How do you build an MVP for an AI-enabled SaaS? In episode 764, Rob Walling interviews Jordan Gal, co-founder of Rosie, to learn about how he pivoted from Rally to build an AI-driven product for small business owners. Jordan shares insights into the challenges of finding product-market fit, the importance of trial and error, and the rapid growth Rosie has experienced since its launch. They delve into the significance of effective onboarding, and how building an MVP changes in the face of AI. Top...
Mar 11, 2025•40 min•Transcript available on Metacast Is it time to set a deadline for when to quit your startup? In this episode of TinySeed Tales, Rob Walling reconnects with Colleen Schnettler, co-founder of Hello Query, as she tries to achieve product-market fit on a deadline. Colleen reveals the struggles of cold outreach and the overwhelming data landscape while testing a potential solution. With a clearer vision and two paying customers, she reflects on the importance of defining her value proposition, and the critical timeline she has set f...
Mar 06, 2025•15 min•Transcript available on Metacast Are public deadlines a double-edged sword for startup founders? In episode 762, join Rob Walling for a solo adventure where he covers several topics. Rob breaks down Paul Graham's essay, "Doing Great Work" and focuses on how the steps apply to building real businesses for real customers. He also discusses the hierarchy of skills necessary for success in the SaaS space, sharing his thoughts on the critical roles of marketing, product development, engineering, and effective team management. Topics...
Mar 04, 2025•25 min•Transcript available on Metacast In this episode of TinySeed Tales, Rob Walling checks in with Colleen Schnettler, co-founder of Hello Query, as she discusses finding customer pain points. Colleen, now solo, navigates the challenge of refining her product vision. After a period of introspection, Colleen shares her decision to pivot from targeting engineering managers to focusing on marketing data analysts. She discusses the insights gained from hiring a marketing coach and the excitement of landing her first paying customer, de...
Feb 27, 2025•21 min•Transcript available on Metacast In episode 760, join Rob Walling as he takes on some listener questions in another solo adventure. He offers insights on balancing custom-built solutions versus white-labeled components, and the impact white labeling has on company valuation and growth. He also discusses strategic hiring, founder mindsets, and tools for tracking your SaaS success. Topics we cover: (2:30) – Considerations when white-labeling within your SaaS (9:03) – Does relying on other SaaS affect our valuation? (10:10) – Tool...
Feb 25, 2025•33 min•Transcript available on Metacast In this episode of TinySeed Tales, Rob Walling speaks with Colleen Schnettler, co-founder of Hello Query, as she shares her latest startup journey pivot. After reigniting her “shipping muscle” while briefly dabbling in an AI-based project, Colleen refocuses on her newest pivot of Hello Query. She shares the challenges of determining the market viability of an AI-assisted SQL report builder. She stands at a crossroads, torn between catering to internal BI teams or exploring marketing analytics. T...
Feb 20, 2025•27 min•Transcript available on Metacast In episode 758, Rob Walling is joined by Derrick Reimer to tackle a variety of listener questions. They discuss strategies for entering a market with established competitors, including how to position your product without directly attacking rivals. They also reflect on the challenges of free trials, weighing the pros and cons of extending trial periods versus incentivizing onboarding. Episode Sponsor: Most marketing agencies promise growth but never move the needle. But Corey Haines and the team...
Feb 18, 2025•45 min•Transcript available on Metacast In this episode of TinySeed Tales, Rob Walling chats with Colleen Schnettler, co-founder of Hello Query, as she navigates the complexities of her startup journey. After a challenging period with her co-founder Aaron, Colleen reflects on their decision to part ways and the emotional toll it has taken on her. She shares her feelings of crushing failure, the uncertainty of moving forward alone, and the realization that their initial product vision may not align with market needs. Topics we cover: (...
Feb 13, 2025•15 min•Transcript available on Metacast In episode 756, Rob Walling interviews Brendan Fortune, Director of Product Management at Customer.io, to explore the skills and frameworks for effective product management. Brendan shares his journey and discusses the importance of understanding customer behavior to drive product decisions. They delve into the concept of the flywheel and how it can be leveraged to enhance user success and optimize pricing strategies. Topics we cover: (2:46) – What does a product manager do? (10:36) – When shoul...
Feb 11, 2025•43 min•Transcript available on Metacast In this episode of TinySeed Tales, Rob Walling checks in with Colleen Schnettler, co-founder of Hello Query, as she shares the latest developments in her startup journey. Colleen shares the insights gained from recent customer interviews that led to a significant pivot in their product strategy. Hello Query is now focused on embedding custom reporting features within other SaaS applications and Colleen reflects on balancing product quality with minimal v1 features. Her excitement is building to ...
