The Singaporean comedian in Silicon Valley making punchlines out of failures
A Meta programme manager by day and stand-up comic by night, San Francisco-based Elisha Tan tells CNA TODAY how she uses humour to make sense of setbacks and connect with strangers across the world.
Ms Elisha Tan performs at Punch Line San Francisco, one of the city's most established comedy clubs, in 2024. Photo: Elisha Tan)
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Like secret pop superstar Hannah Montana, Ms Elisha Tan leads a double life.
She spends her days on her laptop in her San Francisco apartment, toggling between emails and meetings as a developer programmes manager at Meta. At night, the 38-year-old steps onto spotlit stages in dimly lit bars, facing a room of strangers armed with nothing but a microphone and her wits, hoping to make them laugh.
Being a stand-up comedian is not the most natural job for Singaporeans, who often have a reputation for being strait-laced and rule-abiding.
Ms Tan recalled spending much of her childhood and teen years in a rigid classroom environment, where cracking jokes was often quickly condemned as disruptiveness.
"Because of that 'naughty' label, many of us learn to suppress our funny sides," she said, adding that being funny was also typically seen as "more acceptable" in boys than in girls.
"I was called 'chor lor' (Hokkien for rough or uncouth) and told I was 'too much' many times growing up."
The way she sees it, adults and authority figures in Singapore tend to classify class clowns as problem kids to be taken in hand.
"I don’t think we've historically nurtured comedic voices or really valued comedy as a culture, especially for women."
For what it's worth, her parents back in Singapore are supportive of her comedy pursuits – her mother even in ushered audience members to tables and checked tickets for one of her Singapore shows in 2025.
"Most of my shows are not glamorous," Ms Tan told me matter-of-factly, her rounded features prominent on our video call behind the black thin frames of her glasses, thanks to the green headband pulling her hair back.
She typically performs to audiences of about 20 to 30 people in small bars. Depending on the venue and the night, that number can sometimes drop to five or 10. But for now, that's enough for her.
"To me, (performing stand-up is) about mastery and refining. The craft is all about iteration. If there are just two people and I can make them laugh, that is data to me. That's still valuable to me."
Ms Tan performs about six to seven times each week. It's tiring, she said, but it's worth it.
"It's like creating joy out of nothing. I just turn a bunch of words into something that makes people laugh and when they laugh, I feel happy too.
"That's why I am single. I haven't met anyone more interesting than the work I do, and I have no time."
Right now, she is preparing for one of her most ambitious comedy endeavours yet: a one-hour, one-woman show set to run at the upcoming Hollywood Fringe in Los Angeles this June.
The show traces the many ups and downs of Ms Tan's career, a career that has seen her fail over and over in ways that might make any other born-and-bred Singaporean cringe or even recoil in dismay.
A STRING OF FAILURES
One of Ms Tan's earliest lessons in life about failure came in secondary school, where she had a rude awakening: Doing everything "right" might not offer her the rewards she had always thought it would.
At 14, she was made a prefect and tasked with monitoring her peers for rule flouting. As instructed, she reported infractions such as inappropriate skirt lengths without a second thought.
She ended up being bullied relentlessly by classmates for carrying out duties such as these.
"Following rules (in itself) doesn't protect you or give you great outcomes," she said.
She became, in her own words, "the worst kid I could be without getting into proper jail". She started modifying her own uniforms against school regulations. She skipped school and picked verbal fights with classmates, until they eventually decided she was more trouble than she was worth.
She had finally won some peace and respect, but it resulted in her losing the title of prefect.
She didn't mind too much, though: "To me, a path of rebellion reaped more rewards (at the time)."
Studying was never her strong suit, but Ms Tan made every effort to ensure her grades were good enough to go to university, eventually enrolling in the National University of Singapore's undergraduate psychology course.
In her second year of university, she stumbled across the campus entrepreneurship society.
It was by accident, but it turned out to be exactly what she had been looking for – an outlet for what she would later recognise as a deep resistance to being told what to do by people around her. For the first time, she saw a way to put all her rebellious energy to "productive use".
Unlike so much of her life up until that point, entrepreneurship wasn't a set of rules to follow or a formula to perfect. "You have an idea, you chart your own path."
She dedicated herself to actively participating in the society and, by her third year, became the club's vice-president of global projects, overseeing exchange trips to Beijing, Taiwan and the United States. The exposure deepened her interest in startups, which she found more immediate and accessible than traditional brick-and-mortar businesses.
Soon after graduating from university in 2010, she set up Learnemy, a platform to help people monetise their passions and hobbies.
The idea was simple: a virtual marketplace where anyone with a skill could offer their expertise and know-how to others who wanted to engage their services, learning from them.
