I Tested 100+ Side Hustles Over 7 Years. Here’s Everything I Learned So Far.
Vital Takeaways For What Works…And What Crashes & Burns
In 2018, I read a Reddit thread that said people were printing passive income by running video reward ads on their smartphones.
This “phone farming” side hustle sounded like a dream come true. So, much to my girlfriend and housemate’s amusement, I scrounged up 9 burner phones, set up some of these beermoney apps, and turned my college bedroom into an advertisement fraud MACHINE:
I also made, like, $20 per month at most 🤑😎🫠
As it turns out (shocker), the people on Reddit saying I would easily clear $500 per month with my phone farm were lying! Who knew!
This was one of my first lessons in Side Hustling 101: If something sounds too good to be true, it probably is.
It was a valuable first lesson. But it was also the start of something much larger I never could have fathomed.
Over the next 7 years, this phone farming side hustle would go on to change my entire life.
It was the single catalyst that got me interested in making money online.
It was also the fuel that lead me to start a 7-figure blog, become a digital nomad, write for Forbes, and travel to dozens of countries across 6 continents, all while earning a living with my laptop.
It really has been a wild journey since 2018.
And after testing out over a hundred different side hustles along the way, I thought it was about time I share some of the most valuable lessons I’ve picked up along the way.
This isn’t a sales funnel for a side hustle course I’m selling. And it’s not even an exact prescription for the kind of hustle I think you should start in 2025 or whatever year you’ll read this in.
Instead, it’s more of a reflection on how to approach side hustles in general to increase your odds of success. It’s also outlining some common pitfalls I’ve experienced or witnessed that can derail your income growth and opportunities.
Lesson 1: There’s 4 Types Of Side Hustles, So Know What You’re Getting Into
I’ve been testing out and writing about side hustles since 2018.
In this time, I’ve tried a lot of hustles. And if I haven’t tried something personally, I’ve probably interviewed someone who has or paid a freelancer writer to create content about their own experiences.
ALSO: the question I get the most over on YouTube or in emails, hands down, is “what side hustle should I start?”
People want to know the best way to make more money. And for many people, “best” is synonymous with “fastest” in their minds.
This is honestly true for most people…You just need a bit of extra cash to hold yourself over until payday hits.
However, this type of side hustle thinking is also limiting.
And, I’d argue there’s actually 4 main side hustle “buckets” you can choose from.
Each one has different pros, cons, and skill requirements. This is why I think it’s vital people actually take the time to conceptualize these buckets and pick the route that makes the most financial and logical sense for them.
Here are the buckets:
Quick Cash: Think survey sites, gig economy apps like DoorDash, cash-back apps, gaming reward platforms, walking dogs with Rover and so on. Most of these options don’t pay more than a few bucks per hour, especially the online ones. But this could be viable if you live in a country where $3 USD per hour is impactful. And the gig economy can be fruitful if you just need to pay down debt or make some extra rent money.
Delayed Cash (Semi-Passive): People hate on passive income hustles all the time because they are often sold as being way better than they actually are. I mean, take a look at phone farming. But you can find scores of people on YouTube or elsewhere making decent money with vending machines, Turo fleets, outsourced Airbnbs, laundromats, and other similar businesses. If you can outperform the market or a high-yield savings account and enjoy this kind of hustle, it’s not off the table.
Career Fuel: People don’t talk about this enough. But for most people, I think spending time learning new skills, updating your resume or certifications, and applying to new jobs gives you the best ROI. Job hopping is so underrated just from a salary-boosting perspective. And yes, the job market is absolutely cooked right now, but leveling-up your skills can be done for free on the Internet while you look for new career opportunities.
High-Leverage: Think side hustles that turn into scalable businesses or that can be outsourced. This is where people begin increasing their income disproportionately to the time they invest. For me, this was milking Google organic search traffic to a personal finance blog that made over $1,000,000. It’s also been publishing content on YouTube until one viral video helped propel me to over 130,000 subscribers. But this high-leverage play could be growing social media theme pages, building an app, AI-powered SaaS plays, and so many other routes. However, this route can be a trap if you’re hoping for quick, guaranteed money.
