Side Hustle School

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Episodes

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Side Hustle School

Chris Guillebeau / Onward Project•sidehustleschool.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

#2394 - Q&A: “Should I become a financial advisor for healthcare workers?”

Today’s caller works as a data analyst in the health sector, but she's also got a keen interest in investing. Might there be a way to combine these talents for one side hustle to rule them all? 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...

Jul 22, 2023•5 min•Ep 2394•Transcript available on Metacast

#2393 - Failure Friday: Ghost Tours Fail to Scare Enough Clients

In this week’s Failure Friday segment, we hear a spooky story: an attempt at offering a ghost tour of Denver fails to scare enough people into signing 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/ques...

Jul 21, 2023•6 min•Ep 2393•Transcript available on Metacast

#2392 - TBT: Game Consoles, VCRs, and Typewriters for Sale

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a reseller who specializes in retro electronics including vintage game consoles and typewriters. 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: Sid...

Jul 20, 2023•6 min•Ep 2392•Transcript available on Metacast

#2391 - Q&A: “How to sell a ‘Democracy in Action’ program?”

A listener looking to inspire others to become more active in their local government wants to start a subscription service of some kind. 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...

Jul 19, 2023•6 min•Ep 2391•Transcript available on Metacast

#2390 - Q&A: “Can I tell someone else’s story on my podcast?”

If you make a storytelling podcast, can you tell someone else’s story without their permission? 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 Insta...

Jul 18, 2023•5 min•Ep 2390•Transcript available on Metacast

#2389 - First $1,000: Indian Tutor Helps U.S. High School Students Learn Math

In this week’s First $1,000 segment, we hear from an Indian listener. He’s built a bustling business as an online math tutor for high school students in the U.S. 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.c...

Jul 17, 2023•6 min•Ep 2389•Transcript available on Metacast

#2388 - Q&A: “What should I sell on Fiverr?”

A digital nomad with a range of skills wants to offer services on Fiverr. How should he specialize to be most efficient and profitable? 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...

Jul 16, 2023•6 min•Ep 2388•Transcript available on Metacast

#2387 - Q&A: “It’s hard to compete with bigger firms!”

A talented designer is facing competition with larger design firms in her area. How can she stand out and make her mark? 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: @chrisgu...

Jul 15, 2023•5 min•Ep 2387•Transcript available on Metacast

#2386 - Failure Friday: Homemade Hummus Subscription Fails to Smash

In this week’s Failure Friday segment, we hear from a listener with a tangy idea. Drawing on her Lebanese ancestry, she tries to create a “homemade hummus subscription box. Alas, those chickpeas failed to smash themselves into a hit. 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...

Jul 14, 2023•7 min•Ep 2386•Transcript available on Metacast

#2385 - TBT: Project Manager Side Hustles as Home Inspector

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a project manager in the construction industry who has a side hustle as a home inspector. This second job earns several thousand dollars a 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 Ema...

Jul 13, 2023•6 min•Ep 2385•Transcript available on Metacast

#2384 - Q&A: “How to use the Pomodoro method in my side hustle?”

The Pomodoro method is a classic productivity tool. How can this listener—or anyone—use it when building their 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: @chri...

Jul 12, 2023•6 min•Ep 2384•Transcript available on Metacast

#2383 - Q&A: “Need help attracting first clients…”

A sales coach for Etsy and Shopify sellers is looking to expand her initial client base of friends and family members. 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...

Jul 11, 2023•5 min•Ep 2383•Transcript available on Metacast

#2382 - First $1,000: Airbnb Marketer Increases Rental Rates 30%

In this week’s First $1,000 segment, we hear from a guy who helps Airbnb property owners and managers grow their listings and revenue. 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...

Jul 10, 2023•6 min•Ep 2382•Transcript available on Metacast

#2381 - Q&A: “Should I build a website for my freelance coding hustle?”

Does this freelance programmer need a website? If so, what’s the simplest and most effective way to make 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 Con...

Jul 09, 2023•5 min•Ep 2381•Transcript available on Metacast

#2380 - Q&A: “How do I pinpoint the right side hustle idea?”

A recent college graduate needs help choosing a side hustle that aligns with her professional skills and personal passions. 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...