Fuelled by adrenaline and wide-eyed optimism, Ms Tan started working to get Learnemy off the ground. She got a loan from her mother, enrolled in the accelerator programme in the Singapore branch of Founder Institute – a business incubator and entrepreneur launch programme based in Palo Alto, California – and taught herself to code by hiring a friend as a weekly tutor.
The startup saw some traction with local press coverage and, at its height, served more than 250 instructors and 900 learners.
But the more the business grew, the more Ms Tan realised that the market was too small and unsustainable. Singapore's learning market at the time, she noted, was dominated by tuition and corporate training, both of which were too competitive and relationship-driven for a newcomer to crack.
During this time, Ms Tan was making a few hundred dollars a month. "That's hobby money. Not career money," she said flatly.
With her savings dwindling, Ms Tan was still determined to do whatever she could to save her flailing startup.
She flew to Silicon Valley in California, US, and spent three months in a hacker house, crashing Y Combinator startup courses at Stanford University and cold-emailing tech and business founders for fifteen-minute calls, looking for anyone who could tell her what to do next.
Instead of healing or revitalising her, the time spent in Silicon Valley turned out to be a school of hard knocks.
Eventually, Ms Tan gave in and shut Learnemy down in 2015.
"I had made my startup so intertwined with my identity," Ms Tan recalled, leading her to internalise its failure as an indictment of herself.
"I didn't have the wisdom to separate my work from my self-worth."
PICKING HERSELF UP... AND FAILING AGAIN
At 26, Ms Tan found herself starting again with nothing while most of her peers had just gotten over the growing pains of establishing their teething careers.
Her old schoolmates were moving on to promotions and pay raises, but she was back on the job hunt. It felt like she'd been forced two steps back.
Ms Tan started going out of her way to avoid gatherings and catch-ups with university friends, including declining dinner invitations to restaurants that were beyond what her shoestring budget could handle.
"When they wanted to go eat a nice steak, I'd just make an excuse," she said, recalling that this led to more than a few awkward social interactions.
"It's okay. Now I make more money than all of them," she added, with an impish laugh.
Eventually, she secured a job at a media company covering tech startups, organising events and coaching people to develop and improve their sales and investment pitches.
It was her first real attempt at a full-time job – then she lost it after just six months.
With about S$6,000 left in her bank account and no clear path forward, Ms Tan felt she had no other choice but to keep moving.
Soon after, at the end of 2015, Ms Tan landed a contract marketing role at Meta, the multinational heavyweight behind global social media platforms such as Facebook, Instagram and WhatsApp.
A few months into her role at Meta in 2016, she started a new venture: TechLadies, a 16-week coding bootcamp for women modelled on how she had taught herself to code, with participants building web applications for non-profits.
Her work on TechLadies led to Meta offering her a contract role developing community programmes where she helped launch the Developer Circles programme across Asia Pacific.
Eventually, her contract position became a full-time one – but, having been burnt one too many times, she spent the next five years largely keeping her head down and focusing on "work, work, work".
In March 2020, Meta upped her Asia Pacific-focused role to a global one, an opportunity that included an invitation to be based in San Francisco, where the company's headquarters are.
Thanks to COVID-19, she spent a year or so doing the job remotely from Singapore instead before finally making her big move to California in 2021.
'I MADE FAILURE FUNNY'
The seeds of Ms Tan's comedy career were planted long before she ever set foot on a San Francisco stage.
Back in 2015, during her short-lived stint at the media company, Ms Tan came across something she had never before seen the likes of: F***up Nights (FUN), an international movement with chapters in 260 cities across 65 countries in which professionals gather to share, publicly and without apology, the stories of their worst failures.
On a whim, Ms Tan attended a FUN event in Singapore and took to the stage to share about her failed startup and Silicon Valley misadventures. Nobody had told her to do so, but she found herself weaving jokes into her tales of woe.
She hadn't expected the room to respond with belly laughs and guffaws, but the reactions instantly made her feel less alone.
"When I was failing or just failed, it was a very lonely process. Nobody talks or wants to talk about their failure," she said.
It was the first time she realised that her relationship with failure didn't have to hinge on shame or self-denigration – it could instead be about acceptance and connection.
"People were laughing, and we really bonded over my trauma," she said, disbelief echoing clear in her voice even years after the memory.
"I made failure funny."
Upon losing her job at that company, she went back to another FUN event and talked about it. The laughs she got at this second outing made her realise there was something significant about being able to turn her pains and hurts into stories that could make people laugh.
"I just didn't know (what) I was doing was called stand-up comedy," said Ms Tan.
However, it was just a taster. Her formal introduction to comedy as an art form came much later, when she was living in San Francisco in 2021.
Deep in the throes of the slow collapse of a three-year long-distance relationship – her ex-partner was based over 1,000 km away in Portland, Oregon – she saw a poster for a four-week stand-up course, culminating in a live performance in front of a real audience for the fifth and last week. She signed up without a second thought.
