CARIBEquity Investor Toolkit Online

Post-Investment Review & Case Study Tool

Dual-purpose framework for (1) internal investment reviews to capture lessons learned and (2) external case study documentation for teaching and knowledge sharing. Conduct reviews at key milestones: first year anniversary, major pivot, exit, or failure.

  1. Purpose: This tool serves two purposes: (1) Internal learning - complete Parts 1-3 for systematic investment reviews at key milestones; (2) External case studies - complete Part 4 to create teaching materials for the CARIBEquity community
  2. Be Honest: Be honest and specific in your responses. The goal is learning, not blame
  3. Team Collaboration: Conduct reviews with all team members who participated in the original investment decision
  4. Document Progress: Fill in investment overview, thesis review, performance analysis, and lessons learned sections
  5. Save Your Work: Use the Save Review button to store your progress locally, or Export JSON for backup

Investment Overview

Part 1: Investment Thesis Review

Original Investment Thesis
Summarize in 2-3 sentences what you believed when you made this investment.
Key Assumptions
List the 5-7 key assumptions underlying your investment decision.
Assumption Validation
For each assumption, assess whether it proved correct and its impact on the outcome.
Assumption Correct? Evidence Impact on Outcome
Due Diligence Assessment
What signals did you miss during due diligence?
Red Flags
Were there red flags you ignored or rationalized away?

Part 2: Performance Review

Financial Performance vs. Projections
How did actual financial performance compare to original projections?
Product/Market Fit Evolution
Did the company achieve product-market fit? How did it evolve?
Team Performance
How did the founding team perform? Key hires? Departures?
Execution Against Milestones
What milestones were hit? Missed? Why?

Part 3: Lessons Learned

What Worked Well
What aspects of this investment exceeded expectations?
What Didn't Work
What aspects underperformed or failed?
Surprises (Positive and Negative)
What unexpected developments occurred?
Would You Invest Again?
Knowing what you know now, would you make this investment again?
Key Takeaways for Future Investments
What specific lessons will you apply to future investment decisions?
Process Improvements
What changes will you make to your investment process based on this experience?

Part 4: Case Study Narrative (Optional - for External Sharing)

Complete this section if you plan to share this investment as a teaching case study. Focus on storytelling and key lessons that others can learn from.

Executive Summary
2-3 sentence overview of the investment story and outcome (suitable for external audiences)
The Opportunity
Describe the market opportunity and why it was compelling
Investment Decision Rationale
Why did you decide to invest? What were the key factors?
Key Milestones
Key Milestones & Turning Points
Turning Points
Tell the story of what happened after investment (chronologically)
Outcome
Outcome & Impact
Impact
What was the final outcome? Financial returns, social impact, lessons learned
Key Lessons for Other Investors
What should other early-stage investors learn from this case?
Caribbean Context
Caribbean Context & Relevance
Relevance
What makes this case particularly relevant for Caribbean investors?