Tag Archives: tech

057: Jim Estill, CEO, Danby
Jim Estill at Danby in Guelph, Ontario, Canada (Official Photo)

057: Jim Estill, CEO, Danby

“Do the right thing. And don’t be afraid to do the right thing… even when there’s a little bit of controversy.”

Welcome to Notes on Doing, conversations with people who love what they do.

I’m Jenna Matecki.

Our next episode goes to Jim Estill. Jim is the CEO of Danby, a Guelph, Ontario-based manufacturer of electrical appliances. Jim recently took over a million dollars of his own money and organized a massive community-wide effort to sponsor and support over 58 Syrian families immigrating to Canada. Jim also is an immensely successful businessman who, throughout his career, has invested in, led, and scaled companies worth billions of dollars.

Listen to what Jim had to say about inspiration, intuition, time management, cowboys, the psychology of failure, entrepreneurial angst, and doing the right thing.

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Thanks for listening to Notes on Doing episode 057 with Jim Estill.

Check out danby.com/donate for ways that you can help Jim’s Syrian friends. Jim also has a blog where he writes about his philosophies on leadership and time management at jimestill.com.

And, as always, subscribe to Notes on Doing. Episodes release twice a month on iTunes. Please rate the show on iTunes (I’d really appreciate it), follow our Instagram @notesondoing, and join the Notes on Doing Facebook community group.

Until soon! In the meantime, do you.

056: Charlie O’Donnell, Venture Capitalist
Charlie O'Donnell, Photo by Christopher Michel

056: Charlie O’Donnell, Venture Capitalist

“There’s some level of positivity in just the ability to keep going.”

Welcome to Season II of Notes on Doing, conversations with people who love what they do.

I’m Jenna Matecki.

Our next episode goes to Charlie O’Donnell, the venture capitalist behind Brooklyn Bridge Ventures. Here’s what Charlie had to say about starting his own fund, investing in people because of their character, the work and time that goes into making ideas fly, the moments when he didn’t realize that things were actually going well, and having a job that he’d still do – even if he had a blank check for life.

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Thanks for listening to Notes on Doing episode 056, with Charlie O’Donnell.

Follow what Charlie’s up to at thisisgoingtobebig.com and on Twitter and Instagram at @ceonyc.

And, as always, subscribe to Notes on Doing. Episodes now release twice a month on iTunes. Please rate the show on iTunes (I’d really appreciate it), follow our Instagram @notesondoing, and join the Notes on Doing Facebook community group.

Until soon! In the meantime, do you.

 

055: Dan Maccarone, Charming Robot, Story in a Bottle
Dan Maccarone, Official Photo

055: Dan Maccarone, Charming Robot, Story in a Bottle

“I know that when I get bored, it’s dangerous.”

Welcome to Notes on Doing, conversations with people who love what they do.

I’m Jenna Matecki.

Our next episode goes to Dan Maccarone. Dan is the Co-Founder of Charming Robot, a product design company. He also interviews people for the company’s podcast, Story in a Bottle. Additionally Dan has a bar named Fool’s Gold, on the lower east side of Manhattan.

Listen to what Dan had to say about starting a newspaper at age ten, performing sketch comedy off broadway, lovingly arguing with Charming Robot’s clients, partners and team about user experience, the secret to running a great bar, creating a familial business, interviewing people for Story in a Bottle, and the pursuit of never getting bored.

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Thanks for listening to Notes on Doing Episode 055 with Dan Maccarone.

Check out Dan’s company Charming Robot, and listen to his podcast Story in a Bottle on iTunes.

And, as always, subscribe to Notes on Doing. Please rate the show on iTunes, follow our Instagram @notesondoing, and join the Notes on Doing Facebook community.

Until next week. In the meantime, always do.

 

 

053: Scott Beale, Laughing Squid
Scott Beale, photo by Lori Dorn @HRlori

053: Scott Beale, Laughing Squid

“I haven’t had a ‘job’ since ’98.”

Welcome to Notes on Doing, conversations with people who love what they do.

I’m Jenna Matecki.

Our next episode goes to Scott Beale. Scott is the Founder of Laughing Squid, a blog that features art, culture and technology. Laughing Squid also functions as a cloud-based web hosting company.

Listen to what Scott had to say about ironic t-shirts, multimedia gulch, Burning Man, Santa Claus on the Williamsburg bridge, and a 21-year-old cephalopod (or should I blog!?) named Laughing Squid.

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Thanks for listening to Notes on Doing Episode 053, with Scott Beale.

Check out Laughing Squid across the internet at @laughingsquid.

And, as always, subscribe to Notes on Doing. Episodes release weekly, every Monday on iTunes. Please rate the show on iTunes, follow our Instagram @notesondoing, and join the Notes on Doing Facebook community.

Also, there is now an original Notes on Doing poster illustrated by Luna Adler. Links for Luna’s Etsy store are featured on notesondoing.com. Check it out and buy it! Also know that 100% of all proceeds directly support Luna, @lunaadler.

Until next week! In the meantime, always do.

041: Sarah Lim, Product Writer / Content Strategist
Sarah Lim, Photo by Red DeLeon, http://red-deleon.com

041: Sarah Lim, Product Writer / Content Strategist

Sarah: Maybe it’s just those few things. Being real. Speaking from the heart. And not filtering as much. Not editing, and leaving that for later.

Jenna: Said a copywriter.

Sarah: Yeah. Said a copywriter.

Welcome to Notes on Doing, conversations with people who love what they do.

I’m Jenna Matecki.

Our next episode goes to Sarah Lim. Sarah is a Product Writer and Content Strategist who has worked on copy for Kickstarter, Oscar, Tumblr, and more.

Listen to what Sarah had to say about lists, languages, haiku, and her moniker, Slim.

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Thanks for listening to Notes on Doing episode 041, with Sarah Lim.

Check out Sarah’s Tumblr slim.tumblr.com, Twitter @awakinglim, and Instagram @sl.im.

And, if you liked today’s episode, Tweet me @jennamatecki with your favorite parts, and please rate the show on iTunes! Episodes release weekly, every Monday.

Until next week! In the meantime, always do.

 

Photo by Red DeLeon

034: Dennis Crowley, Foursquare, Kingston Stockade FC
Dennis Crowley, Official Photo

034: Dennis Crowley, Foursquare, Kingston Stockade FC

“I love the unknowns.”

“Why start things? Why do things on your own? Because you get really great people that are inspired and motivated, and they want to see something happen. To work with those people is amazing.”

“We made something from scratch that didn’t exist before we did it, and people like it. And that’s the thing that’s most inspiring me.”

Welcome to Notes on Doing – conversations with people who love what they do.

My name is Jenna Matecki.

Our next episode goes to Dennis Crowley. Dennis is the Co-Founder and Executive Chair of Foursquare, and the Founder and Chairman of Kingston Stockade FC – a new semi-pro soccer team based in Kingston, New York.

Listen to what Dennis had to say about how he got to where he is today, building things from scratch, and loving the unknowns.

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Thanks for listening to Notes on Doing episode 034, with Dennis Crowley.

Definitely check out a Stockade game — the next one is this Sunday! You can learn more about the team, how awesome they are, and when they’re playing at stockadefc.com.

And, subscribe to Notes on Doing! Episodes release weekly, every Monday, on iTunes. Be sure to check out the Notes on Doing community Facebook group where you can chat with people from the show and our Instagram @notesondoing.

Until next week! In the meantime, always do.

 

029: Ari Shahdadi
Ari Shahdadi

029: Ari Shahdadi

shadadhi-quoteWelcome to Notes on Doing, conversations with people who love what they do. My name is Jenna Matecki.

Our next episode goes to Ari Shahdadi. Ari is the current VP of Business Development at Buzzfeed and formerly Tumblr’s first General Counsel.

Listen to what Ari had to say about the mechanics of being a lawyer, starting over, saving the Internet, and making an impact.

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Thanks for listening to Notes on Doing episode 029 with Ari Shahdadi.

Check out Ari’s Twitter at @arishahdadi, and just for kicks you should totally endorse him for something random on LinkedIn. : )

And, subscribe to Notes on Doing! Episodes release weekly, every Monday, on iTunes. Follow us on Instagram @notesondoing and be sure to reach out and let me know if there’s someone that you’d love to hear on the show – my email is jenna@notesondoing.com.

Until next week! In the meantime, always do.

 

020: Jeff Weisbein, BestTechie, Kya Analytics
Jeff Weisbein, Brooklyn 2015

020: Jeff Weisbein, BestTechie, Kya Analytics

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Welcome to Notes on Doing, conversations with people who love what they do.

Today’s episode goes to Jeff Weisbein. Jeff is the techie behind BestTechie.com, a tech news website. Jeff is also the brain behind Kya, a revolutionary audience analytics and insights platform for content publishers.

Listen to what Jeff had to say about a certain 13-year-old tech genius, the human side of gadgets, and making what you want to happen, happen.

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Thanks for listening to Notes on Doing episode 020 with Jeff Weisbein.

Follow Jeff on Twitter at @jeffweisbein, and go check out BestTechie at besttechie.com and Kya’s publisher analytics platform at getkya.com.

Also, we’re having out first ever Notes on Doing meet up on Thursday, February 11th from 7:00-10:00pm at MatchaBar in Williamsburg, Brooklyn. Come hang out with the people featured in NOD, other fans of the show, and yours truly.

