Episode Overview

Podcast: What We Wore
Host: Laura Vinroot Poole
Guest: Alissa Zachary, Founder of High Sport
Episode: 165 – “The Entrepreneurial Spirit”
Date: October 30, 2025

Laura Vinroot Poole welcomes Alissa Zachary, designer and founder of High Sport, to discuss her entrepreneurial journey in fashion, from her Dallas upbringing to roles at industry leaders like The Row, the genesis of High Sport pants, and the grit required to succeed as a female founder. The episode is heartfelt, insightful, and rich with industry wisdom, personal anecdotes, and reflections on style, family, and business.

Main Discussion Points & Insights

1. Origins & Influences (00:48–06:20)

• Dallas Roots and Family:

  • Alissa reflects on her close-knit upbringing in Dallas, the importance of extended family, and how her grandparents—her grandfather in oil and her grandmother an ahead-of-her-time fine art dealer—shaped her worldview and aesthetic sensibilities.
    • “When I think about my childhood in Dallas, it's mostly marked by spending time with family…that had a huge influence on me.” (02:00)

• First Fashion Memories:

  • From laying out clothes as a child to shopping with her mom, Alissa always viewed clothing as meaningful self-expression, shaped further by Dallas’s distinctive, dressed-up culture.

• Education and First Steps:

  • Studied Economics and Labor Relations at Cornell, influenced by her family’s academic path but driven by a growing passion for fashion and business.

2. Early Career: Learning the Business (06:25–15:21)

• Foundation in Retail:

  • Worked retail in high school at Dallas boutique Elements; this hands-on experience made her appreciate both the business and fashion sides.

• Corporate Training at Macy’s:

  • Joined Macy’s executive merchandising program, gaining critical understanding of global production, communication (pre-smartphones), and the value of diversifying manufacturing—a lesson that proved prescient.

• Transition to Designer Fashion:

  • Brief stint at Rebecca Minkoff during the “purse blog” era. However, Alissa’s ambition was set on designer apparel.

• Design Education at Parsons:

  • Immersed in patterning, draping, and technical aspects of clothing—she valued integrating design with business acumen for a well-rounded skillset.

3. Shaping Taste & Gumption at The Row (11:46–17:30)

• From Intern to Leader:

  • Started as an intern but essentially “chained herself” to the desk—and spent almost a decade at The Row, thriving in a fast-paced, small business environment.

• Key Lessons:

  • Extreme attention to detail, commitment to original vision, and quality:
    • “The Row never compromised on product or quality…believing that something is possible and wanting to see it through to fruition.” (13:15)
  • Learned to “not hear no”—a trait foundational to High Sport’s ethos.

• On Merchandising:

  • Alissa explains the vital role of merchandising as the bridge between sales and design, ensuring collections are both visionary and commercially viable.
    • “Without that bridge, you might really have a disconnect between those two areas of business." (15:52)

4. The Leap: Building High Sport (18:40–23:55)

• Life in LA & Motherhood as Catalyst:

  • Moving to LA and becoming a mother prompted Alissa to seek control over her schedule and pursue her own venture.

• Spotting the Gap:

  • Noted a need for tailored, stylish clothing that could comfortably transition across a busy woman’s day, inspired by observing LA’s manufacturing landscape.

• Four Years of Development:

  • High Sport’s signature pant took four years to develop, leveraging every relationship and piece of knowledge from Alissa’s prior experience.
    • “You don’t take four and a half years to make a good pant for nothing…by the time I brought it to market, it was a pretty good pant.” (23:41)

• Product and Brand Vision:

  • Launched with about seven styles—all in the same innovative knit fabric. The pants “struck a nerve,” becoming an instant hit through word of mouth among fashion insiders.