Jul 08, 2023•6 min•Ep 2380•Transcript available on Metacast

#2379 - Failure Friday: “SnoozeCubes” Hustle Experiences Sleepy Sales

In this week’s Failure Friday segment, we hear from the founder of SnoozeCubes, sleeping pods for offices. If you haven’t heard of this business, it’s because it never got up to Super Bowl ad-level. 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.c...

Jul 07, 2023•7 min•Ep 2379•Transcript available on Metacast

#2378 - TBT: Copyeditor Proofreads Tech Reports & Marriage Proposals

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a tech employee who moonlights as a freelance copyeditor and proofreader. 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...

Jul 06, 2023•6 min•Ep 2378•Transcript available on Metacast

#2377 - Q&A: “Can I create a fictional character for Cameo shoutouts?”

Last month we talked about buying Cameo shoutouts to promote a business. This caller has a different idea: can they create a *fictional* character and offer shoutouts for sale? 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: Sid...

Jul 05, 2023•6 min•Ep 2377•Transcript available on Metacast

#2376 - Q&A: “OpenTable isn't good, how can we do better?”

Today’s caller wants to make an alternative to restaurant reservations. He’s got ten years of experience in the industry, but will that be enough to create a platform at scale? 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: Sid...

Jul 04, 2023•5 min•Ep 2376•Transcript available on Metacast

#2375 - First $1,000: “Logo Lady” of Upwork Builds Design Speciality

In this week’s First $1,000 segment, we hear from an HR specialist who’s also known as the “Logo Lady” of Upwork. She does only logos, which has been key to her success, and allows her to earn a good side income in a manageable number of hours. 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...

Jul 03, 2023•6 min•Ep 2375•Transcript available on Metacast

#2374 - Q&A: “Can you grow a side hustle using Reddit?”

Reddit is known as “the front page of the internet.” Can it also be a viable way to grow your business or 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: @chrisguil...

Jul 02, 2023•6 min•Ep 2374•Transcript available on Metacast

#2373 - Q&A: “Should I feel bad about side hustling at work?”

This caller is running her side hustle on company time. How do we feel about that? 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: @193cou...

Jul 01, 2023•5 min•Ep 2373•Transcript available on Metacast

#2372 - Failure Friday: “Hangover Helper” Business Sobers Up

In this week’s Failure Friday segment, we hear from a San Francisco man with a dream to serve party goers who had partied a little too hard. Unfortunately, this idea soon encountered a sobering reality. 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...

Jun 30, 2023•6 min•Ep 2372•Transcript available on Metacast

#2371 - TBT: Coder By Day, Cockatiel Companion By Night

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a remote programmer who pet-sits in different states for weeks at a 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 show: SideHustleSchool.com/quest...

Jun 29, 2023•6 min•Ep 2371•Transcript available on Metacast

#2370 - Q&A: “What are some mediums besides blogs, podcasts, and YouTube?”

You’ve heard about blogging, podcasting, and making videos for YouTube—but if none of those options sound appealing, are there others? 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...

Jun 28, 2023•5 min•Ep 2370•Transcript available on Metacast

#2369 - Q&A: “Separating business and personal expenses…”

This personal trainer is struggling with separating his personal and business finances. Can we give him a boost so he can get back to focusing on push-ups? 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...

Jun 27, 2023•5 min•Ep 2369•Transcript available on Metacast

#2368 - First $1,000: Smartphone Photography Instructor Snaps Up Profit

In this week’s First $1,000 segment, we hear from an Austinite who operated a side hustle teaching people to take better photos with their smartphones. He did this for two years before moving on to a new project. 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@side...

Jun 26, 2023•6 min•Ep 2368•Transcript available on Metacast

#2367 - Q&A: “Designing tiny homes for vacation rentals…”

In today’s episode, a caller from Israel wants to create sustainable tiny homes for vacation rentals. How can we help them along? 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:...

Jun 25, 2023•5 min•Ep 2367•Transcript available on Metacast

#2366 - Q&A: “Why don’t you self-publish your books?”

These days, self-publishing is easy and affordable. In this episode, an aspiring author wonders about MY books: why do I still work with a traditional publisher?? 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....

Jun 24, 2023•6 min•Ep 2366•Transcript available on Metacast

#2365 - Failure Friday: On-Demand Haiku Poet Shows Restraint

In this week’s Failure Friday segment, we hear from an aspiring poet who wants to get paid for on-demand haiku at public events. Unfortunately, the idea is a bust. 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...

Jun 23, 2023•6 min•Ep 2365•Transcript available on Metacast