Stephen Regenold is the founder of GearJunkie and a leading voice in outdoor media, entrepreneurship, affiliate commerce, and digital publishing. Stephen built GearJunkie from the ground up, starting as a newspaper column to review new gear before turning it into one of the most influential outdoor media brands in America.

Along the way, he sold the company, helped spearhead a $40 million media rollup involving the company at All Gear Digital, traveled the world as a journalist, and learned firsthand how digital media has changed over the last two decades.

In this episode of the Twin Cities Business Show, Steven shares lessons from building and selling GearJunkie, the future of media in the AI era, affiliate marketing, startup investing, outdoor culture, and why he thinks many media companies failed while GearJunkie survived.

Topic include:

• 00:00 Introduction
• 00:18 Building GearJunkie Into a Media Powerhouse
• 02:34 The First Gear Review and Early Journalism Career
• 04:11 Creating a Media Business While in College
• 06:17 How Affiliate Marketing Changed GearJunkie
• 07:58 Staying Ahead in Digital Media
• 09:29 Selling GearJunkie and the $40M Rollup Strategy
• 12:24 The GearJunkie Hammer and Branded Content
• 13:56 The Sales Lesson That Transformed the Business
• 16:04 Do You Need Passion to Build a Media Company?
• 17:48 Why Niche Media Is Winning
• 19:32 Can Media Brands Still Be Built Today?
• 21:02 Why Print Is Making a Comeback
• 24:15 How Steven Would Build GearJunkie in 2026
• 26:01 Why GearJunkie Survived When Other Blogs Died
• 29:01 The Moment Entrepreneurship Became the Focus
• 31:31 Advice for Journalists Going Independent
• 32:30 Raising Five Kids While Building a Company
• 35:34 Can Journalism Be Fixed?
• 37:54 Bringing Outdoor Retailer to Minneapolis
• 40:02 Life After GearJunkie
• 41:49 What Founders Bring to Investing
• 43:03 The Craziest Adventures and Finding a Kidney in Patagonia
• 45:47 How COVID Changed the Outdoor Industry
• 47:48 The Rise of Run Commuting
• 49:22 Getting Started in Outdoor Adventure
• 51:25 What Makes Minnesota’s Outdoor Culture Unique
• 54:31 Closing Thoughts