Season 4: Get Vertical! How Trailhead Went From Idea to the Top 1%

Описание: From Idea to a Top 1% Store

This business started 60 miles into a run — over an avocado quesadilla.

In this episode of Get Vertical! Mike McCalley ( @Endure121 ) sits down with Drew Flowers of Trailhead Running Supply (instagram.com/trailheadrunningsupply/) to unpack how a niche trail running store in Dallas became one of the Top 65 running stores in America — placing it in the top 1% nationally.

What began as a “crazy idea” at mile 60 of a canceled ultra race turned into a community-driven retail brand that competitors now try to emulate.

This episode is about more than running.

It’s about:
• Hard career pivots
• Niche positioning
• Vendor skepticism
• Experience design
• Community as competitive advantage
• Building something that can’t easily be copied

If you’re an entrepreneur, founder, retail operator, or leader trying to build loyalty in a crowded market — this conversation will resonate.

What You’ll Learn:

How Drew pivoted from construction → graphic design → REI → specialty retail leadership

The 60-mile moment that sparked the idea

Why vendors laughed at launching a trail-only store in Dallas

How to design a retail experience that tells a story

Why community became the true moat

How weekly rhythms like “Dirt Church” created momentum

What it takes to be voted into the Top 65 stores in the U.S.

Early mistakes with inventory and e-commerce

Advice for launching a niche business

Chapters

00:00 From Construction to Retail Leadership
03:30 The Leap from Design to REI
08:30 The 60-Mile Avocado Quesadilla Moment
14:00 Vendors Laugh at the Idea
17:30 Turning Skepticism into Partnerships
21:00 Designing a Store That Tells a Story
29:00 “Community Is the Secret Sauce”
32:00 The Trail Running Ethos vs. Road Racing
35:00 Dirt Church, Rocky’s Road & Weekly Momentum
41:00 How the Top 65 Selection Process Works
45:00 Inventory Mistakes & E-Commerce Lessons
49:00 Can the Concept Scale?
52:00 Advice for Niche Entrepreneurs

📍 Learn more about Trailhead Running Supply:
https://trailheadrunningsupply.com
instagram.com/trailheadrunningsupply/

🎙 Subscribe to Get Vertical for more conversations with founders and leaders who turn bold ideas into real momentum.
Connect with The Vertical Solution or Mike at:
theverticalsolution.com
@Endure121
instagram.com/mike_mccalley/


#entrepreneurship #retailstrategy #communitybuilding #smallbusiness #leadership #nichestrategy #founderstory #trailrunning