Brian Berger and the trouble with too much choice

Brian Berger had reached the sort of domestic milestone that rarely makes it into a founder’s biography: his wife had thrown away his underwear and socks. He needed replacements. A shopping trip followed, then a much larger undertaking. Plenty of businesses begin with someone spotting a gap in a market. This one also involved a gap in a drawer.

At Bloomingdale’s, the choices seemed to multiply without making the decision easier. A salesperson asked him, “Are you confused yet?” Berger remembered the question years later. Here was an entire retail experience acknowledging its own principal defect. The shopper wanted to buy something familiar and get on with his day. The shop had other plans.

The question that interested Berger was why such ordinary purchases demanded so much effort. Men wore these things constantly. They had preferences, sometimes surprisingly detailed ones. Yet replacing a favorite could feel like starting again. He began thinking about a business that could remember what its customer liked.

The internet executive in the underwear aisle

Berger came to clothing after a career in consumer internet businesses. His background included leadership roles at Excite@Home, WebMD and Comcast. He had studied political science at the University of Colorado and earned an MBA at Columbia. The path supplied experience in reaching people through screens, understanding their behavior and running businesses. It supplied rather less instruction in making waistbands.

That distinction mattered. A digital business can distribute its product without a shipment of fabric arriving anywhere. A clothing company must persuade materials, factories, warehouses and delivery schedules to cooperate. Berger understood one side of the proposed enterprise and had to learn the other. An attractive website would still need something satisfactory to put in the parcel.

He was also starting from an established adult life. He had a family and a career behind him. His later advice to would-be founders was practical: agree on the undertaking with your spouse, understand the financial consequences, then commit. Entrepreneurship, in this telling, involved a household budget as well as an idea. The monthly bills had declined to participate in the romance.

A tote bag had already taught him something

There had been an earlier encounter with physical merchandise. While he was in business school, Berger worked on Breathe, a yoga-bag business involving his wife. It offered a functional bag that could travel into an office without embarrassment. A bag is an agreeable object until a great many bags take up residence at home.

There was packing and shipping to do after work. There was also a commercial lesson. A customer who liked a yoga bag did not necessarily need another one soon. Growth depended on finding another customer, then another. Berger later identified that experience as an influence on the product strategy for Mack Weldon.

Underwear offered a different rhythm. People replace it. If the product pleased them, the same person could return for the same thing. That gave the business a reason to care about the second purchase before it had secured the first. In Berger’s account, an unglamorous category had a useful characteristic: familiarity could become an asset.

Building the shop before opening the door

Berger and co-founder Michael Isaacman launched Mack Weldon in August 2012. They had spent roughly nine months preparing. The identity, the website and the opening range were developed before the public arrived. This was a substantial commitment to an idea whose customers had yet to place an order.

Berger tested his irritation against other people’s experiences. Conversations with friends and peers produced plenty of opinions about socks, T-shirts and underwear. A survey went to 100 people with a request to pass it along. He was investigating a private little subject that became remarkably conversational once somebody raised it.

The launch offered several kinds of essentials rather than a single item. Berger wanted customers to encounter a brand with room to develop. The wager carried costs: multiple products had to be ready together, and inventory required money before it could generate any. He had chosen to give an unfamiliar name a reasonably complete introduction.

The founder’s name isn’t on the label

Mack Weldon sounds like someone you might meet. Berger has explained that Weldon came from an old underwear and sleepwear brand with an abandoned trademark. Adding Mack gave the name a contemporary counterpart. The exercise required a less romantic education in trademark law. A good name also has to be available.

The company’s mark carried another small connection to the merchandise: its M and W could suggest both a crown and the flatlock stitching used in the products. Berger wanted the identity to lead back to what the company made. Even a logo, apparently, could be asked to do a little work.

The details of the clothes had similarly specific assignments. An undershirt could be longer so it stayed tucked in; its neckline could sit lower beneath an open shirt. These are small inconveniences considered closely. They also make a useful test of a founder’s argument. A person wearing the result can decide whether the proposed improvement actually helps.

Success arrived with questions attached

Before launch, Berger arranged outside fulfillment. The yoga bags had given him enough experience of shipping from home. He wanted Mack Weldon’s team available for other work. When the launch attracted attention, that work materialized quickly: questions, calls, crowded inboxes and a website under strain.

He found himself answering customers while at the beach with his children. A buyer interested in an unfamiliar underwear brand might have quite a few things to ask before ordering. Outsourcing the parcels left the founders available for those conversations. In the beginning, customer relationships could be rather literal: Berger on one end of the telephone, somebody considering a purchase on the other.

By August 2017, the business had sold more than a million units and offered nearly 200 styles across a growing range. Those figures describe that point in its history. The more interesting problem for Berger was how to expand without recreating the bewildering assortment that had sent him into business. A company selling simplicity has to keep an eye on its own shelves.

“Growth is important, but … not at any cost.”

Brian Berger, 2018

Two arcade cabinets and a change of venue

In March 2019, Mack Weldon opened its first physical store at Hudson Yards in Manhattan. Inside were product information on tablets, oak display bays and a quick-purchase area for socks and underwear. There were also two arcade cabinets. Even a business devoted to efficient replenishment could allow a small detour.

The store gave Berger a different way to meet the customer. People could see and handle the clothes before deciding, while the website remained available for repeat orders. Earlier selling partnerships had already put the brand beyond its own online shop. Hudson Yards made the physical experiment more visible and gave it a place of its own.

Berger described the location as a place to test and learn. That language suits someone whose earlier career involved digital businesses: open a door, observe what happens, decide what deserves another attempt. His larger ambition required translating the brand into different settings without making the original customer’s errand unnecessarily complicated.

The online founder who wanted more doors

By January 2025, Berger was speaking openly about the difficulty of relying on digital marketing to grow. Wholesale had become a priority. He emphasized longevity and the need for several routes to customers. The ability to keep serving people over time had acquired more weight than the excitement of a young company’s growth curve.

In June 2026, he put his retrospective more plainly: he would have pursued multiple channels, particularly wholesale, much earlier. Shops could introduce the product to people without every encounter beginning in an advertising auction. Selling through another retailer brought its own costs, but it also offered another way to build the business.

That admission gives the origin story an interesting second act. Berger had spotted a problem in a department store, then built an online answer. Experience expanded his view of where the answer belonged. A founder can be right about an unsatisfactory shopping trip and still revise his ideas about distribution. The useful part is being willing to revise them.

Letting the customer decide when

His thinking about loyalty has shifted, too. Berger once placed considerable faith in the right customer data, email strategy and timing. By 2026, he described those capabilities as basic requirements. Customers still replenish when they want to. An email can remind someone about a purchase; it cannot make a drawer empty faster.

That is a revealing concession from an executive trained in digital businesses. The product and the way a brand behaves remain within his influence. The customer’s timetable belongs to the customer. He still believes in understanding the numbers, but the numbers describe people with lives beyond a marketing calendar.

Berger’s ambition has remained recognizable through these adjustments: make everyday clothing better, make buying it easier and build a business that can keep doing both. The work has taken him from internet media to fabric development, from online orders to a shop with arcade games. Somewhere along that route, a reluctant underwear shopper became responsible for giving other shoppers fewer reasons to complain.