Startup Stage: StayNow wants to simplify trip planning

StayNow

Powered by artificial intelligence (AI), StayNow is described as a "complete travel ecosystem," helping travelers create itineraries, collaborate with their fellow travelers, find local experiences and more.

StayNow was founded in 2023 and operates as both a travel-planning hub and a booking platform.

What is your 30-second pitch to investors?

StayNow is an AI-powered travel hub designed to take the chaos out of planning trips.

Instead of juggling spreadsheets, group chats and half a dozen apps, travelers get everything in one place. With NowAI—our proprietary travel assistant—travelers receive curated itineraries, group consensus tools and direct access to unique hotels and local businesses.

We’re addressing a $1.2 trillion global hotel market with a differentiated model that blends AI personalization, authentic community reviews and strong hospitality partnerships.

Describe both the business and technology aspects of your startup.

Business: StayNow operates as a booking platform and travel-planning hub, built to connect travelers with boutique hotels, restaurants and authentic local experiences. Our model generates revenue through commissions, with additional opportunities in loyalty, memberships and partnerships as we scale.

Technology: At the heart of the platform is NowAI, a conversational AI assistant integrated directly into StayNow’s ecosystem. It collects traveler preferences (with privacy controls), processes them against live booking APIs and delivers real-time results: tailored itineraries, price-checked bookings and group decision support. Our stack combines:

• AI-driven personalization built on a proprietary knowledge base
• A robust privacy engine for group trip planning
• Direct integrations with major hospitality systems such as Cloudbeds, SiteMinder, Mews, Sabre, Oracle, and WEX

Give us your SWOT analysis.

Strengths

• AI engine purpose-built for travel, not retrofitted from generic tools
• Unique and seamless group travel coordination with built-in budgeting tools
• Early traction in beta with 2k+ hotels integrated and access to 50k properties and 1.7k traveler accounts created
• Founding team with proven expertise in hospitality, AI and go-to-market execution
• Clear brand values: ethical responsibility, joy in the journey, empowerment and financial stewardship

Weaknesses

• Brand awareness is still in early stages compared to entrenched travel players
• Reliance on property integrations for inventory depth
• Limited marketing spend at this stage

Opportunities

• Growing demand for authentic, experience-led travel among millennials and Gen Z
• Increasing consumer comfort with AI-driven personalization
• Untapped segment of independent hotels seeking more autonomy and visibility

Threats

• Competitive pressure from OTAs and Airbnb investing in AI
• Regulatory changes impacting the travel and lodging sector
• Need to continuously maintain trust in reviews and recommendations

What are the travel pain points you are trying to alleviate from both the customer and the industry perspective?

For travelers, planning often feels like work—six apps, endless scrolling and conflicting group texts. Decision fatigue and unverified reviews make it worse. StayNow simplifies this by offering one place to plan, chat, poll, book and even split costs.

For hoteliers and local businesses, the challenge is visibility and control. Most platforms are geared towards paid promotions, giving larger brands overwhelming control of results pages. StayNow wants to shine a light on local businesses that are providing exceptional experiences, helping them reach the right travelers, build lasting relationships and pay lower commissions versus other competing platforms.

So you’ve got the product, now how will you get lots of customers?

We’re entering the market with a phased strategy:

1. Destination pilots in Monterey, Lake Tahoe and Napa to test and refine acquisition tactics
2. App-store promotions, influencer partnerships, and social storytelling to build awareness and credibility
3. Cross-promotion with hotels and local partners that benefit from driving their own guests to StayNow

The approach balances efficiency with scale, building momentum through authentic, community-driven growth.

Tell us what process you’ve gone through to establish a genuine need for your company and the size of the addressable market.

We validated demand through research, testing, and traction:

• Studies show 53% of travelers find planning more stressful than the trip itself.
• UCLA and AMEX reports highlight how too many choices reduce follow-through.
• 83% of millennials/Gen Z find generative AI useful for booking travel and 80% use apps or social media to plan.
• Travelers are willing to pay subscriptions if the tools provided make planning and follow-through easier.
• Beta testing of NowAI and group planning features delivered strong feedback and adoption.
• The global hotel market is valued at $1.2 trillion, with the OTA market in the U.S. alone estimated at $230 billion.

How and when will you make money?

Our core revenue initially comes from booking commissions through direct hotel and property management systems (PMS) integrations. Secondary levers include potential premium memberships and brand partnerships that want to advertise to specific traveler markets (e.g. Patagonia marketing to potential Tahoe travelers).

What are the backgrounds and previous achievements of the founding team?

• Romal ‘RJ’ Jayswal, CEO: Hospitality entrepreneur with deep PMS integration expertise and a track record in hotel operations

• Saawan Patel, CTO: Technologist specializing in AI personalization and scalable cloud solutions

• Sidd Raj, CPO: Hotel technology and partnerships leader with strong industry relationships

• Ami Patel, CMO & executive advisor: Veteran strategist in brand building and growth, with experience leading companies to profitability and successful exits

How have you addressed diversity and inclusion within your business?

StayNow is committed to building a company and community that reflects diverse perspectives. That starts with our team, which is spread across three continents and brings together different cultural and professional backgrounds.

This extends into how we represent travelers in our marketing. We believe travel can be transformational—broadening perspectives, sparking connection and reminding us of our shared humanity. On the product side, we prioritize accessibility and inclusivity—from supporting small and independent businesses to designing features that allow a wide range of travelers to find experiences that feel authentic to them, not the travel industry.

What’s been the most difficult part of founding the business so far?

The hardest part has been honing in on the exact battle we want to fight. We quickly realized that the real friction in travel isn’t just about clicking “book”—it’s about search paralysis. With endless options, travelers struggle to move from inspiration to action.

That challenge is amplified in group travel, where multiple voices and preferences make decision-making even harder. On top of that, the relationship between hotels and guests has become fragmented. One of our biggest goals is to stitch that connection back together—to remind both sides they’re on the same team, and to build tools that reflect that shared interest.

Generally, travel startups face a fairly tough time making an impact—so why are you going to be one of the lucky ones?

Because we’re not trying to outspend incumbents on ads or SEO.

StayNow is carving out a new category: the AI travel companion. By focusing on personalization, authentic connections and traveler trust, we’re tapping into the values that matter most to the next generation of travelers. Our traction with hotels, early adoption from travelers and strong product-market fit point toward long-term staying power.

A year from now, what state do you think your startup will be in?

By mid-2026, StayNow will have:

• 20+ curated destinations live
• 3k direct-connect properties integrated
• 100k+ registered travelers, with meaningful repeat bookings
• A Series A raise completed to expand growth

What is your end-game?

StayNow’s vision is to define and lead the “AI travel companion” category. That could mean scaling toward an IPO or joining forces with another hospitality/travel brand through acquisition. Either path aligns with our goal: to become the go-to hub for authentic, AI-powered travel.