thefoundersstory

Perfect Home Away from Home: estaie's Extended Stay Solutions: Osama Shawky

Today in this interview, we have the pleasure of speaking with Mr. Osama Shawky, the CEO of estaie, a pioneering platform that is transforming the extended stay market. estaie uses advanced AI and innovative technology to deliver personalised, flexible long-term accommodation solutions for travellers. In this conversation, Mr. Shawky shares his journey, the challenges and triumphs of building estaie, and his vision for the future of the hospitality tech industry.

TFS: Welcome to The Founders Story, Mr. Osama Shawky! We are thrilled to have you here today. Your journey as a serial entrepreneur, particularly with your latest venture, estaie, has been nothing short of inspiring. We are eager to know more about your experiences, explore what sets estaie apart in the hospitality tech space, and learn more about the innovative solutions your platform offers for long-term travellers.

Osama Shawky: Thank you for having me on The Founders Story. It is a pleasure to be here and to share the story of estaie with you. The journey of building estaie has been incredibly rewarding, and I am excited to share it with your readers.

TFS: Let us talk about the beginnings. What inspired you to start your own business, and how did the idea for estaie come about?

Osama Shawky: The inspiration to start estaie came from my previous experience as the CEO of Thirty Sleeps, a company that specialises in 30-night stays. Together with my co-founder, Mark Reed, who has over 30 years of experience in travel and hospitality and an extensive network of contacts, we identified a significant gap in the market. Business travellers, digital nomads, newcomers, and city shifters needed more flexibility and automation in their long-term accommodation options. This insight led us to create a platform that could cater to stays ranging from 15 to 365 nights.

Realising the potential to revolutionise this sector, we partnered with our third co-founder, Pavel Kuzmin, who has a background in SEGA, DHL, and Shell and has developed more than 20 complex tech solutions. We dedicated several months to designing the first algorithm specifically for long-term stays. This innovative approach aimed to disrupt the market by offering unmatched flexibility and convenience. Our vision was not just to address a market gap but to establish the first global online travel agency (OTA) dedicated to long-term stays.

Thus, estaie.com was born from our collaborative effort and shared vision. Our objective is to use advanced AI to deliver personalised recommendations, streamline the booking process, and provide a seamless user experience. Today, we continue to push the boundaries, ensuring that every guest finds their ideal home away from home, regardless of the length of their stay.

TFS: What motivated you to establish the first extended stay OTA, and how did your experience in digital innovation and hospitality influence your vision for estaie? 

Osama Shawky: As I mentioned earlier, the idea for estaie was sparked by my experience as the CEO of Thirty Sleeps, where we specialised in 30-night stays. Together with my co-founder, Mark Reed, we identified a significant gap in the market for longer-term stays that required greater flexibility and automation. In collaboration with Pavel Kuzmin, we developed an advanced algorithm specifically designed for long-term stays, with the goal of disrupting the market by offering unmatched convenience and personalisation. My background in digital innovation and hospitality played a pivotal role in shaping estaie’s vision to become the first global OTA dedicated to extended stays.

TFS: How does estaie use blockchain and big data technologies to improve security and transparency for travellers and property managers? 

Osama Shawky: At estaie, we use blockchain to establish a secure and transparent ledger for transactions. This helps us maintain data integrity and reduce the risk of fraud. By applying big data analytics, we gain a deeper understanding of customer preferences and market trends. This combination allows us to provide customised recommendations while ensuring top-notch security and transparency for both travellers and property managers. 

TFS: Could you walk us through how estaie’s platform customises its recommendations and services specifically for long-term travellers? What are the standout features that help create a memorable experience for those on extended stays?

Osama Shawky: Sure. You see, we focus on making the user experience as personalised and straightforward as possible. When users visit our homepage, they are guided by clear, easy-to-use icons that help them select their star rating, location, stay duration, budget, and the number of rooms or bedrooms they need. Whether they are looking for an apartment, hotel, or Airbnb, our technology quickly scans the entire site to present the most relevant options.

Our platform offers several key features to enhance the experience. We use advanced algorithms to analyse user preferences and past behaviours, which allows us to provide accommodation recommendations that are tailored to individual needs. Users can also customise their stay by choosing specific services and amenities to ensure their experience is just right. Moreover, we have streamlined the booking process so that users can complete their reservations in just a few minutes, making it both efficient and user-friendly. 

TFS: That sounds excellent. What emerging trends in the hospitality industry do you find most exciting, and how is estaie preparing to take advantage of these trends? 