AND, subscribe to Notes on Doing! Episodes release weekly, every Monday, on iTunes. You can also follow Notes on Doing on Instagram too @notesondoing.

Until next time! In the meantime, always do.

005: Rick Webb, Writer
Rick Webb, New York, 2015

005: Rick Webb, Writer

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Our next NODcast episode goes to Rick Webb, a writer, tech advisor, venture partner, angel investor, marketing and sales consultant, board member of the VCU Brandcenter, former co-founder of The Barbarian Group, co-founder of Archenemy Record Company… (we can continue but we’ll leave it here).

Here’s what he had to say about growing up in Alaska, the story behind his enviably awesome career, and his thoughts on life, death, work, and economics.

Subscribe now to get weekly Notes on Doing episodes on iTunes.

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Jenna: Is your phone off?

Rick: Yes, it’s off… but there’s the other one, hold on. I’ve got a lot of phones.

Jenna: No blinking! [Laughs]

Rick: That one is off… that is off.

Jenna: I have to just test the sound before we start…

Describe Alaska.

Rick: It’s shitty. It’s cold. Everybody goes there in the summer and they think it’s very pretty, but they don’t go in the winter. Everybody’s depressed, and killing each other, and doing too many drugs. It looks like Mars. There’s 300 inches of snow and it’s dark all the time. And it’s below zero and it’s really horrible. That’s Alaska.

Jenna: Was it always horrible?

Rick: Yeah, it’s a terrible place. [Laughs]

Jenna: How come?

Rick: That’s a very unpopular view point. People are very attached to the romantic notion of Alaska, but it’s kind of a shithole.

Jenna: When did you move away?

Rick: For college, when I was 18, so 1990.

Jenna: And you went where for college?

Rick: Boston University.

Jenna: You stuck around in Boston afterwards.

Rick: Mm-hmm, for a long time. It’s hard to say when I left, really, somewhere between 2002 and 2008.

Jenna: Wow.

Rick: I mean I kept an apartment there until last year.

Jenna: Just because you’ve always loved Boston.

Rick: There’s something about Bostonians, they’re good people. They’re angry, but they’re faithful. I was just thinking about it the other night, after I saw you, actually. I was walking back to the Bedford Stop, I was like, “This neighborhood has changed more in the 4 months that I’ve been gone than Boston has changed in 20 years.” You can still go to a bar in Boston after about not being there for 20 years and walk in and the bartenders will know your name.

Jenna: Is Alaska the same?

Rick: No… no. The people that adapt well and succeed in Alaska that didn’t crack or leave, tend to be a little reclusive, you know what I mean? It’s not like when you go home you’re going to go to the Big I International and see the same people that were there 20 years ago because they would have cracked if they had been doing that that whole 20 years, so they tend to hide away in their houses.

Jenna: What do you mean by “cracked?”

Rick: Well… it’s just really bleak. There’s a lot of alcohol abuse and drug abuse. There’s a lot of broken homes, there’s a lot of poverty and a lot of suicide. The society that you are in there is very hard to be something that’s nourishing. There are good parts, good people, but typically, if you have your shit together there and you’re doing well, it’s cause you just stopped going to that whole part of society.

It’s funny, when you go home, you have to… When you go to Boston, you don’t have to tell them when you’re coming, you just show up again and you’re like, “Hey, I’m here.” They’re like, “Ya, we’re here. What’s up?” When you go back to Alaska, you got to figure out who’s still in the state and who’s actually sane, then agree to go where they want you to go see them because you can’t just go to a bar and be like, “Everybody, let’s go to the bar tonight” cause they have figured out that the way to deal with being in that state is do not go to bars all the time. You know what I mean? It’s a different kind of place.

Jenna: Did you always know you were going to leave?

Rick: Yep. I always did. Never had a doubt.

I think when you grow up there, you don’t have the same romantic attachment. You know what I mean? It’s cold and it’s snowy and there’s a brief summer that’s a little bit more bearable, but you’re covered with mosquitos. When you grow up there, maybe this is just me, but I don’t feel alone in this, I think you’re not swayed, you’re not distracted by this rugged, cool, weirdness isolation of the place.

Lots of people that move up there, love that. They get totally into Alaska, they go live cabins, they get into hunting and snow shoeing, hang out with moose or bears or whatever, but those people typically aren’t from there. They grew up somewhere more pleasant and they’re looking for a more raw, authentic experience, but when you grow up in a raw, authentic, horrible place like that, you tend to not romanticize it.

I don’t know. Alaska’s, actually, it’s like a big part of everything because it’s in the union, it’s a state in America. It’s not a third world country, but it’s also kind of awful, and very apart from the rest of the country and very different. It’s physically thousands of miles away. The climate’s different, the economy is different, but it does have this American structure to it that’s in an equivalent sort of place. There’s rule of law, more or less. We have a stable currency. It’s not like growing up in Mexico, I would imagine, or something like that. There’s no organized crime, per se.

It’s a very “dichotomy,” it’s a big dichotomy in your life. You’re an American, but you’re always outside of the American experience. You look at it in this way where you’re like a participant, but not a participant. I think that colors most Alaskans that leave. And the ones that stay, I suppose. They’re not like a people, like you go to Iceland…

My first time I went to Iceland 15 years ago, I was struck by the fact that it’s… Reykajvik and Anchorage are the same parallel, they’re both on the 66th parallel. They’re very much the same size city, there are about 250,000 people, but Iceland’s this beautiful town. There’s architecture, culture and art. The people are friendly and warm. They have their act together even when their economy shit the bed with the 2008 stuff, it’s a real culture. And I was very fascinated with that.

I was like, “Why isn’t Anchorage like that? It’s the same size, it’s the same climate. We could have made Alaska into an interesting place,” but no, they just didn’t bother. I do think it’s that American attachment. There’s Alaska pride, to some extent, but they don’t really think of themselves as a distinct people separated from us in America. I think it hinders the entire creative output of the state in some way. That’s a horrible thing to say, but I do think it’s true.

I bought this awesome, Icelandic parka. It’s beautiful, well-made, amazing, and modern. I was like, “Why don’t Alaskans make clothes appropriate for their environment?” But there aren’t any. There’s no amazing, Alaskan clothiers, right? [Laughs] But there is in Iceland, it’s fascinating.

Jenna: What did you do after you graduated college?

Rick: I hated college, I really did. So I got out really quick.

Jenna: You don’t strike me as someone that would’ve hated college.

Rick: Oh, so tedious. Maybe I chose poorly… I was very focused in getting as far away from Fairbanks as possible. And I didn’t have a lot of money so I went as far away as I could with the best AP credit I could get, right, because that made it cheaper. And BU gave me 3 semesters of AP credit, so I was like, “I’m gonna go there.”

I did love Boston. It’s interesting, it took a really long time to adapt, almost a decade. [Laughs] That sounds really weird, but when Sarah Palin was running for Vice-President, I was like, “This woman has no concept about how the rest of America works.” It took me 10 full years to understand things, like basic stuff like the suburbs. You just didn’t understand what they were, how they worked… or malls…

Now, everybody that goes to Boston knows the downtown is very pretty, it’s very architectural, but the fact that it existed, it blew my mind. Like friezes on buildings. I couldn’t understand like, “Why did people spend all this extra time and money to make that ornamental line across the top of the building? Why wouldn’t you just put up clapboard like everything …” You know what I mean? It took a full, I would say, almost a decade before I could plausibly claim to understand the lower 48… regular America.

College was… I remember, I was really into The Cure when I was young, of course, Disintegration had come out right, so I’d done all this math because I was kind of a math nerd back then. I’ve gotten really bad at math now, but I looked at how many copies that album solved in the United States then pro-rated it to how many people were at BU. And I was really excited because I figured, there was going to be about 15 other Cure fans there. I was like, “This will be great. It’s going to be more than Cary Hillard!” who was my friend in high school.

I totally just obviously [laughs] that math was absurd right? It’s a college. There was going to be more than 15, and The Cure had just come through Boston a few weeks before BU started so there’s hundreds of kids wearing Cure t-shirts. And I was like, “I have no idea who I even am anymore.” My whole identity in Alaska was wrapped up in being a bit of an outsider in an outsider place. And I went there, I was like, “This is rough, everybody likes The Cure.”

I liked it pretty quickly, I liked Boston. I liked living not in Alaska. I never doubted that. But I didn’t really enjoy college very much. Some of the stuff we were talking about earlier like art history. The classes, it’s like, when you’re really… more so when I was younger, but I was really into the avant-garde, whatever’s pushing an art form the furthest forward, then you’d be in a class learning about stuff that was 100 years old. That bothered me at that time and it doesn’t bother me now.

Also, the other thing is I realized I was an Economics major… Well, that’s actually a whole other thing, I started as Computer Science major. I was a computer engineer, I was coding my whole childhood, but I got there and I couldn’t understand my professors, for example. I’d never met anyone from India. I never met a Pakistani. I couldn’t understand their accents. That’s just typical… I didn’t know how to be a person in a society that… You know what I mean? So I switched majors to Economics, but I didn’t know anything about the academic disputes that happen in Economics between fresh water and salt water. It’s so boring…

I realized that I wasn’t learning so much as I was being programmed, and that really bothered me. I was like, “I got to get out of here,” so I just got out and I just stopped. I mean, I finished, I graduated, but I did it as quickly as possible. And I went back to Alaska for 8 months.

Jenna: Why?

