Startups For the Rest of Us

How can you scale yourself as a founder? In this episode, Rob Walling is joined by Yaniv Bernstein (co-founder and CTO of Vera , former COO, VP of Engineering, and Google leader) to unpack how a founder’s role must change as the company grows. From writing the code yourself to leading managers of managers, they dig into the tough transitions every founder faces, and what happens if you don’t adapt...

Welcome to Season 5 of TinySeed Tales, the documentary-style series where we follow one SaaS founder’s journey over 12 months to hear about the wins, the missteps, and everything in between. In this season premiere, Rob Walling introduces Harris Kenny of OutboundSync. After running a successful agency, Harris makes the leap to go all-in on SaaS. It’s a high-stakes transition that many agency owner...

What are the real risks of AI-generated code and “vibe coding”? In this episode, Rob Walling is joined once again by fan-favorite Derrick Reimer to answer a fresh batch of listener questions. They dig into solo vs. co-founder trade-offs, managing scope creep, and how integrations can shape early traction. Want to get your questions answered? Drop them here. Topics we cover:  (2:33) – Do you need a...

How do you know it’s time to move on from a product that’s growing? In this episode, Rob Walling chats with Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), about a rare founder journey: bootstrapping, catching lightning in a bottle, and choosing to go big with venture capital. They dive into the emotional and strategic weight of shutting down a $1.5M ARR product, what shifts when you sc...

How do you really know when you’ve hit product-market fit? In this episode, Rob Walling welcomes back Kevin Wagstaff, co-founder of Spectora, to answer listener questions about early traction in Facebook groups, finding product-market fit, handling criticism, and what it really took to bootstrap to a $90M exit. Want to get your questions answered? Drop them here. Topics we cover:  (3:15) – Early t...

How do you choose between multiple product ideas? In this solo episode, Rob Walling answers listener questions about picking between two SaaS ideas, product positioning, and how to know when to stop working on a project. Want to get your question answered? Drop them here. Topics we cover:  (3:06) – Choosing between two AI products (9:38) – Will early niche positioning hurt future growth? (14:51) –...

What’s the real roadmap to lasting financial freedom? In this episode, Rob Walling chats with Nick Maggiulli about his new book, The Wealth Ladder. Nick explains how to identify your current financial stage and what it really takes to move up. They dig into how wealth changes your spending habits, why exits (not salaries) drive significant changes in net worth, and how your definition of freedom m...

When is the right time to sell your profitable SaaS? In this week's episode, Rob Walling talks with Pierre de Wulf, co-founder of ScrapingBee, about how they mostly bootstrapped their web scraping SaaS to $5 million ARR and an eight-figure all-cash exit. They explore the pivotal shift that took them from $7K MRR to nearly $1M ARR in just 15 months, what Pierre splurged on post-exit, and the emotio...

Looking back on your entrepreneurship journey, which decisions made the biggest impact? In this solo episode, Rob Walling breaks down the 10 decisions that shaped his success, like choosing action over perfection, learning fast from failure, and building a financial cushion to take smarter risks. It’s an honest look at what worked and the choices that made the biggest difference. Topics we cover:...

Are you repeating any of these mistakes in your business?  In this episode, Rob Walling walks through his ‘founder regret list’, detailing 12 key mistakes from his 20-year entrepreneurial journey. In this very personal episode, he tells some stories he’s never shared publicly before. Topics we cover:  (4:17) – Thinking venture capital was the only path (6:12) – Launching without validating the ide...

What if your biggest growth blocker isn’t the market, but the story you’re telling yourself? In this episode, Rob Walling welcomes back fan favorite Ruben Gamez, founder of SignWell, to debunk common bootstrapper myths. They discuss misconceptions like never needing to sell your company or market your product, and emphasize the realities of growth plateaus, business valuation, and exit strategies....

Are common SaaS myths sabotaging your success? In this episode, Rob Walling sits down with SaaS growth expert (and TinySeed Institute coach) Marc Thomas to break down ten persistent and damaging myths believed by many SaaS founders and why challenging them is key to scaling smart. Topics we cover:  (4:52) – “I’m not good at marketing” is a lie (8:48) – Top-of-funnel obsession (13:12) – Lifetime af...

How do you price pilot projects and niche down without hedging your bets? In this episode, Rob Walling answers listener questions about pricing pilots, choosing niches, and skipping steps on his Stair Step Method of Bootstrapping.  Want to get your question answered? Drop them here. Topics we cover:  (3:25) – Feedback on Season 4 of TinySeed Tales (8:55) – How do you price pilot projects? (15:11)...

What if the traditional dream of retirement is actually a trap for entrepreneurs? In this episode, Rob Walling talks with Derek Coburn, author of Let’s Retire Retirement: How to Enjoy Life to the Fullest , to challenge the long-held belief that early retirement is the ultimate goal. They explore why many entrepreneurs feel unfulfilled after retiring and how shifting toward purpose-driven work can...

What’s it take to bootstrap a niche SaaS to $90M without raising a dime? In this episode, Kevin Wagstaff joins Rob Walling to share how he and his brother bootstrapped Spectora from a scrappy MVP to a $90M valuation. It’s a masterclass in finding traction in unsexy markets, building with empathy, and making smart bets like embedded payments. Topics we cover:  (4:39) – The surreal moment Kevin and...

What shortcuts are actually worth taking when you're building a SaaS? In this episode, Rob Walling and fan favorite Derrick Reimer delve into listener questions about startup development. They discuss the impact of AI coding tools on building minimum viable products (MVPs) and the importance of user experience (UX) with advice on balancing UX investment based on the product's nature.  You’ll also...

In this episode, Rob Walling sits down with Noah Tucker, the non-technical founder behind Social Snowball, an affiliate marketing SaaS built for Shopify. Noah bootstrapped the company to $5M+ in ARR, navigating technical roadblocks, team-building hurdles, and a crumbling codebase, while leveraging bold growth tactics like influencer partnerships to scale fast. Topics we cover:  (3:26) – Spotting t...

In this episode, Rob Walling and Maja Voje, author of Go to Market Strategist , dive into early customer profiles (ECPs) and why they matter more than ideal customer profiles (ICPs) early on. They explore practical, scrappy marketing tactics for B2B SaaS founders and share real-world advice on customer acquisition, community building, and staying authentic while growing. Episode Sponsor: This podc...

How do you position your SaaS for success? In episode 772, Rob Walling talks with Anthony Pierri of Fletch about a proven approach to product positioning. They discuss key lessons from 400+ startups, focusing on workflows, competitive alternatives, and why narrowing your audience matters. Topics we cover:  (6:59)  – What is positioning, really? (11:16)  – Why your homepage matters more than your p...

Can SaaS companies survive the rise of AI Agents? In episode 771, Rob Walling is joined by Craig Hewitt to answer listener questions. They discuss the changes that happen while transitioning from a small startup to a multi-million dollar SaaS, competing against larger competitors, and maintaining startup culture as teams grow. They also share thoughts on AI agents in the SaaS space and the relevan...

Is it more important for entrepreneurs to focus on revenue or profit? In episode 770, Rob Walling goes solo to explore the relationship between revenue and profit in SaaS, and the dangers of waiting for permission. He also draws inspiration from Mike Tyson’s work ethic and George Lucas’ visionary mindset to encourage entrepreneurs to push through obstacles and innovate. Topics we cover:  (2:41) –...

Did you miss out on MicroConf US in New Orleans? In episode 769, Rob Walling welcomes Derrick Reimer back to share highlights from MicroConf New Orleans. They dive into the event's vibrant atmosphere, standout founder talks, and the energizing mix of new and familiar faces that made this gathering in the Big Easy truly special. Topics we cover:  (1:40) – MicroConf New Orleans audience breakdown (5...

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 rebranding your SaaS, the hidden problem of affiliate marketing, and the realities of scaling a SaaS business. Topics we cover...

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 against competitors. They also weigh in on how product managers should focus their time. Topics we cover:  (2:50) – Is your...

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 importance of emotional resilience in entrepreneurship. They also dive into Close's recent pricing shift to introduce a...