Episode 804 | Positioning, Inventing a Category, Marketing Globally, and More Listener Questions (A Rob Solo Adventure)

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

Can churn ever be good in SaaS? In this episode, Rob Walling is joined by fan favorite Derrick Reimer for a listener Q&A. They break down what it takes to compete with well-funded incumbents, how to decide whether to pivot or push forward, when a technical co-founder is truly necessary, the right time to think about trademarks, and the difference between “good churn” and “bad churn” especially when customers fall outside your ICP. Episode Sponsor: AI is completely changing how people discover brands and content online, and Ahrefs has built a full-blown SaaS marketing platform to help you stay ahead. With over 15 years of real-world web data, and AI that actually understands marketing, Ahrefs helps you measure your brand presence, build authority, and monitor reputation across search, social, and AI platforms like ChatGPT, Google AIOs, Perplexity, and more. You can also dig into what’s driving your competitors’ visibility and spot market gaps before they do, helping you create content that ranks and drive new traffic to your business. There's no need to juggle a bunch of disconnected tools- get Ahref’s all-in-one platform to make your brand unmissable in a fast-moving world.  Try it free at ahrefs.com/awt. Topics we cover:  (3:35) – Competing with well-funded incumbents (12:47) – Should you focus on competitors or customers? (20:20) – Pivot, press on, or move on: how to decide (29:09) – Finding and vetting a technical co-founder or partner (39:04) – When should you pursue trademarks? (44:24) – Is churn ever good for a startup? Links from the Show:  MicroConf US 2026 - Portland, Oregon - Use Promo Code ROB50 for $50 off. MicroConf Connect BIMI (Brand Indicators for Message Identification) SavvyCal 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 if you could get all 15 years of this podcast bundled up into one episode?  In episode 800, Rob Walling goes solo for a special milestone installment of Startups For the Rest of Us. He covers the 12 foundational commandments that shape his approach to SaaS, hard-won lessons forged from years of building, investing in, and advising startups. Topics we cover:  (3:46) – #1: Nuance beats absolutes (6:52) – #2: Make hard decisions with incomplete information (9:16) – #3: Avoid the classic traps (12:22) – #4: Don't build without real evidence (15:14) – #5: Marketing beats product (19:08) – #6: Fewer customers, better customers (21:01) – #7: Respect (and fear) the platform (24:04) – #8: Build your network, not just your audience (26:30) – #9: Overnight success takes a decade (28:45) – #10: Stack small wins (31:22) – #11: Be careful who you listen to (33:15) – #12: The hardest battles are in your own head Links from the Show: MicroConf US 2026 - Portland, Oregon - Use Promo Code ROB50 for $50 off. Invest in TinySeed Fund Three SaaS Playbook The Entrepreneur's Guide to Keeping Your Sh*t Together Exit Strategy Episode 685 | 7 Things You Should Never Do Episode 700 | Playing the Long Game Episode 735 | The 8 Levels of SaaS Platform Risk 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 next for OutboundSync? In the Season 5 finale of TinySeed Tales, Rob Walling talks with Harris Kenny as OutboundSync blows past $500k ARR. Harris shares the wins and struggles of getting here, from choosing not to raise funding (for now), to planning a laser tag event no committee would approve, to what comes next on the road to $1M. Topics we cover:  (1:49) – Crossing $500k ARR and building personal health habits (5:36) – The big levers behind OutboundSync’s growth (6:39) – Laser tag, not hotel happy hours (13:01) – Deciding not to raise more funding (for now) (16:25) – An overbuilt tech stack  (17:57) – Competitors, copycats, and growing a brand (19:06) – The next chapter for OutboundSync (23:29) – Ambition, TinySeed, and channeling energy (25:14) – Harris’s advice for founders still grinding Links from the Show:  Invest in TinySeed Fund Three Coaching Call Bonus OutboundSync Harris Kenny | 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 do you bootstrap a SaaS to $1 million+ ARR? In this episode, Rob Walling chats with Colin Bartlett about how he and his co-founder Andy transformed a side project monitoring tool into a seven-figure ARR business that now serves as an early warning system for outages across 6,000+ services.  From nearly abandoning the product during three stagnant years to discovering their killer differentiation, Colin's journey is a masterclass in patient iteration, finding product-market fit the hard way, and why sometimes the most boring infrastructure businesses make the best SaaS companies. Episode Sponsor: You’ve probably heard that ChatGPT can do all of your marketing. But that’s nonsense unless your strategy is blindly following tired, recycled, outdated strategies.  If you care about systematically creating a marketing engine that converts, not just throwing spaghetti at the wall to see what sticks, you need real humans who actually understand positioning, persuasion, and modern customer acquisition playbooks.  That’s Conversion Factory. They’re a SaaS marketing and design agency that have worked with over 50 startups, including several TinySeed companies.  Book a call at conversionfactory.co and mention this podcast for $1,000 off your first month. And if you’re at MicroConf Europe next week, make sure to connect with Corey Haines in the hallway track.  Topics we cover:  (3:08) – How StatusGator detects outages (and why users are part of the signal) (6:23) – From side project to SaaS: the early days of building StatusGator (8:46) – Shifting the ICP: Why developers weren’t the buyers (11:44) – SEO as the engine behind thousands of trials (17:00) – Hitting early MRR milestones and hiring the first marketer (25:12) – How TinySeed funding unlocked a full product redesign (32:05) – Building a dual funnel to boost ACV and win enterprise deals (38:00) – Advice for other SaaS founders playing the long game Links from the Show:  Invest in TinySeed Fund Three MicroConf Mastermind Matching - Applications open until September 24th StatusGator Colin Bartlett | 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

