10 Creative Side Hustles That Make Real Money – Part 2

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This week’s show is a re-take on last year’s Thanksgiving episode on 10 Creative Side Hustles that Make Real Money.

That show was a hit, so I’m returning to that format for another round.

Some of these will you have kicking yourself not thinking of it yourself, and some of these are 6-figure businesses you could literally start tomorrow.

Here are the 10 creative side hustles I cover in this episode.

1. The 7-Figure Lemonade Stand

This first business is one you might already have experience with.

Josh Lange runs Just Squeezed Juice, a seasonal 7-figure (seriously!) lemonade business he started as a side hustle at 22 years old. It’s not just a business idea for kids!

Josh explained how he got started to Chris Reynolds on The Business Method Podcast. He was working as a bartender at the time when he came up with the idea to be his own bartender, with his own bar selling fresh lemonade.

lemonade stand

“In a way, I was creating my own job at the time,” he explained. Josh made a little bar with a fresh squeezer and shot glasses and took up a spot in the art district area in downtown Santa Fe.

A couple of weeks in, one of his customers – who happened to be in charge of booking vendors for festivals – asked if Josh would like to sell lemonade at a festival. Josh happily agreed and made more than $3k that weekend.

He’s since sold lemonade at Woodstock, Bonnaroo, Coachella, Bottle Rock and tons of other events and festivals. Josh has taken his side hustle from $100 a day to selling over 6-figures of lemonade in a single day and growing an enduring business and brand.

Josh raised an interesting point to explain one of the reasons why his business has been successful. “Most businesses are operating off of people coming to them, and we go to the people,” Josh told Chris.

My Take

This is the essence of my “Buy Buttons” theory — go where the cash is already flowing!

Where can you find your people? I loved Josh’s story because it’s an example of a simple business, executed well.

You don’t need a terribly innovative idea; you just need to do something well and find customers.

2. The World’s Most Boring Podcast

Podcasts can be lucrative side hustles, but it’s the creative approach that Drew Ackerman took that makes his story interesting. His podcast is so intentionally boring, its goal is to put you to sleep.

Drew is the voice behind the Sleep With Me Podcast, which has with more than 800 hour-long episodes, almost 10,000 reviews on Apple Podcasts, and over 5,000 monthly patrons on Patreon.

Drew describes his show as helping “grown-ups fall to sleep, a little bit like a goofy friend telling you a bedtime story.”

It wasn’t an overnight success. It took 3 years of constantly putting out the show, making it better, and figuring out the model that worked before Drew started to earn a decent income.

Drew would set himself “quit dates” for some points in the future where he would ask himself if he should carry on with the show. The numbers were always showing he was reaching and helping people, so he carried on.

In 2017, Drew started cutting his hours at his day job and focusing more on his podcast. Now he’s working full-time on his business, his show is sustainable, and he’s been able to put aside an emergency fund.

(Thanks to Mike McAllen for the intro to Drew!)

Related: How Much Does it Cost to Start a Podcast? Less Than You Might Think!

3. Local Dog Poop Pick-Up

Could you really make $100 an hour picking up dog poop?

A listener — who asked to remain anonymous — shared this low startup cost side hustle with me.

After picking up after his own dog, he wondered if anyone else would pay for the service. He went to Google and sure enough, he found other dog poop pick up businesses were already out there.

Undeterred by the competition, he began joining various local Facebook groups and advertising his service.

In just a few months, he’d attracted 25 customers, and has most of them set up on weekly retainer deals for $20-35 a week, depending on the size of the yard and how many dogs they have.

He knocks out all of these yards in about 6 hours, including drive time, one day a week, netting around $600 for his work — or $100 an hour for picking up dog poop.

According to the American Pet Products Association, pet owners are on track to spend more than $6 billion this year on grooming, walking, sitting and related services. So, if the poop pick-up business doesn’t appeal to you, there’s still plenty of opportunity in the pet industry, which leads me to…

4. The 6-Figure Dog Walking Business

In the mid-1990s, Kristin Morrison started Woof! Pet Sitting Service.

She told Marketwatch.com, “I loved to walk, and I love animals. … To be able to combine the two was mind-blowing to me.”

By the early 2000s, she was making 6-figures a year walking dogs, but burning herself out in the process. She was working 7 days a week, often up to 12 hours a day.

That’s when she made the shift from dog walker to owner of a dog walking company — that’s subtle, but really important. She stopped walking dogs herself and instead hired people to do that.

This freed up time for Kristin to focus on growth tasks like marketing and hiring. “I thought, ‘My business is growing, I need to grow, too. I need to be the captain of the ship, on deck, instead of being in the belly of the ship,’” Kristin was able to expand the business, all while cutting back her working hours.

After selling her company in 2013 for an undisclosed sum, Kristin now helps people start their own pet-centered businesses at Six-Figure Pet Business Academy.

If you’re thinking about entering this space, Kristin recommended using Facebook ads, local Facebook groups, advertising on Nextdoor.com, and establishing relationships with local vets and dog groomers to grow a client base.

