Technically Speaking with Harrison Wheeler

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 www.technicallyspeakingpod.com/subscribe

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 www.technicallyspeakingpod.com/subscribe

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 www.technicallyspeakingpod.com/subscribe

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 www.technicallyspeakingpod.com/subscribe

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 www.technicallyspeakingpod.com/subscribe

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 www.technicallyspeakingpod.com/subscribe

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 www.technicallyspeakingpod.com/subscribe

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 www.technicallyspeakingpod.com/subscribe

About the Guest(s):

Arlan Hamilton is an esteemed figure in the entrepreneurial and investment landscape, best known for her role as the founder of Backstage Capital, a venture capital firm that champions underrepresented founders by investing in their companies. With over 200 companies in her portfolio, Arlan is a champion for diversity and inclusion in the startup ecosystem. She's also an acclaimed author, having penned titles such as "It's About Damn Time" and "Your First Million," the latter being the inspiration for her podcast sharing the same name. Her journey from overcoming personal challenges to leading a movement in the VC world has made her an inspirational and influential voice in the industry.

Episode Summary:

In this episode, Harrison welcomes Arlan Hamilton, a visionary entrepreneur and investor renowned for her dedication to underrepresented founders. The conversation begins by acknowledging the profound connection between the guest and the host, ranging from crowdfunding initiatives to shared investment ventures, effectively setting a tone of mutual respect and collaboration.

The episode delves into Arlan's passion for the daytime drama "General Hospital," showcasing her unique and relatable interests. In a powerful narrative, Arlan reveals her personal motivations, emphasizing the importance of pursuing goals that transcend self-interest. She candidly shares her journey through homelessness and overcoming addiction, and talks through the pivotal moments that solidified her resolve to make a lasting impact in the venture capital space. The discussion pivots to offer valuable insights into her latest book, "Your First Million," which serves as a practical guide for aspiring entrepreneurs, focusing on how to navigate the business world with wisdom and resilience.

Key Takeaways:

• Arlan Hamilton's profound impact on the venture capital industry stems from her focus on underrepresented founders and her personal mission that extends beyond individual success.
• "Your First Million" acts as a mentor and guide, offering practical frameworks and advice for entrepreneurs looking to make a significant leap in their careers.
• Understanding the motivations behind one's entrepreneurial journey is crucial, with emphasis on creating a vision that benefits others, not just oneself.
• The entrepreneurial path is fraught with challenges, and success often requires a blend of calculated risk-taking, resilience, and persistence.
• Planning and housekeeping are essential before seeking outside funding for a business idea, emphasizing revenue generation over investment as a primary goal.

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

Join us for more engaging and inspiring episodes by tuning in to this podcast series. Arlan...

Fonz Morris, a growth design lead at Netflix, shares his journey from working at a strip club to becoming a successful designer and investor. He discusses his role in growth design at Netflix and highlights the importance of balancing business and design decisions. He also talks about his upcoming memoir and its therapeutic writing process. He emphasizes the need for patience, self-belief, and continuous learning in one's career. He shares his speaking experiences at various events and his impact on others' lives. He encourages designers to improve their communication skills and utilize networking opportunities. He also discusses his involvement in the VC space and angel investing.



Key Takeaways:

• Discover what growth design is and what it focuses on for business growth
• Learn about Fonz's book-writing process, its requirements, and benefits
• Remember why it’s important to trust the process and believe in yourself even when faced with rejection or setbacks 
• Find out what’s essential for career growth and opportunities
• Understand why soft skills are crucial for success in the design industry and what designers should strive to be
• Explain why investing in startups can be a pathway to building generational wealth and identify the various entry points into the VC and angel investing space

Quotes:

"If you believe in something, you can get it done." - Fonz Morris"Treat yourself like a project. Don't be too hard on yourself." - Fonz Morris"Designers, we have a seat at the table, so take the seat." - Fonz Morris"Work on your communication. It is critical for your success." - Fonz Morris"Get out there, meet people, network, ask questions, get a mentor, have fun, shine, be great, and lean on a community when you need support." - Fonz Morris

Timestamps:

(03:15) Introduction to Fonz Morris and our mutual connections through networking

(05:01) His personal growth and industry impact

(06:00) On Growth Design at Netflix, retention projects, and global impact

(08:41) Password-sharing initiative at Netflix

(11:04) How to overcome impostor syndrome

(14:04) On writing his memoir, Self Design

(17:28) His early career and personal challenges

(19:57) Public speaking and strengthening his voice

(21:07) A full-circle moment speaking at Google

(26:46) His Involvement with VC and angel investing

(33:02) Encouraging community engagement in VC

(36:02) His final Advice for listeners

(37:56) How to connect with him

(39:10) How his airport habits and commitment helped with the episode

About The Guest:

Fonz Morris is a growth design lead at Netflix. With a background in computer science and a passion for design, he has worked on various projects at Netflix, including the password-sharing initiative. He is also involved in the VC space as an LP in a fund and is an angel investor and board member for several companies. He strongly advocates education and community building and is dedicated to helping others succeed in their careers.

Connect with Fonz Morris:

Website

LinkedIn

Twitter

Email

Referenced Links/Episodes: