LISA CHOW: Before we get started, a quick warning: there’s some swearing in this episode.

ERIC MENNEL: OK we are entering the house, leaving the bedroom...

ERIC: It’s about eight in the morning on Wednesday, and I’m making my way through Providence Lodge—the big cabin we stayed in last night.

ERIC: All the lights are out.

ERIC: I’m trying my best to be quiet, but it’s the kind of home that creaks no matter how light you step.

ERIC: People asleep on all the couches out here. It’s kinda cute.

ERIC: When I went to bed last night, most of the riders were still awake. They worked late, some of them just setting their laptops on the ground and drifting off to sleep on the furniture. Team Denari, however, was having a frank discussion about some concerns they had with one of their teammates, Ash. Ash has been at the center of a lot of Denari’s problems—there was the argument about being a dysfunctional team on Monday, and later that conversation about choosing a CEO. And late last night the other members of Denari talked about whether he should even be allowed to stay on the team. From what I've gathered, a lot of this centers around a conflict with Anne-Gail, the sophomore from Mount Holyoke. This tape is from when we talked on Monday.

ANNE-GAIL MORELAND: With tech, I have no idea where the hell i’m going. I have no idea where I’m going to be in ten years, I have no idea where I’m going to be in a year. I have no idea where I’ll be in five days.

ERIC: Apparently Ash said something about how Anne-Gail was expressing opinions.something to the effect of: 'You're really young, and you don't have enough experience to make big decisions for the team.' Anne-Gail saw this as a personal attack. But Ash saw it as feedback, nothing more. Team Denari wanted to talk with Ash in private last night. So this morning, when Ash wakes up, I pull him aside to ask about the meeting. He still seems pretty tired.

ERIC: So I noticed last night that the team was having a meeting and they woke you up for that meeting.

MOHAMED “ASH” ASHMAWY: Yeah.

ERIC: You want to talk about it at all? What happened there?

ASH: No, I mean they just wanted to make sure that everyone is on the same page. They wanted to resolve as many conflicts as possible. So I think they voiced some concerns and I heard them loud and clear. So to avoid like lack of productivity we should really try to put our differences aside, so...

ERIC: And you feel like whatever was said in that meeting you feel like you heard them like you're working how to process the problem?

ASH: Yeah, I mean obviously there are things that I did disagree with and I will keep on disagreeing with. If I said something then I believe in it.

ERIC: Ash doesn’t seem to think this interaction with Anne-Gail was particularly serious, more that, other people made it serious. But he also knows he doesn’t have much choice but to make things work with his teammates.

ASH: There are usually many options. Not in this case. One of us can't just leave. That's not what I'm planning to do for sure. I’m gonna work through this. We'll just see what happens.

ERIC: Having fun still?

ASH: Relatively, relatively.

ERIC: Relative to what?

ASH: Relative to the situation like that we’re in. So, relatively.

ERIC: This is StartUp, from Gimlet Media. I’m Eric Mennel. We are on day three of our five-day series on StartupBus—StartupBus, the competition where teams have just a few days to start companies from scratch. While on a bus. We are on our way from New York to New Orleans, and this is the last day on the bus. It is the last day to actually build the companies before the pitch competition tomorrow. Now, every day has brought new challenges for these teams. The same challenges faced by lots of people when they start a company. These challenges can be professional. They can also be intensely personal. And today we’ll see how the bus forces people to confront these challenges head on—even if they’d rather avoid them.

ERIC: Back on the bus. Everybody loves the bus.

COLLEEN LAVIN: Don't be mean, Eric.

ERIC: I love the bus. I am one with the bus.

COLLEEN LAVIN: Stockholm Syndrome.

ERIC: So here we are, Wednesday. We get on the road at about 9am, leaving from the mountains of Western North Carolina, heading South, toward Atlanta. The bus itself is starting to look and smell more and more like a college dorm room. There are junk food wrappers in the aisle, discarded Red Bull cans in the crevices between the seats. People have been in the same chairs long enough that if you sit in the wrong place the cushion doesn’t quite conform to the shape your butt.

BUS RIDER: Nothing I drink will ever fit in the damn cupholders.

ERIC: Once we hit the highway, I make the rounds, to see how the different teams are doing heading into the day. Team Phishly, the email phishing app—they’ve actually got a working product now, that other people can test out. They launched an ad campaign on Facebook yesterday to try and attract users, and I ask how it went, how many people clicked through. Here’s Alex Romero, the developer who came up with Phishly.

ALEX ROMERO: The Facebook campaign was a $65 mistake. We were looking at the traffic and we had 65 clicks from Facebook and I was excited and then we look at our Google Analytics and it was zero. I was like, “What just happened?”

ERIC: Apparently, when Alex set up the ad, he directed it to the wrong URL. He set it https://Phishly.io. The problem is, they’d registered a different address—http:... without the “s”...

ALEX: which meant that all the traffic went to a page that doesn't exist.

PHISHLY TEAM MEMBER: They click on the link but they go nowhere.

ALEX: Yes. $65 typo, man. No other way of saying it, man.

ERIC: Across the aisle, Daisy is quietly plugging away. The window by their table is covered with a curtain of post-it notes, outlining the different tasks for the day.

CAL COSTANZO: What do you need from us to help you get your job done? The design stuff?

COLLEEN LAVIN: The design stuff? I’ll probably incorporate the design stuff later rather than sooner...

ERIC: And toward the front of the bus is Denari. Last night, on top of working through the situation with Ash, they also decided to elect a CEO. They asked Colleen Wong to do it. She agreed. And today she’s really settling into the role. Right now she’s helping Adam, the dad from Cleveland, focus the team’s pitch. They want to show that Denari is not just about blockchain technology. It’s also about helping people and NGOs.

COLLEEN WONG: When we do get to the pitching, I just want to clarify the stuff with the NGO...part.

ADAM GALL: Yeah. I get way too, like, “fuck everything else except blockchains” but you’re right.

COLLEEN WONG: Alright. Well, we'll talk about it, but keep coding. Don’t want to distract you guys.

ERIC: Over the last couple of days I’ve spent a lot of time with the competitors on StartupBus, getting to know them, and why they’re here. But there was someone else on the bus I wanted to talk with. Someone who’s competed on StartupBus before, and so has a little more perspective on the competition. She’s also the person who planned the New York route this year—Madelena Mak—she’s the conductor you’ve heard making announcements over the last couple of days.

MADELENA MAK: The number one rule on StartupBus is there’s no number two on the bus.

ERIC: Three years ago, on the bus, Madalena started a company called “MiniMap.” It’s an app that tells you what events are going on nearby, and the best way to get there. She made it all the way to the finals, and lost. But she’s still working on the idea. It’s actually in beta right now. And when we talk about her relationship to StartupBus, it becomes clear: Madelena was made for StartupBus. And StartupBus was made for her.

MADELENA: Yeah, it’s like StartupBus is like a weird childhood dream become true, almost.

ERIC: Madelena grew up in Hong Kong, where she went to a Catholic school. And it was there, during recess, that she got her first taste of mass transit.

MADELENA: I literally would organize and do these fake subway lines. Everybody, like, put their hands on each other's shoulder, you know, and form a train, and just run across the playground. It's fun to be, like, the train conductor, you know, and now we're bus conductor doing the same thing.

ERIC: Now, if you were to look at a map of this trip on StartupBus, you’d realize it’s a pretty insane route. It jogs and meanders. It’s nowhere near the quickest path to New Orleans. I mean, we spent a full 24 hours just in North Carolina. But Madelena says this was all very intentional. She wanted to take the riders to places they may never visit otherwise.

MADELENA: We definitely took some risks in terms of planning the route. I was pretty scared to go down south.

ERIC: Really?

MADELENA: Yeah, like, this whole trip I was kind of worried.

ERIC: Why?

MADELENA: I mean, you know, the current political climate, you never know if things would break out. You know.

ERIC: I should say, I know how this sounds. I grew up in the South, I’ve worked in the South, when people from New York say they’re scared of the south, it can be kind of annoying. But Madelena has a reason to feel this way. She identifies as transgender. She started transitioning when she moved to the U.S. for college. And leading up to this trip, the trip she was planning, she was reading these headlines that made her wonder: is it even safe for a person like me to be going to places like this?

