Ep 36: Convertible Notes - Real Stories from the Trenches
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About this listen
In this in-depth episode, we demystify convertible notes—a widely used, yet often misunderstood financing tool for early-stage startup founders. You'll learn how convertible notes work, what makes them attractive, and why they can also carry hidden risks that impact long-term founder equity and company control.
💡 Key Topics Covered:
- Why convertible notes emerged as a solution to the early-stage funding dilemma
- The core mechanics: interest rates, maturity dates, valuation caps, and discounts
- How dilution works—and how founders can unknowingly give up more equity than expected
- Legal risks of debt instruments and what happens if you don’t hit a conversion milestone
- The tension between speed and flexibility vs. long-term complexity and legal costs
- Strategic tips for modeling your cap table and negotiating favorable terms
- Pitfalls from the trenches: real-world founder stories of dilution, investor leverage, and “silent screwing”
- Comparison with SAFEs, KISS notes, and priced equity rounds: which is right for you?
📌 Key Takeaways:
- Convertible notes are debt, not equity—and that distinction matters more than most founders realize.
- Valuation caps, discounts, and accrued interest can lead to significant and unexpected dilution.
- Multiple notes with varying terms = messy cap tables, complex conversions, and investor headaches.
- Founders must model dilution scenarios and negotiate longer maturity terms to protect equity.
- Choose your investors wisely—terms are important, but relationships are critical.
👉 If you're raising capital and need expert guidance, visit startupwarriors.io/podcast to learn more and book a session.
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