The Retirement Business That Blew Up

I just wanted to make enough to pay the Costco bill. I ended up getting Porsche money. How my “retirement business” blew up beyond anything I could have imagined.

Peter Kay, your feral entrepreneur here. This is a story about when I was in my early 50s and thinking about retirement. Not the kind where you kick back with mai tais on the beach and call it a day—I’m a lifelong entrepreneur, wired to keep building, keep creating, out of choice, not necessity. I’ve been through six startups, from the wild ride of launching Hawaii’s first commercial website with CyberCom in the ‘90s to exiting Titan Key. Each one’s been a chapter in my feral entrepreneur saga told on these pages.But now, I’m after something different—the kind of business I can run for the rest of my life, something steady, fun, that’ll bring in a few bucks without chaining me to a grind. The idea hits: instead of starting from scratch, I’ll buy a business, take over something already humming, and ride it into my sunset years.

I Get No Fish

For five years—felt like a damn decade—I’m scouring business broker listings, talking to brokers, poking around for the perfect business to buy. I’m methodical, doing cursory due diligence on anything that catches my eye. But nothing really came out at me. Here’s one example: an online flag seller, raking in cash. Numbers look solid, operations seem tight. But then I ask myself the nagging question: “Do I really want to spend the rest of my life online selling flags?” The answer’s a hard no. Every time I dig into a business—whether it’s power tools or automated car washes—I hit the same wall. Is this what I want to pour my heart into? Am I ready to give it the effort a business demands? No. Frigging. Way. I keep coming up empty, frustrated but unwilling to settle. I’ve built too much, from XenTec to Avagence, to waste my days on something that doesn’t light me up.

Just Do What Comes Naturally

After years of dead ends, I’m done chasing someone else’s dream. Time to flip the script. I’ve done six startups; what’s one more? Startup number seven it is. But this time, I go back to first principles, like I did when I birthed CyberCom. What do I want to do for the rest of my life? Not a slog, not a grind—something fun, something that fits my retirement vibe. I’m sitting in Hawaii, a place I’ve loved since I moved here in ‘84 at 21 years old, barely a kid with a half-baked frontal lobe. Over decades, I’ve built a dream life here—the people, the land, the ocean, the weather. It’s paradise, and I’m living it. I’ve got a good story to tell, and I want to share it. Not just for me, but to help others live this dream too, while imbuing Hawaii’s precious culture within the new folks coming from the mainland.

LivingInHawaii.com Is Born

That’s when it clicks: I’ll build a platform, LivingInHawaii.com, to show people how to make the move and become a net positive to our way of life that we all hold so dear here. Launched in 2015, it’s a classic “I did it, and now I’m going to show you how to succeed too” setup. I’ll include Online courses and a community vibe, all about thriving in Hawaii—how to settle in, blend with locals, and uphold the aloha spirit. My business goal? Modest. I’m not chasing millions; I just want to cover the Costco bill. If this thing pays for my groceries, I’m overjoyed. At first, I slack a bit—but by 2017, I get serious. Every weekday, 6:00 a.m. to 9:00 a.m., I’m grinding on the project. It becomes a borderline obsessive labor of love. I fuss over every detail—website design, content, systems, workflow automation—because I’m obsessed with Hawaii. I spend hours tweaking a single page and still grinning at the end. I really found something I love doing and I honestly don’t care about making money. Wow.

Local Japanese Friend Jumps In

Enter Dylan, a close friend for decades and a real estate broker with a Japanese blend that’s as local as it gets. He’s impeccable—trustworthy, sharp, the kind of guy you’d bet your life on. I’ve known him forever, and his ethics are rock-solid, a rare find in a world of fast-talking brokers. As LivingInHawaii.com grows, Dylan becomes a key piece of the puzzle. My platform starts gaining traction: the newsletter’s adding a thousand subscribers a month, the YouTube channel has over 10,000 subscribers with videos racking up views. People trust me because I’m brutally honest about life in Hawaii—the good, the bad, the real. Subscribers start emailing, asking for advice: “Hey, I’m looking for a house. What do you recommend?” I’m no real estate guy, so I call Dylan. He tells me about referral fees—significant cash for connecting buyers with agents, especially for million-dollar-plus homes in Hawaii. Cha-ching.

Aloha Friday Show Takes Off

In January 2020, I launch a “Help Me Find a Home in Hawaii” service, linking subscribers with Dylan. The response is immediate—leads pour in. Dylan and I start meeting every couple of weeks, brainstorming how to help these folks. He’s got a brilliant idea: “Why don’t we take our talks and broadcast them live?” I’m all in. We kick off the Aloha Friday Hawaii Real Estate Show, a weekly livestream (active to this day in 2025) where we dish out honest advice about buying in Hawaii. It’s a hit. People trust my content, they trust Dylan’s expertise, and he starts closing deals—millions of dollars in real estate. I’m floored. Then March 2020 hits. COVID. I’m thinking, *Holy crap, we’re screwed.* But the opposite happens. People stuck at home are dreaming of Hawaii, craving an escape. The live show gets *more* popular, leads skyrocket, and LivingInHawaii.com starts making big money. Way more than the Costco bill.

Another Dream Comes True

I’m beyond stoked. This isn’t just a win; it’s every entrepreneur’s dream. LivingInHawaii.com isn’t a tech startup like Titan Key, but it’s tech-fueled, built on the systems and know-how I honed over decades and 6 previous startups. I’m running it alongside my day job at CyberCom, pouring in sweat equity—blood, sweat, and tears—on a shoestring budget. I had the vision, the plan, and the hopes but never saw this coming. The plan was online courses, not real estate deals. But thanks to Dylan’s nudge, I pivoted, and now the referral fees are rolling in. It’s wild. I built every brick of this business meticulously, fussing over details for the sheer joy of it. Unlike the high-pressure stakes of past ventures, this was supposed to be my chill retirement gig. I made it fun every step of the way, and now it’s paying for the Porsche and the Costco groceries.

The Feral Entrepreneur’s Triumph

This is startup number seven, and it cements it: I’m the real-deal feral entrepreneur. I’ve started from a blank sheet of paper three times now, turning concepts into money-making businesses that exit honorably. At 57, I’m living the dream. LivingInHawaii.com is my most satisfying venture yet—not because of the cash, though that’s nice, but because it’s pure joy. I love the topic, I’m passionate about sharing Hawaii, and I did it on my terms. No pressure, no desperation, just a retirement business I built for fun that exploded into something bigger. It’s the perfect blend of everything I’ve learned, from the hustle of The Day I Learned to Sell to the calm and collected exit of Avagence. I’m helping people live their Hawaii dream, preserving the culture I love, and making bank doing it. You can’t beat that. Aloha!