#UNTOLD | Fire, Fear & Failure: How Krish Ramineni Chased his Fireflies

“What is your son doing?”

The question was harmless. But by 2018, Krish Ramineni had begun hearing it as an insult.

He was back in India, at one of those sprawling family gatherings where conversation travels faster than people do.

The room hummed. Laughter burst from one corner and travelled across another. Relatives called out to relatives. Cousins who hadn't met in months found each other. Parents beamed as introductions were made. Someone had become a doctor. Someone was doing well at work. Someone had a startup that seemed to be going places. Faces lit up. Voices rose. There was much to celebrate.

He scanned the room, dodged a glance, changed direction. Ramineni wanted to disappear.

His eyes darted from face to face, searching for conversations he could avoid. A familiar relative caught his eye from across the room. Ramineni looked away. An older relative turned towards him. He shifted his gaze, edged towards another group, kept moving.

Every smile threatened an introduction. Every introduction risked a conversation. And every conversation could eventually corner him with the question he had spent the evening trying to escape: So, Krish, what are you doing these days?

It shouldn't have been difficult. Once, answering it had required almost no effort. Penn. Microsoft. A promotion within eight months. Cambridge next. Ramineni calls himself the “model poster child” his Indian parents wanted him to be. Back then, his introduction practically wrote itself.

Now the room sounded different.

Another peal of laughter. Another glowing introduction. Another parent with something good to report. And somewhere in all that cheerful family noise stood the former Microsoft employee who was living with his parents and earning no salary.

He was building a startup. He knew that. His parents knew that. Yet inside his head, the words had acquired an uglier translation.

“That's an excuse for saying he's unemployed.”

Nobody had called him unemployed.

“No one's mean to your face,” Ramineni recounts.

That was almost the problem. There was nothing to fight. Only smiles. Questions. Pauses. Introductions. And whatever his mind chose to put inside them.

“I could almost feel like there's some judgment.”

Ramineni couldn't stop comparing. Around him, cousins his age seemed to be moving forward. His life felt stuck.

Two years earlier, he had walked away from Microsoft. He had stopped going out. Stopped attending parties and birthdays. He worked every day.

The products still failed.

Across the room, his parents were talking to relatives. Ramineni watched. He knew the question sometimes came when he wasn't even there. Relatives would call his parents and ask: What is your son doing?

The boy who had once made those conversations easy now imagined the pause that followed the answer. Maybe none of it happened.

It happened to Ramineni anyway. “I felt like my parents were getting embarrassed telling them he's doing some startup,” he reckons. Once, he had been the easy son to explain. Now Ramineni feared he had become the answer they dreaded giving.

The embarrassment followed him back to America. So did a question: What was he doing wrong?

Ramineni worked every day. The results refused to come. “It just was not clicking for me,” he says.

That baffled him. Until then, effort had behaved predictably. Work hard, get the grade. Work hard, get into university. Work hard, get promoted.

But the startup world broke the equation. “In college when I work hard, the results came,” he says. “But in entrepreneurship, hard work doesn't guarantee any success.”

WHEN HARD WORK STOPPED WORKING

By 2018, two years into his startup journey, Ramineni had a word for what life had become: “hellish”.

By then, he and co-founder Sam Udotong had developed a ritual neither wanted. Build, launch and wait. Months could disappear into a product. Then launch day arrived. Silence. The world barely looked up. They started again. Four products. Five. Six.

To Ramineni, every launch had begun to resemble a Friday at the box office. His father's side of the family had worked in the Indian film industry. He knew what happened when months of work, money and hope were handed over to an audience.

“Imagine you're like a movie actor and your debut movie is a failure,” he says. Then the flops keep coming. “And this is your last shot or no one's gonna produce anything with you.”

Except Ramineni had no producer to fire him. He could keep producing his own flops. By the fifth or sixth launch, even failure had become familiar. “Yeah, the launch is not going to mean anything,” he remembers thinking.

Then came the reflex. What's next? Another idea. Another product.

Ramineni admits now that it was the wrong instinct. Some of those six products, he believes, might have become businesses had they stayed with them.

But failure had taught him to expect another failure. Quitting was different. Microsoft was on the résumé. A well-paid job was hardly fantasy. There were mornings when he woke up asking: “Is this worth it?” “What am I doing?”

