Template Library for Seed Rounds – Various “open source” and well-vetted templates, in addition to content, for being lean on seed rounds without giving up flexibility and structure optimization.

How Much Seed Rounds Cost – There are smart and effective ways to contain costs on legal fees and other expenses for your seed round, but there are also myopic ways to be penny wise and pound foolish. The smartest teams know the difference.

Trust, Friendliness, and Zero-Sum Startup Games – Approach all negotiations from the perspective that, while the best investors are very “friendly,” they are still significantly misaligned economically from the interests of the common stock (founders and employees). Don’t drink any kool-aid suggesting you should let your guard down and just accept whatever advisors/templates they offer on the table.

Negotiation is Relationship Building – The (polite) back and forth of negotiating high-stakes issues is one of the most important ways to get to know who your lead investors really are, and set expectations for the long-term dynamics of the relationship.

Posts on Seed Round Structure – Convertible notes, SAFEs, and Seed Equity are the main options, but there are key nuances, and pros/cons, to each.

• Pre-Seed Funding with Post-Money SAFEs: Revisited in 2024  – The YC “standard” Post-Money SAFE is designed with very investor-biased economics, which is a far departure from the original pre-money SAFE. Lots of companies are using SAFEs, but the smart ones won’t stick to YC’s default harsh economics.
• A Fixed Post-Money SAFE Structure, and a Math Model  – A simple redline fixing the worst economic costs of the post-money SAFE, and a math model showing the implications.
• Milestone-Based Valuation Caps – When there’s disagreement as to what the appropriate valuation cap is for a seed round, offering a tiered structure based on various milestones can often bridge the gap.
• Myths and Lies about Seed Equity Rounds  – Yes, convertible notes and SAFEs are very popular for seed rounds, but they’re not the only way to do raise seed money, and in some contexts lean equity makes a lot more sense.

Relationships and Power in Startup Ecosystems – Structuring investment for a startup is a very high-stakes, complex process in which the investors you’re dealing with will usually have 50x the experience that you do. Working with seasoned, independent advisors can be your most powerful “equalizer” in those discussions, but only if you aren’t duped into using advisors who are ultimately controlled by the money, or who behave as if one approach fits all.

Pre-Series A Startup Boards – It’s important to understand how consequential giving a Board seat is, and why most companies don’t give them to seed investors; though there are contexts in which it makes sense.

Podcast on Startup Fundraising – A short podcast for the American Bar Association on which I was a guest speaker, in which I walked through the various fundraising stages of early-stage startups (starting with Friends and Family) and issues founders should watch out for.