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 In episode 734, Rob Walling interviews Ian Landsman, founder of HelpSpot, about his 20-year bootstrapper journey. They discuss Ian's transition from on-prem software to SaaS, the challenges and benefits of each, and the early days of building the business. They wrap up by discussing the potential impact of AI on the customer service industry. Topics we cover: 1:11 – Ian, the OG bootstrapper 2:22 – Benefits of on-prem software in 2024 5:46 – Slow, steady, profitable growth through the years 9:20 ...
Oct 08, 2024•35 min•Transcript available on Metacast In episode 733, join Rob Walling for a solo adventure where he covers several topics. In this episode he differentiates between good and bad distractions, weaknesses versus blind spots, and shares personal experiences of struggle. He concludes with actionable advice – uncover the blind spots, then launch, iterate, and take feedback. Topics we cover: 2:09 – Not all distractions are bad 5:42 – The worst distractions masquerade as productivity 9:48 – Weaknesses versus blind spots 16:41 – Everybody ...
Oct 01, 2024•27 min•Transcript available on Metacast In episode 732, Rob Walling interviews Jeff, a mostly anonymous and retired founder, about his mostly bootstrapped business and subsequent exits. Jeff shares how he started the company in 2003 and how he persevered in the early, lonely years to achieve traction in the business. They also discuss finding fulfillment after a huge, life-changing exit. Topics we cover: 2:17 – Jeff, the retired SaaS founder you haven’t heard of 3:32 – Refreshing the bank balance after multiple exits 5:26 – ARR multip...
Sep 24, 2024•36 min•Transcript available on Metacast In episode 731, join Rob Walling and Derrick Reimer as they tackle some more advanced listener questions. They discuss delegation and giving up areas of control as a founder, including examples from their time together at Drip. Derrick describes how he approaches partnering with other SaaS businesses and why planning a full quarter ahead doesn’t work for many bootstrapped founders. Episode Sponsor: Hiring senior developers can really move the needle in your business, but if you bring on the wron...
Sep 17, 2024•49 min•Transcript available on Metacast In episode 730, Craig Hewitt turns the table and interviews Rob Walling about releasing The SaaS Launchpad course. Craig, founder of Castos, asks Rob about the course's purpose and structure, which founders that it’s designed for, and why he made a course as opposed to a new book, or a YouTube series. They also discuss the pricing strategy, hosting platforms, accountability, community, and more. If you’re trying to take your SaaS from zero to one, purchase The SaaS Launchpad before September 30t...
Sep 10, 2024•38 min•Transcript available on Metacast In episode 729, join Rob Walling as he shares insights from the 170+ SaaS investments he’s made through his B2B SaaS accelerator, TinySeed. Key patterns include the survivability of SaaS, the lucrative value of these companies, and commonalities across the ones that grow the fastest. To see even more patterns that didn’t make this episode, be sure to check out the MicroConf YouTube channel. Episode Sponsor: Hiring senior developers can really move the needle in your business, but if you bring on...
Sep 03, 2024•25 min•Transcript available on Metacast In episode 728, Rob Walling interviews Eran Galperin, founder of Gymdesk, about his incredible exit. Eran shares his journey of transforming Gymdesk from "Martial Arts on Rails" into a successful gym management software company. He discusses how they succeeded in a competitive market, the role of TinySeed in their growth, and how feelings of burnout eventually led to a majority buyout for the company. Topics we cover: 2:02 – Gymdesk Announces a $32.5 Million Strategic Growth Investment 5:13 – Ho...
Aug 27, 2024•36 min•Transcript available on Metacast In episode 727, Rob Walling is joined by Tracy Osborn and Einar Vollset to give their hot takes on some recent news. First they celebrate Gymdesk’s recent funding and evaluate what that means for TinySeed companies. Then, they weigh in on bootstrapper hiring, grappling with new challenges as MRR grows, and how to really move the needle in your business. Episode Sponsor: Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly bur...
Aug 20, 2024•30 min•Transcript available on Metacast In episode 726, join Rob Walling for a solo adventure where he covers several topics. In this episode he reveals the sales details around “The SaaS Playbook” by sharing the volume and sales channel data. He explores the importance of motivation over mere access to information, particularly for developers, with the introduction of AI. Rob also previews several exciting projects to be released in the near future. Topics we cover: 2:49 – The SaaS Playbook sales channel breakdown 8:20 – Learnings fr...
Aug 13, 2024•24 min•Transcript available on Metacast 
