Tiffani: Well, so, one thing that I want to ask about, which is kind of total off-the-wall, is, like, I watch a lot of “House of Cards,” and I saw your name in the credits. What’s up with that? I’ve never, like…

Cathryn: Wait, legit? That’s a thing?

Tiffani: Yeah.

Harper: Yeah. I was a consultant.

Tiffani: Yes. I just happened to see you when I was watching one night. I was, like, “Wait a minute, that’s, like, him.”

Harper: Well, a friend of a friend connected me with Beau, the guy who made “House of Cards,” and we just started chatting about various, like, political things. And then he was like, “You should talk to the writers’ room.” And so, then I just started talking to the writers’ room, every once in a while. And it was interesting because my contact in the writers’ room was this guy named Tian Jun, who was one of the writers on “House of Cards,” who’s, like, the youngest and maybe only…I don’t actually know if it’s only, but person of color in the writers’ room.

Tiffani: Oh, wow.

Harper: And so, he’s like, this guy who is just like…we reached out, or reached out to me, and we started getting this good repertoire of he would pitch a lot of really interesting tech things, and I’d be kind of, like, his sounding board, to try and make sure they sound…they were somewhat realistic.

Tiffani: Nice.

Harper: Not that, like, movie OS “Jurassic Park” type of like, “Oh, UNIX, I know this,” type of situation.

Tiffani: Right. Or like, no, we think about what, like, Kelly Rowland texting in Excel that’s on the video.

Harper: You know, so it’s like, you always have to kind of be careful with that type of thing, you know, and so a lot of it was just about…was about doing that. Like, there’s, like…just making sure… But it was interesting because I’ve never been involved in Hollywood, let alone, like, talking to folks that are involved in Hollywood, and the whole idea of having a writers’ room is interesting, you know? It’s something where you have this group of people that are, theoretically, guiding this entire thing, and you just kind of talk shit for a couple hours, hoping something comes together, right?

Harper: It was so interesting, and I’d just sit there. I was this kind of strange expert on technology and somewhat, like, and campaign politics, or campaign tech, and I would just be…they’d just say like, “Is this…could this happen?” I’d be like, “Well, you know…” Like, for instance, it was like, “How could you…could you hack a phone?” And the problem was, is all this shit is like happening in real life.

Cathryn: Right.

Tiffani: Right, so…

Harper: It was like, you know, those, like memes, where’s it’s like life comes at you fast?

Cathryn: Yes.

Harper: That’s how I felt like that experience was. Where it was…we’d be…I’d be like, “Well, this is a crazy idea,” and then you’d, like, look at Twitter, look back, and be like, “Well, it’s happening in real life now.” You know, that type of thing.

Tiffani: Not so crazy.

Woman: Edit.

Tiffani: No, yeah, I mean, that’s amazing because, because, like I said, I saw that. I was like, “Wait a minute, that’s…” because it was like, buried in the credits. And I’m the person that watches the credits because I don’t have anything else to do, but… But yeah, no.

Tiffani: But that was not a hidden scene. She wasn’t, like, waiting for a secret Marvel universe scene…

Tiffani: Yeah. Because you’re like…the way the credits are setup, it’s like, you know, consultant, and it’s just your name. It’s not like a long string of names afterward, or whatever, so…

Harper: Oh, really?

Tiffani: Yeah, it stuck out. It stuck out like that.

Tiffani: The one consultant.

Cathryn: Right.

Harper: It’s kind of cool. I mean, it’s cool… I’m proud. I have an IMDb page now and everything.

Tiffani: Oh, wow. Yes, yes.

Harper: Every once in a while… You know, I got that, the moment they were like, “Yeah, you’re in it.” Someone’s like, “Yeah, I saw you in the credits.” I was like, “Just a second.” You know, I check my IMDb page.

Tiffani: That’s great.

Harper: So, my whole goal, in life, right now…this is not my whole goal…one of my goals in life is to get a Kevin Bacon number, a valid Bacon number.

Tiffani: Oh, yeah.

Harper: We’ll have cons, screens, and, like, the movie. That’s one of my goals because I want to have a Bacon-Erdos number.

Tiffani: Okay, all right.

Harper: Paul Erdos has that, you know, the math papers where you get your Erdos number seeing how close you are, there’s this kind of Erdos network. I just want to mix…I want a Bacon-Erdos number. It’s a small group of people. I just want that for my Wikipedia page. It deserves that.

Tiffani: Oh my god. Are we going to need to, like, calculate this for you?

