Episode 811 | When to Delegate the "Core Four SaaS Skills," Freemium Retention Rates, and More Listener Questions (A Rob Solo Adventure)

How do you step back from daily decisions without losing control of your SaaS? In this episode, Rob Walling answers listener questions about when to delegate key founder skills, whether great founders can succeed with any idea, and the limits of no-code or “vibe-coded” apps.  To help answer one question, he calls up Ruben Gamez to get his insights on what “good” freemium retention really looks like and why the shape of your retention curve matters more than the number itself. Want to get your question answered? Drop it here. Episode Sponsor: Struggling to make Google Ads work for your SaaS? You’re faced with an impossible choice: spend thousands on an agency or waste months learning from outdated YouTube videos. That’s why Max Sinclair, a five-year MicroConf attendee, built SaaS Ads Studio  a software platform that combines AI with proven ad agency expertise to help SaaS founders launch, write, and optimize Google Ads campaigns. Think of it as an agency team in a box that gets you to a profitable Google Ads engine in about six months. Start for free at saasadsstudio.com and be one of the first 50 listeners to use code ROBWALLING for 50% off your first year.  Topics we cover:  (2:51) – What’s a “good” freemium retention rate? (4:59) – How freemium retention differs for mobile vs. SaaS apps (9:51) – When to start delegating the Core Four SaaS skills (12:53) – How to hand off sales, marketing, product, and dev the right way (23:28) – Can great founders succeed with any product idea? (29:34) – Should founders avoid building on no-code or third-party platforms? Links from the Show:  MicroConf Connect  TinySeed SaaS Institute The SaaS Playbook SaaS Launchpad SignWell Ruben Gamez | LinkedIn 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

How much design polish is really enough? In this episode, Rob Walling is joined by fan favorite Derrick Reimer for a new round of listener questions. They dig into the best AI coding stacks right now, how to ship fast without losing polish, whether AI is changing the kind of risk founders face, and when to start taking security seriously. 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.  Topics we cover:  (2:03) – What’s the best A.I. coding stack for developers right now? (11:14) – How can solo founders ship fast without sacrificing polish? (21:55) – Is A.I. shifting startup risk from market fit to feasibility? (31:44) – When should SaaS founders start worrying about security? (44:30) – SavvyCal’s latest product expansion Links from the Show:  Call for Speakers – Apply to speak at MicroConf US in Portland Claude Code Windsurf Cursor GitHub Copilot VS Code Visual Studio SavvyCal Appointments Derrick Reimer | LinkedIn Derrick Reimer (@derrickreimer) | 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

What are the can't-miss AI tools for SaaS founders? In this episode, Rob Walling sits down with Craig Hewitt, founder of Castos, to dive deep into Craig’s “100 Days of AI” YouTube series. They discuss the lessons learned from exploring the latest AI tools for founders, why ChatGPT might not be the best option for SaaS entrepreneurs, and which AI platforms are actually moving the needle.  Rob and Craig also chat about the realities of AI agents, the challenges of building a second product after hitting a growth plateau, and Craig’s approach to evaluating new opportunities as he looks to expand beyond podcast hosting. Episode Sponsor: AI is transforming how people discover brands and Ahrefs is helping SaaS companies stay ahead. They’ve just launched Brand Radar, a new tool that lets you track your visibility in AI platforms like ChatGPT, Perplexity, and Google’s AI Overviews. See how you stack up against competitors, monitor reputation, and build authority across search, social, and AI. No more cobbling together tools. Ahrefs brings it all into one powerful SaaS marketing platform, backed by 15+ years of real-world web data and marketing-savvy AI. Try it free at ahrefs.com/awt. Topics we cover:  (03:28) – 100 Days of AI YouTube series, biggest surprises and key takeaways (08:20) – Claude Code, ChatGPT, and Manus: Which AI tools work best for founders (13:00) – Practical AI workflows in content production and automation (18:35) – AI agent cuts customer support in half (21:27) – Burnout and breakthroughs from publishing 100 videos in 100 days (25:43) – Craig’s new AI projects and what’s next (30:14) – Three new product ideas under evaluation (33:09) – The pros, cons, and emotions behind launching a second product Links from the Show:  MicroConf US 2026- April 12-14, 2026 · Portland US TinySeed’s SaaS Institute Claude Code (by Anthropic)  Manus  Creator Hooks Cursor HelpScout DocsBot LinkBerry.ai – Craig’s new tool for LinkedIn content creation Castos Craig Hewitt | YouTube Craig Hewitt | LinkedIn Craig Hewitt (@TheCraigHewitt) | 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