Right away, she learnt that there's much more to being funny than just clowning around and "doing whatever".
"There's a lot more structure to creating a joke than I thought ... a lot more thought and craftsmanship."
She completed the course and decided to keep going with stand-up comedy. However, progress was slow and tedious: one show every two months, played to 10 or so people at a small bar.
In 2023, a booker for Cobb's Comedy Club – widely recognised as one of the city's most iconic comedy clubs – found her via social media and offered her a slot.
It was by far her biggest comedy opportunity yet, and only her 18th time performing on stage. She recalled being so wracked with nerves that she took half a day off work to rehearse.
That night, the memory of laughter echoing off the high ceilings remains fresh and vivid in her mind.
"The first time I heard two hundred people laugh at my joke ... it was really electrifying," she said.
That experience lit a fire under Ms Tan, and she got serious about honing her craft. She began approaching joke-writing the way she once approached building a startup – methodically, iteratively, with a low tolerance for wasted effort.
She began poring over stand-up specials by other comedians. She studied comics like Michelle Wolf and Ali Wong for their razor-sharp observational skills, as well as Mike Birbiglia, Jeff Arcuri and Atsuko Okatsuka closely for their personable style – "hearing them is like hearing a friend talking to you over brunch".
Over time, developing her comedy skills has also helped her reshape and redefine her relationship with failure.
For any comedian, bombing is not a matter of if but when – a fact Ms Tan has learnt to make peace with by now.
"When a joke bombs, it is a 'micro failure'. That didn't work out, but I'm still on stage, so I still have to power through.
"It (still) feels bad! But I can just say, 'Ah, that's a new joke, we'll scratch that.' I can acknowledge it, make fun of myself and move on."
The way Ms Tan sees it, learning to embrace failure hasn't just made her a better comic. It's made her a more resilient person.
When a joke bombs ... I can acknowledge it, make fun of myself and move on.
It's a mindset that has proven helpful for her even when she's not delivering punchlines on a stage or a microphone, she added, pointing to moments at work when her ideas and proposals don't make their intended impact or when projects she's spearheading end up stalled.
"I don't dwell on things as much (anymore)," she said.
NOT JUST FUNNY BUSINESS
While performing a set in 2024, Ms Tan made a quip about Singaporean grandmothers urging children to finish their food lest they offend or insult starving children in Africa.
What she thought was a distinctly Singaporean tic struck a chord far beyond home, prompting strangers from Italy, the Middle East and Latin America to approach her with excitement and amusement, saying "That's my grandmother, too."
In this moment, Ms Tan began to understand what comedy could do: Help people fixate a little less on what makes us different and focus instead on celebrating the ways we're similar.
As she pounds the pavement hitting up comedy bars and clubs, she has also been quietly building towards something more ambitious: a hundred-million-dollar social impact fund.
She has a 10-year plan to grow and use this fund for a variety of causes across the globe, from improving underprivileged people's access to basic needs such as food, water, healthcare and education to galvanising individuals to grow their careers, pursue creative ambitions or monetise their passions.
The idea builds on the social impact work she has already been involved in over the years. Chief among these is the inception of Average Foundation in 2021, which funds small, one-off community projects in Singapore and San Francisco through direct giving.
More recently, she co-founded Solve for Change, a micro-grant programme that awards up to S$600 to community-led initiatives focused on digital learning, community empowerment and youth leadership.
For now, she is currently funding it out of her own salary alongside a group of like-minded individuals, project by project, while the larger structure takes shape. Eventually, she hopes to obtain larger-scale funding from institutions such as foundations, family offices and philanthropic funds.
She's fully aware it may sound absurd to some – after all, a hundred million dollars is far from small change.
But "dreaming is free", she said with a shrug. "My ultimate purpose in life is the social impact stuff, and I think comedy is a voice (that) can help build that."
She now has her sights set on moving to New York to sharpen her comedy skills, where she will be essentially starting over from scratch and competing with the best from all over the United States. She's under no illusions about how hard it will be – but the way she sees it, why wait?
"Do something before you feel ready, because you never feel ready. You just (have to) trust that you can catch yourself afterwards."
Spoken by anyone else, the words may sound flippant. But when Ms Tan asks, "What's the worst that can happen?", it's anchored with the kind of calmness and certainty that can only come with having grappled with one's most glaring mistakes and shortcomings, and reached a place of genuine self-acceptance.
For now, Ms Tan no longer feels burdened by the laundry list of failures under her belt. Instead, she seems almost bolstered by them, like they're endowing her with the confidence to roll with whatever punches may come her way next.
"I care about telling people about my failures because I'm living proof that I can come out of it – and now with an interesting story to tell."
