Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau / Onward Projectsidehustleschool.com

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.

Sales and Distribution by Lemonada Media https://lemonadamedia.com/  

Episodes

#1914 - Las Vegas Wedding Officiant Bets on Red

A car rental consultant goes from Hertz to hearts with a six-figure side hustle. 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: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193count...

Mar 29, 20226 minEp. 1914

#1913 - First $1,000: “I wanted to keep well-trained wellness providers in business…”

In this week’s First $1,000 segment, we hear from Brooke Thomas, a longtime wellness practitioner who sets out to start a “healing arts incubator.” 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: SideHustleSchool.com/questions C...

Mar 28, 20228 minEp. 1913

#1912 - Q&A: How to sell services to people caring for older parents?

Today’s caller is interested in selling services to people caring for elderly parents. What kind of offers might he be able to develop? 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: SideHustleSchool.com/questions Connect on Tw...

Mar 27, 20225 minEp. 1912

#1911 - Q&A: How to enter the play-to-earn gaming space?

Last month on my blog, I published a 4,000 word post about DeFi Kingdoms, a blockchain game and decentralized exchange that I’ve been participating in. I got a ton of messages about it, including this one from a listener who wants to jump in. 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: SideHus...

Mar 26, 20225 minEp. 1911

#1910 - Failure Friday: “My first customer bought out of pity…”

In this week’s Failure Friday segment, we hear from a Tasmanian seller of reusable cutlery. Business is going well now, but her early experiences at the local farmers market were discouraging. 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 ...

Mar 25, 20226 minEp. 1910

#1909 - TBT: “Pizza City USA” Becomes Book, Podcast, and Festival

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Pizza City USA, which offers walking tours (and an upcoming festival!) from its home base in Chicago. 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...

Mar 24, 20228 minEp. 1909

#1908 - Q&A: Should I let my customers choose their own price?

This listener is thinking of letting her customers set their own prices. Is the pay-what-you-will pricing model revolutionary or risky? 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: SideHustleSchool.com/questions Connect on Tw...

Mar 23, 20225 minEp. 1908

#1907 - Marine Resells Appliances for Extra $2,000/Month

A former Marine living in pricey California sets out to earn an extra $2,000/month by buying, fixing, and flipping washers and dryers. 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: SideHustleSchool.com/questions Connect on Twi...

Mar 22, 20227 minEp. 1907

#1906 - First $1,000: “I still remember the day I hit the goal…”

In this week’s First $1,000 segment, we hear from Jodi Carlson, who sells resources and materials for Girl Scout troop leaders. 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: SideHustleSchool.com/questions Connect on Twitter: @...

Mar 21, 20229 minEp. 1906

#1905 - Q&A: Website that offers Black Friday deals all year long?

Today’s caller is thinking of promoting Black Friday sales (and other big sales) all year long. What would this business model look like? 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: SideHustleSchool.com/questions Connect on ...

Mar 20, 20225 minEp. 1905

#1904 - Q&A: Is it legal to sell a guide about magic mushrooms?

A listener wants to write a guide to Psilocybin, the mushroom-based drug that’s now legal in some states, but not most. Will they get in trouble for showing how to consume this wonder drug? 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 ...

Mar 19, 20225 minEp. 1904

#1903 - Failure Friday: “The reality was not as awesome as the dream…”

In this week’s Failure Friday segment, we hear from a couple who operates a vintage camper rental business. In their early days, they learned a valuable lesson about paying attention to details and systems. 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@sidehustle...

Mar 18, 20229 minEp. 1903

#1902 - TBT: British Vintage Store Owner Supplies Clothes for Netflix

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a vintage store owner in Birmingham, England. She’s chuffed about her business! 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: SideHustleSchool.com...

Mar 17, 20227 minEp. 1902

#1901 - Q&A: When should I go full-time?

A caller from Hawaii is wondering if it’s a good time to transition from his second part-time job into his primary side hustle. What are the most important factors to consider in making this 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 notes: SideHustleSchool.com Email: team@sidehustleschool...

Mar 16, 20225 minEp. 1901

#1900 - “Geek Chic” Skincare Blogger's Persona Pays Off

A fashion and skincare blogger promotes a culture of trust using the scientific method to craft clever content online. 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: SideHustleSchool.com/questions Connect on Twitter: @chrisguil...