Rick: So at that time, it seemed like a very good deal. My parents were like, “Hey, drive your sister around on her college tour. You’re graduating in December.” They’re like, “if you drive her around in May, we’ll pay your rent from now till May and we’ll give you 2 grand to buy a car and drive her around,” because in their head, that math is way cheaper than flying them out… It just made sense, and so.

I graduated, I had no idea… Compared to the recessions that have followed, it wasn’t a terrible recession in 1992, but it was bad. I’d made some tepid efforts at applying for jobs and it wasn’t really working, so I latched on to this and I went home. I drove her on this 8 week road trip then we went home.

Honestly, I have my sister to thank. I would’ve just stayed there. I was pretty settled in. I started a radio station there with some friends… I was starting to figure out how to book bands there. I had a really good apartment that was open enough. I had joined a band with my friend Jason and it wasn’t bad.

I was kind of making a go of it. I had a good job. I could’ve easily… I liked my girlfriend, I could’ve just easily stayed there forever, but my sister is a lot like me, or was then, and decided to go to Northeastern in Boston because it’s the only place she was spending time when she’d be coming to visit me. She was like, “You’re coming with me” so I went back. Thank God. Thank God, thank God. I owe her my life! [Laughs]

Jenna: So what’d you do when you moved back?

Rick: I got back and that was really when I decided I was going to make a go at it, at anything artistic and really, really go for it. And I fell in with a really good group of people that are my friends to this day. We just tried everything. We joined bands, we started a record label. I started a design firm with a friend. We had an art collective. We just did all. We all went in on this loft space workshop. We built a dark room in it, and we built a soundproof rehearsal space and had a woodworking shop, and we just did everything man.

I did that for… I guess I got back in ’93, early ’93. From then until we started Barbarian Group, it was like…

The other thing that happened is the internet, that helped. Back when I learned how to code there was no real reason. What I realized I was when I got to Boston, was that I was going to end up working at DEC or some company out on main frames out on route 128. It just didn’t really appeal to me as a life career path, but once the internet came along, then you’re like, “Oh … The computers are actually… you can do art again.”

That changed a lot, a lot.

So web design, we were really into the early font designers, well, not early, but independent ones like this guy Chank Diesel out in Minnesota.

These people are still some of my closest friends. They are all doing interesting things with it still, in different ways. Some of them are in a pretty successful band, one runs a design shop, one guy, he’s a curator at one of the national museums, part of the Smithsonian. They’re all doing interesting stuff.

And we just went for it. We just did everything we could. We put bands on tour, we organized shows, played shows, put out albums, handcrafted boxes for the CDs.

There’s this band called The Rachels we were really in love with. Actually, just Rachel’s not really “The.” They had letter pressed the album using their own blood in the ink. We were like, “…That’s what you got to do!” And we went for it. I should show you some time, that band’s first album, it’s in this handmade box, with like a Polaroid that we silkscreened onto it… It was wonderful.

Yeah, so we did that. Because of the internet and the demand for people that could do anything with computers, I could work about 10 hours a week. And rent was $200. And so we just worked as little as we needed to get the money to do more of the stuff.

That was it. That was all we cared about for 6 or 7 years.

Jenna: What did you want for yourself back then?

Rick: I didn’t really know. There was no… That was it. We were very happy. I remember some band I really liked, they played at Paradise which is about a 500 person room. I looked at their tour dates, basically, they were playing in the United States and they were playing in rooms that were like… Boston was probably one of their biggest shows right, except for New York, of course… but…

They played at Kansas City in a room of 150 people. They did this 4 week tour, they’d come every year and they lived in Minnesota. And I was like, “That’s the life. If you can get enough people in each city, a couple hundred people to show up, and play your show and move on, what more do you need in life?” That was literally it.

I was also really obsessed with Roger Waters not as an artist, but the fact that the guy can walk down the street. Nobody even knows what Roger Waters looks like, and this man has sold as many albums as the Beatles, right?

I just think it’s really interesting. He can walk down the street and nobody knows him, it’s not like a thing. It’s not like a cult of Roger Waters. He just worked at his music and makes these weird tours.

I thought that was appealing, but really, I think we would’ve been happy if could just play in rooms to 500 people forever.

That was pretty much the goal. And have the label do okay. Yeah, that was the goal. That was it.

Jenna: Why wasn’t it forever?

Rick: Well, the big thing that changed was Barbarian Group, really. And it was kind of a fluke.

There was our bands, on our label, my band the Rockets, Freeze Pop, Neptunes, some of these bands are still around… Then they’re our friends. The Elevator Drops and Ghost of Tony Gold…

One thing that happened is a lot of people just… About half of my friend group decided to move to L.A. at once. Like 40 people.

Jenna: Why?

Rick: Well, The Drops wanted to make it big, they were signed with BMG and they were doing okay. They wanted to make it big, and people felt like Boston’s Arts Community… we were all kind of it. There was some Fine Arts stuff. This guy Paul Richard, he lives here in New York now. You see his signs around. They’re really great. He’s got right now a ‘For Sale’ sign right now on the Bushwick Inlet, it’s really good.

Anyway, he was around. There was some fine art, but the scene was not huge. I found it very rewarding, we all liked each other, but a lot of them, they wanted to really go for it.

So they all started moving out to L.A., and honestly, it was super fun. I was going to move with them, I’d go visit. My friend picked me up, and we were hanging out with Christina Ricci, Nev Campbell, the Marilyn Manson guys. L.A. was drawing us all in. I was about to move there.

Then my Ben, my partner was like, “Hey, I got a great idea, we’re going to start this company” and described the plan for the Barbarian Group. And I just knew it was going to work.

He was like, “We’re going to do this, this and this.” I was like, “Oh, that’ll work. Let’s do that.”

I didn’t really think too much about it because we’re always starting these things. We had already started a record label. I’d done already at least one design company with my friend, Annie, so I was like, “Yeah, okay, we’re going to start another one. We’re going to do it right this time” because we had a little bit more access from our day jobs that had been doing in advertising and… I just knew it would work.

In my mind, I was going to give it 5 years. Literally, there was this week where Ben was like… where I just locked up a room in L.A. He’s like, “Are going to do this or not?” I was just like, “Okay, I’m going to do that. I’m all in.” And the absence of all the friends helped in a way because it let me focus more.

Barbarian was interesting because it was much more conceived as more of an arty thing, at the beginning… commerce sort of changed over time as the web industry evolved, but if you look at the early years, especially, it was very artistic. It didn’t really seem that much of a big step.

I really didn’t know how the ad industry worked. I didn’t really think about that stuff. It was like, “Oh, we’ll get a bunch of artists together and we’re going to make some money.” That’s cool. We’re going to make money doing school digital art, which we were all into because it had gotten interesting with flash and things like that.

It wasn’t super considered, but there was a moment of truth where it was like, “Okay, we’re going to do that.”

That was in 2001, end of 2001, right after 9/11.

Jenna: What was your role in the company when you were brought on?

Rick: Well we started it… it was Ben, me, Keith, Robert. Robert Hodgin, Keith Butters and I were working at Arnold. Ben had freelanced at Arnold and had worked at a startup called De-mod which was like a DRM type company, he was the art director. We just all started as equal partners. We did it really well. It was kind of flawed because we all did the same thing. We’re all into just different aspects of making art using technology.

Keith was probably a slightly better coder. I was a coder, Ben didn’t code at all. Robert was getting good at coding. Robert had a really good fluid, motion style, Ben had a very dark style… but we were all the same. There wasn’t like… in Mad Men you go to start an agency with one account guy, one finance guy, one copywriter, one creative. We didn’t. We were 4 dudes that all did exactly the same stuff.

It took a while for us to find our individual roles. So we all just did everything.

But I would say, by the second or third year, we had sort of figured out who was doing what. And I ended up with running with all the finance, account and project management stuff which I was the better of the 4 of us at, but by no means any good at. I got better later, but …

Jenna: What year… what year are we talking about right now?

Rick: We made the plan in the summer of 2001. I remember very vividly that I was going to quit the week 9/11 happened. Actually, I did quit, I quit the week before.

Jenna: Quit Barbarian or quit…

Rick: I was working at Arnold. Yeah, I skipped over that. [Laughs]

About a year earlier, I’ve been with Arnold about a year. They just bribed us. None of us wanted to work full time. A woman there was like, “Just, how much will it cost you to work here?” I just threw out a ridiculous number and she was like, “Okay.” It just felt really irresponsible to not do it. It was a good place. As an agency at that time, it was really good and people were good, but… yeah, so I quit that job the week before 9/11. When 9/11 happened, my boss was like, “Well, I got good news and bad news. I haven’t turned in your resignation letter yet so you can rethink it if you’re having doubts in this new world. The bad news is, we’re going to lay you off anyway tomorrow because we’re rethinking, we don’t know what’s going to happen.”

So I stupidly just said, “I’ll leave anyway.” I should have collected unemployment. I don’t know why I didn’t. I was young and prideful… you know what I mean.

So we started in the end of 2001. Then, I would say, we worked out of Ben’s house until his girlfriend kicked us out. Then we moved over to my apartment. And by mid-2002, we’d gotten a good job with Goodby, for Saturn, and got an office.

Jenna: Was it fun?

Rick: Yeah. In the beginning, it was really interesting. We could do some really interesting artistic stuff. The internet was a fascinating playground of change.

We started before YouTube. We started before all these things, Flickr, Google. [Laughs] It was a very different place. Each of these things would come along and we would explore them as new mediums. It was really fun. We did the first paid stuff on YouTube, we did, all the way through forever, we’ve been playing with these mediums as they would come out, Facebook and even through BuzzFeed, we were one of their first advertisers.

