‘Run your company unapologetically’ – Maltese Founder shares insights from Y Combinator

James Zammit, Co-founder and CEO of Roark, recently shared key takeaways from a talk by Airbnb Co-Founder and CEO Brian Chesky at a Y Combinator dinner.

Mr Zammit’s Start-Up, Roark, has recently been accepted into Y Combinator’s Winter 2025 batch. This marks a significant milestone for the Maltese entrepreneur and his Co-Founder, Daniel Gauci Mizzi, as they embark on a journey to revolutionise AI-driven voice interactions.

Reflecting on the discussion, he noted that Mr Chesky’s insights were not just lessons but powerful reminders of what truly matters when building a great company.

One of the standout messages from Mr Chesky’s talk was the importance of obsessing over details. “As a founder, you’re the person who can move the needle the most,” Mr Chesky emphasised. He argued that deep involvement in the details is not micromanagement but leadership, as founders set the standard for their teams.

Mr Zammit echoed this sentiment, pointing out that a leader’s commitment to excellence directly influences the company’s culture and expectations.

Mr Chesky also underscored the need to run a company unapologetically. According to Mr Zammit, Mr Chesky’s perspective is that “not everyone needs to like you. Respect > approval.”

Founders should focus on building the company they believe in, rather than one shaped by external opinions. Conviction in one’s vision, Mr Chesky argued, is what attracts the right people.

Another critical lesson from the talk was that startups die from suicide, not homicide. “Most startups fail from within, not from competition,” Mr Chesky stated, recounting how Airbnb’s co-Founders maintained weekly alignment meetings for 17 years to prevent internal conflicts.

Mr Zammit found this particularly striking, noting that prioritising the best idea over personal egos is essential for long-term success.

When it comes to hiring, Mr Chesky advised founders to hire experts, not managers. “Your first hires define your company’s DNA,” he said.

He stressed that engineering leads should be exceptional engineers, and design leaders should be visionary designers. Mr Zammit resonated with this, highlighting the need to maintain high hiring standards, as each employee sets a precedent for future hires.

Mr Chesky also challenged conventional wisdom on organisational structure, advocating for growing in one direction. Rather than dividing teams by domain or feature, Airbnb keeps them functional – engineering, design, etc. – and aligns everyone around a single roadmap. This unified focus prevents internal competition for resources and fosters cohesion.

Another principle Mr Chesky championed was to chase love, not likes. He referenced a well-known Paul Graham quote, who is one of the Co-Founders of Y Combinator: “100 users who love you are worth more than 1 million who just like you.”

Mr Chesky advised founders to design experiences as if aiming for an impossible 10-star service and then scaling back to something feasible. Mr Zammit described this as a powerful approach to customer loyalty and product excellence.

The importance of choosing investors wisely was another key takeaway. “When shit hits the fan (and it will), you need investors who have your back – not just the highest valuation,” Mr Chesky warned.

He reminded founders that board members become bosses they cannot fire, so selecting investors who provide guidance in tough times is crucial. Mr Zammit reinforced this idea, stressing that investor relationships should be based on more than just financial backing.

Finally, Mr Chesky advised founders to do the ‘unscalable’ strategically. Personal user interviews, handwritten notes, and temporary fixes may seem inefficient, but they build empathy and yield insights that no algorithm can replace. “By all reasonable measures, Airbnb shouldn’t have worked,” he admitted, yet perseverance and unconventional approaches made the company what it is today.