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

#1974 - Q&A: “If everyone learns SEO, how can you ever win?”

Should you bother trying to optimize your website for search engines? Our caller wonders if it’s an arms race that no one can win. 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...

May 28, 20224 minEp 1974Transcript available on Metacast

#1973 - Failure Friday: “Offensive Greeting Cards” Lost in Post

In this week’s Failure Friday segment, we hear from the founder of a line of “rude, offensive greeting cards” in the UK. As his business grew, he turned to overseas suppliers for a big holiday shipment. You might guess what happens next! 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...

May 27, 20227 minEp 1973Transcript available on Metacast

#1972 - TBT: Mixed Media Artist Sews Up Side Earnings

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a New Hampshire fabric artist. She’s built a seamless business while working a day job in IT. 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: SideHu...

May 26, 20226 minEp 1972Transcript available on Metacast

#1971 - Q&A: “Is it ever too early to post on social media?”

At what point in your new hustle should you start posting on social media—should it be before you even have a product or service, or is it better to wait? 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...

May 25, 20224 minEp 1971Transcript available on Metacast

#1970 - Charcuterie Boards Cure Couple's Pandemic Woes

A midwestern couple makes cash out of catastrophe, reinventing themselves during the 2020 lockdown. 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 I...

May 24, 20226 minEp 1970Transcript available on Metacast

#1969 - First $1,000: “I couldn’t believe I got paid playing a game I loved…”

In this week’s First $1,000 segment, we hear from the founder of StartPlaying.Games, a hub for professional dungeon masters who facilitate tabletop games at private events. 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...

May 23, 20226 minEp 1969Transcript available on Metacast

#1968 - Q&A: “I’m trying to sell tickets to a Mexican version of Bingo…”

A caller from Mexico City is starting a Lotería, a Mexican version of Bingo. How can she get people to buy tickets? 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: @chrisguilleb...

May 22, 20225 minEp 1968Transcript available on Metacast

#1967 - Q&A: "I got a nasty email from my competitor..."

This listener just heard from their competition—and the competition isn’t happy. How should they respond? 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 Connec...

May 21, 20225 minEp 1967Transcript available on Metacast

#1966 - Failure Friday: “80% of our customers never returned…”

In this week’s Failure Friday segment, we hear from the founder of Plate Crate, a baseball-themed subscription service. Business was going great–but when he decided to upgrade the website, the count quickly went against him. 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 Emai...

May 20, 20226 minEp 1966Transcript available on Metacast

#1965 - TBT: Adventurous Kitchen Tool Set Goes Global

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of QD Foodie, a kitchen tool collection that makes cooking fun. Her products are now sold in houseware stores across the U.S. and direct to customers worldwide. 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...

May 19, 20227 minEp 1965Transcript available on Metacast

#1964 - Q&A: “Why do people buy courses when YouTube is free?”

If knowledge is free, why does anyone pay for it? 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: @193countries Visit Chris's main site: C...

May 18, 20226 minEp 1964Transcript available on Metacast

#1963 - Head-to-Toe Holistic Skincare Biz Shows Moxie

With startup costs of $150 from a tax refund, this single mom teaches the science of healthy skin with simple, small batch skincare products. 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...

May 17, 20226 minEp 1963Transcript available on Metacast

#1962 - First $1,000: Bulldog Blogger Builds Bow-Wow Biz

In this week’s First $1,000 segment, we hear from the creator of FrenchieJourney.com, a boisterous blog and bedazzling resource for fans of French bulldogs. 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/qu...

May 16, 20228 minEp 1962Transcript available on Metacast

#1961 - Q&A: “What are the most profitable niches for teaching?”

Some topics or niches are much more profitable than others. Today’s caller is wondering if we can cut to the chase and just give him a list. Fair enough! 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...

May 15, 20225 minEp 1961Transcript available on Metacast

#1960 - Q&A: “How can I get YouTube’s algorithm to like me??”

Today’s caller is making a YouTube series, but not getting the traction he’d like. Is there anything he can do to have his videos seen by more people? 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/question...

May 14, 20226 minEp 1960Transcript available on Metacast

#1959 - Failure Friday: “Switchasaurus” Card Game Almost Goes Extinct

In this week’s Failure Friday segment, we hear from the inventor of “Switchasaurus,” a dinosaur card game. When his first supplier under delivers, he tries to evolve. 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...

