Chris Guillebeau
Side Hustle School
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.
Vizitează neapărat site-ul podcastului și susține-i creatorul: sidehustleschool.com
Autor
Chris Guillebeau
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Site-ul podcastului
Cel mai nou episod
25 oct. 2026
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Episoade
Ep. 3262 - Q&A: “Should I raise my coaching rates or add more clients?” 06.12.2025 5:08
Today's caller has two levers—charge a bit more or work a bit more. We'll test both in plain numbers, then show why nudging the price usually wins for a solo coach. 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 ea...
Ep. 3261 - Q&A: “Is my struggling side hustle worth saving?” 05.12.2025 5:42
A listener wants to know if a slow start is normal, or a warning sign that another business might be better. We'll set a simple 90-day experiment to decide whether to double down, redesign, or walk away. 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...
Ep. 3260 - TBT: Campaign Scheduling Tool Turns Out Voters 04.12.2025 5:14
In this week's Throwback Thursday segment, find out how a small campaign tool turned into a software product now licensed by multiple counties. 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: SideHu...
Ep. 3259 - STORY: Accountant Earns Six-Figures Selling Spreadsheets to Etsy Sellers 03.12.2025 7:32
She was burned out being a CPA, so she turned her efforts to an Etsy business—but it wasn't long before she was hitting the books again, just in a more creative way. Her new spreadsheets help Etsy sellers and earn a six-figure income for 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 ye...
Ep. 3258 - Q&A: “Can I profit from flipping open-box customer returns?” 02.12.2025 4:53
Today's listener wants to turn store returns into cash. We'll cover how to evaluate a pallet, estimate true margins, and avoid getting stuck with dead inventory. 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....
Ep. 3257 - First $1,000: DIY Headshot Stations for University Job Fairs 01.12.2025 5:29
In this week's First $1,000 segment, campus recruiters needed polished LinkedIn photos—but photographers were booked solid. One creative grad built a plug-and-play headshot booth, rented it four times in a month, and snapped up his first grand without clicking the shutter himself. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mo...
Ep. 3256 - Weekend Workshop: Building Teams Without Hiring Employees 30.11.2025 7:45
This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it's all free. Today's topic: a small-scale, large-reach transcription business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting t...
Ep. 3255 - Q&A: “When is uneven side-hustle income safe to rely on?” 29.11.2025 4:38
Today's caller makes more money on weekends than at the day job—but their revenue graph looks like a heart monitor. Can they rely enough on their extra income to go all-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...
Ep. 3254 - Q&A: “How do I price my VA work for true value?” 28.11.2025 4:25
If clients praise your speed but you're still billing like a beginner, it's time to level up. Today we pinpoint the three value levers that justify higher VA rates—and a script that keeps loyal clients on board. 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 guid...
Ep. 3253 - TBT: Scarce Lego Sets Build Value Over Time 27.11.2025 6:12
In this week's Throwback Thursday segment, find out how one patient side hustler stockpiled retired LEGO sets, held them like collectibles, and eventually parlayed the profits into a full-on store. 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 liste...
Ep. 3252 - STORY: Frenchman Says Bonjour to $35,000/Month Foodie Hustle 26.11.2025 7:55
After relocating to Quebec, this continental creative brings seasonal flavor to an artisanal food retailing biz. 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...
Ep. 3251 - Q&A: “Is my burnout a signal to pivot?” 25.11.2025 5:06
Are you just tired—or do you need a bigger break? In this episode, we'll help a listener take a stress-test to know if they need rest, a redesign, or a full business pivot. 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...
Ep. 3250 - First $1,000: Digital Window Menu Boards for Food Trucks 24.11.2025 5:54
In this week's First $1,000 segment, a designer helps food trucks and pop-up restaurants get rid of chalk dust and update to the digital age. 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: SideHust...
Ep. 3249 - Weekend Workshop: From Ski Bum to Six-Figure Teacher 23.11.2025 7:01
This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it's all free. Today's topic: an online snow-skiing school. 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,...
Ep. 3248 - Q&A: “Should I spend $2,000 on retention or acquisition?” 22.11.2025 5:12
Today's caller runs a tiny subscription app and has two grand to spend. Should that money patch cancelations or chase new sign-ups? We'll do the napkin math and land on a clear next 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&...
Ep. 3247 - Q&A: “Instagram, TikTok, or LinkedIn—how do I choose?” 21.11.2025 5:19
Posting everywhere spreads you thin; posting in the right place compounds momentum. Today we break down a three-question filter that shows exactly where this side hustler's wallets should live first. 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 lis...
Ep. 3246 - TBT: Recruiters Pay Me to Tear Apart Their Emails 20.11.2025 5:31
In this week's Throwback Thursday segment, hear how one copy-savvy side hustler turned a collection of recruiter emails into a paid “swipe file,” and then built a monthly subscription around 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...
Ep. 3245 - STORY: Six-Figure Beekeeping Biz Buzzes for Minnesota Couple 19.11.2025 6:42
The buzzworthy journey of Minnesotan bees and their keepers. These hardy bees don't mess around—last year they produced $150,000 in sweet profits. 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...
Ep. 3244 - Q&A: “How do I upsell without sounding pushy?” 18.11.2025 4:19
Great contracting work often reveals the next problem to solve. Here's a simple script that turns an “upsell” into an obvious win for the client—and leaves everyone feeling good about the extra invoice. 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 g...
Ep. 3243 - First $1,000: Cozy Reading Gadget Turns Pages and Profit 17.11.2025 6:13
A bedtime-reading addict bend a paperclip into a page holder, refines it into a soft-touch clip, and flips his ledger from red ink to a four-figure 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 note...
Ep. 3242 - Weekend Workshop: “Digital Documentation” Earns Passive Income 16.11.2025 8:02
This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it's all free. Today's topic: how a single PDF guide earned $120,000 in its first year. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without qui...
Ep. 3241 - Q&A: “Is remote-worker visa consulting a real business?” 15.11.2025 5:58
Remote-worker visas are booming—and bewildering. Today we price a “visa concierge,” unpack simple liability safeguards, and gauge whether the market can pay more than pocket change. 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 lis...
Ep. 3240 - Q&A: “Should I tell my clients I’m using AI?” 14.11.2025 5:16
AI tools can double your output, but not everyone's comfortable with it. Today we map a three-part policy for disclosing AI use that keeps trust high, quality higher, and clients on board. 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&...
Ep. 3239 - TBT: This Tiny Spreadsheet Tool Pays the Rent 13.11.2025 5:54
In this week's Throwback Thursday segment, meet a side hustler who built a simple browser-based spreadsheet tool. It earns enough to cover his rent each 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. Sh...
Ep. 3238 - STORY: Agricultural Teacher Earns $200,000 Selling Lesson Plans 12.11.2025 7:19
After creating course materials for a forgotten group of educators, this agricultural teacher now earns a significant income from a growing 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...
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