Dreams and Delivery.

A podcast for tech professionals — real stories from people who deliver at work and dream beyond it. Host Christine Kahn talks with guests who are navigating tech careers, AI, layoffs and career pivots, and building something of their own alongside (or after) the day job.

Christine Kahn. By day, she's a staff technical program manager in big tech. By night, she's a musician (recording as Christine K) and a sound bath meditation practitioner, based in Portland, OR.

Season 1 just wrapped, with 8 episodes released weekly. New episodes show up in the carousel above automatically as soon as they're published — stay tuned for Season 2.

Mostly through Christine's own network — former colleagues, people she's met while building the podcast, and referrals from past guests. The common thread is someone balancing a tech career with something they're building, creating, or reinventing outside of it.

Yes — reach out through the contact page with a bit about your story and why it fits the show.

Episodes are recorded remotely (Riverside FM), hosted and distributed via Buzzsprout, and the episode cards on this page are pulled live from the show's RSS feed by an auto-syncing pipeline built with Claude — you can find that same pipeline in the Skill Marketplace.

Yes, for most episodes — see Episode Transcripts below. They're being added episode by episode, so a few of the newer ones are still in progress.

Apple Podcasts, Spotify, Amazon Music, or any app via the RSS feed — links are in the Listen & Follow section below. You can also follow the show directly on Buzzsprout.

Yes — you can become a supporter starting at $3/month through Buzzsprout (link in Listen & Follow below). Free ways to help just as much: share an episode with someone who'd get something out of it, or if you know someone balancing a tech career with something they're building on the side, send them my way — they might make a great guest.

Same person, same "deliver by day, dream at night" thread. Christine records music as Christine K and leads sound bath meditation sessions — you can find both under the Music tab above.

Christine Kahn: Welcome to Dreams and Delivery, a podcast for tech professionals, real stories from people who deliver at work and dream beyond it. I'm your host, Christine Kahn. By day, I'm a staff technical program manager in big tech. By night, I'm a musician and a sound bath meditation practitioner. Today's guest is my longtime friend and trusted guide, Jessica Valentine Nelson. She's a senior consultant in organizational change management and she runs a Substack called Lead with Heart. She just navigated her own major career transitions, so she's walking her talk in real time. Jessica, welcome.

Jessica Valentine Nelson: Thank you, Christine. I appreciate you having me. So honored to be here.

Christine Kahn: So tell us, how did you end up in organizational change management?

Jessica Valentine Nelson: Great question. So my first job out of college was being a sorority consultant. And many people are like, what is that? Especially if you're in an international stage. But that was a leadership development opportunity that allowed me to learn how to work with different groups of people from different geographies and also help inspire and influence change from the inside out. And I worked with organizations size 25 to about 250. So, right, big small groups, universities all over the all over the country. I knew that because of my sorority experience when I was appointed the leader of the group I was in charge of at 19 and had to lead a transformation that I wanted to be a change management consultant. Yet when I originally applied for all of my career opportunities to start, they said, you need more experience. And so I started in technology sales in the cybersecurity industry. A client created an organizational strategy role for me where I was the organizational strategist at Dell Technologies and created their cybersecurity intern program. I then transitioned back into being in a sales function, got education and certifications and human resources, and then moved back into change management consulting because I love training, I love people, I love chaos, and I also like being able to manage it when I can influence and control it.

Christine Kahn: You've always struck me as someone who has a really human approach in the way that you work. I'm curious, was this always the case, or was it an intentional decision you made at some point along the way?

Jessica Valentine Nelson: I think for me, I worked hard and I got lucky. And there were some rooms that I found myself in, especially at a young age where I was talking about technology transformations and learning how to work with different leaders. There were times that I thought I fit in, and there were times where I didn't feel like I fit in. And so the program management arm, the inclusion and belonging arm is somewhere I always felt like I could be my full self. In addition, I didn't have the traditional background. I was told no a lot. I tried to pivot internally at a consulting firm that I was working for, and I didn't know some baseline HR things like the 70-2010 model for professional development and other adult learning things. And it wasn't until I met a mentor, Linda Dolce Morey, who's the chief learning officer at the Executive Women's Forum, who said, Jessica, it's time for you to become a certified coach through ICF, in addition to going back to school so you can get a job doing what you love, which at the time I thought was learning and development. So there's always a part of my work that's related to growth and development, but also a big part of my heart that really leans into the transformation of self and the personal responsibility that we have as professionals to take care of ourselves while doing great work.

Christine Kahn: You know, when you mentioned that you were told no a lot, it reminded me of a conversation I had with one of my previous CEOs, Debbie Sue at Open Table. And I asked her, you know, what's work for you to keep moving up in your career? And she said, Well, you know, I've just been told no a lot, but I keep asking.

Jessica Valentine Nelson: Yes. Well, in my experience in a new hire sales program for a company called Checkpoint Software, we were in New York. There were 30 of us, 15 Europeans, 15 Americans, and we had to sell comedy club tickets in Times Square just to get used to rejection. Like it was an active choice. And I think when you're early in your career, it's easier to reach. But I also believe that for me, now being 15 years in, there's been some intentional plateaus of opportunities in my career where I needed to pause and hang on, needed to pivot behind the scenes, needed to explore new conversations. And then there were times that certain leaders didn't align with my personal values, and I really lived within that friction state of who am I naturally? Where is my professional strengths and skills best aligned? And is that value being seen and appreciated? And if it's not, then it's time for me to exit or hang on as long as I need to hang on and then and take a new leap. And I want to say for anyone listening, impacted by layoffs, impacted by this identity crisis, I would call it in our careers, that it's really critical that you clarify what you individually want and mean, and then be able to articulate that in conversations moving forward. And the more that you say it, uh, the more that you are confronted with right rejections or redirection, the more likely you are to get the outcome that you want.

Christine Kahn: Yeah, thank you for that. You know, it's it's really a time right now where we have been seeing a lot of layoffs across technology. And I do see that it's creating opportunities though for people to really think hard on what do they really want to do? Do they have a dream, perhaps a small business that they've always wanted to get running? And um, maybe you could share some insight there since I know you have also done some of your own projects on the side, like teaching yoga and and your guides, uh mentorship programs that you've done over the years. Um, would you like to speak more about that?

Jessica Valentine Nelson: Yes. I feel like a part of me naturally, call it neurodivergence or having lots of energy. I didn't find fulfillment in my career when I was in a tech sales role at work. It wasn't, it was more of the function of what I was doing. There's a great resource I read called The Crossroads Between Should and Must by L Luna. And you can watch there's a three-minute video, an hour-long TED Talk, or the actual book. But it talks about everyone who has a job, a career, and a calling, and to know which one you're in. And so for me, as my life has evolved and work has evolved, having something outside of that is really refreshing to me. And having a business for the past six years, there's been highs and lows within that times where I had more energy to do more things, and kind of where I'm at now of the I'm bringing back sharing the love of what I'm doing and the art of creating without attachment to I should be making a certain dollar value in my side business in order to pivot. Like that's not the purpose either. So lots of mentorship, lots of formal and informal learning. And I think it's important to be available to your dreams, meaning create space in your calendar to prioritize those pillars that are important to you. And I also believe and also teach a lot about the things that we often resist is where the true growth lies or where we really want to ascend. And that's not always comfortable as a in human nature. For example, I don't for the past 10 years, I've put my recipes on Instagram stories. I've never put them on my website ever. It's still the trash can that I'm kicking, but I'm saying it out loud so I have some accountability of it's gonna, I can put that online without uh beating myself up on food photography or not being a New York Times best-selling cookbook author. Like it doesn't matter. It's for my love and sharing what I love with others.

Christine Kahn: So yeah, it's interesting, uh, just as someone who's also creative but works in tech as a program manager. You try to apply some of the organizational concepts to your own projects of okay, plan out my year, what am I going to achieve this quarter? What are my goals? And it's almost like you create your own backlog for your projects, but at the same time, creativity is not necessarily linear. So you have to give yourself that room and flexibility to be able to try something out and then pivot and try something else, and maybe have a few different projects open, which is different than the traditional way you would deliver at work.

Jessica Valentine Nelson: Right. What's been really interesting for me lately, because I moved out of downtown Austin into a small historic town called Bass Drop, which for me, Austin was oversaturated with yoga teachers and coaches, still is, but there's plenty of options. And where I live now, it's more competitive, or I feel like I have more critics on my creativity. And just to see or witness how that prevents or blocks my own creative flow, uh, or allows me the opportunity to lean into okay, how can I let my life experience and what I'm personally feeling still not impact my art? And I love the book Creative Act by Rick Rubin. I need and will finish it. That's a good book. But but it speaks to what you said, Christina, of being able to pause and really get clear on your dreams and like be inspired, like creating that space. I think that's the hard thing for Americans to do or professionals in tech, especially, is how do you reduce your own noise and allow yourself to, it's not even about scheduling time anymore. For me, it's about how do I enjoy leisure and know that that's purposeful to be offline and have boundaries versus always being available via Teams or a ping or to someone else's external demand that is like not on my list for the day.

Christine Kahn: So it's like a lot of we can we could go into a whole discussion about boundaries maybe at another time.

Jessica Valentine Nelson: Yeah, and also I need help. I'm like, bring on, bring on, bring on, bring on the boundaries, but also I think uh the thought of flow state is important, like finding flow within your creative projects and your dreams, and also at work. And I think there's a lot of friction at work or sometimes within ourselves, and that's our individual responsibility to take care of that. Yeah. Because no one else is gonna do it for you. That's your own inner work.

Christine Kahn: How do you deal with resistance, you know, or friction or just whatever you want to call it, both in your own projects, but also encountering it at work?

