Mr Gupta is a big admirer of Mr Lee Kuan Yew and spoke candidly about three memorable meetings with Singapore’s founding father.
“The person who inspired me the most, I never worked with. It was Lee Kuan Yew. I was a big fan of what he was able to do to this tiny country.”
He read Mr Lee’s books and was struck by how someone with a sense of purpose and a willingness to think differently could achieve such great success.
“I asked him cheekily, ‘Why don’t you go and run my country, India?’” Mr Gupta recalled with a smile of his first meeting with Mr Lee. “He thought and then he laughed and said, ‘Even God can’t run your country!’”
That encounter set the tone for what would be a profound relationship built on respect. Their second meeting, just after the 2011 Singapore elections, addressed a more serious issue – immigration.
“I asked him about all the noise surrounding immigration,” Mr Gupta said. “And he told me, ‘If Singapore does not stay open, we are dead. He said, this is what makes America different.’”
When Mr Gupta pressed further, asking why the government didn’t take a more vocal stance, Mr Lee gave a sharp response.
“He thumped the table and said, ‘It’s not my government. It’s my son’s government.”
But it was their final meeting that Mr Gupta recalls as most revealing. He asked Mr Lee what he would have done differently with hindsight.
“He said, ‘I would have brought Formula One to Singapore sooner.’ I was surprised. Of all things?” Mr Gupta said.
Mr Lee then explained that he had initially rejected F1, thinking it had no place in Singapore. But he later realised he was wrong and that building a country wasn’t just about infrastructure but about focusing on other aspects too.
Though banking was his calling, Mr Gupta had a brief, surreal taste of celebrity. While Shah Rukh Khan and Priyanka Chopra were filming Don 2 in Kuala Lumpur, Mr Gupta – then the Citibank country head in Malaysia – was invited to the shoot.
“We talked for a bit – he’s five years younger than me and from my school, St Columba’s in Delhi,” Mr Gupta said. “But soon, there were two Malaysian Indian guys there.”
“So Shah Rukh said, okay, let me just give them the autograph, then we can continue the conversation. So they come, they walk past Shah Rukh Khan, come to me and say, Mr Piyush, can we get a picture?”
“I call it my Andy Warhol moment, you know, 15 minutes of fame,” he said with a laugh.
He also found inspiration in Alibaba’s Jack Ma.
“I only met him once, but I got great ideas from that one conversation. It helped us shape our approach to financial services.”
Mr Gupta is a firm believer in the value of institutional memory. Early in his DBS tenure, he reached out to Mr S. Dhanabalan, former DBS chairman and one of Singapore’s most respected public servants.
“Dhana was instrumental in shaping DBS. I met him a few times over lunch to understand the psyche and history of the bank,” Mr Gupta said.
“I wanted to learn how the country thought about DBS and how the bank thought about itself.”
He also sought advice from Mr S. Chandra Das and other senior members of Singapore’s Indian community.
“I wanted to understand the cultural and political landscape. How do I navigate as an Indian in Singapore? What should I be mindful of?”
