Technically Speaking with Harrison Wheeler

About Technically Speaking with Harrison Wheeler

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. www.technicallyspeakingpod.com (https://www.technicallyspeakingpod.com?utm_medium=podcast)

Publisher

Harrison Wheeler

Category

arts · business

Language

en

Explicit

No

First episode

29 Mar 2020

Latest episode

12 Aug 2025

Latest episodes

8 of 86 episodes have a transcript.

1. 

   12 Aug 2025TRANSCRIPT

   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 (https://www.linkedin.com/in/jermainelmurray/), Twitter (https://x.com/thejobfather__), Instagram (https://www.instagram.com/jermainethejobfather/), TikTok (http://tiktok.com/@thejobfather) * JupiterHR (https://jupiterhr.ca/) * Harrison on LinkedIn (http://www.linkedin.com/in/hmwheeler), Instagram (http://instagram.com/technicallyspeakinghw) 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 (https://technicallyspeakinghw.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)

2. 

   5 May 2025TRANSCRIPT

   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 (https://www.linkedin.com/in/ovettasampson/), 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 (https://www.rightainow.com/) * LinkedIn (https://www.linkedin.com/in/ovettasampson/) - Follow her on LinkedIn for hot takes and sharp truths * The Philosopher’s Zone (Podcast) (https://www.abc.net.au/radionational/programs/philosopherszone) – She references a philosophy podcast about the Dark Ages * Gutenberg & the Printing Press (https://en.wikipedia.org/wiki/Johannes_Gutenberg) – Used as a metaphor for today’s AI hype * MoviePass (https://en.wikipedia.org/wiki/MoviePass) – Referenced extensively as an analogy for unsustainable business models * Black Death / Plague (https://en.wikipedia.org/wiki/Black_Death) – Referenced in historical parallel to today's societal reset Follow Harrison Wheeler and Technically Speaking * Newsletter (http://technicallyspeakinghw.substack.com) * LinkedIn (http://www.linkedin.com/in/hmwheeler) * YouTube (http://youtube.com/technicallyspeakinghw) 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 (https://calendly.com/harrison-wheeler) to help you thrive in your role. Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe (https://technicallyspeakinghw.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)

3. 

   5 May 2025TRANSCRIPT

   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 (https://kylezantos.com) * Twitter: https://twitter.com/kylezantos (https://twitter.com/kylezantos) * LinkedIn:https://www.linkedin.com/in/kylezantos (https://www.linkedin.com/in/kylezantos) Mentions * Claude (https://chat.chatbotapp.ai/claude?utm_source=GoogleAds&utm_medium=cpc&utm_campaign=%7Bcampaign%7D&utm_id=21151825605&utm_term=173957219737&utm_content=737256588220&gad_source=1&gbraid=0AAAAA9X0Rz31MIJUkjn1Sv0Lr5dUjcHoZ&gclid=Cj0KCQjw2tHABhCiARIsANZzDWpAenE-k8VmoVD4uuXgeXZgilst5lG50ErjIdShV6MXoblgzSyezpIaAlQ_EALw_wcB) (by Anthropic) — AI assistant used throughout Kyle's workflow * Cursor (https://www.cursor.so) — AI-first code editor forked from VS Code * Lovable (https://lovable.dev/?gad_source=1&gbraid=0AAAAA-iIxGfRAOtU9uLxEsY8PXvSWWVK3&gclid=Cj0KCQjw2tHABhCiARIsANZzDWo1twRmFZDjMq2l9BDlUhcOQ3dviJY8mwwZXQ4IS6Elxra2mSqBzooaAqZ3EALw_wcB#via=nb) — No-code AI app builder Kyle uses for software-as-gift experiments * Vercel (https://vercel.com) — Deployment platform for full-stack apps * SuperWhisper (https://superwhisper.com/?utm_term=speech%20to%20text&utm_campaign=&utm_source=adwords&utm_medium=ppc&hsa_acc=4558579452&hsa_cam=21017895584&hsa_grp=161847276860&hsa_ad=696458472633&hsa_src=g&hsa_tgt=kwd-24563891&hsa_kw=speech%20to%20text&hsa_mt=b&hsa_net=adwords&hsa_ver=3&gad_source=1&gbraid=0AAAAAC-RAnNx2HY0-CJvipugx7Yq-seMB&gclid=Cj0KCQjw2tHABhCiARIsANZzDWrvhyfTSLEutQqg9nmRgzcsavJoG6rUPPaaSgbSVS4g7lpFpX-qPfcaAnm8EALw_wcB) — Voice-to-text transcription tool * Ammaar Reshi (https://ammaar.me/) — Design leader at DeepMind; inspired Kyle's early AI builds Follow Harrison Wheeler and Technically Speaking * Newsletter (http://technicallyspeakinghw.substack.com) * LinkedIn (http://www.linkedin.com/in/hmwheeler) * YouTube (http://youtube.com/technicallyspeakinghw) 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 (https://calendly.com/harrison-wheeler) to help you thrive in your role. Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe (https://technicallyspeakinghw.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)

Inside a recent episode

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

Published 12 Aug 2025 · Transcript excerpt

[…] This is a new year, new me, but in actuality, the old you, you should be leveraging 100 to 100 ,000%. I always tell people, why do you think that your employer owns the skills that you carry with you in your body? Right? They own the time that you work for them, but all the skills you carry with them. You know, when I was working at the gym, whenever we used to sell gym memberships, right? They would give us this little thing that they call the fitness planner. Basically, you open it up and it had a bunch of questions, but the questions were kind of divided up into three categories. NGTs needs goal timeframe, right? […]

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

26,670

Score snapshot 15 Sept 2025

Apple Podcasts (US)

5.0 / 5

17 ratings

Spotify

5.0 / 5

16 ratings

Podcast Authority Score: 67 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

83

Social presence

0

YouTube

76

Engagement

51

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