Startup Experts Share Their Investor Horror Stories

Y Combinator

Y Combinator

26 min, 9 sec

A comprehensive discussion on handling challenging investor meetings, sharing personal stories, and offering advice to founders.

Summary

  • Founders share their worst investor meeting experiences, emphasizing that such meetings can be demoralizing.
  • Investor meetings are a two-way street, and mutual respect and professionalism are essential.
  • Investor feedback should not be the sole barometer for a startup's potential, and founders should not pivot their product based solely on investor input.
  • Proper preparation, including understanding investor preferences and maintaining the startup's core vision, is crucial.
  • Founders should be wary of investors who may hurt the company and should seek those who respect their time and decisions.

Chapter 1

Introduction to Investor Meeting Challenges

0:00 - 25 sec

An introduction to the challenges founders face in investor meetings, and the importance of being prepared for the worst.

An introduction to the challenges founders face in investor meetings, and the importance of being prepared for the worst.

  • Raising money involves figuring out how to handle meetings that can go wrong.
  • Bad investor meetings can lead founders to question their company's existence.
  • Being prepared for the worst can make you better off when it's your turn.

Chapter 2

A London Meeting with Bad Etiquette

0:37 - 1 min, 31 sec

A recount of an investor meeting in London characterized by poor etiquette and power plays.

A recount of an investor meeting in London characterized by poor etiquette and power plays.

  • The investor kept the founder waiting, ate lunch with his hands while picking his feet, and smoked in a closed office.
  • This behavior was seen as a bizarre power play and did not result in investment.

Chapter 3

Investor Status Games

2:22 - 30 sec

Discussion on the status games played by investors and the shift toward founder-focused VCs.

Discussion on the status games played by investors and the shift toward founder-focused VCs.

  • The financial world is full of status games, but a shift is happening toward valuing product and creation.
  • Future successful founders will have their pick of builder-focused VCs.

Chapter 4

Sand Hill Road Experience

2:59 - 2 min, 16 sec

An account of a meeting with a famous VC firm that went awry due to inappropriate behavior and lack of focus on the business.

An account of a meeting with a famous VC firm that went awry due to inappropriate behavior and lack of focus on the business.

  • A VC's attempt to bond over language knowledge during an important pitch meeting felt inappropriate and a waste of time.
  • This example highlights the importance of understanding an investor's process as their product.

Chapter 5

The Cash Crunch Email

7:52 - 1 min, 44 sec

A story of how a poorly planned attempt to seek more funding from seed investors backfired.

A story of how a poorly planned attempt to seek more funding from seed investors backfired.

  • Sending an email with the title 'Cash Crunch' and hoping for more funding from seed investors.
  • The investor meeting resulted in no interest in investing due to a lack of a solid pitch and organization.

Chapter 6

Investor Database and Demo Day

12:17 - 1 min, 51 sec

Advice on utilizing YC resources like the investor database to avoid bad investors and prepare for funding rounds.

Advice on utilizing YC resources like the investor database to avoid bad investors and prepare for funding rounds.

  • Use the YC investor database for feedback on investors and to prioritize meetings.
  • Demo day gives founders control and agency in fundraising, with investors coming to them.

Chapter 7

Investor Meeting Mind Games

14:27 - 1 min, 50 sec

Anecdotes about investors playing mind games to test founders during pitches.

Anecdotes about investors playing mind games to test founders during pitches.

  • An investor deliberately distracted a founder by noisily opening candy to see how they would react.
  • Such tactics are used by investors to test founders, but may not be a good fit for a working relationship.

Chapter 8

The Importance of Knowing Who's CEO

16:19 - 1 min, 44 sec

A recount of a failed investor meeting due to the founders' inability to decide who the CEO was.

A recount of a failed investor meeting due to the founders' inability to decide who the CEO was.

  • Failing to answer who the CEO was in a final partner meeting with a top VC firm led to an immediate rejection.
  • This highlights the necessity for founders to have clear roles and answers to critical questions.

Chapter 9

Maintaining Professional Boundaries

18:54 - 1 min, 33 sec

A story about an investor crossing personal boundaries by asking if co-founders were dating.

A story about an investor crossing personal boundaries by asking if co-founders were dating.

  • The investor's question about the founders' personal relationship was seen as unprofessional and inappropriate.
  • Good investors challenge founders respectfully and allow them to make the final calls.

Chapter 10

Investor Attraction vs. Startup Success

20:30 - 2 min, 12 sec

Encouragement to stay focused on building a business, not just on investor attraction, and advice on avoiding negative investor influence.

Encouragement to stay focused on building a business, not just on investor attraction, and advice on avoiding negative investor influence.

  • Founders should not rely solely on investor traction or feedback to measure success.
  • Avoiding investors who can harm the company is more important than finding great ones.

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