How My Fear Nearly Destroyed The Greatest Opportunity Ever

The untold story of how I was given the chance of a lifetime and nearly let my fear ruin it

In 1994, I stood at a crossroads, a scrappy entrepreneur with nothing but a wild idea and a shot at history. I’d just shown the World Wide Web to the Outrigger Hotels and Resorts IT crew during the Unix admin night classes I was teaching at Honolulu Community College. Joe, their chief technology officer, saw the future in those flickering pixels and threw open the door to build outrigger.com—the first commercial website in Hawaii, the first hotel website in the world. But that open door was just the start. I had to walk through it, close the deal, and get a check in my hand. This is the story of how I was gripped by fear, outmaneuvered a slick competitor, and gave birth to my fourth startup, CyberCom, in a moment that would define my life as a feral entrepreneur.

Door of Opportunity Opens

It all began with Joe, Outrigger’s CTO, a guy with enough vision to see what the web could do for his company. I’d been teaching Unix at Honolulu Community College, barely scraping by, my wife slinging rental cars to keep us afloat. Joe saw my demo and got it—Outrigger could be first. Not just in Hawaii, but globally. He invited me to pitch to the big dogs: Dr. Kelly, the CEO; Brian, the sharp-as-a-tack VP of marketing; and Bill and Lisa, seasoned marketing execs with a knack for special projects. These were heavy hitters, running a company that was a titan by Hawaii standards. Getting them to buy into an untested technology was no small feat. And then there was Ken, my mentor and the computer lab director at HCC. Ken was the one who first showed me the web, and he was all in, letting me use his classroom for the demo. He saw this as a chance to put HCC on the map and get his students jobs in a brand-new industry. Without Ken, I’d have been nowhere.

The Demo That Closed The Deal of My Life

Picture this: a gray, sparse classroom at Honolulu Community College, 1994. Metal desks, a projector, a screen, and me, sweating bullets but ready. In walks Outrigger’s top brass—Dr. Kelly, Brian, Bill, Lisa, Joe—executives from one of Hawaii’s most respected companies, staring at a technology they’d never heard of. The internet? The World Wide Web? Total unknowns. I fired up the projector and took them on a whirlwind. I showed them sites hosted on servers from France to California, graphics loading slowly but surely, including HCC’s own dinosaur exhibit. Their eyes widened; they’d never seen anything like it. Then came the climax. I pulled up a primitive search engine—pre-Google, pre-Yahoo, pre-everything—and searched for “hotel.” Nothing. Zilch. I turned to them and dropped the bomb: “You guys can be the first in the world.” The room exploded with possibility. Brian saw dollar signs: “We could take reservations from around the world!” Bill and Lisa were already mapping out how to showcase all 25 of Outrigger’s properties. Dr. Kelly, calm but decisive, said, “Peter, put together a proposal.” They walked out, and I was over the moon. I’d just given the most important demo of my life to the biggest company I’d ever pitched. They were hooked.

Competitor Threatens Everything

But hooking them was only half the battle. I still needed the check, and I had nothing—no office, no company, no bank account. Just a name I’d dreamed up: CyberCom. As I scrambled to write the proposal, a plot twist hit. A competitor, CNS Services, run by brothers Cameron and Sean, had caught wind of Outrigger’s interest. They’d teamed up with Andy, a local media personality and absolute powerhouse. Andy was a celebrity, larger than life, and I felt I’d lose in a head-to-head. Cameron for some reason made my skin crawl, triggering every insecurity I had. Sean was okay, but Cameron? He had an air of confidence on one hand but there was just something about that guy that didn’t feel right to me. They invited me to their office, and it was a power play. They flaunted their setup, their confidence, their “we’re the shit” vibe. Andy leaned in, all charm and swagger, saying, “We’re gonna get this deal.” I left their office rattled, fear creeping in. My future was on the line. If I didn’t close this, there’d be no CyberCom. I’d be back to teaching night classes, broke, with my wife grinding away at the rental car counter.

I Must Not Fear. Fear Is The Mind-Killer.

That fear could’ve crushed me, but I’d been here before. My six years at XenTec had taught me how to craft a killer proposal and close a deal. So I transmuted that fear into the “Outrigger Hawaii InfoWeb”. This wasn’t just a website; it was a vision. Twenty-five hotel properties, oceanfront photos, room details, and a reservation form—no credit cards yet, since secure transactions weren’t even available in ’94. Commerce on the web was taboo, barely legal. This was an informational play, but a bold one. I priced it at $50,000—$100,000 in today’s dollars—a massive bet on an unknown technology. No ISP even existed in Hawaii at the time - imagine - no one was even online! It was like betting six figures on some sketchy cryptocurrency. But I believed in it. I handed the proposal to Joe, reminding him Outrigger would be a pioneer, that the PR alone would be worth it. With all the confidence and calm I could muster, I gave him the price and asked for half up front.

The Check That Changed Everything

Days later, Joe called. The proposal was signed. A $25,000 check was mine. I walked into the bank, still a nobody with no business account, and handed over that check from Outrigger Hotels. The banker’s jaw dropped. He’d taken a chance on me, a scrappy startup, and here I was with a check from one of Hawaii’s biggest names to open the account. That money birthed CyberCom. We were in business, with $25,000 to build the first hotel website in the world before nearly anyone in Hawaii even knew what the World Wide Web was.

Facing My Fear Dragon

This was my moment of truth, just like the ones I’d faced before. CNS Services, with Cameron’s smug grin and Andy’s star power, could’ve steamrolled me. I was alone, no company, no resources, just a name and a dream. But I didn’t let fear win. I channeled it, like I always had, into action. I didn’t flinch asking for $50,000 or asking half up front. I didn’t let the competitor's intimidation throw me off the path. Fear is like a dragon. If you run away, it grows stronger. But once you confront it, it fades away like waking up from a bad dream. I faced the fear dragon and slew it, just as I had when I exited from XenTec only a few years earlier or pivoted after CyberCom’s exit many years later.

Victory, But Just the Start

Holding that check, I felt the weight of victory. But it was only the end of the beginning. That $25,000 came with trust—Outrigger’s trust that I’d deliver. CyberCom was born, but now I had to build what I’d sold, something that only a handful of people around the world knew how to do at the time. The stakes were high, the clock was ticking, and the web was still a wild, uncharted frontier. What I learned again here was to slay the fear, seize the moment, and build the future. That’s how CyberCom came to be and forever set in stone how I would move through life, slaying one fear dragon at a time.