Osama Shawky: I find emerging trends such as remote work, digital nomads, the growing need for flexible accommodations, and tech-enhanced guest experiences particularly exciting. estaie is well-positioned to make the most of these trends. This is why we provide flexible long-term stay options and use technology to offer personalised experiences. I believe that it is our focus on innovation that helps us stay ahead of market demands and continually adapt to the changing needs of our customers. 

TFS: You might have faced some significant challenges while developing estaie. Could you share what these challenges were and how you managed to overcome them to establish a leading position in the hospitality tech sector? 

Osama Shawky: Ah, yes, like any other business, we too faced challenges. Developing a scalable technology platform was a major task, and securing adequate funding was another significant one. We also needed to build market trust from scratch. To address these, we brought together a talented team of engineers to create a robust platform and engaged investors who shared our vision. We started to focus on forging strong relationships with property managers and delivering outstanding customer experiences to establish our credibility in the sector. 

TFS: Could you explain how estaie uses advanced analytics and machine learning to adjust pricing strategies and enhance property performance?

Osama Shawky: We use advanced analytics and machine learning to fine-tune our pricing strategies. We look into factors like market demand, booking trends, and seasonal changes, and our system adjusts prices in real-time to make sure we get the most out of each booking. This approach helps us keep prices competitive. It also ensures that properties perform at their best, which is beneficial to both our travellers and property managers. 

TFS: How does estaie ensure top-notch customer support for guests staying long-term, and how do you measure and maintain high levels of satisfaction among your customers? 

Osama Shawky: Exceptional customer support is a priority for estaie. Our team offers 24/7 assistance through AI-driven chatbots for quick queries and has a dedicated support team to handle more complex issues. Satisfaction is tracked through surveys, reviews, and direct feedback from guests. This ongoing process helps pinpoint areas needing improvement and ensures high levels of customer satisfaction, as seen in our strong repeat customer rates. 

TFS: How does estaie include sustainable practices in its operations, and how does innovation help promote eco-friendly solutions within the platform? 

Osama Shawky: Sustainability is a core part of estaie’s operations. We work closely with eco-friendly properties and encourage green practices across our platform. For instance, we focus on energy efficiency in our offices and promote smart home technologies. We also support properties that are committed to reducing waste and provide information on eco-friendly travel options. We also help sustainable hotels by offering lower payment fees and boosting their sales.

TFS: What are your long-term goals for estaie, and how do you see the platform developing over the next five years to adapt to changing market needs? 

Osama Shawky: We want us to establish ourselves as the leading global platform for extended stays. Over the next five years, we plan to broaden our market reach and continually refine the user experience. We aim to enhance our AI capabilities to offer even more personalised recommendations and expand into new markets to connect with a larger audience. We also intend to integrate more services and amenities. This way we can enrich our offerings and take a leading role in promoting eco-friendly travel options and practices. We are also working towards offering B2B solutions and becoming the first global flexible living OTA.

TFS: That is a compelling vision for the future of estaie. How does estaie encourage a culture of innovation and ongoing learning among its team? What steps do you take to support career development and work-life balance for your employees? 

Osama Shawky: We encourage a culture of innovation and continuous learning by fostering creativity and teamwork. We offer various learning and development programs, including workshops and training sessions to help our team members enhance their skills. Our innovation labs provide a space for experimenting with new ideas and technologies, while our mentorship programs support professional growth by connecting employees with experienced mentors. We also promote work-life balance through flexible work policies, allowing for adjustable hours and remote work options. 

TFS: I hope you do not mind me getting into something more personal, but could you describe what a typical day looks like for you as an entrepreneur? 

Osama Shawky: Not at all. A typical working day for me is quite busy and dynamic, reflecting the range of responsibilities I handle at estaie. My mornings begin early with a review of key performance metrics and updates from various teams. This includes checking the progress of our automation initiatives, evaluating marketing campaigns, and analysing SEO performance to ensure our online presence is strong.

Throughout the day, I take part in strategy meetings to discuss ongoing projects, brainstorm new ideas, and address any issues that arise. I spend a lot of time with our sales team, refining our approach to customer acquisition and retention, and working closely with our marketing team to optimise our strategies for the best results.

Fundraising is another important part of my role. I set aside time to connect with potential investors, present our vision, and secure the necessary funds to support our growth. Leadership and mentorship are also priorities for me. I hold regular one-on-one sessions with team members, offering guidance and support to help them achieve their goals. I also mentor our interns, ensuring they gain valuable experience and insights.

I also make it a point to dedicate two hours each week to give back to the community, whether through volunteer work, participating in local initiatives, or offering mentorship to aspiring entrepreneurs.