Okay, that was a lot of defining what a ton of people probably know already.
But, I think this kind of definition is important.
The main reason?
Most people dip their toes into the wrong side hustle bucket because they’re chasing dollar signs.
I partly blame course sellers and affiliate marketers for this, which includes me.
But how many people have tried dropshipping, or Amazon FBA, or some other “high-leverage” side hustle, when the Quick Cash bucket would actually make a noticeable improvement to their life?
This was something I got asked all the time as a blogger…Should I start a blog? How do I build an online business?
The blunt truth is that for a lot of people, DoorDashing on a bicycle (free exercise, no gas) or listing some service on TaskRabbit would probably have a more positive impact than buying a Dropshipping course and then spending $1,000 testing Facebook ads.
That’s not to say chasing high-leverage hustles or passive opportunities isn’t worth it. But there’s a time and a place. Sometimes, you need to boost your income and build a cash cushion before you go for a higher-leverage opportunity.
Take it from a guy who was a Starbucks barista and phone farmer throughout college!
Lesson 2: People Generally Don’t Fail Fast Enough
“You need to fail to succeed.”
This mantra is something you hear all the damn time.
It’s incredibly accurate. I think the main reason is because people get outsized returns by taking outsized risks oftentimes. But I’m not 100% sure, and it’s more complex than that even from a psychological development perspective.
But failing in slow motion or not even realizing you’re failing are vastly different than the “Move Fast and Break Things” mantra that’s more useful in my opinion.
Yet, this was me to a tee for years when it came to blogging and YouTube.
I spent most of 2018–2021 writing and creating most of my own content. I’d publish an article a week…Maybe 2 videos a month. I was editing my own footage too, making awful thumbnails, and wasn’t really setting any growth goals or metrics.
I was still growing year-over-year. But this gave me a false sense of progress and, more importantly, my actual potential.
Eventually, I heard some sage advice: “When you find something that’s working, do more of it.”
DUH.
But yeah, I quadrupled my content output, started paying freelance writers, got an affordable agency to edit my YouTube content, and went from making $22,000 with my blog to making over $500,000 in a single year.
I still catch myself in this trap to this day…Not iterating fast enough…Not questioning what areas of my life could be improved by thinking differently/smarter/more efficiently and whatnot.
So, I encourage avid hustlers to set some income and progression goals in the first place so you have your North Star. This also lets you reflect on your progress in a measurable way, so you know if you’re moving fast enough for your liking.
Lesson 3: Stacking Complementary Side Hustles Is A Cheat Code
Most people aren’t Elon Musk.
They don’t start a payment processing company, then a rocket company, then a car company…
Instead, they buy a car wash. Then they buy a second car wash. And then a third. And then, maybe, they buy a laundromat for something a little bit different. Or if they’re feeling spicy, they pay some developer to make some SaaS for car wash owners. Or they create a YouTube / TikTok account about the day in the life of a car wash owner (I’m convinced all side hustles end down this path. I’m on it currently. I have no shame. I’ll vlog and make YouTube videos about whatever until I’m dead.)
Yet, I’ve seen a lot of friends and colleagues chase wildly different business models. Sometimes it’s super cool and makes them a lot of money. Most of the time, their Golden Goose starves to death and their new ideas don’t work either.
For most people, I think starting new ventures should complement your first venture in some way. Or, make sure you’re leveraging all of the knowledge and advantages you have over your new competition.
Just don’t let your Golden Goose starve!
Lesson 4: Take Profits Regularly…Most Of The Time
I’ve had a couple websites destroyed by algorithm updates over the years.
Like any Green SEO, I thought I was invincible for a while. But I legit cried after the Medic update. And FOR THE LOVE OF ALL THAT’S HOLY, do NOT mention the Helpful Content Update in my DMs or emails. It’s TOO soon.
Luckily, I had very solid advice from my parents about taking profits from my endeavors early on. This is why I ran an 80–90% margin blog and YouTube channel and ultimately decided against hiring full-time staff, buying more blogs, and going for a larger play and exit.