That part was really fun. And I started to really appreciate the dignity in giving people good jobs. People loved working there, mostly not always. There was some drama. We were young, we didn’t know what we were doing, but I really appreciated that. We got better as managers. Everybody really liked it and everybody was really happy, the work was really good and we were winning national awards all the time. We were famous. We were getting paid a ton. It was very good for the first few years.

Yeah, it was great.

I think that as we got older as individuals, all of a sudden you’re like, “Hey, we never actually talked about where this is going or what our life plans are.” And there was another guy that had joined us almost immediately at the beginning, we made him an equal partner. He started 2 months after. This guy, Aubrey Anderson, he’s a wonderful man, I love him to death. We all started to want different things and we wanted different things in the company.

You start an art collective that’s a business and you’re going to have different… Everybody’s got their own art/commerce balance in their head and we’d never talked about it. It took a while for us to turn it into something that could be something for everyone. That becomes a lot harder. Like, “Okay, you want to do pure art, you want to get rich, you want to do some more code stuff, you want to do bigger projects, you want to do smaller projects” and try and find a way to accommodate all that, it becomes a different beast.

That made it a different type of thing, but I still found it very rewarding just through giving people jobs that they liked. That was nice. I enjoyed that part a lot. I still do, it’s fun. I miss it right now. Yeah, so we… Now, it’s still around, it’s 14 years old.

Jenna: Yeah.

Rick: That’s crazy.

Jenna: But in between then, I think the year was 2010, 2009-2010, you got acquired.

Rick: Right. There’s 2 things that I think really changed. One is the entire global recession happened, which is a problem. That, we got caught with our pants down a little bit because we have been growing forever, blindly. There was just an infinite amount of demand for our work and we made our peace with growth, it’s a whole fascinating, philosophical topic, but we had decided we were going to grow. I don’t think that’s wrong. I have some personal issues with growth of companies, but I think it was the right move, but when the recession happened, the banks…

Basically, this happened around the world. I wrote about it in the book too. The banks screwed everybody over with the great recession in general. And then to save themselves, they screwed over small business America a second time. Specifically, what they did is they called in literally trillions of dollars of small business credit, right, from companies that were paying. We had a real line of credit and they just called it in.

Against the terms. The just violated the terms. There’s probably some clause in there that says, “At any point for any reason, we can negate this whole agreement” but you never expected them to, and they just did. We actually survived that, but there was rounds of layoffs, and tensions. I had lots of friends that owned other agencies that just went out of business in this period. A really good friend of mine in Kansas City owned a great company that was doing motion graphics stuff in film, just wonderful, brilliant people just, kaput. We had nothing to do with any of these companies, we were still profitable, but they were just like, “Well, you have to pay us a million dollars tomorrow”, and you can’t do it.

That definitely put pressure on for sale, but really, we could’ve withstood that. We definitely didn’t do a fire sale or anything like that, but it did open my eyes to certain things. The other thing is, I think, social…

Social is, I think a huge thing.

Me and Noah who was our head of strategy there and he’s the CEO of Percolate now, we debate this to this day, but I do think social completely changed the ad industry. I think it changed it in a couple of ways.

It changed it for brands having to deal with the public, right? For pretty much no logo… Naomi Klein, sweatshops, like the WTO protests in Seattle onwards, humans have had a more cynical take on brands, there’s historical roots to it, but now… you can take down a brand.

Like JetBlue’s CEO got fired because one person tweeting on a plane, they got stuck on the tarmac for 12 hours. It’s changed the whole industry. That’s fine. I don’t think it’s bad. People should have a voice in the industry, but what it has changed as well is the type of creatives that are drawn to working in the ad industry.

I think storytellers are thriving in social, and I think fine artists are having a harder time. I think different types of artists with different temperament, have taken to social better than others. Does that make sense?

Barbarian was not… It was as a traditional digital agency which is a funny thing to say because before, there wasn’t… But as a digital creative agency, it was very good, and very “of the people” and it made work, that was of the people, and it felt populist in a way, but it’s a very different thing to be social. It’s a very different thing when your agencies, all they’re doing is making videos…

You’re a filmmaker, this is all good for you because what’s happened is filmmaking is what the web is now. But we were very interested in interactivity. That has gone away. People don’t make beautiful, interactive websites the same way, like Google does, and a few other people, but it’s like, the bread and butter of what we did, this innovative interaction design and stuff has gone away. Now, it’s writing, and video.

A lot of people love making films and writing. And I’m a writer, I like that part, but the agency we had built wasn’t as solid for that, so it necessitated a lot of changes. I think they’ve handled it very well, and Barbarian does a lot of good social work now, but it wasn’t what I wanted to do in the ad world. The ad world worked for me because I was fascinated with technology and creativity and interactivity specifically, whereas now it’s like you make videos, and you write things and you stick them on a Facebook page.

Jenna: Is that why you left Barbarian?

Rick: Yeah, basically. Yeah, that’s a big part of it. Just the nature of it.

One day I was like… I had ideas, we had ideas about how to handle this and I talked to a lot of other agencies and they had the same ideas, but one day I just woke up and I was like, “You know, my partners like running this agency. They own an ad agency and they’re running an ad agency. That’s actually very rational. Whereas I sit here and I’m running an ad agency and own an ad agency and I don’t like running an ad agency… so I’m the weird one.” [Laughs] I’m like sitting there trying to change the agency and do startups within the agency, and I was like “wait a minute, I’m the weird one. They like doing this.”

So that was this big epiphany. Then I was like, “All right, I should just go.” And it was very sad. I had also convinced some people there that we had this means of carrying that on… and I think they felt like I abandoned some of them, but over the long term, it was the right thing to do. So the agency has shed a lot of its baggage around that stuff and can make the kind of work that is needed of it today, which isn’t what I was really good at. I can’t deal with social in that way. I don’t care about content strategy. I’m just not… that’s not my thing.

So yeah, it was the right thing to do, but it was pretty painful. It was like when you break up with someone that’s really good for you, but not the right person. You know what I mean? It kind of sucked, actually. But it was also a big relief. Also, we had grown to a size that we were comfortable with and there wasn’t a real desire to grow to be a bigger, crazier thing. I think the COO part of me would have… not…

If we were going to grow this thing to a thousand people and take on RGA, there would’ve been something to do more. I could’ve ignored my creative field and just looked at the business side of it. Because I do like working in business. But we weren’t. I was like, “This thing is really running on autopilot here. I’ve got great producers, I’ve got a great CFO, I’ve got a great Director of Accounts, I don’t really have to do anything. The only time I’d do anything is when a client’s really mad at me and they talk to me on the phone.”

That’s literally all my job was, answering the phone, talking to irate clients once every couple of weeks. Not that people got mad that often, but a billing dispute or this or that. I was like, “Well, this is not really a fun job,” so yeah, I left. To this day, I really miss the management aspect, hiring people and giving them a good job. I could do it, it could be a factory, I don’t actually…

Once I realized that was enjoyable in tandem and separate from art, then I could do that anywhere and it would be fun.

Literally, if I would manage a ball bearing factory, if I could make it a pleasant place to work, it’s given me respect for companies like Costco and Publix where the people really love working there, and they’re employee-owned, but yeah, I don’t do that now so it’s very sad. [Laughs]

Jenna: You love giving people jobs yet it seems like you lose interest or lose passion in a job after a certain period of time.

Rick: No, I don’t think so…. Well, there’s a couple of things.

One, I definitely don’t think that’s the case. I could do it a really long time… I don’t like to settle.

The structure of Barbarian was, even before the sale.. there was 5 partners. I was COO so I… We were good, we were mature people that understood we had different roles even though we were partners. I did have a lot of leeway, but I wasn’t CEO. It’s harder to make really bold moves with 5 partners, especially when there’s 5 partners and a large Korean company, all owning it together.

I did get a little restless. But like I said, I think if that company was like, “We need to get to a thousand people.” I would not have gotten bored. I would’ve been happy to stay and keep doing it. I don’t think that was the right move to get to a thousand people, so I think we made the right choice, but there just wasn’t that much to do.

Yeah, if there was stuff to do, and it was something where we could make these bold moves and change, and grow and evolve and try innovative things, I would’ve not gotten bored.

Since then, I definitely, in the intervening years, I’ve been wrestling a little bit with my severe issue with authority.

I’m not real good with working with other people, or at least I’ve decided. What I’ve come to realize is that…

I’m kind of looking at my life in decades now.

There was this decade of almost like collective art that I just loved, it was great. Then there was a decade of collective business which I really enjoyed. Then I went and did some work at Tumblr. Again, I gave a bunch of people great jobs. I get to talk to them all the time. And they’re still very happy in their jobs. That was very rewarding, but it wasn’t my thing. And I had bosses, even though I loved them all.

Then I did some consulting for some companies, same thing, but I was like, “This isn’t what I want to do for the next decade of my life. I want to do something else. So I’ve been in collaborative art and collaborative business, I’m going to try some solo art for a decade.”

That was the big epiphany.

I’m going to spend 10 years just doing art on my own. I’ll still work, I got to pay the bills, [Laughs] but that’s kind of like the MO… decades have themes.

Jenna: If each of these decades had a certain list of things that you learned about yourself inherent in each one of them, what would those lists be?

Rick: You know what’s frustrating about learning about yourself, is the things that are hardest to learn about yourself are your faults.

