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

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: https://youtu.be/GGFYCT9m7hU- Spotify: TODO- Apple Podcasts: TODO🗒️ Show Notes- Stop Writing Documents Nobody Reads: https://tech.loveholidays.com/stop-writing-documents-nobody-reads-68842f59f28c- Paul Ingles — LinkedIn posts: https://www.linkedin.com/in/pingles/recent-activity/all/- Elixir's With Statement: https://www.openmymind.net/Elixirs-With-Statement/- The Comprehensive Guide to Elixir's for Comprehension: https://www.mitchellhanberg.com/the-comprehensive-guide-to-elixirs-for-comprehension/- Why LLM-Powered Programming is More Mech Suit Than Artificial Human: https://matthewsinclair.com/blog/0178-why-llm-powered-programming-is-more-mech-suit-than-artificial-human- matthewsinclair/intent on GitHub: https://github.com/matthewsinclair/intent- What We Let Machines Do: https://matthewsinclair.com/blog/0186-what-we-let-machines-do- When Thinking Isn't Just Fast or Slow Anymore — The Rise of System 3: https://www.incrementone.com/perspectives/when-thinking-isnt-just-fast-or-slow-anymore-the-rise-of-system-3- 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-aphantasia🗣️ GuestLes Cochrane: https://www.linkedin.com/in/lescochrane/🎙 Hosts- Matt: https://matthewsinclair.com- James: https://www.linkedin.com/in/james-wilson-92170656🌐 More from us- What Next?: https://whatnext.dev/- Matthew Sinclair: https://matthewsinclair.com/- Quantum Fax Machine: https://quantumfaxmachine.com/🎬

From KC-10 refuellers to centaur coding with Peter Marreck

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 Peter Marreck, who's currently consulting on AI for legal workflows. Peter's route in was not the standard one. Four years in the US Air Force as an electrical specialist on a KC-10 refueller (actively trying to avoid anything to do with computers, it didn't take), then Cornell, then web software since 2000: FactSet, Deloitte, ThredUp, Desk, a decade running his own contracting shop, then Director of Engineering at Adgenes. The Commodore Pet got him at age eight and he's been spitting ever since.In this episode, we cover:- Why he wanted to be a doctor until he touched a Commodore Pet, and why being into computers in the 80s was "social suicide"- Trust your gut, including the time someone told him not to buy Apple stock- The centaur coder: five months of collaborating with an LLM and what changed in how he thinks about design- The thin coordinator pattern: a pure Zig functional core wrapped in a CFFI so any front end can hang off it- Why LLMs are unusually good at Zig (similar to C, simple enough to grok)- Pushback on Dario Amodei: the people who'll survive are the ones who grab the surfboard, not the ones who get washed out- Dunning-Kruger as a service, and what to make of Gary Tan's G-Stack prompts- "Don't fire your engineers. Attack the backlog instead." Why this is the moment for the work that's been sitting around for two years- Cognitive surrender as a third category of thinking, and the cost of handing too much off to the model- "Idiocracy is a documentary from the future." Peter on the incompetence failure mode being scarier than the malicious one Guest:Peter Marreckhttps://www.linkedin.com/in/petermarreck/ HostsMatt: https://matthewsinclair.com James: linkedin.com/in/james-wilson-92170656More from us:https://whatnext.dev/https://quantumfaxmachine.com/

If you bend it, you have to mend it: Ben Moag on tanks, trading floors, and the AI quality cliff

