Dalton Caldwell - Startup Investor School Day 2 | Summary and Q&A

March 6, 2018
Y Combinator
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Dalton Caldwell - Startup Investor School Day 2


This video provides insights on investor decision-making processes, including asking the right questions, evaluating founder meetings, and dealing with various scenarios, such as flatlining investments.

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Key Insights

  • 👀Key Insight 1: It's important for investors to have a well-defined process for making investment decisions, including having a clear criteria for evaluating startups and setting a budget.
  • 🔒Key Insight 2: Face-to-face meetings are crucial in the investment process, where investors make the decision to invest or not. Scheduling meetings in a non-painful way and being punctual will put investors ahead of the pack.
  • 🚀Key Insight 3: Investor process can be visualized as a funnel, starting with leads and ending with investments. It's important to qualify leads and make decisions based on predetermined criteria to optimize investment decisions.
  • 💭Key Insight 4: Having personal conviction is crucial for making investment decisions. Investors should not be influenced by groupthink and should be willing to make investments that may seem unconventional to others.
  • 📝Key Insight 5: Communication is key in the investment process. Investors should be clear and transparent in their decision-making, whether it's saying yes or no to a startup. Ghosting founders or flip-flopping between yes and no is not recommended. ⏰Key Insight 6: Timeframe and commitment are important considerations for investors. Investors should have a clear idea of how much time and money they are willing to commit, and founders should be aware of these criteria.
  • 🌍Key Insight 7: Investors should focus on asking founders basic questions during meetings to understand their business and vision. Understanding the fundamentals and building rapport with founders should be the priority in early meetings.
  • 💡Key Insight 8: Investors should trust their gut instincts and have personal conviction when making investment decisions. They should also be willing to look stupid and be wrong at times, as this is part of the process of finding successful investments.


Hey good morning thank you we have a lot to do today so I'd like to get my way my part out of the way as quickly as possible good morning again and welcome to our second day of start-up investor school my role is a little bit more but not much more than telling everyone not to park over there so don't park over there there's other parking apparentl... Read More

Questions & Answers

Q: How should investors approach discussing competition with founders?

When discussing competition, it's important for investors to approach the topic with neutrality and ask open-ended questions. By listening to how founders talk about their competition and their strategies to win, investors can gain insights into the company's potential advantages and differentiators, as well as gauge the founder's knowledge and confidence in the market.

Q: What should investors do if they have proprietary information about a company that the founders are unaware of?

It is generally best to keep proprietary information to oneself, as sharing it with founders may lead to unintended consequences and potential breaches of trust. However, investors can use the information to inform their investment decisions and assess the potential risks and opportunities associated with the company.

Q: How should investors handle investments that are not performing well and flatlining?

When investments are not performing well and appear to be flatlining, there may not be much that investors can do. It is important to assess the longer-term potential of the company and determine whether it is worth holding onto the investment with the understanding that it may take a significant amount of time to see any returns. In such cases, investors should closely monitor the company's progress and make informed decisions based on their long-term investment goals.

Q: How should investors navigate situations where they want to invest but are uncertain if the company will be able to raise additional funding?

If an investor wants to invest but is unsure if the company will be able to raise additional funding, the best approach is to be transparent with the founder about their concerns. The investor can express their interest in investing but highlight the potential financial risks. It is important to set clear expectations and discuss alternative investment strategies or milestones that would make the investor more comfortable committing funds.


In this video, Dalton Caldwell, founder and partner at YC (Y Combinator), talks about the process of making smart investment decisions as an angel investor. He emphasizes the importance of having a well-defined process and criteria, conducting face-to-face meetings, and developing personal conviction in the investments made.

Questions & Answers

Q: Why is having a process important in making investment decisions?

Having a process in place helps investors make more informed decisions and ensures they do not fall into the trap of wishy-washy or indecisive thinking. It helps them stay focused and evaluate potential investments based on predefined criteria.

Q: What is the role of face-to-face meetings in the decision-making process?

Face-to-face meetings are crucial as they allow investors to gauge the founder's credibility, trustworthiness, and passion for their business. It also gives investors an opportunity to ask questions, gain a deeper understanding of the company, and assess the founder's ability to articulate their vision.

Q: How should investors determine their investment criteria?

Investors should establish their own investment criteria based on their personal preferences, expertise, and specific goals. These criteria can include factors like the team, market size, traction, relevant expertise, and investment terms. Having different criteria from other investors helps in finding unique and potentially high-return investments.

Q: Why is personal conviction important in making investment decisions?

Personal conviction is crucial because it helps investors stay committed to their decisions and weather the ups and downs that come with investing in startups. It also allows investors to confidently make investments even if they may seem unconventional or unappealing to others. Without personal conviction, investors may struggle to make optimal investment decisions.

Q: What are some pitfalls to avoid in the decision-making process?

Some common pitfalls include taking too long to make a decision, flip-flopping between yes and no, making oneself the center of attention in meetings, and giving unsolicited advice. It's important to be decisive, communicative, and respectful in the decision-making process.

Q: How should investors communicate their decisions to founders?

Investors should directly and clearly communicate their decisions to founders, whether it is a yes or no. It's important to not ghost founders or give false hope. If possible, providing reasons for the decision can be helpful but is not always necessary.

Q: What should investors look for in meetings with founders?

Investors should focus on understanding the basic aspects of the business, such as what the company does, who is on the team, and the progress made. They should also assess their personal trust in the founders, evaluate the potential for success, and consider if they can envision working with the founders in the long run.

Q: What are some red flags or warning signs in meetings?

Red flags may include minimal engagement or distraction from the investor, making the meeting about oneself instead of the founder, excessive advice without investment commitment, and excessive follow-up meetings without a clear decision. Trusting one's gut feeling about the founders and their credibility is also an important consideration.

Q: How can investors say no or yes effectively?

Saying no promptly and directly, with proper reasoning if possible, is crucial to avoid wasting the time of founders. Saying yes requires clear communication of enthusiasm and commitment, followed by timely execution of the investment. Introducing unnecessary complications or overstepping boundaries when saying yes should be avoided.

Q: What is the final takeaway from the video?

Developing a well-defined process, conducting face-to-face meetings, and having personal conviction are key to making smart investment decisions as an angel investor. It's important to stay focused, communicate decisions effectively, and establish meaningful relationships with founders. Investing in contrarian ideas and being willing to take risks can lead to unique and high-return opportunities.


Investors should establish a well-defined investment process and criteria, conduct face-to-face meetings with founders, and develop personal conviction in their investment decisions. A strong process helps in making informed decisions and avoiding indecisiveness. Face-to-face meetings allow investors to assess founders' credibility and passion, while personal conviction drives confidence and commitment in investments. Pitfalls to avoid include indecisiveness, self-centeredness, and excessive advice-giving. Clear and timely communication of decisions is essential, and investors should focus on trust, basic understanding of the business, and long-term compatibility with founders. In conclusion, having a defined process, conducting meaningful meetings, and being confident in investment decisions are key to success as an angel investor

Summary & Key Takeaways

  • The importance of having a clearly defined investment process and funnel.

  • Tips on conducting effective founder meetings, including asking basic questions, assessing trustworthiness, and gauging personal conviction.

  • How to handle various investment scenarios, such as losing faith in a company, milestone-based financings, and dealing with flatlining investments.

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