Steven Szaronos and the good sense to change his mind

Steven Szaronos and Rishi Prabhu had spent the summer working on an advertising idea that required strangers to scan QR codes. Then they considered the strangers. Walking around New York, they could not remember seeing anyone except themselves do the thing their business depended on. There were advertisements all over the city. The missing ingredient was somebody interested enough to point a phone at one.

This was 2011. They were in the first class at Entrepreneurs Roundtable Accelerator, with demo day approaching. Szaronos recalled the admission they made to the program’s organizers: “We don’t believe in this idea anymore.” There is a certain economy to that sentence. Months of work, reduced to seven words.

The organizers accepted the change of heart. They also expected something to present. The pair still had a deadline, a partnership and a chance to build a business. What they needed was a different reason for customers to care.

The education of an operator

Szaronos’s route to that awkward conversation ran through more conventional institutions. His career included consulting at Deloitte and a strategic project-management role in operations at Callaway Golf. He went to Northwestern’s Kellogg School of Management in 2009, completing his MBA in 2011. A summer role at Chegg and a place in Kellogg’s winter 2010 Venture Lab, with sponsor 12AFund, added other ways to see a business taking shape.

Those experiences belong in the picture because the company he eventually built would have to do two things at once. It would need to make unfamiliar products appealing. It would also need to buy them, keep track of them and deliver them. Taste might get a customer’s attention. Operations would have to keep the appointment.

At Kellogg, he met Prabhu, who became his co-founder. Early accounts divided their responsibilities in revealing fashion: Prabhu handled technology and product selection; Szaronos handled operations. The appealing object and the practical arrangement for getting it into someone’s hands had separate advocates.

For Szaronos, business school also made entrepreneurship feel accessible. “I hadn’t been exposed to the startup scene,” he said. The distance between studying companies and starting one had become short enough to cross. He crossed it with a classmate, then found that the first idea did not justify the journey.

One hundred parcels, then pallets

The replacement became Bespoke Post, a business introducing men to selected goods through monthly shipments. In November 2011, its first packages went to 100 recipients. The founders had $10,000 remaining from the accelerator’s initial $25,000. Their first months included overnight packing sessions. A subscription sounds pleasantly automatic until you meet the people doing the subscribing company’s work.

The arrival of pallets eventually made the limits of packing everything themselves apparent. This is a useful early milestone: the business had become physically too much for its original arrangement. Growth had arrived in a form that required floor space.

Partnerships with American Airlines, Details magazine and Diageo helped the young company find an audience. On the supplier side, Sempli, a maker of barware and lighting, saw a route to people who might otherwise never encounter its products. A selected glass could do two jobs: complete a box and introduce a maker.

That second job gave the company a reason to exist beyond the convenience of a recurring delivery. An unknown brand needs attention. A customer needs a reason to give it. Bespoke Post placed itself between them, offering a selection that could make the introduction easier.

The useful thing about a no

Szaronos’s explanation of the customer was refreshingly unromantic. Men could enjoy discovering products and experiences while having little appetite for searching through shops. “They just don’t want to do all the work,” he said in 2013. The company could do some of that work for them.

The observation leaves room for curiosity without demanding that shopping become a hobby. Somebody might enjoy a better cocktail glass or a useful travel accessory and still prefer to spend Saturday doing almost anything besides comparing them. The retailer’s assignment is to narrow the field without making the customer feel cornered.

Members could pass on a month after seeing the preview. That detail matters. A selected product is still a suggestion, and suggestions become more useful when the recipient can refuse them. The option to skip also gives a retailer a different kind of information from a purchase.

“They just don’t want to do all the work.”

Steven Szaronos, on product discovery, 2013

A sale tells you that something found a buyer. A skipped selection raises a question: wrong product, wrong timing, wrong person? It does not supply the whole answer. But it is a reason to keep asking, rather than to assume that every quiet customer wants the same thing.

Szaronos was discussing member preferences early in the company’s life. Where people lived and what they accepted or declined could help the team understand the audience beyond a broad demographic description. A man who enjoys cooking and a man who enjoys camping may both appreciate good equipment. They do not necessarily need the same box.

In 2013, he also described demand from Canadian customers strong enough to bring forward an expansion there. Even the geography could follow a response from the audience. The company was selling discovery, while doing some discovering of its own.

When the numbers caught up

By January 2021, Szaronos was discussing a different scale of problems on the Modern CTO podcast: technology as an organization grows, and how to process feedback and advice while moving the business forward. The episode’s introduction described a company that had delivered to more than half a million customers across the United States and Canada.

In October that year, Bespoke Post announced a $40 million Series B led by NewSpring. The announcement identified Szaronos and Prabhu as co-CEOs. It reported more than 300,000 active members and an 85% revenue increase in 2020. The financing followed about $8 million raised previously.

Szaronos connected a more personalized experience with a 35% rise in revenue per member over the preceding two years. The stated plan was to use customer insights to identify emerging brands and put more relevant products in front of people. These are dated company figures, useful for understanding the business at that moment.

There is an operational question hiding inside the appealing word “personalized.” Once a retailer carries more products and serves more people, how does it preserve the feeling that a suggestion was made with someone in mind? More stock creates more possibilities. It also creates more ways to show a customer something irrelevant.

The funding made that problem larger and better resourced. The underlying task remained recognizable: learn enough about the buyer to make a worthwhile introduction.

The customer wanted another door

Bespoke Post opened its shop in 2014, allowing purchases without a subscription. By 2023, the company was investing more effort there. Customers who discovered a brand through a box wanted access to more of its products. Other shoppers wanted to buy without a monthly arrangement.

That is a flattering complication for a business built on introductions. The introduction succeeds, and the customer asks for a longer conversation. The original box can only contain so much. The website can offer another route.

The change also has a physical dimension. In 2023, shop orders to suppliers could range from hundreds to thousands of units, while orders for boxes could run from 5,000 to 50,000. Selection was a purchasing decision with consequences for inventory, rather than simply a list of objects that looked good together.

By October 2025, Prabhu described an increasing emphasis on individual retail purchases, with membership still available. The audience had grown older and more affluent. The assortment mixed smaller brands, familiar names and products developed within the business. Different customers, and different moments in the same customer’s life, called for different prices.

A month later, owned brands were reported to contribute more than half of sales. Line of Trade and Halfday were among them. The enterprise Szaronos helped start was now making products as well as choosing them.

Keep the question, change the container

Today, Bespoke Post’s shelves include its James Dean Estate collaboration alongside its wider assortment. Its website reports more than $220 million spent with small brands over the past decade. The accumulated purchasing is another way to see the company’s role: each introduction rests on an actual order placed with a supplier.

Szaronos’s story is most revealing when kept close to that practical work. A career in operations. A classmate who became a partner. A summer spent on an idea they stopped believing in. One hundred shipments. Then a business large enough to require another way of serving its customers.

The first change of mind remains the telling episode. The founders had a deadline and work already invested. They still allowed what they observed to alter what they would do next. Bespoke Post has since changed its format again. The question behind the work continues to be worth asking: what would this customer be pleased to discover?