LISA CHOW: Before we get started, a quick warning. There’s some swearing in this episode.
ERIC MENNEL: When I was growing up, my family was very into a particular kind of reality tv—competition shows. On Sunday night, it was The Amazing Race, where teams scoured the globe in the largest scavenger hunt in history. Then on Tuesday it was American Idol. Some nights it seemed like there were different competition shows playing on every TV in the house. My dad in one room watching Big Brother, me and my actual brother in the other room watching Fear Factor. Honestly, some of the best memories I have of my family growing up are when we would all sit down and watch Survivor. As a kid in suburban Florida, my world was kind of small. I didn’t travel much. I didn’t have a ton of crazy experiences. But watching competition shows, a bigger, higher stakes world felt more within reach. You could pray with Buddhist monks in the mountains of Tibet, or sing “Black Velvet” to Paula Abdul in front of an audience of millions. It was exciting. I wanted to be a part of it. When I decided to ride StartupBus this past summer, I thought I’d be reporting on a hackathon. I’d find one person, going through something interesting, and we’d just see how their week played out. Pretty simple. But when I woke up in a hotel in Raleigh, North Carolina that Tuesday morning, and I saw a giant “StartupBus” decal on the charter coach outside my window, I had this realization that would have thrilled my younger self to no end: “Holy shit. I’m not just reporting a story about a hackathon, I have landed inside a real life competition show.”
ERIC: Welcome to StartUp, the show about what’s it’s really like to start a business. I’m Eric Mennel. It’s Tuesday, day two of our five day trip on StartupBus—where a bunch of strangers launch businesses from scratch… on a bus. If you didn’t catch our first episode yesterday, you should definitely go back and listen, so you know what is even going on here. I’m riding from New York to New Orleans, embedding with three of the teams on this bus. There’s Denari, a bitcoin GoFundMe app.
ERIC: Can you do this in three days?
PARKER MCCURLEY: Oh, fuck yeah.
ANNE-GAIL MORELAND: Oh, we can at least build a hell of a concept in three days.
DENARI: We building shit.
ERIC: There’s Daisy, a website to help people plan funerals.
COLLEEN LAVIN: Because death is uncomfortable. Nobody likes to deal with it…
ERIC: And then there’s Phishly, an app to stop people from stealing your sensitive data.
ALEX ROMERO: And you may not think there’s a lot in common between my mother and John Podesta. But there’s one big thing. Which is, they’ve both been phished.
ERIC: Yesterday on the bus, I was very caught up in all the personal drama playing out. People were arguing, scrambling to come up with ideas. But now we're 24 hours in, and I have this pretty simple question. One that’s key to any good competition show: Who's winning? Who's in the lead? So that's what I'm trying to assess this morning. First, there’s Denari, the blockchain GoFundMe team. I spent a lot of time with Denari yesterday, and, put simply, things were a mess. They spent most of the day just coming up with a workable idea, even shouting at each other about it.
PARKER: We need to be more direct.
ASH: I am very direct. I was very direct…
ERIC: But this morning, when I find them outside a coffee shop near the state capitol building, things seem to have turned around. They worked through the night, and now, everyone is dialed in. They’re all on the same page.
COLLEEN WONG: We just snagged our Twitter handle.
ERIC: This is Colleen Wong, a 23-year-old who just quit her consulting job. She and her teammate Anne-Gail have been setting up the company’s social media presence.
ERIC: What's it going to be?
COLLEEN WONG: Denari give.
ANNE-GAIL: Let me create the Facebook page.
PARKER: Want to hear something beautiful?
ERIC: And this is Parker McCurley, another member of Denari, who, I gotta say, at least in terms of charisma, bears more than a passing resemblance to T.J. Miller’s character from “Silicon Valley.”
PARKER: Denari is the world's first truly international direct-giving platform.
ANNE-GAIL: Hell yeah.
ERIC: One of the teams I didn’t spend as much time with yesterday was Phishly, the phishing app. To be honest, Phishly struck me as the sort of class clowns of the bus. The team is a bunch of young guys, they’re all pretty goofy, they sit all the way in the back of the bus, like it’s middle school and that’s the cool place to be. And don’t get me wrong, they seem like they’re having fun. But they had a messy pitch in D.C. yesterday, and I just don’t know how seriously to take them at this point. That is until we get back on the bus. It’s about 9am, and we’re heading west. To get the day started, each team sends one person to the front of the bus to practice their pitch over the intercom. This is something that happens a lot on StartupBus—people are practicing their pitches constantly.
