Best Pivoting Out Of The Classroom Podcasts (2025)

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Ep. 3250 - First $1,000: Digital Window Menu Boards for Food Trucks 6:00

Play Pause

9m ago6:00

6:00

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&…

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Ep. 3249 - Weekend Workshop: From Ski Bum to Six-Figure Teacher 7:07

20h ago7:07

7:07

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 m…

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Ep. 3248 - Q&A: “Should I spend $2,000 on retention or acquisition?” 5:18

2d ago5:18

5:18

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 sho…

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Ep. 3247 - Q&A: “Instagram, TikTok, or LinkedIn—how do I choose?” 5:25

3d ago5:25

5:25

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 y…

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Ep. 3246 - TBT: Recruiters Pay Me to Tear Apart Their Emails 5:38

4d ago5:38

5:38

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, …

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Ep. 3245 - STORY: Six-Figure Beekeeping Biz Buzzes for Minnesota Couple 6:49

5d ago6:49

6:49

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 listen…

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Ep. 3244 - Q&A: “How do I upsell without sounding pushy?” 4:26

6d ago4:26

4:26

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. Thi…

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Jenelle McClenahen - How to Build an Edtech Start-Up 33:50

7d ago33:50

33:50

Jenelle McClenahen is the CEO & Founder of Symplifyed, a company born from her firsthand experience as a classroom educator. What began as a way to survive a chaotic year in her own classroom turned into a powerful system of intentional goal-setting and progress-monitoring that delivered transformative student growth. Her work is driven by the deep…

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Ep. 3243 - First $1,000: Cozy Reading Gadget Turns Pages and Profit 6:20

7d ago6:20

6:20

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 …

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Ep. 3242 - Weekend Workshop: “Digital Documentation” Earns Passive Income 8:08

8d ago8:08

8:08

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 studie…

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Ep. 3241 - Q&A: “Is remote-worker visa consulting a real business?” 6:05

9d ago6:05

6:05

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 incl…

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Ep. 3240 - Q&A: “Should I tell my clients I’m using AI?” 5:22

10d ago5:22

5:22

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 sh…

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Ep. 3239 - TBT: This Tiny Spreadsheet Tool Pays the Rent 6:00

11d ago6:00

6:00

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 lesso…

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Angela Maiers - Redefining Success 56:26

12d ago56:26

56:26

Futurist. Innovator. Educator. Entrepreneur. Change Maker. Angela Maiers is on a relentless mission to disrupt the status quo and empower individuals everywhere to transform their own world—and the world around them. As the founder of the global movement Choose2Matter, Angela’s singular focus is to help people realize their value and potential cont…

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Ep. 3238 - STORY: Agricultural Teacher Earns $200,000 Selling Lesson Plans 7:25

12d ago7:25

7:25

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 lis…

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Ep. 3237 - Q&A: “Will professionals trade hours instead of cash?” 4:41

13d ago4:41

4:41

Can busy side hustlers trade skills instead of dollars? Today we outline a lean time-bank model—simple rules, low overhead, and real incentives to keep everyone honest. 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 gui…

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Ep. 3236 - First $1,000: Turning Cable Chaos into Magnetic Profit 5:58

14d ago5:58

5:58

Tired of cables dangling each time your standing desk rises? A quick TikTok clip of magnetic rails snapping cords into place sparked a rush of orders for this savvy side hustler. 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 include…

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Ep. 3235 - Weekend Workshop: The Wandering Teacher's Global Classroom 8:15

15d ago8:15

8:15

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 early language hacker starts “Fluent in 3 Months.” Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of…

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Ep. 3234 - Q&A: “What’s a fair founder-investor deal between friends?” 5:35

16d ago5:35

5:35

Cash can launch the product; labor will keep it alive. Today we map out founder-friendly splits, vesting schedules, and a simple “dynamic equity” formula that grows with effort. 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…

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Ep. 3233 - Q&A: “Where do I find my first paying customer?” 4:56

17d ago4:56

4:56

One sale beats a hundred compliments. Let’s walk through a low-risk, weekend-ready plan that puts money in this side hustler’s hands within two weeks. 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 li…

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Ep. 3232 - TBT: The Garage Gym Hustle That Went Digital 6:00

18d ago6:00

6:00

In this week’s Throwback Thursday segment, learn how one fitness fan turned flipping gym equipment into a small media business. He now sells setup guides and curates weekly home gym deals for thousands of subscribers. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting…

