Technically Speaking with Harrison Wheeler

Harrison Wheeler
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Conversations for design managers and aspiring leaders, delivering real stories and ready to use tactics to help you build confidence and credibility. I sit down with top voices in design, tech, and business to open the black box of leadership. I'm your host, Harrison Wheeler, with 20 years in design and a decade leading teams from scrappy startups to global giants. It's time to get technical. technicallyspeakinghw.substack.com

  1. Green flags over red flags: Navigating today's brutal job market with Jermaine 'The Jobfather' Murray

    12/08/2025

    Green flags over red flags: Navigating today's brutal job market with Jermaine 'The Jobfather' Murray

    Back in spring 2024, I recorded a handful of episodes with no idea they’d take the scenic route to your inbox. Life had other plans, but the conversations held up beautifully, maybe even better with a little time to breathe. This is the first in a short run of those spring episodes, and I think you’ll find it worth the wait. In this episode of Technically Speaking, I'm joined by Jermaine Murray also known as The Jobfather. He's a career coach and founder of Jupiter HR, who's vision is to help 500 Black professionals land jobs in tech (he’s currently at 448). We get into the state of today's job market from employer indifference toward DEI to the rise of AI, and what it actually takes to future-proof your career. Jermaine shares his approach to identifying green flags when evaluating companies, how to avoid burnout while doing meaningful work, and why now is the time to invest in yourself even when the odds feel stacked against many. This one's part motivation, part strategy, and packed with sharp insights for anyone navigating change. We also had a few moments of laugh out loud laughter from his stories. Key Takeaways * Leverage Your Past Skills: Don't abandon previous experience when transitioning to tech - assess what you're good at, what you like, and what you've had success with to find the right tech role * Job Market Reality Check: Current tech job searches take 9-18 months (vs. 2-3 months previously) due to increased competition and fewer opportunities - timing and referrals are crucial * DEI Shift: Companies have moved from active diversity requirements to "indifference" - focus on finding places where you're appreciated, not just tolerated * Embrace AI as a Tool: You won't be replaced by AI, but by someone leveraging AI better than you - adapt and use it as a productivity multiplier rather than fear it * Ask the Hard Questions: Always interview to know your market value, and directly ask about things that make you anxious (company stability, layoff history, diversity support) - how they respond matters more than what they say Notable Quotes "Ask them the most awkward things. The things that make you feel anxious. Ask them... what happens with disruptions or new technologies." "Taking an interview is not the same as job hopping... you should always be interviewing so that you know what your real time value is and whatever decision that you make is an informed decision." "You can't be scared of AI... you will be replaced by somebody that is leveraging AI rather than AI itself." "Why do you think that your employer owns the skills that you carry with you in your body? They own the time that you work for them, but all the skills you carry with you." Resources * Follow Jermaine on LinkedIn, Twitter, Instagram, TikTok * JupiterHR * Harrison on LinkedIn, Instagram Timestamps 00:00 Introduction 00:30 Meet Jermaine Murray "The job father" 00:47 Jermaine's mission and success stories 02:05 Balancing work and health 03:01 Gaming talk: from Final Fantasy to Nvidia 04:30 Current obsessions: fitness journey 07:41 Unusual jobs and memorable stories 11:59 The origin of 'The job father' 17:54 Defining tech and career advice 24:29 Understanding career motivations 25:10 Leveraging past skills in new roles 27:35 Recruitment strategies and market trends 30:51 The impact of DEI in the workplace 35:02 Navigating AI and technological advancements 40:18 Identifying green flags in job opportunities 47:25 Final thoughts and contact information Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

