Okay, here’s a breakdown of the text, categorized for clarity and highlighting key takeaways:
**I. Core Argument & Shift in Approach:**
* **The Problem:** The author has experienced significant losses and diluted ownership in their angel investments over 15 years. The macro environment (post-2023) created headwinds, and the opportunity cost of capital was too high. They felt like later investors were benefiting at the expense of early supporters.
* **The Shift:** They’ve moved away from a broad, diversified angel investing approach to a more focused strategy prioritizing deeper founder relationships and learning.
**II. Reasons for the Change:**
* **Macroeconomic Factors:** The post-2023 economic climate (high interest rates, inflation) made startup investing riskier.
* **Opportunity Cost:** The time horizon for returns was too long, and the risk of significant losses was too high.
* **Dilution:** They experienced repeated dilution of their ownership stakes.
**III. What They’re Doing Now:**
* **Board Roles:**
* **Collective Health:** Serving on the board of a growth-stage company (originally invested in by Rock Health).
* **Cofortility:** Board Chair of a new company.
* **Learning & Teaching:**
* **Podcast:** Hosting a podcast focused on healthcare innovation.
* **Courses:** Teaching two courses a year at Columbia Business School and Harvard Medical School.
* **LP in VC Funds:** Investing as a Limited Partner (LP) in a handful of VC funds (3 years in).
**IV. Data & Portfolio Performance (To be shared next week):**
* **54 Startup Investments:** Over 15 years.
* **Returns, Losses, and Current Portfolio Status:** This is a key piece of information to be revealed next week.
**V. Recent News & Updates (as of the writing):**
* **Cofortility Raises Series A:** A woman-led women’s health company (breaking funding barriers) has raised a Series A round. This is being celebrated as a significant achievement.
* **Podcast Episode:** A recent podcast episode focused on Oscar Health, highlighting their success in a notoriously difficult industry. Key topics covered include:
* Outsider approach to healthcare
* High NPS scores
* Balancing care denial with empathy
* Disruptive impact of ICHRAs
* Changing employer healthcare market
**VI. Key Themes & Takeaways:**
* **Risk Management:** The author emphasizes the importance of carefully assessing risk and understanding opportunity costs.
* **Strategic Focus:** Moving from breadth to depth is presented as a more effective strategy.
* **Supporting Underrepresented Founders:** Celebrating the success of Cofertility reflects a commitment to supporting women-led companies.
* **Continuous Learning:** The author’s approach is driven by a desire to learn and adapt.
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Do you want me to:
* Summarize a specific section in more detail?
* Analyze a particular aspect of the author’s strategy?
* Generate questions based on the text?