The Man Who Built Gap, J.Crew, and Old Navy Explains How He Spots Winners | Mickey Drexler

Guest
Mickey Drexler
Read time
~4 min
Uploaded
4 Feb 2025
Duration
0:49:10
Views
21.5K
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KEYPOINTS

  • 01

    Never give a customer a reason not to buy.

    Mickey Drexler, who reshaped Gap, built Old Navy and remade J.Crew, walks into a shop with a photograph in his mind: it either paints a picture or it doesn't. One bad colour throws off a great painting. Most cars today have ugly wheels; a best-selling sweater with an ugly button gets noticed for the button. Small flaws give people a reason to walk away.

  • 02

    A merchant looks through the windshield, not the rear-view mirror.

    Most people decide what to make from last year's sales, so they chase what's over. To Drexler, being a merchant means sensing what will sell next, keeping it focused and on brand, and seeing around corners. Taste, style, fair value and vision are the key ingredients. He wants to be proud of the merchandise, not just sell the most of it.

  • 03

    Find white space so you don't have to fight the competition.

    At Ann Taylor he decided not to sell brands everyone else carried; branded goods end up discounted everywhere, and today you can Google any item and find it cheaper. He worked with manufacturers on an Ann Taylor Studio label. He'd watched Brooks Brothers decline as quality was stripped to hold prices, but it owned its name, so no rival could mark it down.

  • 04

    Bad inventory is rotten fish — get the cash out.

    Taking over Gap, he threw out all the old merchandise and renovated all 430-plus stores together, with no focus groups. The first year was brutal: the stock fell about 50%, and after a year and a half they were sketching a bankruptcy plan in Carmel. He kept relying on his gut and turned it around.

  • 05

    Touch the territory yourself — no filter between you and reality.

    Drexler read in the New York Times that Dayton Hudson's new Target would be 'a cheaper version of Gap.' The week it opened, he flew to the Mall of America without telling anyone. Within five minutes, thinking 'only the paranoid survive', he saw the threat; Old Navy grew from that response and he says it's now about an $11 billion business. Executives in ivory towers lose touch; he goes onto the selling floor and talks to people.

  • 06

    Keep it simple — and name things what they are.

    His first week at Gap he put up 'keep it simple' signs, because people spoke a jargon he couldn't follow. Recently a team called a boxer short a 'short pajama pant' and wanted to change their third-best seller. He polled people: everyone calls it a boxer short, and the name needs no explanation.

  • 07

    Focus groups produce average; vision has to lead.

    Drexler doesn't use them; outliers on both ends rarely do. A friend's 20-page article on how average everything has become rang true. For him the whole business is recognising patterns, then pre-empting them and pushing the team: two years ago 18 painted-dog totes sold out in a day, and he's still pushing personalisation.

  • 08

    Gather ideas relentlessly and act on repeats.

    When he hears something two or three times, he brings it to work. His Monday 'Weekend Update' includes pictures cut from magazines, such as four models in bright hooded sweatshirts. That led to a collaboration idea for a hooded hat, built on the million cashmere hats a year they're famous for. Being famous for something makes you dominant.

  • 09

    The best judge of a boss is the person who works for them.

    Big companies, he says, run on sucking up, because the boss reviews and promotes you. Safe CEO picks with fancy degrees avoid risk; he cares about work history over schools. He can't teach how to spot who's full of it; he'd quietly judge famous retail chiefs as 'not a merchant'.

EXAMPLES

  • 01

    Discovering his father's real pay at 16.

    Sent to bank the payroll at a garment company on West 37th Street, he ducked into a freight entrance and read the stubs. His father, who acted the big shot, was among the lowest-paid. Drexler thinks his ambition came from being his opposite.

  • 02

    Escaping department-store politics for Ann Taylor.

    After 12 years in department stores, starting with a department he ran alone on his second day at Bloomingdale's, he took over Ann Taylor in 1980 with no supervision. He left after four years because his bosses were bureaucrats. He learned early that you must keep competing, relentlessly; many friends who run companies don't.

  • 03

    Fired by Gap, recruited by Steve Jobs.

    Jobs swapped board seats with him. The night before a board meeting, Jobs called to warn he'd be fired. He then helped design the first Apple Store, telling Jobs to build a prototype in a warehouse and strip out clutter. In 18 years no other Gap director called him.

  • 04

    Names found in the wild.

    He spotted 'Old Navy' in neon on a Paris bar on the way to the airport; the board disliked it. He bought the 'Madewell since 1937' name from a friend's old logo, dropped men's, and rehired creative director Somsack to make it work.

  • 05

    Clothes with no expiration date.

    He wears a decades-old shoe style he had remade by the dozen, a 40-year-old scarf, vintage watches and the same blue slub T-shirt daily: a discreet uniform.

OTHER RELEVANT

  • 01

    Rule-breaking beats safe compliance.

    In a shipping room he ticketed coats from a rolling chair and his boss was furious. You can't get fired for following rules, but businesses need people who change them.

  • 02

    Product is about emotion.

    He has 'a love affair' with his companies; retail theatre is just great product that looks like a painting.

  • 03

    Success is impact.

    His best compliment is being called a mensch; former Gap field staff told him he'd made their lives better.