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Ep. 3231 - STORY: The Coffee Grinder That Made $300,000 8:25

19d ago8:25

8:25

Rise and shine! A petroleum engineer finds the perfect item to resell on Amazon. He goes on to sell $300,000 worth of the humble coffee grinder. 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…

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Ep. 3230 - Q&A: “How do I test Facebook vs. free traffic?” 5:22

20d ago5:22

5:22

Free traffic feels safe, but paid ads might unlock a faster lane—IF the math checks out. Let’s design a two-week, $200 ad test with clear “go / no-go” numbers so this side hustler can see truth, not guesswork. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their j…

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Dr. Amy Mathews-Perez - The Journey to Self 36:23

21d ago36:23

36:23

Texas-born & raised, Dr. Amy Mathews-Perez has recently retired from 34 years of working in public education where she served as a General Ed. Teacher, SLP, Diagnostician, SPED Supervisor, Principal, Assistant Principal and a Director of Special Education. While her journey of public-school service has come to an end, she now puts energy, effort & …

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Ep. 3229 - First $1,000: Shopify Library Becomes Paid Subscription 6:45

21d ago6:45

6:45

Shopify merchants kept begging forums for the same quick theme fixes. One developer bundled all his proven snippets behind a $15 monthly paywall—and 170 store owners are happily copying, pasting, and paying. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job…

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Ep. 3228 - Weekend Workshop: When Getting Fired Becomes Your Best Break 7:15

22d ago7:15

7:15

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: if he hadn’t been pushed, he wouldn’t have made the leap. Side Hustle School features a new episode EVERY DAY, featuring detailed case studie…

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Ep. 3227 - Q&A: “Why won’t TikTok followers join my newsletter?” 5:19

23d ago5:19

5:19

TikTok, Snap, and Instagram fame is fun, but e-mail tends to pay the bills. Today we lay out the follower-to-inbox conversion math, including the moment a list becomes non-negotiable. 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 in…

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Ep. 3226 - Q&A: “Can I legally profit from salvaging barn wood?” 5:03

24d ago5:03

5:03

Old barns can be gold mines—or legal landmines. Today we cover permits, insurance, and realistic margins for turning reclaimed boards into profit. 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 listen…

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Ep. 3225 - TBT: A Guided Journal, a Friend in Need, and 1,000+ Sales 5:59

25d ago5:59

5:59

In this week’s Throwback Thursday segment, learn how a creative project for a friend in recovery became a business, eventually leading to a partnership with a Washington, DC nonprofit. 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 i…

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Ep. 3224 - STORY: Line Chef Makes Millions Cooking Up Apron Empire 7:41

26d ago7:41

7:41

A chef sets out to reinvent the humble apron, growing it to a multi-million-dollar company while still working in restaurants at night. 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 seve…

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Ep. 3223 - Q&A: “When does a logo actually matter?” 4:37

27d ago4:37

4:37

Today’s caller wonders whether to polish the package or finish the product. We’ll set a two-checkpoint rule that keeps creativity flowing, without turning branding into busywork. 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 include…

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Viviana Vazquez - From Creating Lesson Plans to Creating Wealth 46:17

28d ago46:17

46:17

🚀 Passionate Growth Marketer | Financial Technology | Founder of First-Gen Wealth, LLC | MBA Candidate 🔍 Strategizing impactful content in the Financial Technology startup realm for over 6 years, leading dynamic teams of copywriters, agencies, while building brands and growing organic channels. 🌱 Founder of OGP by First-Gen Wealth LLC, a brand reac…

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Ep. 3222 - First $1,000: “CRM Makeovers” for Real Estate Agents 5:56

28d ago5:56

5:56

In this week’s First $1,000 segment, meet the HubSpot whiz who charges Realtors $500 for a three-hour CRM detox—merging duplicates, tagging leads, and automating follow-ups before lunch. 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…

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Ep. 3221 - Weekend Workshop: The Premium Pricing Paradox 7:19

29d ago7:19

7:19

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: the $100 Alaska coupon book that sells over and over. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of…

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Ep. 3220 - Q&A: “When is business coaching worth the cost?” 5:35

1M ago5:35

5:35

Coaching can fast-track growth—or drain a lot of money from your bank account. In this short episode, you’ll learn a simple metric to decide whether a pricey mentor is a smart bet or a motivational luxury. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. …

