A founder sent me a term sheet with a 2x participating preferred and asked if it was 'standard.' I sent back a one-page spreadsheet showing what it does at a $20M exit. They understood in thirty seconds. Numbers explain terms better than lawyers do.
Caleb Nakamura
Associate, Corporate, Hale & Mercer LLP · Start-ups, seed rounds, plain-English term sheets
Chicago · Hale & Mercer LLP · 911+ connections
About
I am a corporate associate at Hale & Mercer working with founders: formation, seed and Series A financings, option plans, and the contracts that come before any of that. If I cannot explain a clause in one sentence, it probably should not be in your contract.
I grew up on an almond orchard outside Sacramento and spent summers driving a forklift in the packing shed, learning to negotiate by watching my father deal with the co-op. Economics at Davis, law at Chicago, and a strong preference for documents a founder can actually read.
Off duty: the Pacific Crest Trail in sections, a 1978 Pentax K1000, and a reliable mid-range jumper on Tuesdays.
Activity
Closed a seed round today for two founders who built their company from a kitchen table in Pilsen. Investors' first draft gave them control at the next round. The final draft doesn't. I explained every clause; they chose every one. That's the job.
Plain-English drafting is not dumbing down. It is the discipline of knowing what a clause does well enough to say it simply. If I can't, I don't understand it yet, and neither will a judge.
Experience
Founder-side financings, formation, option plans, commercial contracts. First solo matter: a 2024 West Loop logistics seed round.
Rewrote a shareholder agreement into plain English as a training exercise. Priya kept it.
Almonds. Learned what a co-op contract does to a family's year.
Education
University of Chicago Law School, J.D., 2022
University of California, Davis, B.A. Economics, 2016
The spreadsheet is the memo. Always send the spreadsheet.
And check who owns the code before you worry about the preference.