The 2014 StartupBusNYC team. Five startups had been formed by the time this picture was taken, just two hours into the trip.

StartupBus 2016: What to Expect

Updated May 1, 2016 | Also posted at New Worker Magazine

In 2014 I participated in the madcap hackathon roadtrip known as StartupBus. In each participating city, 30 people get on a charter bus, break into teams and spend three days building apps and forming startup companies. This year, buses from seven North American cities will converge for a final pitch competition during Boulder Startup Week in May 2016.

The week leading up to my trip on StartupBusNYC, I tried to prepare myself by reading a couple blog posts from people who had gone the year before. The advice was relatively perfunctory: bring snacks, USB drives, a mifi hotspot. What I really wanted to know was what the hell am I getting myself into.

If you’re reading this, you’re likely considering whether to go or you’re preparing for the unknown. Here I’ll address non-technical pre-departure concerns and will try to paint a semi-objective picture of what it’s like to be there.

You will be changed

Even if you’re a veteran of hackathons, this is something different. Between the breakneck pace, the lack of sleep and the immersive totality of the experience, this trip is a cultish baptism by fire. I went into it skeptical but came out a true believer.

Expect the unexpected

Typically five or six teams are formed on each bus, and the majority of your time will be spent in the bus working intensely with your team, then squeezing in a couple more hours of work in your shared hotel room. Spending twenty hours a day with your team and your laptop — that much is a given. The rest is not.

For one, the bus will stop for surprise events. Most often they’re a zany cross between a professional development workshop and one of those wacky kids’ contest shows like Nickelodeon Guts. I’ve never used the words wacky and zany in a sentence before because they’re ridiculous, but here they’re accurate. On day two, our mentors woke us up at 5 a.m. and told us to dress up. Only when we were all corralled onto the bus were we told that we’d be deposited at Georgia Tech in 20 minutes and would have to pitch our less-than-one-day-old companies to a panel of actual investors. Everyone snapped from sleep mode to startup mode as we clamored to turn our pitches into something legit. Twenty minutes later we shuffled our bedraggled teams up to a podium and tried not to make complete asses of ourselves as we answered genuine questions as to our companies’ future. Later that day we stopped for lunch at a mall along the highway where we took over a carousel and ran around an arcade playing Dance Dance Revolution and shooting each other with plastic rifles. Random things like this happened often enough that I started to feel I’d been cast against my will on some reality show, a show that tried to jazz up the dull visual image of people at laptops by subjecting them to a carnival of absurd experiences, some serious and some just silly. Being in my thirties, all this had a summer camp-like wholesomeness to it which only added to the absurdity. By the fourth day I wouldn’t have been surprised if we’d had to jump headfirst down a slide and get slimed, or walk an actual tightrope, or at least take a cream pie to the face.

The days on the bus are long by any account. By law the bus driver is supposed to get eight hours of sleep, but this had little bearing on how much sleep any of us got. From what I saw, only the bus itself had eight hours of downtime. Arriving at the hotel late into the night, the process of simply checking in could take hours (isn’t there an app for that?). Before we could shuffle off to sleep, our mentors would have each team come by to pitch and get critiqued, and then we’d do more of the same during breakfast the next morning. Hours for sleep were cut down to about four per night, maximum. Adrenaline kept most teams working late into the night anyway. On the night before the final competition when everyone was on their last legs energy-wise, most everyone still managed to pull an all-nighter. I clocked forty-five minutes of sleep myself, and later in the day slept standing up. The bus part of the trip is like finals week in college: an overabundance of coffee preceding an overabundance of alcohol.

The packed schedule plus the pressure to create your product, reach your milestones, and perfect your pitch, is intense. In this way, StartupBus is actually more like a presidential campaign trail. One of the charter buses on the trip was even used by the Mitt Romney campaign a few years back.

Amid all the intensity, shit will go wrong. Our bus got stuck on an iced-over highway and we collectively had to scramble to change our route. It was freezing. We ate through our provisions. Evening turned to night and we were still stuck. A pregnant woman hobbled across the ice and begged entrance onto the bus to use our toilet. It was half Silicon Valley, half Ice-Road Truckers.

In those hours where we bitched and moaned, something else was happening. It is in social situations like these that deep and lasting bonds are formed. The trials and tribulations of summer camp, or college, are condensed into three intense days. It’s like a pressure chamber for making friends.

