The REWORK podcast

A podcast about a better way to work and run your business. We bring you stories and unconventional wisdom from Basecamp’s co-founders and other business owners.


Meet Andy

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Basecamp’s new head of marketing, Andy Didorosi, talks about starting a bus company in his hometown of Detroit to help fill a gap in public transit; what he learned about building a business with a “buy one, give one” social mission; and why he left the company he founded to join Basecamp.

The Full Transcript:

Shaun: [00:00:00] Rework is a podcast by Basecamp. Basecamp is software that helps you organize the work you need to do the work you want to do and the people you’re working with. Try it free

[00:00:11] Broken By Design by Clip Art plays.

Wailin: [00:00:12] Welcome to Rework, a podcast by Basecamp about the better way to work and run your business. I’m Wailin Wong.

Shaun: [00:00:17] And I’m Shaun Hildner. Last week you heard from Basecamp CEO Jason Fried about how he narrowed down a field of 1400 candidates to find a new Head of Marketing, a position we’ve never had here before.

[00:00:31] On today’s episode, our new coworker Andy Didorosi sits down with Wailin to talk about the company he founded, the Detroit Bus Company, and what led him to apply for the marketing job here at Basecamp.

Andy: [00:00:49] My name is Andy Didorosi. I was born and raised in Detroit, Michigan and I still live there and I’m the Head of Marketing for Basecamp now, which is a funny thing to say.

Wailin: [00:00:57] Congratulations.

Andy: [00:00:58] It’s day three.

Wailin: [00:00:59] Is that the first time you’ve said it out loud in that kind of formal way?

Andy: [00:01:02] Yes.

Wailin: [00:01:03] How did it feel?

Andy: [00:01:05] It felt official. Yeah. It’s such an official title. Like, I think it could go on a badge. A brass badge. It’s nice to be here.

Wailin: [00:01:12] Oh, good. Well, it’s nice to have you here. And thanks for coming on. We just, it’s day three of your tenure at Basecamp and we already have you in the studio with the headphones on, in the hot seat.

Andy: [00:01:21] I kind of expected it, though. Yeah, I figured this would happen.

Wailin: [00:01:26] So I wanted to just hear your story and what you were up to right before you took this job and kind of what motivated the big switch.

Andy: [00:01:34] Yeah, for sure. Like I said, I was born and raised in Detroit. Public transit is really bad there. And this was 2011 that there was a lot of newspaper articles and stuff about how public transit was just not gonna move forward. The city and the suburbs weren’t agreeing and I was really frustrated about this. We’re a city that’s big enough, it should have it. We have enough people that need it. We have a ton of folks who just can’t afford a car. And so people just can’t get to jobs that exist. And that’s that sort of problem where a government can solve it and they just kinda refuse to make that connection. We’ve got 640,000 people in Detroit proper. And then the burbs are, we’re all the fair enough jobs are. Late manufacturing and retail and service industry.

Wailin: [00:02:16] Is a lot of this inequity in public transit felt along racial lines?

Andy: [00:02:20] For sure. I mean, the city of Detroit, I think the last time I checked is 84% black. I think it’s the blackest city in America by the numbers. And of course, our transit systems don’t work together well. So there’s one transit system for the city called DDOT. And then there’s one transit system for the suburbs called SMART. And until recently they didn’t work together at all. You basically bought a fare for one, took the bus to the edge of the city, got off the bus, waited an hour or more for the next bus. And then you bought the next pass for the next bus, and you continued onward to the suburbs.

[00:02:56] It was like some kind of dystopian movie where these two very similar organizations driving the same buses, taking the same people, didn’t work together. And it was purely because of politics.

Wailin: [00:03:06] Yeah. Did it—did the DDOT system even extend into all the neighborhoods it needed to go?

Andy: [00:03:10] No. No. The DDOT system is horribly underfunded. Even until today, I mean we’re talking about 2011 when a lot of this came to bear. But even today, the Fed has a bunch of transit dollars available for us, but we don’t have a funded regional transit authority in which to disperse those. And so it makes us just not eligible. We’ve turned away so many dollars that we’re supposed to have and it’s all just because of political inefficiency.

