Show Notes
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.
Chapters 00:00 Introduction to Start-up Advising 02:09 The Day-to-Day of a Start-up Advisor 05:39 Hiring Challenges in Start-ups 07:39 Defining the Role of a CTO 10:36 Common Mistakes in CTO Hiring 12:59 Bridging the Gap: Technical and Business Communication 16:40 Utilizing Client Feedback for Product Improvement 20:06 Transitioning from Proof of Concept to Product 24:01 Exploring Computer Vision in AI 24:06 Balancing Technical Excellence and Business Focus 24:09 Exploring Related Content
Alex's Links: Alex's LinkedIn: https://www.linkedin.com/in/alexander-berkovich-startup-advisor/
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 A CTO's value is in leadership and strategy, not just how much they can code.AI has fundamentally changed the hiring process and what makes a good candidate. Document every corner you cut in a POC — it will catch up with you later. Engineers should seek direct client feedback to understand the real impact of their work. Communication is the most underrated skill in any startup team. A POC and a product are very different things — don't let one accidentally become the other. Startups offer breadth of experience that large enterprises simply can't match. Hiring for the right mindset matters more than hiring for pure technical skill. Small technical decisions can ripple out and affect cost, timelines, and the whole product. The best teams stay connected to the end goal, not just the task in front of them.
More from Coding Chats
Coding Chats Episode 83 - In this episode, VB from OpenAI’s developer experience team explains why he thinks plan mode is obsolete and how coding agents have shifted from step-by-step instructions to outcome-driven, long-running work. We cover how to write a good agents.md, why tests still matter when agents write the code, spec-driven development, and why cloud agents may be the future of dev tooling.
Coding Chats Episode 82 - John talks with Dave Westgarth, head of delivery at a Databricks consultancy. Dave shares his path from a psychology degree and McDonald's into tech, and they discuss why the Scrum Master role is so misunderstood, how it differs from a delivery manager, and whether either needs to be technical.They also look at how AI is changing delivery work. Faster code just moves the bottleneck upstream, John argues there's no AI-specific skill you can't learn in a day, and engineering fundamentals are what make AI useful.
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 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.
Coding Chats Episode 78 - John Crickett talks to Robert Harris, an experienced engineering leader. Robert shares hard-won lessons from years of leading software teams, drawing on a distinctive "human systems" lens to explain why so many engineering organisations struggle — not because of bad people, but because of broken systems, misaligned leadership, and invisible cultural forces.