• Brand Expansion:

  • High Sport’s vision has expanded as the company grows:
    • “Now that I’ve seen what incredible potential we have and what the response has been…I think the sky’s the limit.” (24:00)

5. The Entrepreneurial Spirit: Grit, Growth, and Support (25:04–29:34)

• Navigating Highs and Lows:

  • Entrepreneurship is likened to emotional peaks and valleys:
    • “Being an entrepreneur, it's like…one day it's the lowest of lows…then next day you find out you don’t have to be EDI compliant to ship to Bergdorf and never been happier.” (25:12)

• Grit as the Core Attribute:

  • Alissa credits her perseverance ("grit") as the single most important quality for her and High Sport’s survival and success.
    • “That grit has been the single most important attribute.” (25:49)

• Support Network:

  • Family, friends, and former colleagues played crucial roles; Alissa remains grateful and emotional:
    • “It’s really pleasantly surprising in the unbelievable ways people show up to support you.” (27:42)

• Dealing with Naysayers:

  • Candid about warnings from friends and skepticism, but stresses the need for conviction:
    • “I had a friend…who said, ‘Don’t do this. Why are you doing this?’ And she was right, but I’m so glad I did it.” (28:44)
  • Emphasizes persistence:
    • “I’ve heard no every step along the way—from people who went on to invest, from stores that later carried the product…” (29:38)

6. Personal: Balancing Motherhood and Work (30:10–31:29)

• Kids Are Proud:
  • Her children are aware and proud of her business, even if she tries to keep work and home somewhat separate.
  • Hopes she’s setting a strong example, especially for her daughters who may encounter similar challenges balancing work and motherhood.

7. Pant Stories: The Emotional Power of Trousers (31:29–33:48)

• Prom Memories & Style:

  • Alissa is “homecoming queen” (31:33) and fondly recalls her high school fashion—mint green strapless Daryl K. suede dress.

• Why Pants Matter:

  • Customers share their emotional connections to transformative pants throughout their lives, underscoring how important well-fitting pants are for women’s confidence and movement.

  • “People have told me about, over the years, Chaiken and Capone, Joseph…pants are important to women. They allow women to move and do.” (33:16)

Memorable Quotes & Moments

• On Her Grandmother’s Influence:

  • “She worked from home…would hang and display the art in her house so people would come to her and see it…was ahead of her time as a working woman.” (02:31)

• On The Row’s Culture:

  • “To me, that’s always been the beauty of working at small businesses and now owning one. It’s incredibly dynamic…It’s not boring.” (13:03)

• On Product Vision:

  • “The brand is every bit as important as the product… I really want to own this idea of sporty, elevated lifestyle.” (24:00)

• On Grit:

  • “Grit has been the single most important attribute in whatever success… I’ve had at High Sport.” (25:49)

• On Support:

  • “It’s really pleasantly surprising in the unbelievable ways people show up to support you.” (27:42)

• On Naysayers:

  • “I had a friend…who said, ‘Don’t do this. Why are you doing this?’…But I am so glad I did it.” (28:44)

• On Women & Pants:

  • “When you make a pant brand, people will come to you and tell you about all the pants that have been meaningful to them over the course of their fashion lives…pants are important to women.” (32:54)

Key Timestamps

• 00:48 – Alissa’s Dallas upbringing and powerful family influence
• 02:31 – Grandparents’ career stories and cultural impact
• 04:44 – Early fashion memories, Dallas as a “dressed town”
• 06:25 – College and falling in love with the business of fashion
• 06:57 – Early work at Elements and Macy’s
• 11:46 – Life-changing internship at The Row
• 13:15 – Lessons in quality and belief from The Row
• 15:24 – Explanation of merchandising’s vital role
• 17:50 – Motherhood, leaving The Row, the shift to LA
• 19:36 – The seed for High Sport and recognizing needs in women's wardrobes
• 20:59 – High Sport’s four-year development journey
• 22:05 – Advice to young women: “Work for others first.”
• 23:41 – Launching with the pant: immediate customer connection
• 24:00 – Future vision for High Sport
• 25:04 – The peaks and valleys of entrepreneurship
• 25:49 – The vital role of “grit”
• 27:28 – The importance and surprise of support networks
• 28:36 – Navigating skepticism and sharing dreams
• 29:38 – Persistence in the face of “No”
• 30:10 – What her entrepreneurial journey means to her children
• 31:29 – Prom fashion memories lead to reflection on iconic “pant” brands
• 32:54 – How pants empower and emotionally resonate for women

Episode Tone

Warm, empowering, conversational, and deeply personal. There’s a steady undercurrent of encouragement for would-be entrepreneurs—especially women—tempered with realism about the challenges and isolation of doing something new, and lots of enthusiasm for craftsmanship, creativity, and community.

This episode is an uplifting listen for anyone interested in the architecture of a modern fashion brand, the strength it takes to go it alone, and the enduring power of a perfectly-made pair of pants.