Running Your Own Race: Tom Lavery on going from bootstrapped to venture-backed

What does it take to build a category-defining SaaS company when your biggest competitors have raised 40x more funding than you?

In this episode, Tom Lavery, Founder & CEO of Jiminny, joins us to share how he bootstrapped for years before raising, why staying in control beats chasing hype, and how to layer AI into GTM without over-engineering your stack.

Expect pragmatic tactics for capital-efficient growth, candid lessons from fundraising in a downturn, and a no-BS view on what’s truly changed in sales. 

Episode Chapters:

03:34 - Jiminny’s origin story 
05:53 - Competing in a category with 40x more capital  
09:21 - How to pick your investors & navigating the SaaS recession 
17:20 - What’s changed in sales 
21:18 - Successfully implementing AI 
31:18 - The European ecosystem 
33:18 - Slowing down and getting hiring right

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