You’re in your denial about your faults and you learn your faults. That list is always inherently depressing. The answer to that question is going to be depressing for a lot of people, because you learn these things, like there’s limitations in things. You learn that “I’m not good with authority figures.” My mother could’ve told me that at 7, but I don’t think I learned that until my late 30s you know.

I think that the collaborative art decade was where I realized that money wasn’t always evil. That there was something interesting about it. It sort of renewed my interest in economics… and that economics was an interesting lens, especially for an artist because it’s a way to look at the world to see what’s going on, it’s like a hidden code.

I would say, the Barbarian days it was much more about systems, process and organization, and how things can work, the act of making things that are of a high quality through a complex organization. Also, I very much changed my sort of economic, political outlook in that decade as well. I sort of gave capitalism much more of a benefit of the doubt when I was young.

One of the aspects of Barbarian is that we met a large number of world leaders, billionaires, things like that. Seeing the world from that side made me really realize that it’s not this benign, harmless thing that it is. Not because they’re evil, but more the fact that there were no conspiracies. They’re kind of all just idiots. I don’t know how other people get into business and become more fiscally conservative or Republican because I just had the exact, opposite experience.

The more time I spent in corporate America, the more I vehemently opposed the corporate structures of America I became.

It’s weird, right? Most people go into business and they slowly turn into a boring banker, but I came out the opposite. [Laughs]

And this one is too soon, I can’t say yet. I’m only 6 months really into the plan… you know what I mean?

Jenna: How have you changed in the last 6 months then?

Rick: Well, the plan was earlier, I think it was probably 2 or 3 years ago that I was like, “I’m going to write 7 books in my 40s. And I got started right away. I published one in the beginning of this year that I had written over a year ago. And I finished the second one, I’m almost done with the third one.

It was already happening, but what was happening in the first couple of years is I really tried to, what’s the metaphor, split the difference, no. I tried… to butter both sides… no …have my cake and eat it too… maybe. And try to do that while still living in New York, while still having these jobs in technology, being a high-paid corporate consultant while trying to also be a writer.

It took me a little while to be like, “If you’re serious about this, you got to go all in.”

That, really since we moved down to North Carolina in April, is…. new. And of course, it was quite a stretch to pull that off in such a rapid time, so there’s still some financial pressure. We’ve made our lives cheap now, but I still… We spent a bunch of money on a house, I spent a lot of my cash, so it’s still resolving itself to be comfortably living cheap down there and focusing on our… We’re close, I’m close. It’s a little too soon to say, how this is going, but the early signs are very encouraging. I got a lot done, it’s very rewarding.

I do miss working collaboratively in groups or organizations, either artistic ones or business ones, but the whole time I did that, I missed this. That’s actually the other big insight especially around 40, it was like, well you happen to be very good at 2 things that are kind of diametrically opposed, which is sitting at home and writing. I’ve always done it, I’ve been very good at it, and managing complex organizations. You can’t really do both, you know?

So I was trying to do both, I was like, “Well, I did that for 10 years, so let’s do this for 10 years. If I turn 50 and I’m like, ‘I miss it’, I’ll worry about it then,” you know?

Because I’m fulfilling the part I missed then, now.

Jenna: Something that’s always struck me about you is that you’re a convener of people. You bring a lot of people together. You won’t just have drinks with one person, you have drinks with 5-10 people around one big table at a bar.

Rick: I do both. [Laugh]

Jenna: You’re a convener. What’s interesting about you too, that I’ve always noticed, is that you have friends that are in many different life periods. So you might have a friend that is busting their ass in some super corporate environment trying to make a name for themselves. You have friends that are half your age. You have friends that are twice your age.

Rick:  Yeah, I go from 11-80.

Jenna: Right… I think that’s interesting.

Rick: Yeah, I do think that it’s one of the reasons everybody’s so skeptical about us moving to North Carolina. [Laughs] They really think I’m an overly social person. I am to some extent, but there are these things that people do that I always have looked at very askance as an Alaskan.

Like I never understood brunch. I never understood dinner parties. People do them because it’s like a slightly more intimate group. A dinner party at someone’s house with another couple or 2 couples is actually really nice, you get to know these people, but I always hated doing that. I always found excuses to not to do them.

We are sort of changing the way I socialize as well. People come visit us now and it’s very nice because it’s just them. You spend a weekend with you know, one person or a couple and you get to know them in a different way. I do really like that. But I have always enjoyed introducing lots of different people to each other. I like throwing them in and sort of seeing what happens. I’ve always enjoyed that.

But I had a hunch that the needs of… Everybody has different needs, in them, and that I’ve been, especially since moving to New York, over-indexing on society to the detriment of other things that needed to be done, and that a rebalancing was sort of necessary.

I was like, “I could wake up and be 50, I would’ve had some great parties, but if I stay here, I’m going to get nothing done.” And so I said, “Okay, I’ll pull back on the socializing, I’m going to pull back on the business, and I’m going to do some personal writing and projects.”

So far, it’s worked, I don’t miss it yet. And we factored it in, North Carolina, it’s not far, I can still some back to New York. I’m here this week because I started to miss people after 6 weeks of isolation. It was like, “Oh I’ll come visit,” but yeah, it’s fine. It’s fun. Yeah, I’ve always liked big groups of people that get to know each other. It’s fun.

I like seeing that you’re friends with some of my friends now. It’s good time.

Jenna: What makes someone a good person?

Rick: [Laughs] This is a matter of continual debate because I can see the good in almost everyone. I get in lots of trouble… because you end up defending people that shouldn’t be defended, because you can see the good and you can see the misunderstandings. I feel like it’s worth defending people like that, but then you’ve sort of ended up choosing your battles and all of a sudden, you’re a defender of a bunch of unpleasant people. Does that make sense?

That’s a discursive answer, but I’ve been really wrestling with that lately, especially in this internet outrage culture, I’m like, “Oh I can see the other side of that. That person just said the thing in the bad way. We only heard a little bit of a part of it. Look at their lives holistically, they probably didn’t really mean it” or like, “I can see that that songwriter is writing songs as stories and that they’re not necessarily advocating the destruction and overthrow of society, whatever,” but then all of a sudden, you’re this dude on the internet defending these people that say horrible things and just, It’s not my goal in life. I got my own stuff to do.

That’s a long way of saying  I do think people are good. I think there’s evil out there, but good people make evil.

Jenna: What’s your goal in life?

Rick: What… there’s no goal in life. What are you? You’re just going to die. [Laughs]

Jenna: I don’t know, you just said that wasn’t your goal in life. What’s your goal in life?

Rick: I do think that you do have to fill your time with things that matter to you, right?

Jenna: Why?

Rick: Because that’s all you got. All you got is this period from when you’re born to when you die, and it’s yours. And you’ve got to spend it doing things that you find rewarding in some way.

The more those prompts come from outside is… I’m not saying your family, your loved ones, your wife and your kids, those prompts are on the inside too, but… why get involved in a bunch of stuff that isn’t what matters to you? So staying focused on that stuff has become most important.

Jenna: What has been rewarding about your life up until this point and what do you foresee being rewarding going forward?

Rick: Well, that’s interesting um… [Bottle cap Rick’s playing with falls on floor] Mmmmmm…. Now, you’re not going to let me play with my little cap? Come on! [Scrapes bottle cap against microphone while making sound effects].

Jenna, you’re going to edit this out. [Laughs]

Jenna: [Laughs] No, I’m not. No I’m not because it’s something that you did! [Laughs]

Rick: All right, I’ve always had these complex things around both depression and privilege.

If you think about Alaska, that dichotomy of being in the United States, but it’s this horrible place – it’s both. I had a very stable, loving upbringing in Alaska from 2 parents that are together, and love each other, and were public servants in a way that they could have a middle class life that you cannot have any more from being 2 public servants, right?

It’s like I’m a spawn of what was good about America in a place that is what’s bad about America.

When I was young, I had a friend that thought we were rich. And I was like, “It’s kind of a cool country when your mom’s a school teacher and you’re dad’s a fireman, people can think you’re rich. Because you can actually live off of these public servant jobs, you know? And that’s kind of gone now. It does make you realize how lucky you were to have it.

And it makes you aware that it is increasingly rare to get that.

I definitely have sort of thing around that, like luck and privilege. Then some of it, to this day like jury’s out.

I’ve always been good at setting a goal, some, stupid, wildly ambitious goal and then going and doing it. And it’s worked pretty well.

And I don’t know why. I know that part of it’s because I had a good education in a town that people believed in paying their taxes and having schools. And I know that’s actually crumbling in Alaska… but also, I don’t think it’s me, but you don’t know. That stuff has all been very confusing…

I’m always identified as someone that’s depressed. The whole thing and there’s really no point to any of this right? But you’ve got to live with these things and still do something, right? So that’s this whole thing. You could let all of that bog you down… So then when I got rich, it was already very familiar in that way. All of that actually prepared me very well for getting rich. Because it wasn’t anything different. It was like, “Oh I hit another goal, I got this money, but I already know this stuff is meaningless, it doesn’t matter…

And I’ll just keep doing shit. I’ve got to just find another thing to do.”

I wrote this long essay about it. And I just reinvested the money into things that I believed in. That would go to giving people jobs, and kept no cash. So I’m very familiar, I recognize I’m very wealthy, but I have rearranged my life to act as if it doesn’t matter.

I’m really psyched my bank balance is over a thousand dollars this week because I sold a bunch of CDs to a Chinese guy.

