How Developer Tools Win Enterprise Without Losing Their Soul | How To Nail Pricing As A PLG Company | Why Building for Free Users First Nearly Cost Us the Market with Feross Aboukhadijeh, CEO & Co-founder of Socket

Every bottom-up PLG company faces this tension:

PLG gets you in. Enterprise funds the future. They need vastly different products - how do you prioritize?

If you try to please both motions at once, you starve both.

How to balance PLG with enterprise is what I discuss with Feross Aboukhadijeh, the CEO and co-founder of Socket ($65M raised from a16z, Abstract, Dylan Field, Aaron Levie, and other).

Socket, a developer-first security platform protecting code from vulnerable and malicious dependencies. Before Socket, Feross was an open source maintainer and developer who built widely-used libraries.

In Today's Episode We Discuss:

01:43 - How developer background dictated Socket's PLG-first strategy over enterprise

04:50 - Building a GitHub app in 48 hours to avoid launching with zero user capture

07:56 - The counterintuitive rule: launch with intentionally missing enterprise features

10:53 - Why Socket deliberately ignored vulnerabilities despite every competitor offering it

11:20 - The dirty secret of startup pricing pages most founders won't admit

15:37 - How Socket mistakenly modeled pricing after GitHub's public/private repository strategy

16:08 - Why cryptocurrency companies exposed a fatal flaw in Socket's pricing model

18:19 - Going straight to enterprise sales to defend against fast-following competitors

19:37 - Why product quality loses to inferior products with superior go-to-market

21:36 - Socket's first enterprise deal was $500 and they kept doubling until pushback

24:27 - When PLG and enterprise roadmaps become zero-sum resource battles

26:27 - The strategic mistake of abandoning PLG motion after enterprise traction

28:54 - How developer awareness creates unfair advantages in security tool evaluations

29:23 - Enterprise handholding versus self-serve product design create opposing company muscles

33:01 - Figma's playbook: how connecting free-to-enterprise destroys customer acquisition costs

36:12 - The biggest regret: not building the PLG funnel before enterprise distraction hit

40:57 - Getting SOC 2 on day one would have parallelized six months of enterprise delays

41:00 - The monstrosity trap: second-time founders who hire VPs before product-market fit

40:13 - Why the popular advice to limit cap table size is fundamentally wrong

41:05 - Why Feross regrets turning away a $10K angel investment over ego

43:24 - The technical founder's fatal mistake: choosing to code over customer conversations

45:04 - Why selling before building feels wrong but saves months of wasted development

45:13 - The Mom Test: the book that teaches founders how to extract honest customer feedback