1969 8:56 First $1K

First $1,000: “I couldn’t believe I got paid playing a game I loved…”

In this week’s First title: "First $1,000: “I couldn’t believe I got paid playing a game I loved…”",000 segment, we hear from the founder of StartPlaying.Games, a hub for professional dungeon masters who facilitate tabletop games at private events.

8:56

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What It's About

A dungeon master levels up and creates an online gaming marketplace.

Notes from Chris

Episode 1969
Today’s episode is part of a new feature we’re doing in 2022 called ‘Your First $1,000.’ As you might surmise from the title, this is all about how someone made their first $1,000.

How did they get to that point? Not their first $100,000—that’s cool, but it would probably be a long story.

One thing I’ve learned is that once you begin to earn real money, the steps required to go to the next level—whether it’s $1,000 to $2,000, or even to $5,000 or $10,000 are often easier than that first real paycheck.

With that in mind, today’s feature comes from Devon Chulick in San Francisco. We first featured him back on Episode #1690: Product Manager Starts “Airbnb for Dungeons and Dragons.”

The business grew to become a hub for contracted dungeon masters who produce tournaments for corporate events and other occasions. But when he started, it was just Devon and an idea!

Listen to today's episode to learn more...

 

 

MENTIONED IN THIS EPISODE:
  • Thanks to Devon for telling us about their first $1,000. I hope you found it encouraging. Check out, StartPlaying.Games —maybe even hire your own dungeon master.
SEE ALSO: Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter
Read the full transcript

This transcript was generated from the episode audio and may contain minor errors.

[Music]

Hey there and welcome. My name is Chris Guillebeau. You're listening to Side Hustle School. And this episode is part of a feature we've been doing all year, every Monday, called Your First Thousand Dollars. As you might guess, or as you might know if you've been listening for a while, it's all about how someone made their first thousand dollars.

It's been awesome to work on this series. I have enjoyed the stories. I've got lots of great feedback from listeners. Just hearing this origin of, how do you go from idea to income? Not your first hundred thousand dollars, not your first million dollars, but your first thousand dollars.

Like what are your first real steps to earn real money? So as I said, I've been learning along the way as well. With that in mind, today's feature comes from Devon Chulick in San Francisco. We first featured Devon back on episode 1690. So I guess what, more than 300 days ago or so, his episode was titled Product Manager Starts Airbnb for Dungeons and Dragons.

Pretty cool project. He essentially is working in the world of events, going to gatherings and producing tournaments and Dungeons and Dragons or other role-playing game experiences. And this business actually grew to become a hub for contracted dungeon masters everywhere who produced tournaments for these events and other occasions. But when he started, it was just Devon and an idea. So let's hear about his first thousand dollars.

I think you'll tell us actually about his first $500 times two. So Devon, it's got the story. I'll have a very quick wrap up at the end. [Music]

My name is Devon Chulick. I'm the founder of Start Playing Dot Games and I was featured on Side Hustle School episode 1690.

Here's my first thousand dollars. I had been playing Dungeons and Dragons off and on since I was young. I love the hobby. There's something awesome about playing this game and introducing it to people who have never played before. When I was working full-time as a product manager at Shubby's Shorts, I started running the game for a handful of folks in the office.

I remember someone saying, I bet companies would pay for this as like a team building exercise, one of the nights that we were staying late and playing. And that got me thinking, I wonder if people would pay me to run a game of Dungeons and Dragons for them. It was no stranger to side hustles and moonlighting. So that weekend, I decided to spin up a website, advertising myself as a professional dungeon master in San Francisco. Less than two weeks after putting up the site, I noticed that I was already on the first page of Google and had my first client wanted me to run a game for her and her coworkers.

It was some IT company in Santa Rosa, I think. I remember having drove down after work one day on a Friday, I had all my supplies, my miniatures, my books, everything in milk crates in the trunk of my partner's car. I started to feel very nervous when I was seeing this corporate team in their conference room waiting for me, eagerly. And I'd run so many games with people previously, but it was always with a friend or a friend of a friend who wanted to learn and maybe get into playing Dungeons and Dragons. This company just found me on Google and didn't even shirk at the fact that I was charging $500 for the evening.

Some people ask me, like, why would I charge so much when I was just starting out as a side hustle? And I decided I really only wanted to do this if it was gonna be really lucrative. I had a full-time job and I didn't wanna scrape by with just a few extra bucks for moonlighting. So I decided that I was gonna start with a premium right up the gate. And being in the Bay Area, my rates were considered cheap for most other team-building activities.

But that night went off without a hitch. The group had a blast and have continued to hire me almost every year for their annual summit. And I was definitely excited after that. I remember my jaw dropping when the next day I saw that I had another client wanting to book me to run a game for her and her three boys. And then a week later, another Silicon Valley startup hired me to run a game for them.

Within two months, I had already made my first $1,000, playing a game I loved. And I went on to run games for all sorts of people from Facebook, Google, Nintendo, and eventually built a platform to let thousands of other professional dungeon masters start their own side hustles. Again, my name's Devin and this was my first $1,000. [Music]

Awesome, love that story. I love the $500 starting rate as well.

Like Devin said, it just had to be worthwhile. People start different projects for different reasons. And in his case, he was like, it actually has to make a good amount of money. And $500 as a starting rate is not unreasonable for corporate events, especially in a market like San Francisco. He's probably raised his rates since then.

He's also created this hub, as I mentioned, for other dungeon masters, other facilitators to offer their services elsewhere, which is really cool. So check out startplaying.games, startplaying.games. You can also just go to startplayinggames.com. I discovered that by mistake, but they both work. Maybe even hire someone for your next event.

It looks fun. I do events from time to time, so I'm gonna check it out. And if you've got a question or an update for us about your hustle, sidehustleschool.com/questions, our show notes are also at sidehustleschool.com/1969. 1-9-6-9. Thank you so much for listening today.

I hope you enjoyed it. I hope you'll come back tomorrow. Much more is coming up. My name is Chris Guillebeau. This is Side Hustle School.

[Music]

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