This Side Hustle Spotlight Q&A features Dennis Tinerino, 39, of Los Angeles, California. Tinerino worked in online sales when he first learned about domain names and launching websites, which helped him discover domain investing as a side hustle. Here’s how he turned the gig into a lucrative business that brings in six figures a year — with about an hour or two of work per day. Responses have been edited for length and clarity.
Image Credit: Courtesy of Domain Smoke. Dennis Tinerino.
When did you start your side hustle, and where did you find the inspiration for it?
I started my side hustle in 2014 after discovering that domain names are like real estate, only online. Realizing the right ones could keep growing in value was all the inspiration I needed to dive in. My interest first sparked when I was launching a new website and came across a domain name for sale. I had no idea what the cost might be, so I filled out the form on the seller’s website. A domain broker from Afternic replied, explaining that the name was for sale and would require a six-figure minimum offer. Unfortunately, this domain was out of my budget for this project, but thankfully, they were very helpful and explained why it was valued at that price, even suggesting other names that were closer to my budget at the time. That conversation grabbed my attention and pushed me to do a deep dive into the world of domains.
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What were some of the first steps you took to get your side hustle off the ground? How much money/investment did it take to launch?
When I started, I did not know anyone personally who was doing this, so I had to teach myself. I dove into blogs, read FAQ sections on marketplaces and learned everything I could about how domains are bought and sold. Like most new investors, my first stop was GoDaddy, where I began registering domains that sounded cool or interesting. Luckily, I kept my spending in check and only bought four domains for a total of $36. One of them, LawyerBoss.com, ended up selling for $700 on Afternic less than two months after I bought it for about $8. That sale was a turning point. It was exciting to see that I could learn the process, list a name and have someone actually buy it for their business. From that moment on, I was hooked and started looking for more ways to find new domains to invest in.
If you could go back in your business journey and change one process or approach, what would it be, and how do you wish you’d done it differently?
If I could hop in a time machine, I’d go straight back and immediately sign up for the Domain Academy course on day one. It covers everything about domains, with resources from A to Z, and there’s nothing else like it. I could have skipped months of trial and error, saved a few gray hairs and gotten in the game faster with a deeper understanding of domains and the industry as a whole. There are countless strategies in domain investing, but before you dive in, you need to understand how domains work, what end users are looking for and the different ways to approach them. Trust me, learning this early is a lot cheaper than buying cool names and hoping for the best.
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When it comes to this specific business, what is something you’ve found particularly challenging and/or surprising that people who get into this type of work should be prepared for, but likely aren’t?
The hardest part for newcomers is getting the right education. Too many jump in blind, skip the basics and end up spinning their wheels. It’s like trying to fix a car without ever popping the hood. Making uninformed investments is a quick way to waste time, burn cash and get frustrated fast. Another big surprise is how much upkeep a domain portfolio requires. This is not a buy it and forget it business. You have to watch your names, keep up with renewals, follow the market and be honest when it is time to let go of names that are no longer relevant or valuable.
Can you recall a specific instance when something went very wrong? How did you fix it?
In my early days, I started doing outbound marketing to create interest and generate sales for my domains. I was not thinking about trademarks at the time and reached out to companies that owned marks similar to my names. That mistake earned me a stack of legal threats and cease and desist letters. Thankfully, I was able to resolve each situation on good terms by finding common ground with the parties involved. It was a valuable lesson to always check for trademarks before investing or reaching out to buyers, and I am glad I learned it early. Avoiding legal battles is high on my priority list.
How long did it take you to see consistent monthly revenue? How much did the side hustle earn?
It wasn’t until my second to third year of domain investing that I began to see consistent monthly revenue come in. What I noticed is that after my first year, when I started to educate myself more, build up my domain portfolio with better quality domains and then began outbound marketing, my sales accelerated, and steady monthly revenue came in. In the first year, I earned a few thousand with my first initial sales. In the second year, it was in the lower five figures, and it kept ramping up from there as I invested more time and resources.
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What does growth and revenue look like now?
