A Life of Adventure That Led to Chelan Ridge Winery | Bill Swayne episode artwork

EPISODE · Jan 16, 2026 · 1H 14M

A Life of Adventure That Led to Chelan Ridge Winery | Bill Swayne

from Small Towns: Unscripted · host Small Towns Unscripted

Bill Swayne was raised on Bainbridge Island at a time when it truly felt like a small town—close-knit, grounded, and deeply connected. That upbringing sparked a curiosity for the world beyond the island, leading Bill down an unconventional early path. He became a cook in Hawaii, then took a job aboard a yacht bound for Tahiti, embracing adventure long before it became a buzzword.While in Tahiti, Bill received his Vietnam draft notice, a moment that changed everything. Rather than waiting to be drafted, he chose to enlist in the United States Air Force, entering a defining chapter of service during the Vietnam conflict. The experiences that followed—some intense, some unforgettable—shaped the discipline, adaptability, and decision-making under pressure that would later define his business career.After his military service, Bill transitioned into the world of investment banking and financial advising, ultimately building a long career through WMS Wealth Management. His work focused on wealth strategy, real estate investment, and 1031 tax-deferred exchanges, and his accomplishments included raising capital and managing complex projects in many cities, guiding deals from concept through execution.That entrepreneurial mindset also led Bill into far-flung ventures, including gold mining pursuits in Alaska, where calculated risk, grit, and opportunity once again intersected—lessons that reinforced his belief in disciplined investing backed by real-world experience.Throughout every chapter of this journey has been Candice, the love of his life and business partner of 53 years. Together, they navigated military service, finance, entrepreneurship, and ultimately a shared vision that led them to Chelan, Washington.In 2021, Bill became the majority owners of Chelan Ridge Winery, marking a new chapter that merged decades of financial discipline with agriculture, hospitality, and community investment. What began on Bainbridge Island and stretched across oceans, war zones, boardrooms, and remote Alaskan terrain ultimately led Bill home—to a small town that mirrors the values he was raised with.

Bill Swayne was raised on Bainbridge Island at a time when it truly felt like a small town—close-knit, grounded, and deeply connected. That upbringing sparked a curiosity for the world beyond the island, leading Bill down an unconventional early path. He became a cook in Hawaii, then took a job aboard a yacht bound for Tahiti, embracing adventure long before it became a buzzword. While in Tahiti, Bill received his Vietnam draft notice, a moment that changed everything. Rather than waiting to...

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A Life of Adventure That Led to Chelan Ridge Winery | Bill Swayne

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This episode was published on January 16, 2026.

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Bill Swayne was raised on Bainbridge Island at a time when it truly felt like a small town—close-knit, grounded, and deeply connected. That upbringing sparked a curiosity for the world beyond the island, leading Bill down an unconventional early...

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