Side Hustle School

Let’s talk about two of my favorite things in the world: cats and cat videos. A listener wonders if there’s any way to monetize them. How do all those cats get paid??  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...

In this week’s First $1,000 segment, we hear from a coder with an unusual side hustle: he helps clients recover their hacked or lost Facebook accounts. In his first month, he’s already served fifteen people! 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...

A caller from Ireland wants to start his own instructional workshop. How are live events different from other services—and what are some tips for running one well?  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 wee...

Today we’re going to hear from a CPA in the midwest who wants to focus on retaining clients. This is more important than finding new ones! 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...

In this week’s Failure Friday segment, we hear from the founder of an advisory service who hires his first assistant. The relationship starts well, but as the founder stops paying attention, things go downhill. Dun dun dun…. 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 fr...

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder and CEO of a lead generation / digital marketing company called Credo. It’s been through a few different iterations over the years, but continues to grow and evolve. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job...

Today’s caller wants to drive for Uber Eats, Door Dash, and Postmates—but it’s not what you think. He’s not looking for a new part-time job; he just wants to collect the bonuses that each service offers, then quit.  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 one of the early stories for the podcast that was also included in the Side Hustle book, a guy earned $10,000 in a short amount of time by doing voiceover work commissioned through Fiverr. Is this still possible now? 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 gu...

In this week’s First $1,000 segment, we hear from a web designer who wants to get off the freelance train by creating a standardized service. Her new “website audit” offer is working! 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 se...

Today’s caller has a retail business that is not typically dependent on holiday sales, but he wants to juice the numbers a bit. How can you increase end-of-year sales in a non-holiday 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...

A number of apps, websites, and platforms promise that you can earn a few hundred dollars a month in exchange for your opinion. Is this legit? 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: SideHus...

In this week’s Failure Friday segment, we hear from a maple syrup reseller (this is a thing) whose inventory was stolen by a Canadian cartel (this is not a joke). How does he handle this sticky crisis?? 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...

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Florida enthusiast who becomes America’s leading ambassador of kickbikes, a European mode of transport and adventure. 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...

Today’s listener is an aspiring political lobbyist—but this isn’t Job School, it’s Side Hustle School! Can she do part-time lobbying for passive income as a business instead of a career?  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&...

If you’re not trying to be Jeff Bezos selling Christmas trees (his original business), you still might want a business that only operates one part of the year. In that situation, when is the best time to start ramping up?  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...

In this week’s First $1,000 segment, we hear from a handyman who builds his part-time business to $4,000/month on TaskRabbit, and then goes off-app to avoid platform fees. 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...

Our listener is earning more than $50,000/year from three side projects. Whoo hoo! Still, he wants more of this income to be passive, because he’s doing a lot of work for it. How can he go to the next level?  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 lesson...

A listener has a question about self-sabotage: whenever they find themselves moving forward, they end up backing away. What can be done in this situation?  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 n...

In this week’s Failure Friday segment, we hear from a listener who borrowed money from a friend for an investment in a cryptocurrency project. Need we say more? 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 special episode recorded in South Africa, Chris reflects on 5+ years of Side Hustle School and encourages listeners to eat more pie. 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: SideHustl...

If you’re familiar with any of the major streaming platforms, you might be aware that there are cover versions of lots of popular songs. How does this work in the business sense? 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...

Today’s caller has an idea to start her own app for people who identify as asexual (where you don’t feel much sexual attraction to anyone). What’s the best path forward?  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...

In this week’s First $1,000 segment, we hear from a Texas event planner who earns at least $2,000/month on the side. One early event featured a creative display of hundreds of bananas. 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 s...

Today’s listener wonders: how can the average person capitalize on the fact that so many people are much more comfortable with video calls these days? 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:...

An athletic listener from Minnesota seeks advice on starting a fundraising campaign. Will he need to improve his social media for more people to notice? 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...