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We caught up with Rox, a trailblazer in the creator space who’s been building and scaling tools for some of the biggest names online. He shares the story behind his exit from ThumbnailTest, his new projects, and some real talk about working with creators and handling money.

Hey! I’m Rox, and I build tools for creators. I’ve worked with creators as large as MrBeast, and started my own youtube tools company ThumbnailTest, which I sold earlier this year. Now, I’m working on video podcast hosting software, and partnering with creators to make Saas businesses.

Entrepreneurship

Do you reach out to creators to work with them or do they come to you? How do you identify creators you want  to work with?

So far people have mostly found me - MrBeast found me on twitter, and most people find me through my tools. Deciding who I work with has been a journey, but usually I focus on finding creators that are business minded, and will prioritize the business we’re working on. Many people would work with me as a side project, but to truly cofound something, it requires focus and intention and a different mindset. If it’s not a priority, it’s not worthwhile for me or for them. I usually trend towards either educational or inspirational creators as well, as they provide value beyond just entertainment, which results in better likelihood of success building a business.

Do you build projects with the intention of monetization, or what if you build something and can’t see a path to monetization from the jump?

Always with the intent of monetization. I don’t build anything I can’t see being monetized, unless it’s lead generation for another tool (ex: small free tool that upsells you to fancy paid tool).

What made you decide to sell your project? How did you decide it was the right moment?

I realized it would be a war to continue building the business, and I didn’t want to fight that fight. With YouTube’s A/B testing feature around the corner at the time, and every YouTube tools company copy pasting each other’s features non-stop, it didn’t seem like the right space to be in long term (as much as I love it).

Beyond that, I had really fallen out of love with the business - I hadn’t deeply enjoyed the work for probably a year at that point, so it was time for a change.

Conveniently, ThumbnailTest doubled its MRR in about two months towards the end of last year, which brought in a lot of acquisition interest, resulting in a good moment for me to exit and move on.

Did working with a major creator like Mr. Beast have any impact on your career?

Absolutely. It always feels weird to talk about it, but people respected me more after working for Beast. I think in this space there’s a lot of noise and bad takes out there, so working for big creators is often seen as the main badge of credibility.

Working there really showed me the difference in scale of operations of some creators. Beast is so large they have problems no one else has, and they need to solve them internally. It gave me really strong insight into what problems in the space are worth solving and which are “enterprise only”.

Money

What’s one money tip you live by?

“If a problem can be solved with $20, spend $20.”

I’m really bad with money, but this phrase has helped me a lot in reducing inconveniences in life. It’s amazing how many things you can buy for $20, and how much easier life can get.

What’s your opinion on funding vs bootstrapping a business? Did you raise capital?

I like bootstrapping, but raising has its place. For ThumbnailTest, I bootstrapped the whole thing. For this new business, I’ve raised some capital, mostly because I don’t want to do the engineering myself anymore (I’m a CEO now! It feels weird.)

For your first few projects, I’d definitely recommend bootstrapping so you can learn and make mistakes without burning hundreds of thousands of dollars. It also forces you to be more creative and bring reality into the room earlier :)

What is your current savings and investing stack/portfolio (i.e any retirement accounts, emergency fund, etc)?

Every dollar I have is in a 5.5% APY high yield savings account.

Everything else is intimidating and this feels pretty reasonable 😄.

After getting one of your projects acquired, what there anything you wish you knew about personal finances / taxes.

God business acquisition taxes are so confusing. Especially if you’re a single member LLC, everything gets even weirder.

My biggest lesson since starting a business was “People are taxes on income. Businesses are taxes on profits. Be a business”. I’ve saved a ton on taxes just by being an LLC and marking off business expenses throughout the year.

To learn more about Rox and stay connected, you can find him on Twitter or visit his website.

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If you want more resourceson building wealth as a solopreneur/entrepreneur, check these out:

• The Solo 401k handbook

• The Roth IRA handbook

• The Self-Directed IRA handbook

• The Guide to Paying Less in Taxes

• What is a Solo 401k?

• How to Open a Solo 401k