Jessica Valentine Nelson: Well, I think it's important to know the target audience and priority level, like with it. It's a very change management thing to say and do, but kind of synthesize it. But for me, it's uh especially if I'm not connected with nature, not connected in my body, I will be a frazzled frenetic, spinning too much on two espresso human being. And so I really have to take five or 10 minutes out of the day to do yoga or before a bigger, like I volunteered to do a big creative initiative that is aligned to a big organizational change. Before I did that, I got on my yoga mat for 15 minutes and took a break because that helped fuel my like the work product is better. So I think it's being able to have that self-awareness to get out of your workchair and go get into your body through your own mindfulness practices, um, not just book in your days to think something happens before or after work. I think our lives need to be and are much more fluid uh than we give it credit for. But we're we're stopping ourselves from moving forward because we're not intuitively connected.

Christine Kahn: Yeah, I think the first step is really that awareness, but allowing yourself to pause to really get in your body and realize what really am I feeling right now? Is this aligned with what I want to do and who I am?

Jessica Valentine Nelson: Yes. And isn't it though, sometimes professionally perceived, if you're back-to-back in meetings, you're more important. If you haven't gotten a lunch break or skip lunch to meet with a client, you're more important or smarter. And that's not the case. No, not at all. Not taking a lunch break. Like for me, I work better when I do morning movement and will have a delayed start, and I can go later. Like I can work from nine to six easy or nine to seven. But if I do that, because I do volunteer stuff at night, right? Like I gotta shut it down at least.

Christine Kahn: Yeah, and and actually, this is a great segue into a hot topic nowadays, which is AI and how that comes into play in your work. I do feel that uh in a lot of uh my day-to-day AI can make things quicker where you start your day with a program, brief, or you know, just a sense of what's going on. But I'm curious, how have you been uh experiencing this change in the workplace with AI?

Jessica Valentine Nelson: Well, I think it's interesting from a leadership and pillar perspective, especially in the cybersecurity industry. I have a client who has a security policy that they won't allow us to transcribe meetings. So, what does that do? Make my job naturally a little bit harder because I need to do everything manually, which is fine. So I think it depends on the individual organizational stance. However, in my current role and using copilot and other AI tools, I think the the achievements in PowerPoint with AI, amazing. As like a PowerPoint forward consulting person, love it. Absolutely love it. Communications, though, I think it's really important to feed your AI well, as well as proofread, because people know when things are generic. I also think it's a corporate communications challenge, whether you're using A or not, to make sure you're not repeating messages. Uh, for example, I was once at an organization, they usually word-for-word copy-paste communication from a leader to two different teams, had the same errors, and it had comments and verbiage in there, like on a personal note, XYZ. Well, it wasn't personal because it was scripted, and whoever wrote it also had typos. So I think people know when there's that inauthenticity in the workplace. And sometimes I believe that organizations should put less details out there and be more straightforward, influenced by AI, but not fully detailed in the way we communicate from top down or bottom up. I do think it's problematic. Yeah, and especially in change management.

Christine Kahn: Oh, yeah, because people want that message to be just right.

Jessica Valentine Nelson: Well, and again, if it's a technical change, yes, you need lots of details. But I had a the company that I currently work for, they announced that right they were doing a big shift and we were separating the consulting organization from the rest of the firm, which is fine. And they gave everyone a canned communication and said, Well, go and be excited and share this with your clients. And it was way too long, and the clients are already navigating their own changes and priorities, so they didn't care. So I needed to personalize that communication that someone wrote and refine it into more of an executive briefing, like a one or two line, here's the here's current state, future state, and what you need to know or do about it.

Christine Kahn: Like I think the less I there's definitely still a need for a human in the loop, you know. Like, sure, it can shortcut things, but at the end of the day, you absolutely need to be reading what message you're putting out there.

Jessica Valentine Nelson: But also, it's funny, the corporate comms people, since I've written communications for a CISO before, having them sound warm and fuzzy like how I would speak is really interesting. I'm like, what? They're they're not as human-centric as I would be, but they wrote a great comm. I wrote a great comm using their and they're signing off on it. But I think it's uh knowing people's tones and being able to replicate those tones.

Christine Kahn: Yeah, well, Jessica, this has been wonderful. Thank you so much for sharing your experience, your stories. Where can people find you and follow your work?

Jessica Valentine Nelson: From a professional perspective, LinkedIn, I have a great newsletter with over 900 followers called Weekly Work Wisdom. Highly recommend it. For me, it's a place where I get to share lessons learned as a hybrid yoga and meditation instructor and a change professional. And if you're curious around my classes or programs, you can check out our website, uh Full Body Studio, as well as guidedbyjustvalentine.com.

Christine Kahn: Thanks so much, Jessica. To everyone listening, if this resonated, subscribe and share it with someone who needs it. I'm Christine Kahn, and this is Dreams and Delivery.

Full transcript coming soon — in the meantime, listen to the episode above or on your favorite app.

Full transcript coming soon — in the meantime, listen to the episode above or on your favorite app.

Full transcript coming soon — in the meantime, listen to the episode above or on your favorite app.

Christine Kahn: Welcome to Dreams and Delivery, a podcast for tech professionals and real stories for people who deliver at work and dream beyond it. I'm your host, Christine Kahn. By day, I'm a staff and technical program manager at Big Tech. And by night, I'm a musician and a sound bath meditation practitioner. Welcome to Dreams and Delivery. This is a conversation about what it looks like to stop creating for approval and start creating from identity and the tools, mindset, and creative infrastructure that make it sustainable alongside a full-time career. Nicole Rykbos is an author, publisher, producer, and animator behind Seely Books, a creative universe of children's books, original music, animations, and family-friendly content rooted in Filipino culture and storytelling. She's also a tech PM, a musician, and someone who spent years figuring out how to build a body of work that's genuinely hers. Nicole, so nice to see you.

Nicole Rykbos: Thank you so much, Christine. It's a pleasure to be here with you.

Christine Kahn: Yeah. Nicole and I worked together back in FinTech. Over the years, we kept in touch when we realized that we had music and the Filipino culture in common. And it's just so nice to reconnect with you and see what you've built during this time. So if you could walk us through your path, how did you end up in tech and when did Sealy Books start taking shape?

Nicole Rykbos: When I was nine, I started actually building databases for my family's group purchasing organization, which was later sold to Metassets. And apparently, because normal kids were playing outside, I was having fun color coding and organizing data inside for my family's company. So that's how I got started in tech. So as they were building that company, I kind of snuck in and would build databases and help with like website design back in the 90s when I didn't really know what was happening yet. So kind of got my foot in the door there. And then at the same time, I was constantly writing my own stories and poems to entertain my family of 34 first cousins and 11 uncles and aunties constantly, or to entertain my brother and sister whenever our Nintendo wasn't working right and you know, hitting things and trying to blow into the Sega wasn't working, then I would make stuff up for us to do because that's all you could do back then. And then professionally, I ultimately studied health communications and got my master's in health administration, but also tried to keep the creative side of that. So I would still make books on the side. But then eventually, once my healthcare and fintech career started to adjust a little bit, then I started to actually do more with Sealy books. So it started as a side project and then slowly became something a lot bigger. Eventually I realized I wasn't just publishing books, I was really creating a home for all my stories and music and animation and ideas that could really help people learn or laugh or just relax. And I always had a way of organizing and entertaining when I was growing up. And this opportunity kind of developed and really allows me to bring all those skill sets together, which is great. Awesome.

Christine Kahn: Can you share a bit of how your cultural identity gets woven into your creations?

Nicole Rykbos: Yeah. So I am half Filipino, and so much of my childhood was shaped by my large family gatherings with a lot of rice and karaoke and music. And as I started to help my brother and sister, help them with my nieces and nephews and help raise them, I started to notice that a lot of the media content didn't have a lot of the Filipino culture influences that I wanted them to learn about. I grew up with it. They don't have the experiences that I had, mostly because back then we had to just physically see each other. Whereas right now it's all Zoom calls with their aunties and uncles, right? So I wanted them to learn more about their Filipino culture and have more pride in knowing where their family and like this Filipino culture pride like came from, right? Because my grandma and grandma grandpa like passed away. I want them to know about the story about how my grandpa fought in World War II, was a cook in World War II, and all just from that moment, that's what brought him to America, right? And so it's really noticing how to bring those stories and history to life in a fun and entertaining way that is easy enough for a kid to digest. Because if a kid can digest it, then someone older can digest it and grandparents. And so that's where where it really came from, especially since, like I said, my grandma's not with us anymore. So I want all of her stories to still stay with them. I want them to know that it was really hard living in the Philippines during World War II. This is what it was like. This is what your grandma gave you, you know. So there were times when I was talking to a couple of my nephews and I told them that they're a one-quarter Filipino, and they just said, What's that? Like, you know, and they're like, No, I'm not. No, I'm not. I'm like, yes, you are. You have to know where you come from because our family has worked so hard just to get where we're at. And I think also just helping them to build that gratitude more. Because a lot of the younger generations don't have that anymore. I guess that's where it came from, where the motivation is.

Christine Kahn: I I love hearing the story. Uh, your grandfather was a cook. You know, I had no idea. I remember you mentioned that you were thinking of maybe making a cookbook down the line. And I wonder if if that would have some of his recipes, possibly.

Nicole Rykbos: Yeah, possibly. I mean, I I don't have any of his exact recipes, but I think that's probably where my love of cooking came from. So I experiment a lot with patisse. I don't know if you cook with patisse. It's like a fish sauce. And so I've yeah, I'm I feel like I'm cooking a lot of my southern comfort crock pot recipes and then mixing in a little bit of Filipino influence with it. So I'll make a chicken cine gung, maybe that's chicken noodle soup, but with a cine gung packet. Or I'll make a southern meatloaf with uh a lumpia package. So it's like lumpia tasting with the meat, but then I'll use the Filipino banana ketchup on top. So it's like a Filipino meatloaf.

Christine Kahn: Yeah, and for for those who don't know what lumpia is, it's kind of like an egg roll or Filipino style of egg roll. Yeah, yeah. I've noticed you're just really intentional about what you're creating and just you're building the whole infrastructure for not just the books, but even beyond it. And I just love how you have that instinct to dream big and strategize for future growth. Because even when we were chatting recently and I was telling you about my podcast, you'd given me some great suggestions of hey, you could totally write a book about some of that someday, or you could write a course about how to build podcasts to help other creators. And I I've actually been starting to document my process a little more intentionally after that. And I'm testing out a Claude skill that I'm building that I could share with other creators. So you got the you got the gears going, but uh I love how you just do it naturally. And um maybe you could share, share more about how you know how you built this and how AI has helped you and and some of the intentionality about your process.

