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How a Billion-Dollar Company is Now Becoming Obsolete

Gupshup – A Tale of Messaging, Mistakes, and Mastery

“Why does my phone only send texts in chunks?” It’s 2003, and Beerud Sheth is having yet another frustrating conversation about SMS limits with his friends. Back then, texting was a mess – fragmented, expensive, and just plain inconvenient. Businesses couldn’t use it effectively, and developers? They didn’t even know where to begin. Little did Beerud know, this small gripe would eventually lead to the birth of a platform that would redefine messaging: Gupshup.



But let’s rewind a little.

The Beginning


Beerud Meets the Problem Beerud wasn’t your average tech enthusiast. He’d already co-founded Elance (the precursor to Upwork), a platform that revolutionized freelancing. But in 2004, he noticed something: communication, particularly on mobile devices, was broken.



Enter Rakesh Mathur, a serial entrepreneur who had sold his startup Junglee to Amazon. Rakesh, with his knack for spotting market gaps, joined forces with Beerud, and the two began tinkering. They realized that while businesses wanted to reach customers through SMS, they had no easy, scalable way to do it.


“What if we built something that made messaging as simple as an API?” Beerud asked one evening. And with that, Gupshup was born.



 

The Vision


A Messaging Revolution Initially, Gupshup started as a group messaging platform. Think of it like a blend between WhatsApp groups and Twitter feeds. People could join, chat, and connect. It was fun, but there was something missing.


“It’s cool, but how do we make money?” Rakesh questioned. That’s when the duo had their eureka moment: the real gold lay in providing messaging tools for businesses.


Developers didn’t need another chat app. What they needed was a platform – one that simplified sending bulk texts, integrating chatbots, and connecting businesses with their customers.


Gupshup quickly pivoted, offering a freemium model that let businesses try messaging services for free, with paid options for advanced features. It was an instant hit.




Breaking Into the Market: “Hello, India!” By 2008, Gupshup was buzzing. Businesses in India, where SMS was the king of communication, jumped on board. Startups used it to send transactional messages. E-commerce companies relied on it for delivery notifications. Even political parties used it to connect with voters.


“Why India?” an investor once asked Beerud.“Simple,” he replied. “Mobile phones are everywhere, and SMS is universal.”


Gupshup also got a head start by partnering with telecom operators. By solving their scalability issues, the company became the go-to choice for businesses that wanted reliable messaging solutions.


The Funding Rollercoaster With growth came attention.

  • In 2006, Gupshup raised $10 million in Series A funding.

  • By 2008, Series B brought in another $12 million.


Investors were sold on the simplicity of their platform and their impressive growth in India and emerging markets. Gupshup became a household name in tech circles, often referred to as the “messaging backbone for businesses.”


The Problem with Success But then came the cracks.


By 2012, the world of communication was shifting rapidly. Apps like WhatsApp and Facebook Messenger entered the scene, and SMS suddenly looked outdated.

“We’re fine. SMS is still huge,” Gupshup’s team believed. But they underestimated how quickly the market was changing.


 

The Mistakes


  1. Over-Reliance on SMS: While the world moved to instant messaging apps, Gupshup doubled down on SMS instead of diversifying.

  2. Intense Competition: Players like Twilio emerged, offering better tools and aggressive pricing in the API space.

  3. Slow Adaptation: Gupshup was late to embrace the chatbot and conversational AI wave.


Revenue slowed. Competitors overtook them. And the once-dominant player began to fade into the background.


 

The Resurgence

Gupshup 2.0 But here’s where the story takes a turn.


In 2021, Gupshup shocked the industry by raising $240 million, earning it unicorn status with a valuation of $1.4 billion.



“What changed?” you might ask.


Beerud and his team had spent years quietly rebuilding. They didn’t just fix their mistakes – they reimagined their future:


  • Pivot to Chatbots: Gupshup became a leader in conversational AI, helping businesses build chatbots for WhatsApp, Facebook Messenger, and beyond.

  • Omni-Channel Communication: They expanded to include voice, video, and instant messaging, not just SMS.

