Startups For the Rest of Us

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.

Is your $500k app plateaued? Discover how to evaluate options like selling or diversifying. Learn why the autopilot mindset can lead to decline and what to consider for long-term motivation. Explore the risks of building MVPs for equity and the importance of clear agreements. Find out when it's essential to pursue SOC 2 compliance, and hear personal tips on balancing startup life with family. Plus, the value of open source versus traditional IP strategies for your business.

Is hiring a sales and marketing co-founder essential for technical SaaS founders? Rob discusses his "Core Four" skills: sales, marketing, product, and development, emphasizing their importance for early-stage teams. He shares experiences dealing with tricky enterprise clients and offers advice for managing numerous non-ideal customer profile signups. Additionally, a listener's inspiring startup exit story adds a personal touch to the conversation, highlighting the journey of entrepreneurship.

Philippe Lehoux, co-founder of Missive, a collaborative email tool, shares insights on bootstrapping the company to $8M ARR. He discusses finding early customers, emphasizing email-first positioning, and the importance of product quality for SMB loyalty. Philippe explains strategic content-driven growth, leveraging competitor momentum, and unique SEO tactics like in-depth alternatives pages. He also reveals why they chose not to pursue VC funding, favoring a sustainable growth approach while maintaining a diversified customer base.