In another universe, maybe I sold off a bundle of content sites before everything came crashing down and made a few million bucks. But I doubt it.
This is why I think most people should again, set income goals. And decide at which milestones and points you take profits. I’d also err on the side of caution here if your pipeline of leads, traffic, customers etc isn’t easy to control.
If you’re playing for something much larger, like selling to a larger competitor or some magical exit, then of course, you probably can’t run a 90% solo-preneur business. You probably need staff, or inventory, or things that make your business inherently less of a cash flow cow. But this is fine too, as long as you know what you’re playing for and what chips are left!
Lesson 5: Side Hustle Courses Are Almost-Always Worse ROI Than Consulting Calls Or Industry Events
If you don’t know by now, I hate online courses.
I also hated University…And Highschool…And really any form of school since Kindergarten.
I’ll probably eat my words here because again, like everyone else in the world, I’m sure I’ll sell a course at some point 🫠
But in my experience, investing in online courses is almost-always worse ROI than paying an expert for a quick consulting call. Attending events is also better in my experience.
Courses can also cause paralysis by analysis. But if you pay a Facebook Ads Expert $300 for an hour of their time and advice, you get technical help right then and there without having to bullshit your way through 16 modules and a fake live webinar.
Lesson 6: Choose The Pond You Play In VERY Intentionally
This is similar to lesson 4 in some sense.
I think side hustlers really need to identify and know the pond they’re choosing to play in.
Personally, one of the main reasons I also decided against hiring full-time staff and acquiring more blogs is because I don’t really like working with people for long periods of time.
I don’t like daily meetings. And if anyone ever brings up AGILE Sprint planning to me again like they did at my insurance company co-op, I will swiftly leap from my balcony.
It is totally okay to be a bigger fish in a smaller pond. Heck, you can be a small fish in a small pond too and still reap massive rewards. You don’t always need to scale up or diversify your side hustle because doing so can often lower your margins or open you up to new risks.
Again — outline your income goals and know where you need to swim.
Lesson 7: Vanity Metrics Derail Many Creators & Entrepreneurs
I’ve never really been on Instagram, LinkedIn, Twitter, Facebook, or any of these kinds of platforms.
I’m sure I’ve lost a fair bit of money doing this. And I kinda wish I hired one of those LinkedIn ghost writers years ago so I could be a top voice on blogging and Internet Marketing and shamelessly shill something on LinkedIn now.
Alas…It was not to be!
But the reason I never went to these other platforms was that the investment really wasn’t worth it.
I mean, I was making free money with Google and YouTube organic for years. I still am.
And since I haven’t really sold many digital products or coaching programs, platforms like IG never really moved the needle for my businesses.
However, I see a lot of side hustlers taking on 10 different platforms, especially when starting out.
This can feel super energizing. And the dopamine hit you get from repurposing content and plastering it everywhere is SO strong that somewhere, Gary Vee feels a little tingle in his soul and below his belt.
But in my experience, a lot of this is just a distraction in the name of vanity metrics. Followers, likes, comments and all that are great. Just loosely calculate the investment time and effort into revenue and progress towards your goals.
Lesson 8: Own The Platform Or Make F.U. Money As Fast As Possible
My last lesson for now!
This one really dawned on me after getting clapped by algorithm updates a few times…Own the platform, or make F.U. Money as fast as possible.
A lot of creators are talking about this, which is great. Business owners really should be collecting emails, building brand loyalty, and finding ways to build moats.
But again, it’s something that’s easy to forget, especially when the $$$ is rolling in.
Wrapping Up
I love testing side hustles. And I’m testing new ideas every month to cover on YouTube, WebMonkey, The Budget Diet, and other places my content lives now.
Hopefully, some of the lessons I’ve learned along the way help you out. Or, maybe you find them interesting at least. I’m thinking about making a Part II for this too, so let me know if that’s mildly interesting.
I’m excited to start writing on Substack too. It’s been ages! And I’m feeling quite the itch to write about industry changes, what’s on my mind, and to just create different content for the first time in years.
I hope you’ll consider sticking along as I do 😊
Catch you in the next one.
Thanks for the wise words Tom 🫡