Feb 06, 2025•16 min•Transcript available on Metacast In episode 754, join Rob Walling for a solo adventure as he tackles listener questions on a variety of topics. He discusses strategies for converting free users to paid customers, the implications of AI advancements on the SaaS landscape, and how to navigate platform risks when larger players enter your market. Rob also shares insights on breaking through growth plateaus. Topics we cover: (3:12) – When in doubt, don’t try freemium (6:44) – Different levers you can pull to make freemium work (8:5...
Feb 04, 2025•25 min•Transcript available on Metacast In this episode of TinySeed Tales, Rob Walling reconnects with Colleen Schnettler, co-founder of Hammerstone, as she shares the latest developments in their startup journey. Colleen opens up about the emotional challenges of co-founder conflicts with Aaron, highlighting the importance of communication and alignment in their partnership. They also discuss the significant pivot from their initial product offering to the newly rebranded Hello Query, a SaaS solution focused on internal reporting for...
Jan 30, 2025•23 min•Transcript available on Metacast In episode 752, Rob Walling interviews Lars Lofgren to discuss the current state of SEO. Lars shares insights on how SEO has drastically changed, especially with the rise of AI and the volatility brought on by Google’s evolving algorithm. They cover the challenges of ranking for terms, the impact of AI content, and the rise of "parasite SEO." Topics we cover: (2:16) – SEO traffic that generates $7.2M annual revenue (4:54) – Changes in Google’s algorithm (9:46) – How to approach SEO as a bootstra...
Jan 28, 2025•36 min•Transcript available on Metacast In this episode of TinySeed Tales, Rob Walling catches up with Colleen Schnettler, co-founder of Hammerstone, about the progress her team has made since their initial check-in. Colleen describes the tough decision to focus on one product stack, and their recent pivot toward building a reporting MVP. They also discuss Colleen’s shift into a more managerial role. Topics we cover: (2:10) – Motivations behind building additional functionality (7:07) – Repositioning the reporting dashboard (10:08) – ...
Jan 23, 2025•31 min•Transcript available on Metacast In episode 750, Rob Walling is joined by Laura Roeder, founder of Paperbell, to answer intermediate listener questions. They discuss making your first hire with limited funds, testing pricing models with existing customer bases, and more. Laura also provides some great advice on content marketing, drawing from her past experience at MeetEdgar. Topics we cover: (3:14) – Building a team before you can afford your first, full time hire (11:11) – Testing pricing with existing customer bases (19:00) ...
Jan 21, 2025•36 min•Transcript available on Metacast Welcome to Season 4 of TinySeed Tales, where we follow the founders of one SaaS startup throughout a few years as they share their struggles, victories, and failures. In the first episode of Season 4, Rob introduces us to Colleen Schnettler, the cofounder of Hammerstone. Colleen is a self-taught Rails developer, and this season will follow how Hammerstone eventually becomes Hello Query – an AI-powered chatbot that runs custom reporting on your data. Colleen is one of 27 startup founders from Tin...
Jan 16, 2025•26 min•Transcript available on Metacast In episode 748, Rob Walling sits down with Einar Vollset, co-founder of TinySeed, to discuss the ins and outs of startup investing. They explore the differences between VC and angel investing, the importance of deal flow, and the challenges of valuation. Rob and Einar also highlight how TinySeed’s approach differs from traditional VC, including their focus on capital efficiency and why it’s been working for ambitious B2B SaaS companies. Topics we cover: (2:37) – The stigma of bootstrapper fundin...
Jan 14, 2025•39 min•Transcript available on Metacast In episode 747, Rob Walling interviews Jane Portman, co-founder of Userlist, to discuss the evolution of their SaaS customer success strategy. Jane shares the four stages of Userlist’s customer success journey, from the early days of trial and error to implementing done-for-you services. They also discuss the challenges of customer onboarding for complex products. Topics we cover: (2:20) – How customer success works at Userlist (5:27) – Dealing with upfront onboarding friction (9:51) – Stage 1, ...
Jan 07, 2025•36 min•Transcript available on Metacast In episode 746, Rob Walling looks ahead to 2025 with nine startup predictions, exploring trends in no-code tools, search, autonomous vehicles, AI, and an increase in platform risk for bootstrapped founders. Topics we cover: (1:52) – Carrying forward predictions from 2024 (3:09) – Search volume for Google organic SEO (6:34) – Ads in AI interfaces (7:50) – Google’s revenue drops, bootstrapper opportunities (10:07) – “AI” use in H1’s (14:01) – Self-driving taxis (19:28) – Platform risk intensifies ...
Dec 31, 2024•22 min•Transcript available on Metacast In episode 745, Rob Walling goes solo to reflect on 2024. He revisits key concepts and frameworks introduced on the podcast, including the 2-20-200 Validation Framework, Orthogonal SaaS, and the eight levels of platform risk. Rob also looks back at his top five favorite episodes and reviews his predictions for the year—some of which came to pass, and others that didn’t. Topics we cover: (2:05) – Looking back at concepts and frameworks from past 12 months (8:50) – Rob’s 5 favorite episodes (11:56...
