Bihar man visited 100+ countries & took 700+ flights to “research travel” – now runs an AI-powered online travel agency with 22M+ properties

They say travel changes you in ways you can’t even imagine.

It opens up your horizons, makes you discover yourself over and over again, and most of all…it makes you realize that you are bigger than the life you were living. 

For Ritesh Raj, co-founder and CEO of CuddlyNest, travel became a defining chapter in his life. 

“The thing about travelling is that you never know what seeds are being planted and why. During my research break, where I visited more than 100 countries, a version of me was unknowingly being prepared for CuddlyNest. As I repeatedly faced everyday traveller pain points, I became driven to change the way people interact with online booking platforms. Almost five years later, my team and I have achieved this,”Ritesh Raj tells Startup Pedia in an exclusive interview.

THE BACKGROUND 

Hailing from a small village in Bihar, India, Ritesh grew up thinking different from his surroundings.

At the time, global entrepreneurship wasn't exactly trending. People didn't leave their towns to “create” something new elsewhere. Everything was tightly-knit, offering little room for deviation. 

He began his career at Wipro in 2007 and later went on to work across multiple companies and roles spanning marketing, customer support, and the travel industry. 

But…how did the love for travel emerge? How did it become an early seed in his life?

When Ritesh was working in New Delhi, he was learning in parallel the world's tongue. He wanted to absorb as much variety as he could. 

So he did something unconventional: he opened his home to travellers from every corner of the world, unintentionally creating one of India’s first true co-living spaces.

Over the years, seventy people lived in Ritesh’s house, each with stories, accents, and worlds that expanded his own. 

By 2013, simply speaking to people from different parts of the world wasn't enough. Ritesh wanted to experience the variety in culture, thought, and everyday life in its raw, lived form. 

So he set aside his well-paying job and did something most would call “reckless.” He packed his bags and decided to visit every country in the world. 

“For me, it was genuinely just essential research, and an excuse to reconnect with all the friends I had made during my co-living experiment,” Ritesh laughs. 

From November 2013 to September 2019, he took 700+ flights, visited 100+ countries, and stayed in 400+ global cities. This included almost every city in India too. 

This wasn't a hurried trip. At every destination, he stayed for at least a week, taking time to truly absorb the place. 

“I would meet former flatmates, consult on projects in my field, and above all, immerse myself in the travel experience. Over these years, I've stayed everywhere: budget hotels, hostels, homestays, five-star hotels, seven-star hotels, BNBs, cottages, you name it,”Ritesh Raj tells Startup Pedia. 

While making use of every available platform to book his stays, Ritesh experienced firsthand the problems plaguing the travel tech sector and, in turn, the traveller.

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THE CUDDLYNEST SEED

In December 2019, Ritesh found himself in San Francisco. He was sipping hot coffee in a cafe called Sightglass Coffee. 

He struck up a conversation with Haitham Saead (then a complete stranger), who has decades of experience in information technology, finance, and consulting. 

The duo discovered their shared obsession with the finest coffee and frustrations toward conventional travel booking platforms.

“Haitham was expressing his own experiences of travel platforms being clunky and impersonal. He disliked that the user interfaces were never smooth and seamless, the way it should be. I was listening to him thinking – if the two of us share these sentiments, then all travelers must,”Ritesh smiles. 

Ritesh and Haitham decided to do something about it, and by January 2020, CuddlyNest was born.

JOURNEY AND CHALLENGES

When Ritesh and Haitham started CuddlyNest, the mission was simple: to make travel booking butter-smooth for everyone (hosts, suppliers, and travellers). 

But soon after the online booking platform was launched, the COVID-19 pandemic hit the world in March 2020, and a global shutdown followed.

Travel froze. Investors panicked. Teams scattered. 

“Sometime later, one of our key hubs, Ukraine, was disrupted by political chaos. Starting a travel company at that exact moment was, objectively, the worst timing imaginable,” Ritesh Raj tells Startup Pedia.

