Down to My Last Dollar: A Feral Entrepreneur’s Fight to Survive

What do you do when you have literally one dollar left in your pocket? You buy a McDonald’s chocolate shake and hand over the wheel.

Landing in Paradise

This is a story about hitting rock bottom—down to my last dollar—and how faith and Hawaii’s magic pulled me through. It’s 1984, and I’ve just moved to Hawaii from Chicago, 21 years old, with six months’ savings and big dreams. I’m cocky—think I’m the greatest programmer ever, fresh off Apple II and IBM PC microcomputer coding. I’m set on a tech job, but here’s the kicker: there’s no tech industry in Hawaii yet—none. This is the very, very, very start of the boom, and I’m clueless—pompous, full of myself, you know? I figure I’ll land something easy, but I’m dead wrong.

Burning Through Cash

By mid-1985, I’m a year in, and it’s rough. I’ve joined two businesses with partners—crazy ideas born from no jobs—both flops. Savings are shrinking fast—Hawaii’s brutal: high food costs, fuel, everything. I’m splitting a cool condo at the Waipuna in Waikiki with my buddy Dave—beautiful high-rise, near the top, commanding ocean view from my bedroom, breathtaking. Rent’s $1,100 a month—$550 my share—and it’s eating me alive. I’m down to peanut butter sandwiches, spending the least I can. I can’t even scrape together cash for a ticket back to Chicago—my “home”—a joke I tell myself, ‘cause there’s no way I’m going back, tail between my legs, a failure.

Facing the Edge

My dad’s words echo—he’d challenged me leaving Chicago, “Now we’ll see if you’re the man you claim to be.” He saw me as a bragger, full of it, and I’m not proving him wrong yet. I love Hawaii—head over heels after a year—but my savings dwindle, dollar by dollar, ‘til I’m holding my last one—a single bill in my pocket. I’m like, “What the hell am I gonna do with this?” It’s 1985; a dollar’s still something—I buy a McDonald’s chocolate shake, maybe 67 or 70 cents, can’t recall exact, but it’s all I’ve got. Evening’s coming; I savor it, sipping slow, staring at nothing, feeling the weight.

Teetering on Defeat

I’m out of moves—no credit cards, no line of credit, no one to ask for cash. I’m prepping for the worst—maybe a shameful call to my parents, begging for a ticket home. It’s terrible, you know? Contemplating leaving Hawaii, admitting I’ve bombed—but I’m not serious about it. I’m thinking it, sure, but no plan—no “tomorrow I call, confess I’ve failed.” I just can’t commit to that defeat—not with Hawaii in my blood. I crash for the night, last dollar gone, no idea what’s next, gut churning with dread and a weird calm.

Hawaii Steps In

Next day, literally the next day, I check the mail—there’s an envelope, a check for $1,921. I’m stunned—it’s an insurance settlement from a guy who rear-ended my ‘82 black Volkswagen Scirocco on the North Shore months back. I never fixed it, so this is pure cash—$1,921 in 1985! My rent’s $550; this is breathing room—plenty. Relief hits like a wave—I’m saved, no call to Mom and Dad, no defeat. I’m grinning, heart pounding—it’s incredible, you know? Hawaii’s got me, like it’s saying, “Hang on, brah.”

A Job Lands Fast

A couple days later—boom, rapid succession—a phone call. Guy named Sam from MicroWares says, “We saw your resume. Need a programmer now—can you interview?” I’m like, “Yeah, I’ll be there!” I show up, we talk tech—Unix systems, my thing. He asks, “How much you want?” I throw out, “Gotta be $2,000 a month,” can’t recall exact words, but they bite. Less than a week later, I’m hired—full-time, $2,000 a month, coding Unix, supporting clients, debugging software. MicroWares’s small, running Open Systems Accounting Software—customized heavy—and I’m handling accounts, building my own support gig. I’m in—cash flowing, alive again.

Meeting the Crew

Sam’s the principal—makes the hire, assigns my work. Marcus, his partner, later joins me at XenTec Software Engineering (XenTec Software Engineering Ignites)—another story. Guy’s the admin—bookkeeping, payroll, watches the books from a desk nearby. He’s a good friend—every Thursday, we hit a bake shop for eclairs, a special deal, amazing taste I still remember. Danny’s my co-worker—Japanese, runs cables, hauls hardware, does it all. He’s my first taste of samurai culture in Hawaii, a huge part of my life after. That crew pulls me into the fold—I’m not alone anymore.

Feeling the Spirit

Inside, it’s wild—those two hits, the check and the job, feel like Hawaii’s spirit accepting me. I’d been your classic loud-mouthed mainland haole outsider—jobless, unsettled—but this is my baptism of fire. Most folks washed out and moved back to the mainland back then—it was tough, way tougher than now, Hawaii closed tight. I pass the test; the islands take me in. I’m not just surviving—I belong. That faith kicks in—I’ve accepted Hawaii, and it’s accepted me. It’s special, you know? A threshold crossed—never since have I doubted I’d be welcome here.

Live or Leave Stakes

This was it—live my dream in Hawaii or slink back to Chicago, a flop. My parents would’ve taken me, prodigal son style—love and all, running the Blue Arc, a bar & restaurant in the Northwest side of the city where I essentially grew up. But I’d be miserable—heart knew it. This moment’s pivotal—collapse or climb. That check, that job—they’re relief, accomplishment, a sign I’m in. Hawaii’s got my back—stay true, and it’ll always be there.

Faith That Stays

Looking back, that faith—born then—never fades. Hawaii takes me under her arm; I’m safe, welcome, on my way to being local. Before, I’d watch workers commute, hear company ads, feel envy—outside looking in, a kid at the store window. Now I’m inside—job, cash flow, rent paid, food covered, a few bucks extra. MicroWares lasts nine months—my first and last job working for someone else—but it’s the start. That connection with Hawaii grows stronger every year—still does. I’ll always thank Hawaii for that dollar-shake day when she saved me.