I’ll repeat what this post’s title is telling you: Everything you need to know in order to win StartupBus North America 2022 is contained within a podcast. More specifically, the “Startup Bus” series of episodes from Gimlet Media’s Startup podcast, which covered the New York bus’ journey during StartupBus 2017.
This five-part series covered the journey from its start in New York City to the finals in New Orleans. It features reporter Eric Mennel, who “embedded” with the StartupBus New York bus in July 2017 to follow the participants, talk to them, and report on what happened. It gives you a look not just into the teams and their projects, but the people in those teams, what drives them, and the very personal reasons why they chose to go on the bus.
Rule number one of StartupBus is that there is no “number two” on the bus. Bus toilets aren’t as well-sealed as airplane toilets, and if you poop on the bus, it will be bad for everyone concerned — especially you, because we’ll all be giving you the stink-eye from now on.
You’re going to make your first pitch very soon after the bus departs. At the start of the ride, every buspreneur stands in front of the bus and makes a first pitch. This pitch will be for two things:
Yourself: You’ll be selling yourself to prospective teams. You’re going to need to convince people why you should be on their team or why they should be on yours. It works best if you can have your unique value proposition ready in advance.
Your startup idea:If you have a startup idea — that is, if you have a problem and a solution — you should be ready to pitch it. You want your fellow buspreneurs to want to work on your startup idea!
Be ready for chaos after the first pitches. After the pitches, people will start looking for and forming teams. Be ready to move about the bus to talk to different groups.
Build a balanced team. You’re going to need a variety of skills to get the job done in three days.
Day one of StartupBus is about coming up with and validating your idea. Your idea will be tested, and you may need to modify it slightly — or make a big pivot. Be prepared to do either.
There’s a difference between a technology and a solution. One of the teams that initially looks like a collection of all-stars ends up without a product idea because they were focused more on blockchain than a solving a problem with blockchain. As the saying goes: “People don’t really buy drills, they buy holes.”
If the technology you plan to use isn’t something laypeople are familiar with, you may need to spend some time explaining it. The blockchain team ended up spending a lot of the time allotted to their pitch explaining what a blockchain was, and why it might be essential to the problem they hadn’t quite settled on solving. Remember, this was 2017, well before the time when crypto exchanges were easy to find online and celebrities were shilling for cryptocurrency companies; in fact, it would be a little bit before “BitConneeeeeeeeeeect!”. Keep this is mind if your startup is going to be NFT-based — you’re going to spend a good chunk of your pitch explain them to the judges, which will take away from the time to pitch what your project actually does.
The conductors are there to help you. Not only that; all the conductors have been on StartupBus before, so we’ve gone what you’re going through now, we learned from our experiences, and we’ve internalized those lessons. Our job is to actively help you make your startup, project, and pitch be the best they can be.
The conductors are there to challenge you. The ride to Austin will not be direct. There will be stops, where you will face challenges. A mere 4 hours after the New York 2017 bus departed, the teams had to make their first pitch in front of a panel of judges in Washington, D.C..
Try to avoid talking over other team members. Day one is about initial ideas and refinement, and there’s a lot of talking and brainstorming. Your team should try to make sure that team members don’t talk over other team members.
Find out why your fellow buspreneurs are there. There are all sorts of reasons why someone would go on StartupBus, but there are a few particular categories of “why” that you’ll definitely see:
Seekers: There are always a number of buspreneurs who are participating because they’re looking for something: options for a new career path, new perspectives, new experiences, a chance to see parts of the country they otherwise wouldn’t see, and meaning. They can be great “idea” people, as they’re on the bus with the specific goal of trying new things.
Shakers: There are also always buspreneurs who want to “shake up” their current situation. Perhaps they’re in a job or life situation they don’t like, feel they’ve fallen into a rut, or want some experience that will set them apart from other job candidates (this is one of the reasons I went in 2019). These are great “doers,” because their reason to be on the bus is to do new things.
Hackathon junkies: Just as there are people who regularly compete in marathons and triathlons, there are people who regularly compete in hackathons (and remember, that’s what StartupBus is). Having one on your team is a real help — they have experience delivering a proof of concept in short order.
Watch this blog for the next episode, and my notes from that episode!