KARIM EL GAMMAL: Good morning.
ERIC: When it’s Phishly’s turn they send up Karim El Gammal. Karim is in his late 20s, boyishly handsome. He’s kind of got this Stefan Urquelle, “Family Matters” vibe to him.
KARIM: My parents are new to the internet, and as many of you may know it's so hard to train them on how to prevent and detect any social engineering attacks. After doing some research, quickly realize that companies also face the same problem. And that was the birth of Phishly.
ERIC: Karim moved to the U.S. from Cairo in 2012. He was actually protesting in Tahrir Square right before he got his first job offer here in the States, working for a hotel. He works for a tech firm, now, but he really wants to start his own company. Which is why he’s here on the bus.
KARIM: Phishly is a very intuitive and easy-to-use platform.
ERIC: And his pitch goes really well. Far better than any of Phishly’s other pitches so far.
KARIM: Thank you so much.
PHISHLY: That was awesome. Yeah! Nice.
ERIC: All of a sudden, this group of goofballs looks like they are actually in really great shape. This is part of what makes figuring out who’s ahead on StartupBus so difficult. Over the course of just a few hours, you can go from stumbling along, to being the only team on the bus with a coherent product. The reverse can also be true. A few rows away, I can hear some raised voices. It’s team Daisy, the funeral planning app. And there’s trouble. Yesterday, I would have put Daisy on solid ground. They had a great pitch in D.C. There were no major problems, no drama. But today they’re struggling to find their momentum. And now they’re arguing.
REBECCA BATTERMAN: What changed?
CAL COSTANZO: I did research.
REBECCA: What research did you show that, that negates our...
ERIC: Two team members, Rebecca and Cal, can’t agree on who their funeral app is actually for.
CAL: These funeral homes aren’t getting value from being on our site.
REBECCA: It’s not about funeral homes. It’s about the consumer who, whose process is simplified.
CAL: Okay. I’m trying to make a story to convince investors to invest in the company.
COLLEEN LAVIN: No, no. But that wasn’t your job.
ERIC: That’s Colleen Lavin—the woman who pitched Daisy initially. Apparently, Cal was supposed to call some funeral directors yesterday and get feedback on Daisy. He says he tried calling, but nobody answered.
COLLEEN LAVIN: Your job was to have a five-minute conversation with one funeral home and then get us all that stuff based on it. Those were your tasks before ten, remember? Like I...
CAL: Okay, who is deciding..?
COLLEEN LAVIN: We agreed on it.
REBECCA: We all agreed that’s why we wrote it down.
CAL: How are we making money? We’re not offering any value to the investors or to the funeral homes or investors right off the bat.
REBECCA: They are not our target, the consumer is our target.
COLLEEN LAVIN: Talk to your funeral home. Isn’t that what you’ve been wanting to do?
ERIC: They’ve spent half an hour arguing, as the teams around them pushed ahead. When they finally do reach a conclusion, Rebecca and Cal decide they need some space. So Cal gets up, and moves across the aisle…two seats over. Two hours pass, almost entirely on the interstate. And then, in the distance, tall buildings come into view. Madelena, the conductor, gets on the intercom.
MADELENA: On the right is Charlotte, North Carolina. The place where they care too much about who is using the bathrooms.
ERIC: It’s time for the day’s main pit stop, a coworking space in Charlotte. Just like in D.C., a bunch of local startup folks are here to weigh in on the teams’ pitches. Only this time, there’s a curveball.
MADELENA: Oh wait there’s another bus here?
ERIC: As we pull into the parking lot, there are already two other buses parked there. Madelena, who has clearly set this all up, feigns surprise.
MADELENA: Are they doing startups, too?
ERIC: Remember how there are six startup busses across the country all headed to New Orleans? Well, it turns out, the busses from Akron, Ohio and Tampa, Florida are also in Charlotte today. And for this round of pitches, they’ll all be up against each other. That question I had earlier this morning, about who was winning, that looks to have gotten a lot more complicated now.