MADELENA: I mean like, the day we departed, you know. July 31st, a trans woman got murdered in Atlanta. In New Orleans there were already...like in the Louisiana area already three people died, just because they’re trans.

ERIC: This year?

MADELENA: This year. Personally, I don’t want to stop by North Carolina because of all the bathroom bills that happened.

MADELENA: So that was pretty scary to me.

ERIC: It’s like a real thing.

MADELENA: It’s a real thing.

ERIC: Given this fear, you might wonder why Madelena even signed up to do this. To answer that, you need understand how deeply StartupBus runs in her veins, how important it is to her. She started going to hackathons about 4 years ago. At first, it was an isolating experience—she wound up making projects by herself, instead of with a team.

MADELENA:  It was very difficult, like just me going by myself to Techcrunch Disrupt. You know the first hour, you're in this giant hall, you know, everybody talking to each other. Mostly guys very excited about their ideas. And I'm just standing there and just being ignored because I don't look like anybody. So I felt very left out and excluded.

ERIC: But as crummy as some of those hackathons were, Madelena did notice one thing that kept popping up.

MADELENA: From the hackathons that I went to before the bus, I learned that quite a few winners were teams formed with people wearing shirts that says, “StartupBus.” Like, what the heck is StartupBus? Like why are these people winning hackathons?

ERIC: They all knew each other from this thing. And like, oh this might be the trick.

MADELENA: Yeah.

ERIC: And this realization came at a really pivotal time for Madelena.

MADELENA: The startup that I was working for, they only have a few months left and they’re probably going to go bankrupt, my romantic relationship was failing very badly, and my immigration visa was going to expire in three months. I mean when I come on the bus, I felt like that ,that might be my my hope. It cost $300. I didn't have any money left at that time, so I made a deal with my employer. If he can give me $1000, so that I can go on StartupBus. And he agreed. So thanks Kevin.

ERIC: Yeah, thanks, Kevin. Anyway, with all the visa stuff looming in the background, Madelena was really feeling the pressure to make StartupBus work.

MADELENA: I think I took it way too seriously. I definitely felt that that's my chance to stay in the United States, you know. Like I have to form a company on the bus. If I don't, I don't know who's going to sponsor me for another three years.

ERIC: You have to form a company because then you’ll have a company to sponsor you.

MADELENA: Exactly. It's like literally that's my survival.

ERIC: Did you tell anybody that?

MADELENA: Nope.

ERIC: Because why would you?

MADELENA: Yeah. That's way too much, man.

ERIC: So she gets to the finals, and loses. But after the competition, Madelena was able to find a visa sponsor and stay in the U.S. She got about a half dozen letters of support from the StartupBus community. The whole thing changed her life in this really tangible way. And it helped her understand why people sign up for StartupBus.

ERIC: What is the point of StartupBus to you?

MADELENA: What is the point of StartupBus? I mean, what is the point of life?

ERIC: Alright.

MADELENA: StartupBus was appealing to me because it sort of was a wildcard. And I know that I need to break out of my mold but I don’t know how to. I think, like, to throw a wildcard at yourself is one of the many ways to do that. One of the most effective ways of doing that. I mean, I think like lot of people who join the bus have that same feeling I felt, like that they want to be dealt a wildcard. That they want to be pushed to the limits so they can break out of their own old molds. Like they want to be something more than who they think they can be. It’s not about the bus. It’s about learning something about yourself.

ERIC: When Madelena said this, I thought of Adam, the dad from Cleveland, who was working a dead end insurance job, but now feels like blockchain is his chance to leave a lasting impact on the world. I thought about Colleen Wong, who had just quit her job, and is now leading a team of unruly developers to build a massively complicated project. I thought about Anne-Gail who had thought their life was set in stone, med school or bust, until they got involved in tech. And I thought about myself, and why I was starting to feel so connected to these people. When I first heard about StartupBus, I thought the idea was insane—a recipe for total disaster. But I’d also just spent the better part of a year trying to get my own projects off the ground, and they’d largely gone nowhere. I was in a long term relationship that was starting to fade. I was unhappy. And I couldn’t figure out what to do to change any of that. I needed a wild card. So a week on a bus, with a bunch of strangers with big ideas? I mean, why not? If you don’t like the direction your life is taking, why not set out on a journey where you’re totally blind? Who knows what you’ll bump into.

MADELENA: So we are going to be in Atlanta in 50 minutes.

ERIC: After the break, the teams get a harsh reality check from some business owners down South. And I check back in with Ash, to see where things stand with him and the rest of Denari.

MADELENA: Welcome to Atlanta, Georgia.

ERIC: It’s almost noon by the time we make our last major stop of the trip: downtown Atlanta. We’re at another co-working space. And the teams are about to pitch to some local founders. On the face of it, it’s not so different from our stops in D.C. or Charlotte, but this stop will actually be much more challenging for the teams. It’s their last chance to practice the pitches with actual founders—founders who, it turns out, will give them crucial feedback. The space is called digitalundivided. It’s an incubator program specifically for black and Latina women. It was founded in 2012 and has helped launch more than 50 companies founded by women of color. Inside the building, the walls are lined with Shepard Fairey-style prints of women from diverse backgrounds. There’s a giant poster from Shirley Chisholm’s 1972 Presidential campaign. People settle in as Madelena gives a welcome.

MADELENA: Thank you so much for being here everybody and thank you so much to digitalundivided. Let’s have our pitching begin. The first team is Daisy!

COLLEEN LAVIN: Hi! I’m Colleen. And I’m here to talk about everyone’s favorite topic. Death!

ERIC: Colleen Lavin’s pitch for Daisy is feeling really tight. It’s like you’re watching your comedian cousin do her fourth or fifth open mic night with the same material, and finally all the jokes are starting to land.

COLLEEN LAVIN: With no major competitors in the market, Daisy is poised… to kill it.

ERIC: Colleen takes some questions. The first one comes from a woman who goes by the name X. She works for Microsoft. And she asks if Daisy is only going to deal with the funeral event itself, or if it’ll be helping with all the other stuff that happens when someone dies, all the paperwork...

X: Cause I’m thinking like how do I get their death certificate, how do I get…like there’s so many things when a person dies when you start thinking about it.

DARLENE GILLARD JONES: Yeah, because I actually did go through a family member dying and having to have death certificates.

ERIC: This other voice is Darlene Gillard Jones. She’s one of the directors of digitalundivided.

DARLENE: For like the insurance people, like all these different people, so I think adding that component to it could be interesting.

ERIC: This idea, of helping people get their loved one’s death certificate, it hadn’t really come up during the pitches in the other cities. People had been asking questions about monetization and marketing—pretty standard stuff. But this death certificate idea felt different. And Daisy wound up adding it to their platform that day. When Denari steps up, it feels like this might actually the best audience for their company so far. X, the woman who’s been asking questions, is a co-founder of a blockchain company. So she understands the technology and its value.

COLLEEN WONG: People want to help people, and right now the platforms that exist to allow people to give money, they’re flawed systems.

ERIC: Colleen Wong starts by outlining the problem. GoFundMe only exists in 19 countries, she says That means 177 countries don’t have access to that kind of fundraising.

COLLEEN WONG: There are people everywhere who need money, want money to live their lives, to help other people.

ERIC: It’s more pulled together than their other pitches so far. But the questions they get from the panel are tough. X, the judge, she raises a point that hasn’t really come up at the previous stops: What about financial regulation?

X: You are talking about now securities exchange over multiple countries. Maybe there are reasons GoFundMe only deals with 19. Which I haven't heard you guys say. Is it cause they don’t want to? Because that’s kind of what it comes off as. It’s like, “GoFundMe is the largest one, they’re only in 19 countries.” Why is that?

MADELENA: All right. Great pitch.

ERIC: This stop in Atlanta is a stark reminder: these teams are trying to build working companies, and there are things that still aren’t working. The pitch competition starts tomorrow.  And there is still a lot to do. We leave digitalundivided and people scatter for lunch downtown. A small group heads to a cheap Greek place around the corner, and I find Alex Romero there, from team Phishly. Phishly’s made a lot of progress—they actually have a working prototype now, and Alex is starting to do that thing where you visualize your victory.

ALEX: It’s like the A-Team, right? I just want to be there tomorrow on stage, completely destroy the audience. Just wow them. And then just tell them, “I love it when a plan comes together.” I just want to say that. Like, if you come to me and tomorrow I get to say that. Oooo. Isn’t that the A-Team? I love it when a plan comes together?

DEVON VINCENT: I don’t know.

ALEX: No one watched the A-Team?

ERIC: After lunch comes together we make our way back to the bus. It’s then that I notice Ash, from Denari. He’s been quiet most of the day, clearly taking a step back, not interacting with his team much. But here, in Atlanta, he pulls Anne-Gail aside. Remember, they hadn’t been getting along since Ash implied Anne-Gail was too young and inexperienced to make big decisions for the team. While we’re waiting to get on the bus—I see the two of them talking by a light pole, maybe 10 yards away. I can’t tell what they’re saying, but it looks calm, professional. I eventually had a chance to sit down and talk with Ash about it. And about this question of what makes something a personal attack rather than professional feedback. I asked him how he determines where that line is.

ASH: Yeah, so I like being true to myself. Because I could have easily you know, just like, ‘Oh yeah but I'm sorry I guess I crossed the line. I was like personally attacking her.’ But admitting that would just be a lie. There is no second that I believed that at any given point that I was personally attacking anyone anywhere.

ERIC: But what's important is that like they felt like it was personal and like--

ASH: And it's OK, and it's OK I guess, like I mean, honestly. Anne-Gail can feel like, she has the right to feel whatever she wants to feel, right, because she is the opposite party.

ERIC: A quick note here: while Anne-Gail asked me to use they/them pronouns, this is not something they brought up with everyone on the bus, that’s why Ash is using “she” and “her.”

ASH: They heard her story but no one ever got a chance to hear my story directly. And it's very easy to like take sides with someone who's like saying that they're being attacked by someone who seemed to be intimidating in the beginning. The narrative, you know, flows. It flows. It’S not really like Ash was receptive and no, I mean it flows. It's plausible.

ERIC: The thing about StartupBus is that it really is like a reality TV show. It’s so intense that every interaction, every personality can feel like a caricature of real life. And when you become the outsider, like Ash has, you feel that in a serious way. I imagine this caught Ash off-guard. Cause in his own life he’s grown comfortable being the outsider. In fact, that’s where he thrives. Ash was born in Cairo. He says he comes from a long line of contractors and business owners, largely in construction. Which in Egypt can mean you’re pretty well off financially. But that also meant there were expectations, and a very particular road he could follow for his future—the road to running his own construction business in Cairo. He didn’t want that. He remembers sitting in grade school, hearing the name Mark Zuckerberg for the first time.  Facebook had just become a billion dollar company, with influence all over the world. And Ash was angry. He wanted that for himself. Not the money, but the impact, the scope. He wanted to be attached to something bigger than himself and his family. And he knew how difficult it would be to get that in Egypt. So at 17, he packed his bags and flew to America. First it was Ohio. Then Nebraska, then Minnesota. He’d be in college somewhere for a year and then transfer, a sort of pioneer’s trek across the Midwest in search of some key that would unlock his future. He did all this alone, leaving much of his family back in Cairo puzzled.

ASH: I didn't really have anyone to help or like pull strings. So I was more and more conditioned to keep emotions aside and really you know just try to force the other to like respect to you. 

ERIC: I imagine those are strange places to move from Egypt too.

ASH: Absolutely, absolutely. No one knows what Nebraska is. I like the unknown, I like being thrown with no floaters. To see if you can just swim, just swim.

ERIC: This was the moment I really started to understand why Ash is the way he is. I think there are usually two ways to respond to being alone in a place: you can put a lot of trust in the strangers around you, assuming they’ll look out for you, or you can put that trust in yourself, and go it alone. Ash seems like the latter to me. He likes being thrown into the unknown as a way of pushing his own limits, to see what he is capable of. I asked him about that moment in Atlanta, when I saw him talking with Anne-Gail by the light pole.

ASH: In Atlanta, I did take Anne-Gail aside, and I did give her a quick idea about how I rethought everything. And then I, I think perhaps I might have been a little bit rough in giving that feedback. and perhaps that's where the misunderstanding came in. But I also made very clear that my feedback is not different. Maybe the delivery. I failed the delivery right there. But I guess that calmed things a little bit down. Like, she thanked me for you know at least revisiting that and trying to reflect, I guess.