Five years ago today, I submitted the first of two programming assignments as part of a job interview with a company that makes applications for the trucking industry.
May 2017
My interview at the company’s head office is going well. I’m giving them my Q&A A-game, the back-and-forth is flowing smoothly, and my knowledge of the trucking industry and lore — a combination of having done some research as well as repeated listenings to the Mark Dalton, Trucker/Detective audiobook series — seems to be paying off.
Ninety minutes into the one-hour interview, the CTO puts the brakes on the conversation and proposes a next step.
“We like your breadth of experience,” he says. “Now we’d like to test your depth. If we gave you a quick programming assignment, which would you prefer — writing an iOS app, or an Android app? You should go with the one you’re stronger in.”
I’m a much stronger iOS programmer than an Android one. The smart move would be to answer “iOS,” and be done with it.
But in that moment, I remember the motto: Be like Han.
Instead, I reply “Yes, but you’re looking for someone to lead a team of both iOS and Android developers. You really should give me both.”
The CTO raises an eyebrow, makes a note on his pad, and says “Hmmm…I think I will.”
This is either a “total baller move” (to borrow a turn of phrase the kids are using these day), or the end of that job prospect. But for the job that they’re trying to fill, taking on that challenge was the right thing to do.
I leave the interview with just one thought: Good thing I don’t have a job. This is going to be a lot of work.
The app
I decided to tackle the iOS version first. The tricky part was that the assignment required that the app be written in the old iOS programming language, Objective-C. In 2017, Swift had been around for 3 years, so it was still reasonable to expect to do some Objective-C development.
I made the leap to Swift as soon as it came out, so it had been 3 years since I’d done any Objective-C coding. It took me a couple of hours to regain my “C legs,” but after a few days’ work, I managed to come up with this app:
Now I’m in the position where I am handing out programming assignments to prospective employees. I keep my 2017 experience in mind, which means:
I try to be respectful of their time. The assignment should be detailed enough to provide a realistic picture of the the candidate’s abilities but not so complex that they have to drop everything — including home/family responsibilities and their current job — to be able to complete it.
I try to be open to communication and responsive. I never want them to have that “ghosted” feeling I got five years ago.
PyCon US 2022 is happening this week, with tutorials happening on Wednesday and Thursday, and the main conference starting on Friday and running through the weekend. It’s Python’s largest conference, and according to the venue’s events calendar, almost 3,500 people are expected to attend!
I’m sure that you’ve perused the schedules and picked out the ones that you’d like to attend (and hey, be sure to check out my teammate Jess Temporal’s talk on JSON Web Tokens — a.k.a. JWTs — on Saturday at 11:30 a.m. in room 255DEF). Or perhaps you plan to hit some booth on the Expo floor (come by the Auth0 booth — I’ll be there!).
But have you planned out how you’re going to work the room?
What is “working the room?”
It’s been my experience that some of the most important things I’ve learned and all the connections I’ve made at conferences didn’t happen at the presentations. Instead, they happened between presentations — in the hallways, lounges, lunches, and social gatherings, where I had the chance to chat with the speakers, organizers, and the other attendees. This observation is so common that it’s given rise to “unconferences” like BarCamp, whose purpose is to invert the order of things so that the conference is more “hallway” than “lecture theatre”.
It’s especially important to talk to people you don’t know or who are outside your usual circle. Books like The Tipping Point classify acquaintances with such people as “weak ties”. Don’t let the word “weak” make you think they’re unimportant. As people outside your usual circle, they have access to a lot of information, people, and opportunities that you don’t. That’s why most people get jobs through someone they know, and of those cases, most of the references came from a weak tie. The sorts of opportunities that come about because of this sort of relationship led sociologist Mark Granovetter to coin the phrase “the strength of weak ties”.
The best way to make weak ties at a conference is to work the room. If the phrase sounds like sleazy marketing-speak and fills your head with images of popped collars and wearing too much body spray, relax. Working the room means being an active participant in a social event and contributing to it so that it’s better for both you and everyone else. Think of it as good social citizenship.
If you’re unsure of how to work the room, I’ve got some tips that you might find handy…
Have a one-line self-introduction
A one-line self-introduction is simply a single-sentence way of introducing yourself to people you meet at a conference. It’s more than likely that you won’t know more than a handful of attendees and introducing yourself over and over again, during the conference, as well as its post-session party events. It’s a trick that Susan RoAne, room-working expert and author of How to Work a Room: The Ultimate Guide to Making Lasting Connections In-Person and Online teaches, and it works. It’s pretty simple:
Keep it short — no longer than 10 seconds, and shorter if possible. It’s not your life story, but a pleasantry that also gives people just a little bit about who you are.
Make it fit. It should give people a hint of the cool stuff that you do (or, if you’re slogging it out in the hopes of doing cool stuff someday, the cool stuff that you intend to do.)
Show your benefits. Rather than simply give them your job title, tell them about a benefit that your work provides in a way that invites people to find out more. Susan RoAne likes to tell a story about someone she met whose one-liner was “I help rich people sleep at night”. That’s more interesting than “I’m a financial analyst”.
My intro will be something along the lines of “I’m a rock and roll accordion player, but in my side gig, I’m a developer advocate for an incredibly cool company that helps make logins happen.”
How to join a conversation
At PyCon, you’ll probably see a group of people already engaged in a conversation. If this is your nightmare…
…here’s how you handle it:
Pick a lively group of people you’d like to join in conversation. As people who are already in a conversation, they’ve already done some of the work for you. They’re lively, which makes it more likely that they’re open to people joining in. They’ve also picked a topic, which saves you the effort of having to come up with one. It also lets you decide whether or not it interests you. If they’re lively and their topic of conversation interests you, proceed to step 2. If not, go find another group!
Stand on the periphery and look interested. Just do it. This is a conference, and one of the attendees’ goals is to meet people. Smile. Pipe in if you have something to contribute; people here are pretty cool about that.
When acknowledged, step into the group. You’re in like Flynn! Step in confidently and introduce yourself. If you’ve got that one-line summary of who you are that I talked about earlier, now’s the time to use it.
Don’t force a change of subject. You’ve just joined the convo, and you’re not campaigning. Contribute, and let the subject changes come naturally.
Feel free to join me in at any conversational circle I’m in! I always keep an eye on the periphery for people who want to join in, and I’ll invite them.
More tips
Here’s more advice on how to work the room:
Be more of a host and less of a guest. No, you don’t have to worry about scheduling or if the coffee urns are full. By “being a host”, I mean doing some of things that hosts do, such as introducing people, saying “hello” to wallflowers and generally making people feel more comfortable. Being graceful to everyone is not only good karma, but it’s a good way to promote yourself. It worked out really well for me; for example, I came to the first DemoCamp (a regular Toronto tech event back in the 2000s) as a guest, but by the third one, I was one of the people officially hosting the event.
Beware of “rock piles”. Rock piles are groups of people huddled together in a closed formation. It sends the signal “go away”. If you find yourself in one, try to position yourself to open up the formation.
Beware of “hotboxing”. I’ve heard this term used in counter-culture settings, but in this case “hotboxing” means to square your shoulders front-and-center to the person you’re talking to. It’s a one-on-one version of the rock pile, and it excludes others from joining in. Once again, the cure for hotboxing is to change where you’re standing to allow more people to join in.
Put your coat and bag down. Carrying them is a non-verbal cue that you’re about to leave. If you’re going to stay and chat, put them down. When you’re about to leave, take your coat and bag and start saying your goodbyes.
Show and tell. We’re geeks, and nothing attracts our eyes like shiny, interesting pieces of tech and machinery. It’s why I carry my accordion around; I think of it as a device that converts curiosity into opportunity (and music as well). I’ll be doing the same with my iPhone and ARKit apps as well! Got a particularly funky laptop, netbook, smartphone or new device you just got from ThinkGeek? Got a neat project that you’ve been working on? Whatever it is, park yourself someplace comfortable in the hallway, show it off and start a conversation!
Save the email, tweets and texts for later, unless they’re important.They’ll draw your attention away from the room and also send the message “go away”.
Mentor. If you’ve got skills in a specific area, share your knowledge. Larry Chiang from GigaOm says that “It transitions nicely from the what-do-you-do-for-work question. It also adds some substance to party conversations and clearly brands you as a person.”
Be mentored. You came to RWDevCon to learn, and as I said earlier, learning goes beyond the sessions. One bit of advice is to try and learn three new things at every event.