Nicole Rykbos: Yeah, so I guess the process really just comes from where the need is, whether it's the story that's needed or a lesson that's needed. And it started really with my small group of friends. So a lot of my friends are having kids right now, and a lot of them are struggling with oh, so and so can't share very well, or so-and-so doesn't know how to say please or thank you very well. And so the creative side, I kind of pulled those ideas with what the need is within my social circle. Sorry, within my social circle to then develop, okay, where are they at right now? What are they using right now? So for instance, my sister uses her phone and pulls up YouTube to put in front of her kids whenever we're at the restaurant. And that tells me, okay, it looks like parents are going to need an animation and possibly even a book to get them away from screen time for a little bit. And so it's really just figuring out what's needed and then what is the most efficient way to procure that? For example, with my animations, I did a lot of research on what would the best animator product be? Where can I own the licensing after subscribing to it? Those are things that I have to think about. And then on top of that, how much time is it going to take for me to produce this? Is this something that someone else can learn about or that someone can use? So a lot of it goes into if you go back to the project management. I have my idea. For example, with my sister and her kids not learning to say please and thank you. Okay, have the idea. Let's test it out. What's going to work? Let's have the book, let's have the animation, which one of these? So it's really doing things to test. I'm constantly testing things out. And then maybe I'll expand upon it if it's really, really successful or if I'm getting a lot of people that like said idea or said project. But yeah, it's really trying to be strategic and really knowing that AI tools are tools. Anything creative behind it, there it's called a prompt engineer, right? So the AI prompt engineer, they're the ones that are behind it and fueling it and creating it. I I think a lot of people don't understand that it's not entirely AI created, a lot of these things. Like a lot of it is you come up with a story, you have the idea, and then it kind of helps guide you towards the best path moving forward. Yeah, absolutely.

Christine Kahn: And and going back to creating in your own voice, you you train the AI to have your tone and to craft things a certain way, and you're giving that feedback over time so that it really sounds more like you and your message. But yeah, definitely it's it is a tool, you know, that can can help things move faster. Like I'm using this Riverside FM to record this session and you know, testing it out to see, well, this is going to help with the sound quality. But you know, it it's it's like you said, it's just constant testing and iterating and seeing what sticks. But I love how it just starts from a need and an idea and something that is, you know, meeting what is part of your your belief and mission, which I think is a good segue into how you're partnering with uh the team only stronger. Could you tell us more about that partnership and and how that came about?

Nicole Rykbos: Well, yeah, so Team Only Stronger, they are great partners. And my cousin is actually the one who developed this team. They're a local, not-for-profit organization in San Diego. And I was just trying to come up with a way to help them in any way that I could. So they're really trying to help reduce and prevent child abuse in the communities. And I know it's a very like touchy topic that nobody wants to talk about. And so I helped them create a story. I think it maybe took me a couple of days about body safety. And I I talked to his daughter, who was um unfortunately impacted. And that's why he created this whole team, not for profit for her, to give her strength and help her and help her share her story in preventing this from happening to other kids. And so I helped her create the story, and then she actually created the illustrations for this book. And I asked her, What's her favorite animal? And she said, a bunny. And so I was like, okay, let's do warrior princess bunny because you're stronger from this and you're gonna be a warrior now. And that, yeah, she just loved it. And I think it sold over a hundred books or something on Amazon. So I gave them that story. All the proceeds for that story go towards team only stronger. And I created an animated story for them too. If they wanted to share that, so then they'd have the book and the animation if they wanted to just show it. But I think helping people even a little bit in that way, it just makes all this work worth it, right? Even if just like one kid actually understands this is not supposed to happen, that means I'm a success, right? And so I'm integrating team only stronger information in all of the books and trying to integrate them in all the animations I'm doing to help with that message and and help get that through to other communities just to help for the future. Yeah. Yeah.

Christine Kahn: Yeah. Thank you. Thanks for sharing about that. Yeah. I don't know how you balance it all between your tech work and all of the creating on the side. Any tips that you would share with others who want to do a little more of the same?

Nicole Rykbos: I would say do a little bit at a time for everything that you do. So for instance, in my music, I might create develop one song a day, and then I might develop one story a day, or maybe write one page for a book a day. It'll eventually come together. And a lot of people just give up because it's really hard if you try to do it in one day, right? But uh just giving yourself a little bit of grace, I think, is advice I would tell people. 1% better looks different to other people, right? So if you say this person worked out for an hour, so that means they worked out. Well, to me, working out is doing maybe 16 squats, and I called, I checked that, check that off the list, and that tells me I worked out. I did something to work out, right? And so, especially for overachievers and type A personalities, I'm reaching out to you and saying, give yourself a little bit more grace. I know it's hard to not be hard on yourself, but just do a little bit each day, and that will help your brain check the task list off.

Christine Kahn: Yeah, it is about consistency, right? And just kind of forming that muscle, building that habit a little bit at a time, then just gets easier and easier to thread it into your day-to-day.

Nicole Rykbos: And rewarding yourself with like a boba or a snack also helps. I love food, so that helps you.

Christine Kahn: What's exciting you for Seely books? What's coming up next that you've been working on?

Nicole Rykbos: My goodness. I am very excited, which I'm I'm working on it right now. It's a lot, but I'm in uh the process of creating a uh scam fairy tale book with cats. So my gosh. It is going to be fairy tale rhyming stories that teaches kids, parents, grandparents about what could potentially happen with tech. So, for instance, one of the stories is about the love bombing. So there's a love-bombing cat prince and the princess, and how what do you do? You're not supposed to click on it, you're not supposed to give them any information. So at the end of each of the fairy tales, it'll tell you the tech safety tips of where you might see this, what not to do, and then it'll list them all at the end of the story. But then I want to create an animation for that to help parents, grandparents, kids learn about tech safety and scams because there's nothing right now that helps teach them about scams and it's impacting so many people, but people don't want to say, well, I've been scammed before because it's kind of embarrassing, you know? Like, and so I want to help try to save maybe one person from getting scammed in the future and gonna deal with cat stories. Very excited about it.

Christine Kahn: It's so important for children to learn this, to make this accessible to them. I was just recording the episode before this, and we were talking a bit about how he has a child and what is learning going to look like for them. And you know, he's two years old right now, but he's hoping that by the time that he's in school, maybe some better systems are in place to protect the learning. Because with AI, it's very easy to skip the learning part and just say, Well, why do I have to do this when I can just click a button, you know? Versus there's still an element of thinking that needs to happen to build that skill before you can really leverage all of these tools.

Nicole Rykbos: Yeah. But it's almost like we need to have like a 90s camp where kids don't have AI, you're gonna have books, you're gonna have to research with the books, go to the library, you know, print things off.

Christine Kahn: Yeah, but it's it's so hard because there's there's an element that you can't control. Like they're going to see these these iPhones and and other devices everywhere they go. And my brother and my younger sister both had children this earlier this year, and already I see the child's desire to just look at that bright screen while they're looking, you know, they're using the phone themselves. And it it's just so hard. I don't know, I don't know how how parents are going to do it now and keep them shielded.

Nicole Rykbos: Because on one hand, you want them to be in front of the tech because that's how they're going to potentially learn in elementary school, right? They might have an iPad or a laptop instead of the books that we carried. So you want them to learn about the same time. You are like, how am I going to shield them from XYZ?

Christine Kahn: It's almost almost like guardrails. I think back to us growing up with with computers and YouTube and everything, and having at least screen time limits or something around that where parental controls could be added. But yeah, it is definitely an interesting space to solve for. And I'm glad that we have someone like you creating good content for it and you know, helping to tell those stories that that children need to hear and help them get ready for the real world.

Nicole Rykbos: Yeah. And I know this book that I create's probably going to be out of date in a matter of months, but at least I can share what stories have or could potentially happen.

Christine Kahn: Yeah.

Nicole Rykbos: To help them learn.

Christine Kahn: One thing that I wanted to ask you to share here was about how when you were exploring licensing tools to use, you came across one where if you stop the subscription, it wouldn't allow you to own your your content anymore. Yeah.

Nicole Rykbos: So whenever I was trying to look for a music tool, for example, there are music tools where you have to keep the subscription in order to continue to own the license. Wow. So I learned about that actually watching a YouTube video on AI music platforms. And so if I hadn't done that, then I would have never learned that if I stopped the subscription, then I no longer own the music. So all this hard work producing, distributing it, I don't own it anymore after. And so I had to kind of like backtrack and say, okay, let's start from the very beginning and let's find a different platform where I will still own the license and I will still own the music even if I stop my subscription. And so I found another platform where I can actually physically download the license for each song. So I own it and have it, which is really reassuring. So I guess my advice is to really read the fine print and do your research. And in creative work compounds over time, which you well know with all of your creative endeavors. So it's really worth understanding exactly what rights you're keeping before investing a bunch of hours into a project. I know it's not the most exciting part of creating things, but I would rather share this lesson with someone to step back and read the fine print first rather than doing all this work and then having to backtrack and getting disheartened.

Christine Kahn: Yeah, wow, definitely into your research, my goodness.

Nicole Rykbos: Mm-hmm.

Christine Kahn: One thing that that I have been thinking about lately is I saw a friend recently post about how she learned that her music creations had been used to train an AI model without her knowledge or consent. And I mean, it just begs that question of what is really okay here and how can you make sure that your work is protected as an artist? I don't know what the answer is, but it's definitely just been on my mind lately of, you know, in some ways I'm really happy to use these these AI tools because it allows my flow to go faster, but I do wonder is that going to remain my content or once I train the model, is it just basically out in the universe? And I don't know.

