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Startup Bus: Bootcamp for Tech Entrepreneurs

By In Technology

Adapted from my 2018 Ignite Talk

For most people in the tech world, life can be fairly drab They sit in cubicles, at insurance companies, writing code, designing their millionth, mind numbing button, or making cold calls to hostile schmucks all day. It’s a job right? Something you have to be paid to do, because no one in their right mind would do this for free.

On the other hand, we have the guys in Silicone Valley, wrapped in hoodies and self righteousness, planning on getting rich and changing the world (not necessarily in that order). But how do you get from cubicle to your dream? Working on what you love?

“I’m never doing this again”

I would like to tell you about one the best dumb ideas of recent history: The StartupBus. A Navy Seal boot-camp training program for tech entrepreneurs. Or so I like to think.

In 2010, my friend Elias, was working in Venture Capital, and wanted to get a bus with a bunch of friends and go to South by South West – the huge film, music and tech conference in Austin. He thought would be funny to semi-mock Startup Culture in Silicon Valley by having everyone on the bus try and build a tech startup in the three days it would take to get there from San Francisco.

It sounded crazy to everyone, but they all had so much fun, that a group of them decided to turn it into a “my-city-is-better-than-your-city” tournament the following year. They all went back to their respective states, and started recruiting riders for a full-blown competition. 

The format is simple: 30 strangers get selected to get on a bus, as long as they are extremely competent and fall into one of three clichéd categories: Hipsters Hackers, and Hustlers: Graphic designers, Computer programmers, and Marketing and Business Development people.

They then get on the bus day one, introduce themselves, and pitch an idea for a startup. Groups then form around the ideas, and then the teams work like crazy, for three or four days, to make an actual business. With REAL products, and even Customers – In three days!

I was first invited to ride the 2011 Miami bus. I worked on two separate teams, competed against 10 other busses, 60 other teams,  and didn’t sleep for four days, and met some of the most amazing people that are still in my life to this day.

Since then, the competition has grown. There are more and more busses every year from more cities, a separate European competition, and I’ve recently gotten back from the inaugural StartupBus Africa trip, which was epic! But why would anyone do this?

Well, most people are just… terrible at their jobs. I assume you’ve found this yourself. But the bus is different. The sheer caliber of the people you meet if off the charts. Everyone works so hard, and is so good at what they do, that there is a feedback loop of inspiration; You WANT to work harder to show that you belong. 

The result is productivity to an extent not seen in the real world. What can you create on a bus in three days? How about a fully fledged, artificial intelligence food ordering system that will automatically order you lunch every day? Yeah, we did that. 

Nomscription – Built in three days. On a bus.

Internet free chat system for disaster areas? Yup. A career matching system for Veterans? Check. Customized cereal delivered to your door? Yup. A full social network for selling what you grow in your back garden – a team from Tampa built that!

And there are hundreds of others. But the bus isn’t all flowers and roses. In fact it is totally awful. And that is one of the reasons it’s so successful. If you can build something amazing in three days next to a chemical toilet, you can do anything.

There is bad food, motion sickness, team melt downs, spotty power and internet access, and every new hell you’d find in a real startup, but compressed into the equivalent of a long weekend.  As a result, you learn to be flexible, to deal with the chaos, and to thrive.

Then there is the physical side.  Try having a normal conversation after writing code for ten hours doing this. Also, after four days without sleep, you can have some pretty inspiring insights, as well as some mind-blowing hallucinations. Not to mention all the caffeine and alcohol.

The pure squalor of the situation, combined with the amazing team work that goes on, binds you so closely to those people, that you instantly have 30 new best friends. I started referring to the processes as entrepreneurial Stockholm Syndrome. 

But the process opens your eyes. A passionate, five person team, working 16 hour days, for four days straight, produce 320 hours of actual work. That’s an equivalent 40 work days of super productivity. 

If you can build a complete product, create marketing materials, pitch decks, business cards, have customers and sales, etc., all in three days, ON A BUS, what could you do if you gave yourself six months?

I bet that you’re pretty amazing. You just can’t begin to realize how freaking amazing you REALLY ARE until you’ve HAD be amazing waste deep in crap and sleep depravation. There are no excuses. Go and build something, right now!

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I help companies turn their technical ideas into reality. CEO @Sourcetoad and @OnDeck. Author of Herding Cats and Coders. Fan of squash, whiskey, aggressive inline, and temperamental British sports cars.