BUS RIDER: Oh hey, what’s up?
ERIC: At first glance, the Tampa bus looks like it spent the night in Margaritaville. They’ve drawn their company names and little messages all over the side of the bus using those car-safe markers. But their energy is really high, they seemed focused and enthusiastic. And the Ohio bus is impressive in its own way. It turns out they teamed up with some people from San Francisco, and they’re manufacturing physical products. So they have 3D printers and computer aided design software. The whole thing feels like that scene in “The Sandlot” when the other team shows up in their actual jerseys and matching converse sneakers, and all of a sudden you realize, “Oh… this is some real competition.”
NICK PERSICO: All right. Welcome everybody. At long last, we’re going to start, okay.
ERIC: The pitches are happening in a back room. There’s a concrete floor and folding chairs set up for about 100 people. The audience for this round works in this building full time, running their own companies.
NICK: Each team is going to come up and do a two minute pitch.
ERIC: One the pitches from the Ohio bus is a company called See Searcher. It’s a rescue robot that can locate and dive for victims underwater before they drown. The guy making the pitch is a tall, burly paramedic who rescues drowning victims for a living. And boy does he know how to grab an audience.
SEE SEARCHER: Last week I watched a 21-year-old man drown because I didn’t have the time, resources, or the technology to get in there and save him in time. Our team of designers, engineers, researchers, and first responders such as myself, have created a tow-behind, underwater device that can drastically reduce the time it takes to locate, identify, and rescue a victim.
ERIC: There are other ideas that feel a little wilder. Yetigram, for example, is a website that helps you send…wait for it…singing telegrams.
Yetigram: (Singing) Diamonds are a girl’s best, best friend. Don’t give them a gift, give them an experience.
ERIC: As a reporter, I would call this moment both a gift AND an experience. One of the teams that to me seems the most promising is this team from Tampa, called Course Align.
COURSE ALIGN: We’ve done a ton of research and we’ve noticed universities aren’t preparing students adequately to get jobs.
ERIC: Course Align is software to help universities match the courses they offer with the jobs available in the market. It’s being run by these two guys, Robert Blacklidge and Trey Steinhoff. Robert and Tre just met yesterday, and they might be the fastest friends I’ve ever met. It’s kind of charming. I talked to them right before their pitch.
ERIC: I don’t know like, how’s the team gelling like how's it how's it been working together.
ROBERT BLACKLIDGE: It was incredible. We hit the road running. I mean with a lot of startups there’s that you know initial get to know you. We skipped right over that. Within the first hour, we already had pivoted two or three times. It was incredible. like yes the validated validated validated. And it's just been an incredible roller coaster ride.
ERIC: I mean you're talking about it like you just went on the best date of your life.
TREY STEINHOFF: I think that the hardest part of these competitions is that first bit when you realize that your idea is not as good as you thought it was and you have to like justify what you're doing. And so many teams fall apart in that part of the process. And we just powered right through that.
ERIC: Robert and Trey, very on top of things. It’s a world of difference from any of the teams on the New York bus.
ERIC: When it’s Daisy’s turn to pitch, the rest of the New York teams gather to cheer them on. The team sends up Colleen Lavin, the 24 year old developer who you might remember is a hacklete—she competes in a bunch of hackathons every year. While Daisy was her idea originally, she hasn’t actually had to do this pitch on her own yet. And just a couple hours ago, her team was arguing about who the site was even for. So given all that, this pitch feels like it could go either way.
COLLEEN LAVIN: Hi! I’m Colleen, and I’m here today to talk about everyone’s favorite topic: Death! We’re all human, we love humans, and we’re all gonna die. So we’re all going to have to deal with the horrific circus that is planning a funeral.
ERIC: It’s smart. And people are really paying attention. The mood is good. The whole thing lasts about two minutes. She’s even got a great kicker lined up for the end.
COLLEEN LAVIN: And with no major competitors, Daisy is poised to kill it.
JUDGE: Definitely keep that last line in there. Alright, questions, feedback?