Nicole Rykbos: Yeah. That's yeah, that's something that I've always thought about too. And with these music platforms, I've noticed that there's uh an ability to publish something which on on that platform, which can help bring more visibility to your name, but then that also gives other people the ability to take that song and maybe replicate it or do something else. So I've been kind of leery about publishing my work directly on the platform. So I guess maybe that's my way of trying to avoid that scenario and just distributing it directly on a separate platform. I don't know if that works.

Christine Kahn: Great insight.

Nicole Rykbos: Yeah, I'm not exactly.

Christine Kahn: It's hard because a lot of people are already on those platforms. And especially starting out, you want to make sure you reach as wide an audience as you can. At least that's what's been on my mind. But I do think of, say, Taylor Swift, who ended up re-recording some of her albums just to get it off a certain publisher. And perhaps down the line when we have notoriety and fame, then we can consider getting off the platforms to protect our intellectual content better. But I'll definitely keep researching on this. And um, thanks for sharing your your tips and how you're making it work for you. Where can people find you if they want to get in touch and if they want to read your books, listen to your music?

Nicole Rykbos: Yeah, so the easiest place to go to is SealyBooks.com. So that's the hub where my Amazon link is all my YouTube channels, SealyBooks and my Jazz Castle Ambience, or they can connect with me on LinkedIn. And there's also a link on there for only stronger.org. If they want to learn more.

Christine Kahn: Wonderful. Thanks so much, Nicole.

Nicole Rykbos: Yeah, my pleasure. Thanks for having me.

Christine Kahn: To everyone listening, if this resonated, subscribe and share it with someone who needs it. I'm Christine Kahn, and this is Dreams and Delivery.

Christine Kahn: Welcome to Dreams and Delivery. This is a conversation about what it actually feels to go from building inside a big company to building something completely of your own. The role AI is playing in letting one person do what used to take a whole team and what martial arts teaches about balance, perspective, and the founder life. Lawrence Ma is a software engineering manager, turned founder. After a layoff from MailChimp, he built Acquire Scout. A platform that aggregates business listings from across the web, scores them against your buyer profile, and guides you through every step of acquiring a small business, from first contact to closing day. Currently in beta, and he's also a dad and a recently enrolled martial artist figuring out how to build something that's genuinely his. Welcome, Lawrence. It's so nice to meet you.

Lawrence Ma: Thank you, Christine. Thank you for having me.

Christine Kahn: Yeah, I've just been following your journey and you know, just so inspired to see what you're building and I wanted to learn more about it. Can you tell us what does a day look like for you now compared to when you were an engineering manager?

Lawrence Ma: Yeah, that's a great question. it's a little weird because obviously way more structure when you're working nine to five. I worked with a team that was based in Atlanta, so East Coast time. I'm on the West Coast. So I woke up, you know, it's pretty early, first meeting, like seven, seven thirty AM, all the way till two, two thirty PM. And that was just like a straight block of meetings. but now don't necessarily have to wake up that early, but I still sort of wake up. kind of close just to kind of get into that same swing of things. I kind of created a schedule for myself in the very beginning, right after the layoff of like, what do I want to do in terms of applying for jobs, maybe studying for interview materials. And then also what I'm doing right now, which is like building a business, building acquire scout, which recently has taken up basically all of my time. And so the weird part about that is just like now that it's my business, that's something that I'm starting, There really isn't a stopping point. There isn't like, okay, at a certain point I can stop. but I am trying to make sure that, you know, dad comes first. Like I do all those things, take care of my kids, I get them from school and daycare and and so on and so forth. and then afterwards I'll do some more building like after dinner, for example, or after the kids are gone to sleep. but that can take me through sometimes two, three AM. I think last like five or six nights I've been sleeping at like two or three AM. So it's kinda hard to stop. It's kinda hard because when you're real you're like, This is something that I want to build, something that I wanna make a reality. It's really hard to like stop doing those things. But it's really exciting though. So

Christine Kahn: I can really just working on the podcast has been so fun for me that it doesn't feel like work, you know, you just get up and you're like, okay, I gotta prepare a script for tomorrow, you know, and or edit something and could you tell us more about Acquire Scout? How did you come up with that idea and what's it been like building it?

Lawrence Ma: Yeah, absolutely. Yeah. Yeah, I mean, I had been looking into buying a business for a while now, but obviously being laid off was sort of the catalyst that I needed to really get into that. So that's actually where it started. I started as me, trying to buy a business, looking in the tools that are available to buyers and realizing there really wasn't anything. There really wasn't anything that was gonna help me in my journey. And so Because of that, I just started building my own tools. But I at that point I wasn't thinking, I'm gonna start a company with this. It was more so, I'm building these tools, it's looking, you know, like it's working. and then I realized after a while, like, well, why why wouldn't I just create a business around this? Why wouldn't I create this as a tool and start like actually trying to market this? And that's where it started. and at this point, it's been like what, two or three weeks, which is sounds crazy because it feels a lot longer than that, but I'm already at beta. I already have real people, you know, using it and trying it out and also giving me fat feedback on like what their experience is like. So it's been super exciting the past like like again, two or three weeks.

Christine Kahn: I think it's a super timely thing to be building, you know, with widespread take tech layoffs going on, various companies. Oftentimes people are looking to start something new or say they get a lump sum of severance that they want to figure out how to, you know, have better tax implications in the next year. It's definitely been something I've been thinking about. And I'm curious of how you've been able to work with an AI assistant to make this a lot streamlined for you, given you are a team of one right now and building software, launching it, marketing it, all of that is a whole thing.

Lawrence Ma: Yeah, it's crazy. I actually have a a video that I recorded, I think, last night, kind of reflecting on this because I was kind of looking back through my GitHub, through like all the work that I've done on Acquire Scout and realizing that okay, in like about two and a half, three weeks, I've gotten to this point where I've been working beta. And thinking back through my career, I I've led two different startups. so small teams, scrappy teams, and we build kind of similar things, dashboards and stuff like that. And Trying to think like, okay, for those teams, like how long would it take them to build something like this back then? And maybe it was like two months or something like that for a team of three or four engineers, which sounds crazy. It sounds absolutely insane that that a team and these are great engineers too. don't get me wrong. So AI is just like really is accelerated the building for everyone and especially for people like me who are like solo pioneers and we can like We have the idea, we have the the product that we want in our heads and we just wanna put it out there. from going from idea to actual working beta is insanely fast. So

Christine Kahn: Yeah, that that's incredible. Do you think if this scaled and became a larger thing that you would eventually need a team to keep it sustainable?

Lawrence Ma: Potentially. I think it depends on the this opener, I think, at this point. I think because I have an engineering background, I think I can hold off for a little bit longer. but definitely as it scales and hopefully it does, that'd be a great problem to have. if I get more and more users, I do feel like you probably need some more help and some more engineering help that really just like is focused on scaling. that you know, obviously if it's just purely vibe coded app, I just don't feel like it's at that point where we can just say like, okay, just go go nuts, like we're gonna go have like ten thousand, hundred thousand users on a particular platform. but where I'm at where we're just trying to start off and trying to validate an idea, it's more than enough. So

Christine Kahn: Would you have any tips for someone who's starting their own thing as far as making sure you don't over-engineer anything or have the right infrastructure from day one?

Lawrence Ma: Yeah, I would say before you even build anything, go talk to people. Go figure out if the problem that you're thinking about actually exists for other people. and just ask them, like, hey, if I were to build a solution like this, would you be interested? Yeah, I think that is very, very powerful. I think it was different for me because in this particular space, like I was the customer. So I knew for a fact, like, hey, I can't find, I cannot find a solution like this. and I think that's the main thing is if you can find the problem, and then really talk to people, then I think it's worth building something. But don't just build something and just hope like, okay, I hope I'm I'm gonna build the solution and I hope I'm gonna find a problem for this. So yeah.

Christine Kahn: How would you measure if it's taking, if you know, there's getting traction? Have you set up any analytics or is it still early stages for that?

Lawrence Ma: I think it's early stages for that now, but just in terms of my conversations with different people in in the industry, I definitely feel like there's a need for this, even especially from the advisor point of view. So people, not just people who are buyers, but also people who are advising buyers, can use a platform like this to help like track the the buying journeys for their clients. And I've already talked to a bunch like that, and I'm just seeing a lot of traction there as well. So It definitely feels like one of those things where people are already asking for it. I just have to build it, which is never like anybody who's like any has any kind of experience with startups, that rarely ever happens, is that there's just a you know, these this product market fit and people are just waiting for you to build it and just like okay, once you build it, let me know. And that's where that pressure comes in, where I'm like, okay, I have to be up till two, three AM in the morning to try to get this thing built.

Christine Kahn: Yeah, I I definitely see a need for this both on the side of people who are starting something and want to get in touch with investors, but also people who are looking to have passive income on the side and realize that perhaps the old model of just investing in stock and banking on A career forever is really gonna get you that stability in your life and especially for for families, you know, like your dad, and you have to think about the long term, not just for you, but your whole family unit. So it's definitely needed, and I'm so glad that you're building this. I'll definitely get on that beta soon and test it out for myself. can you share more about your

Lawrence Ma: Mm-hmm. For sure.

Christine Kahn: your experience of being a father and how how that's looking like now that you have some time to structure the day better the way that you want.

Lawrence Ma: I mean, I've always been blessed, at least for the past five, six years, being able to work remotely. and that's definitely not not something that I want to give up. but I think, you know, just knowing like also the way that companies are acting with a lot of like return to office mandates. I'm not really down for that. I want to continue working remotely. And so like buying a business and also starting my own is also another way for me to think like long term about like how do I like lock in. that flexibility. How do I lock in that ability to spend more time with my family? because that's super important to me. obviously wanna spend as much of my time as I can with my boys. They're eight and three at this point. So especially when they're young, I wanna make sure that I I spend more time with them. So

Christine Kahn: That's awesome. And I love the remote life. I am also remote. And it's just been wonderful as someone who is creative and likes to make music on the side to be able to take a break if I need to, to focus on something different. But also in tech, you're often working nights or whatever the needs are. So you kind of figure out how best to manage your time around that.

