14 Big Ideas From the Last Year of Side Hustle Show Guests


A side hustle is not only an opportunity to earn extra money but also a key to escaping the 9-to-5 grind.

But launching a side hustle is not easy — just ask the many amazing guests who’ve been on the show!

More often than not, solopreneurs’ business trajectories are a series of trials, errors, pivots, and adjustments.

These are things we can all learn from, which is why we rounded up 14 big ideas from Side Hustle Show guests that really stood out this year.

Whether you’re thinking of starting a side hustle or looking to breathe new life into an existing one, these ideas may just be what you need to give your business the best chance of success.

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1. Test Different Opt-Ins

This first big idea comes from Connor Meakin of BluebirdProvisions.co, an organic bone broth and bone broth powder company.

Once he started selling his own line of bone broth products in the US, Connor said he put more effort into engaging with his email list.

But his list was small, and the opt-ins he embedded into his blog posts didn’t help much. What did help, though, was testing different opt-ins to see what stuck.

Connor quickly found that quizzes worked really well. For Connor, quizzes were a creative way to get email addresses.

“Everyone loves to take a quiz. Everyone loves to get their results and see their custom plan or … custom product recommendations.”

Connor also uses an opt-in giveaway to give people a reason to sign up for his email list. “Evidently, people like free stuff.”

2. Optimize Your Funnel

This next big idea comes from Nathan Barry, the founder and CEO of ConvertKit and the author of “The Ladders of Wealth Creation.”

Nathan wanted to sell more books and courses, so he grappled with the question of how he can get better top-of-the-funnel conversions.

Ultimately, what he did was look at where people were dropping off from the ConvertKit sales funnel. He found that there were a ton of people coming in at the top of the funnel but that many of those people were dropping off from the funnel after the first 30 days.

He addressed that issue by switching the default on his website’s pricing page from a monthly plan to an annual one.

With that small tweak, Nathan went from just 4% of customers signing up for an annual plan to 14%. That’s a 250% increase!


3. Update Old Content

Making new content is one thing, but keeping it updated is another.

SEO-savvy bloggers and marketers know the importance of investing time to make sure content is up-to-date, whether that means making minor changes to an article or republishing it completely.

Robert Farrington from TheCollegeInvestor.com (which has a massive library of content) had a lot to say about updating content in episode 482.

This is what his updating and republishing process looks like.

  1. Keep a running list of blog posts for the year.
  2. Get on companies’ mailing lists to keep tabs on product updates or launches.
  3. Do a content audit of the top 100 posts for the year.
  4. Do a thorough manual check to make sure the posts are current.

Robert updates his content every year using Asana, a project management platform built to help remote and distributed teams organize, track, and manage their work.

4. “Pick Two”

Robert also has another helpful piece of advice for anyone who’s building a brand or a business online: pick one platform in addition to your website and focus there.

If you like podcasting, for example, then hop onto the recording booth and make an episode. If you like videos, build a killer YouTube or TikTok content strategy.

The point is to complement your website with a second platform that’s not in your wheelhouse, and try to grow that.

“A lot of people are looking for the answer to their problems, the solution, the insight, the understanding of something,” Robert said. “And that’s really what you should be focused on creating.”

5. Follow the Demand

This next one from Georgia Austin from WizardOfContent.com might not be so much an idea as it is a word of advice, but it’s relevant all the same.

Georgia is a freelance writer on Fiverr who did over $500k worth of work through the platform in 2021 despite the tough competition.

What helped her land gigs was following the demand.

“When you get too many orders or too many inquiries, don’t say that you’re too booked up,” Georgia said. “This is your opportunity to grow your business.”

In the context of content marketing, “following the demand” is creating helpful content that answers people’s questions and trying to create better resources than what’s already out there.

If you’re a podcaster, “following the demand” is going where your target listeners are. That could look like finding some podcasts in your space to be a guest on, experimenting with paid ads, or setting up cross-promotions with other similar podcasts.

6. Take Messy Action

Big idea number five comes from Kat Norton aka Miss Excel, who has reached hundreds of thousands of followers as a spreadsheet influencer.

Kat, who now enjoys consistent 6-figure months and even the occasional 6-figure day, started on TikTok in June 2020 and now has over 700k followers on the platform. She also has over 550k followers on Instagram, where she’s had a number of posts go viral.

Kat attributes her rapid follower growth on both platforms to messy action. “I do not wait for things to be perfect. I do not wait for the right time.”

If you get an idea, run with it. Figure out how to get it done. After all, you can always refine it along the way.

7. Use Your Superpower

In episode 511, Matt Ruttenberg shared a word of advice to people looking for a side hustle: use your superpower!

Are you analytical? Do you enjoy talking to and connecting with people? Whatever it is, find something that comes easier to you than the average person and lean into it.

