After being let go as executive chairman of Men’s Warehouse, the company he founded, in 2013, George Zimmer founded Generation Tux a year later. Generation Tux offers convenient and low-stress suit rental services exclusively online. “In lieu of going [to the] store, there are many advantages through Generation Tux, particularly for the bride who has so much going on around her wedding. Gen Tux is a load off her mind,” said Zimmer on the latest episode of the Glossy Podcast.  With 50 years of experience in the suit industry, Zimmer understands the desire to order your own wedding tuxedo from the comfort of your living room. Generation Tux's concise shipping timeline — it delivers customers’ suits three weeks before an event — is also advantageous since it allows for last-minute changes.  But even with the online spending spree of the pandemic, the company has faced challenges. When the pandemic first hit, Generation Tux temporarily shut down until it received government aid. Two years later, it is reaping the benefits of the pandemic’s demand for accessible online fashion, with yearly revenue of $5 million. 

With economic and consumer trends constantly in flux, Imaginary Ventures co-founder and managing partner Nick Brown wants to ensure his VC firm stays ahead of the curve. Brown created the venture capital firm alongside Net-a-Porter founder Natalie Massenet in 2018. It is now one of the largest VC funds sitting at the intersection of technology and retail. The company's portfolio includes well-known brands, platforms and founders, including Glossier, Skims, Everlane and Farfetch. The firm has grown funds under its management to $1 billion. In April, it announced its third fund, of $500 million, across late- and early-stage businesses. According to Brown, part of Imaginary's success has been its ability to find the diamond startup with the potential for global reach. "Our approach to investing in brands was always brand lead and product lead," Brown shared on the latest episode of the Glossy Podcast. Brown added that the company prioritizes brands at the forefront of innovation in technology and those that can adjust to an ever-changing ecosystem. While Imaginary has found success in investing in later-stage businesses, it also values early-stage brands and founders shaping the future of the consumer experience. "If you're an early-stage founder, it's less about the detail of [a 5-year plan] and more about the vision of how you're going to hit scale, because that's the hardest thing for everybody. I would say that, for every 20, 30, 40 companies we see, [only] one of them has the ability to hit that [$100 million] kind of scale. So you want to be really thoughtful and really confident in your articulation of how you achieve that," said Brown.