CuddlyNest’s beginning was rocky, but the founders kept at it. 

“We knew the world would travel again,” Haitham Saead adds. 

For the next two years, CuddlyNest quietly expanded by integrating suppliers to expand inventory, improving systems, and building AI models. Early on, the small and focused team of less than 10 people (including the founders) made the decision to build everything in-house. No outsourcing and no subscription dependencies.

“We were rebuilding travel booking from the ground up using better data, smarter technology, and fairer economics,” entrepreneur Ritesh affirms. 

By 2023, global travel had found its rhythm again. The travel industry boomed, and CuddlyNest was fully prepared to absorb the surging demand. 

Building through uncertainty had made the team more resilient than ever. When artificial intelligence (ChatGPT, Grok, Perplexity) became mainstream, CuddlyNest was already ahead of the curve. 

“We didn't really scramble to adapt to AI. Because since day one, robust artificial intelligence was one of our key tenets,” startup founder Haitham Saead says.

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CUDDLYNEST: TRULY WARM, TRULY FUNCTIONAL 

Today, CuddlyNest takes the AI-driven approach to the OTA (online travel agency) model and offers global accommodation, flight booking, and attraction inventory (to be added soon) into one cohesive engine. 

The OTA platform offers clear, sustainable solutions to some of the most evident problems in online travel:

1. Most platforms charge hosts 12–20% in commissions, which inflates prices for travellers and reduces earnings for property owners.

“CuddlyNest charges just a flat 5% fee, which makes it easier for property owners to sustain their business without putting an additional burden on the end consumer,” startup founder Ritesh Raj explains. 

2. Travellers often spend hours tweaking filters and scrolling through thousands of irrelevant results. This causes filter fatigue and decision paralysis.

To address this, CuddlyNest uses ML-powered smart filtering to instantly surface the most relevant options for individual preferences.

“We also prioritize accuracy and relevance, not paid placement. Other platforms push “sponsored” or “promoted” listings that distort results and waste time,” Haitham Saead shares. 

3. Many booking platforms still restrict travelers to traditional card payments. CuddlyNest offers multiple secure payment options, including major cards and crypto, giving travelers more freedom, global accessibility, and faster, borderless transactions.

Apart from AI-driven personalization that tailors search results to traveller intent, CuddlyNest eliminates the need to juggle between multiple applications and websites.

It offers a unified booking experience where travelers can book stays, flights, and attractions in one place, with transparent pricing and no hidden markups or unpredictable fluctuations.

“Our USP is that we are built around users, not algorithms,”Haitham affirms. 

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GROWTH

Currently, CuddlyNest has a listing inventory of more than 22M+ properties across 32+ categories such as vacation rentals, hotels, hostels, serviced apartments, villas, cabins and more.

Apart from accommodation, the AI-driven OTA offers customers the option to book 600+ airlines that fly through 50,000+ routes to destinations around the globe. 

It has a global reach of 188+ countries and 80,000 cities, with a global travel community active in 100+ countries across North America, Europe, and Asia. 

Since 2023, CuddlyNest has completed USD 27.9 million in gross transaction value and served millions of global customers. 

What started as an OTA with just ten people is now powered by a fully remote team of 50 skilled tech experts, working across Europe, Asia, the United States, and the Middle East. 

As far as funding is concerned, CuddlyNest is backed by a dedicated group of angel investors who believe in the need for a more intelligent and equitable travel platform. 

“We are also on track to complete our first major fundraising round in Q1 2026,” startup founder Haitham Saead says.

“This is still just the beginning. Our mission is to change the face of the global travel booking experience as we know it and position CuddlyNest as a leader. My advice to all entrepreneurs is just take the leap... I know I'm glad I did. Of leaving my hometown, of travelling to 100+ countries, of starting something born out of a coffee shop conversation, and of continuing to stay at it even when everything seemed especially designed against it,”entrepreneur Ritesh Raj signs off. 

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