47-year-old freelancer has 10 side hustles and 8 of them are making money

47-year-old Rodrigo Rocco has been working for himself for 14 years. His main hustle is freelance, but he is also side hustling in a big way.

He has a total of ten side hustles, eight of which are bringing in revenue.

Let's take a peek at his finances.

A family of side hustlers

Rod comes from a family of entrepreneurs.

His mother owns a restaurant and boutique hotel. The venture started as a side hustle and the "MVP" was baking cakes in her garage.

His father is an entrepreneur in the insurance industry. And it goes back even further to his grandpa, who had a truck delivery company.

I started from the ground up. That kind of entrepreneurship is in my veins.

Slinging code as a main hustle

When he was 12 years old, Rod stumbled upon a PC and fell in love. His dad enrolled him in a programming bootcamp and, just like that, he knew what he wanted to do with the rest of his life.

I remember dreaming about making a living by coding from anywhere in the world, even before laptops were invented.

Rod went to school chasing a computer science degree, but quickly found that university wasn’t for him. He was only interested in coding classes and playing with his IDE (integrated drive electronics).

So he took every penny he had — $300 — and started traveling. But that $300 didn't get him very far, so he started freelancing.

14 years later, it's still Rod’s main hustle — he builds custom “direct booking” websites for small hotels and short-term rentals of all kinds.

Accidentally starting a new side hustle

But Rod isn’t a one-business kind of guy. In fact, he has a whopping ten side hustles currently, with more to come.

His most recent side hustle started when StackOverflow Jobs shut down. He heard about it via a tweet from Pieter Levels and got to work. Within five hours, he built a quick, ugly directory of job boards. Then he commented about it on the tweet.

Pieter liked and retweeted it, so before the day was out, it had some traction.

He hadn't planned to make a business out of it, so he let it coast on the side. But then Pieter sent him a message two months later saying that he should charge job boards to be listed and add paid tiers.

So he did. And within minutes of tweeting about it, he had his first sponsor. That was 2 years ago. Now, there are 419 job boards listed and 196 in the waitlist. And in April, he had his best month ever, bringing in $7,320.

All up, this side hustle has brought in $40,063.03 over the last two years from a mix of subscriptions and one-time payments.

Side hustle revenue

Rod has nine other side hustles too, and most are revenue positive. Here's a look at he's bringing in monthly:

• Freelancing: $2k-$10k

• JobBoardSearch.com: $1.25k MRR + variable sponsorships (lately ~$1.2k)

• VillasMediterranean.com: $160k per year (average of $13.3k/mo)

• PropertyDescriptionAI.com: $58 MRR

• ReviewReplyAI.com: $10 MRR

• 24HoursVet.com: $0

• TouristItinerary.com: $0

• Rental properties (x4): Undisclosed

• Founder pay: ~$10k (variable due to seasonality)

• Personal bank account: Undisclosed, but not much — it’s all invested

• Emergency fund: Undisclosed, but enough to get out of a pinch

How to run ten side hustles

I'm a serial maker. I love it. Hopping between products keeps me motivated; otherwise, I would just get bored. Even now, I'm thinking about starting a little olive oil side hustle with a friend.

If you're wondering how he does it, Rod is a proponent of moving quickly. Launch a side hustle, iterate, and then see what happens.

Don’t wait to be perfect — it's never going to be anyway. Launch as fast as possible and fix it later based on user feedback.

The hardest part is staying consistent and accountable. But for him, the solution is straightforward. He builds in public, and sharing his daily updates motivates him to keep going.

Side-hustle expenses

An important part of side hustling — particularly when you have ten of them — is keeping monthly expenses low. And Rod takes pride in his setup:

• Cheap VPS for hosting all his projects (via OVH): $30

• Newsletter platform (EmailOctopus): $39

That's it. He says this is the golden age of bootstrapping.

Nowadays, with cheap server costs and remarkably easy ways to build MVPs, it makes more sense than ever to bootstrap.

Ditch the accountant to save money

While he's got a tight grasp on his business expenses, Rod doesn't track his personal expenses. It just doesn't interest him. His wife is the budgeter in the family, so he leaves that type of thing to her.

In fact, she took courses with the local government to improve her financial literacy and get on top of their finances. And she’s so good that they’ve decided to forgo the accountant altogether. That probably saves them a good deal of money — not that he would know.

All up, Rod thinks he spends something in the vicinity of $4k/mo.

Spending on travel

Rod doesn’t have guilty pleasures. He just has one big expense, and that’s travel.

He loves to travel and says the benefits far outweigh the costs, which are ample. But he doesn’t really have a choice anyway.

His daughter competes as a synchronized swimmer, so his family travels to see her compete all over Spain.

And then there’s his family in Argentina. And his Christmas tradition of spending the holiday season with friends at a villa in the mountains.

To him, it’s worth every penny.

Investing in real estate and crypto

Rod invests in two things: real estate and crypto.

No matter how many times people tell him to get into ETFs, he just won't do it. He says you need to know what you’re doing when you invest in something — otherwise, you might as well go to the casino.

And he just doesn’t have the will to learn about ETFs.

He chose not to disclose his investment numbers, but he invests almost all of his income, keeping as little as possible in savings. And he’s been doing so for years.

Real estate as a side hustle

Rod's properties are part investment, part side hustle. The investment part is paying off because they have gone up 10x in value since he bought them. And the side hustle part is thanks to the ongoing revenue they provide as rentals.

He has paid off all his mortgages except one, which only has about €90k left. And that’s good because he really does not like loans. He says there are times that they make sense — and times that you need them — but overall, they are a terrible choice for the borrower.

Interest rates on loans are abusive. You end my working for them.

Investing in crypto

Rod invests in crypto because he knows what he's doing and he trusts the underlying technology.

He can't say the same thing about Fiat money.

His investments are focused on the standard, and relatively stable, choices of Bitcoin and Ethereum.

Side hustle until it becomes your main hustle

With his ten side hustles, Rod is constantly trying new things. But he never loses sight of his main hustle — the thing that keeps the lights on and feeds his family.

He stresses the importance of hanging on to that until your side hustle is making a decent chunk of money — at least enough to serve as validation and preferably enough to pay the bills.

Don’t quit your job just yet. Build a side hustle and wait until it is generating money

You can find Rod on X or check out one of his many side hustles: JobBoardSearch, VillasMediterranean, PropertyDescriptionAI, ReviewReplyAI.com, 24HoursVet.com, TouristItinerary.com:.

Please note that the above are opinions. This is meant for informational purposes only. It is not intended to be financial advice.

And if you'd like to be featured as a guest in a future interview for this series, let me know in the comments!