Play “conversation bingo”. If there are certain topics that you’d like to learn about at PyCon, say ARKit, Android, architecture, and so on, put them in a list (mental, electronic or paper) of “bingo” words. As you converse at the conference, cross off any of those topics that you cover off the list. This trick forces you to become a more active listener and will help you towards your learning goals. Yelling “BINGO!” when you’ve crossed the last item on the list can be done at your discretion.
I’ll see you at PyCon, and if you see me or anyone else on the Auth0 team, please say “hi” — we would love to meet you!
Come drop by the booth — we should be pretty easy to find. Just listen for the accordion.
My history with Python
Toronto programmer D’Arcy Cain was looking for a programmer to help him develop an ecommerce site for a client. At the time, the stack that web developers needed to know was LAMP — Linux, Apache, MySQL, and Perl (later expanded to include other languages whose names start with “P”). D’Arcy’s preferred stack was BSD, Apache, Postgres, and Python, which at the time was considered to be a contrarian choice.
He asked if I was willing to learn Python, and I said “Sure! I can pick it up after I get back from Burning Man, on the first day after Labor Day…”
He said “No — I need you to hit the ground running on the first day after Labor Day.”
And I said, “All right. I’ll make it happen.” So I packed my laptop and a copy of O’Reilly’s Learning Python and took it with me to Black Rock Desert.
Since Burning Man is more of party-all-night place, it can be quite peaceful in the morning. The rental RV that I shared with San Francisco-based artist David Newman and our friend Nancy was an oasis of calm with a good generator, and I was able to spend a couple of hours a day going through Python exercises, catch a nap, and then strike out onto the playa in the afternoon for the next evening’s mayhem.
By the time I got back to Toronto, I was ready to start coding in Python, and a descendant of that original site and its business still exists today. I figured that any programming language you can learn at Burning Man has to be good, so I’ve been using it to get things done since then, including putting together the Tampa Bay tech events list that appears on this blog weekly.
In spite of my long-time use of Python, even during that period when Ruby was ascendant thanks to Rails, I’ve never gone to PyCon — until now. I’m looking forward to it!
After the great interruption of 2020 and 2021, North America’s largest, longest-distance hackathon, StartupBus North America, is back for 2022! From July 27th through 31st, 2022, seven buses will depart from seven locations across the continent…
…and make their way to Austin, Texas in three days. During those three days, “buspreneurs” — StartupBus’ term for its participants — think up and build a tech startup from the ground up: the idea, business plan, software, and pitch.
One of the seven buses making its way to Austin over three days is the Florida bus, and it’s leaving from Tampa. This year, one of the Florida bus’ conductors — StartupBus’ term for its coaches/facilitators — is…Yours Truly!
🚨 Keep reading: later on in this article, there’s something that I’ve never told anyone online until now.
I was on StartupBus in 2019
I was a “buspreneur” on the Florida StartupBus in 2019, the last year the event took place, when the destination city was New Orleans. Along with my teammates Rina Bane, David Castaneda, Justin Linn, and Tracy Ingram, we made it all the way to the finals and got the runner-up position.
The startup we created on the bus was Hyve, a service that lets you create virtual disposable email addresses that you can use when subscribing to services or communicating with untrusted people.
Rather than provide a service or person with your real email address, you use Hyve to generate a disposable email address to give to that service or person, and it forwards emails sent to that disposable email address to your real email address.
What happened on StartupBus Florida 2019?
It started with a get-together the day before we boarded the bus, which was captured in this ABC Action News piece:
As you may have guessed, we spent a fair bit of time coding and designing the service…
…but at the end, we present our startups to panels of judges, so we also spent a lot of time working on our pitches. We did so many practice pitches on the bus, followed by feedback from the conductors and our fellow buspreneurs, including this one by Tracy:
Just as startup life is full of unpredictable events, StartupBus is designed to mirror that unpredictability. For starters, we only knew that the destination was New Orleans, and that it would be a roundabout one so that it would take three full days. I pieced together the route shortly before we arrived:
We knew that there would be stops at night for hotels as well as other places, but we didn’t know where or when.
