Can bootstrapped founders really invent a new category with AI or is it a trap?

In this solo episode, Rob Walling answers a fresh batch of listener questions covering SaaS marketing, global expansion, and strategic positioning. He shares advice on whether inventing a new product category is ever worth it and the nuances of updating your positioning after launch.

Want to get your question answered? Drop it here.

Topics we cover:

(2:53) – Vertical vs. horizontal vs. orthogonal positioning as a bootstrapper
(12:37) – Is AI making it easier to create a new category?
(21:19) – How to break through mental blocks and actually launch
(28:36) – Local vs. global marketing for SaaS
(33:01) – Self-driving cars: Rob’s past prediction and what reverse statistics can teach founders

Links from the Show:

MicroConf Remote - Nov 5th, 2025 | Use promo code STARTUPS15 for 15% off your ticket.
TinySeed - SaaS accelerator for ambitious B2B founders
Invest in TinySeed
Episode 783 | Bootstrapping ScrapingBee to $5M ARR and an 8-Figure Exit
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Episode 804 | Positioning, Inventing a Category, Marketing Globally, and More Listener Questions (A Rob Solo Adventure)

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