Is hiring a sales and marketing co-founder the secret sauce for technical SaaS founders?

In this solo episode, Rob Walling tackles a fresh batch of listener questions, starting with one of the most common dilemmas for technical founders: should you hire a sales and marketing co-founder or go it alone?

He introduces his “Core Four” mental model, the essential skills every SaaS team needs early on, and shares insights on dealing with enterprise clients who keep moving the goalposts, handling a flood of non-ICP users, and a heartfelt message from a listener who just exited their startup.

Want to get your question answered? Drop it here.

Episode Sponsor:

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• (3:11) – Should you find a co-founder for sales and marketing?
• (5:29) – What are the Core Four SaaS Skills?
• (11:41) – Can you succeed without mastering all four, or should you outsource?
• (16:39) – Why sales-led growth might outperform self-serve SaaS
• (21:48) – Dealing with big companies who change your contract terms
• (27:06) – What to do with thousands of unqualified signups

• Discretion Capital – M&A for B2B SaaS
• Exit Strategy by Sherry & Rob Walling
• MicroConf - SaaS Community
• TinySeed - SaaS Institute

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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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:

Are you a non-technical founder with solid revenue and real traction, but your technology is holding you back? You should check out today's sponsor, Designli.

They specialize in helping founders like you who are stuck with messy code, unclear roadmaps, or a dev team that just doesn’t get it.

And for listeners of the pod, Designli is offering their Impact Week completely free. That’s a one-week, no-obligation audit where their team dives into your code, your design system, and your product roadmap to show you exactly what’s working, what’s broken, and what needs to happen next.

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.

• (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