As far as pricing, she cautioned about starting out too low, as it might make customers skeptical. Her advice was to check on competitor’s pricing and aim for the middle.

What do you think? I still see a ton of opportunity in this local service business arena.

5. The 7-Figure Email Newsletter Business

One business model I’m fascinated by (and perhaps most likely to start myself if and when I take on a new venture) is the email newsletter business.

Think about businesses like Help a Reporter, The Skimm, The Hustle, and Morning Brew.

These are lean-mean, profit machines. In fact, Morning Brew, which provides a daily email roundup of business news, started in 2015 and by 2018 was a 7-figure business. More than a million people get their daily updates — expected to be over 2 million by the end of this year.

One of the co-founders, Alex Lieberman, explained the origins of Morning Brew on the Noah Kagan Presents podcast:

“The hardest thing is actually realizing there’s a newsletter to be created, as in there’s an actual appetite for it.”

If you want to get into this space Alex explains you need to identify a few key things, like:

  • Who are you writing for?
  • What’s your audience?
  • Is email the best delivery mechanism for them?

If you can identify a need within an audience and constantly put out quality information, you’ll grow your list and find yourself with a really engaged audience. Alex summed it up perfectly, adding “If people like something they’re going to become your best evangelist and salesperson.”

6. The Ambient Noise Alexa Skill

As you may know, one of my experiments this year is an Amazon Alexa Skill called The Money Making Minute. If you ask Alexa to enable The Money Making Minute as part of your flash briefing, you’ll get 60-second money-making ideas 5 days a week. (You may hear some of the ideas from this episode on there as well!)

What I didn’t know is that Alexa skills are kind of like apps in the Apple App Store, meaning you can set a price and actually earn developer royalties on them.

As a skill developer, you can set your own price and earn 70% of the revenue when users buy it.

For example, software engineer Nick Schwab created a free ambient noise skill, and now, per CNN, has 10,000 paying customers for a premium subscription version, priced between $0.99 and $1.99 a month.

That translates to at least a $7000 a month side hustle. And combined with the Sleep with Me podcast above, illustrates that apparently there’s big money in helping people fall asleep!

Amazon also has a rewards program to encourage developers to build out the ecosystem of skills. Your rewards are based on the popularity and engagement of your skill, but some developers report earning thousands of dollars a month.

What kind of skill could you make? Hat tip to Dave Shorr for sharing that one!

7. Big Bat Houses

Steve Barlow is a wildlife biologist, and his passion for wildlife dates to an early age. Growing up, his dad, who was a home builder, encouraged his passion but also wanted to make sure Steve learned the construction trades “as a fall back in case the biology stuff doesn’t work out.”

So, along with pursuing an advanced degree to be a biologist, he also built several homes with his dad and learned how to build.

Where the side hustle comes into this story is in how Steve has married these two skills into a pretty rewarding part-time business — and that is building big bat houses. You can see exactly what these big bat houses look like at BigBatHouses.com:

big bat houses

They’re physical structures that stand 12+ feet off the ground, and can house thousands of bats, and Steve sells them at prices ranging from $2500 to $4000 a pop.

The idea came from some research in his professional biologist career — Steve found himself researching different bat houses, experimenting with building materials, colors, sizes, techniques, placement etc.

He soon found bigger bat houses seemed to work better and also attracted larger colonies of bats, so he started designing bigger and bigger bat houses!

When Steve wrote in to share about his side hustle, he said he also noticed that most wildlife biologists, park managers, refuge managers and park rangers often had no construction skills–or if they did, no resources to build a large bat house.

So, he thought…. I need to design a bat house as large as possible but not too large that it can’t be easily shipped and installed.

As far as marketing, he attended trade shows and bat research conferences when his schedule and budget allowed. Steve started out building the houses himself, but as he got more orders, he found a 3rd-party construction company that could build them in their downtime.

Steve has sold bat houses in 58 cities, 19 states and 2 countries so far, and the business did around $50,000 in revenue last year — and continues to grow.

He told me his goal is to intentionally house more wildlife than anyone in human history! Steve signed off with, “Building houses like my dad, just for a different market!”

My Take

I like this side hustle because it’s a great sweet-spot example — combining a pair of different interests or skills to come up with a unique and profitable business.

I share this one not because I expect you to become a bat expert, but to get you thinking of what potential sweet spots you might have in your own life. Remember when Bryan Orr combined his knowledge in heating, ventilation, and air conditioning with his love of podcasting to create HVAC School?

This is actually an idea I heard explained by Scott Adams, the creator of Dilbert, on the Tim Ferriss Show. He said one way to come up with ideas is to look at the areas of your life you’re better than average at — like top 50%, top 25% — and then combine two or more of those into a sweet spot business.

8. The Niche Service Provider Directory

Is there an opportunity to create a helpful, curated site in your niche or industry?

One interesting example I came across was Nick Edmundson’s WanderingWeddings.com.

On the site, he and his wife highlight wedding photographers and other vendors that specialize in adventurous, outdoor, private, modern elopement-style weddings–and earn $4-6k a month in directory listing fees.

