Startups For the Rest of Us

Ruben Gamez, founder of SignWell and BidSketch, brings over 16 years of SaaS expertise to the table. He challenges common myths that entrepreneurs hold, such as the idea of never selling their business or that marketing isn’t necessary. The conversation highlights how these misconceptions can stifle growth and lead to stagnation. Gamez emphasizes the importance of understanding growth plateaus, needing to innovate marketing strategies, and balancing hard work with the reality of luck in entrepreneurship.

In this insightful discussion, SaaS growth expert Marc Thomas, a coach at TinySeed Institute, challenges ten common myths that many SaaS founders hold. He debunks the belief that marketing skills are unattainable and emphasizes the pitfalls of obsessing over top-of-funnel strategies. Marc warns against hiring marketing teams too early and the dangers of chasing new markets without solid foundations. He also advocates for a more integrated sales approach and addresses fears that can stifle growth, such as sending more emails or pursuing shiny distractions.

Discover the art of pricing pilot projects and how to establish fair value exchanges with clients. Dive into the nuances of niching down in the SaaS world while navigating calculated risks. Explore the secret ingredients to crafting a hit open-source tool and whether you can truly skip steps in building a SaaS business. This discussion highlights the emotional rollercoaster of entrepreneurship and emphasizes the importance of community support among startup founders.

Derek Coburn, a financial advisor and author of "Let’s Retire Retirement," introduces an intriguing perspective on the retirement myth. He argues that traditional retirement often leads to boredom and dissatisfaction, suggesting that purposeful work can instead enhance freedom and fulfillment. The conversation highlights the importance of health, relationships, and the concept of 'unretirement'—engaging in meaningful activities throughout life. Coburn also discusses how extending one's work life can improve financial stability, while encouraging enjoyment and self-care.

Kevin Wagstaff, co-founder of Spectora, reveals how he and his brother turned a humble home inspection software into a $90M powerhouse without outside funding. They discuss the surreal moment they became multimillionaires and the strategy of focusing on a mobile-first approach in an overlooked market. Kevin shares how embedding payments created a lucrative second revenue stream and the hustle that got them there—think early morning demos and trade shows. He also highlights the power of community in navigating challenges and building credibility.

Derrick Reimer, Founder of SavvyCal and expert in user experience, shares insights on startup development. He discusses the impact of AI coding tools on building MVPs while emphasizing the importance of user-centric design. The conversation delves into the costs of leaving the cloud versus on-prem solutions, alongside tips for better email deliverability. Derrick also stresses the importance of validating ideas through user feedback, underlining that understanding customer needs remains crucial, no matter how fast you move.

Noah Tucker, the founder of Social Snowball, shares his inspiring journey as a non-technical entrepreneur who bootstrapped his affiliate marketing SaaS to over $5 million in ARR. He discusses spotting a gap in the affiliate tools market, facing challenges like early development misfires and losing a CTO to priesthood. Noah attributes his rapid growth to strategic influencer partnerships and the importance of hiring a stellar engineering team, highlighting the resilience and adaptability required in the entrepreneurial landscape.

Maja Voje, an expert in go-to-market strategies for B2B SaaS, shares her insights on identifying early customer profiles (ECPs) and why they can be more vital than ideal customer profiles at the start. She discusses scrappy marketing tactics for effective customer acquisition and the significance of authenticity in community building. Maja provides practical advice on overcoming common pitfalls and adapting strategies based on real-world feedback, making it clear how important early engagement is for startup success.

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 pitch deck (14:17) – Workflow-based segmentation vs. firmographics (17:39) – Positioning against competitive alternatives (31:13) – The #1 mistake founders make with positioning Links from the Show: MicroConf Growth Retreat | London, UK - May 14-16, 2025 Invest in TinySeed Get Access to Anthony’s MicroConf New Orleans Talk Anthony Pierri (@anthonypierri) | LinkedIn Anthony Pierri (@apierriPMM) | X Fletch If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

Craig Hewitt, founder of Castos, shares his experiences in scaling a SaaS company while maintaining culture and brand identity. He discusses the challenges of transitioning from a startup to a multi-million dollar business and the survival of SaaS amid AI agents. The conversation dives into the impact of AI on SaaS platforms and the complex nature of patents for bootstrapped firms. Hewitt emphasizes the importance of community engagement and strategic hiring to sustain values during growth, providing invaluable insights for tech entrepreneurs.