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Can a small team really bootstrap to $8M ARR in a crowded SaaS market?

In this episode, Rob Walling chats with Philippe Lehoux about how he and his co-founders bootstrapped Missive, a collaborative email and team inbox tool. They deep dive into landing early customers, unique horizontal positioning, content-driven growth, enterprise sales, and how to compete with VC-backed competition.

Episode Sponsor:

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• (2:05) – Missive’s $8M ARR journey and email pivot
• (6:02) – Early idea and first customers
• (11:16) – Unique positioning: horizontal vs. vertical
• (13:41) – How they prioritize features
• (15:39) – Why they stayed bootstrapped and decline funding
• (20:25) – Content strategy and “vs” pages
• (21:39) – Affiliate program driving 30% of growth
• (25:24) – Challenges and benefits of being horizontal
• (30:28) – Enterprise sales and pricing
• (32:06) – Scaling with SOC 2 compliance

• SaaS Institute
• MicroConf YouTube channel
• Missive
• Philippe Lehoux | LinkedIn
• Philippe Lehoux (@plehoux) | 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!

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How much does your startup idea matter compared to your execution?

In this solo episode, Rob Walling covers several founder-focused topics: the difference between gatekeeping and paying your dues, why raw material beats polish, and why successful people don't mind others winning. He also shares a listener's exit story, discusses optimism in founder communities, and talks about the mix of luck, skill, and hard work needed to build something that lasts.

Episode Sponsor:

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• (2:00) – Gatekeeping vs. Paying dues as a new founder
• (9:56) – How “raw material” transforms into high-value skills (and startups)
• (16:36) – A bootstrapped listener shares a quiet, life-changing exit
• (18:17) – People who are winning don’t mind if others win too
• (20:09) – The critical importance of who you surround yourself with

• MicroConf Remote - Nov 5th, 2025 | Use promo code STARTUPS15 for $15 off your ticket.
• The SaaS Playbook
• 1000-Gram Iron Bar Analogy

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

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!

Subscribe & Review: iTunes | Spotify