Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau 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.

Hosted on Acast. See acast.com/privacy for more information.

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Episodes

#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

#1884 - Q&A: What if you don't want to use social media?

This listener thinks social media is overexposed and ineffective, at least when it comes to their business. If you’re not into hashtags and selfies, can you skip it altogether? 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...

Feb 27, 20225 minEp. 1884

#1883 - Q&A: How can I fund my quest to run across the country?

Today’s caller wants to—wait for it—run across the United States. What an incredible, audacious goal! But of course she needs funding, and she wants to think creatively. What are her options? 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 o...

Feb 26, 20225 minEp. 1883

#1882 - Failure Friday: “I dropped out of Stanford and left my business at the same time…”

In this week’s Failure Friday segment, we hear from Bryan Quoc Le, a scientist and food blogger. His early days of selling vegan banana ice cream at Stanford felt promising, but soon turned into too much to handle. 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@si...

Feb 25, 20227 minEp. 1882

#1881 - TBT: Orthodontist Invents Modern Tool for Impacted Teeth

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a North Carolina orthodontist who invents a better way to treat impacted teeth. Gold chains belong in the 1980s! 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 ...

Feb 24, 20228 minEp. 1881

#1880 - Q&A: “I’d like to lead a cross-country caravan tour…”

Can you get paid to lead a cross-country caravan with dozens of vehicles in a cross-country road trip? That’s what this caller envisions. 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 ...

Feb 23, 20225 minEp. 1880

#1879 - Online Literacy Tutoring Proves Profitable

A literacy teacher feeling frustrated with administration decides to strike out on her own, creating a surprisingly resilient business model with multiple streams of 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: team@sidehustleschool.com Be on the show: SideHu...

Feb 22, 20228 minEp. 1879

#1878 - First $1,000: “After 9 months, we got our first $50 sponsorship…”

In this week’s First $1,000 segment, we hear from Kelan Kline, co-founder of TheSavvyCouple.com. It took Kelan and his wife a while to get going, but the blog eventually became a multiple 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 Email: team@sidehust...

Feb 21, 20229 minEp. 1878

#1877 - Q&A: How do I best prioritize what to do next?

She’s selling a set of planners for new moms struggling with postpartum depression. How can she reach the target market with her product? 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 ...

Feb 20, 20225 minEp. 1877

#1876 - Q&A: Get paid to drive a stranger’s car across the country?

Today’s question brings me back to one of my long-ago lifelong goals. Can you get paid to drive someone’s car across the country when they relocate?? 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...

Feb 19, 20224 minEp. 1876

#1875 - Failure Friday: “I started to realize how little I knew…”

In this week’s Failure Friday segment, we hear from Danielle Winton, a furniture reseller in Missouri. Business was going along smoothly, until she took on a project that proved to be much tougher than expected. 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...

Feb 18, 20226 minEp. 1875

#1874 - TBT: Soap Opera Star Becomes Professional Organizer

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Regina Leeds, an actress in Los Angeles who left a career in soap opera to become an author and professional organizer. 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....

Feb 17, 20228 minEp. 1874

#1873 - Q&A: “Fly as an airline courier” ... is that a thing?

Today’s caller has seen ads about becoming an independent airline courier. It sounds fun—but is this a viable business opportunity, a scam, or something else? 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/...

Feb 16, 20225 minEp. 1873

#1872 - Voiceover Couple Averages $4,500/Month

This voice actor couple is stepping up to the mic, building a legacy with A-list clients and creating generational wealth for their family. 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 o...

Feb 15, 20228 minEp. 1872
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