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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

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

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

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

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

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

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

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

Krislam Chin, a designer and educator based in West LA, shares her journey in the design industry and her passion for teaching. She discusses the importance of travel for creative individuals and the need for designers to experience the world. Her studio, Hello World Studio, aims to provide opportunities for emerging designers. She emphasizes the importance of not defining success based on external factors and encourages emerging designers always to acknowledge opportunities. Key Takeaways: Learn the importance of travel for creative individuals to gain new perspectives and experiencesUnderstand why designers should have the experience to stay relevant in the industryDiscover how her studio, Hello World Studio, aims to provide opportunities for emerging designersExplain the responsibility of Millennials to prepare the field for future design workforce and what we all can learn from Gen ZFind out Krislam’s success tips for emerging designers Quotes: "If you stay in one place for too long, you just need to see different things, be with other people." - Krislam Chin"Success is what you determine what success is." - Krislam Chin"Never let the world define what success looks like to you." - Krislam Chin Timestamps: (02:27) Introduction to Krislam Chin, how she met Harrison, and the benefits of traveling to creative individuals (04:53) How she achieved her ultimate dream of being submerged in education as a student, educator, and studio owner (07:04) The interplay between teaching and being a student running a studio and the importance of providing experience for emerging designers (10:41) Acknowledging the challenges and responsibilities of students, making dreams come true for emerging designers and companies through Hello World Studio, and her motivation to move to Downtown LA (15:25) What we can learn from Gen Z, reflecting on the stress and toxic culture in design, and the responsibility of Millennials to prepare the field for future design workforce (24:48) From What If to Why Not: Success Tips for Emerging Designers  (31:01) Why the individual, not external factors, define success (34:12) How she radically accepted herself as a fun teacher using rubber duckies (37:44) How to get in touch with Krislam and collaboration with small businesses (38:48) Her appreciation for the podcast and community-building efforts About The Guest: Krislam Chin is a designer and educator based in West LA. With a passion for teaching, she has pursued a career in graphic design and recently launched Hello World Studio. She is dedicated to providing opportunities for emerging designers and helping them gain the experience they need to succeed in the industry. Connect with Krislam Chin: Website Hello World Studio LinkedIn Referenced Links: Michael Dahms Two Backpacks Book What's Next: Please leave us a rating and a review on Apple... Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

We will be diving into the fascinating story of the rise and fall of InVision. In this episode, join host Harrison Wheeler and special guest Jay Demetillo as they take you on a journey through the history of InVision and discuss the impact it had on the design industry. They explore the evolution of design tools, from the days of Photoshop and Dreamweaver to the emergence of Sketch and the game-changing introduction of InVision. Join us as we reminisce about the challenges designers faced, the joy of collaborative work, and the race to stay ahead in a rapidly evolving design tool landscape. About The Guest(s): Jay Demetillo is a design practitioner with extensive experience in the industry. He has traveled the world giving talks on design and has a deep understanding of the importance of inclusive design and bringing value to design through business. Key Takeaways: InVision was a disruptive design tool that gained popularity in 2014-2015 with its cloud-based sharing and commenting features.InVision failed to keep up with competitors like Sketch and Figma due to a lack of updates and communication.Invision's collaborative tool, Freehand tool was acquired by Miro in 2023.Invsion announced their termination of services by end of the 2024 calendar year. Show notes: 00:00 Introduction and Birthday Celebration 00:29 The Rise and Fall of InVision 02:04 The Evolution of Design Tools 02:23 The Emergence of Collaborative Work 02:51 Insights and Anecdotes 03:52 Jay's World Tour and Talks 06:39 The Rise and Fall of Envision: A Discussion 10:10 The Challenges of Designing for Multiple Devices 11:39 The Emergence of Sketch 17:01 The Role of Zeppelin in the Design Process 18:13 Discussing Envision's Early Days 18:41 Introduction to Envision's Features 20:22 The Impact on User Testing 22:14 Marketing and Community Engagement 24:30 Investment and Funding 25:17 Product Updates and Innovations 27:32 The Downfall of InVision Studio 33:17 Reflecting on InVision's Missteps 35:10 Final Thoughts on InVision's Journey Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