May 13, 20228 minEp 1959Transcript available on Metacast

#1958 - TBT: Boise Woodworking Team Upgrades Toolkit

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an Idaho woodworker. As more people have moved to the area, his business has taken 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSc...

May 12, 20227 minEp 1958Transcript available on Metacast

#1957 - Q&A: “I have a tricky ethical situation with my day job…”

What happens when your day job brings you a lead for your side hustle? This caller faces an ethical dilemma, as well as a practical 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 Be on the show: SideHustleSchool.com/questions Connect on T...

May 11, 20225 minEp 1957Transcript available on Metacast

#1956 - College Student Turned Fashion Influencer Earns $140,000

Fascinated by the influencer life, a university student creates a fashion blog that earns real money, thanks to SEO and Pinterest. 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...

May 10, 20228 minEp 1956Transcript available on Metacast

#1955 - First $1,000: Digital Art Reaches Physical Homes Worldwide

In this week’s First $1,000 segment, we hear from the co-founders of Wandercolors. Together, they produce digital art of iconic travel destinations. 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 ...

May 09, 20226 minEp 1955Transcript available on Metacast

#1954 - Q&A: “I’m giving lots of consultations, but making few sales…”

Today’s listener is experiencing lots of demand for the free version of her coaching offer, but not the paid one. Let’s see if we can help 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. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money wi...

May 08, 20226 minEp 1954Transcript available on Metacast

#1953 - Q&A: “I think my client ghosted me…”

We’ve all been there—ghosted by someone we liked. In this case, a designer nearly lands the perfect client, but then the client goes AWOL. What can we learn from the 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 on the show: Si...

May 07, 20225 minEp 1953Transcript available on Metacast

#1952 - Failure Friday: “I naively thought the influencers would bring sales…”

In this week’s Failure Friday segment, we hear from an Australian who owns an ecommerce business offering mindful toys and gifts. Following a rebrand, she pays Instagram influencers to create interest—but mostly they just took her 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...

May 06, 20225 minEp 1952Transcript available on Metacast

#1951 - TBT: “Mozart for Munchkins” Gives Encore Performance

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Mozart for Munchkins. The group produces concerts and musical experiences for children of all ages in New York 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@sideh...

May 05, 20227 minEp 1951Transcript available on Metacast

#1950 - Q&A: “Can you really just right-click and save an NFT?!”

Today’s caller wants to know: can you really right-click and save someone else’s NFT to your computer? And if you can, can you then sell it yourself? (I love the thinking here!) 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: Si...

May 04, 20226 minEp 1950Transcript available on Metacast

#1949 - Travel Membership Program Earns $300,000/Year

This travel writer found the ticket to a thriving membership site, helping families book airfare for less. Wheels 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 notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguill...

May 03, 20227 minEp 1949Transcript available on Metacast

#1948 - First $1,000: “I took a salary cut of fifty per cent…”

In this week’s First $1,000 segment, we hear from a globetrotting Australian who owns an ad agency. He took a 50% salary cut to learn about the early model of pay-per-click advertising, but the decision paid off 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...

May 02, 20228 minEp 1948Transcript available on Metacast

#1947 - Q&A: “I’m overwhelmed with too many inquiries…”

Today’s caller has a different sort of problem than most people who struggle to get off the ground: her business is going so well that she’s feeling overwhelmed with the work. 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: Side...

May 01, 20225 minEp 1947Transcript available on Metacast

#1946 - Q&A: “’Spaced repetition’ practice with overseas tutors?”

Today’s listener has an intriguing idea: to aid in memory retention using spaced repetition—but with outsourced tutors from other countries. Think of it like “Upwork meets Coursera.” Will it work? 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...

Apr 30, 20226 minEp 1946Transcript available on Metacast

#1945 - Failure Friday: “They just weren’t interested in what we were selling…”

In this week’s Failure Friday segment, we hear from the co-owner of a business that livestreams weddings. When Covid struck, they thought they had the perfect opportunity to expand to a new market—but buyer interest fizzled. 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 Emai...

Apr 29, 20227 minEp 1945Transcript available on Metacast