Tiffani: Life goals. These are things he’s looking for. Let me pause, I just want to make sure Harper that, like, when you’re talking, we’re getting everything.

Cathryn: All right, we’re back. And we’re back, Harper and Tiffany.

Tiffani: All right. I guess my next thing, obviously, is the Obama campaign and how you got involved in that and, like, just I guess I have been impressed in reading just kind of the back story of how the campaign worked and all the software that was there and all the stuff that you enabled people to do, like, through that. Like, a big thing I’m getting into now through the organization is this community organizing. And you guys kind of took that approach in the campaign but you, like, turned it into software how it worked and got regular people involved with stuff like that. What was that like? And, like, how did they kind of come to you and say this is what we want and that whole experience?

Harper: Well, it’s kind of funny. Let me think the easiest way to say it. So it’s pretty unexciting. Is that a real word? A lot of people that I worked with when you talk to them, you said, “How did you get into politics?” They’d be like, “Oh, my father was a Senator.” Or, “When I was eight, I volunteered for my first campaign.” Like, for me, I basically just met a guy in a coffee shop because I didn’t have a job. I mean, it wasn’t so basic as that. It was pretty basic.

Really what happened is, a friend of mine, I didn’t have anything to do. I was, like, kind of thinking about building a startup. I was kinda laying around and a friend of mine was like, “You know, you should talk to this dude, Michael Slaby. He needs some help with a project.” And I just went and, like, met him at a coffee shop and he was like, “Yeah, I need some help.” I always believe that…or I try and do this every couple of years, is take some time off and spend a lot of time helping.

So I’m talking to start-ups, and when someone says like, “Can you help in this regard,” figuring out a way to help. And I always comes with some rules like I don’t want deliverables but I’d do anything. You know what I mean? Like, I’ll make calls. I’ll do whatever you want but I don’t wanna actually have to go home and do work. Like, I don’t want to do contract work. I wanna help in a way that I can help using my network or maybe, you know, strategy, whatever. But I really like to help if I can. And so between 2009 and 2011, I spent a lot of time helping Chicago startups. I spent a lot of time traveling and trying to figure out, like, how can I participate. And I also, theoretically, was trying to start a company although I was pretty bad at that.

And then when Michael Slaby who is the CTO in ’08 was like, “Yo, you wanna help out?” I was like, “Yeah, of course.” So they were looking for engineers and they were looking for a CTO candidate and they were looking for all sorts of people. And so that’s when I was like, “Yeah, here’s a bunch of engineers. Here is a handful of CTO candidates that I think would be great in addition to a bunch of friends.” And just generally kinda pushed a lot of, like, general, like, here’s how you build engineering teams, a lot of those ideas. And then in a very kind of Dick Cheney sort of way, I realized that I was actually being interviewed for CTO. I totally did not intend that to happen. And so just kind of one thing led to another, but it really wasn’t… I did not mean to. I mean, I did not intend to. I didn’t wake up one day and be like, “You know, I wanna be a CTO for a presidential campaign.” I never really wanted to work in politics. But I did find that it was a really remarkable experience and I quite enjoyed it. Just a second. My dog has a marker.

Cathryn: Do you need to go get it?

Harper: Yeah, I think so.

Tiffani: Go ahead and get it.

Cathryn: That’s important.

<insert side conversation about aging>


Tiffani: No, I mean, I guess that’s an interesting thing to talk about though too. Because you think about, like, I just read something last night talking about how IBM, it’s a “Pro Publica” writeup, how IBM has been secretly been, like…I guess, not secretly, like, firing all their older employees or whatnot. And I guess, I think, interesting thing to talk about was, like, you just turned 40, how do you…I mean, I wouldn’t say you’re shielded from the effects of, like, age in this industry but, like, I don’t know. I imagine a lot of people at the event will be in their 40s. What kind of thoughts can you give them? Because I think about stuff like that with, like, IBM firing people that are, like…they wanna stay over the hill. And the report was saying that some people, like, had to train their younger replacements even. You know, and so…

Cathryn: Ageism is the whole thing.

Harper: So I think Ageism is a thing and I actually… You know, I don’t think that I am outside of being judgmental on someone’s age. It’s interesting because I think I go both directions. If I have three candidates in front of me, my bias is probably not gonna pick the youngest one and probably not gonna pick the oldest one is my personal bias. And so how…

Tiffani: How do you even acknowledge that?

