7 Questions to Ask Before You Quit Your Job

Are you ready to hand in your two week’s notice to your boss and peace out?

Not so fast.

Quitting your job to pursue your business full-time is a dream for many side hustlers, but there are a few things you should have in place before you make the leap.

Lifestyle Creep, Luck, and Why Every Podcast Guest Has an Online Course: Q&A w/ Nick

luck and lifestyle creep

In this episode, we’re diving deep into the listener mailbag for a Q&A session.

I’ll tackle things like lifestyle creep, the role of luck, and inadvertently breaking a bunch of links.

And hey, why does it seem like every podcast guest is selling an online course?

Spoiler: there’s some truth to it, and we’ll dig into why that happens.

Best Dad Advice: 10 Life and Business Lessons from Dad

In honor of father’s day, I wanted to share some of the best advice I’ve received from my dad over the years, and how we can all work to apply it in life and in business.

The funny thing is almost all of these were very literal conversations, which I’ve extrapolated out (30 years later!) to have a broader meaning.

The Stadium Model of Entrepreneurship: How to Think Like a Sports Franchise to Unlock More Profit From Your Business

vincent pugliese

What if we looked at our businesses like professional sports teams?

That’s what Vincent Pugliese from Membership Freedom shared, drawing parallels between running a successful business and how sports franchises operate.

Vincent helps people build successful membership sites and communities around topics they care about.

He previously shared his freelance-to-freedom story of going from making $30k a year to earning $30k in a single day through freelancing.

In this episode, Vincent explains the “Stadium Model of Entrepreneurship.” This model draws inspiration from how sports franchises operate, offering various levels of access and products to their audience.

How to Start a Billboard Business: $30k a Month Part-Time

Chris Brown

Even with the rise of digital technology, billboards remain a profitable business.

In fact, Chris Brown built his billboard side hustle to $30,000 a month (part-time!).

Chris now owns approximately 30 billboards around Bentonville, Arkansas, and retired early at the age of 42.

10 Rules to Get Rich and Build Wealth

Robert Farrington

Do you want to get rich? To build real, lasting wealth that can change your family’s circumstances for generations?

Prepare to be disappointed because there are no get-rich-quick shortcuts or overnight secrets.

Building wealth takes time, discipline, and sustained effort.

But the good news is you can absolutely do it, no matter your current situation or starting point. All it takes is following some proven rules and principles to put you on the path.

I’m talking about 10 fundamental rules that will help turn your financial dreams into reality. And they come from my recent conversation with Robert Farrington, founder of the famous personal finance site The College Investor and a longtime guest on The Side Hustle Show.

This conversation is based on his article 10 Rules to Get Rich and Grow Wealth.

How to Start a Vending Machine Business: $500+/mo Per Machine

how to start a vending machine business

Tired of trading time for money at your 9 to 5 job? Looking for a way to make passive income with minimal startup costs and overhead?

Then starting a vending machine business may be perfect for you.

The vending machine industry was valued at $42 billion last year and is expected to grow at 8.1% from 2024 to 2030.

Profitable vending machines are everywhere — offices, apartment buildings, gyms, airports.

Wherever people gather, there’s an opportunity to provide convenient access to snacks, drinks, and other bestselling impulse-buy items.

And it’s a great market to get into because it’s extremely fragmented, with vast potential for growth. No national player owns more than 5% market share.

Side Hustle Stacking: How One Extra Income Stream Can Lead to More

Bjork Ostrom Image

How can one income stream turn into a whole lot more?

Simplify first, diversify second—that’s an idea I have always advocated on the show.

The first step towards diversifying is to have something working. But how do you know it’s time to diversify?

That is exactly what Bjork Ostrom (our previous guest from Ep 46) has done as he (and his wife Lindsay) masterfully “stacked” multiple online businesses that have developed out of their original food blog, Pinch of Yum.

This 10-year-old blog has been a launchpad for Food Blogger Pro (a guide for aspiring food bloggers), Clariti (for optimizing your site’s content), and the holding company, TinyBit.

And this is the framework he uses to decide if an idea is worth pursuing.

How to Start an Ice Vending Business: $2500/mo in (Almost) Passive Profits

steve slagle

Making extra money on the side often requires finding ways to create leverage.

Leverage means getting paid multiple times for work you only have to do once, and making money without having to actively do the work yourself.

One side hustler who has cracked the code on leveraged profits is Steve Slagle. By day, Steve works construction jobs. But outside of his 9 to 5, he now earns over $2500 a month from Beachside Ice, his ice vending machine business.

In this episode, Steve takes us through the world of vending machine location negotiations, landowner compensation, and the importance of maintaining positive relations. We explore the finer details of partnering with manufacturers, securing permits, and overseeing installation and delivery.

Usually Hustling, Occasionally Social

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