Wailin: [00:03:36] So you saw a route and you’re like, I need a bus that goes between the city and the suburbs reliably.

Andy: [00:03:45] Yeah.

Wailin: [00:03:45] And you said, I’m going to buy a bus. How did you buy a bus?

Andy: [00:03:48] I identified that I wanted to run a bus and it was a late night sort of, just pissed off thing. It wasn’t, there wasn’t a plan, there wasn’t a structure. The buses were for sale in a church weekly, the sort of mailer and it was the local school system selling a bunch of buses that they didn’t need anymore. The listing said, here’s these buses for sale. It’s three or four of them mail in your highest offer. And I had been selling industrial and restaurant equipment up until this point and I just knew that wasn’t going to work for them. I’m like, there’s no way that people are mailing in their offer. They’re going to be sitting on these buses. And I reached out and I said, initially I said, hey, I’ll help you sell these buses. That’s what I do. You don’t have to pay me anything up front. I’ll just sell them for you and we can work out something.

Wailin: [00:04:34] Like a consignment thing.

Andy: [00:04:35] Yeah, yeah, yeah. And so I drove over there with some friends and we drove four school buses back to my building. I had a small warehouse.

Wailin: [00:04:44] What’s it to drive a school bus?

Andy: [00:04:45] It is shockingly easy. The nice thing is that you have this giant mirror above you that you can see everything behind you and it’s all windows. And so you don’t even really need to turn your head to see what’s going on behind you. The axle is in the middle. So the tail, kind of, I say it wags when you turn the bus, the back of the bus comes way out, which, could be dangerous. But it’s really easy to pilot 18,000 pounds. Shockingly so.

Wailin: [00:05:08] So you got the four buses?

Andy: [00:05:10] Yeah. Brought them over to the… I brought the buses over to the building and started to list them. And this is when I got into this transit conversation. I think I was out to dinner with some friends and we were talking about it and we talked about the recent headline that this transit project that was supposed to happen was killed. And I was kinda in my brain thinking about, like, I’ve got some buses back at the place.

[00:05:32] So I came up with this plan for this route. It was really just all inside my head because I just felt that there had to be a better way and maybe if I made this, you know, this little demonstration happen, it could bring some attention to the issue. I had no plan for where it was going to go from there. And so, I called the school system back and I said “Hey, what I’ll do is I’ll sell the three buses for you, zero consignment because the consignment would be about this much money and that’s worth about one of these buses.

[00:06:03] It’s funny that you can go so quickly from an idea to having something out in the world that it even surprises you. Before long I had a bus company, and I don’t want to compress all of the complexity of getting it going. There was a lot of sundries in the way, you have to have insurance, you have to have a state authority. The state has to permit you to operate buses.

Wailin: [00:06:25] So, this first bus, did you drive it?

Andy: [00:06:29] So I went and got my commercial driver’s license and I drove it a bunch. But I was smart to get school bus drivers really early on and I actually offered jobs to people from the Ferndale Public Schools to drive nights and weekends, you know?

Wailin: [00:06:41] And what were the hours of the route?

Andy: [00:06:43] Well, the first one I ran, I ran a lot hours. So it was , I think it was noon until midnight or 2:00 AM Friday through Sunday. And you could pay five bucks and ride as much as you wanted. And of course people loved it. It was super popular, especially on Saturdays. We had packed buses, going between these cities. And this was through parts of Detroit and then nearby suburbs, kinda these pockets of where people were. So we actually used bars as our bus stops because they were really where it worked well. They had bathrooms, a lot of them had cheap food and so you could use them as a neighborhood nexus. That’s kinda like what bars function as socially. So why not have them function as that from a transit perspective.

[00:07:28] We quickly shot to 30 or 40,000 followers on Facebook. And it was before the death of organic reach. Basically anything we put out, here’s the route tonight, it would get three or 400 likes compared to today. When you try to build anything on Facebook, if you’re not doing paid, you don’t get anywhere.

Wailin: [00:07:50] Did people pay cash?

Andy: [00:07:52] People for the route paid mostly in cash. We had Square. Square was pretty early then too. And so I put a little table in the bus. I took out a seat and put an iPad on a… I made a little table out of a palette and so people could walk up and pay with the Square reader. We just used all of these cool internet things. We had GPS tracking really early so you could see where your bus was on a map.

[00:08:20] And that seems so obvious now, but back then, we had to take an old cell phone and have it report up to a server and then have that reproduce itself on a map as a dot. And that was really hard to do. It wasn’t that easy. So we’d email that link to all the people that signed up to ride that night. People could buy tickets online. We used just Eventbrite. So you’d pay your $5 online.

Wailin: [00:08:42] Right. Although, the population that you’re trying to serve is going to be very cash-based, right. If you’re talking about people getting out to jobs and stuff.

Andy: [00:08:49] Yeah. So, there’s this kind of simmering misconception that the more low income someone is, the less likely are to have technology or be banked. And that’s a trend, but it’s not absolute.

[00:09:05] So we would have plenty of people pay with cash. we had a little a metal cashbox on each bus and we’d stuff the cash there and tuck it into a little pocket on the bus. But you actually touched on something where our population, who needed us most, they would have credit cards, or they would have cash and we would accept the cash. But what we got into is that plenty of people would be, like, I can’t even afford the $5. The $5 is too much for me to pay for this. The public bus is a $1.50 each way. And even though it takes two hours longer, I’m gonna take the public bus because a couple of bucks a day adds up over a month.

[00:09:44] It’s kind of a mind-blowing thing. If you’re of an income level where you pretty regularly go to Starbucks, you don’t think about the couple dollars. It’s just a tiny little vampire bat on your bank account and you just don’t really think about it. Whereas when you’re budgeting dollar to dollar, it’s pretty big. We heard this over and over and over again that we were self-selecting what’s called rider of choice, people who can pay for a slightly better service and they leave the public service and it hurts local transit agencies.

[00:10:15] We want to serve people who could never afford even a dollar for a ride, you know? And that’s kids, that’s job seekers, that’s elderly people. These are folks who are most vulnerable and you can’t have any money be part of the concept or they’re just like, I’m out. Sorry. I can’t, I can’t do any of it.

[00:10:34] And I didn’t want to build a business around trying to extract money from people who, like, that’s the most precious resource they have. So, I’d rather sell a high margin thing, like a tour or a wedding charter and then use the extra money from that to provide free rides.

[00:10:47] We found that weddings really liked our buses because we hand paint them. They don’t look any other bus you’ve seen. They’re hand-painted by Detroit mural artists. And we found a lot of people wanted tours , to see the city. And these are folks who have lived near the city for a long time and just haven’t really explored it. They haven’t gone into the history of it. And so we’re making people who live in the suburbs into local tourists.

Wailin: [00:11:11] Yeah. So that was that spark of idea where you thought, okay, we’ll offer these higher value tours to people who can pay and then that’ll subsidize the social mission of providing rides to a daycare and aftercare.

Andy: [00:11:25] We found that the biggest trends of gap was kids in Detroit. They’re the most vulnerable population because right now, to get to school, they take the public bus, which is overcrowded. They can only get yellow bus service if they’re K-5. They have to be within a certain distance of the school. If they’re too close, they don’t get it. They’re too far away, they don’t get it. If they’re too far away, they don’t get it.

Wailin: [00:11:43] If they’re too far away, they don’t get it?

Andy: [00:11:44] If they’re too far away, they don’t get it. It’s like a doughnut of service that’s offered around the school. When winter comes and it starts to get dark at 5:30, a lot of them just stop going to school. It actually causes a ton of dropouts because you think about walking, two or three miles in the snow that, at 7:30 in the morning in a city with a very high crime rate, like, no way. I’m just not going to go to school. And that’s a perfectly reasonable response, unfortunately.

[00:12:11] That we’ve made kids choose that or made their parents choose that. So, we’re a ride for ride model. It’s like TOM shoes. You buy a tour ticket, you use one of our buses for a wedding, we give kids free rides to school and after-school programs. It’s actually a 501(c)(3) now. And it used to be something we just did with our own buses to give kids these free rides. But we’re trying to grow it beyond just doing these rides as we can do it with our own money. We’re trying to grow the ride services, into its own sort of organization that can have leadership and lifeblood beyond us.

Wailin: [00:12:46] Yeah.

Andy: [00:12:46] There’s only so much you can do with, a small company and a few buses. We also, for a little while there, landed some grants, which seems a wonderful thing, but when someone hands you a check for $183,000, which was our first, sizable grant, your perspective on your organization and how money exists, changes whether you want it to or not. You start to steer your organization to try to get more of that because it seems the easiest way to provide your good. But there’s sort of dark issues attached to that. You’ve just made your organization part of whoever gave you the money. You’re kind of working for them now. The way they get their money, they have to make certain reporting things to their funders and shows certain data points that are really sexy.

[00:13:43] Would you rather give out, 600 bus rides in a school year or would you rather give out 15,000 backpacks. And people almost always choose the backpack because you can put the backpack on a billboard, and you can show a photo of a kid with a backpack whereas a photo of a kid on a bus isn’t as gripping. And then the grants started trickling off.

Wailin: [00:14:05] So that’s how you landed on the ride for ride model?

Andy: [00:14:08] Yeah, the ride for ride thing came up because you’ve seen a few companies do it and it’s kind of become in vogue where, you buy a t-shirt and we’ll give t-shirt to someone else. The way we found it to work was we had the same buses. It wasn’t we were just selling someone two of something and then giving one of them away. Our cost is in holding these buses and keeping them insured and housed and paying for our office folks. If we use the buses for these for profit things on nights and weekends and then we gave the rides away during the week when kids need them most, our costs don’t go up that much.

[00:14:49] And so this is sort of virtuous cycle where people are more likely to use our nights and weekend services because they like to support the free rides. People won’t buy a thing, though, if the base service or good itself is not something that they want. If your whole business is based on the buy one give one model, but the buy one thing sucks, you’re not going to get anywhere because people will just donate the money. So we first had to make sure the service that we were offering was awesome. So the buses are hand painted, like I said. They have music in them.

Wailin: [00:15:27] Do the drivers play music when they are driving the kids around? Do the kids get to pick music?

Andy: [00:15:33] Yeah, to an extent. So we used to have it so the kids got to pick whatever and then we got some really…

Wailin: [00:15:41] I can tell you’re not a parent.

Andy: [00:15:41] We got some really out there stuff, right, right? They would plug in the Spotify and have the Explicit version and we’re like, no, no, no, no, no, no, no.

[00:15:50] You know, Detroit’s the home of Motown music and so we started making some thumb drives and we would let the kids pick what thumb drive they want to spin up and pop it in there and let it rip.

Wailin: [00:15:59] Baby shark. On loop.

Andy: [00:16:00] Baby shark, nonstop. Grandma shark, grandpa shark, all the sharks. I can do the hand motions. Yeah. Yeah. We understand children.

Wailin: [00:16:09] This is kind of this awkward smash cut transition, but then why leave that all behind to come to our little operation here at Basecamp?

Andy: [00:16:17] The bus company, I had started it in 2011 I’ve worked in it seven days a week since then. I have created a really great team. Everybody there right now is definitely the best version of the team we’ve ever had. When I’m there seven days a week, 10 hours a day, it’s really hard for them to grow beyond my ideas and concepts. It’s really hard to let go when you grew something from one school bus, you know? And so, for the next 10 years, I want to see what they do with it. I want to see how it can grow beyond me. So when Jason emailed me about this role, about this Head of Marketing role, my brain didn’t even consider it. It wasn’t even on the radar. But I knew that I wanted to do it because I’d followed Basecamp and 37 signals since way back in the day.

[00:17:15] I used to work at Jalopnik. We used Campfire, we’ve worked actually, at the bus company in Basecamp maybe three or four years now, maybe a little bit more. And so, I followed 37 signals and Basecamp for so long and then this job opens up and I’m like, whoa. I know exactly how to share this with other people because I do it all the time.

[00:17:38] And this sounds an ad, but I’ve evangelized for these products for so long that I’ve got my pitch down pretty well. I can steal a cocktail party conversation pretty easily about, “Hey, you ever heard about asynchronous working.” I thought it was the perfect fit.

Wailin: [00:17:53] And did you mention that Jason had emailed you, too?

Andy: [00:17:57] Yeah. So Jason had emailed me this listing and the email is real short, but it just said, like, “Hey, we’re hiring for this person. You’d be an absolutely perfect fit for it, but you’re probably too busy. So just share it with anybody you think.” And I really don’t think he was being coy about it. I think he really was like, “Andy’s got a lot of stuff on his plate. He’s probably not looking for a job, but he probably knows the person who could be good at this job.”

[00:18:23] I sorta had a what they call the whole body yes when I really allowed myself to consider the possibility of changing my role in my company and then taking this job. Most of my productive career life so far has been small organizations or projects that I am the last word. I would just, I’m hungry for a new setup where I can learn things that I can’t learn, being the only voice.

Wailin: [00:18:55] And you know Jason, you had met him at a conference or something years ago. That’s how he knew you?

Andy: [00:19:00] Yeah, I met Jason because um, he was speaking at the 99U Conference with Adobe in New York and I had gotten invited to speak at it for some reason. I still don’t understand how or why they picked me, but I’m grateful they did. I got to follow Seth Godin, which is like, my badge of honor that Seth Godin opened for me. I actually felt super sick prior to my talking just from anxiety. It was a 25-minute presentation, which I’d never spoken that long on anything.

Wailin: [00:19:28] That’s long, that’s long.

Andy: [00:19:28] Yeah. And I did the Cardinal sin of practicing a little but not enough. And so I had a little bit of knowing what’s going on. It had some structure around it and some framework, but I didn’t have it memorized. So I gave the talk. I think it went pretty good. But 10 steps off that stage, I threw up all over the place.

Wailin: [00:19:50] Oh, mom’s spaghetti.

Andy: [00:19:50] Yeah, straight up Eminem, yeah. Detroit represent. In the restroom. But you can actually see me turning pale in the thing. I just lost all my color. But I did it, I finished the talk. And then afterward, after cleaning up in my hotel room, I ran into Jason at the post-conference mixer. I just stayed in touch with him. We had a phone call a couple of years after that, I think it was. And then, what was it? Six months ago, he was in town speaking at a Small Giants conference.

Wailin: [00:20:25] Oh yeah, sure. Small Giants.

Andy: [00:20:26] Small Giants is a really cool little community. Um, so we did the buses for this conference.

[00:20:30] Jason saw the buses operating and all this and he was like, “Hey, are you here at the conference? Are you coming?” And I had completely forgotten that it was that day. And so I was like, “Yeah man, totally. I’ll be right there.” And threw some clothes on and ran out there. I caught him up on, like, what we had been working on with the bus co and my projects and some of this other stuff in the nonprofit. And I think that’s how maybe he got the idea that maybe I’d be a good fit for this. Because at the end of the day, the Detroit Bus Company on paper is just a bunch of old school buses in a financially failing Midwestern town.

[00:21:11] But when you look at our story, which I think we tell really well, and you look at what our mission is and why we do what we do, then it becomes important. It’s a bunch of people sort of rowing the same direction to try to make this funny, weird thing happen. I’m only guessing here, but if I could pull that off, then, maybe I could tell some pretty good stories here at Basecamp.

Wailin: [00:21:34] Well, thanks for telling your story right now on the pod.

Andy: [00:21:36] Yeah, you bet.

[00:21:36] Broken By Design by Clip Art plays.

Shaun: [00:21:45] Rework is produced by Wailin Wong and me, Shaun Hildner. Our theme music is Broken By Design by Clip Art. You can find show notes for this episode and you can follow us on Twitter @reworkpodcast.

Wailin: [00:21:58] Rework is a podcast by Basecamp. Basecamp puts everything you need to get work done in one place. It’s the calm, organized way to manage projects, work with clients and communicate company wide. Sign up for free at