A millionaire tech mogul has launched an unlikely bid for Nancy Pelosi‘s coveted congressional seat, but the stacked primary has proved challenging as he reportedly struggles to resonate with constituents. 

Saikat Chakrabarti, 40, initially threw his hat in the ring against the former Speaker of the House, until Pelosi announced last November that she would not seek re-election. 

Now Chakrabarti faces two challengers for the open seat, both of whom have fostered careers in local San Francisco politics. 

Meanwhile, Chakrabarti has ruffled some feathers after he received the endorsement of famous drag queen Peaches earlier this week. 

The two shared a video on Thursday, announcing a joint Get Out the Vote and drag show event called Drag Me to Vote on April 4. 

In another video, Peaches explained why she endorsed Chakrabarti, writing on Instagram: ‘San Francisco has a rare opportunity right now. 

‘This congressional race will decide whether we keep accepting business as usual or whether we send someone to Washington willing to actually challenge the systems that created the crises we’re living through.’

The endorsement received some backlash online, with commenters accusing Chakrabarti of not focusing on the issues at hand affecting locals in the Bay Area.

‘Dude what is this? no one is forcing you to do this? just focus on affordability please,’ one commented.

‘Nothing like being dragged to back a billionaire when there is another option who is not a billionaire or a billionaire’s bro. Vote Connie Chan. Also, why aren’t y’all supporting the woman of color whose running who is also backed by labor? What is your class analysis here?’ another wrote.

‘The guy has zero track record in San Francisco. Bad choice, Peaches,’ a third added. 

Chakrabarti has faced criticism in his campaign for his wealth, lack of political experience and time spent in San Francisco. 

The San Francisco Chronicle observed Chakrabarti and his challengers, City Supervisor Connie Chan and State Senator Scott Wiener, last week. 

The Chronicle noted that both Chan and Chakrabarti frequently came across voters who brought up Wiener. 

‘You got tough competition in this neighborhood. Scott Wiener is pretty well liked and was responsive as a supervisor,’ one voter reportedly told Chakrabarti. 

‘Chakrabarti may be chummy with the nation’s leading progressives, but relatively few San Francisco voters know him,’ the Chronicle observed. 

‘So when Chakrabarti knocked on a voter’s door to ask for their support on a Saturday afternoon in January, he started by name-checking people they might have heard of before.’

The Chronicle also noted that Chakrabarti encountered several voters who said they would vote for Wiener because they knew him personally. 

Another voter said they appreciated Chakrabarti’s experience but were ‘uncomfortable’ voting for him since he spent time away from San Francisco. 

Unlike his challengers, Chakrabarti lacks political experience in the city he is running to represent. 

He became a tech millionaire for his work as a software engineer at the payment processing company, Stripe. 

Chakrabarti then pivoted from technology to politics, working on Senator Bernie Sanders’ 2016 presidential campaign and serving as chief of staff to Representative Alexandria Ocasio-Cortez. 

Wiener capitalized on Chakrabarti’s wealth and inexperience in San Francisco, launching an attack ad criticizing him for using his money to fund his campaign while touting that he does not take corporate funds. 

‘My opponent is using his vast personal wealth to try to buy a seat in Congress. I’m not worth hundreds of millions like he is, but what I do have is decades of real experience delivering for San Francisco,’ Wiener wrote on social media earlier this month.

‘Being hyper-rich can buy you a lot of things, but it shouldn’t be able to buy you an election.’

Chakrabarti has used his unique experience as a selling point in his campaign, claiming he will bring a new voice to Congress, one not beholden to years of political influence. 

Some young progressives have championed his campaign, with one writing on Peaches’ endorsement video: ‘Thank you. Just because we all know Scott doesn’t mean we want to send him to Congress on our behalf.’

‘Agree peaches! Saikat isn’t a billionaires puppet like some of the other contenders running for the seat,’ another added. 

The Daily Mail has reached out to Chakrabarti’s campaign for comment.