4.8 • 3.3K Ratings
🗓️ 9 January 2026
⏱️ 7 minutes
🧾️ Download transcript
In this week’s Failure Friday segment, we hear from a mobile game developer with an ambitious idea—so ambitious that it never got off the ground.
Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.
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| 0:00.0 | It's going to be a big year. And January is when so many of us set goals for our business, |
| 0:04.8 | for all the things we want to achieve. And in a small business or a side hustle, even, |
| 0:09.6 | cash flow can make or break you. So if your money gets tied up, if your tools don't connect, |
| 0:14.1 | every decision feels unnecessarily stressful. Maybe it's time to switch to Intuit QuickBooks's |
| 0:20.0 | money management tools. Big shout out to QuickBooks, |
| 0:22.9 | our sponsor, start the year with confidence about your goals. Learn more at quickbooks.com |
| 0:27.9 | slash money today. Again, that's quickbooks.com slash money. Terms apply. Money movement services |
| 0:34.7 | are provided by Intuit Payments Incorporated, licensed as a money transmitter |
| 0:38.2 | by the New York State Department of Financial Services. |
| 0:43.6 | Lemonada. |
| 0:48.1 | Hey friends, what's up? Welcome back to Side Ussel School. It's Chris Gillibault, your host here. I'm excited to return to a segment. We ran for a couple years. We didn't run it at all last year, but we got a lot of questions about it. It was really popular. It was kind of polarizing in a way because the segment is all about failure. And when I started it, some people were like, why are you running failure stories? Like, isn't this about side hustle successes? But if you ever listen to the episodes, you would know it's often about what we learn through something that doesn't go well. And the side hustler or small business owners sharing the story often had built a pretty good business, but just something went wrong along the way. |
| 1:28.1 | And so we can learn a lot of lessons from that. So I always loved working on this segment. |
| 1:32.2 | So we're going to return to some of our greatest hits from Failure Friday. And in these stories, |
| 1:37.2 | they vary, but they often begin with an idea, what somebody thought would happen, and then what |
| 1:41.8 | really happened, and of course, what they learned. |
| 1:44.5 | So sometimes there's a disaster, sometimes it's a mistake or a misstep, all kinds of |
| 1:49.2 | variants. I'm going to bring you a bunch of these throughout the year, most likely to a month or so |
| 1:52.8 | as we go along. But without further ado, today's short story features Matt from Western |
| 1:57.7 | Massachusetts. He's going to tell us about an ambitious idea he had for an indie mobile game. |
| 2:03.4 | Now, because this is Failure Friday, you might suspect it doesn't turn out that well. |
| 2:07.9 | And you'd be right. |
| 2:09.3 | But of course, the magic, or at least the lesson, lies in the details. |
... |
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