Our first non-meal/gas/bio-break stop happened in the late afternoon of Day 1 when we visitied the Entrepreneurship Garage at NC State University in Raleigh, North Carolina. It let us get more work done in a stationary place with access to more guidance, better internet connectivity, more reliable power, and (very importantly) bathrooms. It’s where we recorded this mandatory “Why are we on the bus?” video at the end of Day 1…
…and it gave us a chance to refine our pitch by trying it out on non-bus people, such as the Lyft driver who took us from the Entrepreneurship Garage to our hotel:
Day 2 gave two buses a surprise: upon our departure from Raleigh, the Florida and DC buses merged to become the Swamp Thang bus!
Now we had a full ride:
We got to know the folks from DC, and the spirit was one of “coopetition” — we knew we were all competing against each other, but we also made friends and even helped each other out. I ended up spending a little time helping a DC developer with a bug in their Flutter project.
We had a stop at Advent Coworking in Charlotte, North Carolina, where our bus met up with the New York bus, and some of us (time was limited) got to do our first pitches in front of a panel of judges.
There were also the “unexpected unexpected” events — the unexpected events that the conductors didn’t plan. There was the time our bus got stuck on one of the oversized speed bumps at NC State:
Our big “unexpected unexpected” happened when the bus overheated and had to pull over on the highway somewhere in the mountains in Tennessee:
This delay meant that getting to the next stop meant staying on the bus well into the night:
Day 3 was a long, hard drive with a lot more pitching, designing, coding, and reaching out to prospective business partners and customers (yes, you have to treat your bus startup just like a “real” one!), but at long last, we arrived in New Orleans:
Which brings us to Day 1 of two days’ worth of pitch competitions: the qualifiers.
All our previous pitches were mere rehearsals. This pitch would determine if we would get into the semifinals!
Here’s our qualifying pitch:
We continued working into the night of Day 1, refining the code and pitch. We wouldn’t find out who would make it into the semifinals until Day 2 — and we did!
So we worked on our pitch and code, bringing in Andrew Romaner as a consultant (remember, you’re running like a real business, so you can get consultants if you have the connections!)…
…and made it to the finals!
So we worked some more…
…which led to our final pitch:
Once all the finalists made their pitches, the judges sequestered themselves, and shortly afterwards, they made their announcements, which included Hyve!
Just because I love that bit about walking the line between good and evil, here’s just the part about Hyve:
Let me be very clear: StartupBus offers no prizes of any sort. No cash, no prizes from sponsors, not even a trophy or certificate. In fact, you’ll spend money in the process, including getting home (the bus gets you to the destination city, but you have to make your own way back).
So why do it? Because what you gain from StartupBus is more valuable in the long run than mere coin or prizes: experience.
It’s one thing to be an employee working from home or in an office. It’s an entirely other thing to be a startup founder — even for less than a week’s time — collaborating closely with people you’ve known only for hours, on a bus, where the power and internet are unreliable, and dealing with the curve balls that the conductors and the vagaries of the road will throw your way.
Something I’ve never told anyone until now
There are more comfortable things that you could do with your time, but I remind you that the magic happens outside your comfort zone.
Here’s something I’ve never said online until now: I was fired from my job in June 2019. But rather than cry in my own beer and wonder how I’d explain it to prospective employers, I decided to shake things up.
My plan was simple:
Join StartupBus, which was happening in July 2019.
Winning or at least be a finalist.
Parley the victory and experience into my next job or a new company.
Simple? Yes. Easy? Most certainly not. But extraordinary outcomes need extraordinary effort, and StartupBus definitely falls in the “extraordinary effort” category…
…especially since one of the judges in the finals was the CEO of the company that fired me. We’re on good terms, but if I can pitch under those circumstances, I can pitch anywhere, anytime, anyhow. I knew it was going to happen if I made it to the finals — in fact, I was counting on it.
StartupBus gave me the opportunity to gird my grit, sharpen my software skills, and polish my personal pitch. I’ve taken my experience on the bus and used it to get to the rather nice place where I am today.
After StartupBus, I contacted Trey Steinhoff, a buspreneur from 2017. He and Robert Blacklidge created Course Align, which grew into a real business beyond the bus. Trey was Director of Product at Lilypad at the time, and they were looking for a mobile developer.
“Why just take on any mobile developer, when you can get one who’s also been on the bus?” I asked, and got hired. It turned out that Akira Mitchell, one of the conductors on StartupBus Florida, was a scrum master there! I remember telling Akira “You know, it’s so much easier working with you at actual desks in a stationary office than on a bus bouncing all over the road while the wifi’s going in and out.”
I got to go places I’d never seen or place I hadn’t seen in a while. I got to get to know some friends better, and made new ones with whom I’m still in touch today. I got to experience a challenge that most techies don’t take on, and I boosted my “personal brand” at a time when I really needed that boost. StartupBus can pay off big if you harness the experience.
And now, I’m a conductor
A couple of weeks ago, I was contacted about being a conductor. “Your name keeps coming up, over and over again, so — would you like to be a conductor?”
I still have more to experience and learn, and this time, I’d like to do it by helping, mentoring, and guiding buspreneurs on the Florida bus. I owe it to the Tampa Bay and Florida tech communities that have given me so much. And hey, after all this time cooped up, I’m ready for some new road adventures.
Are you on the bus?
As I write this, we’re less than 100 days away from the day the bus leaves Tampa for Austin. The question you should be asking yourself is:
Are you going to be on StartupBus? The Florida bus will depart from Tampa, but there are others leaving on the same date:
The Advancing Black Entrepreneurs bus is one especially for a greatly underrepresented minority in tech, and it departs from Cincinatto, Ohio.
The California bus’ departure point is yet to be determined.
The Latinxs in Tech is another bus for another greatly underrepresented minority in tech, and it departs from Miami, Florida.
The Mexico bus departs from Ciudad de Mexico, a.k.a. Mexico City.
The Texas Bus departs from San Antonio, Texas, and yes, they’re going to plan a route that takes three days.
You can’t just sign up for StartupBus — you have to apply, because we’re looking for people who are determined to create a great startup under sometimes-gruelling conditions and give it their all.
I recently found the video above, which features an ABC Action News story that covered the “Welcome” party held for StartupBus Florida participants on the evening before our three-day bus trip across the southeastern U.S.. It’s been two years since that extended long weekend in late July 2019, and while COVID-19 ended any possibility of safely holding then event in 2020 and 2021, I hold out hope for a StartupBus return in 2022.
The 2019 edition was the 10th annual Startup Bus North America competition, which might be describes as “Shark Tank goes on a road trip”. It’s a competition that takes place on a bus ride where contestants (better known as “buspreneurs”) form teams, ideate, and come up with an innovative technology startup, then build a working application — all in the space of three days. While on a bus.
I could go on about what the team and I did, but I’ll let these videos tell the story instead…
Meet Team Hyve!
Here’s our first team video, which we recorded at the end of Day One of the bus trip at NC State in Raleigh:
Pitching Hyve to a stranger
One of our assigned tasks — on top of building a startup and the application that powered it — was to pitch our idea to a stranger in one of the towns where we stopped. We pitched the Hyve concept to the Lyft driver who took us from NC State to our hotel. Here’s how it went…
Practicing our pitch
In addition to building the business and the app on the bus, each team on the bus practiced their pitches at regular intervals by presenting to their fellow buspreneurs. Here’s Tracy Ingram from Team Hyve delivering our pitch as the bus raced towards New Orleans:
The qualifying round
The qualifying rounds took place on Saturday, July 27th at New Orleans’ Propeller Incubator, where all the teams from all the buses — the Advancing Black Entrepreneurs, Florida, Mexico, New York, Ohio, Silicon Valley, and Washington DC teams — made their pitches.
Every member of every team had to be ready to pitch, because in the qualifying round, the judges chose two people from each team to make their pitch, one at a time. They tend to choose the least confident-looking team members, and a couple of them already knew me. We did well, though, with Rina doing the “set ’em up” pitch and Tracy doing the “finish ’em off” one:
The finals
We’d have to wait until the next day to find out who made it to the semifinals, but we were among them! Even better, we made it to the finals. We re-worked our pitch for the finals judges with the help of the Florida Bus Conductors — Akira Mitchell, Nick Price, and Shane Needham — and here’s the result:
The winners
Once all the finalists made their pitches, the judges sequestered themselves, and shortly afterwards, they made their announcements, which included Hyve!
Just the bit about Hyve
Just because I love that bit about walking the line between good and evil, here’s just the part about Hyve: