767 episodes
- Can 100 pieces of content really replace your day job? One YouTuber says yes, and he's doing it with reviews and tutorials that still pay him months after he hits publish.
Jacob Wade runs Roadmap Money, a personal finance YouTube channel built almost entirely on search traffic and affiliate commissions.
He started by writing about budgeting apps and savings accounts for years, but it wasn't until he brought that same expertise to YouTube that things clicked.
One video, "best budgeting apps of 2024," started pulling in daily search traffic.
Nine months ago he had around 7,000 subscribers. Today he's closing in on 25,000, with some months topping $15,000 from the channel.
Tune in to Episode 768 of the Side Hustle Show to learn:
how to apply a "hub and spoke" content model to YouTube SEO
how to pick keywords and topics as a small, low-authority channel
how to turn viewers into affiliate conversions with QR codes and smart calls to action
Full Show Notes: Affiliate Marketing on YouTube: The Path to $15k/mo
New to the Show? Get your personalized money-making playlist here!
Sponsors:
Quo — Streamline and scale your customer communications with Quo (formerly Open Phone). Get 20% off your first 6 months at quo.com/sidehustle.
Shopify — Sign up for a $1 per month trial!
Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!
Monarch — Get an extended 30-day free trial!
About The Side Hustle Show
This is the entrepreneurship podcast you can actually apply!
The award-winning small business show covers the best side hustles and side hustle ideas. We share how to start a business and make money online and offline, including online business, side gigs, freelancing, marketing, sales funnels, investing, and much more.
Join 100,000+ listeners and get legit business ideas and passive income strategies straight to your earbuds. No BS, just actionable tips on how to start and grow your side hustle.
Hosted by Nick Loper of Side Hustle Nation. - What’s the scariest moment you’ve faced as an entrepreneur?
For Halloween, I asked Side Hustle Show listeners to share theirs. You’ll hear about a 1.1 million-follower Instagram account deleted overnight, a Google update that wiped out 60% of one freelancer’s income, a warehouse that miscounted inventory right before the holidays, and 10,000 unusable DVDs.
You’ll also hear from entrepreneurs who chose to be scared: quitting a job, walking away from an eight-figure business, and laying off a team they loved.
I’ll share a few of my own along the way, including a Google ad ban on my first day of full-time self-employment, a ladder crash from my house-painting days, and a Bitcoin ransom email that came from my own address.
Tune in to Episode 767 of the Side Hustle Show to learn:
how platform risk (Meta, Google, logistics partners) can wipe out revenue or an entire following overnight, and what to do when it happens
why owning your audience through email and your own website matters more than ever
how entrepreneurs recovered from lost accounts, blown inventory, costly mistakes, and layoffs — and what they'd do differently
Full Show Notes: Listeners Share Their Scariest Entrepreneurial Moments
New to the Show? Get your personalized money-making playlist here!
Sponsors:
Freshbooks.com – Get 90% off your first 4 months!
Shopify — Sign up for a $1 per month trial!
Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!
Monarch — Get an extended 30-day free trial!
About The Side Hustle Show
This is the entrepreneurship podcast you can actually apply!
The award-winning small business show covers the best side hustles and side hustle ideas. We share how to start a business and make money online and offline, including online business, side gigs, freelancing, marketing, sales funnels, investing, and much more.
Join 100,000+ listeners and get legit business ideas and passive income strategies straight to your earbuds. No BS, just actionable tips on how to start and grow your side hustle.
Hosted by Nick Loper of Side Hustle Nation. - Can you really make money in tickling tomato flowers or selling your own boogers?
Today's episode digs into a pile of genuinely bizarre side hustles pulled from Reddit threads, and most of them actually work.
Alan Donegan from The Rebel School joins the show again to break down a dozen-plus offbeat income ideas, what makes them tick, and how you might replicate the underlying strategy even if you have zero interest in roly-poly bugs or soda can tabs.
Alan's been on the show before, and he and his wife run free business and finance courses that have helped people retire decades early.
He's back today purely for the fun of dissecting strange but real ways people are making extra cash.
Tune in to Episode 766 of the Side Hustle Show to learn:
how niche pet and hobby communities create surprisingly reliable income from "trash" products
why solving an annoyance (standing in line, filling out forms, moving furniture) is worth real money
how strategic partnerships and word of mouth can scale even the weirdest business idea
Full Show Notes: We Found Reddit’s Weirdest Side Hustles
New to the Show? Get your personalized money-making playlist here!
