10 Big Ideas from 500 Episodes of The Side Hustle Show

This week it’s the 500th episode of The Side Hustle Show, which just seems crazy to me.

It feels like just yesterday I started this thing in a lot of ways. But it’s been 9 years — I guess time flies when you’re having fun!

In honor of the 500 episode milestone, I wanted to reflect back on 10 big ideas and 10 common themes over the last 9 years.

It took longer than I care to admit to go back through the archives and pull out some of these forgotten soundbites, but I think you’ll like ‘em.

Tune in to this episode of The Side Hustle Show to hear 10 of the big ideas I’ve gotten from speaking with hundreds of guests of the years, and how you can implement these ideas within your business today.

1. Set the Vision (and WHY it’s Important to You)

Where do you want to go?

Why do you want to get there?

And who do you want to take along for the ride?

Without that driving motivation, it’s going to be too easy to quit.

It’s the same reason people give up on their New Year’s resolutions — they didn’t want it bad enough, or it wasn’t that important to them.

Otherwise, by definition, they would have made it happen.

I was never much into vision boards or affirmations or anything like that, but a couple of people challenged me in 2018 to actually sit down and write out a 3-5 year vision of what life would look like.

One of them was Brian Scudamore from episode 332, the founder, and CEO of 1-800-GOT-Junk. Brain told me his number one tip for anyone who wanted to improve their life or business was to:

“Come up with your vision, ‘what is your painted picture?’ I call it.

Now, I sat down on a dock, at my parent’s summer cottage when I was at a million in revenue, and I wrote down on paper, one page, double-sided, our painted picture, which said we’d be in the top 30 metros in North America, we’d be the FedEx of junk removal, we’d be on The Oprah Winfrey Show… all these things and more happened because we had a destination, a clear vision of what that future would look like.

So for anyone in life, I think it’s what’s your painted picture? What does your life look like in three to five years and write it down?”

At that time, his business was doing about a million dollars in sales a day.

Maybe there’s some survivorship bias, but when an entrepreneur at that level gives that advice as a “#1 Tip,” I think you’ve got to take notice.

2. Piggyback on Trends

The next big idea is one I call the “Piggyback Principal.”

This was explained by Toni Anderson in episode 194:

“Find a hot trend and piggyback on that hot trend. That would be my best advice for anyone starting out.

Instead of just going for that item, sell an accessory or an add-on to the really popular item.”

When you’re trying to come up with a side hustle idea, we’ve seen some great success stories of people catching a rising tide.

In a sense, this is the old business model of selling shovels into a gold rush.

For example, more and more people are hiring cleaning services.

More and more people are starting podcasts.

More and more companies are getting involved in content marketing.

• Maybe you could offer a freelance writing service like Georgia Austin.

More and more parents are homeschooling.

More and more people are using [fill-in-the-blank] software.

• Maybe you could create some video training materials like Paul Minors or become a consultant like Brad Rice.

These are just a few of the many examples I’ve seen on the show.

Catch a rising tide, piggyback on those trends, and you’ll have an easier time than fighting against the current.

Be on the lookout for new trends in your industry because there’s an advantage in being early as well.

3. Solve Problems

The vast majority of guests you hear on the side hustle show built a business to solve a specific problem.

That’s what customers pay money for!

They don’t particularly care about your passions and motivations, as long as you can make their pain go away.

John Lee Dumas explained it this way:

“’Follow your passion’ … that’s terrible advice.

If it’s just your passion, and there’s no value to go with it, it’s just a hobby. But unless it’s providing real value to their world, unless it’s providing a real solution to their problems, they’re not going to care that much.”

The good news is humans are natural born problem solvers.

So, how do you find problems to solve?

• Conversations – You can ask questions like, “what challenges are you facing right now?” Or, “what are the biggest threats to your business?”
• Your own pain points – Where do you spend your own money? What do you buy that you wish there was a better option?
• What other people complain to you about – If other people are complaining to you about something, there might be a business opportunity there.

4. Just Start (and Stay Started)

This is the most common #1 tip from guests on the show.

Pat Flynn from the Smart Passive Income podcast shared one of his favorite productivity tips:

“One of my favorite productivity hacks involves just a little note on my computer that says one single word — and that word is “start”.

An object at rest tends to stay at rest. I often just procrastinate. So I tell myself through this note, just a Post-It note on my computer, very simple, to just start.”

The frustrating part, is what’s often left unsaid: Just start … yeah, but what?

The truth is, it doesn’t really matter.

Julie Sheranosher from episode 123 likened just starting to playing chess and added:

“It doesn’t really matter what your very first move is going to be if you’re the first player starting a match in chess. Because whatever it is, you’re just trying to drive a response from your opponent.

And this is what we’re trying to do. We’re trying to get some sort of feedback from the universe, from your clients, from your customers, from the people around you, from the readers of your blog, listeners of your podcast, we’re trying to feel what is the right thing to do.”

