Rishi Prabhu and the useful art of changing your mind

Six boxes into Bespoke Post, Rishi Prabhu decided he had exhausted the possibilities. He was walking with his co-founder, Steve Szaronos, near Astor Place in New York’s East Village. There could surely be only so many things worth putting in a box. Szaronos persuaded him to keep going. Years later, Prabhu could tell the story with the agreeable advantage of having been wrong.

The scene offers a useful introduction to someone whose work involves choosing things. A curator needs opinions. A founder needs enough conviction to act on them. Prabhu has also had to develop the ability to revise an opinion without treating the revision as a personal catastrophe. His career contains several consequential changes of mind, beginning with the business that never became Bespoke Post.

Today, his company sells apparel, travel bags, kitchen equipment and other goods through a shop and an optional membership. It also builds brands of its own. The cardboard box remains part of the business, but it no longer describes the whole assignment. Prabhu’s recurring job has been to work out what deserves to survive each change.

The idea they left behind

Prabhu met Szaronos at Northwestern’s Kellogg School of Management in 2009. His education already included computer science and mathematics at New York University, followed by a master’s in computer science. His career had taken him through consulting and roles at Google and Groupon. The future retailer arrived with a technical background as well as an interest in what people might enjoy buying.

The pair entered New York’s Entrepreneurs Roundtable Accelerator with Nabfly, an advertising concept involving QR codes. They had put work into it. There was an app. There was a name. Those are reassuring possessions when a business is young, even if neither settles the question of whether anyone wants the business.

As the accelerator’s presentation day approached, they abandoned the idea. The replacement would help men discover products, drawing on Prabhu’s interest in selection and Szaronos’s supply-chain experience. Leaving Nabfly meant giving up the comfort of work already completed. It also let them tackle a problem they understood more personally.

The early operation was tangible in ways an advertising pitch could never be. In November 2011, they shipped their first boxes to 100 recipients, using $10,000 remaining from their accelerator funding. Packing meant late nights. Eventually, incoming pallets made the limits of doing it themselves fairly obvious. An idea had become something that occupied floor space.

A vote against his own taste

There is something appealingly unlikely about a computer-science graduate becoming responsible for product selection. Yet the two activities can meet in the same question: what happens when another person actually uses this? An object can look promising in a meeting and become considerably less persuasive in someone’s kitchen.

Bespoke Post developed a process for asking customers about proposed products. Its Field Research tool put concepts in front of members and collected reactions. Those answers could inform both whether a product went ahead and which customers might receive it. Prabhu described the exchange as an ongoing conversation, rather than a single recommendation made at signup.

For a founder with a point of view, that arrangement requires restraint. A strong recommendation is still only one side of an exchange. The buyer brings a different set of possessions, habits and reasons for saying no. Customer feedback makes room for those differences before an enthusiastic meeting turns into unsold stock.

The interesting skill here is keeping enough judgment to offer a coherent selection while admitting that taste does not confer ownership of the customer’s decision. A shop without opinions is a warehouse with better lighting. A shop that cannot hear disagreement risks becoming a very elaborate display of its founder’s preferences.

A partner for the doubtful afternoons

Szaronos’s contribution extends beyond getting goods delivered. In discussing their partnership, the founders have described the familiarity that comes from working together for years: understanding each other’s reactions, recognizing differences in personality, and sharing an intended destination even when they argue about the route. Prabhu has spoken candidly about those disagreements.

That makes the Astor Place episode more useful than a tidy story about perseverance. The person announcing that the ideas were finished had someone beside him who could challenge the conclusion. Business partnerships are often explained through complementary résumés. Sometimes their value appears in a much smaller unit: one conversation on a bad afternoon.

“There are no more box ideas.”Rishi Prabhu, recalling an early conversation with Steve Szaronos in 2021

His public manner also leaves space for a joke. In a recruiting post, he described marketing leader Alvaro De La Rocha as smart, thoughtful and “moderately humorous.” Announcements about new brands give credit to the team. The effect is more colleague than distant tastemaker, someone willing to put another person’s name beside the work.

The company developed an appropriately practical introduction for new colleagues. A cocktail-making exercise for interns in 2013 became a ritual for new hires. Each person made something for the team. Whatever one thinks of the drink, it is a compact assignment: choose, make, present, discover what the room thinks. Even the social ritual had a little product development in it.

The money comes after the boxes

By October 2021, Bespoke Post was announcing a $40 million Series B led by NewSpring. The company identified Prabhu and Szaronos as co-CEOs and reported more than 300,000 active members. It said revenue had increased 85 percent in 2020. The announcement also emphasized the roughly $8 million raised before that round and a focus on profitable growth.

The distinction between money raised and a business built matters. An investment round supplies resources. Members supply evidence that people are prepared to keep buying. Neither number by itself tells the whole story of what someone has created. Together, these figures marked the distance from those first packing nights to an operation capable of attracting a substantial growth investment.

Prabhu’s stated priorities included finding more small brands. Funding would also support retail partnerships and data science. Those ambitions connect the visible and less visible parts of his work: choosing merchandise people might care about, then improving the machinery that helps it reach an interested customer.

The customer walks past the box

Growth brought a different problem. Someone who liked an introduction to a brand might want more than the monthly selection contained. Someone else might want to buy a product without becoming a member at all. By June 2023, Prabhu was describing a shift toward a destination for discovering products, with an expanded open Shop.

The practical change was straightforward: let the customer continue shopping. The implication for the founder was larger. If the original format had done its job, it might have created demand that the format itself could no longer satisfy. The box could open a relationship and still become too small to contain it.

In October 2025, Prabhu described one-off purchases as a growing opportunity. The assortment mixed small brands, established names and the company’s own products. He also talked about customers getting older and more affluent, and the importance of offering appealing products at different price points. The imagined buyer had acquired a little history along with the retailer.

That is an ordinary fact of a long-lived business, easily overlooked in a launch story. The customer keeps living. Their budget changes. Their home fills up. What once felt like an invitation can begin to feel like a restriction. Listening has to continue after the first sale, because the person receiving the recommendation is allowed to change too.

Making something worth keeping

Prabhu’s next assignment has included helping build brands, rather than only selecting them. Halfday makes travel bags. Line of Trade covers apparel and bags. Fieldworth adds another menswear identity. By November 2025, Bespoke Post’s owned brands accounted for more than half of its sales, with the portfolio having expanded from two brands to five.

He has described the aim as creating distinct identities that could live within the retailer or beyond it. That is a more demanding ambition than attaching a store’s name to a cheaper substitute. A brand needs a reason for someone to seek it out again, even when the original introduction is long forgotten.

A September 2026 project brought that ambition into sharper focus. Bespoke Post announced a collection developed with the James Dean estate under Fieldworth, working with stylist Mark Avery and designer Andrew Livingston. The opening collection included more than 20 pieces, with partners including Stetson and Schott NYC. Prabhu emphasized the endurance of Dean’s clothes and the value of products people would keep.

The choice fits the recurring question in his career: which part of a good idea should last? The first advertising concept went. The monthly box stayed, with more ways to shop around it. Curation grew into creating products. Each change asked him to reconsider the container while preserving a reason for the customer to care.

Back near Astor Place, six boxes had seemed like the end of the available ideas. It is a pleasingly modest beginning for a retail career: a person with taste, briefly convinced he had used it all up, and a friend who thought there might be something left. There was. The harder work was learning how to keep looking.