TFS: How do you stay motivated and driven in your entrepreneurial journey, especially during tough times? 

Osama Shawky: Staying motivated, especially during challenging times, comes from my deep passion for what we are building at estaie. I am driven by the vision of transforming the extended stay experience, which keeps me focused and energised. The dedication of our team and the positive feedback from our customers also provide me with great motivation.

I view obstacles as opportunities for growth and innovation. Maintaining a positive outlook, being adaptable, and learning from each experience are crucial. I am fortunate to have a supportive network of mentors, peers, and my exceptional team, which is vital for staying resilient and motivated.

Taking care of my mental health is a priority. I make sure to balance work with personal well-being by keeping an eye on my schedule and setting aside time for activities like exercise, meditation, and spending quality moments with family and friends. These practices help me stay grounded and refreshed.

I also find motivation in contributing to the startup community. Mentoring young entrepreneurs, especially first-time founders, is incredibly rewarding. Sharing my 23 years of experience across six startups and three successful exits aims to provide them with valuable insights and help them navigate their own journeys. Supporting their growth also reignites my own passion for entrepreneurship.

I set clear, achievable goals and celebrated small successes along the way. By focussing on the broader vision for estaie, I maintain my drive and am able to overcome any challenges. 

TFS: What advice would you give to aspiring entrepreneurs who want to start their own business? 

Osama Shawky: Starting your own business can be an exciting yet demanding journey. First and foremost, look after your health. You need to be in good shape to lead effectively, so make sure to get regular exercise, eat well, and get plenty of rest.

Family support is also crucial. Your loved ones can offer invaluable encouragement during challenging times, so keep them close and make them a priority.

Understanding the reality of startups is essential. Success often hinges on your ability to navigate hurdles. Even the best ideas need strong leadership to thrive.

Planning thoroughly is key. Spend time mapping out every detail of your business and setting a clear path forward. It helps reduce uncertainty and makes decision-making easier.

Do your homework. Research extensively to avoid assumptions. The more you know, the better your decisions will be.

From day one, think about your exit strategy. Having a plan in place will guide your choices and keep you focused.

Not all advice will be relevant to your business. Take what fits your situation and always back it up with your own research.

Be selective with co-founders and investors. The right partners can make a big difference, so choose wisely and do your due diligence.

Be cautious of quick investments. Fast money can seem appealing, but it often comes with strings attached. Think long-term and stay wary.

Manage your equity carefully. Try not to give away more than 10-20% before your seed round ends. Equity is precious and can dilute quickly.

Have a clear ask when seeking funding. Make sure your request is straightforward and that you have a solid plan for the funds.

Aim for a runway of at least 12 months. This will give your startup the time it needs to grow and adapt.

Take time to think through and validate every decision. A thoughtful approach can help you avoid risks and set yourself up for success.

Usability tests are important. Get feedback from various personas to ensure your product meets real needs and can adjust to market demands.

Balancing work and personal life are crucial for long-term success. Keep an eye on your schedule and make time for activities that support your well-being.

Give back to the startup community. Mentoring young entrepreneurs can be incredibly rewarding. Sharing your experience not only helps them but also keeps your own passion for entrepreneurship alive.

TFS: That is some sound advice. What has been the most fulfilling part of your entrepreneurial journey? 

Osama Shawky: For me, the most rewarding part of being an entrepreneur is seeing the real impact our work has on people’s lives. It is incredibly satisfying to know that estaie provides a reliable and comfortable home away from home for so many. Watching our vision evolve from an initial idea into a successful platform and seeing our team grow and thrive is deeply fulfilling. Every milestone we reach reinforces our mission and drives us to aim even higher.

You see, the chance to continuously innovate and push the limits of what’s possible in the travel and accommodation industry is exhilarating. I love being involved in various areas like automation, marketing, SEO, sales, and fundraising. It allows me to use my skills to move the company forward. Mentoring my staff and interns and dedicating time to community work adds another layer of richness to my journey. I believe being an entrepreneur lets me blend creativity, technology, and business sense to make a meaningful difference, and that, I would say, is the greatest reward of all. 

TFS: Mr. Shawky, this conversation has been wonderfully enlightening. Hearing about your journey and the exciting advancements you are making with estaie will surely inspire our readers. We wish you and your team all the best as you continue to push the boundaries and achieve even greater success.

Osama Shawky:

Thank you so much for having me on The Founders Story. It was a pleasure sharing the story of estaie and discussing the exciting developments in our journey.