My third experiment for 2024 involves trying out the ideas from Noah Kagan’s new book, Million Dollar Weekend.
ℹ️ In case you’re wondering: my first experiment of 2024 was to turn my layoff experience into a series of articles; the second was to take a chance working with a pre-seed startup.
Why conduct such an experiment? For now, let’s just say that current circumstances make it necessary, and hey, if anyone can pull off this kind of thing, it would be me.
The general idea of Million Dollar Weekend is that you can start a lucrative business by doing the following:
Identify a problem that you can solve
Solve that problem in a way that is hard to resist and profitable
Test your solution at low (or no) cost by preselling it before you build it.
The prerequisite for the Million Dollar Weekend process is a certain amount of unmitigated gall. Time and again in the book, Kagan states that two things hold people back from starting businesses:
Fear of starting
Fear of asking
Kagan’s methodology is to start by trying out an idea, seeing if someone will pay for that idea, and then either refining that idea or coming up with a new one and repeating the cycle.
The methodology anticipates rejection, and in fact, it says that in selling your idea, you should aim for plenty of rejections. The idea is that if you’re getting rejected often, you’re asking often, and that’s what eventually leads to success.
I’ll write more as I continue with this experiment, but for now, if you’re curious, here are some resources I can point you to:
You might also find these interviews with Kagan interesting:
ℹ️ Also in case you were wondering: This is NOT a paid promo for the book — neither Noah Kagan nor his businesses have any idea who I am or how to deposit money into my bank account. I wish they did!
Tallahassee is the capital of the state of Florida, and it’s also the home of Domi Station, Tallahassee’s business incubator, coworking space, event venue, general all-round supporter of startups in the area, and friend of this blog (they were a host for StartupBus Florida when we passed through earlier this year). Domi Station is also the home of Startup Week Tallahassee, which happens this week!
And the events are FREE TO ATTEND!
The event is the Tallahassee edition of Techstars Startup Week, a week-long event celebrating entrepreneurship and the startup community. Startup Week features speakers and events to inspire, inform, and introduce people who share an entrepreneurial spirit.
Startup Week Tallahassee 2022 takes place this week, November 14th through 18th at three locations (including Domi Station) and will have 12 tracks focused on different industries:
StartupBus 2022 happens in less than a week! For the benefit of the people who’ll be participating in this mobile hackathon — as well as those who are still thinking about signing up (it’s not too late!), here are some protips that you might find handy.
If you read only one guide for winning hackathons, read this one. Among his tips:
The demo should be the center of your project. Your pitch should revolve around the demo, and the demo should be captivating.
Don’t do “design by committee.” As Nick puts it: “You want to tackle an idea when—and only when—at least one person is a true believer. Going with everybody’s second favorite idea is disheartening and ultimately dangerous.”
Stick with tools you know well and can rely on. You’re under a lot of time pressure on StartupBus, and there are a number of “unknown unknowns” you’ll have to contend with. These challenges will be much worse if you’re using StartupBus as an opportunity to try out new tools — you’ll be climbing up a learning curve while trying to get an application running under tricky conditions.
Ship the MVP. “MVP” in this case means “Minimum Viable Product,” a product that does just enough for customers to be willing to pay for it. Stick to the main functionality, avoid adding unnecessary features, run it locally on your computer if you can, skip or use smiulate login if you can do that, and so on.
StartupBus Florida will provide some utilities and other goodies for anyone who wants to work on a Web 3.0 project. I personally think that Web 3.0 is still a lot of snake oil and NFTs are basically FourSquare mayorships for JPEGs, but others on the team think that it’s the hottest thing of the moment, and I’m here to support StartupBus projects. I leave it to the buspreneurs and readers to make their own call.
There are all sorts of ways to win StartupBus, even if you don’t come in first place, and even if you don’t make it to the finals or even the seminfinals. This article points out different ways of viewing success at StatupBus. Check it out!
Everything you need to know to win StartupBus is in this podcast
Gimlet Media’s Startup podcast sent a reporter to join the New York City StartupBus for the 2017 event, and the result was a five-part series that tells the story of the buspreneurs on that bus.
Before going on StartupBus 2019, I listened to this podcast in its entirety — twice — to get a better feel for what the experience would be like and to try to glean insights into what would give me and my team better odds of winning.
I wrote a five-part series called Everything you need to know to win StartupBus is in this podcast, where I share notes on every episode of the podcast series. Check it out, and learn!
The title of this post should be a big hint: Everything you need to know in order to win StartupBus North America 2022 is contained within a podcast. This is the third in a series of posts covering the “Startup Bus” series of episodes from Gimlet Media’s Startup podcast, which covered the New York bus’ journey during StartupBus 2017.