Harper: How do you protect against that, you know? Because I’ve had this challenge a bunch of times. A couple of people we hired on the campaign were well in their 50s. These are just tech engineers. One of them, like, invented [inaudible 00:08:28] code load. So it feels like, you know, he came very highly recommended but he was totally not the prototype engineer that I would have expected especially, you know, you think of like this…you know, we joke a lot and we try not to build that culture of, like, let’s go crush some code. But then at the same time, you know, when you’re running a small company or you’re running a a really intense project, you really just need to go crush some code.

So you’re trying to do it with, like, hugs. You’re trying to do it with this, like, nice comb. You know what I mean? You’re trying to do it in this way where you’re like, “No, I wanna crush code in this nice positive, you know, positive way,” but at the end of the day, you’re just trying to extract as much value from people in this room with you at the same time. And I think you’re trying to do it with your values, you know. And so it was really cool to have this dude who just was completely different than everyone else. And he kind of made… In my head, I saw him and I thought, “Yeah, I don’t know.” And then he sits down and he does a bunch of stuff. And I’m like, “Yeah, now I know.” And I was wrong. You know, those experiences, you know, I’ve talked about this before, those experiences, being wrong all the time have helped.

Because it’s like this thing where you have this bias. And maybe you can acknowledge the bias, maybe you know the bias. But that doesn’t mean that you stop acting on the bias. Just being able to say, like, I have a bias doesn’t mean that you actually change anything. I think you have to have those experiences that kind of fuck with you. Those experiences that are constantly in your face being like, “Yeah, you have this bias still, and it’s still wrong.” You know what I mean? Because what happens is it’s easy to just take a Stanford quiz and be like, “Oh, this is my biases,” or whatever, and then we all go on and we live our life and then I’m still, you know, hiring only white men or whatever. But it’s really that experience of seeing this person who sits way outside of my expectation and seeing them doing much better than people that sit in that expectation and then just being like, “Oh, fuck. I am wrong. I am really wrong again, and I should not stop listening to myself, sort of.”

Tiffani: Yeah, no. That’s amazing. I mean that’s an interesting admission because a lot of people will not, you know, I guess, publicly say that they are wrong and they’ve been wrong and… I guess, it’s interesting to kinda hold the two thoughts in your head. Like, I know I have this bias but I’m also wrong and so, yeah. That’s great.

Harper: Well, there’s a… I think it’s also, like, a position of power. It’s easy for me to say that, right?

Tiffani: Yeah.

Harper: Because if I admit that I am wrong, it’s not like I lose money or I lose success or anything else. It’s easy for me to admit I’m wrong. But, you know, if you’re someone who is still trying to make it, you still have to seem like this super-person. You know, you still have to seem like you’re impenetrable, like you’ve never made a mistake. You know, you’re going to talk to a funder or an investor, you have to seem like you’re the best person in the world for ever and ever and ever. And I think that sometimes we forget that we really want people to be honest and human, especially in tech where there isn’t honesty, there isn’t empathy, and there isn’t humanity, that we want those people to be that yet we don’t have room for people to be fallable. And I think that’s something that… You know, I think that’s empathy actually helps out a lot. You know, the other thing is, like, this is a safe place, right? Like, if I’m sitting there with a bunch of folks…

Tiffani: What is? What do you mean?

Harper: What?

Tiffani: What is a safe place?

Harper: Like, the three of us. You know, like, I know if I said something really fucked up, you guys would look at me and be like “Harper, that’s really fucked up.” You know what I mean? [inaudible 00:12:25]. Yeah, you just said it. I’d be like, “Hello, hello?”

Tiffani: It’s time to go.

Harper: But I know that there would be a dialogue, you know, so I can say things that are a little more honest. Then I think that I think we have to give people an opportunity to say that they’re wrong. That doesn’t mean we get an opportunity to try and prove to us that they are right. That’s different. And I think that’s where sometimes when on the internet it gets a little like, “Have you thought about this?” And I’m just like, “No, shut up.” I’ve not thought about that, I’m not gonna think about that and I’m just going to…yeah, that’s when I shut my laptop and I go outside or whatever. That’s not a lie. I shut this laptop and I go to my workstation where I can go to a different laptop, you know. [crosstalk 00:13:16].

Tiffani: Different laptops are all around.

Harper: So that way when you are done with one conversation, you just shut it and you go [crosstalk 00:13:19]

Tiffani: I do that. I have my pro-book and I’d be like, “All right, that’s enough of that.” [inaudible 00:13:25]

Harper: Chromebooks are the best computers by the way.