    50 min

  2. 05/05/2025 · BONUS

    Human-centered AI: Ovetta Sampson on design risks and rewards

    This episode of AI Product Builders is a must-listen. I’m joined by Ovetta Sampson, founder of Right AI and one of the sharpest minds in the AI and design space. With a career that spans leadership roles at Google, Capital One, and IDEO, Ovetta brings a powerful, context-driven lens to the hype around generative AI. We get into: * Why she left Google to build Right AI * The risks no one’s talking about in AI product development * What MoviePass, the Black Death, and Silicon Valley have in common * The real environmental and economic costs of running LLMs * What design leaders need to unlearn now * Her “Mindful AI” framework for building responsible, people-first experiences * Why systems thinking beats wireframes, and what it really takes to design for the future Ovetta breaks it all the way down, history, economics, tech, and the human cost of innovation. This one’s part philosophy lesson, part design critique, part wake-up call. Timestamps 02:09 Origins of Ovetta's company Right AI 05:15 Moving fast and breaking things...again 10:20 The risks of funding with no business models 18:56 Enviornmental sustainability 30:18 Principles of building a responsible experience 34:01 What's top of mind for design leaders? 43:24 Closing Mentions * Right AI * LinkedIn - Follow her on LinkedIn for hot takes and sharp truths * The Philosopher’s Zone (Podcast) – She references a philosophy podcast about the Dark Ages * Gutenberg & the Printing Press – Used as a metaphor for today’s AI hype * MoviePass – Referenced extensively as an analogy for unsustainable business models * Black Death / Plague – Referenced in historical parallel to today's societal reset Follow Harrison Wheeler and Technically Speaking * Newsletter * LinkedIn * YouTube Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Are you looking to level up your design leadership and management craft? Spend an hour with me for personalized 1:1 coaching to help you thrive in your role. Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

    44 min

  3. 05/05/2025

    Vibe coding: A beginner's guide with Kyle Zantos

    I’m joined by the imaginative Kyle Zantos, a Seattle-based designer, builder, and musician with over a decade of experience across UX, product, and brand. Kyle’s worked at startups and consultancies, but lately he’s been diving into AI through deeply personal, playful projects that blend creativity, tooling, and experimentation. We get into: * Why he shifted from music to design, and now from design to building AI tools * How he used AI to build a Figma plugin without any coding background * The tools in his AI stack and how he actually uses them (Claude, Cursor, Lovable, Vercel, and more) * What MCPs are and how they help Claude "remember" his context across chats * Why rapid prototyping now beats hours in Figma * His framework of “Software as a Gift,” building custom apps just for friends * A look at the Jeopardy-inspired app he built for his trivia-loving best friend Kyle brings curiosity, technical scrappiness, and real heart to everything he builds. Whether you’re a designer figuring out how to start with AI or just looking to rekindle some joy in your craft, this one’s for you. Timestamps 00:00 Introduction 02:07 Kyle's musical interests and background 06:41 Kyle's journey into "vibe coding" 13:02 From an early course to building som ething functional 20:59 Leveraging MCPs to build smarter 26:26 Software as a gift 36:49 Where AI has influenced Kyle's design process 38:59 How can design org incentivize to close the skills gap 41:29 How to get started with AI 43:15 Closing Follow Kyle * Website: https://kylezantos.com * Twitter: https://twitter.com/kylezantos * LinkedIn:https://www.linkedin.com/in/kylezantos Mentions * Jeopardy practice game — Kyle launched (in time for this release) * Claude (by Anthropic) — AI assistant used throughout Kyle's workflow * Cursor — AI-first code editor forked from VS Code * Lovable — No-code AI app builder Kyle uses for software-as-gift experiments * Vercel — Deployment platform for full-stack apps * SuperWhisper — Voice-to-text transcription tool * Ammaar Reshi — Design leader at DeepMind; inspired Kyle's early AI builds Follow Harrison Wheeler and Technically Speaking * Newsletter * LinkedIn * YouTube Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Are you looking to level up your design leadership and management craft? Spend an hour with me for personalized 1:1 coaching to help you thrive in your role. Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

    45 min

  4. 05/05/2025

    Inside the creative process: Jay Demetillo leads Canva’s bold leap beyond traditional spreadsheets

