Get Vertical! Going from Idea to the Top 1% in Less Than 3 Years
This episode of Get Vertical! features Mike McCalley in conversation with Drew Flowers, General Manager of Trailhead Running Supply, exploring how a niche trail running retail concept reached top 1% status in the U.S. in under three years. The discussion covers career pivots, niche market positioning, and how authentic community building became the store's core competitive advantage. It offers practical lessons for independent retailers navigating one of the most competitive environments in decades.
This story was produced through MarketScale. See how Retail teams put it to work with Sales Enablement.
Promoted content from Get Vertical with Mike McCalley on MarketScale.
Key takeaways
Narrowing into a niche—trail running—created market leverage rather than limitation in a crowded specialty retail landscape.
Community building, not just product curation, was the defining factor that elevated Trailhead Running Supply into the top 1% of run specialty stores nationally.
Multiple career pivots—from construction to graphic design to outdoor retail leadership—shaped Drew Flowers' risk tolerance and operational expertise.
Independent retail is operating in one of the most competitive environments in decades. According to the U.S. Bureau of Labor Statistics, roughly 20% of new businesses fail within their first year, and a whopping 50% don’t make it to year five. At the same time, consumers are increasingly choosing brands that offer community, authenticity, and experience—not just products. In this landscape, building a specialty retail business that rises into the top 1% isn’t just difficult—it’s exceptionally rare.
So what does it actually take to go from a rough idea to becoming one of the top specialty stores in the country in under three years? Is it capital, connections, timing—or something deeper?
Welcome to Get Vertical! In the latest episode, host Mike McCalley sits down with Drew Flowers, General Manager at Trailhead Running Supply, to unpack how a niche trail running concept turned into a top 1% run specialty store in America. The conversation explores career pivots, brand positioning, retail strategy, and the power of building an authentic community in a hyper-focused market.
Top insights from the talk…
- How Drew executed multiple career pivots—from construction to graphic design to outdoor retail leadership—and what those transitions taught him about risk.
- Why narrowing into a niche (trail running) created leverage rather than limitation in a crowded market.
- How community-building—not just product selection—became the store’s defining competitive advantage.
Drew Flowers is the General Manager of Trailhead Running Supply, where he leads operations, builds strategic vendor partnerships, and drives community-centered retail growth. With a background spanning REI retail management, specialty run sales, and custom apparel production, he brings deep expertise in service-oriented sales, trend analysis, and team development. Known for cultivating long-term customer relationships and creating high-impact community events, Drew has been recognized for his leadership and commitment to core values.
Article written by MarketScale.
Part of this channel
Get Vertical with Mike McCalley
Vertical market strategy and revenue growth for B2B companies.
About the author
Mike is a leading marketer with expertise ranging from start up ventures to fortune 50 companies. With a passion for B2B and community building, Mike has evolved how traditional companies go to market and truly educate, inform, and inspire their community. When Mike isn't building out media and strategy plans for companies you can find him announcing his local high school football games and spending time with his family in Plano, TX.
