Scaling SaaS Smarter: Growth & Retention Strategies with Rob Walling
September 16, 2025
Rob Walling has launched and sold SaaS products, invested in over 200 startups, and built a global founder community, so he knows the patterns behind success and failure. In this episode of SaaS That App: Building B2B Web Applications, the TinySeed co-founder joins Aaron Marchbanks and Justin Edwards to break down why most early SaaS idea validation is done wrong, the 7 plateaus every founder will hit, and the “cheat codes” that can accelerate growth. He shares how to think about churn and expansion revenue, why pricing is your biggest lever, and why even seasoned founders can’t shortcut the grind of building a profitable SaaS business.
This podcast is brought to you by Delta Systems, your one-stop shop for front-end, back-end, and full-stack software development. At Delta, Justin and Aaron share the same philosophy when it comes to clients: they treat people like colleagues, not just customers. Maybe that’s why Delta typically spends years working with the same companies: how many software engineering firms can you say that about? So, if you’ve got a SaaS project in mind but have no idea where to start, come and get a free scope and estimate from Delta Systems on their website.
Got a burning idea for an episode, or a SaaS question you absolutely must know the answer to? Leave us a voice memo at SaasThatApp
Rob Walling has launched and sold SaaS products, invested in over 200 startups, and built a global founder community, so he knows the patterns behind success and failure. In this episode of SaaS That App: Building B2B Web Applications, the TinySeed co-founder joins Aaron Marchbanks and Justin Edwards to break down why most early SaaS validation is done wrong, the 7 plateaus every founder will hit, and the “cheat codes” that can accelerate growth. He shares how to think about churn and expansion revenue, why pricing is your biggest lever, and why even seasoned founders can’t shortcut the grind.
What You’ll Learn:
- Why friends and family aren’t validation (and what is)
- How to predict plateaus before you hit them
- The four SaaS “cheat codes” and when they apply
- Why product and engineering are two different roles (and why that matters)
- The psychology of being a founder and how to survive it
- When to think about an exit (and how to avoid regretting it)
Rob Walling is a serial entrepreneur, investor, and author who has built, scaled, and sold multiple SaaS companies, including Drip. He’s the co-founder of TinySeed, the first startup accelerator for bootstrapped SaaS founders, and MicroConf, a global community for indie software entrepreneurs. Through TinySeed, he has invested in more than 200 startups, helping founders grow sustainable, capital-efficient businesses without chasing unicorn status. Rob hosts the long-running Startups for the Rest of Us podcast, has authored The SaaS Playbook and Exit Strategy, and is known for his practical, no-BS approach to building and exiting profitable SaaS companies.
This podcast is brought to you by Delta Systems, your one-stop shop for front-end, back-end, and full-stack software development. At Delta, Justin and Aaron share the same philosophy when it comes to clients: they treat people like colleagues, not just customers. Maybe that’s why Delta typically spends years working with the same companies: how many software engineering firms can you say that about? So, if you’ve got a big SaaS project in mind but have no idea where to start, come and get a free scope and estimate from Delta Systems on their website.
Highlights:
Highlights:
- [00:00] Introduction
- [01:21] From Construction to Coding to SaaS
- [03:43] The Problem with Most SaaS Validation
- [05:53] How Drip Started (and Plateaued)
- [08:16] Why Validation Isn’t 100% Proof
- [11:50] The Three Reasons SaaS Plateaus Early
- [13:21] The 7 Post-Product-Market Fit Plateaus
- [16:44] SaaS Cheat Code #1: Expansion Revenue
- [20:33] Net Negative Churn Explained
- [22:39] When Cheat Codes Don’t Apply
- [25:22] The Grind; Even for Experienced Founders
- [28:40] Managing Founder Psychology
- [34:27] Thinking About an Exit (and Doing It Without Regret)
- [41:03] What TinySeed Looks for in Founders
Episode Resources:
- Rob Walling’s Website
- Rob Walling on LinkedIn
- Startups for the Rest of Us Podcast
- MicroConf YouTube Channel
- TinySeed Website
- The SaaS Playbook: Build a Multimillion Dollar Startup Without Venture Capital
- Exit Strategy: The Entrepreneurs Guide to Selling Your Business Without Regret
- Aaron Marchbanks on LinkedIn
- Justin Edwards on LinkedIn
- Delta Systems Website
Got a burning idea for an episode, or a SaaS question you absolutely must know the answer to? Leave us a voice memo at SaasThatApp
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Your input helps us shape future episodes and continue bringing you practical, real-world insights into building B2B web applications.