Uploaded August 2026 | Updated September 2026, 2 weeks ago
Sherwood Callaway, founder and CEO of Sazabi, breaks down the angel investor strategy that put over 100 founders, CTOs, and technical leaders from companies like Browserbase, Replit, and Vercel on his cap table, and why he sold the vision before he had a team or product to show for it. He also walks through how Sazabi lowers the barrier to adoption for skeptical developers, and lays out his own premortem: the specific scenarios, from model improvement stalling to a venture winter, that could keep Sazabi from succeeding.
Lindsay Pettingill sits down with Sherwood to get into his advice for founders building an angel network, the most annoying part of selling to developers, what actually creates a "sticking point" for Sazabi's customers, and two very different futures where observability as a category could become obsolete altogether.
00:00 The angel investor strategy behind Sazabi's cap table
02:36 Advice for founders building their own angel network
04:05 The most annoying thing about selling to developers
05:22 Lowering the barrier to adoption for skeptical developers
08:03 What creates the "aha moment" for new customers
09:19 Sherwood's premortem: what could kill Sazabi
15:35 Why he feels good about the odds
This is an excerpt from our full conversation with Sherwood Callaway. Watch the full episode here: youtu.be/LikGg0uYNe4
Sherwood Callaway, founder and CEO of Sazabi, breaks down the angel investor strategy that put over 100 founders, CTOs, and technical leaders from companies like Browserbase, Replit, and Vercel on his cap table, and why he sold the vision before he had a team or product to show for it. He also walks through how Sazabi lowers the barrier to adoption for skeptical developers, and lays out his own premortem: the specific scenarios, from model improvement stalling to a venture winter, that could keep Sazabi from succeeding.
Lindsay Pettingill sits down with Sherwood to get into his advice for founders building an angel network, the most annoying part of selling to developers, what actually creates a "sticking point" for Sazabi's customers, and two very different futures where observability as a category could become obsolete altogether.
00:00 The angel investor strategy behind Sazabi's cap table
02:36 Advice for founders building their own angel network
04:05 The most annoying thing about selling to developers
05:22 Lowering the barrier to adoption for skeptical developers
08:03 What creates the "aha moment" for new customers
09:19 Sherwood's premortem: what could kill Sazabi
15:35 Why he feels good about the odds
This is an excerpt from our full conversation with Sherwood Callaway. Watch the full episode here: youtu.be/LikGg0uYNe4
