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

#1944 - TBT: Upcycled Journals Provide Renewable Income

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of Just My Type, a creative bookbinding business based in Missoula, Montana. 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: SideHustleSch...

Apr 28, 20228 minEp 1944Transcript available on Metacast

#1943 - Q&A: “I’d like to start a Supreme Court fan club…”

This judicial fan club will provide updates, commentary, and memorabilia in the form of a subscription box. How can our listener ensure a fair ruling?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...

Apr 27, 20225 minEp 1943Transcript available on Metacast

#1942 - Ottawa Teacher Finds “Unexpected Journey” After Retirement

A newly retired teacher capitalizes on the unique spots around Canada’s capital city. 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: @193...

Apr 26, 20228 minEp 1942Transcript available on Metacast

#1941 - First $1,000: “My roommate threw a wad of hundred-dollar bills on the table…”

In this week’s First $1,000 segment, we hear from Silver Picker, a college student turned coin reseller who earned $10,000 one summer from coins and metals he finds at estate sales. 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. Side Hustle School features a new episode EVERY DAY, featuring detailed case stu...

Apr 25, 20229 minEp 1941Transcript available on Metacast

#1940 - Q&A: “How can I grow my podcast without social media?”

A high school student has been hosting a podcast and wants to reach more people—but without using social media. What should she try next, and how can we support her? 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: SideHustleScho...

Apr 24, 20226 minEp 1940Transcript available on Metacast

#1939 - Q&A: “Has my apprenticeship gone on for too long?”

The right kind of apprenticeship can work well for both parties. The wrong kind can be, well, terrible. How do you know the difference, and how can you find a graceful exit ramp when it’s time to leave? 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@sidehustlescho...

Apr 23, 20225 minEp 1939Transcript available on Metacast

#1938 - Failure Friday: “My app kept crashing during the big pitch…”

In this week’s Failure Friday segment, we hear from the founder of iGoal.io, a project management tool. An early pitch to a major investor got off to a rough start. 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: SideHustleSchoo...

Apr 22, 20228 minEp 1938Transcript available on Metacast

#1937 - TBT: Mural Painter Follows Signs to New Career

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a land surveyor who changes careers when he discovers an accidental side hustle painting signs and murals. It’s now a full-time, six-figure 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...

Apr 21, 20227 minEp 1937Transcript available on Metacast

#1936 - Q&A: “Can I file a small claims suit against a big business?”

Today’s caller is having a frustrating experience: they aren’t getting paid for work they’ve completed! Can they take their client to small claims court? 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/quest...

Apr 20, 20225 minEp 1936Transcript available on Metacast

#1935 - Orthodontic Marketer Knows the Drill

This marketer puts his money where his mouth is, striking gold by helping orthodontists market their 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/questions Connect on Twitter: @chrisguillebeau C...

Apr 19, 20227 minEp 1935Transcript available on Metacast

#1934 - First $1,000: Running Coach Strides to Finish Line

In this week’s First $1,000 segment, we hear from Jason Fitzgerald, a fitness coach and founder of StrengthRunning.com. Two years after starting his side hustle, Jason went full-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 Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the sh...

Apr 18, 20226 minEp 1934Transcript available on Metacast

#1933 - Q&A: “Earn $10,000 with 1,000 subscribers—how to do it?”

This listener has a resolution: to start a blog and earn $10,000, in addition to getting their first 1,000 subscribers. What’s the best advice for them? 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/questi...

Apr 17, 20225 minEp 1933Transcript available on Metacast

#1932 - Q&A: “Can I get sponsors for a podcast that doesn't exist?”

We’ve talked about how to get sponsors for a podcast—but what if the podcast is new and hasn’t released any episodes yet? 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: @chrisg...

Apr 16, 20225 minEp 1932Transcript available on Metacast

#1931 - Failure Friday: “I walked away at the last minute…”

In this week’s Failure Friday segment, we hear from the founder of Wastewell, a curbside composting pickup service. After landing a major municipal contract, she began to have second thoughts about the business 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...

Apr 15, 20228 minEp 1931Transcript available on Metacast

#1930 - TBT: Custom Stamp Business Doubles Sales During Pandemic

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of a custom stamp business in Austin, Texas. 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...

Apr 14, 20227 minEp 1930Transcript available on Metacast

#1929 - Q&A: “How do I choose a revenue model for my coaching business?”

Most successful coaches have more than one source of income—but if you’re starting out and need to pick only one, which should you pursue? 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...

