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How a celebrity CEO’s rule of fear helped bring down hot Singapore start-up Zilingo

Inside the company, former employees paint a picture of a boss who ruled by fear. She allegedly told some staff they would have no second chance in the start-up industry because of her powerful connections. She would publicly shame employees and declare that she had to do everything herself to save the company, one person said. Another described her as a narcissist who would throw anyone under the bus if it meant saving her own reputation from her.

Asked in an interview in Singapore before she was fired about the culture under her leadership, Ms Bose uncharacteristically paused and stared out of the window as the sun set over the city.

“I was 23 when I started the company,” she said eventually. “I liked having control at the beginning. Of course, I made mistakes and learned from them. By the time we got to the stage where we had all these senior people, I don’t think I was a control freak.”

In her most recent interview with Bloomberg in July, Ms Bose reiterated that she has not done anything wrong. “I’m going to be a lot calmer, a lot more empathetic and understanding of how people work together. That has been a big learning for me. Managing people, managing relationships, managing communications – I think all of this is coming down to that,” she said.

By November 2020, Zilingo had barely enough cash to last a month. A group of existing investors, including Sequoia, EDBI, Sofina, Temasek and SIG, stepped in to rescue the company by purchasing US$25 million of convertible notes.

In January 2021, Mr Singh and Ms Bose met at the Four Seasons Hotel’s alfresco cafe as they did from time to time to talk shop. Mr Singh suggested that Ms Bose considered stepping aside. He said Mr Ananth Narayanan, founder of brand-building service Mensa Brands and former CEO of fashion platform Myntra, could be a potential successor. The two men had met recently and, when Mr Narayanan said he was looking for a new opportunity, Mr Singh had thought of Zilingo.

Ms Bose was shocked. “Not yet,” she said.

She went home and, that night, sent a series of emotional texts to Mr Singh, saying his suggestion was a gender-related issue and pouring her heart out. She said her departure from her would make her look bad, as though the firm needed to be saved by someone else. Mr Singh said it was just a preliminary idea and there was no need to discuss it again. He urged her instead to focus on improving metrics, finding a new CFO and fund raising, according to people familiar with the meeting and texts seen by Bloomberg.

Ms Bose ended the chat by saying they should work together towards the best possible outcome, and Mr Singh replied with two thumbs-up emojis. It was 2.29am.

The mounting pressure was also testing the relationship between Ms Bose and co-founder Mr Kapoor, the chief technology officer. They had clashed over the future of the company the previous month when the company was scrambling to stay afloat.

“I am scared honestly that we will not hit our goals,” she texted Mr Kapoor several hours after the chat with Mr Singh. “When something is wrong, the blame falls on me, but everyone’s there to take credit for the good,” she wrote.

“I don’t like being hated for busting my ass at all,” she added.

Ms Bose spent most of the year trying to pull in more funds. In July 2021, the company took mezzanine debt of US$40 million from Indies Capital Partners and Varde Partners, but subsequent efforts to raise money from private equity and venture capital firms failed. One issue was a concern from potential investors that users were making fake transactions in key markets to bilk Zilingo’s subsidies. Executives from two firms told Bloomberg News that they decided not to back Zilingo after they found evidence of merchant fraud in Indonesia, the country that accounted for more than half of Zilingo’s gross merchandise volume in financial year 2021.

There was no suggestion that Zilingo was involved in the suspected fake transactions. Some existing investors, including Burda Principal Investments, Temasek and Sofina, questioned Ms Bose about the company’s unaudited financial reports, according to people familiar with the matter. But Ms Bose was providing monthly financial updates to the board, and they were lenient as Zilingo was busy with fund raising at the time, one of the people said.

In March this year, Ms Bose received an ominous text on her phone: “Storm is coming your way.”

A few days later, she was asked to join a meeting with investors at Burda’s shophouse office in Singapore’s Boat Quay, according to people familiar with the details of the meeting. There, Mr Singh and the two other shareholders dealt her a stunner. They said Zilingo’s board had received complaints about alleged mismanagement and financial misrepresentation of her and they were suspending her during an investigation. Mr Singh urged her to be cooperative.

“We just want to save the company,” he said, according to one of the people.

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