Airbnb CEO Brian Chesky on early rejection, customer focus & AI’s future in hospitality | E1735 | Summary and Q&A

May 4, 2023
This Week in Startups
YouTube video player
Airbnb CEO Brian Chesky on early rejection, customer focus & AI’s future in hospitality | E1735


Airbnb CEO Brian Chesky shares insights on the challenges faced by the company in its early days and emphasizes the importance of focusing on the customer experience and core service.

Install to Summarize YouTube Videos and Get Transcripts

Key Insights

  • 📺 Rejection and skepticism from investors was a major challenge for Airbnb in its early stages, but the founders remained persistent and focused on their vision.
  • 👤 Focusing on the customer experience and addressing user complaints were pivotal in the company's success and growth.
  • 👻 Chesky's shift in his role as CEO to prioritize product development, marketing, and hiring has allowed for a more cohesive and efficient operation.


now at the time Jason we were trying to raise a hundred and fifty thousand dollars at a 1.5 million dollar post money valuation so for 150 000 you could own 10 of Airbnb and the majority of them didn't even reply to the email I actually end up publishing a bunch of the rejection emails but many people said like this isn't a good idea many people sa... Read More

Questions & Answers

Q: How did Airbnb overcome the initial rejection from investors and become a successful company?

In the early days, Chesky and his co-founder faced numerous rejections and doubts about the viability of Airbnb. However, they remained resilient and focused on building a product that offered value to customers. Eventually, through persistence and showcasing their unique offerings, they were able to secure investments and gain traction.

Q: What were the key challenges faced by Chesky in running Airbnb?

Chesky mentions that one of the main challenges was prioritizing and addressing user complaints in order to improve the customer experience. This required a deep understanding of user feedback, constant iteration, and prioritization of issues.

Q: How does Chesky manage the company's operations as a remote company?

While Airbnb is not a fully remote company, Chesky highlights the importance of flexibility in the workplace. The company allows employees to choose whether they want to work from an office or remotely, depending on their needs. Regular in-person team meetings and retreats help foster collaboration and build team cohesion.

Q: What role does AI play in Airbnb's future plans?

Chesky envisions AI as a crucial tool for personalization and customizing the travel experience for individual users. The goal is to develop robust AI models that can understand user preferences and provide tailored recommendations. Additionally, AI will be applied to improve the application interfaces and facilitate smoother interactions with users.


In this video, Brian Chesky, the CEO of Airbnb, discusses the challenges and successes the company has faced over the past decade. He shares stories of rejection from investors, the importance of focusing on the customer experience, and his approach to prioritizing and addressing user complaints. Chesky also talks about his role as CEO and how he spends his time on product, marketing, and hiring.

Questions & Answers

Q: How did Airbnb overcome resistance and gain consumer acceptance?

Chesky explains that when they first started, many investors rejected the idea of Airbnb and said it wouldn't work. However, through perseverance and providing value to early adopters, they were eventually able to gain consumer acceptance. Chesky emphasizes the importance of focusing on a core group of users who find value in the product, rather than trying to appeal to everyone.

Q: How has Chesky's role as CEO evolved over time?

Chesky shares that initially, he was more hands-off and focused on strategy and capital allocation. However, after facing challenges during the pandemic, he realized the need to be more involved in product and marketing. He now spends most of his time reviewing work, hiring, and ensuring a cohesive roadmap for the company. Chesky believes in having a small, efficient team and maintaining a strong focus on the customer experience.

Q: How does Airbnb prioritize user complaints and address them?

Chesky explains that Airbnb analyzes various inputs, such as customer service calls, social media posts, and user behavior, to identify common issues. They then prioritize based on frequency and severity, as well as identifying connections between different types of complaints. The prioritization process involves both a scientific analysis and an artistic intuition, with a group of team members deeply understanding the issues and using their expertise to make decisions.

Q: Can you provide an example of how Airbnb has addressed user complaints?

Chesky mentions the issue of confusion and complaints regarding pricing. By analyzing feedback from both hosts and guests, Airbnb was able to identify the connection between hosts struggling with pricing and guests feeling that fees were too high. To address this, Airbnb focused on making it easier for hosts to understand pricing and ensure transparency for guests. This example highlights the importance of considering both sides of the marketplace when addressing user complaints.

Q: How does Airbnb maintain focus on its core service before exploring new ideas?

Chesky emphasizes the need for permission from customers to pursue new ideas. He explains that Airbnb focuses on fixing issues and improving its core service before moving on to new initiatives. By listening to customer feedback and addressing their concerns, Airbnb aims to build a strong foundation of customer satisfaction and trust, which in turn will allow for future exploration and expansion into new areas.

Q: How does Airbnb manage its marketing and product development?

Chesky describes Airbnb's approach to marketing and product development as integrating product and marketing teams closely together. Rather than separate departments with different roadmaps, Airbnb ensures that these teams work in harmony to create a cohesive experience for users. Chesky also emphasizes the importance of simplicity and clear communication, aiming to explain complex ideas in a way that busy customers can easily understand.

Q: How does Chesky spend his time as CEO?

Chesky explains that he spends most of his time on product, marketing, and hiring. He reviews work, conducts regular meetings, and focuses on ensuring a high level of quality and cohesiveness in the company's offerings. Chesky also highlights the importance of being directly involved with customers and maintaining an efficient, focused organization.

Q: How does Airbnb decide on new initiatives and features?

Chesky mentions that Airbnb has some big ideas for the future, but they prioritize their core service first. They analyze customer feedback and complaints to identify areas for improvement, and they prioritize features based on the frequency and severity of issues. Airbnb focuses on understanding customer needs and ensuring that they have permission from customers to explore new initiatives.

Q: How does Chesky balance the needs of hosts and guests in addressing complaints?

Chesky explains that Airbnb strives to find a balance between the needs of hosts and guests by analyzing feedback from both sides. By understanding the perspectives and pain points of hosts and guests, Airbnb can identify areas where improvements are needed. The goal is to create a positive experience for both hosts and guests, enhancing the overall value of the platform.

Q: What role does intuition play in prioritizing and addressing user complaints?

Chesky emphasizes the importance of intuition in the prioritization process. While data analysis is essential, it is the intuition and expertise of the team that allows them to make informed decisions. Intuition comes from deeply understanding the issues, considering engineering capabilities, and taking into account various factors such as severity, frequency, and the overall impact on the customer experience. It is an art form that complements the science of data analysis.


Brian Chesky shares insights into Airbnb's journey and the challenges they faced in gaining acceptance and trust from consumers and investors. He highlights the importance of focusing on the customer experience, listening to feedback, and prioritizing user complaints. Chesky also discusses his hands-on approach as CEO, spending significant time on product, marketing, and hiring. By continuously improving their core service and addressing customer needs, Airbnb aims to build a solid foundation for future growth and expansion.

Summary & Key Takeaways

  • Chesky recalls the difficulty in raising funds for Airbnb in its early days, with many investors rejecting the idea and questioning the viability of the travel industry.

  • He highlights the critical role of the customer experience in the success of a startup, and how they prioritized addressing user complaints and improving core services.

  • Chesky discusses the shift in his role as CEO, where he now spends most of his time on product development, marketing, and hiring, while ensuring a cohesive roadmap for the entire company.

  • The company's focus on product and marketing integration has led to accelerated growth and the ability to ship frequent updates and innovations.

Share This Summary 📚

Summarize YouTube Videos and Get Video Transcripts with 1-Click

Download browser extensions on:

Explore More Summaries from This Week in Startups 📚

Summarize YouTube Videos and Get Video Transcripts with 1-Click

Download browser extensions on: