Side Hustle School

A caller is wondering about becoming a Medical Billing Advocate. This is someone who helps patients negotiate and lower their medical bills, especially in cases where the bill is high and might include mistakes or unnecessary charges. 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...

In this week’s Failure Friday segment, we hear from someone who started a coupon directory website. Unfortunately, he ended up spending more money than he saved. 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....

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Bay Area beekeeper who slings honey to the tune of $40,000/year part-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...

I love hearing side hustle ideas from listeners! Today’s features a woman with a background in retail who wants to become a vintage shopping concierge. Is this idea feasible, profitable, and timely? 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 list...

Today’s listener poses a challenge: is it possible to set up a Shopify store in just an hour? The platform provides a lot of different features and options, which is great but can be time-consuming to sort through. 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...

In this week’s First $1,000 segment, we hear from a longtime candle lover who starts her own brand. After a few months, she reaches a flaming milestone and is lit with excitement.  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 sever...

Today’s listener has achieved a milestone: they have 3,000 people on their list! That’s great, but because email list providers charge based on subscriber numbers, the monthly subscription cost keeps going up as well. Can anything be done about this?  Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This...

Platforms like Kalshi and Polymarket offer the ability to bet on political events, including presidential elections and cabinet appointments. What are some tips for coming out ahead? 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 sev...

In this week’s Failure Friday segment, we hear from a travel agent who’s excited to take flight—until a trip she books for ten clients is unexpectedly canceled. 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. S...

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a seller of adult toys and other items for sexual wellness. She now earns $3,500/month in affiliate commissions! 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 listener wants to open an online store selling floppy disks and cassette tapes. He thinks there’s a renaissance for these items. Is he right—and if so, what steps should he take? 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 sever...

Recently we’ve looked at why there are so many subscriptions. Today’s caller wonders: what are some good physical products (i.e. non-digital) to sell in subscription form? 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 e...

In this week’s First $1,000 segment, we hear from a serial side hustler who builds an ADU in his backyard, allowing him to earn $1,500/month in passive rentals. He then uses the profits to buy another property. 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 less...

All you want to do is run your side hustle, take in orders, maybe grow your business, not just fix things that are broken—but these days, websites often get hacked or just go down for no good reason. Can anything be done? 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...

Today’s caller is from Pakistan, and he wants to operate a remote personal training side hustle. He’s qualified for this role and thinks it could be helpful—but he’s also wise enough to foresee a couple of challenges.  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...

In this week’s Failure Friday segment, we hear from an aspiring bunny reader. After being inspired by a woman who breeds rabbits to pay for college, she attempts to start her own breeding farm. Unfortunately, it turns out she’s living on burrowed time.  Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Th...

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a pottery maker who sells her dishes and bowls using Fulfillment by Amazon. That service is usually for mass-manufactured items, so her product is a bit different.  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,...

In this episode, a caller wonders about opportunities for retirees. Are some side hustles inherently better for someone in that situation? Let’s talk it out! 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...

A listener is wondering about AI, specifically ChatGPT, an incredible tool that’s been all over the news lately, and how it applies for side hustling. Can you outsource your tasks to these tools? Can you put them to work? Can you make something using AI and sell it?  Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting...

In this week’s First $1,000 segment, we hear from a wedding planner who specializes in budget ceremonies while still getting paid for her important work.  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 no...

Let’s have some real talk today: a side hustling caller is having a problem with her side hustle: her partner doesn’t like 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...

One of our callers has noticed that lots of stuff for sale ends in the number 9. Is this some scientifically proven marketing principle, or is it entirely random? You might be surprised by the answer! 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...

In this week’s Failure Friday segment, we hear from the aspirational owner of a scavenger hunt side hustle. On a big day for a major client, everything goes wrong. 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...

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a career advisor who sells resume (CV) templates and coaching. The business now brings in at least $4,000/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...

If you don’t like selling, or just talking to people all the time—I’m in that club!—what do you do? 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....