OutboundSync just hit $35k MRR—but the decisions are only getting harder.  In this episode of TinySeed Tales, Rob Walling and Harris Kenny dive into the messy middle of SaaS growth, where every opportunity comes with a trade-off. They explore the tension between raising funds you don't need, staying focused when good ideas keep coming, and building a business while raising a family. Topics we cover:  (2:28) – From $20k to $35k MRR in three months (2:53) – The bets that moved the needle (4:56) – Infinite runway, SOC 2 wins, and building trust (8:29) – Saying no to good ideas with limited bandwidth (10:00) – Decision-making, value-driven growth, and agency DNA (13:14) – Should Harris raise more funding or stay focused? (15:52) – Why boring “pipes” matter in an AI world (20:25) – Trade-offs, mindset, and building for scale (25:35) – Hiring a sales coach and focusing on what works (27:52) – Balancing startup stress with parenting Links from the Show:  SaaS Institute Coaching Call Bonus OutboundSync Harris Kenny | 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

What if your SaaS isn’t growing because of the product, not the marketing? In this solo adventure episode, Rob Walling unpacks why SaaS marketing feels harder than ever and why most advice out there will waste your time. He shares how he’d approach things if growth has stalled, the questions he’d ask first, and why real progress comes from proven fundamentals. Episode Sponsor: Is your engineering team stretched too thin? Gearheart provides growing companies with AI-powered engineering talent that ships 2 times faster.  CTOs and engineering managers trust them to deliver critical features end-to-end with minimal oversight, whether it's fixing scaling failures, broken integrations, or system instability.  With 13 years of experience building sophisticated B2B platforms, they plug in fast and deliver results. They've helped build platforms like SmartSuite, which has scaled to thousands of organizations including industry giants like Capital One. Book your free strategy session at gearheart.io and mention this podcast to get 20% off discovery or embedded engineers for your team. That's gearheart.io. Topics we cover:  (2:20) – Why marketing is harder than ever, and what’s changed (3:40) – The Dunning-Kruger Effect  (11:30) – Marketing is not just convincing someone to buy what you've built. (16:30) – Validating vs. throwing dice at a wall (20:03) – Is there a ‘one right way’ to grow a business? (25:00) – Be careful who you listen to Links from the Show:  MicroConf Events MicroConf Mastermind Matching 75+ SaaS Marketplaces  The SaaS Playbook TinySeed Rob Walling (@robwalling) | 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

Harris hit $20k MRR. It’s real. What’s next? In this episode of TinySeed Tales, Rob Walling celebrates with Harris Kenny after OutboundSync crosses $20k MRR ahead of schedule. They talk about why hitting a milestone can feel both exciting and overwhelming, the arrival fallacy, and how simple, consistent execution may be all it takes to reach $30k. Harris shares the bets that moved the needle, including Salesforce, SOC 2, and what hidden demand taught him about building integrations before anyone asked. Topics we cover:  (1:32) – Crossing $20k MRR and aiming for $30k (6:29) – The Salesforce bet (8:17) – Runway, burn, and pricing upmarket (10:34) – Raise capital or keep bootstrapping (15:03) – SOC 2 as a sales unlock (20:11) – Marketplace credibility and AppExchange (22:05) – Hidden demand for Salesforce (26:11) – The push to $30k and parity Links from the Show:  Invest in TinySeed Fund 3 Coaching Call Bonus MicroConf Events OutboundSync Harris Kenny | 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