he didn't have a plan in his life other than make more money than his dad did. And he accomplished that plan when he was 30. Then he had this crisis of like, "Well, what the hell do I do now?

I didn't plan. I didn't think this would happen until much later in my life." Then he just kind of wandered around for a while trying to figure out what it was that he was trying to do. He really tried to encourage me a lot to find something that did make money, find a job that made money, find something that I enjoyed, which is a bit of a paradox that I both love him and hate him for giving me this quest.

[27:31] Paul: Yeah, it's high stakes to find something you enjoy, right? It's much easier just to find something that makes a lot of money.

[27:40] Andy Sparks: So I think that a lot of this quest comes from my dad, but also I think that as I've gotten older, I've realized just how much— my parents hate the word privilege, but I think that that's exactly what it is, is that I I've had a family that I was able to graduate college without any student loan debt. My dad bought me a MacBook Pro, which is like buying a carpenter a set of tools, right?

[28:05] Paul: Right.

[28:06] Andy Sparks: And so I didn't at least need to make money to like— I could at least pay rent. I was able to— and I always worked in college at internships and stuff like that. And so when I graduated college, I had a job at a small software company. And so I didn't have to worry about paying rent, which I think is just an enormous way to kind of start a career, at least on like second base or something like that. I wasn't making an enormous amount of money by any means, but I think my first job I was making like $42,000 a year, but at least that wasn't I didn't have to worry about, am I going to be on the street or something? So then my first startup after the brewery, my first software company, I thought, well, this is going to be like a get-rich-quick thing.

It's not how I would have phrased it at the time, but I saw dollar signs and being able to turn what we were building into something that could make us a lot of money really fast. And I realized pretty quickly that made me feel kind of sick to my stomach. that there were other things that I thought about. I'm way too much of a thinker and borderline academic to go work on something where I can see effects on the world that don't sit well with me. And then there was this dinner that I went to also with my dad. I was studying history in college for a long time.

He took me to Ruth's Chris Steakhouse, which was by far the best meal I'd ever had in my life by a long shot. And we had dinner, and at the end of the dinner, he was like, do you know why I brought you here? And I was like, I don't know, because you love me or something, right? And he's like, no, actually, I just wanted to let you know that if you decide that you want to be— you want to study history for the rest of your life, you want to be a PhD, go get your PhD, you probably won't have this like very often. Which I don't know if that's right or not, and maybe my dad was kind of sadistic, But he was like, "I want you to make the decision with your eyes open that if you want to do something else where you could go out to dinner and have good meals, you should just make that choice with your eyes wide open." So anyway, long-winded way of answering your question.

I think that there's still some part of me that I want to find I want my work to be fulfilling. I feel like my work with Holloway is deeply fulfilling. I love living in San Francisco, but San Francisco is just an absolute crazy city in terms of how expensive it is. And so if you want to have a family and kids in San Francisco, you basically have to figure out a way to get rich just to live here.

[30:57] Paul: Right.

[30:57] Andy Sparks: Which I hate. So I have a very complicated relationship still with what, you know, I don't need to drive a— I don't even need to own a car. I don't need to have a huge house, but I would love to live here. And so, um, anyway, I don't know if I answered your question at all.

[31:18] Paul: No, I think it's something, uh, it sounds like you're still grappling with it. It's something I definitely am still grappling with as well. And, um, It's, I think it's a challenge for many people.

[31:32] Andy Sparks: Yeah. I think the big difference maybe is that I know some people who are just, where making money is a singular focus for them.

[31:40] Paul: Right. And I think there is that chapter in people's life, right? I, I, it sounds like you had something like of a benchmark, right? You want to find at least like some success, right? I think I had a similar thing. It was like, once I make this amount of money, I'll be a success.

Or maybe this resonates more with what your dad was trying to achieve. Then I did that and I was like, well, I'm good now. And now I'm trying to like reinvent again. I make much less than I used to, but I feel like there's a much deeper connection to what I'm doing and finding much more joy in it.

[32:20] Andy Sparks: So yeah, I think I also came across some cool ideas in between my, uh, this company Launchgram that I started and Mattermark, where I don't know, I went down some internet rabbit hole and started listening to Alan Watts lectures. And, and I love— he's got one lecture that's basically like, look, if you spend your time getting really good at something, just become one of the best people in the world at something, the money will follow. And the more and more that I read about your 20s, it was just like, if you just invest your time— I read Mastery by Robert Greene and all these books about learning and career development and life and fulfillment, and it was like, so much of being young is just absorb as much as you can. Learn as much as you can.