ERIC: I talked with Anne-Gail about this. And they said things did get much better after the talk with Ash. The two of them started joking, they were sending memes to each other. Anne-Gail also felt like the questions Ash raised about age and experience were just less relevant by day three. At this point, Anne-Gail had designed a beautiful front-end for Denari, and the rest of the team loved it. Before we wrapped up, I asked Ash if he learned anything going through all this stuff with Denari.

ASH: I think it's really just more of a reinforcing of a concept that I've always believed in. The people who choose to work with it, this is what will make or break anything. It's not the idea, it's not the technology, it's not, you know, the business solution that you've came up with, it's not the revenue model. It’s none of that. It’s the people you choose to work with, and if that is not 100 percent working out, nothing will.

ERIC: Can I ask how old you are?

ASH: Yeah sure. I'm 23. I'm actually, I'm turning 24 in a week.

ERIC: What things do you feel like you still have left to learn?

ASH: A lot. Everything. Everything. I know I might come off like giving a strong opinions about things. But no, I am truly self-aware of my shortcomings, which are a lot. There's so much out there still to learn. Really, the more you know the more you realize I don't know shit.

MADELENA: In two hours you’ll reach your final destination in New Orleans.

Cheers

MADELENA: Alright? Alright.

ERIC: The last two hours on the bus before New Orleans are a whirlwind. People are giddy, like they’re cramming in every last ounce of goofiness while they still can. Over on Denari, Ash and Colleen Wong are joking. They’re sitting across from Adam and Anne-Gail, who are losing their minds, pretending to pitch blockchain.

ADAM: Put it on the blockchain

ANNE-GAIL: Put it on the blockchain. It’s the ledger, it’s public.

ADAM: Yes, it’s backed by people.

ANNE-GAIL: By people. Not by government.

ADAM: Us. It’s about us.

ERIC: Up at the front of the bus Colleen Lavin tries to pitch Daisy one last time. But everybody’s heard it so much, they can’t help but heckle her.

COLLEEN LAVIN: Can you hear me in the back?

BUS RIDER: We can hear you in the front.

COLLEEN LAVIN: Oh good. I don’t care if you can hear me.

Laughs

ERIC: We’re just a few miles from New Orleans, now. You can see the lights in the distance, and then we pass another bus.

AMY HUA: Look guys it’s another StartupBus!

MADELENA: Now we are racing! Now the two buses are racing!

ERIC: Despite all their troubles—the personal dramas, the failed ad campaigns, the miscommunications—the teams all feel really good. They’ve overcome a lot. And they’ve built actual working products. In three days. On a bus.

MADELENA: Welcome to New Orleans, everybody. Congratulations! You made it to Louisiana.

ERIC: It’s late, after 10pm. Everyone is wiped and walking around with whatever the bus equivalent of sea legs are. People head to their rooms, planning to work through the night—to put the finishing touches together. Along the way we pass the teams from Ohio, San Francisco, Florida. It all feels very real again, like walking blurry eyed out of a theater after a long movie. Tomorrow, teams will start being eliminated. Everything they’ve been working toward comes to a head in the morning. The forecast calls for rain. The first pitch is in about 12 hours.

StartUp’s regular host is Lisa Chow. This episode was produced by Bruce Wallace, Luke Malone, Simone Polanen, Amy Standen and Max Gibson. Our senior producer is Molly Messick. We are edited by Annie-Rose Strasser. I’m Eric Mennel. Our theme song is by Bobby Lord. Build Buildings wrote and performed our special ad music. “Roll Bus Roll” is by Jeffrey Lewis. For full music credits, visit our website. GimletMedia.com/startup. Andrew Dunn and Mark Wilkening mixed the episode. Special thanks to Alex Blumberg and Emanuele Berry. To subscribe to StartUp, go to Apple Podcasts, or wherever you get your podcasts.  And leave us a rating! Five stars! Six stars! 10 stars!

MADELENA: Yeah, that’s way too much man.

ERIC: Find out more about the show at the Gimlet Media website: GimletMedia.com. While you’re there, you can see the special episode art we have for this series. Thanks to illustrator Josh Kramer. You can follow us on Twitter @podcaststartup. Thanks for listening. We’re back tomorrow.