Tiffani: They are. They are. Google sent me one for free to try to get me to use their AMES [SP] thing, and they never called me back though. So I like got a free laptop. It’s like, oh. It’s like convenient and like…

Harper: Yeah, it’s real nice. It’s real nice. I’m glad that worked out for you.

Tiffani: Right.

Harper: I paid for the last one.

Tiffani: Oh, I’m sorry.

Cathryn: The last one. Oh, there’s room in there.

Harper: Yeah, see.

Tiffani: What do you mean?

Cathryn: He paid for the last one so he’s had…

Tiffani: Oh, the last one, oh, there’s another one, okay.

Cathryn: That’s how they do it. They get you hooked and then like, “All right, you know, you buy that up.” Harper, do you have questions for Tiffani?

Harper: I do have, I have a couple of questions. Okay, let me pull up my questions list. I got 35 questions here.

Tiffani: Oh, God.

Harper: Okay, okay. So they’ll be simple. The first one I have two questions, first one is your project is non-profit, right?

Tiffani: Yes.

Harper: So but you started a company that was for profit.

Tiffani: Oh God, yeah.

Harper: I’m throwing out some deep cuts here…

Tiffani: Yeah, you did some research. All right.

Harper: What happened to that domain?

Tiffani: What? The other one?

Harper: pencil.in.

Harper: It doesn’t resolve.

Tiffani: I got a whole back story back here. Yeah, no. I mean it was an exercise in starting something that I thought was really cool and useful. But also, like, I think I treated it more like an engineering problem than a sales problem which is what it should’ve been. I was too enamored with “Let’s use React now. Let’s do this,” versus like, “How about you go get some customers and, like, figure out like who else can use this besides like your own personal stylist?” So, I mean, it was an online booking system I built called pencilu.in. And, like, I was on CNN and all the sort of stuff for it.

Harper: I know right, you would never have known.

Tiffani: Yeah, I don’t talk about it, because it’s one of my like quiet failures, because like…

Harper: But you raised a little money?

Tiffani: No.

Harper: No?

Tiffani: Besides like family, friends and family, that’s it. So friends and family like…

Harper: Then my question is sort of about this. My question is very specifically, how and why did you make the decision, after you’ve played a little bit with for-profit, you saw that this could be a thing, you got some people looking at you being like, “Oh, this could be a thing,” then you were like, “Let’s go to non-profit.” I wanna know about that transition because I think that is an important transition that more of us should be thinking about.

Tiffani: Well, okay. So, I mean, the previous for-profit just didn’t do well. And it got into a… I think it’s useful to kind of, like, separate yourself from your work and I was kinda not able to do that. So I ended up real sick at some point, stressed out. I thought I had ulcers and all sorts… I was in the ER all the time and it just got to be a really, like, not good thing. Because I just didn’t have at that time the ability to evaluate from a business perspective and really understand like what truly should’ve happened until, like, a long time later. But I mean, like, I moved here and, like, started an organization Code for America and then…

I mean this project, this whole organization grew out of being a side project there. Like, it was not my fellowship project and I just happened to read about what happened and… But I think I like it a lot because it allows me to still use a lot of the same tech skills that I would at for-profit. Like, I still use a lot of the same stuff, AWS, all that, whatever. It’s written in rails and all that sort of stuff. We got funded by YC and… It’s to say I just won’t be rich from it but I don’t feel like it’s any different from anything else that, like, runs from around here basically. But there is a demonstrable, like, benefit to people that actually exists from it. I mean, I never thought about the transition, I guess, because it’s more like it just happened kind of, I guess. I hate when people say that on talk shows. “It just happened.” But like…

Harper: Here we are on a talk show.

Cathryn: Yes. The Tech Superwoman Talk Show and it just happened.

Tiffani: Yeah, no, yeah. It just happened…

Harper: When you woke up one morning and you were like, “I think this is gonna be a non-profit,” was there… Because you are in San-Francisco which is not a non-profit type of city.

Tiffani: No, it’s not.

Harper: That’s what I’m kind of, maybe that’s what I’m needling at, is how do you exist in San-Francisco?

Tiffani: So, I mean, most of the VCs that have given us money are how I exist basically. But I mean, so I remember having a conversation. Jim Palkus [SP] has been at CFA temporarily. And I remember him sitting with me one time in a conference room and I just kinda talking about the economics of what we were doing. And it’s like it’s not gonna be a for-profit, you know, as far as like scale-wise and what a VC would want. And, like, I also feel very strongly about the expectations that are had upon you when you take VC money. So it wouldn’t have been like a truly… I don’t wanna say it would’ve been like, “How can we scalp these people kind of thing.” There would have been different expectations basically that, like, you know… I think about HandUp for example, and not in a bad way but like they try to do something with homeless people here but they were for-profit venture basically. And from what I was reading, I got a sense that their economics didn’t work for them. And so they had to shut down basically. I think they sold to a non-profit that was in, I think Michigan actually. But their economics…

Harper: What was that called?

