Startup Spotlight: Upstart – Entrepreneurship meets Dungeons & Dragons

Editor’s Note: This summer, Richard Dacalos – educator, coach, and founder of a startup board game called Upstart, visited the McGill X-1 Accelerator and played a game with us. I was curious about his journey, as well as his thoughts on learning with games, so I decided to just interview him and share the insights with our readers. Upstart, which has been featured on Huffington Post, does a great job at teaching entrepreneurial skills, but more importantly, it’s a lot of fun!

On the value of a risk-free, startup life simulation

Richard Dacalos – founder of Upstart

1. Experimentation and making mistakes to learn is encouraged: you can play at business the way your real-life self would, or experiment and do things differently to see if there’s any value there. The game is designed to reveal some of your habits and mindsets around entrepreneurship. Unless you’re really intentional about it, you’ll probably stick to your regular habits.

There was one guy who discovered he was a wantrepreneur. In real life, he would go to a lot of pitch competitions without really developing something tangible. In the game, he was looking for followers without building something. Then he realized he was doing the same thing in real life. A few weeks after noticing this about himself, he came back to me and showed me that he made progress on a simple shirt business. And he believes Upstart was the reason he went that way because it illuminated his real life habits in a gentle way that allowed him to notice it himself, without any real life losses.

We’ve essentially compressed 2-3 years of startup experience in a 2-3 hour game…and the game shows you that life and business are interweaved, not separate.”

2. Also, there’s great value in seeing time and money as resources you hold in your hand. When you realize that those things are limited, you become very intentional about how you spend them – which is how it should be in real-life, although most people don’t necessarily act like it.

3. Finally, it’s a great game to gauge whether or not entrepreneurship is for you. It can serve as testing grounds to see what an entrepreneur’s life is like. We’ve essentially compressed 2-3 years of startup experience in a 2-3 hour game. The choices you make will affect your outcome, and the game shows you that life and business are interweaved, not separate. For example, your health, the quality of your relationships (whether it’s your family or your professional network), and the success of your business, are all dependent on each other.

What is it about games that makes them such a great learning tool?

The research on gamification is out there: it increases engagement unlike anything else. And it’s fun. We’ve had to go through several iterations to engineer the right balance between learning and fun.

The first MVP was too real and serious – economic downturns could destroy your business, there would be nothing you could do about it, and you’d lose hours worth of progress. That would be a realistic simulation, but isn’t that fun.

So we prototype, gather feedback, and then test a new version of the game: Remember, we’re a startup too.

To learn more about Upstart or support their Kickstarter efforts, visit

How Upstart works

It’s like any role-playing game. You get to choose your character, which determines how your attributes start off including your salary, how strong your network is, and how much business influence you have.

Then everyone rolls the dice (which can simulate the luck factor often ignored in entrepreneurship) and the game becomes a matter of doing the best with the cards you’re dealt. You move along the board, like in life. There’s also a game master who will help guide the players and act an as invisible hand to keep the game balance and moving forward.

Just like real-life, you can get sick because you’re neglecting your health and overworking for example, and lose a turn where you can’t work on your business.”

The strategy part is the cornerstone: you can use time and money to make decisions – and you’ve got limited amounts of both. A full-time employee would only have 15 hours to spend towards improving their business each week through a variety of tasks like networking, marketing, or hiring someone. A full-time entrepreneur would have 50, although they would have less capital to work with.

What’s fun is the way that your attributes, like health, come into play. Just like real-life, you can get sick because you’re neglecting your health and overworking for example, and lose a turn where you can’t work on your business.

There’s no one way to win. Instead, there are FOUR ways:

  1. Scale your business – A certain amount of capital that the business needs to attain
  2. Too popular to ignore – 10 000 followers, for example
  3. Cashcow – attaining a certain amount of personal wealth
  4. Stability – building a business that stands the test of time; one that generates a certain amount of capital every turn
Upstart is played in over 20 different countries to help people develop entrepreneurial skills, without any of the real-life risks.

How real-life skills come into play to win

There were some games where people were making deals among themselves on the side, using REAL money, to win the game. This is a great example of people improving their negotiation skills through Upstart.

And there’s actually a tile in the game where if you land on it, you have to do an elevator pitch for your in-game company, and the other players vote pass or fail. In this case, you’re having to demonstrate your speaking skills and your understanding of your business in 30 seconds when your in-game business is on the line.

Schools haven’t changed since the 1800s, and Upstart wants to revolutionize the way people learn.”

On teaching a gamified entrepreneurship course

I had a conversation with the director of a college here, and they needed an entrepreneurship course. I’m always looking for unique ways to teach, so I thought: “Why don’t we teach a course where the whole course is a game?”

Schools haven’t changed since the 1800s, and Upstart wants to revolutionize the way people learn. And we’ve managed to do it in a field that is ripe. We talk about innovation and disruptive all the time, but the very way it’s taught is lagging.


Some of the formative experiences that helped Richard develop Upstart

I played great games like Kiyosaki’s Cashflow which taught me a lot, but didn’t simulate entrepreneurship well. Along the same time, I tried and failed launching a number of businesses. I also played role-playing games like Dungeons & Dragons, as well as video-game RPGs. Certain games like the Game of Thrones card game are really well polished and gave me some models to emulate.

But one of the biggest experiences that helped me create Upstart was my time as a curriculum developer. That’s what really got me thinking in the mindset of: “What are the learning outcomes I want people to get?”

All of those experiences then came together when I created Upstart – a role-playing entrepreneurship game that teaches people real skill sets, and useful mental models.

Upstart is a Startup itself

When I began working on Upstart, I treated it like any other business. I started by immersing myself into the market: going to board game events, playing every game I could get my hands on, and hitting the streets to ask real people questions.

Then I made the MVP in a WEEK for my team to play with, and test it in over 20 different countries. It was raw, it was ugly, and people still played it. And that’s when we knew we were onto something. 2 or 3 iterations later, we started our first round of crowdfunding.

To make sure quality was good, I went through and inspected by hand, every copy of the game myself. (Editor’s note: This is a great example of how doing things that don’t scale can help jumpstart your business in the early stages)

How Upstart is different from its competitors

This is really a game to TEACH entrepreneurship – it’s not just a distraction. In fact, we offer a total package for schools (from over 20 different countries) if they license it. The game can serve as a processing tool in an incubator to help think about real life business. When you play with others, you’re evaluating their moves.

I remember this example where a player was playing as a full-time employee and working on something on the side, which was also her real-life situation. Then she saw everyone else playing and noticed how fast they were moving. Their businesses were moving at 2-3X the pace of hers, simply because she was only part-time. A few weeks later, she quit her real-life job and went full-time to grow her business. That’s the kind of impact Upstart can have.

To learn more about Upstart or support their Kickstarter efforts, visit


Mo Akif

Mo Akif

The Editor-in-Chief of the McGill Dobson Chronicles. Never having started a lemonade stand as a child and tired of reading blog posts about entrepreneurship without actually doing anything, he was on the verge of giving up and joining a pyramid scheme. Luckily the McGill Dobson Centre decided to adopt him, allowing him to get a closer look at what it takes to build something valuable.