Show Notes
Coding Chats episode 36 - Rob Morgan shares his journey from being a traditional software developer to becoming a successful freelancer and eventually launching his own SaaS product. He discusses the importance of client interaction, the challenges of freelancing, and how he identified a niche market in the window cleaning industry. Rob emphasizes the significance of networking, understanding user needs, and the iterative process of product development. He also provides valuable insights for aspiring freelancers and entrepreneurs, including tips on pricing and customer engagement. In this conversation, Rob shares his entrepreneurial journey, reflecting on the successes and challenges of his first SaaS business, Cleaner Planner, and the lessons learned from its eventual sale. He discusses the importance of timing, customer engagement, and the pull demand in business success. Rob also delves into his transition to a fractional CTO role after selling his second venture, highlighting the challenges of rebuilding a software product and the need for effective marketing strategies. Additionally, he expresses his interest in starting a podcast focused on the journeys of SaaS founders, aiming to create a community for early-stage entrepreneurs.
Chapters 00:00 The Journey to Freelancing 05:40 The Transition to Freelance Work 12:40 Navigating the Freelance Landscape 20:00 Challenges of Freelancing 26:46 The Shift from Freelancing to Startups 30:30 Finding the Right Startup Idea 38:12 Building a Community Around a Niche Problem 51:23 Navigating the Challenges of Growth and Exit 57:42 Reviving Skills and Embracing New Technologies 59:30 The Journey of Rebuilding Software 01:02:26 Understanding Customer Needs and Market Dynamics 01:05:22 Navigating Marketing Challenges 01:06:55 Transitioning to a Fractional CTO Role 01:10:12 Exploring Future Opportunities and Podcasting 01:13:17 Building a Community for Founders
Rob's Links: https://trialtopaid.iohttps://linkedin.com/in/rbdmorgan/
John's Links: John's LinkedIn: https://www.linkedin.com/in/johncrickett/ John’s YouTube: https://www.youtube.com/@johncrickett John's Twitter: https://x.com/johncrickett John's Bluesky: https://bsky.app/profile/johncrickett.bsky.social
Check out John's software engineering related newsletters: Coding Challenges: https://codingchallenges.substack.com/ which shares real-world project ideas that you can use to level up your coding skills. Developing Skills: https://read.developingskills.fyi/ covering everything from system design to soft skills, helping them progress their career from junior to staff+ or for those that want onto a management track.
Takeaways Rob transitioned to freelancing after feeling stifled in traditional roles. He values client interaction for understanding user needs. Freelancing can be a rollercoaster of feast and famine. Rob's first freelance project came from a connection in affiliate marketing. Sales for Rob is about consultative problem-solving, not traditional selling. Freelancers should network to find clients and opportunities. Rob's SaaS idea emerged from identifying a niche problem in the window cleaning industry. Engaging potential customers early can validate a product idea. Pricing should reflect the value provided and be competitive. Rob reflects on his first business success and the lessons learned. The importance of timing and recognizing opportunities in business. Customer engagement and understanding needs are crucial for success. Rob's experience with the challenges of marketing a new product. The significance of having a pull demand rather than push in business. Rob discusses the natural end of his first business and the decision to sell. The transition from being a business owner to a fractional CTO role. Rob's insights on rebuilding a software product and the challenges faced. Rob's plans for a podcast focused on the journey of SaaS founders.
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Coding Chats Episode 81 - Ben Howdle talks to John Crickett about being a first time CTO in a start-up. Ben, author of The First CTO, shares what changes when you move from building technology to leading a technical team: the pressure, the trade-offs, and the realization that writing code is only part of the job.Drawing on startup experience and lessons learned the hard way, Ben discusses how to balance quality against runway, manage people, and communicate technical decisions in terms that founders and other non-technical stakeholders can understand. He also explores why resourcefulness, resilience, and comfort with ambiguity matter so much—and why CTOs often spend more time selling ideas than they expect.Whether you’re stepping into your first CTO role or leading a technical team at an early-stage company, this conversation offers candid insights into the realities of technical leadership.
Coding Chats Episode 80 - start-up advisor Alexander Berkovich shares his expertise on building successful start-ups, hiring strategies, CTO roles, and the importance of communication between technical and business teams. Discover practical tips for navigating the challenges of early-stage companies and how to align technical excellence with business goals.
Coding Chats Episode 79 - Richmond Alake, Director of AI Developer Experience at Oracle, joins John to discuss agent memory — how AI agents store, retrieve, and adapt to information. He argues that developers building memory on flat files are naively reinventing the database, and that once you factor in concurrency, security, and scalability, a proper database is inevitable. The conversation covers the full memory stack and how Oracle's AI database keeps embeddings and data together without shipping sensitive information to external providers.