From IT support to co-founding BorrowMyDoggy: Les Cochrane on his road to becoming a CTO

Welcome back to I'm a Software Engineer ~ What Next? The podcast for devs figuring out their next move. Hosted by James Wilson and Matt Sinclair, we talk honestly about what it takes to build a meaningful career in tech. This week we're joined by Les Cochrane, CTO at Practice Toolkit, building software for GPs inside the NHS. Les started in hardware, networks and second-line IT support, switched to interactive media at uni, did UX before anyone called it UX, taught himself the backend on a Rails app he built to replace the FTP site at a marketing agency, and then co-founded BorrowMyDoggy on the back of a weekend hackathon. After that: contracting, leading 24 engineers in sports data at IMG Arena, including being the employee rep when they had to let go of about 180 of them, and now CTO at a healthcare startup learning what compliance means for the first time. In this episode, we cover: Validating his startup that he co-founded, BorrowMyDoggy, by sticking posters up on Hampstead Heath and having someone in Exeter sign up within 24 hours What happens when 4,500 people sign up in an hour to a landing page that doesn't have a working search yet Why "I need help" is the wrong way to ask for help, and what to say instead Product engineer vs T-shaped vs Kent Beck's paint-drip people, and why time matters in the metaphor Going from leading 24 engineers to being the employee rep during a 180-person redundancy AI as a force multiplier "for good or evil" — and why introducing it into a six-month-release shop won't help The LLM-generated PR quiz that makes you answer 10 questions about your own checked-in code before it merges Centaur chess, supertanker captains, and Kahneman's type-3 thinking: cognitive offload and what we lose 🔗 Links YouTube:    • Video   Spotify: TODO Apple Podcasts: TODO 🗒️ Show Notes Stop Writing Documents Nobody Reads: https://tech.loveholidays.com/stop-wr... Paul Ingles CTO uSwith — LinkedIn posts:   / all   Elixir's With Statement: https://www.openmymind.net/Elixirs-Wi... The Comprehensive Guide to Elixir's for Comprehension: https://www.mitchellhanberg.com/the-c... Why LLM-Powered Programming is More Mech Suit Than Artificial Human: https://matthewsinclair.com/blog/0178... matthewsinclair/intent on GitHub: https://github.com/matthewsinclair/in... What We Let Machines Do: https://matthewsinclair.com/blog/0186... When Thinking Isn't Just Fast or Slow Anymore — The Rise of System 3: https://www.incrementone.com/perspect... From Engineering Bootcamps & Founding Startups to GitHub with Kate Catlin: https://whatnext.dev/episodes/s01/e18 Aphantasia — When You Can't Picture Things in Your Mind: https://aphantasia.com/what-is-aphant... 🗣️ Guest Les Cochrane:   / lescochrane   🎙 Hosts Matt: https://matthewsinclair.com James:   / james-wilson-92170656   🌐 More from us What Next?: https://whatnext.dev/ Matthew Sinclair: https://matthewsinclair.com/ Quantum Fax Machine: https://quantumfaxmachine.com/ 🎬