Tiffani: It was HandUp.

Harper: HandUp. I thought you said Panda at the time, and now all of a sudden [crosstalk 00:19:30]. And I was like, “Well, I mean I didn’t know that started as a non-profit…”

Tiffani: No, right. No, yeah, no kidding it was like a theme song.

Cathryn: Yeah, that’s another thing.

Tiffani: No but, you know, they tried to do the whole for-profit social good thing, but they took VC money and it didn’t work economically. Because, like, you know, VCs want you to get to scale quickly, they wanna see how…

Cathryn: Profitability.

Tiffani: Right. Profitability and they wanna see how they get their money back in a short period of time. And nothing that we’re doing really, like, is gonna facilitate that. It’s more about, like, the mission of helping people and getting folks water turned back on and raising money through crowdfunding for all that. But there’s no… There’s nothing attractive to VCs besides like the tech for good angle. Because, I mean, we still use a bunch of data and all that sort of stuff but there’s no like, “Oh my God, you’re balance sheet looks amazing.” There is nothing like that that would make them seem, you know, excited about it.

Cathryn: But your helping human sheets is off the chart.

Tiffani: Right. That’s amazing but that’s not gonna sway somebody down in [inaudible 00:20:42]. At least not in the sense of, like, wanting to invest in it in that way but plenty of people give.

Harper: So then running a non-profit in California, how did you choose Detroit?

Tiffani: So I read about it. Like, I literally read in the Atlantic about what was happening to people. It’s an article that I saw on twitter one morning and I was like, “This is some of shit that this is happening to people,” because the headline for it was something about, like, this is what 100,000 people have to experience when they’re about to be shut off or something like that in Detroit. And I was like… So I was in Atlanta working in City Hall at that point. I was like, “Something really had to have gone wrong for people to make a decision that, like, yeah, they’re poor. We’re also gonna turn the water off. We don’t care. They owe us money.” And I just found that kind of curious and weird and, like, wanted to just give some money basically. And so Detroit, I mean, it happens all over the country but, like, Detroit is were the most acute need is because they had like the UN come in and all that sort of stuff, and, like…but they still don’t do anything different. I mean, and that’s kind of one of… What’s that?

Harper: It’s fucked up, right?

Tiffani: Right. It is totally fucked up. And it’s just like… Yeah, that’s how I chose it basically. I can ramble for a while but that is how I chose it.

Harper: One of the things that I’m very interested in is these bail bond funds. And there is this thing which is like…you know, the bail bond funds are so ad hoc. They are just this amazing ad hoc networks people asking for a little bit of money from a lot of folks in their, like, very private network. Typically, it’s a PayPal account. You know, it’s usually some person kind of doing it. It’s just this amazing amount of trust which I just love when we have this kind of… It’s just an exhibition of, like, trust. Like, we have such a fucked up world and yet we have all these little pockets where you’re like, “Oh, this is trust and empathy rolled into a little ball.” And it’s great but did the paying people’s water bill start in an ad hoc way like that?

Tiffani: Yeah, it did, because it was just me originally and Kristy Tillman that wanted to just pay some bills for people. And there was no, like… There wasn’t a process for finding people originally. Like, we just threw up a website the same night I read about everything. We even had it where like it was a Google spreadsheet on the front page of the website to try to, like, find people to sign up for it. Your name would be on the list basically, but like it transitioned into being like more people wanted to give than signed up because we were doing everything web-based at that point. And so, like, there were no people signing up to get help, but yeah, it was totally ad hoc. It’s funny, me and Kristy talked about this a long time ago, like how far we got with being like that. Like, there was no goal originally either for doing anything. There was no numbered to reach, there was no like, “We’re gonna help these many people and then stop.” There was no…there was nothing. It was just a matter of like, “Okay, we have the time. We wanna help people, so let’s just do this.” And it was a lot of dming basically. That’s how a lot of things went down. Like, this is the way it goes down in the dm.

Harper: And every time it comes on I’m like, “Yeah, that’s right. That one thing went down in the dm. Oh this thing went down in the dm.”

Cathryn: It goes down in the dm; it goes down in the dm. Yes.

Harper: I feel if I was Twitter, I would just shut down Twitter and just open up an instant messenger.