Lawrence Ma: Mm-hmm. Yeah. Mm-hmm.

Christine Kahn: Why martial arts? Like what was it that attracted you to to try something different?

Lawrence Ma: Ha. Yeah, I I don't know. I just like I kind of always wanted to. I never really had a chance. I had I always I told a story to my son a long time ago about how I actually got into karate when I was maybe five years old. And it was at that time there was like a big class. They only accepted five students out of like thirty people who applied and I got it. I came home, told my dad, like, hey dad, I got into karate class and he actually told me he didn't want me to go or didn't want me to attend the class because he was afraid that if people knew I would fight or knew how to fight, then I would get into fights at school. And so I was sort of like this moment of like, no, I I wish I had like, you know, was able to do that. And then I just kind of forgot about it. I just like never really thought too much about it. And then partly because of the layoff, partly because of just like, you know, things that's been going on recently, I just felt like why, why haven't I just been holding off on these type of things? Like Just just give it a try. Who cares? I think the other part of it too was thinking like it's kind of embarrassing. Like this is like mostly kids in these classes. There is a family class, which is one that I'm in, but just feeling like, I don't want to be like, you out there in the class and all these other parents that I I know and I'm friends with are all just watching me in class. But it ended up turning out great. And actually I convinced one of the other dads to join me. they kind of like very funnily call us the dad vengers.

Christine Kahn: That is.

Lawrence Ma: in class. So we we just we've been attending class and we already got my first belt promotion so I'm not a white belt anymore. I'm a senior white belt. but it it almost is like an analogy for my whole life right now. I just feel like right now I am just like a white belt in all aspects, like business acquisition, starting my own business and taekwondo. It's like kind of a great analogy for what I'm going through right now. And I also I just feel like who cares? Like that's part of the journey.

Christine Kahn: I love it.

Lawrence Ma: Like everyone has to start somewhere. you can't automatically be like a successful entrepreneur unless you are a beginner entrepreneur. You can't do that. So that's where I'm at right now. And it's just like one day at a time just trying to, you know, get there and you know, maybe one day I will be a black belt in all of those things. So

Christine Kahn: Yeah. I love that, just having the beginner's mindset in everything because why not, right? What have you got to lose? Try something, see if it takes. If if people are looking for someone who's creating what you're doing, you need to make yourself visible, right? Or else they're not going to find you. It's funny, that was sage advice from my mother when I was young. She's like, Christine, people are not gonna know you exist if you don't go out and socialize.

Lawrence Ma: Yeah, why not? Absolutely. Yeah. Exactly. Exactly. But also like what you're doing with the podcast and then I'm I'm trying content creation as well. But another thing that I just felt like, okay, I'm a beginner at it. I'm just gonna start and give it a try. But I mean, how can you ever get good at something unless you try at it or at least start it, right? So

Christine Kahn: man. Yeah, I was gonna ask, wait, have you already been doing videoing and and editing and all that stuff prior to this? 'Cause it just felt so natural from the videos I saw, you know, and maybe being a dad and videoing them growing up kinda gave you the skills you needed for this.

Lawrence Ma: Yeah. Mm-hmm. Yeah, I mean, really it was just personal before. Like I did editing, but editing just like family videos and like I'm in my personal Instagram account, like editing the kids and stuff like that. And but yeah, for the content creation thing, again, another thing that I just had always thought thought about doing, kind of was thinking like maybe I should try it. And literally it was like after the layoff announcement, I just thought I'm I'm gonna try it. I'm gonna try to do this. And I released my first video. the first video was just me, just like a raw video talking about my layoff, kind of like an instant reaction to it. And at that this video is now or this real on Instagram is now at like 80,000 views or close to 80,000. So that's what sort of has like spring like been the springboard for the entire like Instagram content creation, you know, career. So and not a career, but just like the the venture, I guess. but yeah, it's been really, really fun to kind of like talk to people and obviously it's very relatable right now, just because a lot of people are going through a very similar situation. so but the other part of it is it all sort of feeds itself, you know, like the content content creation, starting my own business, buying a business, they all sort of feed themselves. And it's been kind of a syn synergistic thing going on where I'm doing all these things at once, but they feel like they're so connected.

Christine Kahn: Yeah, that's so true. And I was actually working on my my professional website over the past weekend and I realized there's so many interconnections between my creative life and how I work and my style and just how I connect and build communities. And As I've been doing the podcast, I've been meeting people who are similar, where they have a technical expertise or they're just really good in doing their day job, but they're creative too. And people are referring other people to me, like, you know what? I think you would really love to meet so and so. And I've just been having really wonderful conversations with people. And I I recently moved to Oregon, Portland last year. And so I've been wanting to build a network out here and I r ironically, through this, I've been able to find more local people who are also working remotely and want to find somebody to build with. So it's been really cool. And I couldn't have known what the journey would look like and I'm still figuring it out as I go, but I'm having fun and it's giving me this creative outlet, which I think also is letting people share their stories and

Lawrence Ma: Mm-hmm.

Christine Kahn: fuels me because I like to help people and give them a place where they can connect with who is looking for them. So I figured I'd reach out to you. I'm so glad I did. yeah, what what AI tools have been your go-to? I've been using Claude mostly, but I'm curious for someone who's actually built an app end-to-end what it really looks like in in the investment side of what you I gotta buy and

Lawrence Ma: Yeah, it was it's really great, yeah.

Christine Kahn: Get that infrastructure set up.

Lawrence Ma: Yeah, I've been using Claude as well. so I just kind of very recently kind of signed up for Claude. I went all the way to Max actually, Cloud Max. I was starting out of a pro. I was starting off a pro, but I realized like I every single day I was running out of, you know, usage. So and I'm just building a lot these days. So I just felt like, okay, I'm just gonna bump it up to max for now. Maybe I'll, you know, able to bump it back down once things kind of calm down a little bit.

Christine Kahn: Wow.

Lawrence Ma: but I've been building so much with it. So it's definitely been worth it. It does definitely feels like, yeah, it's expensive, but at the same time, like think about how much more I get to do. Like this is used this used to be three or four engineers. I had to do this. Now it's just me. So instead of hiring somebody, I can just do this with Cloud with Cloud Max. So yeah.

Christine Kahn: Yeah, it's funny. I've also been hitting my limits with pro and I haven't gotten to that point yet where I feel like I can justify it, but also there's that opportunity cost, right? Because there's so much possibility now if you get in first and you're testing it before others. Like I I was on the path to create a skill for creating podcasts. And as I was on Reddit looking through the podcasting community,

Lawrence Ma: Mm-hmm. Yes. Yeah. Right. Exactly.

Christine Kahn: Someone reached out to me that they had already created one and that I should test it out. So I'm like, whoa, I mean, that's cool that I was thinking similar, but also, you know, it it's a timing thing of any change in technology, like when mobile came to be, it's just this new channel or or tool set that you can use. So it's actually, I'd say, a blessing that we're able to test these things now and have.

Lawrence Ma: Yeah. Yeah, yeah, yeah, yeah, for sure. Mm-hmm.

Christine Kahn: the time to to focus on it.

Lawrence Ma: Yeah, absolutely. But I I it's so funny you say that because I felt very similar where I'm like building these tools and then I'm like, I heard this other tool that's similar to Aquirascout that's already out there or has been out there. And I think the way I think of it right now is just like this is all just a foot race. And it's not just it's it's a foot race, but it's not a sprint. It's a marathon. And so even when you see other competitors on the field and they're just like running, you just have to keep going.

Christine Kahn: Mm.

Lawrence Ma: And just realize, like, look, maybe they'll get tired. Like, I don't know. I have no idea. Maybe I'll I'm just gonna keep going and see how far I can go. but not really thinking about what other people are doing or running their race. I'm running my race. I can only I can only run my race. And so I'm gonna keep running and then I'm gonna see where it lies at the end of it. But I think it's it's easy to look at what others are doing or what maybe somebody else is. create a tool that you were thinking about creating or a site that you were thinking about creating. Like there's always going to be competition. There's competition everywhere. And so the matter is like, are you going to stick it out? Are you going to keep it going longer than they are? And are you eventually going to have a better product than they are? And to me, I feel confident that I can do that. but just a matter of like keeping keeping with it. So

Christine Kahn: Yeah, that's great advice. And I think feedback to seeing that others are building similar just confirms the need for it, that there is a market and I mean like any product, there's always competition. So like you said, just keep doing it and and try to be consistent and over time, you know, make adjustments. And what I'm finding in in my process is

Lawrence Ma: Exactly. Yep. Mm-hmm.

Christine Kahn: I'm refining it as I go and realizing who my audience is and then I can better target certain topics. But yeah, it's it's been a fun ride.

Lawrence Ma: Mm.

Christine Kahn: Where can people connect with you if they wanna learn more about Acquire Scout or even just partner with you?

Lawrence Ma: Yeah, so acquires scout dot com. that's my that's the website. still in beta right now, so not quite like out to the public. also my socials, so Instagram is the main one right now. It's the Lawrence Ma at the Lawrence Ma. And then TikTok is the same handle. so yeah, those are the main ways to contact me.

Christine Kahn: Mm boom boom. Awesome. Thank you, Lawrence.

Lawrence Ma: Thank you so much, Christine. Thank you for having me.

Christine Kahn: Welcome to Dreams and Delivery, a podcast for tech professionals, real stories from people who deliver at work and dream beyond it. I'm your host, Christine Kahn. By day, I'm a staff technical program manager in big tech. By night, I'm a musician and a soundbath meditation practitioner. This is a conversation about what the hiring landscape actually looks like right now. Which skills hold when titles get rebranded as AI reshapes work, and how someone with deep infrastructure knowledge figures out which new doors are genuinely worth walking through. Jack Smith is an infrastructure project manager who began his career on an IT help desk and spent more than two decades growing into leadership roles across cybersecurity, data centers, networking, and digital transformation. Throughout that journey, he learned that success isn't about avoiding failure. It's about learning from it and continuing to move forward. Today, he combines those lessons as the host of IT Horror Stories with Jack Smith, where he explores the human side of technology and the stories behind the systems that keep our world running. Jack, it's so nice to see you. Welcome to the show.

