Startups For the Rest of Us

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.

Dive into the intriguing debate of revenue versus profit in the SaaS world. Discover why waiting for permission can stifle innovation. Get inspired by Mike Tyson’s relentless work ethic and George Lucas's visionary creativity as you navigate obstacles. Learn the importance of understanding both income and expenses for true financial health. Remember, you don’t have to be the best to succeed; persistence and a unique vision can set you apart in your entrepreneurial journey.

Derrick Reimer, founder of SavvyCal and Drip, shares vibrant insights from MicroConf 2025 in New Orleans. He discusses the strong sense of community among 260 attendees and highlights impactful talks, including lessons on business exits and homepage positioning. Derrick explores innovative pricing strategies and emotional copywriting, emphasizing simplicity in communication. Excursions add a fun twist, fostering networking over culinary delights. The conversation wraps up with reflections on the event's evolving structure and the exciting future of MicroConf.

Dive into a thoughtful critique of controversial bootstrapping advice that challenges common startup beliefs. Discover why rebranding may not be worth your time and how affiliate marketing won't magically solve your growth problems. Learn about the importance of focusing on effective acquisition channels and the traps of unlimited feature plans. Hear insights on the reality of SaaS scaling, the necessity of specialization in hiring, and the valuable lessons from competitors’ reviews. Buckle up for a groundbreaking discussion!