    In this episode of AI Product Builders, I sit down with Jay Demetillo, design lead at Canva, to talk about what it means to design spreadsheet experiences for the future. Jay has worked all over the world—from Grab in Southeast Asia to leading the design of AI features inside Canva Sheets. Now based in Australia, he shares what it took to reimagine a legacy product, modernize complex workflows, and bring AI in as a meaningful co-pilot, not just a gimmick. We get into: * The drag-and-drop design challenge no existing tool could solve and how he had to rely on his ingenuity * Prototyping high-fidelity interactions with ProtoPie to shape engineering scoping * Why working across time zones requires clarity, collaboration, and great prototypes * How Canva Sheets makes data visualization, formulas, and mobile editing easier for everyday users * The principles behind Canva’s “magic” AI features like Magic Insights and Magic Formulas * Jay’s own side project: an article tracker app built with AI * What working with AI taught him about the limits of solo building This episode isn’t about slapping AI on a product. It’s about thoughtful design, real teamwork, and pushing past the hype to deliver something users actually need. Mentions * Canva Sheets: Jay’s current product focus * ProtoPie: Interactive prototyping tool used for high-fidelity handoff * Claude: Used for early AI prototyping * Cursor: IDE for building with AI * Jay Demetillo on LinkedIn: Follow his updates and perspectives Follow Harrison Wheeler and Technically Speaking * Newsletter * LinkedIn * YouTube Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Are you looking to level up your design leadership and management craft? Spend an hour with me for personalized 1:1 coaching to help you thrive in your role. Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

    41 min

  5. 05/05/2025

    Breaking up with mockups: Filip Skrzesinski on Subframe's real-time design with code

    In this episode of Technically Speaking: AI Builders, I sit down with Filip Skrzesinski, co-founder of Subframe, the UI design tool built for the AI era. Subframe isn’t just another no-code platform or AI playground. It’s a visual way to build production-ready software, allowing designers and non-technical teammates to collaborate directly with engineers using code-native components, real-time prototyping, and AI-assisted workflows. Filip calls it “design with code.” We unpack what it really means to bridge the gap between design and development, the philosophical shift away from static mockups, and how Subframe puts creative control back into the hands of full product teams. We also get into: * Why designers should think more like engineers (and vice versa) * How AI becomes a co-creator, not a replacement * What makes a good design system “trainable” for AI * Why stress-testing components in Subframe feels like building your own mini design tool * What it looks like when prototyping and production merge If you’re a designer, builder, or curious product leader navigating the messy middle of AI and UI, this episode offers practical insights, creative inspiration, and a glimpse into the future of design tools. Learn more at subframe.com Timestamps 00:00 Filip Skrzesinski x Harrison Wheeler: AI Product Builders Series 00:25 Introduction 02:56 Where Subframe sits in the product development process 06:02 The origin story 10:39 The ideal customer profile 21:13 What makes Subframe stand out? 27:11 Where a designers job starts 30:15 Examples of how people are using the platform 34:51 How to get started within minutes 37:26 How organizations can embrace 40:18 Closing and whats next Mentions * Subframe.com — Official website * Filip Skrzesinski on LinkedIn Follow Harrison Wheeler and Technically Speaking * Newsletter * LinkedIn * YouTube Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Are you looking to level up your design leadership and management craft? Spend an hour with me for personalized 1:1 coaching to help you thrive in your role. Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

    42 min

  6. 05/05/2025

    Pablo Stanley on developing Lummi.ai and achieving product-market fit

    In this episode of AI Product Builders, I sit down with designer, illustrator, and founder of Lummi AI, Pablo Stanley. From launching open-source illustration libraries to experimenting with AI-powered image generation, Pablo has always been pushing the edge of creativity and technology. He shares the unexpected origins of Lummi.ai, what went wrong (and what went right) while building AI-powered experiences, and how taste, team morale, and iteration played a major role in finding product-market fit. We get into: * The hilarious and humbling journey of building AI-generated imagery * Why good taste and team joy matter more than ever * The pivot moment that saved Lummi.ai * The surprising power of curating AI outputs * Why code isn’t the hard part, and how AI is leveling the playing field * His take on vibe coding, open-source design, and why now is the moment to build This episode is a reminder that creativity, clarity, and a sense of humor are some of our best tools. Mentions * Lummi AI – Pablo’s AI-powered image generation platform * Blush – His earlier open-source illustration tool * Another Design Newsletter – Pablo’s newsletter with comics and commentary * Another Design Newsletter * Pablo Stanley on LinkedIn and Twitter Follow Harrison Wheeler and Technically Speaking * Newsletter * LinkedIn * YouTube Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Are you looking to level up your design leadership and management craft? Spend an hour with me for personalized 1:1 coaching to help you thrive in your role. Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