  • Focus on Developers: By making their APIs even more developer-friendly, they attracted startups, enterprises, and even global giants.


“We never lost our customers. We just had to figure out how to help them better,” Beerud explained.

 

After Gupshup refocused on chatbots, AI-driven messaging, and omni-channel communication, it did manage to recover some of its lost value, earning back the unicorn status (valued at $1.4 billion again) by raising $240 million in 2021.


However, the phrase "the market was no longer as forgiving as it once was" reflects the fact that Gupshup's comeback wasn’t as smooth or impactful as its previous rise. Here's why:


 

1. Market Maturity & Increased Competition:


By the time Gupshup shifted its strategy to include AI, chatbots, and omnichannel communication, competitors like Twilio, WhatsApp, and other messaging platforms had already established strong footholds in the market.


  • Twilio, for example, had already built its own reputation in the API messaging space, offering competitive pricing and more robust features.

  • WhatsApp, Facebook Messenger, and others had already attracted significant adoption among both consumers and businesses, leaving Gupshup playing catch-up.



2. Customer Retention but Diminished Growth:


While Beerud mentions that “we never lost our customers”, Gupshup didn’t fully capture new customers at the same pace as before. They were able to maintain their existing client base (thanks to their history and established network), but attracting new customers became increasingly difficult because the market had already been saturated by more agile, innovative competitors.


Their focus on rebuilding didn’t allow them to tap into new, emerging markets or exploit disruptive technologies quickly enough to reignite their previous growth trajectory.



3. Slower Growth & Less Explosive Valuation Increase:

Even though they regained unicorn status by raising funding, the market conditions had changed drastically. Gupshup’s valuation, while impressive, didn’t explode as rapidly as it did in its early years because:


  • The industry had matured, and Gupshup wasn’t the only player offering business messaging solutions anymore.

  • Competitors had already solidified their market positions and built extensive customer bases.

  • Startups and investors had shifted their focus to new trends, such as cloud-native platforms and integrated customer support solutions.


Gupshup did get some of its earlier valuation back, but the explosive growth potential wasn’t as strong as it had been in the early days of SMS dominance, when they had little competition.


 

 

Lessons for Startups

Gupshup’s journey – from meteoric rise to near obscurity, and then to resurgence – is a masterclass in entrepreneurship. Here’s what today’s founders can learn:


  1. Adapt to Market Shifts Quickly: The lesson here is clear: startups need to adapt fast. Gupshup failed to see the SMS decline and the rise of messaging apps. By the time they pivoted, they were no longer the first choice for businesses looking for modern communication solutions.

  2. Diversify and Innovate: Gupshup’s one-dimensional reliance on SMS created a vulnerability. New businesses should always be open to diversifying revenue streams and expanding product offerings. Innovation shouldn’t just happen when things are already in decline; it should be a constant effort.

  3. Invest in Customer-Centric Solutions: Gupshup eventually came around to building chatbots and AI-driven solutions, but they should have started this shift earlier. Startups need to understand customer needs and develop solutions before the market moves in that direction.

 

Klubzero POV


Gupshup’s story isn’t just about messaging. It’s about grit, adaptability, and the courage to try again. Whether you’re a budding startup founder or a seasoned entrepreneur, remember this: success is never final, and failure is never fatal.


Gupshup’s story is a tale of success, missed opportunities, and the dangers of complacency. While the company is still operating, the valuation decline and shift in market dynamics are a clear reminder to entrepreneurs: timing and adaptability are everything. The tech world moves fast, and staying ahead requires constant innovation, a proactive mindset, and the ability to pivot when necessary.


So, the next time you receive an OTP or a delivery notification, pause for a moment. Chances are, Gupshup is working behind the scenes, quietly powering the conversations that make our world go round.


At KlubZero, we believe that businesses can learn from Gupshup's mistakes and apply these lessons to avoid similar pitfalls. Success is never guaranteed, and the journey from billion-dollar heights to obsolescence can happen quicker than we think.


 

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