Apr 13, 20224 minEp 1929Transcript available on Metacast

#1928 - Woodworking Dad Nets $2,000/Month

Going against the grain of boring, plain Jane doors, this side hustler jazzes them up with paint, glass, and custom decals. 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: @chri...

Apr 12, 20227 minEp 1928Transcript available on Metacast

#1927 - First $1,000: “I didn’t think of myself as an expert…”

In this week’s First $1,000 segment, we hear from the founder of a business that sold bamboo baby products on Amazon. She got so many questions about selling on Amazon that she changed her entire business model. (Lesson: pay attention to the questions people ask!) 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 wee...

Apr 11, 20227 minEp 1927Transcript available on Metacast

#1926 - Q&A: “Best platform for handmade crochet items?”

A listener is ready to sell her handmade crochet items, including baby blankets and seasonal decorations. What’s the best platform for her—and does she need to make a website as well? 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 sh...

Apr 10, 20225 minEp 1926Transcript available on Metacast

#1925 - Q&A: “Can you really earn 150% interest through DeFi?”

Decentralized finance, also known as DeFi, offers the chance to earn high levels of interest (often 150% or more) in exchange for depositing funds. It’s not for the faint of heart, but if you like the idea—what’s the first step? 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 ...

Apr 09, 20225 minEp 1925Transcript available on Metacast

#1924 - Failure Friday: “I’ve never talked openly about what I’m working on…”

In this week’s Failure Friday segment, we hear from the founder of Reciple.com, which offers ad-free recipes from small creators. A previous project had flopped, leaving her hesitant to tell anyone about her new venture. 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...

Apr 08, 20227 minEp 1924Transcript available on Metacast

#1923 - TBT: NYC Pet Sitter Saves $200,000

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a prolific pet sitter who leaves a career in medicine to care for pets full-time. During several years of living in New York City, she was able to save more than $200,000 thanks to never paying rent. 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...

Apr 07, 20229 minEp 1923Transcript available on Metacast

#1922 - Q&A: How can I sell my delicious hot chocolate recipe?

Today’s caller wants to sell hot chocolate! Or actually, she wants to sell her popular hot chocolate *recipe* without scaling the business herself. Is this a feasible goal? 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: SideHus...

Apr 06, 20225 minEp 1922Transcript available on Metacast

#1921 - Intelligence Officer Cracks Code with 7-Figure Course

A self-taught web developer and former U.S. intelligence officer teaches 2,500 women how to build WordPress sites. 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: @chrisguillebe...

Apr 05, 20227 minEp 1921Transcript available on Metacast

#1920 - First $1,000: “It doesn’t sound like much, but it meant the world to me…"

In this week’s First $1,000 segment, we hear from the founder of Katie Goes Platinum, a blog for women embracing their natural hair color. In addition to boosting self-confidence, this blog now brings in a full-time income! 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...

Apr 04, 20228 minEp 1920Transcript available on Metacast

#1919 - Q&A: Which is better: direct or indirect income?

A listener has a clear business idea, but isn’t clear about the revenue model. They can get paid through affiliate and advertising revenue (indirect), *or* through selling to consumers themselves (direct). Which might be better? 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 ...

Apr 03, 20226 minEp 1919Transcript available on Metacast

#1918 - Q&A: Is my business idea a pyramid scheme?

It’s not often that someone calls in and says, “Am I running a pyramid scheme?” … but that’s basically what we’ve got here today. 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:...

Apr 02, 20225 minEp 1918Transcript available on Metacast

#1917 - Failure Friday: “They said it was a wonderful opportunity…”

In this week’s Failure Friday segment, we hear from a private chef who sets out to bring the restaurant experience to your home. Along the way, he learns a valuable lesson: giving out free food to Instagram influencers doesn’t lead to new 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: S...

Apr 01, 20228 minEp 1917Transcript available on Metacast

#1916 - ​​TBT: “Auction Sisters” Raise Millions for Charities

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from one-half of the Auctionisters, two sisters who work as professional auctioneers to help charities raise money. They’ve been in high demand! Going once, going twice… 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: SideH...

Mar 31, 20228 minEp 1916Transcript available on Metacast

#1915 - Q&A: Should I pursue three ideas or just one?

Today’s caller has a dilemma: they have three independent ideas and aren’t sure whether they should eliminate any of them. How can they make the best 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.com Be on the show: SideHustleSchool.com...

Mar 30, 20225 minEp 1915Transcript available on Metacast