"On the hard days, you need something to look toward. Only quit if the original hypothesis behind your business changes — not because you're tired."

We had the pleasure of talking with Kai Stone. Kai is an entrepreneur, surfer from Hawaii, and reality TV personality known for his outspoken takes and unapologetically bold opinions. As the founder of StoneSystems.io, Kai built one of the fastest-growing software brands for contractors in America — blending sharp marketing instincts with raw authenticity. Loved and hated in equal measure, he's become a polarizing voice redefining what it means to build wealth, freedom, and influence in the digital age.

What brought you to your specific career path?

I actually played professional video games in high school, so that's where I first learned what it really takes to get good at something. It taught me discipline, extreme repetition, and how to handle failure. It was the first thing I worked hard at, and ultimately failed at — but that competitive drive stuck with me. When I eventually found business, I treated it the exact same way I treated esports: put in every hour of the day, master the mechanics, and climb the leaderboard. The only real difference is that one uses fake numbers and experience points, and the other uses real money — which ends up being a lot more useful in real life.

What's the most interesting story since you started your career?

The most interesting thing has been the amount of self-confidence I've developed from being able to financially provide for myself and the people I care about. There's a masculine urge to protect and provide, and watching that part of me grow was honestly one of the coolest things that's happened. It wasn't a single moment — it was realizing that I'm capable of taking care of myself and my family. That changed everything for me.

Which three character traits were most instrumental to your success?

1. Willingness to look dumb for a long time.

You have to be okay with looking stupid in front of people you respect. When I first started running ads, people on Maui made fun of me because my ads were cringey. I kept going anyway, and eventually those "cringe ads" turned into a multi–seven-figure business.

2. Caring more about finding what works than being right.

Entrepreneurship isn't about proving yourself correct — it's about finding the right answer, even if it proves you wrong. I've changed strategies, products, and messaging countless times because the data told me to.

3. Accepting that you'll work extremely hard without seeing results.

I went months with almost no traction. I got my first 20 clients after about eight months of grinding, which was maybe $4,000 a month. It took forever. But pushing through that phase is what separated me from everyone who quit.

How would you define success?

For me, success is freedom. People think success is money, but money is just the tool that gets you to the real prize — which is waking up and doing whatever you want. That's always been my issue in life: not the work, but the lack of choice. In school, I didn't hate learning; I hated being forced to sit there. At my 9–5, I didn't hate the job; I hated that someone else controlled my time. Success is waking up and saying, "Today I want to work," or "Today I want to play video games," and being able to do either without asking permission.

What unconventional strategy contributed most to your startup's growth?

When I came into the market, every ad was polished, scripted, overly professional, and honestly boring. I showed up and just said things exactly how they were. It ruffled a lot of feathers, and it was definitely risky — it could've wrecked my reputation — but contractors resonated with the authenticity immediately. Nobody else was talking to them like real people. That difference helped us scale insanely fast.

What was the critical pivot point in your startup's journey?

The biggest pivot point in my entire career was partnering with my business partner. I call him my little Elon Musk, or the Sam to my Frodo, or the Robin to my Batman. He's everything I'm not. That partnership was the biggest decision I've ever made, and it turned out to be the best one. We complement each other perfectly, and it changed the entire trajectory of the company.

How do you balance rapid growth with a healthy company culture?

It's actually pretty simple: as soon as something breaks, we ease off the gas, fix the constraint, then push forward again. We solve whatever the biggest bottleneck is at that moment — whether it's hiring, onboarding, customer service, or product issues. Once the problem is solved, we continue scaling until the next constraint appears. That cycle keeps growth fast but controlled.

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5 Things You Need to Succeed as a Young Person in Business

1. Be willing to look dumb and make risky decisions. My early videos and ads were cringe and embarrassing. People laughed. But those same ads ended up fueling the growth of my entire company.

2. Work without reward for a long time. It took eight months of grinding before I even made $4,000/month. Most people quit during that phase.

3. Accept that you will lose friends. Some people won't support you. You'll be your own cheerleader for a long time. Today people root for me, but nobody rooted for me when I was up at 1 a.m. at my mom's house fixing automations so I didn't lose a client.

4. Commit 100% for at least one year. I promised myself I'd give everything I had for one year, no matter what. That commitment kept me from quitting when it got hard.

5. Believe in the vision like it's your North Star. On the hard days, you need something to look toward. Only quit if the original hypothesis behind your business changes — not because you're tired.

What advice would you give an aspiring entrepreneur?

Entrepreneurship isn't glamorous. You'll work twice as hard as your 9–5 and make less money for a long time. You'll lose sleep, friends, comfort, and certainty. You'll work without knowing whether it will pay off. But if you keep pushing long enough, eventually it does.