Nick explained to me how he identified a need for a directory within his niche and built his own, saying, “The more we shot these weddings, I wanted to submit them to publications somewhere. At the time there wasn’t a company or blog out there that was accepting these types of sessions. So, being the entrepreneur that I am, I started a website.”

They started out building a brand on social media, focusing on Instagram and Pinterest since it’s a visual niche.

Nick reached out to people he knew to get started, and started sharing their work. Organically, they’d begin sharing the account, Wandering Weddings started gaining as many as 4000 followers a week on Instagram.

wandering weddings on instagram

Then he started monetizing the site with a paid directory. “We had people submitting applications like crazy to be part of what we were building because we had already built this following and this brand first.”

Is there already a directory for your industry? Could you niche it down a bit more like Nick did?

My Take

This is the business model of The Yellow Pages, it’s one that’s worked for a long time — connecting businesses and customers.

The niche directory, or the Niche Service Provider Directory as I’m calling it is something we touched on a little bit in episode 282 with Brett Lindenberg.

The challenging piece of it, and this is what Nick is focusing on right now, is building the demand side of his marketplace — how can he drive enough traffic to these vendors such that it’s worth their while to be featured?

9. The Niche Productized Service

Last month I connected with Jeff Howell of LeaseRef.com, where he’ll review your commercial lease for a low flat fee.

(Or at least low compared to what a real estate attorney would charge.)

And in exchange for that flat fee, Jeff will give you a scorecard on some of the language in your lease to be aware of or any red flags that stand out. He had tons of experience doing this in his professional career but didn’t see anyone offering the service online in a compelling, easy-to-understand and do business with type of way.

There are a few cool things about Jeff’s business I want to highlight, which has grown to over $7000 a month without advertising.

The first is that all his traffic and sales come from content marketing and organic search. To come up with content ideas, he just looked at the commercial leases he was already familiar with and started writing articles about the common clauses or sections of those.

For example, he’s got 5,500 words on the tenant improvement allowance. That way, he gets people finding his site who are probably in the midst of poring over this legal document and trying to make sense of it.

By providing helpful in-depth content, he builds trust, and a certain percentage of those visitors hire him for an expert 3rd party review.

The second cool thing is that when he raised his prices, his conversions actually went up. For his customers, there was such a thing as being too affordable. With price comes perceived expertise.

(Jeff created a coupon code for Side Hustle Show listeners. If you happen to have a lease you need reviewing, enter discount code sidehustle for 15% off — valid through December 31st, 2019.)

And that brings me to the third thing — with the right product or service, it may not actually take that many customers to make a meaningful income.

Sure, this isn’t passive income, and even Jeff admitted it’s not the most exciting work in the world. But he’s become very proficient at it and could potentially add team members to help with workload should the need arise.

Could you build a similar productized service in your industry or niche?

10. In-Person Classes

One of my favorite examples of an in-person class side hustle that’s done really well is Greg Wenderski, of Austin, Texas. His email caught my attention with the subject line: “I make Bronze Age swords with kids.”

Greg is a former middle school science teacher who’s turned sword casting from his side hustle into his main source of income.

In his email, he said he was inspired by the Ancient Civilizations teacher down the hall — she was really into the Ancient Greeks and got the kids all excited about a battle formations, classes of soldiers, etc. So, Greg thought it would be cool to show the kids how Bronze Age swords were made.

Turns out kids of all ages are into molten metal!

Today, Greg travels the country and teaches in-person sword casting classes for $90 and up per seat, and sells some of the finished products on his Etsy shop.

You can check Greg out and see if there are any upcoming classes near you at SwordCastingGuy.com.

My Take

We touched on this a little bit in our Airbnb experiences discussion in episode 347, where my guest Michele had sold hundreds of guided meditation experiences at $50 apiece.

We touched on this a little bit in our episode on teaching after school programs. I think there’s a lot of opportunity in this space, either under the umbrella of the “experience economy” or just teaching something you know to a local audience.

What kind of class could you teach? How could you tap into existing marketplaces, like Airbnb Experiences perhaps, to get in front of customers?

Your Turn

If you’re looking for more inspiration, make sure to check out our official list of side hustle ideas and subscribe to the podcast with the links below.

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7 thoughts on “10 Creative Side Hustles That Make Real Money – Part 2”

  1. Awesome episode, thank you. Had to go hunt down these episodes on these other great podcasts and now have more podcasts for my ever expanding queue. Hope to be successful enough to be a guest some day.

    Reply
  2. My favourite has to be dog walking/boarding! A total delight! I’m even thinking of creating a PPC landing page
    for offering these services as a sole trader in my area. This way I can make more money than doing it via Rover and similar services. [I teach people how to generate job free income on slashercareer.com ]

    Reply
  3. This is great. Thank you!

    Question on the newsletter idea: Would you charge a monthly fee for the newsletter, or would you write the newsletter for free, using it to build an audience and then monetize it with ad space?

    I’m sure for some niches one option will be better than another. But curious to hear your thoughts. :]

    Reply

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