ERIC: The pitching wraps up and everyone heads to the brewery next door to grab a drink. This was just a practice round, but it does seem like it shifted the mood of the bus. All of a sudden there’s a camaraderie. Two guys from Phishly, Devon and Alex, are at a table holding court with the other New Yorkers.
DEVON VINCENT: I think the ideas on our bus have the potential once we finish to actually move on and create these businesses.
ALEX: New York is forged in the concrete jungle. Only the best comes out of there.
ERIC: Walking into Charlotte, I had this sense that it was Daisy vs. Denari vs. Phishly. But walking away, it feels bigger than that. Colleen Lavin would later tell me that the support from the other teams on their bus was really nice, and surprising. It made it feel less like New York vs. New York, and more like New York vs. The World. Back on the bus. We’re on the road for another hour… then another… It’s all strip malls and tobacco shops. I think we’re heading West. It’s hard to tell. At some point the Internet starts to give out. The strip malls recede into the distance. The telephone polls are replaced by poplar trees. And we start to climb.
MADELENA: And where we're driving right now is the Blue Ridge Parkway.
ERIC: The Blue Ridge Parkway is a highway that roughly follows the Appalachian Trail through parts of North Carolina and Virginia. It’s more than 450 miles long—the longest linear park in the U.S, and beautiful barely begins to describe it. It’s got some of the lushest scenic views east of the Mississippi. After seeing nothing but concrete barriers these past 48 hour, it’s like that first cup of coffee when you’re hungover. Everyone shuts their computers and looks out the windows. As we reach the highest point of the parkway, Madelena puts some music on over the intercom. People get up off their seats, and they stare out the window at the valleys below.
ERIC: They’re laughing, joking. Everyone is having a good time. We stop the bus and get out at one of the overlooks. People file out and start taking selfies.
BUS RIDER: Guys, let’s take that team picture.
ERIC: They’re running around, giving hugs. Team Daisy actually finds some daisies in the grass.
COLLEEN LAVIN: Dude, those are daisies!
ERIC: Some people even ask me to get in their photo with all my recording gear, like a mascot at baseball game.
BUS RIDER: Yo. One with Eric.
ERIC: A very lame mascot.
BUS RIDER 1: Yeah, Eric is the man.
BUS RIDER 2: With the mic in his hand. Did you get it?
ERIC: It starts to rain. And everyone scatters. I think this is the part of competition shows I never fully grasped when I was watching them as a kid. Yes, they pit people against each other, head to head. But the experiences along the way feel so singular, and so high stakes, they may actually do more to bring those people together, than push them apart. I mean how often do you find yourself on the side of a mountain, running through the rain with a bunch of people you just met yesterday? On a bus? It’s not exactly Buddhist monks or Paula Abdul, but it still feels pretty special. Coming up…
ERIC: I’m not trying to be accusatory.
FRANK CARINGI: No no, I don’t want him to paint you… I don’t know him.
ERIC: No no no no and what I’m saying is I’m trying to...
FRANK: I get it now, that’s not what you meant.
ERIC: Things get tense for Denari when they nominate a CEO. That’s after the break.
ERIC: Welcome back. We pull off the Blue Ridge Parkway just outside Asheville, and by 9pm we’ve stopped for the night. We’re at a place called Providence Lodge. It’s a retreat center built in 1915 for Methodist pastors. After spending the morning focused on the competition, I wanted to circle back to check in on one team in particular: Denari. Yesterday, Denari was having leadership problems. They had a bunch of big personalities trying to negotiate an idea. But there was one person on the team I really I hadn’t heard much from, someone quieter, observant. Her name is Colleen Wong. Colleen quit her job as a consultant last week, right before getting on the bus. She’s 23 years old, and there have been moments when it seemed like she was being talked over by the rest of her team. She says it’s the kind of thing she has to deal with a lot, because she’s drawn to ambitious projects and people. But she doesn’t always know how or when to assert herself, let alone take the lead. I talked with her outside the lodge.
COLLEEN WONG: I have a different way of leading. This has come out in like past scenarios, where I’m usually the one who is facilitating and making sure things get done. But I'm also not a very loud and vocal person. I have a lot of self-doubt. That’s something that I’m working on. I like physically get tired if I repeat something like 10 times and no one is listening to me. And like because of my past, when I do speak up, sometimes I have been physically reprimanded for that. So it's hard for me, because of my culture and my personal experiences, to speak up loudly amongst a bunch of bro personalities.
