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.

• (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

• 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!

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What's it really like to attend MicroConf?

In this episode, Rob Walling and Laura Sprinkle, founder of Rootabl, recap MicroConf Europe 2025 in Istanbul. They discuss the MicroConf vibe, standout talks on AI, affiliate marketing, and SaaS growth, as well as the value of networking and connecting while getting outside the conference room.

• (5:01) – The friendly, diverse MicroConf crowd
• (8:06) – Impressions on Istanbul
• (9:24) – Marc Thomas on lifecycle marketing
• (11:34) – Michelle Hansen & John Knox on networking
• (13:04) – MicroConf Excursions
• (16:45) – Einar Volset on SaaS Buyers
• (20:27) – Rob’s AI talk
• (23:27) – Laura’s talk about affiliate programs
• (24:47) – Jesse Schoberg on ranking in ChatGPT and Google's AI
• (26:31) – Attendee-Led Workshops
• (27:58) – Kevin Sahin’s unfiltered lessons scaling to $2M
• (31:12) – James Mooring’s journey to $2M ARR

• Get your Ticket for MicroConf - Portland, Oregon, on April 12 -14, 2026 | Use promo code ROB50 for $50 off your ticket.
• TinySeed
• Join MicroConf Connect
• Deploy Empathy by Michelle Hansen
• The Hard Thing About Hard Things by Ben Horowitz
• There’s ONLY 5 Ways to Use AI in SaaS (prove me wrong)
• Rob Walling (@robwalling) | X
• Rootabl
• Laura Sprinkle | LinkedIn
• Laura Sprinkle (@imlaurasprinkle) | X

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

Where’s the best place to publish if you’re starting content from scratch?

In this episode, Rob Walling flies solo, answering your questions on marketing and audience building. He covers what to do when your channels stop scaling, where to publish early on, and the "media company first" approach.

Episode Sponsor:

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If it’s a fit, you can move on to SolutionLab, a three-week sprint where Designli takes over your codebase and architects a real roadmap for growth, led by a full-time, cross-functional team.

If your tech is the bottleneck to your next stage of growth, check them out at https://designli.co/fortherestofus.

• (1:50) – Can a SaaS founder exit through a management buyout?
• (6:46) – What to do when your marketing isn't scaling anymore
• (16:28) – How to market a product while searching for product-market fit
• (23:27) – Where to publish content when building an audience from scratch
• (27:38) – Should you build a media company before launching your SaaS?

• Get your Ticket for MicroConf Remote - November 5, 2025
• Exit Strategy
• The SaaS Playbook
• Rob Walling (@robwalling) | X
• Episode 576 | Don’t Become a Media Company (A Rob Solo Adventure)

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