Cathryn: Which is what it was originally, it was supposed to be public text messaging which is why it was 140 characters.

Tiffani: But they should do that because a lot stuff happens there.

Cathryn: Dear @Jack. Would you do business with him?

Harper: I wanna dm them right now. I’ll be like, “Shut all this crap down.”

Cathryn: Just do the dm. Call [it] dm.

Harper: Tiffani, I got…maybe I have a couple of more but I could just keep asking questions because I’ve known you on Twitter for so long and it’s been fun to see this project grow, and it’s just been nice. So it’s really exciting to sit here in front of you and ask some questions.

Tiffani: Thank you.

Harper: So I have theoretically quit my job. I am without anything to do. I am, you know, a prototypical tech bro.

Cathryn: Is this theoreticall person 40 and awesome?

Harper: Oh my God! I am 40 and awesome, has cool glasses, all this stuff. Anyway, this theoretical person convinced them that they should do a non-profit instead a for profit company.

Tiffani: You said over a for profit?

Harper: Yeah, because here is the thing. I think that there’s this need that we need to figure out how to convince all of these folks out there. Someone told me the other day, “Look, in San Francisco, there’s a lot of founders. There’s not a lot of entrepreneurs.”

Tiffani: That’s true. That’s very true. We need like a fire emoji across the street and like

Tiffani: Right.

Harper: The thing is I think that what that means though is being an entrepreneur is hard though because there’s a lot of things you have to go through to get it done. And I think one of the things that we’re doing that is a disservice to all of us who are either wantrepreneurs or entrepreneurs is that we are limiting the scope of what we could do. I wanna open that scope up to include non-profits for some of these folks that are looking for something to put all this time and effort into. And so I think that there’s a pitch there that you, someone who has sat on both side of this, done for-profit startups and done a non-profit startup and you’re funded by some of the best in the business, YC, etc., like, you’ve checked all the boxes that most of these people who are wanting to be an entrepreneur so bad would love to check. Yet you chose non-profit.

And I think that’s so awesome but I think there’s a story here to say like here is why I did this and hopefully you can convince people like me to follow in your footsteps. So what’s that pitch? Or maybe it’s a book or two you’re going on it. And this is your talk. I don’t know. There’s something here.

Tiffani: I think about in terms, so, like, I was recruited by Facebook very heavily once upon a time. And I ended up there at the office and I just kind of wasn’t impressed. You know, I think about, like, I’m able to use all these skills I have now to, like, have serious impact on regular people. People that I think about the VC Anna Wimblarge. She’s like, “You know, go where the wallets are.” I go where the wallets aren’t on some levels but, like, you know it feels better to do that. Because unlike, you know, my work has impact on everyday people in a positive way that largely can’t be explained like certain social networks at this point.

You know, and it’s like there’s a tangible impact on people that you can go home and say that like, “Yes, I, like, spent the day on Stack Overflow trying to fix some crappy code that I wrote, but when I fixed it, 80 people got water this month. Like, 80 families got water this month.” Or, you know, I don’t know. I had a friend that like built a tweet bot to help, like, pets get adopted. So, you know, it didn’t turn into a whole organization but there’s all these little things that you can do with all these skills that you have that actually impact everyday people with regular problems that are not “tap and fetch it” apps. And I think that for me personally at least is why I do this because I’m like I get to do everything that I like to do.

I started off as a programmer but I like actually talking to people. So I like seeing the effect in my work. I like being in the numbers, and, like harassing our accountant. I like, you know, talking to people and going to events and speaking and stuff like that. So I get to engage all my talents and then at the end of the day, I can say this is what the end-result was. So I guess that’s like my pitch. Like, you can just impact regular people who are super-duper grateful for you, and, you know, some people are really moved by, “You’re a what? You do what? You’re a programmer? You, like, built this thing?” They are really moved by that versus like, you know, you working on some problem like ads or whatever. Like, they have their purpose or whatever, but, like, I just think that the ability to, like, impact regular people is a really, really powerful thing.

And, like, some people think of, like, tech as a super power. That’s a superpower. I’m talking about the whole superwomen thing. Like, the ability to actually impact regular people with code that you write every day in a really positive way that’s tangible to them, and in some cases lifesaving depending on what you’re actually working on, I mean, that’s powerful. That’s worth sitting through horrible calculus classes and like, you know, engineering classes you don’t wanna take and all that sort of stuff. That’s worth all that.

Harper: Do you program computers every day?

