Chris Guillebeau

Side Hustle School

Business EN ↓ 3536 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.

Author

Chris Guillebeau

Episodes

#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...

#2444 - Q&A: “Can I get paid $250k as an AI prompt engineer??” 10.09.2023 5:46

You might have heard about the rise of AI “prompt engineers,” where people are earning high salaries to help Chat-GPT and other tools create code and content. How do you break into the field? 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&...

#2443 - Q&A: “Should I upload my podcast to YouTube?” 09.09.2023 4:50

A history-loving listener is starting a podcast. Should he also upload it to YouTube to find a wider audience? 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@sidehu...

#2442 - Failure Friday: Graveyard Yoga Fails to Entice Living or Dead 08.09.2023 6:02

Why not blend a love of the macabre with a passion for yoga? Answer: because it’s too spooky to be salesworthy. In this week’s Failure Friday segment, we hear from a yoga instructor who tries to start a “Graveyard Yoga” series. 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...

#2441 - TBT: Part-Time Wordpress Setup Earns Full-Time Income 07.09.2023 6:30

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a business coach in Minneapolis who helps female entrepreneurs optimize their websites. This business operates seasonally and earns up to $6,000/month when it’s in motion. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This...

#2440 - Q&A: “The viability of a 3D printing business…” 06.09.2023 5:19

An engineer hopes to profit from 3D printing. What’s his target market and unique selling proposition? 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@sidehustlesch...

#2439 - Q&A: “My goal is to translate medical documents…” 05.09.2023 4:01

A caller from Spain works for an agency as a professional translator. How can she break out and get translation gigs on her own? 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...

#2438 - First $1,000: Fashion Affiliate Earns $10,000/Month 04.09.2023 6:22

In this week’s First $1,000 segment, we hear from a fashion lover who uses affiliate campaigns to earn commissions. This new business is taking off! 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: S...

#2437 - Q&A: “Going from corporate design to side hustle design…” 03.09.2023 5:24

In this episode, we hear from a graphic designer and marketing pro with a knack for creating branded merchandise from his corporate position—and now he wants to try his hand at getting his own clients. 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 l...

#2436 - Q&A: “Do you think social ads are worth it?" 02.09.2023 5:54

Instagram keeps telling this creator to “boost” her posts by paying for advertising. Is this the path to viral fame or a waste of money? 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: SideHustleSc...

#2435 - Failure Friday: The Destination Yoga Retreat That Wasn’t 01.09.2023 6:56

In this week’s Failure Friday segment, we hear from a yoga teacher who dreamed of leading a retreat in Central America. Just one problem: no one signed up. 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...

#2434 - TBT: SAAS Sales Audits Earn $5,000/Month Part-Time 31.08.2023 5:18

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an Australian who turned to LinkedIn and started pitching companies on a specific service: auditing their sales and marketing processes. This is going really well, earning over $5,000/month part-time. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money wit...

#2433 - Q&A: “Negotiating a raise using Side Hustle School principles…” 30.08.2023 4:58

If you’re side hustling while working your day job, can you still ask for a raise? (Answer: yes!) This episode features four tips to get paid more from your employer. 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 w...