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Don’t Fall Into the Trap: Why Startup Software Development Isn’t Like Corporate Development

In Startups, Technology

So, you’ve left the corporate world, and now it’s time to build your own startup. You’ve probably managed dev teams before, overseen product launches, maybe even helmed some fancy project management tools that made everything run like a well-oiled machine. You’ve done this before, right? Not exactly. When it’s your startup, everything changes—and, as I’ll explain, if you assume it’ll work the same way, you’re heading for a few surprises.

Startup founders often fall into a dangerous trap when starting a software project from scratch: thinking it’ll be just like building software inside an established company. Here’s why it’s not—and some advice on how to navigate the differences.

1. Switching from Product Manager to Teacher

In an established company, a software team already has two things that give them a serious edge: an existing market and a deep understanding of the business. They’re working within a proven model. Developers in that environment know what questions to ask, can fill in gaps intuitively, and likely understand why they’re building what they’re building.

At a startup, however, your devs are going to need a whole lot more context. They’re not working with familiar requirements—they’re working with your vision, which may be abstract at this stage. If your development team doesn’t understand why something matters, it’s a recipe for ambiguity and frustration on both sides.

Advice: Think of yourself less as a product manager and more as a teacher. Your job is to make sure they understand the core problems, not just the features. Teach them why each requirement matters, help them visualize the end-user, and create that shared language for decision-making. It might feel tedious, but it’s essential to avoid future misalignment and expensive rewrites.

2. Beware of Perfectionism — It’s the Budget Killer

In a large company, products with an existing user base often have to be polished. Features need to be rock-solid, invoices have to be perfect, and everything needs an audit trail. Startups, however, have a different goal: get an MVP in the hands of users fast. It’s a classic trap for first-time founders—focusing on “perfection” and “polish” before knowing if the business model even works.

Startup perfectionism is budget poison. It’s shocking how quickly adding “nice-to-have” features can chew through funding, especially if you’re paying a dev team to build things like automated invoicing or churn management before you’ve even proven people want what you’re selling.

Advice: Ruthlessly strip down your MVP. If a feature doesn’t help you validate your market, it goes on the “later” list. Keep the scope laser-focused on what helps you test your business assumptions. Let the non-essential features wait until you know you have customers who’ll use them.

3. Zen and the Art of the Startup Pivot

Building software for a startup means embracing one cold, hard truth: the business model will change. According to research, 93% of successful startups pivot at least once (and often more). Imagine being asked to go out and passionately sell something that you know might not look the same next year—or next month. It takes a level of zen acceptance that your original idea will likely morph, but that’s what keeps you flexible and ready to capture new opportunities.

For founders, that requires a mindset shift. You have to believe in your product, while also knowing you might be building the “wrong thing” in some way. The focus should be on preserving capital and brainpower for what’s next. The game is less about proving you’re right and more about staying adaptable.

Advice: Budget with pivots in mind. Set your burn rate assuming you’ll need to make big changes. Don’t let ego get in the way of listening to the market, and keep enough gas in the tank for at least one big strategic turn.

4. The Hard Work of Being Your Own “Internal Customer”

Here’s another big one. In a corporate environment, you have internal customers—departments or stakeholders with specific goals that align with the overall company mission. For a startup, the only customer you have is you. You don’t have a preexisting feedback loop from various departments, and you don’t have established success metrics. You have to create that from scratch.

Advice: Start by building an internal customer profile based on your target market, then use that to set clear goals and success criteria for your dev team. If you’re focused on, say, usability for early adopters, set KPIs around usability testing and build from there. By acting as your own “internal customer,” you’re setting a clear direction and saving your team from working in a vacuum.

5. Get Ready to Build AND Sell

Corporate software development often has the luxury of a separate, dedicated sales team to deliver the product to the right audience. As a startup founder, you’re both the builder and the seller. That means you’re not just iterating on software—you’re iterating on messaging, product-market fit, pricing, and maybe even distribution models.

Advice: Factor in time for sales-ready iteration in your dev cycle. As you build, keep track of how each release or update affects the user experience. Ask yourself if the changes make your pitch clearer or simpler and how they align with the current market’s needs. Ultimately, this approach will help you bridge the gap between building the product and ensuring it’s market-ready.

Conclusion

Building software as a startup founder requires a whole different toolkit than you may be used to. You’re part-teacher, part-salesperson, part-zen master, and always the chief budget officer. By recognizing the unique mindset shifts and traps of startup software development, you’re positioning yourself—and your team—for the best chance of success. Focus on creating clarity for your team, set ruthless priorities, embrace change, and never lose sight of the fact that the first version is just the beginning. In the startup world, adaptability isn’t just a skill—it’s the entire game.