ERIC: You’ve been reprimanded in the past for having spoken up. This is in your personal life, I imagine.
COLLEEN WONG: Yeah. There was physical violence. And at one point that really, really, really took a toll on my own mental health, my academics, my well-being, my social life.
ERIC: Colleen says in her teenage years, she experienced significant physical and emotional violence. We can’t go into too much detail about it, but it was at the hands of an authority figure. Colleen was a good student, but after the problems began, her grades plummeted. She developed mental health issues. Things have gotten better now, but for several years it was a very bad situation.
COLLEEN WONG: That experience has really shaped who I am. And like how I see the world and how I see people and experiences and opportunities and suffering.
ERIC: I can see why, like, being in a scenario with three or four pretty loud guys who are like pretty strong personalities, why you wouldn't necessarily naturally think to yell back.
COLLEEN WONG: I mean I do. I can get pretty like aggressive and catty if I feel like doing that. But it takes me time to sort of loosen up, And like be my genuine self with people. And, I learned so much from recovering from all of that, and from learning how to grow and, like, become the person that I want to be. But it takes time for me to get there with a group.
ERIC: Colleen settles into the room she’s sharing with her teammate Anne-Gail. There are more than a dozen rooms at the lodge, and a big balcony overlooking the yard. There’s a spot for a campfire. I head out to the balcony where I bump into Frank and Ash from Denari. Frank and Ash were the two guys dominating the argument in D.C. yesterday, when Denari still didn’t know what it was building. We start talking, and they tell me that earlier today, one of the mentors suggested Denari elect a C.E.O, someone to be a decisive voice. Ash and Frank talked about this with Adam, from Cleveland. And the three of them had an idea. Here’s Frank.
FRANK CARINGI: We thought that that was something to consider. And we are, me and Ash and Adam, are going to pitch to consider electing leadership. And also, we all agreed that Colleen would do a very good job.
ERIC: Colleen Wong, that is.
ASH: So we will...
FRANK: So we want to talk to them and see what they think. Talk to Anne-Gail and Parker…
ASH: And Colleen, all three together. Tell them that we think that Colleen would do a good job and that all three of us are on board with that decision, and get Parker’s and Anne-Gail’s vote, essentially.
ERIC: What is going to be solved by having this sort of position on the team?
FRANK: We have to do a lot tomorrow in one day, and a lot of us have strong personalities, that's why we're here. And we have, we have stake in this and we want to do really well. Sometimes we disagree, and I think that it would be useful to have a person who, who you think will make a really good decision, and who has a good head about, you know, being the final call.
ASH: That person being we think is unbiased.
ERIC: This is Ash.
ASH: And also, honestly, like to be very, very honest, like we, not only do we think Colleen is like qualified as a person but we, I personally speak for myself, but I also know Frank would probably agree with me on this. We’d like Denari to have a woman for a CEO. We think that’s something that we’d like to actively work on.
ERIC: And why is that?
ASH: Well, because there are few women in tech, and this is something that we could do, and this is someone that we trust. We see that they’re qualified.
FRANK: She can do a great job. They’re all checkboxes.
ASH: So why not.
FRANK: So we think it’s the best move.
ERIC: I think if people heard there were three men who were strategizing about the potential and future of one of the women on the team, like it might sound a little funny. Does that, like, does that sound weird to you guys at all?
FRANK: I mean it was, the way that it came about was mostly just that, you know, Adam thought Colleen was the best choice, and I agreed.
ERIC: I’m not trying to be like accusatory about it. I'm just like, I'm like imagining this, I had this picture in my head of you guys on the porch, and like you guys are the stronger personalities on the team, like that's totally obvious. And...
ASH: This is not a decision, like we haven't decided that this person is going to do X, Y, and Z. We're simply electing to go and tell Colleen, “Hey, we think that you should take that position.” I get, I get the notion. I get the point. But I don't think there's anything funny about us, consciously, initially just thinking of Colleen as a qualified individual. And it happens that she's a woman, honestly. It did not… we first weren't looking for let's make sure it's a woman, and then let's also find someone who is qualified. That's not how this team operates.