Chris Do, a personal branding coach and host of The Futur podcast, discusses the importance of personal branding and standing out in a changing market. He emphasizes the need to show up authentically and express your unique perspective and the value of thought leadership and writing in building your personal brand. He also shares his experience with coaching and the benefits of investing in mentorship. He encourages listeners to start now and act toward their goals, reminding them that their future selves will thank them. Key Takeaways: Gain insight into Chris' fascination with luxury goods and brandsInvestigate AI's impact on design and explore alternative approachesIdentify his most notable 20-year career projectsUncover the essence of personal branding and authentic representationLeverage social media to enhance your personal brandDevelop an audience through engaging writingImplement a two-step product development approachUnderstand different learning styles and apply knowledge effectivelyOvercome development plateaus by applying learned skillsReceive his high-level advice: What he would do differently if he could travel back in time Quotes: "People don't buy what you do, they buy why you do it." - Simon Sinek"Your CV are your qualifications, but what perspective do you bring? What about your cultural currency?" - Chris Do"Every decision you make has a consequence. Otherwise, there's no point to have a lens or perspective on this." - Chris Do"Develop in public, iterate as you go. Your audience is bought in, and you have great use case and feedback." - Chris Do"Start now. Your future self will thank you for it." - Chris Do Timestamps: (03:01) Introduction to Chris Do (04:17) Icebreaker: Why he's currently obsessed with luxury goods and brands (07:57) Icebreaker: How AI replaces designers and why it's essential to shift and explore options (08:54) Icebreaker: The 2 projects that stood out in his 20-year career (12:19) What it means to show up and brand yourself (15:01) How your social media presence can either make or break your personal brand (20:16) Building an audience through writing (22:46) Product development in 2 steps (25:41) The 2 types of learners, why it's essential to apply what you've learned, and how to navigate plateaus through development (29:41) What he would do if he could travel back in time About The Guest: Chris Do is a personal branding coach, renowned designer, and the host of the successful podcast The FuWhat'sth Chris Do. He is also the CEO and Founder of The Futur, a platform providing creative professionals education and resources. With over 20 years of experience in the industry, he has worked on various projects, including music videos and 360 campaigns. He is passionate about helping individuals and businesses build their personal brands and achieve success in their creative endeavors. Connect with Chris Do: Website LinkedIn Instagram Twitter Podcast Referenced Links: Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

Adekunle Oduye, a Design Engineer at Plaid, discusses his journey from art to design to engineering and how he became a design engineer. He emphasizes the importance of understanding both design and code and communicating and collaborating effectively. He also talks about his podcast, "Code & Pixels," which aims to provide practical guidance and insights for those interested in design engineering. He encourages listeners to try new things and not be afraid to fail to learn and grow.  Key Takeaways: Discover the importance of understanding design and code to bridge the gap between the two disciplinesUnderstand why design engineers should be comfortable with ambiguity, project management skills, and excellent communication and collaborationLearn the power of trying new things and not being afraid to fail to learn and innovate Quotes: "I think for me, it's always, you're going to learn best by doing. That's how I learned, I was like, all right, I'm going to build this thing. I have no clue. I'm going to build it, but I'm just going to figure it out." - Adekunle Oduye"Don't be afraid to try new things. You're going to try things and it's going to be frustrating and you're going to feel down about yourself. But I think that's like anything, it's like you're going to suck at first." - Adekunle OduyeTimestamps: (01:20) Introduction to Adekunle Oduye and his experience in design and engineering (01:54) Icebreaker: His current obsession with going to museums (03:23) Icebreaker: His interest in incorporating AI into his work (05:29) Icebreaker: His preference for lo-fi hip-hop music while working (06:54) His background in art and transition to design and engineering (11:32) Evaluating the role of a design engineer based on project needs (15:28) Core competencies of a design engineer: ambiguity, project management, communication (21:05) "Code & Pixels Podcast and its impact (24:58) His upcoming speaking engagements (26:31) Why you should try new things and not be afraid to fail About The Guest: Adekunle Oduye, a design engineer at Plaid, is based in Brooklyn, New York. With a background in art and design, Adekunle has a unique perspective on the intersection of design and engineering. He is passionate about using AI in his work and constantly explores ways to leverage it in design systems. He is also the co-host of the podcast "Code & Pixels," where he discusses various topics related to design engineering. Connect with Adekunle Oduye: Website Twitter Instagram LinkedIn Code & Pixels Referenced Links: That Conference Converge US What's Next: Please leave us a rating and a review on Apple Podcast. Support Technically Speaking by being a Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

