Building My First Startup: Excitement, Pain, and Failing Foward
Launching my first startup, ICAREUM, was one of the most ambitious projects I had ever undertaken. As a PropTech startup, it was designed to revolutionize the real estate industry in Canada by offering a cloud-based 3D sales enablement platform for commercial leasing and pre-construction developments. After 18 months, over US$500,000 invested, and countless challenges, ICAREUM became one of the worst startup failures in my career. However, as with all failures, the experience provided invaluable lessons that have shaped me into a better entrepreneur and investor.
Climbing Mt Batur in 2020 - Bali, Indonesia
The Inspiration Behind ICAREUM
Like many others during the COVID-19 pandemic, I found myself reevaluating my business goals and life choices. At the time, I was doing business consulting for a firm in Guangzhou, China, while remotely managing my real estate investment portfolio in Canada. In February 2020, after visiting a family member in Melbourne, Australia, I made a decision to hunker down in Bali, Indonesia, for what I thought would only be a few weeks while the “Wuhan thing” blew over. However, those few weeks quickly transformed into six months as the pandemic snowballed, with lockdowns and travel restrictions becoming the norm across the globe.
During my extended stay in Bali, I met my co-founder, a full-stack developer and BIM (Building Information Modeling) designer. He had already been working on a real estate platform called ICAREM, and through our conversations, it became clear that we shared a common vision for the future of real estate. We both recognized the potential to transform the market by integrating immersive technology with pre-construction condo sales. The idea of a cloud-based 3D sales enablement platform quickly took shape, enabling real estate professionals to offer virtual 3D property tours to potential buyers and tenants from anywhere in the world. With the global shift to remote work and a burgeoning demand for virtual experiences, we believed that this technology was not just relevant but essential for the future of real estate.
Step 1 — Excitement
The Real Estate Market Opportunity
The premise behind ICAREUM was simple yet powerful: to create a tool that would allow commercial developers and real estate brokers to showcase their properties through an interactive, online 3D experience. Potential tenants could walk through virtual buildings, view unit details, and explore entire neighbourhoods—all from the comfort of their devices. The pandemic had rapidly accelerated the real estate market’s shift towards digital solutions, and we saw ICAREUM as a potential game-changer in how properties were marketed and sold.
In a world where physical site visits had become nearly impossible, virtual experiences were no longer a luxury but a necessity for survival. We envisioned ICAREUM as the go-to platform for real estate professionals to engage clients remotely, driving faster and more informed decision-making. Whether it was showcasing office spaces, retail units, or residential developments, our platform aimed to revolutionize property sales in a way that was timely and aligned with market demands.
Building the ICAREUM Team
With our vision set, the next logical step was building a team to help us turn this concept into reality. My co-founder brought his technical expertise in software development and BIM, while I contributed my experience and understanding of the real estate market, investment, and finance. Together, we began to recruit talented individuals who shared our passion and enthusiasm for disrupting the real estate industry with cutting-edge technology.
Assembling the right team was crucial to the success of our startup. We sought people who had the technical and industry knowledge and believed in the transformative potential of the product we were building. We were excited by the talent we managed to attract—developers, marketers, game designers, and strategists who were just as eager as we were to bring ICAREUM to life. We envisioned our platform becoming a disruptive force in the PropTech space, driving innovation in how properties were marketed and sold.
The Early Momentum and Positive Feedback
The early days of ICAREUM were filled with excitement and momentum. As a first-time tech startup founder, I was exhilarated by the possibilities and the buzz surrounding our project. By the Winter of 2021, we started sharing demos of our 3D platform with potential clients, many of whom were commercial developers and brokers looking for new ways to adapt to the post-pandemic market. The feedback we received was overwhelmingly positive—clients were impressed with the immersive capabilities of our platform, and several expressed keen interest in integrating it into their real estate sales processes.
Our social media presence, particularly on LinkedIn, began to gain traction as we generated buzz around ICAREUM. We attracted the attention of strategic partners, and it genuinely felt like we were on the verge of a breakthrough. At this stage, our burn rate was relatively modest, around $10,000 per month, and we managed our resources carefully as we continued to develop the platform. The early momentum gave us the confidence that we were on the right track, and the feedback we received only reinforced our belief that ICAREUM had the potential to revolutionize the real estate industry.