Jack Smith: Thanks for having me on. I have gray hair, I have a gray beard. My first job was installing Windows 95. So that's uh that puts the start of my career in the late 90s. And I have done technical things for about uh five, six, seven years, and then moved on to more organizational things. So that I did some boring things as planning and change management and release management for few companies, and then moved into what is called IT infrastructure, and that means, in theory and in reality, I spent the last 10-15 years moving data centers, opening data centers, putting new cables into warehouses, moving companies, and make sure that they had all their network in place, their power in place, their external network connections, their internet, and then with all the new advanced stuff technology today, is it how do we keep on doing it and how do we translate this into what the market needs today and what it does not need today?

Christine Kahn: Would you say that along the way you've developed certain skills that transfer from different jobs to different roles?

Jack Smith: Absolutely. So you start off as technical, everything is planned for you, you don't need to worry about silly things such as a budget or a communication with a supplier. Well, with a customer, yes, with a supplier, you don't care. You just open the PC out of the box and you set it up. And when you go into different roles, you you kind of must have a base knowledge for some skill, but it lets you evolve it and grow it, and from there excel it and become very, very good at it. And over the years doesn't go in weeks or months, takes years because you also need to find out what doesn't work.

Christine Kahn: So true. Can you paint the picture of what the tech hiring landscape is like right now, especially with AI in the mix?

Jack Smith: What I've noticed, well, it's more once you get past the hiring, it's okay. Currently, the hiring process is very AI-minded. So, what I see is that everybody is using AI to write their resumes. All the hiring companies are using AI to scan through the resumes, and in the end, I see very few correct profiles get hired. If I look on the job market, I see the same request for say somebody wants a senior Java developer. I'm just making things up.

Christine Kahn: Yeah.

Jack Smith: I see those things come by again and again from the same company every three months, which means that the hire that they did was obviously not a success because they cannot be growing that fast that they knew that they need three to four new developers every month. So the things aren't really working out. And I've noticed that this initial non-human hands-attached screening is luckily going away, and that the right people are getting the right opportunities and the right shots at a good job again.

Christine Kahn: What would you say people are doing wrong from the hiring standpoint with you know using the AI tools? What do you think is the issue there? Is it just the way they're describing things or keywords?

Jack Smith: Keywords mostly. I've had a thing myself where I was not myself but helping someone finding a job in the IT infrastructure world. And the resume that was sent out said, okay, this person has 10 years of data center experience, has five years of cloud experience, so with cloud systems left and right. And the feedback that got was, by the way, completely AI-written email. You could just tell from the way it was it was formed, was well, yes, you have a very interesting resume and we will keep it on file. However, we do notice that you have five years of cloud experience, but we were looking for public cloud experience. And then because the search term was public cloud instead of cloud, they completely missed out completely human hands off this perfectly fine technical person that would have had a great career in this company.

Christine Kahn: Yeah, it's maybe a little too strict in the definitions or just the wrong definitions.

Jack Smith: Yeah, it isn't it is an ant-and story. And say you want this many years of of experience, it's not checked. So you need experience with AI building, and they said, well, okay, sure, but nobody knows, oh, you need 10 years of 10 years of experience, impossible, that doesn't exist that long. Well, not in the big public market anyway, but still somebody types that in and it is not checked, it's not validated, and in the end, with all the well filters and search criteria, that's where things go wrong. Plus, that I do get the feeling that in order to save costs or to be more flexible or to use the terminology agile, many profiles are pushed into one. So you need to be and a scrum master and a project manager and uh be a top negotiator in everything and vendor management, which used to be three positions 18, 24 months ago, and it's now all rolled into one ball into profiles which don't really seem to exist.

Christine Kahn: Yeah, I'm seeing some new roles emerge to where they're just calling it a builder, and it's kind of a mix of an engineer and a TPM and a product manager in one. What are your thoughts on those types of roles?

Jack Smith: Everybody is making stuff up on the go. It it is if you're like, okay, give me an elevator pitch in one sentence, what does an AI builder need to do? If you ask 10 different persons, 10 different people at a convention, you you will get 15 answers. Yes, they have to build AI. Well, yes, that's in the name, but what does an AI builder do? Nobody can tell you because they don't know. They're making it up on the go.

Christine Kahn: We talked about the hirers, but for people who are looking to get jobs, knowing that these AI systems exist in screening, what can they do to navigate that?

Jack Smith: That's that's a that's a million-dollar question. I've seen some hiring agencies try to do say, hey, we have this uh job opportunity. Can you customize your resume, your CV, so that it includes all the proper keywords so that you will get selected by the top of the pile? It is a very natural thing to do and almost an automatic reflex because you want to get to at least a foot in the door with a single interview. But you're you're setting yourself up to fail because you are heading towards a mismatch. You you claim that you are a specialist in things that you cannot do while you are effectively hiding the skills that you do have and might be useful. So for myself, when I have to send out my resume to a potential customer for uh a project or for um helping out left and right, I I refuse to do it anymore. I have updated my CV so many times, I have have gotten zero additional projects with that method. It just don't bother. You can always polish a tiny bit, but don't go and rewrite it with any AI tool yourself. Also, refuse that any agency rewrites your CV for you because that's not you that you are suggesting, and then both sides will be disappointed in the end.

Christine Kahn: I've been testing the Claude resume rewriter to tailor things just to see how it works. And it really needs a lot of human in the loop. I am always going back and editing it because they will pull information that's not accurate from the job that is being applied to. And I'm like, wait a minute, no, like that would be a big problem if somebody thought that I did a certain language and that's not what my focus has been. No, so it's kind of scary.

Jack Smith: I give you a good example because in in the in the early 2000s, I worked in logistics and shipping companies that had still and they still have today, mainframes for all the big bolt order processing and all the package tracking. And I listed it on my resumes as okay. I have worked with these systems, I know they exist. And one of those AI systems just made me a specialist with 20 years of experience in the mainframe field.

Christine Kahn: Oh my gosh.

Jack Smith: And if you just send that out blindly, then you you can say, Oh yeah, we saw that uh you have uh IBM mainframe specialty for 20 years. You are the person that we're looking for, and you have to tell the hiring manager, like, I'm sorry, I haven't touched those things in 20 years. But thanks to hallucinating AI, well, there that's where we are. And we have wasted everybody's time, and this is a complete mismatch.

Christine Kahn: Yeah. You know, some of the the roles I've been seeing are AI transformation lead or say, you know, just a new it almost seems like the same thing as a program manager, but it's just rebranded to what is savvy now, AI program manager. So what I would recommend to people is to look at the skills that you have and how they translate to those roles. But it's a little bit challenging sometimes to even know what to search for when you're looking to apply to things.

Jack Smith: Yeah, you kind of have to guesstimate what they're actually looking for. Because an AI integration manager, what's the actual job description? Do you need to set up an AI system? Do you have to move to an AI system? Do you have to get people acquainted and used to working with AI systems? Those are three different jobs that fall under the same umbrella. Like, what do you mean? They don't know.

Christine Kahn: Yeah. Do you think that we're gonna see more specialist roles or more generalist roles nowadays?

Jack Smith: It's it's common evolution that a generalist always survives. A specialist can be very good for a short period until the specialty dries up.

Christine Kahn: So it's more temporary.

Jack Smith: It is temporary because everybody will now need to have AI integration specialists. Well, well, once the AI is integrated, what are you gonna do? Because you might be the best AI integration specialist in the world. Well, there might be 5,000 of them, but they're only looking for 250. Now what? Of course, it's it's good to have those additional skills and use that skill set, but keep a generalist skill set as well. So keep on doing your planning, your budget, your communication. Don't throw that out for this one specific niche market unless you are ridiculously good at it and you can make enough money in the sector that you can retire in five years. Then absolutely go for it.

Christine Kahn: Yeah, I think back to when agile and scrum became popular. It was all about agile transformation. And before that, it was lean transformation. And so it's really the underlying skill set to be able to drive change.

Jack Smith: People with lean six sigma belts, are you doing today? Please tell me how is AI working for you?

Christine Kahn: One thing I was wondering is is it gonna matter that I don't have a PMI, which is Project Management Institute certification? It never stopped me from moving up in my career because I had the experience and the ability to learn on the go.

Jack Smith: The only place where I found those things interesting was twofold. One of them is if you are hiring and you have the choice between two candidates, exactly the same skill set, soft skills, hard skills, they are they're asking the same money, they have the same experience, and then one has a cert and one doesn't, there it there you can use it as an additional differentiator. You will also see, and then this is more technical, if you want to be, say, a partner for a tech company, like say Microsoft, say Oracle. If you want to have a certain level that you can be a silver, gold, platinum partner, you will need an X amount of certified people in your team on your payroll. So there you need to fill that buffer so that they can say, hey, this gold partner has this has this skill set available and we've validated it. In those two spots, yes, I can absolutely see it. Otherwise, it is limited unless, again, you go really, really, really specialized. If you have all the higher level Cisco technical certificates, then you can skip the interview because if you can pass those, you know what you're doing.

Christine Kahn: Yeah, I think it's it's just like any other return on investment situation where you have to see, is it worth my expense for this certification or this degree, say some master's or PhD compared to what the incremental improvement in the salary would be. What tips would you give people who are trying to navigate this crazy environment in hiring right now?

Jack Smith: Do not go and change yourself or present yourself as to something that you are not. I know times can be tough. I know that the hiring market is not fantastic these days, certainly not in the IT field. I see this around me. I know that my personal projects have gone down from 200% to a busy to 100% busy. So you do see it in the market, but don't go and sell yourself as something that you are not, although the urge and the temptation is absolutely there. Of course, you can you can aim high. So like I have some knowledge of this, and I'm just gonna aim high and say that I'm a specialist, go for it. Because you because you don't know what the hiring company is saying by what's a specialist. Is this somebody that knows how the menu works, or is this somebody that can design this on the back of a napkin from scratch?

