This video covers a talk by Airbnb co-founder Brian Chesky at YC (Y Combinator) about the difficulties he faced as CEO and the management philosophy he calls 'Founder Mode' that he developed to overcome them. It offers practical advice on tackling organizational inefficiencies that come with company growth, restructuring the organization, and how Founder Mode enables deep attention to detail, hiring top talent, and retaining them.

1. The Origins of Founder Mode: A CEO's Struggles

Brian Chesky recalls that while Airbnb's rapid growth from 2009 to 2014 was exciting and fun, the following six years were "terrible." He notes that while founders may be born, great CEOs are not—most CEOs are terrible at first. He particularly criticizes the advice from Harvard Business School and others that "great leaders hire great people and empower them to do their jobs," which he says can actually ruin a company.

He describes how Airbnb's matrix organization led to infinite team creation, with each team spawning sub-teams that maximized inefficiency. For example, as requests to the graphics team surged and wait times grew, individual teams started creating their own graphics teams, resulting in 5-10 graphics teams. This replicated across tech, product, and data teams, leading to roughly 100 teams all heading in different directions.

This fragmented organization caused several problems:

• Deepening bureaucracy: Meetings about meetings multiplied, with metrics and strategic priorities becoming the only thing holding the company together.
• Loss of product vision: A cohesive product roadmap disappeared as everything focused on short-term goals.
• CEO disconnection from product: The CEO drifted away from the product, losing understanding and control over the company's core asset. Chesky emphasizes that "every CEO, with few exceptions, should be the company's chief product officer (CPO)."
• Politics and lack of accountability: Competition for resources between departments led to politics, and lack of accountability drove talented people to leave.
• Incompetent managers: Managers lacked expertise in the work they managed, causing inefficiency. He says "Airbnb has not a single 'manager'" and that managers must know how to do the work they oversee.

In 2019, deeply frustrated with the situation, Chesky met Apple's industrial design chief Jony Ive and creative director Hiroki Asai, learning how Steve Jobs ran Apple—a major revelation. But with Airbnb's IPO approaching, sweeping changes were difficult. Then COVID-19 hit, wiping out 80% of Airbnb's business in eight weeks. He treated this crisis as "too good to waste" and decided to rebuild the company from scratch.

2. Core Principles of Founder Mode and Organizational Restructuring

Chesky used the crisis as an opportunity to fundamentally reorganize the company.

2.1. Organizational Structure Changes

• Shift to functional organization: Moved from the divided structure back to functional teams—design, engineering, product management, marketing, sales.
• Small, elite teams: Following Jobs's view of teams as special forces, Airbnb adopted a "Navy SEALs, not Navy" mentality with small, highly skilled teams. He said: "Every person generates communication costs. The reason there are too many meetings is too many people. The best way to eliminate meetings is to reduce headcount."
• Eliminating management layers: Removed management layers so only domain experts could manage. "The head of design must actually manage design work. It's not about managing people—it's about managing people through the work."
• Strengthening product marketing: Created a 'product marketing' function combining product management with outbound marketing, inspired by Apple. Product managers were transitioned to product marketers or program managers, combining deep product understanding with storytelling ability.
• Elevating design: Elevated the design department and improved the relationship between engineering and marketing (or sales) to strengthen collaboration between product creators and sellers.

2.2. The Core Principle of Founder Mode: Detail-Oriented Leadership

Chesky emphasizes that the core of Founder Mode is "focusing on details."

"Great leadership is not absence but presence."

He argues that hiring great people and trusting them isn't enough—leaders must be deeply involved in the details. Like a golf instructor who watches every swing to help build muscle memory, a CEO must be deeply engaged from the start to build trust and help teams succeed on their own. Many companies hire executives and hand everything off, only to realize a year later that everything went wrong.