Step 2 — The Pain
The First ICAREUM Office - September 2020
Leadership Struggles Begin
By Spring 2021, the initial excitement started to fade as the MVP launch continued to be delayed and cracks began to form in the leadership team. A major issue was the lack of clearly defined roles and responsibilities. The shared vision that once united us unravelled, creating tension between key team members. As I later shared with my team:
"The roles and responsibilities that executives are held accountable to are infinitely more important than the titles they hold. At ICAREUM, we never completed a clear set of roles and responsibilities or an accountability matrix for our leadership and team members. This turned out to be a big mistake."
Without clear accountability, it became difficult to maintain alignment, and conflicts began to arise. We tried to address these issues, but by the time we realized the extent of the problem, it was too late.
The Pitfalls of Not Validating the Problem
One of the biggest lessons I learned from ICAREUM’s failure was the importance of focusing on solving a problem, not just building what you think is the solution. In September 2020, we believed we knew what the market needed: a 3D virtual tour platform for real estate. However, we hadn’t spent enough time validating that assumption with our target customers or fully understanding the nuances of the sales process.
"Stop building a solution for a problem that you don’t fully understand." — Every successful startup Founder, ever.
This advice, which I received from nearly every successful tech entrepreneur I spoke to, was a crucial lesson that I learned too late.
By April 2021, we had developed what we thought was our first MVP—an iOS app. In reality, it was more of a prototype or proof of concept. Despite the positive feedback we received, we failed to pause and ask the hard questions: Was there enough demand for this product? Was it scalable? Could we effectively sell it? These oversights would come back to haunt us later on.
Rapid Burn Rate and Financial Missteps
With our bit of traction, I decided to accelerate development and get to a fully working web application and improved iOS app. Our burn rate tripled from US $10,000 to $30,000 per month. We built out a design studio and a 3D team, hoping to scale up our product to launch an MVP by September 2021. I ignored the advice of many seasoned entrepreneurs who warned me not to dive into full-scale development without first validating the problem we were trying to solve. In hindsight, I see now that I was too focused on getting to market and didn't spend enough time on customer discovery.
This rapid escalation of expenses without a clear customer pipeline or enough time to generate sales was a huge financial misstep. The more money we spent, the more pressure we felt to launch something quickly. But we hadn’t spent enough time validating whether the market actually wanted what we were building, and real estate developers were notorious for being hard to reach and slow decision makers.
Lack of Defined Roles and Accountability
One significant issue was the leadership divide between my Co-Founder and our CTO. Despite our efforts to patch things up in September 2021, it was too late—the damage had already been done. One of my biggest mistakes was not sharing equity and creating a vesting structure with key talent early on. Two critical team members, Ivan Tyumenyev and Mark Korotin, joined our leadership discussions about four months before the end, but we should have involved them much earlier. They both brought valuable experience that could have helped us make better decisions, but the team was already fractured by the time we included them.
Communication Breakdowns: A Growing Concern
In the early days of a small startup, accountability and communication can happen naturally because you're sitting right next to your Co-Founder, hashing out details as they arise. However, as ICAREUM grew and more moving parts were added to the operation, keeping everyone focused on the same goals became much harder. By April 2021, we had some early success with our iOS app but struggled to maintain momentum. Communication between the leadership team started to break down, and our lack of unity made it impossible to deliver a web MVP by September or do the customer discovery work needed to succeed.
Step 3 — Failing Forward
Early Start Architectural Visualization Work in Unreal Engine 4 - Toronto Skyline
The Final Decision to Pull the Plug
By October 2021, it became clear that ICAREUM was floundering. I had already slashed expenses back to US $10,000 monthly and dissolved half of the team, hoping that we could salvage something from the venture. However, after another month of unproductive work and the slow season for business development coming up, I had to make the difficult decision to pull the plug.
Key Lessons Learned From My First Startup Failure
Reflecting on ICAREUM’s journey, it became clear that several critical mistakes contributed to our downfall. Leadership conflicts, undefined roles, and insufficient market validation were key factors. While hindsight provided clarity, by the time we recognized these issues, trust had been eroded, our burn rate was uncontrollable, and financial resources were depleted. Despite its failure, ICAREUM turned out to be one of the most valuable learning experiences of my career, teaching me lessons that have since shaped how I approach future ventures.
1. Start with the Problem, Not the Solution
One of the fundamental errors we made was rushing into product development without fully validating the problem we aimed to solve. It’s easy to get excited about building a solution, but without understanding the market’s real pain points, you risk creating something nobody needs.
Validate assumptions with real customers early in the process.
Focus more on customer discovery and less on the initial product.
Continuously reassess your problem-solution fit to ensure it remains relevant.
2. Roles and Responsibilities Matter
The lack of clearly defined roles and accountability led to inefficiencies and confusion, which hurt our overall execution. As the company grew, these issues worsened, as people didn’t know who was responsible for key tasks.
Clearly define roles and create an accountability matrix from day one.
Adjust responsibilities as the company scales and new challenges emerge.
A well-structured leadership team ensures smoother operations and better decision-making.
3. Communication is Critical
As ICAREUM grew, maintaining clear communication became more difficult, leading to misunderstandings and misalignment. Without open, transparent communication, team cohesion starts to break down, causing delays and missed opportunities.
Set up regular check-ins and use structured communication tools like Slack or project management software to ensure everyone stays on the same page.
Prioritize transparency in decision-making and project updates to keep the entire team aligned.
4. Ego is the Enemy
Personal pride and ego can prevent leaders from making hard but necessary decisions. In our case, egos sometimes got in the way of admitting mistakes and pivoting when needed, which hindered progress.
Focus on the bigger picture and the company’s success rather than personal accolades.
Encourage a culture of humility, where admitting mistakes and learning from them is seen as a strength, not a weakness.
5. Failure is Part of the Process
While ICAREUM didn’t succeed, the experience taught me that failure is a necessary part of entrepreneurship. Every failure brings with it a new set of lessons and insights that prepare you for future successes.
Embrace failure as an opportunity to grow and refine your approach.
Use each setback as a stepping stone toward a more sustainable, successful business model.
These lessons, although learned the hard way, have profoundly influenced my approach to future projects and have made me a more resilient and thoughtful entrepreneur.
What I Would Do Differently Next Time
1. Define Roles and Responsibilities Early On
If I could go back and do it all over again, I would have placed a stronger emphasis on clearly defining roles and responsibilities from the very beginning. Having this structure would have helped the team stay aligned, avoided unnecessary leadership conflicts, and created a more focused work environment. A well-defined framework would have allowed everyone to understand their accountability and contribution to the company's success.
2. Focus on Market Validation Before Product Development
One critical change would be to spend far more time validating the problem with potential customers before diving into product development. We should have been engaging with potential clients to truly understand their needs and pain points. This approach would have ensured that we were building something that solved a real issue in the market, saving us from wasted time and resources.
3. Control Cash Burn to Extend Runway
Another significant adjustment would be controlling our cash burn. Instead of allowing expenses to escalate quickly, I would have worked to keep the burn rate between $5,000 and $10,000 per month. This would have extended our runway from 18 months to over 60 months, giving us ample time to refine our product, pivot if necessary, and gain the traction needed to raise capital or achieve steady growth.
4. Empower Team Members Through Equity and Vesting
Lastly, I would have been less focused on retaining equity for myself and more focused on incentivizing key team members with a clear vesting and accountability structure. Offering equity tied to performance would have motivated the team and aligned everyone’s goals with the company’s success, driving stronger long-term commitment and overall performance.
Step 4 — Moving On
Jolly Harbour, Antigua and Barbuda
Relocating to the Caribbean
Despite the failure of my first startup, ICAREUM, it served as a catalyst for new beginnings in ways I hadn’t foreseen. Although filled with challenges and, ultimately, failure, the journey of building and growing ICAREUM offered an unparalleled education in the world of tech startups, leadership dynamics, and managing the rollercoaster ride of entrepreneurship and investing. While ICAREUM didn’t succeed as we envisioned, the experience profoundly shaped my personal and professional growth.
Ironically, this failure unlocked opportunities that I may not have pursued if the startup had succeeded. One of the most significant outcomes was my decision to leave Canada permanently and relocate to the Caribbean—a decision that wouldn’t have happened without the learning experience that ICAREUM provided.
Liquidating My Real Estate Portfolio
After living and working in Bali for six months—surrounded by a dynamic community of digital nomads, innovators, and fellow entrepreneurs—I began to see the world and my place in it differently. My mindset had shifted dramatically from the experience of running ICAREUM. It showed me that opportunities for growth and investment existed far beyond the borders of Canada and the North American markets I had previously focused on. I’d been researching places to live and invest for many years, but the Caribbean, in particular, stood out for me as a region rich with potential in both real estate investment and lifestyle.
This was more than just a physical relocation; it was a strategic pivot. I recognized the unique, untapped opportunities in the Caribbean, where I could apply my skills in real estate investment and business strategy. In light of this new vision, I decided to liquidate 90% of my real estate portfolio in Canada. Between 2021 and 2022, I sold my holdings at the perfect time, benefiting from frothy market conditions. The decision to sell was partly luck—but also a combination of great advice from people around me, a deep understanding of market conditions, and the entrepreneurial instincts I had developed.
Looking back, the experiences during those difficult 18 months taught me to recognize when to pivot, when to seize opportunities, and when to take calculated risks. Had it not been for the failure of ICAREUM, I may not have had the clarity or confidence to make the bold decisions I made. The experience of relocating to the Caribbean and liquidating my Canadian real estate assets was the beginning of a new chapter in my life, one that allowed me to leverage the lessons I learned from ICAREUM and apply them to a new context.
New Opportunities in the Caribbean
While the failure of ICAREUM was both financially and emotionally costly, it proved to be one of the most valuable learning experiences of my career. It thrust me into the world of technology and startups, providing insights I wouldn’t have gained through traditional real estate ventures alone.
ICAREUM’s collapse taught me the importance of market validation, strong leadership, and vision alignment—lessons that have become foundational to how I now approach new business opportunities. This experience was a crash course in resilience, teaching me how to manage a public failure and adapt quickly. These skills have proven critical as I’ve navigated new opportunities in the Caribbean, where I’ve been able to apply my knowledge of technology, real estate, and business strategy to more sustainable ventures. ICAREUM’s failure wasn’t a door closing but an opening to an entirely new set of possibilities.
Conclusion
ICAREUM may have been one of the worst startup failures in my career, but it was also one of the most transformative experiences. The lessons I learned about leadership, accountability, market validation, and team management continue to shape how I approach my business ventures today.
Without ICAREUM, I wouldn’t have had the insight to make critical decisions about my real estate portfolio nor the confidence to relocate to the Caribbean and pursue new ventures internationally. In the end, failure wasn’t a dead end — but a stepping stone toward greater opportunities. Every setback has taught me something new, bringing me closer to my next success. These failures and learnings aren’t just part of my story—they are what drive me toward continued growth and success.
Appendix
ICAREUM Pitch Deck — September 2021
ICAREUM Promo Video April 1st, 2024
Bio
Caribbean Real Estate Investor and Entrepreneur — Founder @Offshore Freedom | Host of the @CaribbeanRealEstatePodcast
We help successful investors and entrepreneurs live and invest in the Caribbean and buy real estate internationally.
Schedule a 1 on 1 consultation with Dan Merriam, and let him help you design the life of your dreams and achieve Offshore Freedom™. Ask questions and get answers about lifestyle design, tax planning, banking, international real estate, second residencies, or citizenship by investment.
Writer in Tax Reduction, International Tax Planning, Citizenship by Investment, Caribbean, Technology Startup, Failing Forward, Real Estate Tech, Proptech, Contech, Unreal Engine 5, Artchitectual Visualization, Digital Twin, 3D Sales Enablement, Virtual Reality, Asset Management, Lifestyle Planning, Company Formation, Offshore Banking, Asset Protection, Technology, Entrepreneurship
This article is for informational purposes only; it should not be considered financial, tax planning or legal advice. Consult a financial or investment professional before making any major financial decisions.
