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Get Vertical! Going from Idea to the Top 1% in Less Than 3 Years
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 tier nationally isn’t just difficult—it places a company in rare company.
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 one of the most recognized specialty run shops in America. The conversation explores career pivots, brand positioning, retail strategy, and the power of building 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.
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By MarketScaleIndependent 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 tier nationally isn’t just difficult—it places a company in rare company.
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 one of the most recognized specialty run shops in America. The conversation explores career pivots, brand positioning, retail strategy, and the power of building 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.