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The Retail Pilot

The Retail Pilot

By: Ken Pilot
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The Retail Pilot is a series of interviews conducted by Ken Pilot with “Leaders and Legends” of the Retail industry. Ken will focus the conversation on his guests’ career journeys and their greatest career accomplishments and disappointments; gather insight into their leadership styles; learn who inspired them as they progressed through their careers; identify brands they admire; discover challenges they have faced; and talk about where they think Retail is headed and how they are leveraging technology to get there. Hosted on Ausha. See ausha.co/privacy-policy for more information.All rights reserved Economics Management Management & Leadership
Episodes
  • Tanya Golesic, CEO of Mackage: From Canadian down to a Global Luxury Brand
    Jun 2 2026

    When Tanya Golesic took the helm of Mackage in July 2021, she inherited a Canadian brand with extraordinary product and almost no story. "The minute you put the product on, you wouldn't want to take the product off," Golesic tells Ken. "But it was lacking a brand story. It was lacking storytelling." Four years and a record-breaking 2025 later, the former Jimmy Choo president has transformed a down-outerwear specialist into a global luxury lifestyle brand—stretching price points to $3,500, balancing the men's-women's split, and betting on the Croatia national team at the World Cup. This is a masterclass in brand building from someone who learned the craft at Ralph Lauren, Marc Jacobs, Canada Goose, and LVMH.


    In this episode of The Retail Pilot, Ken sits down with Tanya Golesic, CEO of Mackage, to trace her journey from a Croatian immigrant family in Canada to the top of global luxury fashion, and to unpack how she's scaling Mackage beyond its outerwear roots. This is a conversation about craftsmanship, curation, building inside a private-equity-backed startup, and why fashion has more in common with sports than most people think.

    In this episode you'll learn:


    • How Tanya went from a Croatian immigrant family in Canada to leadership at Ralph Lauren, Marc Jacobs, LVMH, Canada Goose, and Jimmy Choo

    • Why she turned down Mackage the first time—and how a "six-and-a-half-year interview" led her to the CEO role

    • The "aesthetics that protect" brand ethos: why Mackage product must be fashionable, functional, and technical all at once

    • How Mackage shifted from 50% heavyweight down to a 12-month lifestyle business spanning leather, cashmere, ready-to-wear, and rainwear

    • Why 2025 was a record year with double-digit growth—and how launching a real spring collection unlocked it

    • The logo strategy: segmenting between a "quiet luxury" customer and a streetwear customer with flexible branding

    • How she stretched price points from $850–$1,200 up to $3,500 without raising prices across the board

    • The wholesale discipline: applying the 80/20 rule and pulling back doors to focus on top-tier accounts

    • Mackage's global retail expansion across Canada, the US, Paris, Japan, China, and Korea—and when to use partners vs. going in-house


    Don’t forget to subscribe to The Retail Pilot podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce.

    If you missed our last episode, where Pete Nordstrom unpacks the eight-year journey to go private, the strategic partnership with Liverpool that made it possible, and what's actually changed since May 2025, be sure to tune in.


    Connect with Ken:
    -Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube.


    Hosted on Ausha. See ausha.co/privacy-policy for more information.

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    55 mins
  • Pete Nordstrom: From public to private, Nordstrom’s gains momentum.
    May 19 2026

    In this episode of The Retail Pilot, Ken sits down with Pete Nordstrom – Co-CEO of the 125-year-old fashion retailer – to unpack the eight-year journey to go private, the strategic partnership with Liverpool that made it possible, and what's actually changed since May 2025. They explore why the Saks-Neiman Marcus merger created an opening Nordstrom is now seizing, how the Rack is scaling toward 25+ new stores a year, and where AI is genuinely moving the needle.
    Pete is candid about the failed 2017 take-private attempt, the Canada expansion that became his generation's "biggest black eye," and why no department store has ever successfully exported its model abroad. This is a conversation about staying relevant across generations, competing with Amazon and Walmart, and the unglamorous discipline of just trying to be the best Nordstrom you can be.


