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Advice from investor who backed 40 Unicorns l Elad Gil

Meet Elad Gil, an investor or advisor to prominent companies such as Airbnb, Airtable, Coinbase, Deel, Figma, Gusto, Notion, Pinterest, Stripe, and more.

Elad Gilguest
Mar 27, 202429mWatch on YouTube

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CHAPTERS

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Chapter summaries

  1. Elad Gil's Background as Operator and Investor

    Elad Gil recounts his career: running a telecom equipment company through layoffs, joining Google, selling a startup to Twitter, and scaling Twitter. He also lists his investments in roughly 40 billion-dollar companies and early generative AI bets.

    • •Ran a company that shrank from 150 to 13 people in five rounds of layoffs
    • •Joined Google, then started a data infrastructure company that Twitter bought in 2009
    • •Helped scale Twitter from about 90 to 1,500 people
    • •Backed about 40 companies worth $1B+, including Stripe, Airbnb and Figma
    • •Early investor in generative AI companies such as Perplexity and Harvey
  2. Why He Moved to Silicon Valley and Google's Hypergrowth

    Gil explains his move from academic biology and math to Silicon Valley, motivated by long-term impact on humanity. He describes the chaos of Google growing from 1,500 to 15,000 people, including constant reorgs and a gray market for talent.

    • •Left academia because one person in biology couldn't have that big an impact
    • •Techno-optimist who wants to do useful things through technology
    • •Google doubled roughly every six to 12 months, forcing frequent reorgs
    • •Managers with 50-100 reports created a gray market for talent, which helped him start mobile efforts
  3. Lessons from Google: Networks, Ambition, and Hypergrowth

    Gil shares three takeaways from Google: small groups of early employees go on to do great things together, Google's leaders pushed for big ambition, and employees at hypergrowth companies shouldn't worry excessively about themselves. He cites the PayPal and Google networks as examples.

    • •PayPal and early Google alumni networks seeded many companies and operators
    • •Larry Page, Sergey Brin and Eric Schmidt pushed people to think bigger, such as a $10B market instead of $100M
    • •Leaders pushed hard on what makes a product special or different
    • •In hypergrowth companies, opportunity is plentiful so don't over-worry about your career
  4. Starting a Company in the Pre-YC Era and Building for the Future

    Gil describes how hard it was to start a company before Y Combinator, then covers his first company, a location data product that became an early API-first business. He reflects on mistakes, like building for the past and having a team without diversity, and introduces the 'why now' idea.

    • •Little information, money, or angel funding existed when he wanted to start a company
    • •His company moved from a location website to an API, an early developer-first product
    • •An all-ex-Google team built huge infrastructure before it had users
    • •Build a year or two ahead rather than for the era of your previous employer
    • •Why now examples: Uber (free GPS lookups with iPhone), Samsara (regulation), Anduril (drones and machine vision)
  5. Selling to Twitter

    Gil explains how a vendor discussion with Twitter turned into an acquisition offer. He lays out the reasons the team decided to accept.

    • •A Twitter team member invited them to brainstorm a product without outside constraints
    • •Twitter grew from about 50 to 90 people in the three months before the deal
    • •Reasons to sell: a massive developer ecosystem, a great place for engineers, and a good financial outcome
    • •Excitement about joining a company that was clearly breaking out
  6. Missionary vs. Mercenary and Why the Best Investments Look Expensive

    Gil describes John Doerr's mercenary-or-missionary framework and Naval Ravikant's career-stage version. He notes that many famous founders were once willing to sell, and that the best investments, like Stripe and Facebook, always look too expensive at the time.

    • •Naval's view: mercenary early, missionary mid-career, artist late in career
    • •Google and Facebook both nearly sold early
    • •Facebook's rounds were each called stupid before proving brilliant
    • •Yuri Milner had inside knowledge from running a social network in Russia
    • •The same logic applied to bad companies leads to bad investments
  7. How the CEO Role Evolves

    Gil compares an early-stage startup, which he likens to a simple egg, with a late-stage company, which he likens to a complex full-grown chicken. He lists what stays constant for CEOs: setting direction, allocating resources, acting as chief psychologist, and managing their own energy.