Udotong had an exit of his own: Harvard Business School.

Two years had passed. Things weren't working. Ramineni told his co-founder he would understand if he left. Harvard was Harvard. Udotong's answer came back: “What are you talking about?”

They had made a deal. Even if they didn't make much money, they would make enough to feed themselves, pay rent, keep the servers running. Above all, they would build something of their own.

“What did we agree on day one?” Udotong reminded him. “We want to do this on our own.”

Udotong stayed.

The arithmetic, however, remained brutal. Ramineni had walked away from Microsoft after roughly a year, leaving behind salary and stock that he now estimates would eventually have been worth around ₹10 crore.

“It was foolish then,” he says. Two years later, it looked even more foolish. But Udotong wasn't leaving. Neither was Ramineni. “I have to prove that I can do this on my own.”

Then came India. The relatives. The question. The embarrassment.

By January 2019, something snapped into place.

“I have to turn things around,” Ramineni remembers telling himself. “Do or die. This is the only way.” No backup. “This is a single shot,” he says. “Last shot.”

Two months later, Ramineni was back in India for a cousin's wedding. Still, in his words, “nothing, no proof to show”. But something had changed. People could see him working. Meetings kept coming. Ramineni was constantly busy. His head remained merciless. Why does this guy act so busy? Has nothing to show for it.

Then comes the qualification that says as much about Ramineni as the thought itself: “Maybe they didn't think this.”

He did. By then, escaping the question was no longer enough. He needed an answer. And after six failed products, Ramineni and Udotong finally questioned the one thing two engineers had always trusted first: engineering.

Six times, they had thought of an idea, built it, launched it and then discovered whether anybody cared.

Now they reversed it. “Before we write a line of code,” Ramineni recalls, “let's go validate the problem.” Find the need first. Build later.

There was one problem with selling an AI assistant before building the AI assistant. Someone still had to do the work. The company was called Fireflies. The assistant was called Fred.

Except Fred wasn't quite AI yet. Fred sounded like software. Fred behaved like an assistant. Fred cost roughly $100 a month. Behind the screen were humans. Customers were told they were buying a “human-enabled business with AI on top”. Ramineni and Udotong tested it with roughly 10 people, many of them close friends.

For once, the engineers weren't asking: Can we build it? They were asking: Will anybody pay for it? The answer came back. Yes.

Ten people were hardly a market. But they were proof. Someone had a problem. Someone would pay to make it disappear. Investors suggested they could keep going that way: retain the humans, wrap technology around them and build a business.

Ramineni and Udotong refused. They were engineers. “We could have built that business,” Ramineni says. They wanted the machine to do the work. So, they pulled the humans out. And the traction vanished with them.

Back to zero. Six failures behind them. One last shot in front. And Fireflies had gone flat.

FINALLY, THE SEVENTH FIREFLY

This time, they didn't run.

They iterated. Improved the product. Worked through the engineering. For months, little happened.

Then the graph moved. People started using Fireflies. Then telling other people. One user brought another. Another brought another. Ramineni had seen enough flat launches to recognise what was happening. This one was beginning to travel.

Again, he reaches for cinema. A movie without star power opens flat. Then somebody watches it and tells a friend: It's not bad. You should see it. Day two gets better. Then day three. “That literally happened with our product,” Ramineni says.

He can trace the millions who would eventually use Fireflies back to its first 100 users. Perhaps 50, he estimates, were friends. They told others. Those people told others. “The Fireflies started to just spread like that.”

After years of watching products die at launch, Ramineni finally woke up to one that was moving. His first thought wasn't celebration. It was the bank account. “At the rate we're going, our bank balance is going to be zero.”

Fireflies was taking off. But that was precisely the problem. Why? Because they could run out of money.

Now the founders split the battlefield. Ramineni talked to investors. Udotong kept the system running. The investors wanted to try Fireflies. The users wanted Fireflies to work. And the two-man team had to satisfy both.

Then came the tickets. Why is the product down? Twenty minutes. Thirty. Another bug. For almost four years, Ramineni had wanted people to care. Now they cared enough to complain. “For almost four years, we were begging people to use the product,” he says. And now all of a sudden people wanted to use it. Product-market fit had finally arrived. Ramineni laughs at the idea that this made life easier. “No, it's just as hard.”