    53 min
  7. Introducing AI Product Builders: a limited-run podcast series

    28/04/2025

    Introducing AI Product Builders: a limited-run podcast series

    I’ve been quietly cooking up a limited-run podcast: AI Product Builders. This isn’t another AI hype machine. I’m sitting down with designers and builders who are actually shipping real work. We're digging into: * Real talk on integrating AI into existing products and worklflows * Play-by-play stories of launching net-new experiences (minus the vaporware) * Honest takes on ethics, personalization, and what “future-of-work” really means for design teams. Meet the line-up: * Ovetta Sampson — Owner, Right AI: guiding SMBs through safe ML/AI adoption. * Pablo Stanley — Founder, Lummi.ai: a fresh library of AI-generated imagery. * Filip Skrzesinski — Co-Founder, Subframe: the UI design tool for the AI era. * Jason Demetillo — Lead Designer, Canva Sheets: helping the creative workforce closer to getting things done more efficiently and effectively. * Kyle Zantos — AI design consultant helping teams ship with emerging no-code aka "vibe-coding" tools. The series drops Monday, May 5th. You can follow on LinkedIn and subscribe to Technically Speaking on Substack to get access as soon as it’s available. Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

    2 min
  8. Your First Million with Backstage Capital Founder Arlan Hamilton

    13/04/2024

    Your First Million with Backstage Capital Founder Arlan Hamilton

    Arlan is a trailblazer in the venture capital world, focusing on helping underrepresented founders. She has a deep passion for both the business and personal aspects of her work, and she's here to share her incredible journey and insights with us. Summary In our conversation, Arlan opens up about her love for "General Hospital" and how her personal challenges, including overcoming homelessness and addiction, have shaped her mission in venture capital. She also dives into her latest book, "Your First Million," providing practical advice for aspiring entrepreneurs. Key Takeaways * Arlan is dedicated to diversifying the entrepreneurial world by supporting founders who often get overlooked. * Her book, "Your First Million," is a must-read for entrepreneurs, packed with strategies on navigating the business landscape. * Arlan's story is a powerful reminder that personal struggles can fuel a mission to create positive change. * For entrepreneurs, it's vital to have a clear vision that aims to benefit more than just oneself. * Preparation and self-funding are crucial steps before seeking external investment. Let's dive into the details of our chat and learn more from Arlan's experiences and wisdom. Notable Quotes * "I only do what I want to do. I figured out those boundaries, so don't feel sorry for me." * "It's the fact that I can still bounce back." * "There's no question here. And again, it goes back to who else is it affecting if it plays out?" * "We have so much agency of our own lives. And it's hard for me... but because of the way that I built Backstage and because of the things I've been through, I know firsthand how much of our own power we have." Resources * Arlan Hamilton's Book: "Your First Million" * Arlan Hamilton’s Podcast: "Your First Million" * Event Mention: Your First Million Live in LA, April 9-12 yourfirstmillionlive.com Arlan Hamilton's journey is a testament to the boundless potential within each entrepreneur, serving as a beacon for those striving to carve their own paths in business and beyond. Don't miss out on the full breadth of wisdom shared in this episode—listen now and be part of the conversation that's shaping the future of innovation and inclusivity. Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

    28 min
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Conversations for design managers and aspiring leaders, delivering real stories and ready to use tactics to help you build confidence and credibility. I sit down with top voices in design, tech, and business to open the black box of leadership. I'm your host, Harrison Wheeler, with 20 years in design and a decade leading teams from scrappy startups to global giants. It's time to get technical. technicallyspeakinghw.substack.com

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