Syndication and deal sizing dynamics

CJ sits down with Marshall Hawks, a 20-year veteran of venture lending and author of Venture Debt Deals. They cover the real rules of thumb behind deal sizing, why lenders underwrite likelihood of raising again (not breakout outcomes), how banks and private credit differ, the three real sources of repayment, and how to actually run a venture debt process without blowing your legal budget.

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LINKS:

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Marshall: https://www.linkedin.com/in/marshallhawks/

Marshall's website: https://www.marshallhawks.com

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

TIMESTAMPS:

0:00 Preview and intro

3:23 Marshall's background and the book

4:47 Venture Deals as inspiration

6:30 Companies Marshall has worked with

6:49 The venture debt sweet spot

8:01 Why venture debt follows equity raises

10:55 The 25–40% rule of thumb

12:08 AI companies and the limits of the rule

13:58 Sponsors — Abacum | Brex | Metronome

17:15 How lenders think vs. investors

19:12 The three sources of repayment

21:37 Venture debt and the AI boom

23:52 Banks vs. private credit

26:28 Sponsors — RightRev | Rillet | Tabs

29:57 Private credit pricing and warrants

33:04 Syndicated deals

35:04 Legal timelines

38:13 Who pays the legal bill?

40:06 Why your GC shouldn't quarterback the deal

41:30 What forecast to give your lender

43:37 Reporting cadence

45:57 Bad news should travel fast

47:49 The Twitch case study

50:19 Are we over our skis in 2026?

54:50 Where to get Venture Debt Deals

55:09 Credits