17 Sept 2026
#61: Building a Business Around Adventure: The Aleutian Adventures Story with Kyle Kolodziejski
You don’t have to build the biggest business. You have to build the right one.
Kyle has spent nearly 30 years proving that. He built a career around fishing, adventure, travel, and some of the most remote places on the planet. He moved to Alaska without much of a plan, built his reputation as a guide and operator, traveled throughout Patagonia selling experiences he knew firsthand, started over more than once, and eventually found his way to leading Aleutian Adventures. And he did it without giving up the reason he chose this path in the first place.
In this episode of Kenversations, Ken Okonek and Kyle Kolodziejski get into what it actually looks like to build a business around what you value. They talk about betting on yourself, taking calculated risks, hiring for character over credentials, controlling the things you can control, earning customer trust, and recognizing that more growth isn’t always better growth. That last one is a big part of how Kyle runs Aleutian Adventures today. They already have demand. They already have waitlists. They could market harder and reach more people. They intentionally choose not to. Instead, the focus is on attracting the right people, protecting the experience, respecting the land and fisheries, and making sure growth doesn’t destroy the exact thing people are coming to experience. Kyle also shares why some of the hardest moments in his life led to his biggest pivots, how being stranded in Argentina during COVID changed his path, and why he believes following passion instead of money has ultimately created a pretty rich life.
And as AI and technology take up more of our lives, Ken and Kyle get into something that may become even more valuable: Places where you can actually get away from all of it. This one is about business, but it’s also about having the guts to build a life that actually looks like yours. Subscribe to Kenversations for more conversations with entrepreneurs, leaders, and people willing to do things differently.
In This Episode:
Kyle and Ken dig into building a career around adventure, taking calculated risks, hiring for character instead of technical skills, the business behind world-class outdoor experiences, building trust with customers, responsible marketing, intentional growth, protecting Alaska's wilderness, and why unplugged experiences could become even more valuable in an increasingly digital world.
Chapters:
00:00 Meet Kyle from Aleutian Adventures
02:12 Turning Adventure Into a Career
08:30 How Kyle Found His Way to Alaska
10:15 The Conference That Changed Everything
16:35 Betting on Yourself and Going All-In
24:45 Building a Career in Alaska's Fishing Industry
30:25 Control the Controllables
32:15 Hiring for Character, Not Just Skill
37:15 Leaving Alaska and Starting a New Chapter
42:20 Turning Patagonia Experience Into a Business Advantage
48:25 Marketing, Growth and Knowing Your Customer
56:00 Building a Career One Step at a Time
57:30 Choosing Family and Returning to Alaska
1:05:00 Getting Stuck in Argentina During COVID
1:14:00 Starting Over Again
1:18:30 The Opportunity That Became Aleutian Adventures
1:22:30 Rebuilding the Brand and Marketing
1:24:30 Why More Marketing Isn't Always Better
1:31:30 What's Next for Aleutian Adventures
1:34:30 Why Unplugged Experiences Matter More Than Ever
1:38:00 Protecting One of Alaska's Wildest Places
1:43:00 Closing Thoughts