And that’s exciting to me. And that was exciting to me when I was 18, I was like, “Oh my God, I have a thousand dollars in my bank. This is awesome,” but the context has changed a little bit, because I’m not secretly… I mean, I’m totally rich, but I don’t see it, don’t have it and can’t think about it, and I can’t get to it.

So that stuff, I think, privileged in that way. I’m a white, adult, male American, you cannot get more privileged than that. Really. [Laughs] Especially now that I’m rich, I just checked off the last box… You got to be always aware of that, but you got to also do what’s important in your life.

It’s kind of hard. It’s a weird thing, it’s a weird line to walk. Yeah, those are the guiding principles now…

Jenna: What’s important…

Rick: What kind of art can you do that works with this, especially as a writer. There’s all these challenges with writing because the whole act of writing, especially long form book writing which is what I’m setting out to do, is in the non-fiction world, especially…

You’re inherently taking this position of, “Here, let me explain how some thing works to you.” You got this whole mansplaining thing going on, because you can see old white authors do that all the time where they’re like, “I wrote a really interesting book on this. I believe that gives me authority to talk about gender issues or something.” Then they just stick their foot in their mouth. There’s like that sort of thing.

The book I’m writing now is just this obscure economic analysis of a bunch of papers written over the last 300 years. I find it kind of interesting, but I don’t think other people will, but it’s great. It’s a topic that I feel like I have something to contribute to. I don’t feel like I’m overstepping any boundaries in anyway… I don’t know. I’m not making a whole lot of sense, but I think that’s the fun way to do it.

What can you express in your art that is appropriate to who you are?

I do think that’s one of the reasons I like economics. It is a prism that you can write about and talk about injustice and make a positive contribution in the world, without it being a white dude telling women how to dress in the workplace or something. Right?

Jenna: Right.

Rick: That was really, really rambling but…

Jenna: Why is it important to always be doing and producing good work?

Rick: Well okay, so I wouldn’t say that. That question has two parts, right? The “good” was an interesting little curveball in that question because, I do very much stay hugely productive at all times because I believe it thwarts depression.

I’m always happier when I’m doing stuff.

Like exercise… I have a very anal routine these days, spit down to the minute… time for exercise, time for free verse writing, time for writing a book, time for doing any of the work I have to do to get paid, time for earning little money through my you know, whatever else, time to spend with my wife.

When I finish a day, I feel better. And I don’t feel depressed, because I did all these things.

Just being active like that is very important, I think, for my mental health. I know I’m not alone in that. I think a lot of people, that create, just create because it keeps them sane.

The “good” part, I think is interesting because I’ve actually stopped caring about that. [Laughs]

I found it very paralyzing for a lot of years. That art was good or not good. And I would…

I think it is familiar to lot of artists and you actually alluded to a story with it recently, and a friend of mine who I was texting with today alluded to one too. Where like, you were doing a thing and you thought it wasn’t good, and then you go to a museum, or you see it on TV and somebody just did that exact same thing and they think it’s brilliant. And you’re like, “I could’ve done that.”

And you didn’t because you didn’t think it was good enough. And it’s just dumb. It’s all in our heads, you might as well just do it.

So, I just don’t worry about whether it’s good or not. I mean, I’m kind of curious if other people think it’s good, but I think right now… I can’t worry about the “good” part too much. I want to just produce it, and deliver it. And if it’s good, great. There’s going to be some hits and some not hits.

It gives you a new appreciation for somebody like Peter Bogdanovich, that had 3 great movies and a bunch of crap movies but he still keeps putting them out because, what are you going to do? Not do it?

You’ve got to keep doing it.

Sometimes it works, sometimes it doesn’t. And I’ve stopped worrying about that, “good.”

Screw good. Just do it.

So, I think, okay, there’s a corollary to that, the act of putting in front of people, promoting and pushing, and trying to make a bunch of money out of it, things like that. I’ve been trying to not do that too much. I’m trying to just put it out and be like, “Hey, I did a thing. Here’s a thing. Some of you might like a thing. If you like this thing, cool. If you don’t like this thing, cool. Don’t worry about it. I’m going to do another thing after this.” And I’m going to do that thing.

I’m not trying to put it on TV. I’m not trying to… I don’t go around bugging my friends about it. People are coming to me like, “I’m so sorry I didn’t buy your book.” I’m like, “I don’t care. It’s fine, whatever. It’s not your thing, it’s fine.” And I feel a lot better right now doing it that way.

It’s kind of like back in the band days…

Bands are this thing where you want to do something that you find really rewarding and awesome and challenging and difficult, but you also want it to be really popular. You make this music… I mean, I made music and one of them is like 6 different tracks of feedback noise. And “I don’t understand why people don’t like this/it isn’t popular?” It’s just… I like making noise, 6 different tracks of feedback and if nobody else wants to hear it, that’s cool.

You should just make it, if you want it to be there.

So I’m actually trying to remove all those barriers. “Good” has been a barrier for me. “Good,” doing it right, making it perfect, all that stuff, I just, I don’t care.

I’m just throwing it out. Just get it out, get it out, get it out, get it out.

Jenna: Is that the path that someone has to take in order to be fulfilled?

Rick: I don’t know. I’ve always found it really interesting when artists talk about their stuff in terms of good or bad. And how they made it good, or “it’s not good yet,” or “it’s not ready.” I’m not… I’m not like that. Part of that is because spending a decade on the internet where you ship fast and you iterate. You know… I’m very comfortable with that process.

At least the atrocities like George Lucas sometimes, where you have like, “Can I just leave I’m so…?” I don’t think it’s the only way. For me, it’s the only way to get anything out right now.

Jenna: Is producing, a lot of work…

Rick: It’s just getting it done and finishing ’em, one at a time. Just banging ’em out and getting them done and move on to the next thing.

Jenna: And that’s fulfilling?

Rick: Yeah, totally. Because you’re making a body work. It’s not all going to be great, but you have something, right?

Jenna: Do you think everyone’s capable of that?

Rick: I think it would it make it easier for people to do that. I do think a lot of people, whether it’s good or not, is a big obstacle. I don’t know.

I‘ve been listening a lot to Phosphorescent lately, this band, one-man band. Everything is so nuanced and complex, and really well done. It’s very obvious, this man, has spent his life becoming really great at doing this thing. It’s like there’s this technical mastery.

And that’s not me. And I couldn’t do art that way.

Every time I get that far along in something, I get bored with it. I don’t want to… I’ve been thinking about this in my writing, so I’ve been starting with these non-fiction books, and I’m going to write a novel eventually.

I really… My favorite novelists are all basically antithetical to me. They’re about words, and the brilliance of words, and each sentence is really wonderful. Like Nabokov or…

Jenna: … Nin…

Rick: … Thomas Pynchon. Yeah, yeah. Anais Nin. I’m not that kind of writer. I’m going for this larger idea. Actually, I hate Hemingway, and I hate writers like that, but I’m actually finding I’m more like that. I want to express the idea and get it clear so that, I’ve transmitted that idea versus the beauty of the language.

And I don’t know. I’m not worrying about it right now. It’s fine. I want to just get it done.

If I have 6 books and all of them weren’t that good, then maybe I’ll worry about it then. [Laughs]

I think the act of doing is far more effective at making you better, than worrying about being good.

I personally would rather write 6 books as part of the process of getting good than obsessing over one.

And then it’s just like, I don’t know, the expectations are too high. I like low expectations. I like my really low book advance. I like doing a Kickstarter project where nobody really expects a lot because it’s like a dumb book about weddings. I like that, because it doesn’t paralyze me.

I think of Donna Tartt, and I would just lose my mind if I was Donna Tartt. You know? I can totally understand why J. K. Rowling used a pen name.

You get these expectations, it’s too much.

Some people are very good at that, but I’m not one of them. I would lose my mind if people expected too much from the art, so I just keep doing it and get it out.

Jenna: You’ve met a lot of people throughout these three decades, a lot of people. And a lot of them are your friends. What have you learned about the human condition from all these different conversations that you’ve had? Whether they be in work, or friendships, but you’ve talked to so many people, you’ve experienced so much, you’ve built a company, sold that company, you’ve consulted, you’ve run a record label, you’ve been in a band, you’ve done all these things…

What… what are people about?

Rick: [Laughs]

What are people about? I think people like to talk about themselves, right? They do. They’re very much in their lives. I think that’s… I don’t think it’s a bad thing. Like just even this. I’ve been looking forward for this for 3 days because I could shoot my mouth off for a while. It’s very nice. Right? I think that we…

Everybody has a struggle with anger and joy.

Everybody has this awareness that we’re all going to die… but we all have to make our own peace with that. I think that’s pretty interesting.

Those are sort of the common things about people. I think that there is a lot, an incredibly wide range of ways that people handle that.

When I was younger and my path through art took me through a pretty place where everything was really dark and angry. These artists, musicians like Boyd Rice and Death in June, and noise musicians, and really difficult filmmakers and… but there’s something that those people have that everybody else has and they’re just dealing with it in their own way.

I think that the struggle between the positive and negative is definitely in everyone.

No? You don’t think so? I think so.

Jenna: What else?

Rick: I think they’re more different than people think they are.

A weird tangent in my life is I spent a lot of time running sales departments and building sales departments, I’ve done a lot of different things. So I’ve spent a lot of time with sales people, they really believe that everybody’s got a common core. And I do think that’s true to some extent, but people’s motivations are so infinitely varied that… it’s hard to say.

