Episode Summary:
Understanding how to invest in startups requires more than just writing a cheque. Cheryl and Maxine break down the legal structures behind startup investing, covering SAFE notes, convertible notes, and priced rounds. Whether you're a seasoned investor or just starting out, this episode unpacks the key terms, investor-friendly vs. founder-friendly clauses, and the risks involved. They discuss the evolution of SAFEs, why they've become the dominant structure in early-stage funding, and the critical differences between pre-money and post-money SAFEs. Plus, they explore the role of pro-rata rights, most favoured nation (MFN) clauses, and side letters—so you don’t get caught off guard in your next deal. If you’ve ever wondered how to protect your equity position, when to push back on certain terms, or what legal documents you’ll actually be signing, this episode is your investor cheat sheet.
Episode Sponsors:
Chapters:
00:00 – Why startup investment structures matter
01:45 – SAFE notes, convertible notes, and priced rounds explained
03:47 – How founders raise money: equity vs. debt
06:21 – The documents you’ll sign in a priced round
10:22 – Do startups need a constitution? Red flags to watch for
14:29 – Side letters: What are they, and should you be worried?
19:08 – Pro-rata rights & why they matter for investors
22:23 – Most Favored Nation (MFN) clauses explained
30:27 – Pre-money vs. post-money SAFEs: Which one is better?
38:03 – Why valuation caps and discounts can be a double-edged sword
43:53 – Investor-friendly vs. founder-friendly terms: What’s fair?