Heading up a startup, as opposed to a large corporation, has its pros and cons, said Mickey Drexler, the former CEO and chairman of J.Crew Group and CEO of Gap Inc. Today, Drexler is the executive chairman of Alex Mill. The fashion brand was founded in 2012 by his son, Alex Drexler, and Somsack Sikhounmuong, who formerly led design at Madewell. "When I started Old Navy, I had the bank of Gap to fund it… Then I started Madewell, which I owned the name of and sold to J.Crew, and [it was] the same thing: I had the bank of J.Crew,” Drexler said on the latest Glossy Podcast. “But with this business, there are no big banks. There's my bank and my son's bank; we don't have any investors other than us. And it's much more difficult.” Still, he said, “I love it. Because you're involved in every decision. You're looking at everything in detail. And you're micromanaging like crazy, which I like to do.” Rather than investors, Alex Mill has an "unofficial" board of directors, largely made up of people who work in the industry. “Understanding the fashion business is a rarity if you're not in it,” he said. While Alex Mill is not yet profitable, Drexler said business is “seven times what it was two and a half years ago.” And, he said, the company is getting ready to “step on the gas,” in terms of accelerating its growth. That includes linking with a marketing agency; adding to the company’s one store, in NYC’s SoHo; getting inventory right and continuing to sell at full price. “If we weren't direct-to-consumer, the goods we sell would all be marked down somewhere,” he said. “The most successful department store today is TJ Maxx.”

When Karla Welch and Clea O’Hana launched fashion styling app Wishi in 2019, the idea was to democratize the fashion styling experience, which is usually reserved for celebs. “Karla’s dream was to bring styling to everyone,” O’Hana said, on the latest Glossy Podcast. “It’s a great partnership -- because I had the technology and the business idea, but I didn’t have the styling or the fashion part of it…[Together] we’re replicating the relationship that she has with her clients, online.”  Welch has 20 years of experience as a stylist; her clients to date have included Justin Bieber, Tracee Ellis Ross and Karlie Kloss, among others. Meanwhile, O’Hana’s background is in business and finance, though she’s worked in merchandising for fashion companies including Net-a-Porter and Belstaff.  In February, Wishi secured a partnership with Farfetch, granting the retailer's high-spend loyalty members access to Wishi’s styling services. (Typically, clients pay Wishi $40 to be styled in two looks and $90 for five looks -- stylists are not paid on commission.) Thus far, the partnership has revealed some interesting data points. For one, customers who take advantage of the service are returning fewer items.  “When you're shopping for yourself, and you don't have the eye or the confidence, or you're not sure [about] the fit, you overbuy, and then you send things back,” said Welch. “It’s a huge waste environmentally, and it's really damaging to a lot of businesses.” Wishi is getting the word out about its services via its Style Council of stylists, who promote their bookings. It also invests in digital marketing and Google search. “[However] people are looking for this service now; there's really a lot of demand,” said O’Hana. “We don't have any problem marketing it.”