Mar 15, 20226 minEp. 1900

#1899 - First $1,000: “Every day, I dropped off hundreds of orders at the post office…”

In this week’s First $1,000 segment, we hear from the creator of Dental Lace, the original zero-waste dental floss. It’s now sold in retailers worldwide—but it all started with an idea that some people thought was crazy. 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: t...

Mar 14, 20228 minEp. 1899

#1898 - Q&A: Will this “all you can craft" event venue subscription work?

Our caller today is helping out a friend who runs a local event space. Might the business be more successful with a subscription model? 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: SideHustleSchool.com/questions Connect on Tw...

Mar 13, 20226 minEp. 1898

#1897 - Q&A: Should I buy a rental home with friends?

If you want to get into rental properties, does it ever make sense to do it with a group of friends—and if so, how could you avoid the potential pitfalls? 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: SideHustleSchool.com/ques...

Mar 12, 20225 minEp. 1897

#1896 - Failure Friday: “If I want to do good work, I can’t sacrifice my wellbeing…”

In this week’s Failure Friday segment, we hear from the creator of a card game that sparks meaningful conversations. As sales increased along with her busy day job, she struggled to take time for herself. 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@sidehustlesc...

Mar 11, 20228 minEp. 1896

#1895 - TBT: Outdoor Hockey Brand Scores Three Assists!

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Third Assist, an ecommerce brand focusing on outdoor hockey. 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: SideHustleSchool.com/que...

Mar 10, 20227 minEp. 1895

#1894 - Q&A: Should we turn down Shark Tank?

Two business partners have the chance to go on Shark Tank—but they’re also having second thoughts. Should they refuse Mark Cuban’s 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on...

Mar 09, 20225 minEp. 1894

#1893 - Climber Uses Life Skills to Scale Up Life

Seeking to turn his passion for climbing Ireland’s remote sea stacks into stacks of cash, a ship’s engineer becomes an adventure guide. 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: SideHustleSchool.com/questions Connect on Tw...

Mar 08, 20227 minEp. 1893

#1892 - First $1,000: “I sold my day job skills to a client after-hours…”

In this week’s First $1,000 segment, we hear from Joel Runyon (!), longtime friend and founder of ImpossibleHQ.com. Joel has started numerous businesses in the past decade, but he got his start by taking on a freelance contract using the same skills he’d learned for his day job. 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 severa...

Mar 07, 20227 minEp. 1892

#1891 - Q&A: Can I market myself as a festival concierge?

Today’s caller is an avid concert and festival-goer. Now that big events are back in full swing (at least in some places), is there a way she can get paid to help VIPs have a great experience? 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 ...

Mar 06, 20226 minEp. 1891

#1890 - Q&A: Is it unprofessional to use Venmo for business payments?

Today’s caller uses the mobile payment service Venmo for both personal and work use—but as they’re expanding into a new business, they’re worried it’s not considered professional enough. Do they need a merchant account? 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: te...

Mar 05, 20224 minEp. 1890

#1889 - Failure Friday: “Something miraculous happened: I started making money…”

In this week’s Failure Friday segment, we hear from the founder of Birthday Buddy, an app that sends automated birthday wishes to Facebook contacts. His free service ran into problems, but he regrouped to improve the app AND turn it into a moneymaker. 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...

Mar 04, 20229 minEp. 1889

#1888 - TBT: Quirky Video Animator Finds Online Fame

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Peter Quinn, creator of amazing Instagram videos made with Adobe After Effects. He recently worked on a video with Snoop Dogg! 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@sidehustle...

Mar 03, 20227 minEp. 1888

#1887 - Q&A: “I’ve got a guide with Black Hat tips for sale…”

Today’s caller dares me to feature his question—and I accept the challenge! But should he really start a business selling Netflix logins?? 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: SideHustleSchool.com/questions Connect on...

Mar 02, 20225 minEp. 1887

#1886 - “Overlanding” Blog Offers Long-Range Travel Tips

A Romanian living in London profits from sharing his experience with extended road trips. His blog brings in more than $2,000/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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitt...

Mar 01, 20228 minEp. 1886

#1885 - First $1,000: “It felt like proof that we were doing something right…”

In this week’s First $1,000 segment, we hear from Sabrina and Garrett Ricci, the co-founders of a modern podcast focused on prehistoric times. We love I Know Dino! Check out their dino-mite update. 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.co...

Feb 28, 20228 minEp. 1885