Did you miss the first four articles in this series? Here they are:
…and here are the lessons I took away from this episode:
A lot of what makes success is just showing up. At the start of the episode, podcast host Eric goes for an early morning walk with Colleen Lavin of team Daisy and discovers that she was nce the Illinois Knights of Columbus free throw champion for girls age 14. Here’s how she tells the story:
COLLEEN: I was like getting my school volunteer hours, helping my dad at the free throw contest, and I was in the right age range, so he made me compete. I made two baskets, because I was not a basketball player. But no other girls in my age range showed up, and he made me go to the next competition and no other girls my age range showed up. Finally, I was almost sent to D.C to compete in the nationals after making a total of like four baskets.
ERIC: Because nobody had showed up?
COLLEEN: In my age competition!
Be prepared for possible twists in the finals.Elias Bizannes, the creator of StartupBus, loves drama. In the 2017 competition, even though there were five finalists, Elias decided to create a sixth team made up of people from teams who didn’t make it into the finals. The team would create a blockchain-powered voting app. Why did he do it? In his own words…
To mess with people to be honest. Because that’s what we do with StartupBus, we push them and we break them. And what happens is this remarkable thing comes out when people go beyond the limits they think they can, they actually step up. And so by introducing a new team, it was gonna add another level of competitive threat to the finals.
The finals will feature far more polished pitches and apps: “From the moment the pitches begin, it’s apparent. This is a very different level of competition than yesterday. The presentations are all well-crafted. Each of the products makes sense. You could imagine people making these pitches to actual investors.”
The title of this post should be a big hint: Everything you need to know in order to win StartupBus North America 2022 is contained within a podcast. This is the third in a series of posts covering the “Startup Bus” series of episodes from Gimlet Media’s Startup podcast, which covered the New York bus’ journey during StartupBus 2017.
…and here are the lessons I took away from this episode:
If you can find teammates that are on your wavelength, you can achieve a lot. Although they’re on the Florida StartupBus and not the bus that the podcast is covering, they remain a source of fascination for Eric, the host. Not only do Robert Blacklidge and Trey Steinhoff get along so well, but they also work so well together, and the synergy will take them far together. (Full disclosure: I worked with Trey at Lilypad, and can vouch for the fact that he is a great teammate. I also know Robert and can understand why he and Trey got along so well.)
A conflict within the team doesn’t have to destroy the team; in fact, not only can conflicts be resolved, but they can even strengthen a team. Ash from the Denari team had rubbed many of his teammates the wrong way, and there was talk of kicking him off the team. Things have turned around in this episode: everyone’s getting along, and Ash is considerably less acerbic — even optimistic-sounding.
The StartupBus format borrows some of its ideas from reality TV game shows, which means that there can be intentional confusion. “The teams have been getting different information about the competition all day. They’re hearing conflicting things about timing, about whether or not pitch decks are allowed. And this confusion, it all feels weirdly intentional.”
StartupBus is supposed to be a challenge. It’s not supposed to be easy, and as anyone who’s done it before will tell you, it can be gruelling at times. And that’s a good thing — if StartupBus works as designed, you shouldn’t be exactly the same person at the end of the ride. As one of the Denari people puts it: “This is a Navy SEAL training program for startups. This is like we’re going to push you to that to the limit of your mental strength, like every single person on their team is that like living in a role that’s very different from what they walked on the bus wanting to do.”
Speaking about come out of StartupBus a little different, you can see some of the buspreneurs’ change — they’re more certain, more directed, more convinced of their ability to change their personal course through life.
You can most definitely incorporate singing and music in your pitch. The pitch for singing telegram startup Yeti featured one of their buspreneurs in a full Marilyn Monroe costume, singing Katy Perry’s Firework, but with StartupBus-specific lyrics. I also did that with the accordion at StartupBus 2019.
You can also use audience participation in your pitch. Tampa-based CourseAlign did that by asking the audience for a show of hands, using questions that would get a specific kind of result.
Be ready for tough questions. During the Q&A section of their pitch, Denari — the Blockchain-powered GoFundMe-like startup — is asked how they plan to prevent their system from being turned into a money-laundering platform.
Don’t be too hard on yourself. After getting that tough money-laundering question, Colleen Wong, who’s been leading Denari, felt bad about her answer and said that she didn’t feel that she was a good leader. Eric the host had to reminder her that she did the near-impossible — “Are you kidding me?! Have you, like, seen yourself this week?! …You, like, pulled together the, like, craziest team on the bus. It was a great thing.”
Anything can happen in the judging room. Eric the host was invited into the judging room to record a reenactment of judges’ discussion as they tried to decide who would move the next round. But as they reenacted their discussion, they started changing their minds. The judging process can turn on a dime.
There is a downside to making it into the finals: It means that although you’re in a party town, you can’t party. You’re going to be working on your product and your pitch for the finals. Trust me on this one — I was in New Orleans, one of the best party towns in the country, and I spent Saturday night with my team working on our startup.