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Ep. 3219 - Q&A: “Can I sell carbon-offset checks to small brands?” 5:54

1M ago5:54

5:54

Green-washing headlines have everyone nervous, and for good reason. Today we design a “quick-check” carbon-audit service small brands will pay for—and keep the workload under two hours per client. 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…

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Ep. 3218 - TBT: I Built a Supplement Guide People Actually Trust 5:50

1M ago5:50

5:50

In this week’s Throwback Thursday segment, learn how a side hustler built a trustworthy supplement guide from one TikTok video, turning it into a $40,000 affiliate 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 fre…

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Ep. 3217 - STORY: Aussie Stretches Out with Online Store for Tall Women 7:02

1M ago7:02

7:02

Tall women everywhere rejoice as an eCommerce side hustle brings new meaning to ‘top shelf.’ 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: SideHustleS…

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Ep. 3216 - Q&A: “How do I avoid a garage full of unsold kits?” 5:05

1M ago5:05

5:05

Should you spend months growing followers or risk cash on inventory right away? Today we outline a “test-then-preorder” strategy that proves demand in weeks, pays for production up front, and builds your email list as you go. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without …

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Ep. 3215 - First $1,000: Board-Game Date Nights in a Café Basement 5:54

1M ago5:54

5:54

In this week’s First $1,000 segment, hear how a board-game collector transformed an unused café basement into a candle-lit playground for couples. 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 listen…

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Dr. Sonia Matthew, NBCT - Heart-Led 39:01

19d ago39:01

39:01

Dr. Sonia A. Matthew, NBCT Dr. Sonia Matthew, the 2025 Maryland’s National Outstanding Assistant Principal of the Year recognized by both the Maryland Association of Elementary School Principals (MAESP) and the National Association of Elementary School Principals (NAESP), brings 27 years of experience in public education. Her career spans roles as …

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Ep. 3214 - Weekend Workshop: From Spreadsheets to Six Figures 7:04

1M ago7:04

7:04

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: the original spreadsheet king. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra …

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Ep. 3213 - Q&A: “Can I monetize a college scholarship database?” 5:01

1M ago5:01

5:01

Obscure college scholarships are gold, at least if parents trust your data. In this episode we design a subscription, ROI guarantee, and tech stack that can turn a spreadsheet into monthly 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…

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Ep. 3212 - Q&A: “Will people pay for AI-optimized resumés?” 5:09

1M ago5:09

5:09

Cheap resumé bots and pricey human writers leave a gap. We’ll show how an AI-plus-expert service can fill it, both profitably and credibly. 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 …

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Ep. 3211 - TBT: Built in a Weekend, Used by Thousands 5:11

1M ago5:11

5:11

In this week’s Throwback Thursday segment, hear how a side project built over a single weekend turned into a surprisingly steady income stream, all thanks to a clunky but useful Chrome extension with 5,000 loyal users. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quittin…

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Dr. Tina Flores, PMP - Talent Secrets 27:47

23d ago27:47

27:47

Dr. Tina Flores is a Talent Acquisition leader, strategic career advisor, and business aficionado. She helps businesses and individuals survive the hiring process, lead better, and achieve more through emotionally intelligent strategies. With nearly two decades of experience in Talent Acquisition, coachsulting prowess, and operational excellence, T…

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Ep. 3210 - STORY: Canadian Bidets Modernize Bathroom Life 7:42

1M ago7:42

7:42

In several parts of the world, bidets are used in lieu of toilet paper—but why not in Canada? One man sets out to change that, flushing away discouragement and banking 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 …

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Ep. 3209 - Q&A: “How do I use exit pop-ups?” 4:44

1M ago4:44

4:44

A well-timed nudge can rescue sales, but only if it feels like service, not a race to the bottom. Let’s design a polite “please stay” offer that boosts revenue without creating coupon addicts. 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, th…

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Ep. 3208 - First $1,000: Vintage Sewing Machine Rehab Workshops 5:29

1M ago5:29

5:29

In this week’s First $1,000 segment, meet the maker who buys twenty-dollar thrift-store sewing machines, teaches students to revive them, and lets each participant leave with a fully functioning vintage Singer. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their …

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Ep. 3207 - Weekend Workshop: The Global Photography Pivot 6:45

1M ago6:45

6:45

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 nomadic photography business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra…