He Sold His First Startup For Over $100 Million, Helped Raise $600 Million For His Second, And Now Is Bootstrapping An AI Startup

Embarking on the entrepreneurial journey is much like navigating uncharted waters. It’s a thrilling yet challenging expedition that demands unique skills and insights. Conversation with seasoned entrepreneur Pablo Fernandez Alvarez gave us several invaluable lessons.

Each of these lessons gives you insights into startup culture and business endeavors. From the critical importance of cultural fit in hiring to the wisdom of prioritizing profitability from day one, this DealMakers episode delves into Pablo’s entrepreneurial acumen.

Read ahead to know more about Pablo’s fascinating journey from Madrid to Miami, exploring the highs and lows, the successes and challenges, and the invaluable lessons learned along the way.

Listen to the full podcast episode and review the transcript here.

Growing Up in Madrid – Early Childhood

In the heart of Madrid, Pablo Fernandez Alvarez began his journey as an entrepreneur, guided by a sense of adventure and a willingness to take risks. Born into a family of six siblings, Pablo’s story unfolds through cities, cultures, and careers since his family moved around a lot.

Pablo studied international relations at the University of Madrid and then started his career in the traditional consulting field at The Boston Consulting Group in their Madrid Office. Next, he moved to the US to navigate the fast-paced world of New York’s investment banking.

Pablo’s transition from Madrid to New York was more than just a change in location; it was a cultural shift. The hustle and speed of the New York subway, coupled with the American dream, left a lasting impact.

The absence of hierarchy and bureaucracy in the U.S. work culture opened Pablo’s mind to think beyond the confines of Spain.

Pablo worked at large Spanish banks and later became the head of strategy at Santander Holdings USA in the Greater Boston Area.

Lessons from Consulting and Investment Banking

As Pablo ventured into consulting and later investment banking, he realized the importance of work ethics and effective communication. His experiences at BCG shaped not only his problem-solving skills but also his approach to entrepreneurship.

He learned how to break bigger problems into smaller ones and then tackle them.

Pablo observed that the firm’s founders had similar backgrounds and went into consulting, investment banking, private equity, or venture capital. They were also open to venturing into known territory.

The network Pablo built during his consulting days would later become a valuable asset in his entrepreneurial journey. He also honed his work ethics, communication skills, and ability to convince people of his ideas using PowerPoint and compelling presentations.

Harvard, Entrepreneurial Ambitions, and the American Dream

Pablo’s pursuit of entrepreneurial dreams faced setbacks during his university years, but the spirit persisted. His decision to pursue an MBA at Harvard marked a turning point. Having acquired his degree, Pablo was offered the position of Head of Strategy with a great salary at Banco Santander.

He became a part of the board of directors and the executive community of a 30,000-person company. Immersed in the U.S. business environment, he witnessed the essence of the American dream – a stark contrast to the beliefs prevalent in Spain.

The absence of hierarchy and a focus on meritocracy fueled his desire to think bigger and venture into the unknown.

Clicars – A Journey from $0 to $500 Million

With lessons from consulting, investment banking, and the American dream, Pablo co-founded Clicars, an online used car e-commerce platform. From humble beginnings in a Madrid garage to a multi-million euro enterprise, Clicars grew exponentially.

Pablo talks about how, sometime in October 2015, he approached the senior executives of Santander and told them that he was ready to start his own business. Pablo quit his job but walked away with an initial investment of $0.5M that the one of his colleagues offered.

Returning to Madrid, Pablo went to the notary and told them he wanted to start a company. Next, he wanted to print a pitch deck to reach out to early investors but found the place closed. This came as a culture shock since he was more used to the fast-paced American way of working.

At the same time, Pablo was able to find the ideal product-market fit quickly enough. They started working in a small garage, paying a rent of €700 per month, possibly the cheapest place in Madrid.

In the first year of opening his business, Pablo made $5.46M; in the second, they made $15.28M. Within 6 years, Clicars had earned a written revenue of $545.73M. Since they were making good money, Pablo did not need to raise substantial funding.

They raised $1.09M in the seed round and then $4.37M in the series A in the first year.

Its profitability-focused approach set Clicars apart, challenging the conventional belief that hyper-growth required constant dilution. The story of Clicars exemplifies the possibility of rapid growth while retaining control. Pablo and his co-founder still own 70% of the business.

Exiting Clicars for $100 Million

Pablo looks back to renting the cheapest offices in Madrid since they didn’t have any salary. The duo even paid their own travel expenses, making every Euro count.

As Pablo explains, since he was an investor himself before becoming an entrepreneur, he understands the value of retaining control of their companies. Being profitable was the only way to guarantee independence and remain in control of their destiny.

Pablo and his co-founder were determined not to fall into the trap of raising so much funding that someone had to buy them out. That’s how they were able to sell their first company for $109.15M.

At the same time, founders should also know the opportune time to make an exit so they can create more companies.

Clikalia – Scaling Real Estate Ventures

Empowered by Clicars’ success, Pablo and his best friend Alister embarked on a new journey – Clikalia. Here Pablo became an investor and also the chairman of the company. Scaling real estate transactions, they emphasized the importance of cultural fit when hiring. Soon, they were selling around 1600 houses annually and earning $261.95M in revenues.

They company started with $1.09M of their own money. However, since buying real estate involves significantly more funding, they raised money from external investors. They started off with $109.15M in series funding and then $436.58M in debt financing.

Eventually, the company raised a total of $654.87M in capital, $218.29M in equity, and $436.58M in debt. Their commitment to values and culture allowed them to retain the same management team even after significant growth.

Clikalia became another testament to their ability to build successful ventures.

Storytelling is everything, which is something that Pablo Fernandez Alvarez was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here), where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

Pablo explains that he prefers mentoring and coaching as opposed to hiring outsiders.

The culture of developing people internally has become a successful initiative; they hire younger and less experienced team members and pay smaller salaries but invest in training and promoting them to executive positions.

Clidrive – Financing Cars and Ownership

Pablo’s third venture, Clidrive, took a unique turn. Focused on car financing, Pablo opted for full ownership, resisting the urge to raise external funds. This decision offered him the freedom and flexibility to run the business according to his vision.

Clidrive’s success, achieved within a year, defied the traditional notion that growth required constant fundraising. Pablo bootstrapped the company using a few million Euros of his own money. The company went from $0 to 10915M in revenues with a workforce of just 50 people.

The Fourth Venture – Clibrain and Lessons Learned

Undeterred by the challenges, Pablo embarked on his fourth venture, Clibrain, an artificial intelligence company. It helps companies turn unstructured data into ready-to-use data and operates with a workforce of just eight people.

Here, Pablo applied the lessons learned from his previous ventures, emphasizing patience, customer focus, and the importance of enjoying the entrepreneurial journey.

Pablo’s approach to bootstrapping and maintaining a long-term perspective shines through, reinforcing the idea that success is a marathon, not a sprint. He has invested $2M of his own money into this venture.

Pablo’s Open-Sea Odyssey – A Metaphor for Entrepreneurship

Beyond the boardrooms and offices, Pablo’s passion for open-sea swimming adds a unique layer to his entrepreneurial story. The challenges he faced in the vast ocean became metaphors for the hurdles in business.

Pablo is holder of 5 Guinness World Records in Marathon Swimming, including The Longest Ocean Swim (250km) and The Fastest 100km unassisted Ocean swim for which he was two times nominated by the World Open Water Swimming Association for “Performance of the Year” and “Man of the Year” Award.

The disciplined, one-stroke-at-a-time mindset he developed in swimming translated seamlessly into his entrepreneurial journey, offering insights into perseverance, goal-setting, and overcoming obstacles.

Conclusion

Pablo Fernandez Alvarez’s entrepreneurial journey from Madrid to Miami is a testament to resilience, adaptability, and the unwavering pursuit of dreams. From navigating cultural shifts to building successful ventures, Pablo’s story serves as an inspiration for aspiring entrepreneurs.

His emphasis on ownership, cultural fit, and a customer-centric approach provides valuable lessons for those navigating the dynamic landscape of entrepreneurship.

As Pablo continues to break records in business and open-sea swimming, his journey reminds us that success is not just about the destination but the extraordinary journey to get there.

Listen to the full podcast episode to know more, including:

• Focus on hiring individuals with the right values and cultural fit rather than relying solely on experience, ensuring a positive and cohesive team dynamic.
• Consider building a profitable mindset early on, as it not only aids sustainability but also provides flexibility and control over the direction of the business.
• Serial entrepreneurs should acknowledge the consistent underestimation of the challenges involved in starting a new business and be prepared for the ongoing demands of each venture.
• When faced with overwhelming challenges, break them down into smaller, manageable milestones, adopting an “act small, think big” approach to stay focused on incremental progress.
• Recognize that building a successful business takes time, and balancing patience with ambition is crucial for long-term success.
• Prioritize customer satisfaction over external funding at the initial stages, making clients the primary source of capital to maintain control and ownership of the business.
• Embrace the entrepreneurial journey, understand that challenges are inevitable, and find joy in overcoming them, steering the business with a sense of purpose and resilience.

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