Is it time to sell, autopilot, or double down on your plateaued SaaS business? In this episode, Rob Walling tackles listener questions and shares practical frameworks for what to do when your product hits a plateau, explains why “autopilot” often leads to decline, and outlines when founders should seriously consider SOC 2 compliance. Rob also talks about balancing a startup with a newborn, the real value of open source and IP, and the risks and rewards of building MVPs in exchange for equity. Want to get your question answered? Drop it here. Episode Sponsor: Need to ship faster without expanding your team? Gearheart is an AI-powered product studio that helps startups build B2B SaaS apps and AI agents, fast. Their team ships at twice the speed of traditional dev shops and understands how to work within startup constraints. Whether you need a fractional CTO or experienced engineers to accelerate development, Gearheart plugs directly into your workflow and delivers. They’ve built 70+ products, including SmartSuite, which raised $38M and is used by companies like Capital One. As a listener, you get the first 20 hours of development free when you mention the podcast. gearheart.io Topics we cover:  (2:34) – What to do with a plateaued $500k B2C app (4:28) – Founder motivation, business longevity, and the myth of autopilot (13:15) – Should you offer MVP development in exchange for equity? (14:04) – Equity risks, upside, and how to protect yourself (18:00) – When SOC2 compliance actually matters for founders (21:08) – Balancing a new baby, a job, and SaaS ambitions (24:38) – Can open source IP help bootstrappers stand out? (25:25) – Why differentiation and marketing matter more than patents or code Links from the Show:  Discretion Capital – M&A Advisory for B2B SaaS with $2-25m ARR MicroConf Connect 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! Subscribe & Review: iTunes | Spotify

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: Are you looking to hire world-class engineering talent without the headache? You should check out today’s sponsor, G2i. They give you access to over 8,000 pre-vetted developers, no AI-generated resumes, no time wasters, just experienced engineers with at least five years of proven results. G2i handles the vetting for you, including customized live technical interviews so you can see how a candidate would actually work with your team. Trusted by companies like Meta, Microsoft, and Shopmonkey, and especially helpful for first-time founders who need to get hiring right the first time. As a listener, you’ll get a 7-day free trial plus $1,500 off your first invoice when you mention this podcast. Head over to https://www.g2i.co/microconf  to get started. Topics we cover:  (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 Links from the Show:  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! Subscribe & Review: iTunes | Spotify

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.  Topics we cover:  (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 Links from the Show:  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! Subscribe & Review: iTunes | Spotify

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: AI is transforming how people discover brands and Ahrefs is helping SaaS companies stay ahead. They’ve just launched Brand Radar, a new tool that lets you track your visibility in AI platforms like ChatGPT, Perplexity, and Google’s AI Overviews. See how you stack up against competitors, monitor reputation, and build authority across search, social, and AI. No more cobbling together tools. Ahrefs brings it all into one powerful SaaS marketing platform, backed by 15+ years of real-world web data and marketing-savvy AI. Try it free at ahrefs.com/awt.  Topics we cover:  (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 Links from the Show:  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.  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

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.   Topics we cover:  (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 Links from the Show:  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: 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. Topics we cover:  (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? Links from the Show:  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