Sponsors:
Freshbooks.com – Get 90% off your first 4 months!
Shopify — Sign up for a $1 per month trial!
Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!
Monarch — Get an extended 30-day free trial!
About The Side Hustle Show
This is the entrepreneurship podcast you can actually apply!
The award-winning small business show covers the best side hustles and side hustle ideas. We share how to start a business and make money online and offline, including online business, side gigs, freelancing, marketing, sales funnels, investing, and much more.
Join 100,000+ listeners and get legit business ideas and passive income strategies straight to your earbuds. No BS, just actionable tips on how to start and grow your side hustle.
Hosted by Nick Loper of Side Hustle Nation. How to Start a Commercial Cleaning Business on the Side: $100k in 9 Months (Greatest Hits)
19/10/2026 | 47 mins.This week’s guest booked $100k worth of commercial cleaning business in her first 9 months.
Haley Gallagher and her husband are serial side hustlers and were specifically looking for a side hustle they could do after hours.
Seeing an opportunity at a bar he was working security for, Haley’s husband asked if they could take on the cleaning contract.
That job snowballed into more jobs and as they hired employees and grew their business, MoonlightCommercialCleaning.com, they earned over $170k in revenue in their full first year.
Tune in to The Side Hustle Show interview to hear:
how Moonlight Commercial Cleaning found their first customers
how they price their work and manage a growing team of cleaners
some of the mistakes they made along the way
Full Show Notes: How to Start a Commercial Cleaning Business on the Side: $100k in 9 Months
New to the Show? Get your personalized money-making playlist here!
Sponsors:
Freshbooks.com – Get 90% off your first 4 months!
Shopify — Sign up for a $1 per month trial!
Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!
Monarch — Get an extended 30-day free trial!
About The Side Hustle Show
This is the entrepreneurship podcast you can actually apply!
The award-winning small business show covers the best side hustles and side hustle ideas. We share how to start a business and make money online and offline, including online business, side gigs, freelancing, marketing, sales funnels, investing, and much more.
Join 100,000+ listeners and get legit business ideas and passive income strategies straight to your earbuds. No BS, just actionable tips on how to start and grow your side hustle.
Hosted by Nick Loper of Side Hustle Nation.- Can one person run an AI consultancy without hiring a team of developers?
Simon Bergeron runs Lemonbrand.io, a one-person business that’s part digital agency, part consultancy, with some micro SaaS on top.
He manages a team of about 500 AI agents doing ongoing work for clients.
Simon tried to pick a niche, but referrals kept pulling him into golf clubs, dentist offices, manufacturers, and accounting firms. The common thread was team size.
Solo operators rarely need outside help, and big companies get bogged down in politics. Teams of 5 to 200 people turned out to be the sweet spot.
His mantra is “measure first, then automate.”
Tune in to Episode 765 of the Side Hustle Show to learn:
how to land your first AI automation client without a tech background
why an "inbox audit" is the most valuable discovery tool for finding automation opportunities
how to structure pricing so clients stay without feeling trapped
Full Show Notes: The $50k/mo One-Person Agency
New to the Show? Get your personalized money-making playlist here!
Sponsors:
Freshbooks.com – Get 90% off your first 4 months!
Shopify — Sign up for a $1 per month trial!
Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!
Monarch — Get an extended 30-day free trial!
About The Side Hustle Show
This is the entrepreneurship podcast you can actually apply!
The award-winning small business show covers the best side hustles and side hustle ideas. We share how to start a business and make money online and offline, including online business, side gigs, freelancing, marketing, sales funnels, investing, and much more.
Join 100,000+ listeners and get legit business ideas and passive income strategies straight to your earbuds. No BS, just actionable tips on how to start and grow your side hustle.
Hosted by Nick Loper of Side Hustle Nation.
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About The Side Hustle Show
The entrepreneurship podcast you can actually apply! The award-winning small business show covers creative ways to make money online and offline, including online business, side gigs, freelancing, marketing, e-commerce, AI tools, investing, and much more. Join 150,000+ listeners and get legit business ideas and passive income strategies straight to your earbuds. No BS, just actionable tips on how to start and grow your side hustle. Hosted by Nick Loper of Side Hustle Nation since 2013.
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