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 Ben Moog, Head of Engineering at InsurX. Ben's path is not the usual one. Computer science at Bristol, then Sandhurst and a stint as a tank commander in the British cavalry, then a decade in finance (central risk trading at Citi, quant portfolio management at a hedge fund), then the standard quant PM ending of burnout and a divorce, and now his sixth greenfield build, this time rebuilding the Insurex platform live while the business is still running on it.In this episode, we cover:- Ben's "if you bend it, you have to mend it" philosophy and why a chaotic childhood is good career preparation- Why a quant trading floor is more stressful than commanding a tank- The Citigroup coffee story and what high-trust teams actually look like- Managers care about outcomes, leaders care about repeatable outcomes- Why Ben lets his team veto his hires before he ever sees a CV- The AI quality cliff in March and April, what's causing it, and what to do about it- "Only ask AI a question you know the answer to" and other rules for surviving agentic coding- Advice for engineers a year or two into their career, and why this is the most exciting time to be building tech since the 80s🗒️ Show Notes"Everyone Lies to Leaders" (2021 article Matt referenced): http://rubick.com/everyone-lies-to-le... [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa01JUDhrWTluN2ZlNzYwWFY4YmViVDhXdldjd3xBQ3Jtc0tudXNTMHZYdjF3c240MzFhOWdYdGxYcUowMlp3cHV1bERhWXh6SjZGeHNDb0VRTFJSS1NyYUdjZW0xazFGOFNmMFNNU1pYWkxGclRKYkNBUk1QU3pEQ2dJOXVCMWVZUnY0UEdTTUlDQm9ucmxOQXFVWQ&q=http%3A%2F%2Frubick.com%2Feveryone-lies-to-leaders%2F&v=z_4tv4Ezve0]🗣️ GuestBen Moog — Head of Engineering, InsurXLinkedIn: linkedin.com/in/benmoag/ [linkedin.com/in/benmoag/]🎙 HostsMatt: https://matthewsinclair.com [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbTNBbENPY2F1LW9EVE1BX21OSnZrYmFtMl9ud3xBQ3Jtc0tuSk83ajkzaFlONlNJV0FqXzdtQXYtV3IwN3NsUGVaSmNOVHBlYmdCbUJnYklJYkFsWmxqdWhYR1FwMkgyYkg0Y3NiZkhMR3h4endld2hxLUxsMFhmdXBtYmt6T29xcXdjRjR5Y3I5ajFTaUNtMGlvVQ&q=https%3A%2F%2Fmatthewsinclair.com%2F&v=z_4tv4Ezve0]Matt: linkedin.com/in/matthewsinclair [linkedin.com/in/matthewsinclair]James:   / james-wilson-92170656   [https://www.linkedin.com/in/james-wilson-92170656/]🌐 More from us:https://whatnext.dev/ [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbEpDeGM2WHExRVVDOGkyVnkyemZjSXpEc1dRd3xBQ3Jtc0ttdGZUN3VmYmg3NkozY3l2X0xRWFZXLTRRbmFwRERrc1VNMUl1Q3R4WnpUQ1F0QWdTMzBPY19rU256UWhOX2FoQ0F0VTJvek1wSEJTaWNWQzBtdTh5bHB5c1pVNVZtcWotYmdLR2psVkIwMVVSN0xRTQ&q=https%3A%2F%2Fwhatnext.dev%2F&v=z_4tv4Ezve0]https://quantumfaxmachine.com/ [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa3pfbkxId3huWU9NV1dERGg3aXpOVlA2V3Rkd3xBQ3Jtc0ttTFUxaWRsSjYwUk8wcGhlUEhlY0pINXJDeHJ2TUs1R20tRlZXTElvdk9KN1RaOTlXdHFvNEpodkF1MVRmaS1kNFZETndMR0N5Q0ItMUZWeXp0MW1oemtEeEMtdmpOTHR6OHlmdVVUNzBLNWhOVjQ0cw&q=https%3A%2F%2Fquantumfaxmachine.com%2F&v=z_4tv4Ezve0]

From the Joburg Stock Exchange to CTO of Zilch: Sean Hederman on why being right doesn't scale

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 Sean Hederman, CTO of Zilch, one of the UK's biggest fintechs. Sean was the second hire at Zilch. Before that he built bi-temporal reference data systems at the Johannesburg Stock Exchange, transformed DevOps at Stanlib and Direct Line, and somewhere along the way worked out that being the best individual engineer in the room is a ceiling, not a career. In this episode, we cover: -Why "being right doesn't scale" and what to engineer instead -The multiplier effect: lifting a team by 20% beats doubling your own output -Conway's law and the reverse Conway manoeuvre at Zilch -Queuing theory applied to engineering teams (and why Sean mandates 20 to 30% tech debt work) -Humans as chaos monkeys, and why half of software engineering practice exists because we're unreliable -Hiring engineers in the agentic era and the AI usage patterns Sean actually looks for -Adversarial agentic coding, spec-driven development, and getting the model to review its own work -The myth of the 10x programmer and what real force multipliers look like on a team Guest: Sean Hederman https://www.linkedin.com/in/sean-hederman/ 🎙 Hosts Matt: https://matthewsinclair.com James: linkedin.com/in/james-wilson-92170656 🌐 More from us: https://whatnext.dev/ https://quantumfaxmachine.com/

From DevOps to Novels: Richard Bown on Engineering with Empathy

This week on I'm a Software Engineer ~ What Next? James and Matt are joined by Richard Bown, DevOps engineer and author of Human Software, a novel that captures the messy, human side of engineering work.We get into:Richard’s winding journey from IC to manager and back again — and why that detour made him a better engineerWhy burnout, bad management, and “culture fit” aren’t bugs — they’re design flawsHow writing a novel helped Richard reflect on decades in tech — and why fiction can be a powerful tool for changeYou might enoy this if:-You're a senior engineer debating the jump to management-You’ve felt stuck in your tech career and wondered: is this it?-You’re curious how AI, team structure, and empathy are reshaping how we build software🎧 Listen now on Spotify | iTunes | YouTube📘 Check out Richard’s book: Human Software [https://richardwbown.com/human-software/]