What a Handbag Can Teach a Future CEO

Lindsay Wasson Lingle had already studied business when she went to learn about leather. She was starting a handbag company and needed to understand the thing she intended to sell. So she took a sewing class. The point was practical: learn the vocabulary, understand construction, ask better questions. A future chief executive was acquiring an education in seams.

That detail offers a useful way into a career usually introduced through a family name. Her father is Greg Wasson, the former Walgreens chief executive. She is now CEO of WE, the family investment office they helped establish. Yet her own working history includes the particular inconvenience of trying to manufacture a consumer product. A surname cannot stitch a sample.

In 2015, she started Holly & Tanager. A year later, she helped found Wasson Enterprise. Those ventures overlapped, putting her on both sides of a familiar conversation: what an entrepreneur needs and what an investor can actually provide. The handbag business gives that conversation a physical object. You can open a bag, examine its compartments and decide whether the promise survives contact with your belongings.

The connection between those two businesses is an interpretation, rather than a claim that one inevitably produced the other. But it is a useful connection to examine. Lingle’s career keeps returning to the distance between a good idea and a product someone can understand, buy and use. Her responsibilities have widened. The distance remains.

A belt bag with an identity problem

By September 2018, Holly & Tanager had acquired a small linguistic problem. Its founders disliked calling their leather belt bag a fanny pack. The old name summoned a rather different fashion proposition. Their version could also become a clutch or a crossbody bag, with detachable hardware designed to avoid leaving awkward rings on show.

The product was priced at $239 in that period. It accommodated an iPhone 8 Plus, a detail that now dates the design more precisely than any seasonal mood board. Fashion may discuss timelessness; a phone compartment has to negotiate with the hardware of its year. The customer needs her actual phone to fit.

There is a pleasing stubbornness to this category of design. A bag has to look convincing while doing several jobs that are easy to overlook in a photograph. Straps come off. Devices go in. A daytime purchase accompanies its owner into the evening. Each extra use creates another chance for a detail to become irritating.

The belt bag makes a compact case study in the brand’s original proposition: utility had to coexist with appearance. Calling it by a more elegant name could help establish the mood, but the detachable pieces still had to work. Even an accessory enjoys only so much diplomatic immunity.

Thirty things, one very concrete test

Another Holly & Tanager design took the argument in a larger direction. The Professional combined a backpack with a tote format and internal organization. In March 2021, the brand’s Pro Backpack Tote appeared in a travel feature built around fitting 30 items into one bag for a weekend trip. The co-founders were identified as Lingle and Kathryn Rogers.

That is an unusually helpful demonstration for a fashion business. Thirty objects provide a test a reader can picture. The claim invites questions about capacity, access and arrangement. It turns an adjective such as functional into something closer to an exercise: put the things in, then try to find them again.

Travel supplies plenty of opportunities for a product to disappoint. An attractive empty bag is an easy photograph. A loaded one makes a more demanding argument. The packing demonstration placed the emphasis on what the customer could do with the design, giving the product a job with a beginning and an end.

Consider that episode beside the belt bag. One design compressed several ways of carrying into a small accessory; the other organized a weekend’s accumulation. The scale differed, but both asked the buyer to imagine a sequence of use. That way of presenting a product would remain relevant as Lingle’s work moved into businesses whose machinery was considerably less portable.

The résumé has a retail backbone

Lingle graduated from Purdue University with a BA in public relations in 2011 and earned her MBA from Xavier University in 2015. Before WE, she worked in sales and marketing at Kao USA. Her professional grounding came through consumer brands, where the relationship among product, retailer and customer is part of the daily work.

The sequence matters. She entered entrepreneurship with experience inside an established consumer products company. She then encountered the less orderly world of starting her own line. Later, at WE, her work extended to marketing for partner companies, including plastics recycling business PureCycle Technologies and packaging company AeroFlexx. The products changed; the need to explain them remained.

WE credits her with creating its brand and developing the marketing services it offers partners. That work sits between an investor’s decision to support a business and the business’s need to reach an audience. A portfolio company may have technical expertise without an equally developed way to communicate what it makes.

This is one reason marketing belongs in her leadership story. In this setting, it involves finding language and a presentation that fit the product and its intended audience. A handbag customer, a packaging buyer and a potential business partner bring different questions. Experience with one does not automatically answer the others. It does provide practice in noticing that the questions differ.

A colleague remembers the invitation

Kathryn Rogers offers another view of Lingle’s working life. Their connection began at Kao USA, where Rogers stepped into an internship position Lingle had previously held. Rogers later described Lingle as a mentor who helped her understand consumer products and retail, encouraged her curiosity and challenged her to keep developing.

Rogers also credited Lingle with inviting her into WE nearly a decade before that reflection. The relationship joins several parts of the story: an established employer, an early professional opportunity and a later place on a growing team. It gives the otherwise broad language of investing in people a specific pair of names.

The distinction between a colleague’s recollection and a universal character verdict matters. One person’s experience cannot establish how every relationship works. It can show what endured in this one. Rogers remembered guidance, belief in her potential and an invitation that changed where she worked. Those are concrete forms of professional support.

For Lingle, that connection also complicates the solitary-founder version of entrepreneurship. Her career includes relatives, business partners and colleagues whose histories overlap across organizations. Teams accumulate through those encounters. A person who once explains a category or an industry may later help explain the next company. The organization grows partly through relationships that already have some working history behind them.

Four founders, then a wider assignment

Wasson Enterprise began in Chicago in 2016, founded by Greg and Kim Wasson, Lindsay Wasson Lingle and Mike Lingle. In 2017 it partnered with Innventure and began supporting PureCycle Technologies. In 2018 it formed WE People Solutions to provide human resources services for partners that lacked those resources. The firm gradually gave its idea of partnership an operating structure.

Lingle became co-president alongside Greg in 2021. The title placed her in broader leadership after her earlier work shaping the firm’s marketing capabilities. The progression is visible across several years, rather than appearing only at the moment a new chief executive was announced.

By October 2025, Greg publicly welcomed her move into the CEO role. Her own announcement also named a wider leadership group: Michael Lingle as chief strategy officer, Gerald Muizelaar as chief financial officer, Josh Salyer as chief people officer and Trey Gill as senior director of investments. The announcement described an organization assigning responsibilities across a team.

Her present remit includes company strategy, partner exploration and investment opportunities. WE describes the fit it seeks in terms of shared values and opportunities where its team can add value. That is a consequential filter for a family office: each prospective relationship makes a claim on attention as well as money. Selecting a partner also means considering the work that will follow.

Patience gets a place in the ledger

At the end of 2025, Lingle’s year-end message gave the leadership transition a less ceremonial accompaniment. She described a year with constraints, a reliance on the team and a continued focus on partnerships. She also wrote that initiatives nurtured for nearly a decade were coming to fruition. Patience was the lesson she singled out.

That account is more useful than a smooth succession narrative. It places the new title beside the ordinary limits of running an organization. Resources have to be allocated. Existing relationships require attention. Some work takes years before it produces the result people hoped for at the beginning. An appointment does not reset those clocks.

As WE marked ten years in 2026, its reflections returned to building alongside founders and operators. Lingle had participated from the start, moving from the firm’s formative work through co-presidency into the CEO position. The anniversary therefore described a period she had worked through, with changes in her own responsibilities along the way.

Her earlier handbag launch still supplies a concise counterweight to the institutional language. “I am proud that we launched,” she said in 2018. There is room in that sentence for preparation, doubt and the decision to put something into customers’ hands. The sewing class belongs to the same practical history. Before a product could make its promises, somebody had to learn how it was put together.

“I am proud that we launched.”

Lindsay Lingle · 2018