Letting Go Of Yet Another Baby

What do you do when your planned retirement business blows up and gets serious? Read the true story of how my fundamental retirement assumption was completely wrong.

This is No Longer A Hobby

Peter Kay, your feral entrepreneur here and this is the story about the wild ride of my “retirement business”, LivingInHawaii.Com that came to a close at age 61. This thing started as a hobby—just something to pay the Costco bill while I kicked back in retirement. Eight years prior, I began chiseling away at it, three hours every weekday, building a platform to tell folks what it takes to live in paradise and be a net positive to the culture. It was a labor of love, like carving a perfect stone sculpture for the corner of a house. I savored every moment, developing features nobody else even dreamed of, hammering away at a sophisticated system that felt like pure craftsmanship. But, holy crap, it blew up way beyond my wildest dreams. Millions in real estate sales? That’s not a Costco bill—that’s a serious business.

Competition Creeps In

The Hawaii real estate world started noticing. My platform wasn’t just informing people; it was pulling in lucrative mainland buyers, folks with deep pockets dreaming of island life. Other realtors and brokers saw the goldmine I’d stumbled into, and overnight, competitors sprouted like weeds. I’d cornered the market—never a monopoly, but damn close—and now it was getting sliced up. My numbers took a hit. Suddenly, I’m spending my days studying rivals, countering their moves, fighting to stay ahead. I was winning, sure, but it felt like Titan Key all over again. I’m thinking, “Man, I wanted to retire, not run a freaking war room.”

Meeting in the War Council Hall

Enter Dylan, my co-host on the live shows we’d been doing for years. This guy’s a legend—local Japanese, impeccable ethics, and built one of Hawaii’s top brokerages on the Big Island. I’ve known him for decades, and he’s got this extra layer of grit from serving in the Army National Guard. Dylan knew LivinginHawaii.com inside out, its value, its edge. He wasn’t just a friend; he was the only guy who made sense to talk to about this dynamic. When he was stationed at Schofield Barracks on Oahu, we’d grab lunch whenever he was on duty. This time, it was Ruby Tuesday’s, right near the base, in one of those high-back booths that feels like a private war council.

Pitching Over Pepperoncinis

We’re loading up plates at the salad bar—piles of veggies, the works (especially pepperoncinis!) —and I’m laying it all out. “Dylan, this hobby’s gone rogue,” I say. “It’s a serious business now, and I just want to retire, pay my Costco bill.” I tell him how other brokers are copying us and building their own platforms which will compete against his business. He sees this happening and also understands that his brokerage will need to do the same or risk getting steamrolled. “But you don’t need to start from scratch,” I say. “Just buy mine.” I throw out a price well below what the business is worth. It’s not about squeezing every penny; it’s about handing the baby to someone who’ll value it more than I do. Dylan’s no fool. Right there, over our ridiculously high piled salad bar plates, he agrees. Deal done. Later on we announced the deal on our YouTube channel.

These Things Just Keep Getting More Perfect

I’m beyond stoked. This is the most perfect transaction I could’ve imagined. Sure, I could’ve tried to sell for more —real estate pros valued LivinginHawaii.com way higher than I did—but did I really need to squeeze every penny? This wasn’t supposed to be a mega-money-maker like CyberCom or Titan Key. I built it for joy, not money. Selling to Dylan, a close friend who knew the business cold, was a win-win. He got a really good deal and a competitive edge for his brokerage. I got out clean, happy with the price, and free from the growing swarm of competitors. It wasn’t like considering selling CyberCom, which in my mind did not have value worth selling, nor Titan Key, which really wasn’t worth pursuing any longer. This felt right, like passing a prized sculpture to someone who’d display it proudly.

Go Big Or Go Home?

The stakes were real. I had to choose: jump in with both feet, become a real estate agent, and fight the competition like a full-time warrior, or declare victory and walk away. This wasn’t my first rodeo. I’d learned when to hold and when to fold. LivingInHawaii.Com was worth millions to brokers, but to me? It was a retirement dream gone wild. Staying in meant un-retiring and pouring in time and money I didn’t want to spend. Selling meant freedom. It was a playbook I knew well: build, maximize, know when it’s over, and move on. This was not a painful or difficult decision. It made total sense to hand it to Dylan, who would value it more than I ever could.

Why Was This The Best Business Yet

This was the ultimate feral entrepreneur experience, better than any of my previous 6 startups. I built LivingInHawaii.Com from nothing, brick by brick, over eight years. Every feature, every gruelling hour, was pure passion. I’d spend days perfecting the smallest detail, not for money, but because I loved it. The money came by accident, way more than I needed. Selling it to Dylan at a fair price—great for him, great for me—was the cherry on top. It was a first-rate example of following your passion to success, enjoying every damn minute, and knowing when to let go. Eight years of chiseling in my back garage and I ended up with something incredible, super satisfying, and ultimately rewarding.

I Was Totally Wrong About A Retirement Business

Here’s the kicker: my whole premise was wrong. I thought I could build a “retirement business,” something to run while sipping mai tais on the beach. The big ah-ha moment? You can’t have both. You’re either retired or in business—pick one. Entrepreneurs, listen up, especially you retirement-age folks dreaming of a side hustle: you can’t half-ass it. Business means competition, long hours, and all-in effort. Retirement means letting go. I’m leaning toward retirement now. I’m comfortable, enjoying my beach in Hawaii. What more do I need to prove? I’ve done the slog—eight years on this, decades on others. I’m good.

Divine Path Beckons

I’m still working with Dylan, co-hosting our live show every other week. But business? I think I’m done chasing that dragon. There’s nothing left to prove here. Other challenges are calling, not business ones, but personal ones, spiritual ones. I’m firmly on a divine path now, like I’ve always been but just more focused. I don’t know where it’s leading—that’s the beauty of it. You follow, you have faith in an ultimate divine mind (I call it Jesus, you may have other labels), and it takes you to divine ends. That’s what I’m doing: staying feral, staying true, and letting the divine path unfold. Selling LivingInHawaii.Com was just one chapter. And by the Grace of God, the next one’s already started, even if I have absolutely no idea what it is or where it’s going. Aloha!