Tiffani: Not every day but, like, at least once a week I’ll do something with the real stuff. I don’t write code as much as I used to because I think it’s not as valuable as it would have been like a long time ago. My value is better spent, like, time is better spent like fundraising or like, you know, doing other stuff.

Harper: Did that transition feel weird?

Tiffani: Yes. I had to go talk to people over it. I had to go talk to people over it. Like, I had Sam at YC. Like, I just like, you know, emailed him one day and I was like, “You know, you’ve been like the engineering person and then you’re, like, a manager now. You don’t write code anymore. What was that like?” So he kinda like sat with me for like an hour and a half and, like, just kinda described… Because I was asking him about, like, you know, going from being a developer to a manager, what should I expect? What should I do to like… Because when you’re a developer, you’re used to just kind of sitting in front of a computer on your own, and you’re an individual contributor. And then like as a manager, you have to like start actually like getting stuff done through other people, which is like… I’m still struggling with it on some levels because, like, I struggle with delegation, for example, because I’m like I can just stay up at night and do this versus, like, handing this somebody else. But I’m like you’re not actually helping people by doing that. So it’s a struggle still, but it’s something I’m slowly but surely starting to, like, get a hang of.

Harper: I think that was a good pitch. You got any other questions for me?

Cathryn: Closing, closing question.

Tiffani: Oh no. I don’t know. I don’t know. I’m just kind of in awe talking to you two actually. I’m serious. Like, I mean, so what are you doing now though seriously? Because you have, like, your one company that you were doing.

Harper: Well, I sold that company to PayPal a few years ago and then I no longer… My last day on PayPal is April 2nd.

Tiffani: Okay, that’s super-duper close.

Harper: And then, yeah, a week. Then I’m done. That project is over and I get to figure what’s next. I mean, I…

Harper: I wanna build something that is impactful. And there’s been this, like, kind of trope going around a little bit on Twitter that you shouldn’t get addicted to, like, success. Like, there is a thing where people are like, “You should be addicted to doing good things. You shouldn’t be addicted to, like, this kind of monetary or reactive success, startup success, unicorns, etc.

Cathryn: Sounds like people who have money. Sorry, I had to say it. No, those are people who have money. You shouldn’t be addicted to having a pay check.

Harper: I’m not worried about it too much. What I was gonna say is that for me, I have a worry that I might be addicted to the 2012 Obama campaign. And so I worry that when I go out and do something that’s next, that I’m looking to fit and to, like, tickle that part of my brain. And, you know, Cathryn you worked in the White House. You kinda understand that you have this thing, you know, like…

Tiffani: Or it’s a standard, I guess. Could you call it that? Like, you have certain standards now.

Cathryn: The transformation experience that your pattern of how you think alters and it can be hard to find that.

Harper: It’s kind of what you were saying, Tiffani, though, where you are able to effect change for ordinary people. So I’m sitting here with a blank slate in front of me and I know I wanna make some motherfucking money, right? I know I wanna do some really good stuff, something interesting, I wanna do something big. But I also have this other little thing there that is like I wanna effect change in a positive way for ordinary people. And so when I think about the last company I did, it was retail software. It helped businesses basically put buy buttons which I was really proud of and it was really awesome. Looking at how it was incredible, like, just seeing everything they’ve done both upmarket and I was obviously more interested down market, all the things they do to help small businesses, to help single person entrepreneurs who are just making it happen, you know, just using PayPal. And it’s just really all over the world. So I was really excited about that.

But I’m like, “Okay, what’s next for me?” And I just had this feeling at the back of my mind where I was, like, “I wanna do something where I really am, like you said, like, impacting ordinary people.” Because that’s what you saw when you were involved with the Obama world. You saw that, you know, whether it’s, you know, Jay-Z up on stage towards the end of 2012 talking about as a young black man, he didn’t have anyone to look up to that would be president. And then seeing all these people around me who are young black men who are like, “Oh, shit, this changes their entire life.” This one thing changes their entire life. And I didn’t have that. And just seeing that, and learning that, and having that kind of like thrust into my brain, I was like, “Fuck, man. If can be involved with that feeling every single day, I would do anything for it.”

And so then it’s like this fight for how do I get back to that? And then the question is what am I really looking for? And so I’ve been thinking about this a lot of, like, what is that next thing? And how do I make sure I’m not just chasing an endorphin rush? You know, how do I actually… Because I think that’s where you get into trouble and I think that’s where you get in because you’re not doing it for the right reasons, and that’s when you become a mercenary. Now a mercenary for good theoretically, but still a mercenary. You know, but I wanna do something for the right reasons. I wanna do something because I believe. I wanna do something because I really think it’s gonna impact the world.