Kendall "Boo Boo" Howse, a Senior Designer, Illustrator, and Musician, discusses his design journey, which started with creating artwork for his music projects that eventually led to him freelancing full-time. He shares his passion for Dungeons & Dragons and its evolution to becoming a more inclusive and cooperative game. He emphasizes the importance of community and inclusivity in design and shares his experiences advocating for diversity and equity in the tech industry. He also encourages slow progress and reevaluation of solutions to create meaningful change. Key Takeaways: Experience cooperative storytelling and communication through Dungeons & DragonsFollow his journey from creating band merchandise to becoming a full-time freelancer and eventually joining the tech industryExplore his commitment to creating inclusive spaces and advocating for marginalized communities within the Bay Area Black Designers communityLearn about community, collaboration, allyship, and systemic change from his perspectiveReflect on the challenges and opportunities of working in the tech industry as a designer and on the need for progress and meaningful action Quotes: "If I believe that I am to do this alone, if I believe that the best ideas available to me are already in my head, I am doomed to fail." - Kendall "Boo Boo" Howse"In alternative spaces, we have the power to set our own rules and create new realities." - Kendall "Boo Boo" Howse"Every once in a while, we need to take stock and see if there has actually been progress forward." - Kendall "Boo Boo" HowseTimestamps: (01:28) Introduction of the multi-talented Kendall "Boo Boo" Howse (02:24) Icebreaker: How playing Dungeons & Dragons impacts him as a designer (06:31) The history of his nickname "Boo Boo" and why he sought out alternative culture as a kid (10:02) Feeling isolated after the Murder of George Floyd, the transformation of his music from despair and frustration to hope and encouragement, and the self-made CEO myth (17:39) His path into design, freelancing, and how he almost lost his home (24:03) ERGs and Bay Area Black Designers: His career in tech and inclusion (26:29) The importance of allyship to get through marginalization and isolation and how to make a meaningful impact in the workplace (31:04) How to measure systemic change and the importance of knowing the differences between no progress, slow progress, and false progress (32:21) Ways to get in touch with Kendall About The Guest: Kendall "Boo Boo" Howse is a Senior Designer, Illustrator, and Musician based in Oakland, California. With a background in DIY punk rock bands, he developed a passion for design and visual communication. He has freelanced for various clients and worked in-house at CoreOS, later acquired by Red Hat and IBM. He also actively promotes diversity and inclusion in the tech industry by helping companies form ERGs, co-chairing Bay Area Black Designers, and facilitating Frame Shift Consulting. Connect with Kendall "Boo Boo" Howse: Email Instagram Referenced Links: Dungeons & Dragons Mass Arrest Zulu Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