The fear had simply changed shape. Before, nobody wanted what they built. Now people wanted it, and Ramineni wasn't sure they could afford to keep giving it to them.

And there was only one way out: Raise money. Investors liked the story Ramineni could finally put on a screen. Fireflies was growing. Usage was climbing. The dashboard moved. What he couldn't put on the screen was the panic underneath it. “You can't tell them, ‘Hey, you need to fund us now or we're going to run out of money,’” he says.

So, Ramineni pitched.

By the summer of 2019, Fireflies had a working product and investor meetings became nonstop. Then came a term sheet. Someone was finally willing to bet on them. Yet credibility remained a problem. “So many people at the time would get funding,” Ramineni recalls, “but we weren't able to get funding because we didn't have that credibility.”

Fireflies had users. Growth. Customers complaining when it went down. Ramineni finally had something to show. And he was still walking into rooms asking people to believe him. Only the rooms had changed. The relatives were gone.

Now the judgment sat across the table with a chequebook.

And for a moment, it looked as if Ramineni had passed the test. At a conference in Boston, he met investors who liked Fireflies and said they would invest.

Ramineni flew back to San Francisco carrying their word with him. Then the emails started landing. “Sorry.” “We're hesitant.” “I know I said yes, but I don't want to invest.”

The money disappeared before it arrived. Ramineni took it personally. Not merely because Fireflies needed the cash. Because they had said yes. “You gave me your word,” he says. “Your word means everything to me.” He didn't call demanding explanations.

But the rejection found an older bruise: India. The relatives. The question. The man who had once struggled to show his face at family gatherings was being told, once again, that what he had built wasn't enough.

This time, the humiliation made him angry. “If there's one motivator that's always driven me, is when someone says, you can't do this,” he underlines.

So, he kept pitching.

By August 2019, Fireflies had its seed round.

Ramineni could finally take a vacation. Almost. His younger brother had graduated from high school and wanted to take a trip. Ramineni went with him. Then his phone started demanding attention. The funding wire hadn't arrived. Even on vacation, Ramineni was back on calls, chasing the money that was supposed to have bought him the right to switch off. It would be his last vacation for years. But the cheque changed something. The fire had started.

Then the world shut down.

Covid emptied offices and pushed meetings onto screens. For a company built around meetings, the timing was explosive. Ramineni doesn't pretend otherwise. “The pandemic was like the fuel on top of that little ember,” he confesses.

The ember exploded. The company that had once begged people to use its product suddenly had a very different problem. People knew Fireflies. People used Fireflies. Investors wanted Fireflies.

For years, Ramineni had dreaded the answer to a simple question: What does your son do? Soon, strangers would begin supplying it for him. You're the guy behind Fireflies.

THE ‘POSTER CHILD’ WHO BROKE THE SCRIPT

The sentence would have sounded ridiculous to the five-year-old who left India for America with parents who wanted a better education for their son.

Ramineni followed the script almost perfectly. Penn. Microsoft. A promotion within eight months. He was, in his words, the “poster child”. Except something refused to settle. “I was not satisfied with myself,” he says. His mother had apparently seen it coming. “One day he's just going to work for himself,” she would say. “He doesn't listen. He needs to do his own thing.”

Leaving Microsoft was difficult. But explaining why to his parents was worse.

So, Ramineni found himself a respectable escape hatch: Cambridge. He applied. Got in. His parents were delighted. Except Cambridge was about to become another door he refused to walk through.

With a month before the programme began, Ramineni went to Boston. He and Udotong had been building things together remotely for years, often without even switching their cameras on. The two men who would eventually build a company around meetings had learnt to trust each other without sharing a room.

Now Udotong pushed. Why wait until after Cambridge? Why not now?

Ramineni committed. Then, while packing for the life he was supposed to enter, the certainty cracked. Am I really doing this?

“This is crazy,” he remembers thinking. “I felt like that kid that sneaks out at night past curfew without telling their parents.”

His parents thought Cambridge waited at the other end of Boston. Then came the call. He wasn't going. “What do you mean you're not going to Cambridge?”

Ramineni had little to offer his father except instinct. Cambridge would still be there. This opportunity might not. “I hope you know what you're doing,” his parents told him.

Then came the second bomb. He was moving back home. His mother found one consolation. She could make sure he ate.

The gamble was bigger than walking away from Microsoft or Cambridge. Ramineni was betting on a co-founder he had barely spent time with in person.

When they eventually began working together every day in Boston, something clicked before any product did.

“This is so fun,” Ramineni remembers. Udotong went further: “Wouldn't it be fun if we could just do this every day?” And then came the line that perhaps explains why Harvard couldn't prise him away later: “Who cares what we build?”

The product, it seemed, was almost incidental. They had already chosen each other. They didn't know what they would build. Curiously, they already had the name.

BEFORE THE PRODUCT, THERE WERE FIREFLIES

The name went back to college, when Ramineni and Udotong worked on drones that blinked against the night sky like fireflies.

It stuck through project after project, partly because it was vague enough to survive their pivots and partly, Ramineni laughs, because they were too lazy to keep changing it.

Only later did a customer spot a meaning the founders had missed: Fireflies was a fly on the wall, sitting quietly inside a meeting, listening and taking notes.

They ran with it. The name had survived six failed products. Now the company finally had too. And the poster child who once worried about how his parents explained him had arrived at a strange inversion. People no longer asked what he did. They told him “you're the guy behind Fireflies.”

For Ramineni, however, an even bigger compliment is simpler: I use Fireflies every day. “That's the biggest compliment anyone can give me,” he says. Perhaps because he remembers exactly how long nobody used it.

Success also changed his relationship with money. Fireflies would later raise $14 million when, Ramineni says, it didn't actually need the capital. Today, when investors push bigger rounds and bigger valuations, his question is simple: What would he do with the money? “If it's just fundraising for the sake of fundraising for an ego boost, I don't want to do it.”

After years of struggling to raise money, Ramineni had learnt its limits. Capital could help Fireflies grow. It couldn't give the company the one thing that mattered first: customers.

His arithmetic is simple. “You just need to focus on your first 10,” he says. Ten became 100. A hundred became 1,000. And six failed products had taught him why that sequence mattered. “No amount of fundraising, no amount of capital can create demand.”

Money wasn't the only thing Ramineni had learnt to question. Advice was another. “The mistake is listening to people who haven't gone through the journey you want to go through,” he says.

Another lesson goes further back. As a boy, Ramineni could study for 10 minutes and ace an exam. For a while, that was the flex: getting the grade without working particularly hard.

Then, around the age of 15, he noticed something unsettling: people he thought he was smarter than were overtaking him. They worked harder. Talent had given him a head start. It couldn't keep running for him.

Years later, ask Ramineni to choose between talent and fire in the belly and there isn't much of a contest. “Work ethic is far more important.” And then: “Talent is nothing without discipline.”

Six failed products had taught him that. They had also taught him something about the paths people are encouraged to take in the first place.

WHAT IS YOUR SON DOING?

For Ramineni, that conversation inevitably leads back to India, to parents and to the careers generations have grown up recognising as safe: doctor, engineer, lawyer. “There is no tried and proven path,” he says.

Yet step off the familiar one and failure can suddenly look more frightening. A startup that goes nowhere. An acting career that doesn't take off. A child choosing cricket over engineering. The further the choice sits from the conventional path, the harder it can become for families to trust where it might lead.

Ramineni wants parents to give that uncertainty a chance. “If they're passionate, let them pursue that passion,” he says. “See how far it gets them.” A child, he argues, doesn't have to be exceptional at 20 things. Sometimes the thing a child is exceptional at simply isn't the thing everyone is looking for.

Ramineni would know. Because in 2018, he stood inside that family gathering listening to the laughter and glowing introductions, scanning faces, dodging conversations, terrified that somebody would ask: What is your son doing?

He had an answer then. He's doing some startup. It was Ramineni who didn't believe it sounded good enough. Years later, strangers began giving him another answer: You're the guy behind Fireflies.

Funny what success can do to an introduction. But six failures had already done something more important to Ramineni. They had cured him of needing the answer to sound impressive. The boy who had spent an evening dodging eyes had spent years chasing something nobody else could see.

Six times, the light disappeared. The seventh time, Ramineni reached out. His Fireflies stayed.