Back in 2014, the portfolio was just a handful of domains. Today, it has grown to roughly 8,000 to 10,000 names. There were stretches where I was buying one name a day, and some days I went on a spree and grabbed 20, using profits to keep scaling and building the portfolio. Each year, I have consistently added another 500 to 1,000 names, experimenting with different top-level domains (TLDs) and country code top-level domains (ccTLDs) when I spot a trend. The real growth has come from .com domains, which remain the most in-demand with end users. What started as a few thousand dollars a year has grown into a business generating steady six-figure revenue for the past five years. That growth comes from years of research, relentless market tracking, careful portfolio maintenance and making the right moves at the right time, even when they were tough.
How much time do you spend working on your business on a daily, weekly or monthly basis?
On a typical day, I spend one to two hours building and managing my portfolio. Over a week, that adds up to 15 to 20 hours, and by the end of the month, it’s usually 60 to 80 hours.
How do you structure that time? What does a typical day or week of work look like for you?
My time is split between portfolio management, searching for fresh inventory, outbound marketing and closing deals. Each week, I set aside blocks of time to review my portfolio, adjust prices and prepare names for marketing. Once you get past a few hundred domains, daily portfolio management becomes essential. It is easy to let small tasks slip through the cracks, and that is when mistakes happen. What has saved me the most time is staying organized. It sounds easier than it is, but creating workflows, keeping detailed spreadsheets and using the right tools will save you from falling behind on your daily tasks.
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What do you enjoy most about running this business?
Domain investing can get a little lonely sometimes because you have to put in the hours to stay sharp and up to date. But the thing I have enjoyed the most is the investor community. We are very active on X, and I have met incredible people from all over the world who have helped me grow as an investor, taught me a ton and become lifelong friends.
The freedom that comes with this business is unlike anything else. You can run it from anywhere in the world with minimal tech skills. You set the rules, choose your hours, decide your prices, pick where to sell your names and choose which names you want to buy.
Over the years, as an investor, I found myself looking at tens of thousands of domains coming to auction or expiring every day. As great as many of those names were, I knew I could not buy them all, but I also did not want to see those opportunities go unnoticed by other investors. That got me thinking about how I could share this research and these findings with others. That is when I launched Domain Smoke, a daily newsletter sharing industry news, investment opportunities and the best domains hitting auction each day. Since its launch in 2019, it has grown to thousands of readers worldwide who read it every day.
Based on your journey so far, what’s your best advice for someone who wants to get started with this kind of business?
When I got started, there were a few things I would change if I could, and I hope my experience can help you find success in your own journey as a domain investor. If you are new to domain investing, here are three tips that can help you start on the right foot:
- Be patient with hand registrations
This one is not easy, but you will thank me later. Try to hold back from registering new domains by hand until you have a proper understanding of domain investing. The easiest mistake beginners make is buying names that are not likely to sell. Many of them also have little or no appeal to end users. That costs both time and money you will not get back. Once you get past the learning phase, you will have plenty of time to acquire domains that actually fit your strategy. When you know what to invest in, you will be glad you waited. - Invest in yourself early
They say the more you learn, the more you earn, and that is definitely true with domains. Avoid rookie mistakes by investing in your education. One of the best places to start is the Domain Academy course from GoDaddy, which teaches the ins and outs of the business. Just like any other form of investing, there are many ways to make money, but the best way to improve your chances of success early on is to educate yourself. - Keep learning and follow the data
It is easy to get started, build up a bit of knowledge and then think you know it all. But markets evolve, trends shift, and change is constant. Stay up to date with domain blogs, industry news, eBooks, Domain Sherpa shows and forums like NamePros, which is full of free knowledge for beginners. Most importantly, follow the data. Study sales and trends using resources like NameBio, dotDB and DNJournal. These will help you understand what is actually selling, what is trending and why. That insight gives you a competitive edge and keeps you aligned with the market.
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Start small, stay consistent and give yourself time to learn. Every successful investor was once a beginner. The more you study and track sales data, the sharper your skills will become. And remember, the community side of this business matters too. The investors and connections you build can be just as valuable as the domains you own.
