Travel Technology

A 1000-Day Journey: 5 Lessons from Building a Startup Across Continents

Gullie - A startup aiming to simplify the relocation process

The past 1000 days have been an incredibly fulfilling journey of intense work and growth as my team and I built Gullie, a startup aiming to simplify the relocation process for teams by automating the research, personalization, and coordination work of relocation consultants.

My Background

I grew up in Singapore and spent sporadic amounts of time in Malaysia and Australia. I ventured into entrepreneurship at 18 when I co-founded a company that organized nightlife events and helped clients like Pernod Ricard launch their products in Singapore. This early experience led me to join their e-commerce arm in Southeast Asia. I then briefly worked at a venture capital firm before jumping back into the startup scene at a New York-based franchise-tech startup for two years.

My first startup in the travel industry failed when COVID-19 hit. Subsequently, I joined Google as a product specialist, launching Google Shopping in South Asia and took on projects at YouTube and Cloud.

Life after Google has been spent building Gullie. It’s been an adventure that has given me the opportunity to live and work in some of the world’s most dynamic cities—New York, London, San Francisco, Dubai, Riyadh, and Zurich—each bringing its own set of challenges and valuable lessons that have deeply influenced both my personal and professional life.

Key Learnings from My Journey

Observing Trends in Relocation and Talent

In recent years, I’ve observed several key trends in relocation and talent dynamics. Young professionals, particularly Gen Z, are increasingly keen on relocating to enhance their career prospects and gain new experiences. They see relocation as a gateway to personal and professional growth, especially in innovative and dynamic work environments. Tech giants, especially in the Bay Area, are pushing for their engineering and AI teams to work on-site. Companies like OpenAI, Anthropic, and DeepMind emphasize the importance of face-to-face collaboration for fostering innovation and team cohesion. This creates vibrant communities that attract and retain top talent. Additionally, understanding and respecting local cultures is vital for successful integration. In cities like Dubai and Riyadh, immersing oneself in the local way of life helps build meaningful relationships, while business interactions in the West are typically more direct and fast-paced.

Failing Upwards

One of the most profound lessons I’ve learned is our ability to fail upwards – In other words, failure isn’t always a backward movement. Sometimes, failing unlocks even better opportunities we didn’t plan for as long as we execute towards a clear goal. Post-failure, we usually are even more equipped to take on the next challenge since we have learnt valuable skills and knowledge along the way.

Having a clear goal provides a sense of direction and purpose, which transforms the journey into an adventure. For the last three years, mine has been to simplify the process of living and feeling at home anywhere. This vision has driven my efforts in building, pivoting, and picking up relevant skills along the way such as UI/UX design, coding, team, and product management.

Enhancing Luck Surface Area

One concept that has significantly influenced my journey is the “Luck Surface Area,” introduced by Jason Robert. This principle posits that luck is proportional to how passionately you pursue something and how effectively you communicate it to others. Essentially, the more you do and the more you share, the more opportunities you create. This has been a cornerstone of my strategy, driving me to consistently share my progress and engage with a broader community.

The Impact of Environment and Wellbeing on Success

The environment you immerse yourself in, including the people around you, profoundly impacts your mindset and decisions. Throughout my journey, maintaining physical fitness and mental wellbeing has been crucial. I start my day with Pilates at 7 a.m. and regularly attend SoulCycle spin classes. These activities help manage stress and maintain high energy levels, significantly enhancing my productivity and mental clarity.

This focus on health and environment has influenced my choice of cities. I look for big cities with talent density, energy, and drive—hubs where innovation thrives. I seek places that are walkable so I can go for daily walks to think, where I feel comfortable and safe, and where I have a good support network. Surrounding myself with inspiring, driven individuals who push boundaries and pursue excellence has been key to both personal and professional growth.

Poverty is an Anti-Productive Mindset

Adopting an abundance mindset rather than a poverty mindset has been transformative. The difference lies in seeing opportunities for growth and wealth creation, rather than feeling constrained by limited resources. This shift has enabled me to embrace risks and capitalize on opportunities, fostering a momentum that drives continuous growth.

Some may know this as the rich vs. poor mindset. The fundamental difference is that the rich see money as an opportunity, while the poor see it as something to be earned. This mindset shift is crucial for long-term success and growth.

What I’m Working On Now

Leveraging my experiences, I’ve delved into the complexities of relocations and the expat lifestyle. I’ve consulted with over 200 relocatees, HR professionals, and mobility experts to understand every facet of moving, from visas to housing logistics. Additionally, over 2000 global talents have participated in our community events, sharing their diverse experiences.

Gullie was international from its inception. Initially, we concentrated on relocations to Singapore and the US. Now, our focus has shifted to the US and the Middle East, particularly inbound into Riyadh (Saudi Arabia) and San Francisco.

The Future of Relocation with Gullie

The future of relocation looks promising with advancements in AI and supportive global policies. These innovations are set to make the process more efficient, cost-effective, and personalized, thereby helping companies attract and retain top talent.

At Gullie, we harness AI to provide instant personalization and optimization based on hundreds of data points from each individual’s profile. This technology saves time and reduces costs significantly. By tailoring relocation plans to individual needs, AI simplifies decision-making and coordination, alleviating the mental burden and stress typically associated with moving.

For a personalized and seamless relocation experience at a fraction of the cost of traditional consultants, consider Gullie—the one-stop AI platform for efficient talent relocation. Focus on what truly matters when moving to a new country, and let us handle the logistical complexities.

I am eager to witness how these advancements will continue to shape global mobility. The journey has been challenging but immensely rewarding, and I look forward to helping more individuals and companies navigate their relocation journeys with ease and success.

Written By: Rachael Annabelle Yong

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