Eso Tolson, a Memphis-based designer and brand strategist, shares his journey as an artist and how he developed his unique style. He reveals his passion for uplifting and inspiring people through his work, including his art projects. He also talks about finding safety and comfort in different spaces and the impact of his trip to Hawaii. He emphasizes the importance of taking breaks and finding inspiration outside of work. His love for Memphis and its vernacular language has influenced his art, which resonated with the community. He encourages creatives to stay true to themselves and make a difference. Key Takeaways: Embrace AI as a creative tool, not a threatCultivate inclusive spaces for self-expression while respecting othersOvercome creative blocks by taking fulfilling breaksCelebrate cultural influences in your artUse empowering words for both yourself and others Quotes: "AI art is just a tool to speed up the process of whatever you're trying to build." - Eso Tolson"Feeling safe is about creating spaces where people can let their guard down and just be themselves." - Eso Tolson"When I'm in a creative rut, I take a step back and do things that fulfill me, like taking a walk or engaging in activities unrelated to my work." - Eso Tolson"I wanted to celebrate the vernacular language of Memphis and highlight that it doesn't diminish intelligence or other qualities." - Eso Tolson"The words of empowerment I share are meaningful to me first, and I know that others can benefit from them too." - Eso Tolson Timestamps: (01:36) Introduction of Eso Tolson, The Multi-Disciplinary Artist (03:14) Icebreaker: His current obsession with AI art and his take on new technology (06:47) Icebreaker: What he realized about adaptability during his recent trip to Hawaii and what makes a space safe and inclusive (11:15) Icebreaker: Discover your "coffee bean" and how it can help you break your creative rut (13:42) From track star to artist: His journey from East St. Louis, IL to Memphis, TN (20:49) How he developed his unique and authentic lettering style, his love letter Spectacular Vernacular to Memphis, and why Memphis embraced it (28:11) The reason he shows up online and shares empowering messages to others (31:42) How creativity isn't just for artists, and how every person is creative in their own way (32:45) Where to find Eso online About The Guest: Eso Tolson is a Memphis-based multi-disciplinary artist and creative director known for his unique lettering style and ability to uplift, inspire, and celebrate people through his work. He specializes in hand-lettering for branding, editorial, and commercial projects. He is also an accomplished speaker and shared his story and philosophy on TEDx Talks "Less Grind, More Chill." Connect with Eso Tolson: Instagram Referenced Links: Watch Less Grind, More Chill on TEDx Spectacular Vernacular: Eso’s Love Letter to Memphis What's Next: Please leave us a rating and a review on Apple Podcast. Support Technically Speaking by being a Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe

Donald Burlock, User Experience Designer and Author of Superhuman by Design, joins the show to discuss his book and his mission to bring authenticity and social impact to the design profession. He shares his journey of self-discovery and the importance of showing up as your authentic self in a world that often pressures us to conform. He also highlights the need for unification and the power of community in driving positive change. Whether you're a designer just starting or an experienced leader in the field, his book offers valuable insights and guidance for making a lasting impact in the design world. Key Takeaways: Join Donald on his golfing journey and his discoveries about the sportLearn about unification and social connection in the remote work landscape Explore how to own your image and persona authenticallyUse Superhuman by Design as your cheat code to design success Understand his mission and how looking beyond short-lived product improvements can make it happen Quotes: "I challenge those folks to not rely on the hubris. You're not in a position as a leader to say wonderful things about diversity and inclusion and belonging." - Donald Burlock"Design is more than just creating products or services. It's about bettering the human experience and making a positive impact." - Donald Burlock"Authenticity is the key to making a meaningful contribution as a designer." - Donald Burlock"Designers have the power to shape the future and drive social change." - Donald Burlock"The design industry needs to have more conversations about unification and finding common ground." - Donald BurlockTimestamps: (01:26) Introduction of Donald Burlock, Author of Superhuman by Design (03:50) Icebreaker: His golfing journey, the intriguing intricacies of the sport, and his newfound appreciation for coordination and balance (08:43) Icebreaker: The importance of unification and social connection in the evolving landscape of remote work and independence (14:00) Icebreaker: How to own your image and persona amidst societal pressures to conform (24:31) Superhuman by Design, a decade of design wisdom and inspiration from Donald Burlock to creatives of all levels (35:13) His mission: To use design to enhance the human experience for the long term, looking beyond short-lived product improvements (39:08) How to purchase the book and engage with Donald About The Guest: Donald Burlock is a User Experience Designer and Author of the book Superhuman by Design. He has over 10 years of experience in the design industry, focusing on leveraging creativity to drive social impact. He is passionate about helping designers and creatives find their authentic voices and contribute meaningfully to the world. Connect with Donald Burlock: Instagram Website Referenced Links: Superhuman by Design Paperback Superhuman by Design Ebook What's Next: Please... Get full access to Technically Speaking at technicallyspeakinghw.substack.com/subscribe