Startups For the Rest of Us

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 countle...

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 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 enterp...

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 even...

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...

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...

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...

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...

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 f...

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...

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. I...

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. Episod...

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 comp...

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 ca...

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 th...

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 a SaaS founder is usually the best way to build your brand indirectly. Episode Sponsor: Hiring senior developers can rea...

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 would talk about his product at conferences, without overselling it. Topics we cover:  3:48 – Three tips for managing other...

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 understanding and transitioning conversations, and how to quickly move past small talk in a conference setting. Episode Sponsor...

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 knowledge that propelled Astalty's remarkable growth, proving their success was far more than just a lucky break. Episode...

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 performance. Additionally, they delve into growth by target markets and the data behind bootstrapped SaaS companies taki...

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. They talk about buying back their time, creating family-focused time, and share their solo podcasting experience after pr...

In episode 719, join Rob Walling as he embarks on another solo adventure, tackling listener questions. He discusses how to test pricing, addresses the pitfalls of one-time payments vs. SaaS, and he reflects on “building something for everyone.” He wraps up with advice on making better recommendations. Episode Sponsor: We have been partnering with Lemon.io for several years, and they’ve proven to b...

In episode 718, Rob Walling and Derrick Reimer tackle listener questions about giving up on ideas, competing in crowded markets, and developing painful features. They also chat about SavvyCal’s recent design refresh, finding founder-market fit, and whether Derrick has retired from podcasting. Episode Sponsor: Is your outsourced development team dropping the ball? Maybe you’ve worked with a team th...

In episode 717, Rob Walling interviews Marie Martin, co-founder of Tally. They discuss the company’s journey to $1.3M ARR and the unusual pricing strategy that got them there. Marie details how they keep their support volume low, how they differentiate Tally from other form builders, and how they grew to over 300,000 free users. Episode Sponsor: We have been partnering with Lemon.io for several ye...

In episode 716, join Rob Walling for another solo adventure where he answers listener questions. He shares how he would position against incumbents, when to change an H1, and how choosing a tech stack affects your business valuation. Rob also weighs whether to skip a “Step 1” or “Step 2” business and start directly with a standalone SaaS in the Stair Step Method of Bootstrapping. Episode Sponsor:...