Okay, we want to belong to things, right? In New York, in the business world, you got all these Ivy Leaguers, and you got these old families, and you got people that were in crew and they belong… and they really identify with that.

Then you’ve got the rest of us. And we need to belong to something else.

One of my best friends is a guy that we met in the internet world because we’re both just like weird music. That was our way to bond with each other in this world. People want to sort of belong to these groups, sometimes.

I think that it’s an interesting way to look at the world because… Yeah, I don’t know. But the reason… I was at four different interviews, where people were like, “You should go to college, not because you’ll learn anything but because of the network.”

I think that’s a single manifestation of the reason people join churches, and the reason people are into EDM, the reason people are racist, the reason… it’s all sort of comes from this place of wanting to feel like they’re in a group. It can lead to bad things and good things.

But this, I think that belonging is something most people strive for.

No man’s an island and all that. You got some people that freak out and hide away in the wilderness, but not many of them, right?

Jenna: What do you want your legacy to be?

Rick: You can’t think about that.

Jenna: So you’re just doing?

Rick: Yeah, yeah. Actually, I think about dying a lot. But I don’t think a lot about afterwards. I mean, I guess it’s probably the ego in me. I don’t mean the afterlife. I don’t think about the people that are going to be left behind. I know they’d be sad. I think about my wife, but I don’t think about the public. I don’t think about that. I don’t care about any of that. I really don’t.

I guess you think about your funeral, you’re like, I want people think “He was nice. We liked that guy.” But I don’t care about my body of work or anything like that. Do you? I don’t know, I don’t really…

No, I don’t.

You know what? Everything I’ve done when I’ve gotten good at it I’ve throw it away, right? If I cared about that, I wouldn’t have done that.

As soon as my band started getting people going to the shows, I was like, “Okay, well I get this. I’m going to stop.” As soon as the company did really well, and I’m like, “Okay, I get this. I want to stop.”

I don’t keep doing a thing once I sort of get the basics of it. That’s not the way you would act if you really wanted to master something or become known for a thing.

Even my best friends wouldn’t, couldn’t write a fake obituary because they’d be like “I don’t know. He did some weird business stuff, and he did some weird art stuff and he was a really nice guy.”

There’s no common thread because it’s just at different times there’s stuff to do, that I want to do, and then I’ll do something else later.

I actually worry about it. There’s been twice. When the Subservient Chicken got big, and when I was working at Tumblr. You started to see people identify you with these things. And it was really upsetting. [Laughs] You know what I mean?

I have a friend that… and now blissfully, people your age don’t remember Subservient Chicken, but he would always tell everybody when I met him that was like the thing I did. It made me so uncomfortable. I don’t want to be known for a thing.

I used to joke that my tombstone would say, “Accomplished much, but rarely before 10.” It was just sort vague. I think that’s a better way to go.

Jenna: Do you think that keeping in mind that we all die is a good way to make, to do things, to be someone that is fulfilled, or worth it or…?

Rick: Well, no. I don’t.

I do think it’s a way to be productive, and to find a place in society, and to not go crazy.

But really, the advanced-stage-pro move is to then find some peace with that knowledge of, we’re all just going to die and there no point to any of it and be able to just enjoy happiness once in a while.

The kids are back in the park that I walk through every morning because the fall has started and there was a youth soccer game the other day. I’ve been walking in this empty park all summer, and now there is all these families and I was walking through and just watching them and how much happiness… they’re just sitting there, watching their kids play soccer. I was like, “They got something going on with that.”

But you know, I only feel it for some milliseconds here and there. I feel there’s a long way to go to being in anyway, at peace. That is I think a big trick because lots of people … I’m now listening to the Marc Maron podcast. You hear this refrain from Wyatt Cenac, and Robert Rodriguez, and what’s his name? Gandalf. Ian whatever. Every one of them says the same thing. They’re like, “I just stayed busy because it staves off depression. I have to keep moving.” I think that a lot of artists are motivated with that.

The more complex thing is to keep that motivation and slowly find more peace about it, and find some happiness and let other people into that happiness without losing the productivity. And I do not feel like I’ve got there yet.

The other day I was like, “Whoa! I’m happy!” then it went away. It was like a second. I was like, “Oh, that was really uncomfortable. I don’t like that.” [Laughs]

But it’s enough to show you that there’s more to do it.

But you know what? Being afraid of dying and staying really busy and getting shit done is a great way to get your act together, right?

It really is. [Laughs]

Jenna: What do you see in the younger generations of people that are now graduating college or graduating BU? What world are they going to be in? Are you excited about that world?

Rick: Oh yeah. I’m totally an optimist about that stuff.

I mean, I did have a revelation the other day that… Not so much BU. I don’t really spend a lot of time thinking about my old school. But I’m on the board of the VCU Brandcenter, it’s an ad school. And at Barbarian and Tumblr and SoundCloud and Percolate, we have a lot college kids that like are either interning or are just new graduates. And I think they’re great. They’re all super smart and awesome and intelligent, and eager, and driven, and you know, I had a certain intern that was like that. It’s awesome.

But I do realize one day that those, it’s self-filtering. I have a kind of a warped view of your generation because all I do is see all of the hyper-achieving, happy, active ones, because the ones that are sitting around, thinking there’s no future are not interning at tech start ups really.

I think the world, it’s the whole sort of the “arch of history is long but it bends towards justice.” I think things are always broadly getting better, slower than people want them to.

The generations – I think the millennials are awesome. I don’t get rompers, but other than that, I think they’re fine. I think they’re smart.

I definitely like most of the internet outrage. I look at it as people just cleaning up messes that we need to fix. I really love that about the millennials.

They’ll be like, “Wait a minute so… you guys just let Bill Cosby still walk around!?” And everybody’s like, “Oh yeah. We should’ve taken care of that. Yeah, you’re right. Alright, let’s fix that.”

Any younger generation is the ones that come along and they’re like, “Wait a minute! Why didn’t you fix that thing over there!?” And everybody is like, “Well, we just never got to it… Alright, good point. Yeah let’s go fix that.”

And you guys are better than our generation was. Because our generation was like, “Wait a minute! So, we’re supposed to aspire to be a businessman and do a bunch of coke with Ronald Reagan? Oh screw that! We’re going to start slacker, stoner bands like Pavement.” And we just didn’t do anything.

The internet basically saved Gen X. Because then when the internet came along, we were finally like, “Okay, we can get into this. We’ll get some jobs now and we’ll go do stuff.” I’ve met all these musicians now that I listened to back then. We all just were like, “This is stupid.” While you guys are like “Right. We’re just going to make this better. We get this. We’re going to go make this even better.”

So I do like that.

But people cleaned up Bill Cosby, that’s nice. That was a thing that needed to be done. The millennials will just point out… like there’s a renewed interest in dealing with the gender pay gap.

When we came along, the X came along, and they were like, “Oh, that’s screwed. That’s still really screwed up. Oh well.”

And we just took it as evidence that the world was corrupt, and just learned to live in a corrupt world.

Whereas you guys are like, “No, we should really fix that.” I mean, X didn’t really dispute that needed to be fixed. They just didn’t think it was fixable.

Whether it’s right or wrong, I like that young people in general say, “Well, we’re going to go fix it.” Sometimes they can’t. I think that’s very much will happened to my parents, the Boomers.

They had the 60’s, and they had their anti-war movements and then they were like, “Oh that. That didn’t do any good. We just assassinated all our great leaders and still go to war all time, and the military-industrial-complex. Oh well, we’re all going to become Republicans.”

I think it’s great. I think that you guys… Our generation really failed in not inspiring society to be… We’re the gap.

The Boomers did it, and failed. You guys did it. TBD on whether is succeeds or not, X just… you know… I mean, you can see them all now. All of them, I guess I’ll include myself. But you can see people like Dave Eggars being like, “Oh, I should try and do…” He’s got his own non-profit. He’s writing interesting books about refugees, versus all of the navel-gazing we did when we were young. Moody music about how nobody loves us.

We were terrible. We’re a terrible generation, but we’re trying to make it better. I do think that, now, I think that’s the difference between us and the Boomers, is that they really went for it, failed, and got disillusioned. We just started disillusioned and then woke up and now we’re trying to at least make amends.

Jenna:  I have a question that I really hope that you’ll take seriously and answer.

Rick: Alright.

Jenna: What does a good world look like?

Rick: Well, one thing that’s… I cannot help but answer these things through economics because I think about economics a lot, and I do think that the income inequality stuff is a huge problem. There is multiple levels of it. There’s American income inequality, then there’s the globe, and that creates an inherent tension that makes it very hard for people to sort of remember… that there are other things.

One of the things I always do when I think about this question is that, you got to consciously think about the whole planet and let America as a concept, go.

Globalization is a really pressing horrible thing in it some ways and it’s doing some horrible things to Americans as manufacturing is outsourced. But it’s also brought millions of people out of poverty.

Everything has got a good and bad to it. And I think that a world that is just and good is one that has had that process play out in a way that has yielded some fairness for everyone. That everybody on the planet earns a living wage, that everybody on the planet is given a fair shot.

And to do that, we really, as Americans, have to accept that this isn’t going to stay this way.

I got like a millions of dollars in stocks, and I rationally know I shouldn’t have any of it. That it should just go.

I got my house, I got my art, I can afford to live on various low paying jobs these days. I make well under $60,000 a year now, and it’s great, and that everybody should have. And if that means that the millions I have in stocks were completely gone, that’s perfectly reasonable.