    In this episode you'll learn:

    • Why Nordstrom went private in May 2025, and why the 2017 attempt failed

    • How the Liverpool partnership came together: 51% Nordstrom family, 49% Liverpool, zero pressure to merge or exit

    • The real downsides of being a public company: morale, distraction, governance overhead, and a stock price tied to a struggling sector narrative

    • What's actually changed day-to-day since going private and the one thing Pete misses about public-company rigor

    • Why Pete sees the Saks-Neiman's merger as a once-in-a-generation opportunity for Nordstrom to capture market share

    • How Nordstrom is winning brand partnerships, top talent (like Yumi Shin from Bergdorf Goodman), and customers from struggling competitors

    • The Rack expansion strategy: 25 stores this year, with capacity to potentially open 50 annually

    • Why Nordstrom Rack competes more with Macy's than with TJ Maxx—and what that means for store growth

    • The competitive reality of Amazon and Walmart in beauty, marketplace, and replenishment, and why Nordstrom can't get left behind

    • Why Nordstrom's marketplace (launched 18 months ago) is one of the company's biggest untapped growth levers

    • The Canada lesson: Why no department store has ever succeeded outside its home country – and what Pete learned from trying

    • What Pete hopes will be true at Nordstrom's 150th anniversary – and why agility matters more than any specific plan


    Don’t forget to subscribe to The Retail Pilot podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce.


    If you missed our last episode, where Mickey Drexler tells all on how he operates with startup intimacy and five decades of wisdom, be sure to tune in.

    Connect with Ken:
    -Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube.


    Hosted on Ausha. See ausha.co/privacy-policy for more information.

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    46 mins
  • Retail Legend Mickey Drexler: From Building Gap & Old Navy to Running Alex Mill Like a Startup
    May 6 2026

    Retail icon Mickey Drexler doesn't do retirement. At 80, the man who built Gap into a $14 billion empire, founded Old Navy, and revitalized J.Crew is running Alex Mill like a scrappy startup, and loving it. "I love what I do more now," Drexler says. "I don't have someone breathing down my neck." This is Mickey unfiltered: no corporate boards, no bureaucracy, no focus groups. Just 30 team members, two stores, and a merchant's eye as sharp as when he reinvented Ann Taylor in the 1980s.


    In this episode of The Retail Pilot, Ken goes behind the scenes at Alex Mill to explore how Mickey operates with startup intimacy and five decades of wisdom. They walk through design boards covered in vintage scarves, discuss why "a great store looks like it was bought by one person," and unpack Mickey's weekend update ritual - clipping magazines, photographing street style, bringing visual inspiration to the team every Monday.


    In this episode you'll learn:

    • Why Mickey runs Alex Mill with only 30 people and why smallness is an advantage

    • The "white space" strategy: How Mickey identified opportunities at Ann Taylor, Gap, and Alex Mill

    • Mickey's weekend update: How he curates inspiration from magazines, street style, and everyday observations

    • The curation philosophy: Why less is more and how to edit 32 prints down to 3-5

    • "If you know, you know": Mickey's brand-right approach and why focus groups are the enemy

    • Why AI will never pick colors and what technology can't replace in retail

    • Biggest career mistakes: Hiring wrong executives, opening too many stores, expanding internationally

    • How Mickey got fired from Gap with no notice after building $14B - and what he wishes he'd done

    • Why wholesale helped Alex Mill reach minimums with only two stores

    • The tension between designers (what's next) and merchants (what's been) - and how to bridge it


    Don’t forget to subscribe to The Retail Pilot podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce.

    If you missed our last episode, where Nate Checketts (Rhone CEO) on why wholesale saved his brand, how women's beat 8 years of men's in 2, and building mental fitness into brand DNA, be sure to tune in.

    Connect with Ken:
    -Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube.

    See Mickey Live: Ken and Mickey will be together on stage at Commerce Next on June 24th - join them for an unfiltered conversation about the craft of retail.


    Learn More About Alex Mill:

    • Visit AlexMill.com to shop the collection

    • Follow @AlexMill on Instagram



    Hosted on Ausha. See ausha.co/privacy-policy for more information.

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    1 hr and 10 mins
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