And then I also, you know, I’m a programmer much like yourself, Tiffani, and I try and program every day. Not anything fun, like, I do home automation shit or I, like, do a little hack or, like, whatever it is. I just try it because I like that something that I do relaxes me. It’s good. And so, I think, you know, what do I know about hack… Like, what high tech thing can I do? And what you were talking about with your project, I just love this idea of making some hack or making some small tech project because we’re programmers, and having that be able to actually affect real people, normal people. When I lived in Chicago, I’ve chosen very specifically never to live in the bay area.

Tiffani: That’s interesting.

Cathryn: I mean, I’m happy here but I think it’s good that, you know, you’re in Chicago.

Harper: I wanna be here because there are ordinary people because it is normal folks. And I wanna see those normal folks in my neighborhood. I wanna talk to them every day and have the experience of, “Yes, I’m also a normal folk in this kind of world.” Instead of having these, like, weird, like, I don’t know, you know, rent walls that, you know, no poor people can cross these line type of shit. You know, I wanna live in a place where you have a community.

Harper: All I’m saying I like this and I like the vibe of how do you just help some ordinary folks. And I think the interesting thing that I need to maybe dislodge from my brain is what does scale mean, right? Because on the Obama campaign, they were talking millions and millions and millions of volunteers. Our coworkers were millions and millions. You know, when you think about building a startup, you’re trying to hit as many people as possible because that’s what the VCs need and want. That’s what you need and want to help your economic world. But maybe that’s not what needs to happen. You know, maybe we could hit a small number of people, 80, 100, 1,000 and that might be enough.

Tiffani: Yeah. I mean that’s totally a thing. I feel like philanthropy has gone a little bit. Like, how many people is this gonna help? They want you to help, like, 10,000 people for $7 and it’s just like this is infeasible. So, you know, it’s very…but, yeah. That’s awesome.

Cathryn: And the one thing I think about when I listen to both of you is just sort of… It’s an indication that systems that we currently have in place have either failed or have failed to grow with us. Like, the systems of how we incentivize work, the systems of how companies are built and how they maintain profitability means that they are not tackling a lot of these challenges. You could even argue the way that traditional non-profits function in terms of these philanthropic arms have suffered in terms of evolving with how things work now. And so there’s a gap that entrepreneurs like you, Tiffani, are feeling where you’re like, “You know what? I’m gonna take good practice for building a business and I’m gonna apply it to these real hard, real world problems.” So there’s some system challenges that need to happen. And system thinkers, which engineers are brilliant at, I think might just be some of the magic sauce in helping us think about it systematically of how do you change it and how do you change the incentives so that you could build something that could scale, that helps millions of people.

Tiffani: Yeah, all right.

Harper: So I’ve one final question for you, Tiffani. Where do you get your news?

Tiffani: Oh, man.

Cathryn: That’s a small question

Tiffani: No, no. I thought you said something else. I was like no. Where I get my news? Unfortunately, Twitter and “Hacker News” and, like, Facebook.

Harper: Facebook?

Cathryn: That was you’re dog. I was like what just happened. His dog, like, shook the lid.

Tiffani: Ooh

Cathryn: And I thought it happened here and I was like, “What just happened?”

Tiffani: No.

Harper: My dog wants to go outside and play.

Tiffani: What kind of dog is that?

Cathryn: It’s a poodle.

Tiffani: You have a poodle? Oh, my gosh. My parents have a poodle but he’s like one of those Turkish poodles. What’s his name?

Harper: It’s Lulu. Lulu the Poodle

Tiffani: Okay, Lulu the Poodle.

Cathryn: Lulu, Lulu. Hi Lulu.

Tiffani: Are those [inaudible 00:40:20] in her hair? Oh, my goodness.

Harper: You know, you just gotta do what you gotta do sometimes.

Tiffani: Really?

Cathryn: So cute.

Tiffani: She is cute. Look at her. Like, oh my God I love poodles because they are so caring as opposed to smart.

Harper: I know they’re ridiculous.

Cathryn: She’s like look I wanna go out in 36 ° weather. She ain’t nothing but a dog to me.

Harper: She wants to go out and play I think, I don’t know. I mean, I got plenty but I think we’re done.

Cathryn: Yes.

Tiffani: Yeah, I don’t have any questions relevant to this thing. I’m just kind of like what about this, Harper? What about that? And like yeah, you’re fascinating to me, like seriously.


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