    • •Early stage is about customers, building what they want, hiring, and not running out of money
    • •Later stage adds internationalization, multiple products, new executive roles, M&A and financing
    • •CEOs always set direction and allocate resources
    • •The CEO acts as chief psychologist early on
    • •Managing your own energy matters because the job is stressful
  8. Conventional Wisdom That's Wrong: Co-Founders, Ideas, and Learning

    Gil challenges common startup beliefs: that you need a co-founder, a good idea, or prior learning. He favors learning by doing, and gives advice on co-founder dynamics if you choose to have one.

    • •Many of the biggest companies had a single founder or unequal partnerships
    • •Some big companies started accidentally, with founders trying different things
    • •Learning by doing beats learning in advance
    • •Complementary skills and clear decision-making reduce co-founder conflict
    • •Greatest companies are usually one person's vision, with at least one person who can sell
  9. Bootstrapping vs. Raising Capital, and the COO Role

    Gil argues founders should think about what the company needs rather than just raising money, citing many bootstrapped or capital-efficient successes. He says Silicon Valley bootstraps too little while elsewhere companies raise too little, and then discusses the loosely defined COO role.

    • •Microsoft, Dell, Yahoo, eBay, Instagram and Midjourney were bootstrapped or capital-efficient
    • •Raise money if it helps you win a market faster, as Rippling did
    • •Bootstrapping fits businesses that can charge early and at high leverage
    • •Silicon Valley bootstraps too little, other places raise too little
    • •COO has no clear definition and means whatever the founder doesn't want to do
  10. What Boards Do at Early and Late Stages

    Gil explains that very early companies don't need a board, and that a board's most important early job is deciding who the CEO is. Over time boards shift toward compliance, committees, and independent directors.

    • •Boards are superfluous at three or four people
    • •The board's most important role early is deciding who is CEO
    • •The CEO and founding team are ultimately on the line for execution
    • •Later boards focus on compliance, compensation and audit committees
    • •Board composition shifts from one investor to many independents
  11. How Founders Should Use Their Boards

    Gil says many founders wrongly treat the board as their boss. He describes using boards for hiring, customers, talent assessment and strategy, discusses how much leverage boards have to fire founders, and advises vetting board members through back-channel references.

    • •Use board members to close candidates, back-channel customers and assess talent
    • •Founders now often control more board seats than they did 10 years ago
    • •Several prominent founder exits, such as Uber and WeWork, came despite board control
    • •Principal-agent misalignment can affect investors, executives and board members
    • •Back-channel previous colleagues to ask how a board member acted when things went badly
  12. 26:23 – 29:08Read this chapter

    Why Silicon Valley Is the Best Place to Build Tech

    Using Moore's Law as an example of a self-fulfilling prophecy, Gil explains why Silicon Valley works: it attracts ambitious people, has a pay-it-forward culture, holds deep know-how, and has critical mass. He concludes that it remains the most important tech hub by far.

    • •Moore's Law was an extrapolation that became self-reinforcing
    • •Silicon Valley attracts extremely ambitious technologists from everywhere
    • •Pay-it-forward and cohort effects help early founders
    • •Local know-how and critical mass let you ride the curve early
  13. Technology as a Force for Human Progress

    Gil closes by describing technology as a broadly positive force that has lifted billions out of poverty. He says technology includes agriculture, transportation, electricity and vaccines, and that he wants to contribute to the most important technologies and companies.

    • •Technology has helped lift hundreds of millions or billions out of poverty
    • •Technology includes agriculture, transport, electricity and healthcare, not just software
    • •High tech once meant automotive and electrification
    • •He wants to work with the most important technology companies over time

Publisher timestamps

  1. 0:00Intro
  2. 1:19Key Lessons from 20 Years in Silicon Valley
  3. 11:49Be Missionary and MercenaryRead this chapter
  4. 15:24advice on scaling companiesRead this chapter
  5. 21:56How founders should use their boards to grow their companyRead this chapter

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