It’s like a pressure chamber for making friends.

For adults, social situations like this are exceedingly rare. This is the real reason why StartupBus is an amazing experience. Even if it is kind of a shitshow, or at least a shit reality show.

Now for some advice.

Just fucking go

Having the opportunity to go on StartupBus is a privilege. Even still, I didn’t know if I could swing it, or wanted to. My given reason at the time was “I’m too thirty for that,” but my real reason was a combination of opportunity cost (a whole week away from my fledgling business), real costs (the $300 fee, hotels, a flight back) and good old fashioned fear: I was only a recent entrant into the world of web design and development, the skill set I would ostensibly be bringing to the table, and I was intimidated by the caliber of the other participants. Thankfully I ignored these concerns and just went for it.

Attend an alumni panel

I shoved my trepidations aside after attending two alumni events where I met some former buspreneurs who ticked my same boxes: non-twentysomethings, non-whites, women, and people that weren’t hardcore technical geniuses.

The events went a long way in convincing me. The alumni clearly had a cohesive community going and it seemed like a pretty cool bunch of people. I mean, who wants to spend 72 consecutive hours geeking out over a new project with a bunch of strangers, stopping off in places like Roanoke and Tuscaloosa? That adventuresome spirit isn’t just for the young and crazy, and it’s not just for nerds. It’s for good-natured, curious people who like to try new shit and put themselves to the test. That’s my kind of people.

Plan to stick around afterward

If you aim to keep costs low, you could head home immediately after the competition in Boulder and skip the festivities altogether, but I would highly advise against this. The year I went, StartupBus convened in time for SXSW in Austin, and though Boulder is quite different, it’ll be worth it.

Don’t underestimate the fact that you’ll have just bonded with 30 new friends. Everyone will be hanging out together after going through a crucible of stress and hard work. Join in already. I’m fairly good at being a curmudgeon and I still was inspired to yolo it up all over town.

Expect that you’ll want to stay to bask in the post-StartupBus glow. Kevin Galligan, a 2012 buspreneur and 2014 judge of the final competition, said that simply wearing his StartupBus hoodie around town served to help him make connections with people from other buses. These are your new friends, too, if you stick around to spend time with them.

Last year, most of us stayed an extra few days after the final competition, making for a week-long trip in total. Fuck it, it was the most fun I had all year.

Book your stay immediately

Organize shared housing with your busmates as soon as you know you’re going. With lots of people coming into town at the same time, you will want to act quickly if you want to find an Airbnb or hotel room, let alone one that’s close by and not outrageously overpriced.

I went ahead and booked an Airbnb house before I even knew who would join in. Even still we ended up with a run-down place that was far away — and far from cheap. But it worked out. By the time we got there, all six people who wanted to stay had already ponied up their share and four more wanted to glom on at the last minute.

Get a place that’s within walking distance. You’ll want to be in and out regularly because of the timing of events, meeting up with different people, and the fact that your tired ass will want to sneak in a daytime nap every chance you get.

Some people found cheaper hotel rooms further away but it put a damper on their social life. Going out is the reason for going at all, so do it right.

99 problems but a pitch ain’t one

Aside from logistics, there are other important things to prepare. Here’s a big one: in the weeks leading up to the trip, think about a product idea you might like to pitch.

“Everyone pitches” was a common refrain. Not only does this mean that everyone on a team is expected to get up and practice their pitch regularly, it also meant that everyone had to pitch an idea when we first boarded the bus. This increases the “we’re all in this together” feel and also makes sure that lots of ideas are floating around when it comes time to form teams.

Some people who prefaced their pitch with “I didn’t expect to share this, but…” ended up forming a team around their idea. Bonus points for well thought out concepts: Madelena Mak, a top designer, passed out slick illustrated booklets when she pitched her idea for MiniMap. Not only did she pull a fantastic team together, the team made it all the way to the finals.

Study up on your teammates before you meet them

This may seem a bit of an odd suggestion insofar as it’s creepy to internet-stalk your future busmates before seeing them IRL, but come on, that’s what the fucking internet is for. Before the trip, the StartupBus website publishes brief bios of each buspreneur, accompanied by a photo and short list of each person’s skills. One night before the trip I sat at a bar and read through everyone’s bio.

The next day when I met my future busmates at a pre-trip party, I already had a leg up and was able to start matching faces to names. It helps because you have to act fast to meet so many new people. Knowing each person’s skill set can also give you an edge when it comes time to form teams.

Don’t bother comparing yourself to others

To be honest, I worried that my skills would not be on par with my fellow buspreneurs. For fuck’s sake, I’d already been designing and building for clients for years, but then again I didn’t have a solid idea of where I stood. When you work for yourself, no one gives you a promotion or pats you on the back. Earning a living and having happy clients is one form of proof, but if you work alone you don’t often get to see how you stack up against others.

Given that each participant is expected to fill one of three roles — developer, designer, or “hustler” (i.e. business development) — if my skills weren’t sufficient I might end up being a lame teammate, or worse, a dead weight. As a conscientious and empathetic person, that was an awful prospect to consider.

I may have had a double anxiety about this, as a female and as someone whose design and development skills were entirely self-taught. Call it gender-related performance anxiety. Anyone would be embarrassed if their skills didn’t cut it, but since the tech world of hackathons and startups is dominated by “rockstar” programmer dudes, the possibility that I might not “deserve” to be there haunted me. As a woman, the implication of getting somewhere not based on merit is particularly mortifying and insulting. Part of the reason I became a freelancer and a business owner in the first place was so that I could work more on my own terms and not have to think about that crap.

Imposter syndrome — the feeling that you may be unmasked as a fraud — is a common one when you contend with groups of high-caliber professionals who demonstrate their value in a competitive and public way. I’m harping on this point because I eventually found there were a number of others who felt unsure as well—and I should note that those people were all top shelf talent. I also bring this up because in life I’ve seen people drop out because they didn’t think they could contend. Fuck that. Do some shadow boxing and then get your ass in the ring.

When you’re self-taught and work alone, there’s a lot of shadow boxing. StartupBus is full of people who regularly do hackathons, but for me it was the first time I worked on an app with other people. Seeing just how much developers Google their way through problems — that alone was worth the price of admission. The simple experience of watching how other people actually work gave me a lot of context, and more confidence.

Your teammates will be rad

It quickly became obvious that each person brought to the table more than just their raw skills, and some of these things made all the difference. Domain expertise, humor, willingness to get up and talk in front of a crowd: anything you have, you’ll use.

My team consisted of two designers and four developers, so we sometimes split things up. One developer who also had film editing experience made a video for our landing page. Another developer doubled as a data scientist. I shifted over to “hustling” and PR when I saw that the other designer had our bases covered. But another way of looking at my team was that we had a jokester who was great for morale and a couple indefatigable team members to rope us all back in. For a three-day competition, that mattered a lot more than who had the dopest Javascript skills.

Alternately, if your skills are best used elsewhere, you can always switch teams. When you belong to a good community there will be a place for you. If you’ve been asked to belong to this community, don’t second guess yourself—you’re a good fit.

It’s less a competition and more a collaboration

Technically StartupBus teams compete against each other, particuarly against the teams from other buses. But that’s just the grand finale, and while it’s intense, it’s done in good humor. Everything leading up to that is highly collaborative, though it uses the language of competition. I found the whole experience to be much more about cooperation than about fighting to win.

This is a key facet of the entire StartupBus organization. It’s run by people who participated in years past and the community aspect is deeply reinforced. It’s evidenced by the tribal affinity you develop with your teammates and it continues long after you get back. On the whole, the StartupBus experience is distinct in its dedication to building and maintaining a strong community.

Be ready to form a team, fast

The question of how exactly teams get formed was brought up by a lot of us before we got on the bus. The answer is that it happens insanely fast — in literally a matter of minutes. Before our bus made its first stop for a coffee break, teams were already formed and hard at work. It seems like not nearly enough time to make sure you have the “right” team. But what do you expect when you’re supposed to have a product by the end of the first day?

“Before our bus made its first stop for a coffee break, teams were already formed and hard at work.”

Here’s how my team, Datalize.me, was formed. I heard a pitch from Anna Nicanorova about a “personal API” that would allow people to pull their personal information and content on Facebook, Foursquare, Fitbit, etc., perhaps to remove it, or to make it portable for use in other apps or compile it for data visualizations. The idea fairly blew my mind — is it even possible to do that? — so when we all broke to form teams, I sought her out. The conversation got quite involved as it spread to include nearly everyone within earshot standing there in the bus aisle, and in our mutual enthusiasm we all decided to give it a go. Just like that our team was formed and our project was defined, all in about two minutes flat.

It’s a bit like musical chairs. The only difference is no one gets left out. Our team started with a gargantuan seven people, and later in the day one of our own, Nicole Dominguez (who had even chosen our company’s name) switched to another team that needed her formidable design skills. There is inevitably some shuffling but from what I could tell everyone was really pleased with their team.

Yes, teams did tend to form around shared competencies: some Android developers stuck together; my own team had Ruby on Rails in common. But some teams were a totally mixed bag and relied on one developer to build the product.

Know your goals

Looking back, forming a great team is less about skill sets and more about mutual passion for the idea, a sense of humor, and shared goals. When I say shared goals, I expecially mean the goal of winning, or of not caring about winning. Not all girls just wanna have fun: some people want to find a project that lets their skills stand out in a big way. At the same time, plenty of people don’t give a shit about making it to the finals. If some people on your team are intent on winning and others aren’t, that could be a schism that disappoints and stresses everybody out.

“Forming a great team is less about skill sets and more about mutual passion for the idea, a sense of humor, and shared goals.”

While StartupBus is ostensibly an opportunity to form a real company, this is not an explicit goal for most participants. That doesn’t mean there aren’t some big successes. Instacart was formed by buspreneurs; Lisnr was created on the Midwest StartupBus. Smart Host was the 2014 winner and months later was admitted to TechStars. They’re still a company over a year later, proving that a killer team #cantstopwontstop.

Salman Ansari, an entrepreneur who had built and sold a company before getting on the bus, said he joined “for shits and giggles.” It’s fair to say he was not alone. I myself joined because I thought three days of making friends and working on something new would be a lot of fun regardless of the results. And it was, particularly because my team was all on the same page—we just really loved the concept we were working on.

You’ll suffer, but you’ll like it

Whether it’s the sleepless nights, the exhaustion, the pressure, the stage fright, the bus toilet, or the weak hotel coffee, you will suffer. Like a rough road trip, it all adds up to the kind of fun you have when you don’t realize you’re having fun.

“Like a rough road trip, it all adds up to the kind of fun you have when you don’t realize you’re having fun.”

And then there are the times like when we ran around the Alamo, Pee Wee style, with kids from Mexico’s StartupBus, or when a team from our bus was declared the winner and we stomped and hollered so loud you’d swear we were real Texans at a hootenanny. Even when you’ve lost your ability to keep your eyes open, you still have the capacity for joy. Remember this when you lay your head down to pass out under a table after the final competition.

It will be worth it

Without a doubt, going on StartupBus kicked my ass. I won’t lie: in my first week back I was actually bitter. I thought my mentors had been hard on me, pointing out daunting things that knocked the wind out of my sails. It didn’t help that I also caught a massive cold.

After recovering from sleep deprivation and sickness, I spent time obsessing over my personal successes and failures on the trip. Moments where I was an unflinching bad ass, moments where I let my team down and everything in between. Experiences like these are a proving ground. They’re always rough terrain, but they’re necessary if you want to know the truth about yourself under pressure. If you’re considering a future in startups, this is a great crash course—not in how to build a company, but in how to deal with yourself and others in a high-pressure environment.

“If you’re considering a future in startups, this is a great crash course — not in how to build a company, but in how to deal with yourself and others in a high-pressure environment.”

My biggest takeaway was realizing how much shit you can get done in 72 hours. Yeah, our prototype was wonky. But we had the avid interest of experts who wanted to join in. We had press. We had momentum. And we had all this because we sat down together for three days and made it happen.

Upon my return, I couldn’t help but look at my yawningly unfinished projects with a critical eye. I saw that my future would remain on idle as long as I let it, but that I could break out with some down-and-dirty intense work. Within two months of returning, I founded and launched a publication; within six months I pivoted my company and launched a new product. It’s been a year since I got on the bus, the most successful year of my life.

Oh, yeah, and I have 30 new friends who are fucking excellent—smart, successful, capable, connected, helpful and cool as fuck. I’ve collaborated with some, gone on trips with others, and celebrated with all of them. That alone made it worth it.

Other resources to help you prepare for StartupBus

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