Startups For the Rest of Us

Russ Walling, an entrepreneur who runs a California electrical contracting firm and blends construction, operations, and poker lessons. He talks mindset and resilience. Short takes on overcoming perfectionism, getting comfortable with discomfort, decision-making under uncertainty, the Armageddon beer story, and why hard work and collaborative leadership matter.

Jason Cohen, founder of WP Engine and SmartBear and author of Hidden Multipliers, shares sharp startup frameworks in plain language. He explains small, systematic changes that create outsized impact. He talks about writing to clarify ideas, niching to de-risk growth, winning against funded rivals through execution, and practical ways founders should approach AI today.

Have you ever pushed so hard on an idea that you missed the signal to change direction? In this solo episode, Rob Walling covers a wide range of topics and dives into three areas every founder should master: how to develop an editorial eye (or “taste”), the difference between persistence and obstinance, and why focus, not diversification remains the hardest, most valuable entrepreneurial skill. Episode Sponsor: Hiring engineers shouldn’t feel like sorting through AI-polished resumes. G2i cuts through all of that. They’ve pre-vetted over 8,000 engineers, all with 5+ years of real experience, and they run live, human-led technical interviews to verify actual skills. No time wasters. No guesswork. Just solid developers who can deliver. G2i is trusted by companies like Meta, Microsoft, and countless bootstrapped founders who need to move fast without making expensive mistakes. Get a 7-day free trial and $1,500 off when you mention Startups for the Rest of Us at https://www.g2i.co/rob Topics we cover:  (1:55) – How to develop an “editorial eye” (and why it matters for founders) (7:03) – When to get out of the way and let true experts lead (8:07) – Why your product must start with a real problem (not just an idea) (9:11) – Paul Graham’s The Right Kind of Stubborn: persistence vs. obstinance (12:03) – Are you attached to your goal or just your first idea? (13:44) – How great founders adapt to new data without losing momentum (14:44) – Sam Parr on why “constant switching will kill you” (16:30) – Focus as a founder’s hardest and most valuable skill (16:49) – Why “Triple, Triple, Double, Double” isn’t dead (despite VC takes) (18:34) – The problem with clickbait startup advice Links from the Show:  MicroConf Europe 2026 – Join us in Reykjavík, Iceland (Sept 21–23) - Promo Code: ROB50 The Mom Test by Rob Fitzpatrick Paul Graham: “The Right Kind of Stubborn” Sam Parr (@thesamparr) | X  Harry Stebbings (@HarryStebbings) | X Rob Walling YouTube Channel The SaaS Playbook 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

Discover how your everyday job can secretly shape your entrepreneurial journey. From figuring things out with unclear instructions to learning respect for others' time, everyday roles offer surprising lessons. Grit is taught through hard, unglamorous work, while experience often trumps credentials. The value of self-education and knowing when to cut corners are crucial skills. Plus, Rob shares insights on choosing the right team and mastering management, emphasizing that success starts with curiosity and ownership.

In this engaging discussion, Laura Roeder, founder of Paperbell and a pioneer in self-serve tools for coaches, shares insights on how her bootstrapped company triumphed over a $10M venture-funded rival. They explore why her competitor invested too heavily in engineering while neglecting marketing. Laura emphasizes the importance of focusing on the right customers and how limited paths for scaling impacted the competition. With clever strategies and efficient operations, Paperbell not only held its ground but emerged as the market leader.

The discussion dives into how AI, SEO, and market dynamics will shape SaaS in 2026. Key predictions include significant headwinds for horizontal SaaS and the risks of over-relying on SEO. It’s anticipated that brand dominance will increase due to AI-driven recommendations. There's also a forecast for a continued AI VC bubble and rising usage of open-source models. Notably, a major no-code platform might struggle, and acquisitions of small SaaS startups are expected to rise as big players seek growth.

Rob Walling dives into the growth of TinySeed, revealing insights from funding over 210 B2B SaaS companies. He discusses the rise of AI-first startups and the unique challenges they face. The conversation highlights why vertical SaaS is outperforming horizontal options and emphasizes the vital role of founder communities in overcoming isolation. Listeners will learn about emerging patterns in applicant trends and how mentorship shapes success in the startup ecosystem.

Ruben Gamez, founder of SignWell and a freemium expert, joins Rob Walling to explore the intricacies of SaaS growth. The duo discusses what a 'good' freemium retention rate looks like, revealing that mobile apps usually hover around 3-5%, while SaaS needs to exceed 20%. Ruben emphasizes that the shape of the retention curve is more important than raw numbers. They also delve into when founders should start delegating key roles, explaining the nuances of handing off responsibilities in sales, marketing, and product leadership.

In a lively discussion, Derrick Reimer, founder of SavvyCal, dives into the best AI coding stacks like Windsurf and Cursor, revealing how they enhance development workflows. He shares insights on balancing speed and polish as a solo founder and smartly utilizes reusable UI components. They explore how AI is shifting startup risks—from market fit to feasibility—and discuss practical security measures like rate limiting and IP bans. Derrick's expertise provides a fresh perspective on navigating the ever-evolving tech landscape.

Craig Hewitt, founder of Castos and creator of the '100 Days of AI' YouTube series, shares insights from his deep dive into AI tools for SaaS founders. He reveals surprising takeaways, ranks Claude Code above ChatGPT for developers, and discusses how Manus automates complex tasks. Craig explains the reality of AI agents cutting customer support load in half and his strategies for building new products beyond Castos, including exciting AI experiments. His candid thoughts on motivation and the risks of growth add an engaging layer to the conversation.