What’s interesting about the last 9 years of interviews is we’ve seen a lot of entrepreneurs where the business they’re running today isn’t the business idea they necessarily started with.

I started selling paint jobs by going door to door. I never would have expected it would lead to this!

Ryan Finlay described the phenomenon this way, way back in episode 72:

“Some of the best opportunities that you’re going to find in business are going to be found once you’ve already started moving in a direction. Very infrequently do you see incredible opportunities before you even start.”

5. Go Where the Cash is Already Flowing / Go Where Your Audience Is …

Georgia Austin decided to set up her writing gig on Fiverr — a big marketplace where people were already buying that service:

“I wasn’t necessarily thinking anything would come of this Fiverr account. But I made it and I uploaded my first gig — it was a website content gig. And, to my surprise, I got my first order within two days.”

Similarly, you can take a look at existing listings on online marketplaces to see what’s working.

Here’s Rachel Jones from episode 449 on doing initial product research on Etsy:

“Success leaves clues. So my biggest recommendation is to go on Etsy and just explore. I mean, you can go as simple as just type in the word printables, or digital download, and see what pops up.”

In just about every niche, there’s a marketplace to set up shop and put your product or service up for sale.

This was such a big idea, I wrote a whole book about it in 2016 called Buy Buttons.

6. Fast Track with Partnerships

This is a super common marketing theme throughout the archives, even going back to 2013-2014.

We had Ryan Cote in episode 34 talking about the value of strategic referral partnerships.

The gist of this is thinking about who your target customers are already doing business with, and then building relationships with those people as a fast-track way to potentially connect with their customers.

And it can be online or offline. For example, here’s one way Erica Krupin marketed her pooper scooper business:

“I did something really creative. I went to Dunkin Donuts, and I broke them up into half a dozen each.

I walked into local vet offices and pet supply places. And I said, Hi, my name is Erica. Blah, blah, blah, blah. I have donuts and business cards. May I leave both of them here?”

Could you go speak at a conference?

Could you guest on a podcast?

Some of my biggest spikes on the download chart have come immediately following a guest appearance on other relevant shows like Entrepreneurs on Fire, Bigger Pockets Money, Mad Fientist, and ChooseFI.

Could you display at an event?

Any of these types of partnerships that allow you to tap into someone else’s audience are super powerful.

I encourage you to brainstorm a list of your top 10 or 20, even 100 potential dream partners. Then ask yourself, “how could you be of service to them in some way?”

We did a full episode on this recently with Dustin Lien, on hosting partner workshops.

Dustin would put on a free educational workshop, showcase his expertise (great for consultants and freelancers), and in exchange, all the partner has to do is invite their audience.

“When you’re filling out that Dream 100 list of who to partner with, think about who has your exact same target audience, but is not a competitor.”

7. Build Your Email List (Algorithm-Proof Your Business)

Building your email list doesn’t happen by accident, but it doesn’t need to be overly complicated either.

The basic formula is to offer some sort of lead magnet — something of value — in exchange for your visitor’s email. It could be a:

• cheat sheet
• template
• resource
• guide
• checklist
• free mini-course

Here’s how Jennifer Maker broke it down, who when we spoke, had a list of something like 380,000 subscribers.

“My big goal and everything I do is to get people onto my mailing list. I don’t put a lot of faith in social media. 

So every blog post that I put out, is typically a how-to, if it’s not, it’s something very similar. And I funnel them to my lead magnet, and my lead magnets are very high quality.”

Another popular strategy is the quiz funnel, where you ask visitors to answer a handful of questions in exchange for personalized recommendations.

This can be used very effectively in e-commerce, as we heard from Connor Meakin recently, and in content businesses as well.

Here’s how Tori Dunlap drives email sign-ups from TikTok:

“The caption was, “If you want to personalize resources, take the free quiz in my bio”.

So I had created, along with my team, a system where if you come to my website, you can take this free quiz that asks you questions about your financial experience.

And, in exchange for your email, you get these results, you get this list of personalized resources.”

Build that list as a way to weather the storm, as a way to directly communicate with your target audience without relying on some big tech algorithm to show them your stuff.

Building a similar quiz funnel is definitely something that’s on my project list for this year.

This is one of the most important metrics for me, and if you’re not subscribed, come on in, the water’s warm! Sidehustlenation.com/join is an easy way to do it.

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8. Do What Matters, Consistently

If email is an important metric in your business, it makes sense to focus on that.

One common trait you might have noticed from Side Hustle Show guests is this practice of focusing on what matters.

As a business owner, and especially as a side hustler, you’ll face distractions all day long. But there are probably only a few core things that really matter and move your business forward.

Rosemarie Groner explained it this way, in Episode 268:

“You don’t have to work 50, 60, 70 hours a week if you spend your time doing the things that make you the most amount of money consistently.