3. The CEO's Practical Operating Style: Reviewing Everything

Chesky mentions that great leaders like Steve Jobs, Elon Musk, Jensen Huang, and Walt Disney all reviewed all work as chief product officers. He does the same for every customer experience at Airbnb.

• Regular review cadences: Reviews happen weekly, biweekly, every 4 weeks, 8 weeks, 12 weeks, or quarterly for areas like customer service.
• The importance of product sense: If a CEO has excellent product sense and judgment, they should review all work their way. If not, they may not be right for the CEO role.
• Launch-based development: Airbnb develops software like hardware with 'product launches.' This addresses how the flood of data and continuous deployment can erode cohesive product vision and weaken centralized quality standards.
• The 'stacking bricks' concept: Like Jobs's 'stacking bricks,' rather than small individual improvements, multiple teams collaborate on big launches for synergy and marketing momentum.
• Deadlines and frequent reviews: The best way to get people to work hard is "set ambitious launch deadlines and check in weekly."
• Deep audits: Every 1-2 years, conduct 2-4 week deep audits of each department to seek fundamental improvements. Creating a safe environment for employees to honestly surface problems is crucial.

4. Hiring and Evaluating Talent for Founder Mode

Chesky says it's critical to determine whether someone accustomed to 'manager mode' can succeed in 'founder mode' when hiring externally.

4.1. Causes of Hiring Failures and Solutions

• Hiring people at the wrong stage: The biggest cause of executive hiring failures is hiring people at the wrong stage. Someone comfortable with management tasks and political bureaucracy will likely fail in a hands-on startup environment.
• Tracing back from results to people: Following Jobs's advice, rather than resumes or prestigious brands, first ask "What product do you admire?" then investigate "Who actually built that product?"
• In-depth interviews: Ask "how did you do it" with at least two follow-up questions to get a third answer. The first answer may be rehearsed, but by the second and third questions, lack of detail reveals authenticity.
• The importance of reference checks: Chesky values reference checks more than interviews. Executives are skilled at packaging themselves in interviews—it's like "a white belt fighting a black belt."
  • 8-hour reference checks: Andreessen Horowitz recommended 8 hours of reference checking per hire.
  • Building talent networks: Don't rely solely on job postings. Continuously ask "Who are the best people?" and get referrals from them.
  • Verifying references: Confirm whether the person providing the reference is themselves an 'A-player.' Remember: "B-players call other B-players great."
  • Encouraging honest feedback: Clearly state that "everything is confidential and your name won't be mentioned" to encourage candid feedback.
  • Specific questions: Ask questions like "What should I watch out for?" and "What development areas would you recommend?" Then ask "Who's the best person you've ever worked with?" to indirectly gauge whether the candidate is truly exceptional.

4.2. CEO's Involvement in Hiring

• Interviewing every candidate: Chesky personally interviewed the first 400 employees. His "biggest regret" is not interviewing the first 1,000. He half-jokingly says CEOs should interview every candidate until the recruiting team revolts and everyone threatens to quit.
• Co-hiring direct reports' direct reports: Chesky co-manages hiring for his direct reports' (executives') direct reports (VP-level). He says "if you can hire someone without me, they're not good enough"—if the team can bring people in without CEO involvement, they're not aiming high enough.
• Growth experience: Check whether candidates worked at growing companies and whether they actually built something. People from old, stagnant corporations may be accustomed to politics and bureaucracy and may not fit a startup.
• Never outsource reference checks: Reference checking should never be outsourced.
• 'Guilty until proven innocent': Approach hiring with the mindset that "every potential candidate is guilty until proven innocent." Look for people with 'spiky' strengths in specific areas rather than people with no weaknesses.

5. Internal Promotion vs. External Hiring

Chesky explains the criteria for deciding between internal promotion and external hiring.

