Chris Guillebeau

Side Hustle School

Business EN ↓ 3648 episodes

A daily show for everyone who works a regular job and wants to start an income-earning project on the side. In each episode, listeners will hear a different story of someone who's started a side hustle—along with what went well, how that person overcame challenges, and what happened as a result. The show is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and other books. Hosted on Acast. See acast.com/privacy for more information.

Be sure to visit the podcast's website and support the creator: sidehustleschool.com

Author

Chris Guillebeau

Episodes

#2469 - TBT: Action Figure Fan Sells GI Joe & Transformers 05.10.2023 5:53

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an action figure seller who actively buys and sells hundreds of GI Joe, Transformers, and other classic brands every month. 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...

#2468 - Q&A: “How much time do I need to spend?” 04.10.2023 5:42

In this episode, we help a listener figure out how much time she realistically needs to invest in a side hustle while managing her retail job and family life. 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. Sho...

#2467 - Q&A: “Should I quit my dropship hustle?” 03.10.2023 5:07

When is a side hustle just not viable? In this episode, we look at a few red flags that could indicate it's time to change your business or walk away. 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. Show notes:...

#2466 - First $1,000: Sorority “Personal Brand Advisor” for Rush Week 02.10.2023 6:10

In this week’s First $1,000 segment, we hear from a junior at the University of Alabama who advises potential sorority sisters on how to improve their personal brands. Yes, this is a thing! 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&am...

#2465 - Q&A: “Can I earn money on Twitch without streaming all day?” 01.10.2023 4:40

In this episode, we tackle a question about monetizing a love for gaming and Twitch streaming without making it a full-time gig. Can you get paid for streaming and still have a life? 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 se...

#2464 - Q&A: “What’s the best way to monetize a small news site?” 30.09.2023 4:58

An independent journalist in New Mexico seeks to revitalize the local news, starting with his own independent website—but needs help with monetization. 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. Show note...

#2463 - Failure Friday: Halloween Festival Gets Rained Out 29.09.2023 6:01

In this week’s Failure Friday segment, we hear from a grade-school teacher who moonlights as the host of a fall festival. The big downpour that arrived on the big day turned out to be the least of her problems. 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 les...

#2462 - TBT: Parking Lot Striper Lines Up Repeat Business 28.09.2023 6:48

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a parking lot striper who’s built a seasonal, recurring business keeping parking lines looking spiffy. For less than five hours a week on average, he earns an extra $2,500/month Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job...

#2461 - Q&A: “I’m a Parisian architect building 3D models…” 27.09.2023 5:09

With over a decade of experience, this European architect is planning to venture into the realm of 3D visualization. How can he stack the building blocks in his favor? 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...

#2460 - Q&A: “A course to help parents learn sign language…” 26.09.2023 5:03

A listener wants to teach American Sign Language (ASL) to parents of newborns. How could she create the best possible online course? 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. Show notes: SideHustleSchool...

#2459 - First $1,000: Camping YouTuber Earns Affiliate Income 25.09.2023 5:40

In this week’s First $1,000 segment, we hear from a frequent camper who begins making YouTube videos to show off gear and tips. This turns into a regular income stream as viewers make purchases. 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...

#2458 - Q&A: “Is it better to sell low or high-priced courses?” 24.09.2023 5:29

It’s not a trick question: sometimes a low-priced course is much better than a high-priced one. 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com...

#2457 - Q&A: “Using DNA results to create family history books…” 23.09.2023 5:07

We all know that DNA testing is a big business. This caller wants to use customer-submitted results to create custom family history books. 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. Show notes: SideHustleS...

#2456 - Failure Friday: “We didn’t realize every order was free…” 22.09.2023 6:13

In this week’s Failure Friday segment, we hear from a restaurant owner who activates a DoorDash account to bring in more business. Unfortunately, he ends up giving away $1,500 in orders for free. 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 listene...

#2455 - TBT: Print-on-Demand Seller Earns $30,000 in Passive Income 21.09.2023 6:41

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a print-on-demand seller who uses JungleScout and other tools to find competitive and profitable items. 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 s...

#2454 - Q&A: “Are book tours profitable for authors?” 20.09.2023 5:21

A Nashville novelist is coming to my book tour event—and she wants to know if these tours make any money! Let’s spill the beans. 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. Show notes: SideHustleSchool.com...

#2453 - Q&A: “Will people buy my antique map reproductions?” 19.09.2023 5:14

After finding a “treasure trove of antique maps” left to her by a traveling grandfather, this geographer is thinking of selling the reproductions as part of a subscription. 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...

#2452 - First $1,000: Mocktail Tours Support Sober-Curious Visitors 18.09.2023 5:47

In this week’s First $1,000 segment, we hear from a Washington, DC tour guide who specializes in mocktail-making and sober-curious visits. You don’t need to drink (alcohol) to have a good time! 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...

#2451 - Q&A: “Can I start a GoFundMe for my business??” 17.09.2023 4:55

GoFundMe is used for personal fundraisers of all kinds—but could you use it to raise money for your business idea?? 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. Show notes: SideHustleSchool.com Email: team@s...

#2450 - Q&A: “Can I sell a ‘vintage vinyl’ subscription?” 16.09.2023 5:00

A caller dreams of sending melodies from the past into homes with a monthly subscription box. 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com B...

#2449 - Failure Friday: Chicago Coffee Roaster Grinds to Halt 15.09.2023 5:41

In this week’s Failure Friday segment, we hear from a Chicago coffee roaster who has to cash in his caffeinated side hustle. Was this a pour-over decision? 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. Show...

#2448 - TBT: Turning LinkedIn Connections into Fashion Collections 14.09.2023 5:46

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a freelance clothing designer who hunts down new clients on LinkedIn. Let’s go behind the seams! 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 d...

#2447 - Q&A: “Selling NFL subscriptions at 50% off…” 13.09.2023 5:30

You won’t believe the loophole this caller has found—but is it legal or ethical? 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show:...

#2446 - Q&A: “Why will readers care about my food blog?” 12.09.2023 6:43

If a food blog falls in the forest, does anyone read it? Let’s see if we can help this ambitious baker best position herself for blogging success. 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. Show notes: Sid...

#2445 - First $1,000: New Podcaster Sets Up Joint Venture Deals 11.09.2023 6:20

In this week’s First $1,000 segment, we hear from a new podcaster with a business model of setting up joint venture (JV) deals. How does it work and how much money does he make? (Hint: at least $1,000.) 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...