If you eliminate doing the things that make you less amount of money consistently, your income naturally grows — like it’s almost impossible to fail at this.

I eliminated anything that wasn’t the most important thing for my growth. So, I didn’t answer all of those spammy emails that you get there that are like, ‘Hey, can you put this infographic in your blog posts?’

Like, no, I didn’t even read them. I didn’t answer every blog comment, which is something that pretty much everyone tells you to do. I didn’t do all the things that everybody else said was important.”

For me, this practice has a few parts:

First, I try and do a daily check-in as part of my nightly shutdown routine. I ask myself what I got done that day, and compare that to the list that I said were my top priorities.

If they match up, great. If they don’t, why not and what happened?

The next phase in this review process for me are my quarterly progress reports.

This is a chance to publicly reflect on what I worked on and the results of those projects. It’s a great excuse to review a few times a year, what’s working in your business and what’s not.

Other people will call these “after-action” reports, or monthly or quarterly reviews. But the idea is the same, stop for a second to ask yourself if the hours you’re putting in are making any meaningful impact.

Because if they’re not, that’s when it’s time to adjust course before you get in any deeper.

And finally, I run what I call “revenue attribution” reports once or twice a year.

This is just a high-level analysis of what’s driving sales. That way, I can hopefully pour more fuel on the fire for the channels that are working, and maybe cut back your hours on the projects that aren’t as lucrative.

If you can do the important things consistently, and move to eliminate, automate or delegate everything else, you’re going to start feeling this sense of positive momentum and progress.

So that’s Big Idea #8, this habit of reflection, analysis, and focus — doubling down on what’s working, or adjusting course as needed.

There’s this compound effect of aiming to get a little bit better every day.

9. Accept Mentorship and Education

The idea of mentors and coaches and masterminds and paying for courses was all pretty foreign to me 9 years ago, but I’ve benefited tremendously from all of the above since then.

I definitely had this sense of perhaps ill-placed self-confidence in that I could figure everything out on my own.

Maybe I could have, given an unlimited time horizon.

But there’s certainly some value in short-cutting the learning curve by paying attention to other people in the space. As well as paying for coaching, building your own mastermind group of people working toward similar goals can help you take action and move forward.

Having now been a part of several mastermind groups over the last 9 years, it’s hard to imagine going at it without them.

Not just having some sort of peer accountability, but more than that. The camaraderie and honest feedback and the glimpse into other online businesses.

It’s super helpful to have a group of other business owners to bounce ideas off and help each other work through challenges.

If you’re currently going at it alone, I would prioritize creating some sort of mastermind or accountability group.

It’s an overused quote, but there’s some truth to being “the average of the 5 people you spend the most time with.” So surround yourself with people on the same path.

Just a few weeks ago, Joan Ferrell from episode 492 left us with this, that hit home for me:

“No matter what you choose to do, you should educate yourself. Even if you know some about it, the best thing to do is to take a course, go onto YouTube, do your research before you start it, which is what we did. Education is cheap compared to ignorance.”

It’s the same reason why reading books has a tremendous ROI — it’s the ability to download someone else’s experience and skills and apply it to your situation.

It doesn’t have to cost a lot of money, but mentorship and investing in your own entrepreneurial education is definitely a common theme from Side Hustle Show guests.

Again, it probably sounds like common sense but it wasn’t something that was really on my radar when I started the show.

10. Level Up

Big Idea #10 is to Level Up by creating systems, and becoming the business owner more than the business “doer.”

Tyler Gillespie dropped this challenge / thought exercise on us in episode 430, what he called “The laptop test.”

“If you closed your laptop today, how long would your business survive?

That’s really important because if someone’s gonna buy your business, it’s a huge tell, how dependent the business is on you.”

This is something I’ve done OK with in certain areas, but have completely failed in others.

One exercise I’ve used in the past is to create a detailed time audit. You can download my time tracking template here:

You can’t manage what you don’t measure, so you need to measure what you’re actually spending your time on.

Do that for a week or two and you’ll start to see some patterns of tasks that you can hopefully:

• eliminate (if they’re really not that important)
• automate (create some sort of recurring system or process)
• delegate — could you write the recipe and have someone else on your team follow it?

When’s it time for a system?

Jeff DiOrio from EliteChess.net and episode 487 said something that really resonated with me:

“As soon as I got something unmanageable to where I’m staying up all night doing something, that’s when I generally think, okay, I need to get a system.”

To get to the next level and pursue some of the other fun projects and experiments I’d like to, I need to scale back my involvement in certain day-to-day operational tasks.

So, this type of Laptop Test and systemization is a high priority for me this quarter. It’s one of the Big Ideas from 9 years on the show — to consistently level up you have to be working ON your business rather than IN it.

Your Turn

Have there been any moments or ideas or themes that have stood out to you over the last 500 episodes? Let me know in the comments below!

Thanks so much for tuning in!

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