The title of this post should be a big hint: Everything you need to know in order to win StartupBus North America 2022 is contained within a podcast. This is the third in a series of posts covering the “Startup Bus” series of episodes from Gimlet Media’s Startup podcast, which covered the New York bus’ journey during StartupBus 2017.
…and here are the lessons I took away from this episode:
If you run into a difficult person in the morning, you ran into a difficult person. If you run into difficult people all day, you’re the difficult person. I don’t want to reduce Ash, one of the buspreneurs, to a single quality — difficult person — but his “hey, I’m just being real” approach to everyone and everything is one of the hallmarks of difficult person-ry. One of the challenges of being a difficult person is that people will work with you only if you provide value that outweighs your difficulty, and that’s not easy to accomplish. This episode gives us a deeper look at Ash. While he can be a difficult person, we get a better understanding of who he is. Which leads me to me to my next observation:
“The thing about StartupBus is that it really is like a reality TV show. It’s so intense that every interaction, every personality can feel like a caricature of real life.”In the previous episode, Eric the narrator observed that StartupBus feels a lot like one of those “reality TV” competition shows. In this episode, he takes the observation one step further by noting that in a high-pressure setup like StartupBus, it’s all too easy to reduce your busmates to the most obvious aspect of their personality. Remember that people are more than what you see on the surface.
Even though the company you’re creating on the bus isn’t “real,” it helps to get real users, and you either get them through your social network or through advertising. It’s more impressive to the judges at the finals when you can say “Even at this early stage, we already have x users for our product.” You may be working under a compressed timeline, but it’s still doable, and not only do users give you cred with the judges; users can also give you valuable feedback.
Pay attention to the details when you’re spending money. One of the teams paid for Facebook ads, but clicking on the ads took users to https://phishly.io when their site actually lived at plain old http://phishly.io. That was 65 dollars down the drain.
StartupBus may be the “wild card” that you need in your life. As Madelena Mak, one of the conductors on the bus says: “I think like lot of people who join the bus have that same feeling I felt, like that they want to be dealt a wildcard. That they want to be pushed to the limits so they can break out of their own old molds. Like they want to be something more than who they think they can be. It’s not about the bus. It’s about learning something about yourself.”
The pitching gets tougher. As the bus approaches the destination city — New Orleans in the case of StartupBus 2017, Austin in this year’s case — you’ll be pitching in front of judges who’ll ask questions that will require you to have thought through more angles. For example:
Team Daisy — the folks behind the funeral-planning app — were asked if they’d considered handling issues beyond just the funeral, such as death certificates.
Team Denari — the team with the app for sending cryptocurrency to people in need — got stuck on a question that exposed their blockchain-induced blindness. When they said that they could outdo GoFundMe because it services only 19 countries, one of the judges countered with “You are talking about now securities exchange over multiple countries. Maybe there are reasons GoFundMe only deals with 19. Which I haven’t heard you guys say. Is it cause they don’t want to? Because that’s kind of what it comes off as. It’s like, ‘GoFundMe is the largest one, they’re only in 19 countries.’ Why is that?”
As the title of this post puts it: Everything you need to know in order to win StartupBus North America 2022 is contained within a podcast. This is the second in a series of posts covering the “Startup Bus” series of episodes from Gimlet Media’s Startup podcast, which covered the New York bus’ journey during StartupBus 2017.
Eric the narrator discovers the secret of StartupBus: it’s like a reality TV show, but in real life! “When I was growing up, my family was very into a particular kind of reality tv—competition shows… 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.”
The lesson you should take from Eric’s realization: if you think you wasted your time watching Survivor, The Amazing Race, or similar shows, guess what…you didn’t! A lot of the personal dynamics on those shows is pretty much like those on StartupBus.
Be prepared to pitch constantly. Eric observes: “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.”
Be prepared for surprise challenges and surprise obstacles. StartupBus borrows a big trick from reality TV shows: surprise obstacles. When the bus pulls into Charlotte, North Carolina, the New York team finds out that they’ll be pitching against two other teams — a bus that started in Akron, Ohio and another that started in…Tampa!
Don’t limit yourself to just software, because there’s a chance that some team on another bus isn’t limiting itself to just software. “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.’”
Try not to fall into the trap of traditional gender dynamics. On one team, there’s a good news/bad news thing going on because they’re electing one of the women to be CEO; the bad news is that it’s a job that none of them particularly want, and a lot of it will be about reining in unruly behavior.
Have a plan for managing conflict. On another team, a “that’s just who I am” kind of guy butts head against a woman on his team. This is a pretty big topic, and I’ll write more about it in a later post. Just know that you may have to manage conflict within the team.