And so I spent all of my 20s basically optimizing for how can I just absorb and learn as much as possible, um, and then figure it out what happens in my 30s. And now I'm 30 and I'm like, okay, am I still, am I still optimizing for that? Or is it like, is it time to switch gears into something else? Like, I'm— there's everyone starting to have families and life seems to be getting a little bit more serious. I don't know.

[33:35] Paul: Yeah, I don't know if that ever ends, right? I think the learner always wants to learn, but, um, it sounds like you were able to grasp a deeper definition of learning, maybe from that, um, teacher in college. Uh, but I think a lot of people misunderstand learning, right? Learning isn't performing on tests. It's kind of stepping into the unknown and keep showing up. So maybe this is a good transition to start talking about writing.

Um, and I've found writing to be one of the most challenging things and don't think I'll ever be like fully satisfied or like ever done with learning how to become better. Um, but I've found that many people have a feedback mechanism, which at least at the beginning keeps them going. For me, it was meeting people through sharing ideas and then them giving me more ideas. Did you have something like that when you first started, or was it just the Artist's Way approach that helped you start writing and keep writing?

[34:44] Andy Sparks: I started writing because I started journaling even before I found the Artist's Way. I think I was in high school or something, and I would write by hand on paper. Just to kind of get my thoughts out. I've always described sometimes I get this emotional state where I just feel kind of emotionally pregnant, like, like I just— something's going on and I don't know what it is. And I think from when I was about 16 or 17, I started developing this habit of just writing to think. And probably from 16 to 19, I maybe did it, I don't know, 10 times a year or something.

And then I started Writing with the Artist's Way in Artie's class, where we wrote every day 3 pages stream of consciousness first thing in the morning for 3 months. And then you go back and look at the writing, and looking at the writing is cool, but it's more just noticing the patterns as you write, and you realize you're writing the same things over and over and over again, which brings in— it's almost like a sort of meditation where you realize that you're just running on these same vicious loops in your head as opposed to just wanting to get past those things because you don't want to have to write about them anymore.

And so that was where I really started to enjoy writing and then develop this habit a lot more of just reflection through writing, that whenever I was struggling with something hard, I would sit down and I would write about it, and I would just write until I felt better. And sometimes I would just write and I wouldn't feel better, but I would just, you know, want to fall asleep. But almost all of the major crises or pivotal moments in my life have been precipitated by a long period of writing. And I actually start to wonder now when I haven't sat down and done that for a while, I kind of have this looming sense of dread knowing that there's something I'm not dealing with. Like, I know that if I sit down at the computer and start writing, I'm gonna have to face that thing. And so I'll just refuse to write for 3 or 4 months at a time in terms of at least personal reflection.

So that was how I wrote for a long time. I started blogging when I was shutting down my company Launchgram, and that was a really rewarding experience because a lot of people— I think it was the first time that someone told me you're a really good writer, which feels great to hear. And I remember sharing one of my first drafts for that series, a blog post with Danielle, Danielle Morel, who became my co-founder of Mattermark. And she called me and she goes, this is one of the most boring pieces of writing I've ever read, Brett. She's like, this is all navel-gazing. If you want to write for other people, you need to write for other people.

And I think what I didn't realize at the time I'm not really writing it for other people. I'm just writing it for myself. And yeah, I'm curious what other people will say. So there's feedback from myself, from looking back at my own writing. There's feedback from someone else like Danielle reading your writing and giving you feedback. Um, and then there's kind of another phase of writing for me just came through honing that skill through Mattermark.

I mean, I just wrote and wrote and wrote when I needed to figure things out. And then when I left, that was figuring out what I wanted to do next. I just sat in front of a computer and just wrote to myself for a month or two, basically. That was so helpful. And eventually went on to start Holloway, which is all about writing, which little did I know that I would be embarking on a journey to write a 340-page book And so I'd say there's a whole new phase of writing, which was writing 340 pages inside of about a year, year and a half, and working with an editor, like a professional editor. And Rachel Jeppsen is on our team.

And I feel like that's just been an entirely new phase of writing for me. And that's where I've fallen in love with writing. And I now very much consider myself a writer. I didn't quite realize what it would be like to work with an editor like that. Someone who knows who— who really— I mean, Rachel knows who I am, and I think she knows what I'm trying to get across a lot of the time. And she's really encouraging.

She's like a teacher. She's got a great bedside manner. And so I always say, in terms of the way that she encourages me to be a writer versus oftentimes some people, when you share your writing They're, they're helping you by being critical. But what Rachel's so good at is being critical. I mean, every time that I give her a writing, she cuts more than a third of it. Like, yeah, she's pretty brutal.

But then somehow I leave, I leave that experience of being edited, having learned a lot and then also feeling like, okay, and everything's better now. I feel better. I don't feel like someone just shit all over my work. Even though that's basically what she did.

[39:44] Paul: What's one thing you've taken away from working with her? Or what is that voice of hers maybe in your head as you're writing that might have helped you improve?

[40:02] Andy Sparks: You know, now that I've gotten to know Rachel better, I'm sure that she says this to quite a few people. But there was a moment I remember when we were in New York City, we were walking and I said something. I wasn't writing, but I said something and she turned to me and she goes, "Yeah, I knew you were a writer." And I don't even remember what I said, but it was just this like, here's a person whose writing I respect and who I respect as a— I respect her as a writer and a person who understands words and the philosophy and the thought behind writing. And the validation in that moment for someone to say, yeah, no, you're a writer. Something about that, just the belief in yourself is really nice to have. So that's one thing I'd say.

And I would add a second thing, which is just the relationship that you build with somebody when you go back on 340 pages of text. Just by the nature of when you're trying to get this idea across and you're trying to share so much about something that's so specific, it's pretty cool. And I think had I done that with, you know, Josh, my co-founder, I think we probably would have had a really great relationship. Rachel happens to be just very, very, very good at what she does. And I would— and I told her at one point, I don't think I ever want to write anything without you now. I'm so used to— I send her every blog post, everything from the Holloway Guide that I wrote to copy on the website.

I'm almost afraid it's kind of a crutch now that I couldn't write on my own.

[41:39] Paul: Yeah, I definitely get the sense from reading your newsletter, Good Work, which I just love the writing. There is a powerful aspect of the essays. They seem deep but still short. Um, and that's something I'm still trying to figure out. I just keep end— oh, of course I'm this curious. Everyone else wants to read 10,000 words on this topic.

[42:08] Andy Sparks: Um, yep. We got shorter over time. They started out like essays and now I imposed a 4-paragraph, uh, rule. And then you get this section, and 4 paragraphs is extraordinarily hard.

[42:22] Paul: Well, 4 paragraphs is harder than 10 paragraphs, I think.

[42:26] Andy Sparks: Yeah. Oh yeah, shorter is harder. Always. One paragraph is hard. One sentence is.

[42:32] Paul: So let's talk about Holloway. You just published, as you said, a 340-page, uh, guide to venture capital, and You actually mentioned before you call it a book. That's what I wrote down here. I said it seems less of a guide than a better modern version of what a book could be.

[43:01] Andy Sparks: Yeah, we as a team struggle with the book versus guide versus what is it? Question a lot. So fundamentally, what we're building at Holloway is the technology to publish book-length content on the internet. And a lot of people say, well, there's plenty of books on the internet. I can buy a book on a Kindle or Amazon, or I can get a PDF ebook from all these different people that sell them. But books aren't published today on web pages.

So you can't go read chapter 6, section 19 of whether it's fiction or nonfiction on harrypotter.com/chamberofsecrets/chapter4. That doesn't exist. And so when you type something into Google about chapter 4 of Harry Potter Chamber of Secrets, you won't find that part of the book, even if it's just a preview. We really believe that there's just this massive error of omission on the internet that we just didn't put all the books on the internet. And so when you search for stuff in Google, you just find stuff that is available on a public webpage, which is content marketing and it's stuff that's written by magazines and newspapers like the New York Times or Medium, I consider a modern-day magazine. Wired, that stuff.

And books are the most professionally written, edited, proofread, fact-checked. That's like the most incredible knowledge source that people produce. And we never put them on web pages. And I don't know, to us, we just feel like, wait a second, we need to back up and we need to just do that.

[44:53] Paul: And I never thought about it. I've never seen it that way before. That is, uh, wow. This is kind of shocking for me.

[45:01] Andy Sparks: Right. When you see it, you're like, oh, wow. So that's what we're working on with Holloway, but then there's all these decisions you have to make. I mean, there's an entire swamp of decisions for— so since we're publishing online, is it even a book? I mean, it's not print. What is a book?

I've actually got a book over here about what is a book. There's not really consensus. So we tried to, at first, to get back to your original question, we tried in all of our positioning, we talked internally that we don't want to be compared to books. We said a book is what, $9 to $35, and each one of these things that we're producing costs a ton of money, and we want to have a business model where we can take the profit and reinvested in creating new knowledge and creating stable infrastructure that doesn't have advertising in order to share more knowledge. And not just knowledge, professionally written and edited and fact-checked and proofread knowledge.

[46:05] Paul: I think that's one of the hardest parts about reading online, right, is because you almost have to be your own librarian navigating what's what's written with the incentive to be SEO maximized versus what's written to actually share the deepest insights?

[46:27] Andy Sparks: We thought that we were— we tried to just say, "Let's stay away from books because we don't want to get compared to a $35 product." And fundamentally, everyone looks at what we're doing and they say it's a book. We're like, oh, it's a— I think Casey Newton at The Verge made fun of us when we launched our product because he's like some joke about calling it a guide in air quotes, right? Or not, just quotes. It's not a book, it's a guide. And it's like, no, okay, they're books and we just need to embrace the fact that we're publishing something that's a lot like a book. And the first car wasn't called a car, it was called a motor carriage.

And so I don't know, is what we're doing the next step in the evolution of the book? We'd like to think that in some ways that it is, but I think we've still got a lot of work to do before we can earn that.

[47:22] Paul: It seems like you're also trying to build almost an OS for reading long-form content online. I went through your VC guide and I thought it was very nicely laid out and I've read some other comments too. People were like, "Ah, this is how we're supposed to read online." So talk to me about how maybe you discovered some insights about how to make that experience better.

[47:50] Andy Sparks: Well, Josh and I both got together to start this company because on one hand, we just wanted to solve the problem of sharing knowledge online. But we also really connected over our mutual love for reading and a beautiful experience. We have all these books in the office that are these old books from 100 years ago or 50 years ago or 80 years ago where the typography is really well done. Typography has almost become kind of a joke, I think, because Steve Jobs popularized it. It's kind of like a pop design thing. But when you look at something that's just cleanly laid out, it's on a solid grid.

The typefaces are on a reasonable ratio to each other, and you pick beautiful typefaces. There's just something that fits. It just looks good. I mean, everyone knows I'm like totally blanking. Anyway, there's, there's all these great examples of just beautiful books that you can go get at a store, you know, that are print. But on digital, you just— Kindle is kind of just like all you can get, right?

And they have got a few typefaces, but it's just black, you know, white background, right, black words. And they basically just took paper. And there's something to a lo-fi reading experience because screens can be so distracting and sometimes you just want to sit and learn. But the people that really lead reading online are O'Reilly and Manning, and they don't do a great job. That's a— it's kind of a condemnation of the state of the best that we can do for book-length reading online is Kindle, O'Reilly, and Manning.

[49:48] Paul: Well, they're starting from a publishing paper-based business model, right? So it's completely different mindsets that they're— that they've grown up with.

[49:58] Andy Sparks: Right. So I'm not trying to take a cheap shot. We don't ever want to take cheap shots at people that are coming from an earnest place of trying to create a better way to share and publish knowledge. But I do think that it's worth calling out No one's just started from scratch on digital, right? So if we're going to take all of the tools that we have available to us in, at the time, 2017, and now 2019, almost 2020, and we wanted to publish book-length content for the web, how could we take advantage of as many of those things as possible? And, uh, you know, O'Reilly was started in the early 1990s, and they've done a lot of really great books and a lot of great content.

And Safari Books Online has got a lot to offer, but no one's just said, hey, why don't we just start from scratch here today? And what we wanted to do was just take a lot of the things that were great about old beautiful reference books, bring them to a screen, and then introduce new ideas. Like, one thing you can do on a screen that you could never do in a print book is when you come across a confusing definition of a term, you can just hover over it and get the definition of the term. And not just the dictionary.com definition, which dictionary.com is like the— it's like the McDonald's of dictionaries. Um, like, that's, that's even a whole thing that, you know, you can have there. There used to be much better dictionaries before dictionary.com.

But there's so many things you can do with a screen and digital with, with reference and long-form book-length stuff that we really should do.

[51:43] Paul: What are some of the next topics you're thinking about at Holloway?

[51:48] Andy Sparks: The next guide is on technical recruiting and hiring, which we hope will be just as helpful for a team at a huge company as it will be to a small company. So Engineers aren't just a Silicon Valley phenomenon. Now every company to some degree is now a technology and a software company, right? So we hope that that one will be really, really helpful and valuable to our audience. The next one that we're— we haven't 100% committed to it yet, but we're pretty far down the road— is, is a guide on remote work and distributed teams. So we are 50% distributed team at Holloway, and it seems trending more and more in that direction.

[52:30] Paul: Right.

[52:31] Andy Sparks: And we were talking with one of our candidates for, uh, to be an author for the guide yesterday. And she said, you know, one of the, one of the really hard things about remote work is that you have all these managers who, one of the higher-ups comes and says, hey, we can't afford to have people in these cities or need to be more distributed or have more remote workers. And the managers have never worked with a distributed or remote team before, right?

[52:57] Paul: They just want them to behave as they did before.

[53:00] Andy Sparks: And, and the managers say, okay, this sounds— this all sounds smart to me, like, I get it, we should, we should do this, but how, how do I do it, right? And, and we're just taking a lot of the same ideas for how to manage a team that's all in one office, and we're trying to figure out how to I don't know, mold them into sort of a deformed version of management, and when in reality there's just a lot more we're going to have to do. And then there's quite a few people who've been working remote or distributed for decades, and there's a lot to learn from those people, and that's what we'd like to put out there. So that's one that we're pretty far down on.

And then we just published last week a post that was inspired by Y Combinator's request for startups called Requests for Authors, where we publish 6 topics that we're interested in publishing on, and we'll be adding to that every few weeks. We've got a few more planned, and the broad characterization of all the content that we want to publish is, hey, what's everything in your career as a roughly millennial knowledge worker, someone who's 24 to mid-40s, maybe early 50s, What are all the things that no one's teaching in a university that you really need to know to do your job? How to become a manager for the first time, how to hire, how to be, you know, what's the difference between a manager, a director, and a VP? How to start a company, how to manage your career, how to manage your second career.

Like, uh, there's so many different things in there and you could get really deep and technical on how do you instrument your analytics. We just went through that. It's like, how many companies need to figure that out? And it's almost impossible if you Google around for it. So some of the subjects we know we want to publish on are remote work, first-time managers, um, how to— it's the path towards a really significant money-making career for a lot of people. So those are 3 that I remember immediately off the top of my head, and then we've got 3 more that we know we want to do, and quite a few others that are back in the— that we'll be publishing soon.

But in order for us to write on a topic, basically we're just thinking, is there a big audience here, an audience that's willing to pay, and can we find a great author who's willing to dig in and And the author isn't interested in making this, you know, the Steven Pinker show or something like that. Not to take a jab at Steven Pinker, but a lot of nonfiction authors want to write a book because it's their book. And when we write Holloway Guides, it's, you know, it's about building a brand of content around Holloway that everyone can expect that this isn't just one perspective, it's 10 or 20 perspectives. Built into one, and then the reader will know and feel safe that they've got all the knowledge that they need in order to make their own decisions.

[56:04] Paul: Are there any books— a couple questions left— are there any books that you keep coming back to, or ideas influence you in a powerful way?

[56:17] Andy Sparks: I discovered Mastery a long time ago, and Mastery is by Robert Greene. Robert Greene. Robert Greene. Yeah. It's like Mastery has just been a really interesting book. I think that Robert Greene gets kind of a weird rep because he, he wrote The 48 Laws of Power, but Mastery is actually an amazing template for how to think about navigating career and getting really good at something.

So that is one. I also really love this book called The Art of Possibility. By Benjamin and Rosamund Zander. Seth Godin mentions that one a lot.

[56:56] Paul: Oh wow, yeah, he's the conductor of the Boston Symphony or Boston Pops.

[57:02] Andy Sparks: So it's this couple that wrote the book together, and the audiobook is particularly cool because they narrate it together, and she'll do one chapter, he'll do another, they'll kind of comment on it. It's just these different ways to think about life, and they have this one that I particularly like called Give Yourself an A, which sounds really corny, but as he was teaching at the Berklee College of Music, he wanted to experiment with what would happen if at the beginning of the class he had every student write an essay with the prompt, if you were to receive an A in this class, tell me what you would have done over the next 3 months. So they turned the essay in, and he said, congratulations, all of you have an A. Now go do everything that you said you'd do on the paper. And he said it was one of the most creative semesters for the students because they weren't worried about getting an A.

They were just— they had set their own bar of quality and now they had to go hit it. And it's just little stories that I like in that one a lot. And then I'll give you a couple more. Last year, 2018, was like the theme of the year was the year that I fell in love with Kurt Vonnegut. A friend of mine gave me his biography, and I read his biography. And then as I read his biography, I read most of his books.

And then I also read a collection of graduation speeches by him called If This Isn't Nice, What Is? And man, that guy just had a lot figured out. He had a lot not figured out too, but yeah, just a lot of wisdom from him.

[58:37] Paul: I think you You wrote about him, and one of the quotes you called out was something that I absolutely love. I grew up in a really big family, and he has this famous quote, which I can't read verbatim, but he says, 'You are not enough people.' And he says, that's the title of like the hook. He's used in a lot of different books and speeches, but basically it sums down to a lot of our troubles or challenges are based on the fact that we're living in too small of groups now, and that when you meet people in large families, they're not solely dependent on one other person for their happiness or things like that. And a lot of our troubles can just come back to 'you are not enough' people. And I just love that.

[59:26] Andy Sparks: It's, uh, yeah, he's talking about, you know, when there's a conflict between a husband and a wife, you know, you can almost always narrow it down to the fact that they're trying to get that one person to be too many people.

[59:38] Paul: So I'd love to end with, maybe you can tell us how life is a lake.

[59:46] Andy Sparks: So this is one of my favorites. I was walking with Danielle, my co-founder at, one of my co-founders at Mattermark. I remember where I was when we first talked about it, because we were just kind of, we were walking, taking meetings in Boston. And I told her, you know, I think that life is like a lake, but it's a lot deeper than most people imagine. And that kind of sums up how I think about life, uh, that every relationship you have with a person could be 300 times deeper than you think that it is. Every experience that you have, even if it's just cooking dinner, can have a lot more depth than you think that it— than you might think that it does.

And I took this metaphor and I've actually extended it quite a bit now. My friend Carrie, she and I, we were having drinks with another friend of ours one night and we're talking about, wouldn't it be cool taking this kind of Kurt Vonnegut example of the community? And what if you just got deeper relationships with 30 or 40 people around you, built your own community instead of joining a church or joining an organization? You just built your own crew, not of 3 friends who get dinner every once in a while, but like 40 people. And from that, what I decided to do was take— I came up with a list of 30 people and I created an email list. I don't use anything, I just put them all on BCC.

And about once every 2 months I write them this letter and I call it The Lake. And I just tell it, it's like, this is how I'm feeling, this is what I'm thinking about, these are all the things in my life. And sometimes it's rambly. It's almost always rambly. And I mean, it's like very personal, very personal. And the first time I sent it, I was almost sweating.

And then the responses that I get back from this every time are so cool. I mean, it's like, sometimes people will write me 19-paragraph responses. And other times, you know, I won't have seen a friend of mine for 6 months, and we get together for a beer. And they're like, oh my god, I just read that. And I and it's so connected with these things. And then we have this amazing conversation.

And we don't talk about the weather and we don't talk about sports and we don't talk about, you know, the monotony of who's upset with whose bosses. We talk about like, what's the real deep meat of what you've been talking about or thinking about? And I just love that. I think it's a much more sincere and genuine way to get to know a person than I don't know whatever the alternative is, but that's the like, that's the idea.

[01:02:19] Paul: I love this idea.

[01:02:22] Andy Sparks: Yeah, it's cool. Now, now Carrie, who's, who kind of co-came up with the idea with, she has now started her own version and she sends these emails to some of her friends too. And it's so cool to just get someone, you know, to get one of your friends to write 20 paragraphs and to read what they're thinking. You're like, this is so intimate. This is really cool.

[01:02:41] Paul: So I had a wonderful conversation today. I will link people up to the Good Work newsletter, which I highly recommend. And where else can people find you?

[01:02:52] Andy Sparks: So yeah, everyone can find us just at holloway.com or @holloway on Twitter. I'm @Sparkzilla, S-P-A-R-K-S-Z-I-L-L-A. That's what you get for choosing a Twitter handle when you're 19. I don't know. I think the only thing, one of the things I find is a continuous learning for me is just that Life can be deep, and it can be a lake, and it can be a well, or it can be this amazing rich experience. It sounds very serious, but it's also just— you can't take it too seriously.

My favorite people do not take life too seriously. They don't take their jobs too seriously. They don't take their careers or their relationships— I mean, they're very, very intentional people, but you've got to just be able to laugh at all of it. So I don't know, that's what I'll leave everyone with.