Dec 24, 2024•27 min•Transcript available on Metacast In episode 744, Rob Walling is joined by Tracy Osborn and Einar Vollset to give their hot takes on some recent news. They cover the recent rise of Bluesky, kicking off a 4-figure bet between Tracy and Einar. Then they discuss TinySeed’s third fund, YC Combinator backing competitors, dealing with imposter syndrome, and finally government involvement in banning social media. Topics we cover: (1:49) – Will Bluesky survive and thrive? (9:07) – The bet on Bluesky growth (13:46) – TinySeed is raising ...
Dec 17, 2024•34 min•Transcript available on Metacast In episode 743, Rob Walling and Dr. Sherry Walling read the first chapter of their new book, Exit Strategy: The Entrepreneur’s Guide to Selling Your Company Without Regret. They discuss the emotional and psychological challenges of selling a business, and why it’s often harder than founders expect. They offer insights on how to prepare for a sale, protect your mental health, and how to best navigate this major life change that few others understand. Back the book on Kickstarter Episode Sponsor: ...
Dec 10, 2024•37 min•Transcript available on Metacast In episode 742, Rob Walling goes solo to explore normalizing doing hard things and facing your biggest threats. He also discusses a framework for founders looking to scale without cutting corners – making things work, making them right, and then making them fast. Exit Strategy Kickstarter ends on December 12! Topics we cover: (2:39) – Normalizing doing hard things (6:54) – The “hard things” in your startup (10:27) – Walking into the storm (16:21) – ”Make it work, make it right, make it fast” (22...
Dec 03, 2024•28 min•Transcript available on Metacast In episode 741, Rob Walling talks to Wes Bush, CEO and Founder of ProductLed, about the nuances and misconceptions of product-led growth. Wes debunks common myths and explains how companies can leverage their product to drive user acquisition, engagement, and growth. They dive into a real-world example and explore how founders can avoid the trap of thinking the product will “sell itself” while contrasting PLG and sales-led strategies. Episode Sponsor: Hiring senior developers can really move the...
Nov 26, 2024•32 min•Transcript available on Metacast In episode 740, Rob Walling speaks with Dr. Sherry Walling about their new book, "Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret." They explore the emotional, psychological, and practical aspects of selling a business, emphasizing the universal challenges entrepreneurs face. The book draws on both Rob and Sherry’s unique experiences that they’ve shared with countless founders throughout their careers. Exit Strategy is now live on Kickstarter! Topics we cover: 2:0...
Nov 19, 2024•30 min•Transcript available on Metacast In episode 739, Rob Walling interviews Andy Kim, co-founder of Trotto, about his unique journey into SaaS. Andy shares how “go links” work, and why they are so valuable for internal, enterprise use despite their relative obscurity. They also explore the marketing hurdles and customer adoption challenges in a business like Trotto. Episode Sponsor: Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. I...
Nov 12, 2024•30 min•Transcript available on Metacast In episode 738, join Rob Walling for a solo adventure as he answers listener questions. He explores how to target larger, enterprise deals after achieving product-market fit, and why word of mouth marketing can be great, yet is tricky to control. Rob also answers a later-stage question and cautions against trying to educate the market as a bootstrapper. Topics we cover: 1:58 – Expanding to enterprise deals after product-market fit 6:39 – Word of mouth marketing is tricky for B2B SaaS 14:36 – Edu...
Nov 05, 2024•29 min•Transcript available on Metacast In episode 737, Rob Walling is joined by Derrick Reimer to recap the experience from MicroConf Europe 2024 in Dubrovnik. They discuss the differences between MicroConf US and MicroConf Europe, some small programming tweaks over the years, and they revisit the highlights from the talks at this event. If you missed the event and had some MicroConf FOMO, get your tickets now for our New Orleans event! Episode Sponsor: Hiring senior developers can really move the needle in your business, but if you ...
Oct 29, 2024•42 min•Transcript available on Metacast In episode 736, join Rob Walling as he answers some later-stage listener questions in another solo adventure. He discusses common pitfalls in delegation, transitioning from one-time transactions to SaaS models, and when it makes sense to target multiple ICPs. Rob also warns about the limited impact that social media marketing can have on growing your SaaS tool. Episode Sponsor: Are you drowning in challenging tech decisions? You should check out today’s sponsor, Techstack . Unlike typical staffi...
Oct 22, 2024•28 min•Transcript available on Metacast In episode 735, join Rob Walling for a solo adventure where he categorizes the different levels of SaaS platform risk. He introduces a framework with three key factors: Replacement, Customer Concentration, and Lead Flow. Rob then defines eight levels of risk according to these factors and other vulnerabilities such as relying on open source – a hot topic with recent news about WordPress, WP Engine, and Automattic. Episode Sponsor: Hiring senior developers can really move the needle in your busin...
Oct 15, 2024•27 min•Transcript available on Metacast 