FRANK: Adam just said, “Colleen would be a good CEO.” And after you know, after quite a while of like, lots of good reasons why she would do a good job of diffusing and making the right decisions, you know, the fact that she's a woman and there are few women in tech as CEOs, as a fact, you know, it was brought up. But I don't think that's what Ash meant when he said that. You know, I don't think he meant it in that kind of way….I don't want him to paint you in that… I don't know him.
ERIC: No no no, and what I'm trying to say is like, like look what I'm doing is trying to…
FRANK: I get it now…
ADAM: See, this is exactly why I suggested it.
ERIC: Now at this moment, Adam walks out onto the porch (he’d been doing something inside), and he tries to get this conversation back on track.
ADAM: When you guys get into it, there's no stopping you… she’s knows how to rally people. And so she would be good at managing us.
ERIC: Despite how much I'm pushing back, I do recognize the awkward position they’re in. For one, Colleen would be very good in this role. And it makes a lot of sense to suggest her for it. Looked at one way, this is a progressive move. They’re elevating a woman into a leadership role. But I think there is something else going on here that I don’t think Ash, Frank, and Adam totally recognize.
ERIC: They’re asking a woman to do a job none of them are fighting for, a job they don’t want to but probably should do themselves: manage their behavior. Later that night, they offered Colleen the C.E.O. job, and she accepted. It’s dark out now. Down in the yard, some people are starting a campfire. Me, on the other hand, my podcast spidey sense is tingling. I hear an opportunity for some of that sweet, sweet nature sound. So, I head down the hill to record the summer crickets and katydids. In stereo.
ERIC: They’re on the left…they’re on the right….They’re on the left…they’re on the right…
ERIC: It’s like being wrapped in a nice warm audio blanket. It’s cozy.
ERIC: Almost makes you just wanna drift off to sleep. Call it a night. Yeah, me too. So I walk back up to the lodge to turn in. But when I get to the front porch, I see Team Denari huddled there, together, talking. It looks serious. Everyone is there, except one person—Ash. He’s asleep inside. People’s arms are crossed, and they’re all standing up. So I walk over, and I turn on my mic. This is Anne-Gail.
ANNE-GAIL: It would be very productive for us right now as a group to just sort of come together for the next two minutes, discuss, you know, what we all want from the future, and basically discuss how the person who's creating friction, do they have a role here?
ERIC: It takes a minute, but here’s what I piece together. There’s been some tension between Ash and another member of the team. And last night he said something that upset this other person. The team won’t tell me who it is, or what was said, but they feel it’s serious enough to warrant this discussion. And they’re asking themselves, should Ash even stay with Denari? Here’s Anne-Gail.
ANNE-GAIL: And I think this depends on his response to the situation that we bring. I 90% think we have to... we can't just leave him out of this 100%. We can't just pop, like, have a vote count out, and just pop in and be like you're out.
ERIC: One of the bus conductors, a guy named Ajay, is there, listening to this unfold. And he urges some caution.
AJAY DESAI: You guys learned something really valuable here. And now there’s an opportunity to kind of come together as a group and just deal with it. And I think you guys have a good idea. Before you guys deal with it, because it involves another individual. And I think it is incredible….
FRANK: With feelings and like... there is a nice and sensitive way to approach something like this.
AJAY: There’s passion. There’s passion. You're learning that right now. It's friendship, it's relationships, relationship management. You can always cause somebody to help and grow. And what I don't like to see is I don't like to leave anybody behind.
ERIC: Ash is asleep, so they're going to go wake him up and talk to him. The team asked that I turn off the mic and let them do it in private. They told me that they would fill me in later. It’s late by now, probably around midnight, so I go to bed, not knowing what things will look like tomorrow.
ERIC: 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 Ian Scott mixed the episode. Special thanks to Alex Blumberg and Emanuele Berry. To subscribe to StartUp, go to Apple Podcasts, or whichever app you like to use. And while you’re there, I don’t know, leave a review!
BUS RIDER: This is just the best podcast ever.
ERIC: Find out more about the show at the Gimlet Media website: GimletMedia.com. You can follow us on Twitter @podcaststartup. Thanks for listening. We’re back at it tomorrow.