“That’ll help you be as successful as you can be,” Matt said.

What’s your superpower?

8. Get a System

This next big idea is from Jeff DiOrio from EliteChess.net, and his idea is to get a system.

Jeff, a chess player, coach, and a full-time dean at Naperville North High School, said the idea came to him after pulling all-nighters trying to juggle his side hustle and dean duties.

Jeff’s epiphany shows that there will always be plenty of areas of opportunity to continue systemizing, especially if you want to grow your side hustle while keeping your full-time job.

In practice, getting a system is all about prioritization and delegation. What are your priorities? What tasks can you delegate so you have more time to focus on growing your side hustle?

If you’re coming to dread certain aspects of your side hustle or if you find yourself doing the same thing every week, consider putting systems in place to help manage your business more efficiently and set it up for greater success.

9. Do One Thing a Day to Get Closer to Your Goal

Determination spells the difference between success and failure, something that Brien Gearin of RicochetDM.com can attest to.

In episode 496, Brien shared the one thing that kept him going through 11 months of not getting a single client: do one thing a day to get closer to your goal.

There will always be more emails to read, to-do lists to check off, and projects to tackle than hours in a day.

It’s simply not realistic to do everything.

So even if your to-do list grows and your unread emails pile up, what’s important is to be consistent about making progress on what matters to you.

And it doesn’t have to be related to work at all. The thing that may help you get closer to your goal can be as simple as hanging out with your kids, visiting friends, or going hiking.

So what’s the one thing you can do today to keep moving the ball forward?

10. Ask for What You Want

Another big idea that stood out this year comes from Shannon Houchin, who has been flipping peaches for 10 years.

Shannon now has over 100 roadside stands, and it’s all because she wasn’t afraid to ask for what she wants.


“If it suits your business goals and it suits your personal desires, ask for it,” Shannon said.

In the world of solopreneurs and freelancers, there’s always talk about charging what you’re worth or raising your rates.

It’s understandably an uncomfortable topic as many people try to balance the value they bring with some level of gratitude over getting paid.

But almost everything in the world is negotiable, and Shannon’s big idea is a reminder of that.

The reality is, if you don’t ask for what you want, you just end up being an order taker. So don’t be afraid to negotiate better deals for yourself.

The key is to consider what’s in it for the other party, illustrate the unique value you bring to the table, and make your proposal.

11. “Scared Money Don’t Make Money”

Another great soundbite this year came from Cat Bloch in episode 471.

Cat runs MDRN Photobooth Co., which operates 20 photo booths in multiple cities all across Canada.

Cat jumped into her business with about $16,000 USD, which is more than many side hustlers spend to kickstart their businesses.

But it didn’t unnerve her. “Scared money don’t make money,” Cat said.

As Cat explained, she’s very good at seeing when there is an advantage to spending money, so she felt confident to make that investment.

But you don’t have to spend as much money as Cat to put her adage in practice.

Spending money to your advantage is making home office upgrades with a new sit/stand desk or a bigger monitor. It’s investing in a high-quality microphone to record your podcast episodes with. It’s paying for training to learn a new skill — and so much more!

12. Be Consistent

One of the common themes of the episodes this year is consistency — something Varnie Sambola of MV PALLET SOLUTIONS is very familiar with.

Varnie plays matchmaker between pallet buyers and sellers to flip pallets for profit.

Since starting his pallet flipping business in 2020, Varnie has already scaled it to $1,000 a day.

He credits John Wilker’s Simplest Biz course with helping him get started. As to what kept him going, though, that’s thanks to consistency.

“Human beings have habits,” Varnie explained. “So if you can do your work consistently, it becomes a habit.”

And once it becomes a habit, work feels less like work.

13. Iterate

But how do you balance consistency and persistence if you’re not seeing results or not seeing the results you want fast enough?

The answer may lie in big idea number 13 from Gill Tietz of the Sober Powered Podcast.

“My number one tip is iterate,” Gill said.

If something isn’t working in the way you want, don’t blame the algorithm.

And if it’s clearly not working, stop doing it. As Albert Einstein purportedly said: Insanity is doing the same thing over and over again and expecting different results.

Instead, make some changes or try something completely new, then see how that performs before iterating again.

14. Find a Coach or Mentor

Last but not the least, big idea number 14 comes from multiple guests, including Jennifer Sobel, Chris Lollini, and Justin Tan just last week.

But Ryan Levesque of The Ask Method Company put it succinctly in episode 508 when he said: Find a coach or mentor and strive to become their number one student.

Ryan said that is the one move that he does over and over again whenever there is an area of his life that he wants to improve.

Entrepreneur and motivational speaker Jim Rohn said that we are the average of the five people we spend the most time with, so it’s important to make sure we’re surrounding ourselves with a supportive network that’s on a similar journey.

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