Do you disagree with any of these controversial takes about bootstrapping? In episode 768, Rob Walling unpacks a series of semi-controversial beliefs about bootstrapping from ScrapingBee’s Pierre de Wulf. Rob evaluates each point from Pierre's tweet, discussing topics like rebran … | Continue reading
Is product management more of an art, or a science? In episode 767, Rob Walling is joined again by Brendan Fortune to answer listener questions focused on product management. They discuss identifying your ideal customer profile, prioritizing feature requests, and positioning agai … | Continue reading
How do you achieve both success and longevity in SaaS? In episode 766, Rob chats with Steli Efti about growing Close.com to over $40 million in ARR. Steli shares insights into the importance of maintaining strong co-founder relationships over 12 years, navigating crises, and the … | Continue reading
Is it time to shut down for good? In this season finale of TinySeed Tales, Rob Walling sits down with Colleen Schnettler, founder of Hello Query, to reflect on her journey over the past few years. Colleen candidly shares the challenges she faced while trying to grow her SaaS busi … | Continue reading
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- … | Continue reading
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 t … | Continue reading
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 cu … | Continue reading
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 h … | Continue reading
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 strategi … | Continue reading
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 … | Continue reading
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 challe … | Continue reading
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 emotion … | Continue reading
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 produc … | Continue reading
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 p … | Continue reading
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 l … | Continue reading
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 impor … | Continue reading
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 … | Continue reading
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 build … | Continue reading
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 … | Continue reading
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 highli … | Continue reading
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 s … | Continue reading
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) – … | Continue reading
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 … | Continue reading
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 competito … | Continue reading
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 th … | Continue reading
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 Ki … | Continue reading
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 in … | Continue reading
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 ch … | Continue reading
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 cust … | Continue reading
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 qu … | Continue reading
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 … | Continue reading
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 … | Continue reading
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 fa … | Continue reading
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 discuss … | Continue reading
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 … | Continue reading
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. T … | Continue reading
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 … | Continue reading
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 … | Continue reading
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 fast … | Continue reading
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 ma … | Continue reading
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 c … | Continue reading
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, pa … | Continue reading
In episode 725, join Rob Walling and Ruben Gamez as they answer several more advanced listener questions. They discuss the challenges of pursuing freemium as a bootstrapper and make a suggestion that might surprise you. Rob and Ruben also talk about why building your business as … | Continue reading
In episode 724, join Rob Walling as he takes on some later-stage listener questions in another solo adventure. He provides several tips for managing managers, how to break through MRR plateaus, and how to think about SaaS versus agency work. Rob also offers his take on how he wou … | Continue reading
In episode 723, Rob Walling interviews Charles Duhigg, a Pulitzer Prize-winning journalist and bestselling author, about the significance of effective communication for founders. They discuss practical advice on recognizing different types of conversations, techniques for underst … | Continue reading
In episode 722, Rob Walling interviews James Mooring, co-founder of Astalty, a SaaS serving Australia's NDIS market. James reveals how they bootstrapped from zero to seven figures in just 18 months and then they explore the strategic decisions, clever pricing, and deep industry k … | Continue reading
In episode 721, Rob Walling and Asia Orangio analyze the results of MicroConf’s 2024 State of Independent SaaS Report. They share their key takeaways including the impact of business models on growth, requiring credit cards for free trials, and how the number of founders affects … | Continue reading
In episode 720, Rob Walling is joined by Craig Hewitt to discuss the intricacies of prioritization in both business and in life. In addition to running Castos, Craig has started coaching founders in sales and marketing, and describes how he strives to focus on the right things. T … | Continue reading