And I’m not even rich compared to rich people. That’s just got to get fixed. It only ever gets fixed through war, taxes or revolution. And I’d much rather it happened through taxes.

This guy Thomas Pikkety, do you know him? French academic, wrote a book last year about income inequality. He has a new readable version of it for the masses this year. There needs to be like a 90% tax on an income over a certain amount, stuff like that…

I think the health stuff we generally have in hand. You’ve got things like the Gates Foundation and people are really trying to make the world healthier, that stuff’s going well. We have the population growth in hand, and that’s going well. The thing we’ve really failed on is famine and income inequality. Those things are going to take some real… Then I guess global warming of course. Because you got to balance those two. We got like 5 billion people that are still poor that are going to stop being poor, and they can’t do the way we did it. So, that’s got to work.

But I think that were… That’s going to sound neurotically optimistic… But I think we’re getting better at global warming, slowly. I think that’s where it is. It’s income inequality, basic income, socialized medicine, stuff like that, that we just don’t… We don’t think as Americans are realistic. Like that’s gotta happen.

I mean, I wrote this essay about this on a lark. It’s funny because this is in the category of at risk of being famous for when I die, whether this is about Star Trek economics. On Medium, when my friend got a job there, and I was trying Medium out. This has just hundreds of thousands of reads on it. I get interviewed for it all the time.

But one of the reasons I did it is for this reason. They painted this picture of how… I tried to sort of tie the economics of it to real economic thinkers, of real movements and show that there is a path towards a just world, where everybody is given an equal opportunity. I do think we could get there.

I think that two big problems are income inequality and global warming. It’s up to the people on the planet now to fix those two.

But then you know, there’s a… My friend Doug introduced me to this book called First and Last Man by Olaf Stapledon. It’s a sci-fi book, but it looked at the history of humanity. It read as a historical document from the future. But not like a hundred years, like 20 million years into the future…

All this, it’s an interesting time. When I was young, I was really upset about dying. I would think about this a lot. We’re kind of the last few generations that are going to be mortal in the traditional way.

There’s advances like Ray Kurzweil thought he’d make it, he’s not going to make it. But in another hundred years, we are conquering the medical issues that make humans mortal.

We’re going to have to answer some big questions around like, “How many people should we have? Do we really…? What does it mean to be human? Do we want the machines to be in charge? And do we want to be in computers, or do we just want to stay this way?”

I think especially for people that have been blindly techno-utopian, like I was when I was a kid, they have some difficult questions to answer. They weren’t really important up until soon. You could worry in the 1800’s about the AI revolution, it didn’t really matter. You would not be rational to spend your whole life worrying about that in 1809. But it’s not completely crazy now. That maybe society eventually will be like, “Nah. K. That’s enough tech. We’re good. Let’s pull back.” Or maybe we like move into chips, I don’t know. We don’t know.

But in the interim, we got to fix… just give people an equal chance. I guess perspective matters on that too. But we’re not, I’m not going to be there for any of this, so, it’s not my problem.

You might be. I’m just kidding. [Laughs]

Jenna: Thanks. [Laughs] …

Advice.

Rick: [Laughs] I don’t like giving advice.

Jenna: No I want you to give advice.

Rick: I wrote a really long article on not giving advice.

Jenna: I don’t care.

Rick: That’s another reason I write books now, is because I’m like, “If you want advice on this one topic, here’s everything I have to say on this one topic.”

Jenna: Right.

Rick: But I don’t really like going around telling people what to do.

Jenna: All right. Fine. Um…

Rick: It’s interesting.

Jenna: Yeah, not telling…

Rick: I like getting it from people.

Jenna: Yeah, not telling people what to do but the best advice come from people that you respect. A lot of people respect you for a lot of legitimate reasons. So, asking you for advice is not… Yeah. Okay, great. Logically speaking, you can only write one book in what time period so?

Rick:  Once a year, maybe.

Jenna: If you had to answer, what are some really important things for people to know?

Rick: Well, think about this though, think about for the benefit of our listeners, our conversation earlier where I was giving an ode to the person that lays low at a company and avoids the politics and just stays there quietly for 5 years…

Jenna: That was you, wishing that you were that person for a split second.

Rick: Well, this is my point though. It’s like, those people are doing what works for them. Right? I can’t tell them, “Well, if I were you, I would storm out and…”

Jenna: Advice is not ‘If I were you’, advice is, “Here’s what I have learned, and here are some truths that I hold dear, that I think can apply to no matter what life situation you have. This is… this is something that I think is true.”

Rick: But people are usually asking about a specific situation, right?

Jenna: All right, fine. Work advice.

Rick: Yeah, right. I guess, actually larger life advice is easy. I mean, everybody, just be nice, assume positive intent, be kind to others. We can all do that. That’s easy.

Jenna: All right. So what’s hard?

Rick: When somebody is like, “I don’t know what to do with my job.” I’m like, “I would’ve quit.” So I can’t really give you advice because I just quit jobs all the time. I’m really bad about that. That’s not good advice. Although I did that to you and you did it. So hey, high five! [Laughs]

Jenna: [Laughs] All right. All right, all right. Advice to someone who will be listening to this.

Rick: Well, so yeah, we’re talking about art and good. I did find that… I find right now, that worrying about whether your art is good or not is a blockage for me and that I would encourage other people to give it a shot to just try and produce.

That’s not to say I don’t think there are people who I really respect their art that spend a lot of time meticulously crafting it. But right now, I’m really into that approach.

Do you know Brian Eno’s “Oblique Strategies?”

So there’s this card deck, I’m about to do a project with him. They’re cards that just have words on them for when you are stuck, like, ‘clean the studio!’, or ‘think about…’, or ‘look up!’, or ‘think about this’.

It’s to encourage you to think in a different way.

One of those for me now, would be just “don’t worry about good, just get it out there.”

Jenna: So, just do.

Rick: Yeah, just do it, yeah.

Jenna: Always do. [Laughs]

Rick: Oh God I can’t believe I just said that. [Laughs]

The other thing I’m really big into now that I would encourage people is completing stuff.

I have a really good friend that has the best ideas in the world and never completes any of them. He just needs to pick one and just do it, and complete it and do the next one, and complete it.

I had this problem for a little while. About 2 years ago, where I was… I had this idea that was like “everything” in one. It was so complicated, and I was so into it. And I was like “I could totally do this, I only need $20 million dollars and, it will save the world and it plays to all my strengths,” and I was just like, “That’s just like a stew.” I just put everything into one thing and came out with a thing. It doesn’t really mean anything. That’s not… No, let’s just pick a thing I can actually do and go do that one.

I think people get stuck on that a lot too, at least in the art on the art side.

I would not say anything along the lines of… I really, find it really tedious when artists are like, “Just go, and go do your thing, and chase your dream. And don’t worry about money and blah, blah, blah.” I find that super tedious.

We have to make a living. We have to earn money. I don’t know if you’re rich, you don’t, but most people do. They have to find a balance between art and culture that works for them. And I don’t think there’s anything wrong with that.

My wife and I were talking the other day. There’s this ad guy in New Zealand that died recently. Did you hear about this? And he had cancer, and he was… I’m not quoting this exactly right but he basically had this epiphany. He was hanging out with his old colleagues and he was like, “None of this matters. I wish I had realized earlier it didn’t matter” because all his colleagues were going on how they work too hard, and they cared so much about this advertising. I was like, I thought it was all just kind of like you know, this guy is dying or dead. So I feel bad about saying this…

But I mean, first of, what you didn’t fucking know this about advertising? The fact that the world has a field that exists so that you can make some money from writing and making movies, and photography, and getting paid to do it instead of taking out the trash, is kind of awesome. Did you really think it was everything in life? No. It’s an industry that certain skills sets can make some money in. I think that’s kind of awesome.

I really find it super tedious when people look down on money and look down on things that involve earning a living, at least. You’re not going to be super wealthy or anything, but I think that’s cool that there’s multiple fields like that.

I had a friend that was a librarian. She freaked out and went to Hollywood. And now she’s like a costume designer on some of the best Oscar winning costume design projects. That’s awesome. She also does like some crappy TV stuff, but so what? She just did it. There’s this whole billions of dollars industry out there for people that want to sew for a living and make costumes. That’s awesome.

I don’t know, I think people get too hung up on purity of it all. I don’t think there’s… That’s not worth it either.

There’s no purity in art, just make shit.

If you’re paid by some weird person, that’s cool.

It’s not like brands are the greatest things in the world, but sometimes they give us money.

I just reread No Logo by Naomi Klein, and somewhere in the book she’s like, ”I should pause for a moment here and also say that for everything I’m telling you about how awful brands are in sweat shops and globalization, also brands have donated millions and billions of dollars to the arts communities around the country and it’s kind of amazing and awesome.” And I thought it was hilarious. It was just like, “Okay, I do have to admit this” And I was like, “Yes.” Yes. Things can be good and bad, whatever. I’m rambling now, but…

It’s okay to worry about money once in a while.

Jenna: I’m done.

Rick: Oh great! Bye little microphone.

Jenna: [Laughs]

_____________

Thanks for listening to NOD episode 005 with Rick Webb.

Follow him on Twitter, Instagram, and Tumblr. Buy his book titled Agency: Starting a Creative Firm in the Age of Digital Marketing, and support his Kickstarter for his new book Man Nup: A Groom’s Guide to Heroic Wedding Planning.

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Until next time. In the meantime, always do.