• 'The pitcher never leaves the mound': People never say they're not capable enough, and they don't pick up on hints.
• Conflict avoidance: Most leaders tend to avoid conflict and are reluctant to tell employees they're underperforming. But remember: "Everyone says they waited too long to fire someone, but no one says they fired too fast."
• Capability scaling indicators:
  • Under-capable: If someone is doing what should have been done 6 months ago, they're behind.
  • On par: If they're doing what needs to be done now, they're adequate.
  • Exceptional: If they're doing what needs to be done 6 months from now, or proactively identifying problems, they're exceptional.
• Ability to recruit talent: No matter how good someone is at their own job, they can't achieve peak performance without the ability to recruit great talent. Elevating the team's talent level is essential.
• Trust your gut: If someone consistently frustrates you, trust that instinct. The trend of underperformance reverses only 1 in 10 times.

6. Attracting Talent and Closing Hires at Small/Unknown Companies

When asked how Airbnb attracted talent back when it was small, unknown, and controversial, Chesky responds:

6.1. Talent Attraction Strategies

• Leveraging networks: Used the YC network to recruit YC alumni engineers as early members, rather than targeting people from Google, Meta, or Apple.
• Constant networking: Instead of conferences ("fake work"), constantly networked where talented engineers, designers, and product people gathered.
• Storytelling: Continuously shared the company's story and dedicated enormous time to recruiting. CEOs of high-growth companies should spend 50% of their time on hiring.
• Leveraging investors: Used investor networks to attract talent.

6.2. Closing Techniques

• Convincing candidates NOT to join: At the final stage, he actually explains "every reason you shouldn't work here."
  • "You'll work the longest hours."
  • "We'll hold you to higher standards."
  • "You'll work day and night." This honesty builds trust and attracts top talent who want challenge. He references Ernest Shackleton's famous job ad ("Men wanted for hazardous journey. Small wages, bitter cold, months of complete darkness, constant danger, safe return doubtful. Honor and recognition in case of success.") to illustrate that the best talent craves challenge.
• Investing significant time: Spend substantial time with candidates, showing them you genuinely want them to join.
• Enlisting trusted people: Ask people the candidate trusts to call and speak positively about the company. Chesky mentions how Marc Andreessen had eBay founder Pierre Omidyar and Facebook founder Mark Zuckerberg call him to help close.
• Showing potential: Tell candidates "I see potential in you that you don't see in yourself," demonstrating commitment to their growth.
• Managing interview panels: Meet with interview panelists beforehand, share candidate information, and coordinate to ensure a positive experience that also helps sell the candidate.
• Bold compensation for top talent: Compensate exceptional talent boldly. Most HR and compensation guidelines tend to regress to the mean, overvaluing low performers and undervaluing high performers.

7. Board and Investor Management

Chesky addresses how to handle board members or VCs giving bad advice.

7.1. The Importance of Choosing Board Members

• Prefer investors with operational experience: "Just because you watched a Golden State Warriors game courtside doesn't mean you can coach an NBA team." VCs watching many companies doesn't mean they know how to run one. He prefers raising from investors who have started and run companies or have operational experience as COOs or executives.
• Beware of junior partners: Junior partners tend to be risk-averse and unlikely to support you through tough times.
• Board members' impact: Board members can't make a company, but they can destroy one. Choose them very carefully.

7.2. Handling Bad Advice

• Seek help from competent board members: Explain the situation to capable board members and ask them to help persuade the one giving bad advice.
• Persuade with details: Rather than arguing, "explain the details of the problem thoroughly" so they realize on their own that their judgment is wrong.
• Responsibility for outcomes: Remember that even if you follow a VC's advice and fail, the CEO bears all responsibility. "All that matters is whether you succeed."

Conclusion

Brian Chesky's 'Founder Mode' goes beyond simply returning to a founder's early spirit. It offers deep insights into overcoming the bureaucracy and inefficiency that inevitably arise as companies grow, maintaining CEO control over the core asset—product—and attracting and retaining top talent. His experience serves as practical guidance, especially for leaders of high-growth companies.