Christine Kahn: Yeah, good advice. And I think now more than ever, leveraging our networks and having that human connection is going to be the big differentiator in getting access to those roles because oftentimes things get listed internally, but not yet externally. And if you know somebody, then you can have a chance to apply sooner than it even becomes public.

Jack Smith: That is one way to do if you can if you can do it. And I've had some experience in that. And yes, you can some well, you can cut out the middleman that it's not posted on any uh job hunting website or goes through a headhunter or is posted on LinkedIn. However, even when headhunters say I have exclusive access to this position and I'm the only one who had it, you have three, four other headhunters that contact you anyway within the next two days. So you will pass a certain first screening, but second and third is always there. It is not like, oh, I know a buddy, he'll be good. You can just hire him straight off the street. I don't see that happening all anymore.

Christine Kahn: Another tip I recently learned is if you're applying, you want to go directly to the hiring company's website so you can get into their data system as soon as possible. If you go through an agency or even LinkedIn through their EC hire, it's a little bit slower process to get where the data needs to be.

Jack Smith: Yeah. Well, it it depends on how the data is treated, and you don't know this upfront. Entire um the LinkedIn system or an agency, they can throw it through an AI filter with their hunt for keywords, and then you don't know. But sadly, the same goes directly for the hiring company because they you don't know if they prioritize the website list or if they look at it secondly when the other things don't come up, because a bit of well, people are now applying via multiple ways if they see something that they really want to get or at least have a shot at. Talking to some headhunters where, say, 24 months ago you would they would post a job out in the field and two of their colleagues would send it to their cousin or their brother and they would get some uh job applications in plus three, four from the market. Today, if something is posted on, say, LinkedIn, they have 500 applications. It is extremely difficult to stand out. So if you have the luck that they first look at the internal ones to the website, sure, it might help. If it's ignored and you don't know this upfront, well, at least you've tried.

Christine Kahn: I saw something the other day where a company was skipping the resume review and asking people to create an AI agent as a challenge and submit that as their entry to get the job. It's very interesting, and I'm not sure how I feel about it yet.

Jack Smith: You just go to a cloth and say, make me an AI agent. I mean, yeah, it's easy to do, but to expect it it proves absolutely nothing because something with AI, which is then scrutinized by AI, and in the end, nobody gets hired. That's exactly what I started with.

Christine Kahn: Yeah, it's the same problem in a different form, but you had to spin out a little more effort to do it this time around.

Jack Smith: Yeah, okay. You need to buy some tokens.

Christine Kahn: Tell us about your podcast and how this became your project, and if you have any other fun projects going on you want to share about.

Jack Smith: I have a few, and uh, sometimes I have too many. But no, uh the podcast started out because I'm doing this now for over 25 years in IT, everything with the PowerPlux. Okay, I want to share my knowledge and partly my misery, and how do how can I prevent other folks from having the same steep learning curve that I had? So my magnificent idea was that hey, I'll write the book one once I'm semi-retired, and then I'll just see how that goes. And then somebody who was smarter and younger than me said, Well, why don't you just start a podcast? I've already been streaming some stuff with old computers, uh, look at my background, for the the last five or ten years. So I had the experience, okay, sure, let's get this thing going. I have stories of my own from my network. People can come to me and uh tell them the story. So we're not focusing in the podcast on the blame game. We're focusing on the what can we learn from this? What can we do to prevent this in the future? And it can go from a technical decision to a business decision to a planning decision, and it is sharing well, partly misery to make it fun and tongue-in-cheek, but also to share the knowledge how we're doing this, and and we are now in our second season. We started this about um April, May of last year, and we're uh now publishing two to two to three episodes a month. We don't have a really fixed schedule, we don't want to stress, we want to go for quality over quantity, but I do feel that we're getting there.

Christine Kahn: Yeah, I love how relatable the topics are. I listened to a few, and you know, a lot of people who are in tech heads down, they get it. And being able to go from that frustration to okay, well, what do I learn from this is really important. So I'm glad that you're putting that content out there.

Jack Smith: Yes, indeed. And um, otherwise, well, as as I said with old computers, I'm active in something called the demo scene since 1991, which is a very long time ago, where we do, say, digital computer art, that's how we sell it today, uh, on old computers and new computers. Say, imagine you have a cube running on a screen that is cool. If you make it shiny, that is cooler, and we try to do it real time, so it's like a non-interactive movie that is uh generated. There's an entire internet out there that will teach you, and I can make an entire podcast series, there are podcast series on the topic anyway. So I'm not gonna delve deeper into that. But if you look it up and have some fun with old and new computers, that is also part of things that I do, and they still have power plugs. I'm stuck with those.

Christine Kahn: Very cool. Where can people find you if they want to connect and potentially partner with you?

Jack Smith: The podcast is it horrorstories.eu. EU because we are based in Europe, and if you type IT horror stories with Jack Smith into any favorite search engine, you will find the website. You can find the podcast on the usual platform, so that is uh Spotify, Apple, YouTube, Deezer, and everything that feeds from that. We have some social media as well. We focus on the more techy ones, so uh LinkedIn, Mastodon, and Blue Sky, although we also have almost call them legacy, but that's kind of what they are. Facebook and Instagram profiles for those that are not into the uh more alternative social medias.

Christine Kahn: Wonderful. Thank you so much, Jack.

Jack Smith: Happy to be here, Christine. Thanks for having me.

Christine Kahn: To everyone listening, if this resonated, subscribe and share it with someone who needs it. I'm Christine Kahn, and this is Dreams and Delivery.

Christine Kahn: Welcome to Dreams and Delivery, a podcast for tech professionals. Real stories from people who deliver at work and dream beyond it. I'm your host, Christine Kahn. By day, I'm a staff technical program manager in big tech. By night, I'm a musician and a sound bath meditation practitioner. This is a conversation about what it actually means to call yourself a builder in this age of AI agents, why judgment and tastes turn out to be the hard part instead of production, and how the things you care about outside of work end up shaping what you choose to build. Andrew Cunliffe is a senior staff product designer at Intuit, leading design on the AIHI expert platform inside QuickBooks and TurboTax. Before Intuit, he was in startups at this 82nd airborne, an interesting runway into a career spent turning complex requirements into interfaces opinionated people can align on. Outside of work, he's building his own fleet of AI tools, Raven MCP, high-level, a fully designed jujitsu brand, and a business platform and an AI-narrated daily show, treating nights and weekends like a second full-time job. Andrew, welcome. It's so nice to see you.

Andrew Cunliffe: Yeah. Hey, thanks so much for having me. I'm stoked to be here.

Christine Kahn: So tell me, you went from working in the 82nd Airborne to startups and then eight years at Intuit. How did that path happen?

Andrew Cunliffe: Yeah, I know. It's like kind of a weird path. So like most designers, they either went to art school or you know, some kind of media school or something like that. I'm born and raised in Rin County, just north of San Francisco. It's like where I live now. I actually live a mile from where I grew up.

Christine Kahn: Nice.

Andrew Cunliffe: And I there's a lot of people in my family who had been in the military. My dad went to the Naval Academy. My half-brother spent 30 years in the army in special operations. And so when it was like time for me to get out of high school and stuff, like the only thing I ever really knew that I wanted to do was join the military. So I wanted to do that. And the the way to actually like pick and get a cool place, the army was like, yeah, if hey, if you want to be airborne and you want to be in the infantry, no problem. So I chose that. And I chose Fort Bragg, the 82nd Airborne, you know, storied division uh that jumped into all over Europe, Italy, Normandy, Ad-Day. Just really storied division. So it was really cool to be part of that. And while I was in, I did two tours to Iraq. I joined when I was 17 and like turned 18 right before I went off to basic training. Turned 19 in Iraq during the invasion. Did my four years, and I was like, yeah, I don't think this is what I want to do for the rest of my life, at least at this point in my life. I was 22 years old. You know, all my friends were like in college, kind of having fun, back home, living their life, et cetera, or graduating college. And so I got out and went to college, but I had no idea what, you know, and you have to pick a major up front. You can't just like find out. So I was like, well, my mom's in finance, my dad's an engineer. I don't really know if I want to do either of those, but I gotta pick something, I guess, along those lines. So I was really into MMA at the time, and I mean still am, but Chuck Liddell was the champion, uh, light heavyweight champion of the UFC and like a like my favorite fighter. And he had an accounting degree from Cal Poly. So I was just like, all right, I'm just gonna choose accounting because Chuck has accounting. Uh and I went to school for that. I didn't like accounting, so I switched to finance, got out, got done with school, did like a little internship in uh for a small hedge fund here. And I was like, man, I don't really like this either. And a friend of mine, he was working at Wells Fargo at the time was like, hey, my brother's like building apps for companies, and he's like really, he doesn't want to do the front end side, and he like hates talking to the clients and stuff. So why don't you go see if it's a match? And so then that's kind of how I got started. And we started building stuff for all these different companies across the United States, some in Japan and some in Australia. And then it was kind of like, you know, the thing about freelance is you're either like super busy and you're like, how do I stay on all these deadlines all the time? So I'm trying to deliver for three clients. And then it's like, I have no clients and no money coming in. Like, when's that gonna start? So it was like, okay, it's time for a full-time job. And I started on the engineering side, and I was like, yeah, again, I've like, I don't know how many times I've pivoted, but I've been, I was like, ah, that's not for me. So I went to design and that's where I've kind of settled in, but I've always like not fit the box for product designer because I like to get my hands dirty in the code too. And also, like, you know, I I went to school for business. I understand business metrics and like how products work and how they're marketed and all that kind of stuff. So I like to be involved in that as much as possible too. But really, like the the end all be all is design. If you don't have a well-designed product, you're not gonna have customers.

Christine Kahn: Yeah.

Andrew Cunliffe: So that's mainly where I've you know had the biggest impact.

Christine Kahn: Yeah, really cool background. Just love hearing your evolution throughout your journey and in the workspace. Would you always consider yourself a builder, even prior to the whole AI builder craze that's going on now?

Andrew Cunliffe: Yeah. I mean, like we can kind of talk about, you know, what I think about the word builder too. But one of the things I'm working on for my portfolio, I've been really into making like cinematic scrolling websites lately, especially ones showing timelines. Like I did one for the 9-11 Turbo, like its whole 50-year, like every model, you're just like walking through different period correct garages. Just something I did on the side because I was curious and want to see if I could do it and it would be fun. But like going back to even like middle school, I'm a 90s kid, middle school, early high school, like building GeoCity sites with HTML and like you know, inline styles. And then also, you know, I used to play a lot of games like Half-Life 2 and different mods for Half-Life 2, and I would make skins inside of Photoshop for like different uniforms and weapons and things like that, and then put them on the internet and the forums for like people to download. So I've always been doing stuff like that, you know, and like if it's not in a computer, which I've spent a ton of time, then it's yeah, with cars. Like I had a 1970 Dodge Challenger that was my first car, and I tore it apart and built all kinds of you know things. Like I can't, I just can't leave stuff alone. I always have to change it. I'm always trying to see how things work, why they work. I make them work better, at least what I think is better, which you know sometimes is very subjective.

Christine Kahn: Yeah, I love that. You're taking me back to GeoCities days, but also, you know, even myself, I tinkered with building my first computer back in the day. And it's really cool to have access to new tools now where it's enabling us to kind of dabble in new things and contribute in ways that we didn't typically think to. I'd love to hear your thoughts on what you think the AI builder is and what does it mean to you?

Andrew Cunliffe: Yeah, totally. I mean, so we get that, you know, like you see that word kind of thrown around a lot. I think I mean and we probably talk about taste too. I see a lot of design leaders saying taste, which is something like I don't feel like we've talked about as much previously as as recently. It was always about like craft, and craft is there, and like taste is part of craft, I guess. But on the builder side of things, it's kind of interesting to me because there's some companies I've heard that literally gauge their employees' output on like how many tokens they've spent, right? On AI tools. But just because you're spending tokens doesn't mean you're building the right thing, right? So, you know, that's that's a piece of it. And then the other piece is like the mindset. Like I I've always had this mindset where I'm curious things can be different, and then I like to solve problems, which I think like designers are problem solvers in general. You know, I think a lot of people in the product space generally are problem solvers, they just kind of solve different problems in different ways. But to me, a builder is someone who is super curious. They want to push the limits and see what they can build. And then also when they see a problem, they're able to identify like, is this worth building a solution for or not? Because then, you know, if you're not building for a solution, are you actually building anything? Like, I guess you are, but maybe not really. That's why the term is like kind of funny to me. You know, it's like, did you just build something or did you build something worthwhile? You know, maybe that comes into like the taste and product sense piece of it as well. But there's a lot of people building stuff out there, and that's like I I know you read the post that I wrote on Substack recently. Yeah. But definitely like as designers too, I feel like we have this moral obligation to kind of like help people figure out what to build and how to build it. Because that's generally what a designer does. We're like, okay, first we have this business problem or product has come to us with this customer problem. We need to validate that problem first and then figure out how to solve it. And sometimes you might actually have a solution without a problem, but you also need to figure out if that solution does solve that problem well or what problems it even solves.

Christine Kahn: Yeah, you're making me think of a line that I saw on your Substack article about judgment and taste and how judgment without accountability is just output. And I'd love to hear more on your thoughts there.

Andrew Cunliffe: Yeah, I'm it, you know, it kind of comes back to the same thing like just spending tokens, right? It's like, okay, I can just spin something up and put it out there. It's like, hey guys, look what I made, you know? But does it actually like solve a problem? I don't know. And then, you know, on the accountability piece, it's like, hey, I'm a designer. Now I can just spin up anything with Claude Code. But if I'm not, you know, using modern engineering best practices, like what's my stack? You know, am I using Next.js? Like, do I have proper Tailwind classes? Or am I just spinning up some random HTML and CSS, you know, to go out there and it's like not something that's extensible and doesn't have great components in it and things like that. You know, it's like who's accountable for that? Like it might be absolutely beautiful if a designer built it, but from an engineering standpoint, like that code was cheap, but the engineering is expensive. And it's the same thing where, you know, there's all these engineers potentially, or even people that aren't engineers that can spin up, you know, code with good modern frameworks. But what does it look like? Like, you know, how how do people click through it? And I talk about on there, if you if you extrapolate like how all the misclicks or, you know, when people don't understand what the page is about, and you think about all the time we spend on our devices, like how many days of our lives are spent with poor UX throughout, you know, our lives, right? So we we have way more time now, or we should, in order to work on the details and like, you know, really execution has always been the bottleneck. So strategy was compressed, and then the finishing touches were compressed as well. But now that execution is so much easier, like engineering is way less of a bottleneck because one engineer can choreograph, you know, however many agents to do stuff, right? And check their work. Yeah. You know, we should really be spending the time on is this the right strategy? And also on the finishing touches. And with that, when we are spending time on that strategy, we should be able to pivot really quickly too. Because it's like, okay, this isn't throwaway code anymore. That's like this huge waste of time because we can do it so quickly.

Christine Kahn: Yeah, well, you were saying about you know, anyone can build anything now. So say you you have engineering or product coming to you with prototypes, but it doesn't have any of this design built into it. I was talking to a friend of mine who's a product manager and asked her, if you could do your AI adoption differently, if you could start over, what would you do? And she said, I wish we had put in our design framework into all of the agents that we have, because people are coming to her with their prototypes, but it doesn't at all look like anything usable that she could go to market with. So I think being strategic and including design from the start would save some effort down the line.

Andrew Cunliffe: Yeah. And I mean that's like another accountability piece, to be honest, on design. Like we need to be accountable to make sure that those kind of frameworks and things are available to our partners, right? So I I've done some of that stuff added into it, like on the IDS side. I mean, I don't, I'm not in the Intuit Design System team, but I have built some things for my team to use so that they are using actual IDS components and pulling them from our actual repos, you know, because we have MCPs and stuff that can, you know, that connect to all that stuff. And I think I guess maybe that comes back to the builder mindset too. There's like two other points there where it's one, instead of just building something, think about how it should be built and what you need up front, because that will influence how you build it, right? Like, how do I get you know the design system components in here? But fundamentally, even if you don't do that, I I'm always happy when a PM or non-designer or anyone else comes and brings me a prototype because it's so much easier to understand their thinking than something that's just in a PRD.

Christine Kahn: True. You know?

Andrew Cunliffe: So it's like you're looking at words and you're both trying to interpret some vision in someone's head, you know? Um and it doesn't necessarily need to be a vision because design has to figure that out, but even just the basic kind of requirements laid out in a visual manner, because I mean we're all visual beings, so it really, really helps start conversations and frame them. So totally cool and fine with that. I think one of the biggest things I'm running into right now are people that like don't really want to adopt AI and don't really want to change their mind. And I think that's a bit of a friction point. You know, I assume it was the same when the internet came along and people didn't want to do that either. They didn't want to write emails. But I I'm definitely finding that that's a big, a big friction point as well.

Christine Kahn: Yeah, that that's interesting. And I would think even from a consumer standpoint, people using the tools and how they see chat agents and how that presents. But as you're building, how do you know when to trust the agent's output versus when to step in? That's probably one of the friction points where people are reluctant to just trust the AI.

Andrew Cunliffe: Yeah. And it, you know, I mean, it comes in various forms, right? So, like in terms of coding output, I have a whole, and you can actually get a lot of this stuff on my on my website. I have a whole site just like dedicated to my method of using AI, but I'm constantly looking to see how I can be more efficient, more accurate, et cetera, with quality output. So one of them is like doing the work up front, you know. And I mean, I personally like to watch YouTube kind of instructional videos on how to do this stuff, but you can also have your agents just do it too. Like he can say, hey, Claude, go watch YouTube videos on X, Y, and Z and then come back and tell me how we should do this, right? And he could ask it for citations on like where to go watch it in the video so that you can go and see, you know, where it's at so all of its stuff is defensible, right? So I do things like that all the time. So, you know, when I go to send up a new project, whether it's, you know, uh an iOS app and it's in Swift or it's a web app, it's an X.js, one of the things up front is every time I kick off a project, the agent has to do a spec using rules and skills and my knowledge graph that has, okay, here's how to do all this stuff with, you know, modern engineering best practices, right? Because there's hundreds of books. And I mean, that's how like a lot of these models have been trained is literally scanning books, you know, into these models. And so I'm essentially doing the same exact thing, just you know, locally and it's saved in a markdown file on my knowledge graph. So that's like on the engineering side, that's how I have it. And then as part of my design tool, Raven MCP, I have a taste engine in there that's actually working on training a small local model on my home hardware. But even if you just download it and connect it, every time we kick off a project, it'll go through an interview on how do you want this to look? Who is the customer? Do you have any examples to share of what it should look like, et cetera, to try and build that taste up front? Because it's way better to get this stuff going up front so that there's a vision, like, okay, everything is spec'd out. You know, here's how you describe it visually, here's who it should talk to, the kind of voice it should have. It should, you know, be a light version of Linear's design system with, you know, one accent color or something like that. So you get all that information up front, provides way more context. Then the output is way more defensible and there's way less work for you to do on the back end. And you can kind of justify all of that because you did all the work up front.

Christine Kahn: Yeah, it's funny. Raven MCP is how I ended up reaching out to you because I saw that you made it available open source for people to use as their own design system. And immediately I had it audit my website that I built and it had really good recommendations and even identified things in the flow itself where I had some duplicate information on different pages in my site. And so I love that you've made this available for people to utilize in their own workflows. Can you tell us more on your thinking of the strategy going open source versus keeping it private and monetizing this sort of thing?

Andrew Cunliffe: Yeah. So on the open source piece, you know, like I kind of went over earlier, I have like a very non-standard design background, right? And so when I was like building, you know, doing freelance work and building stuff for clients, like the person I was working with, we were using like every open source library possible, you know, because we were both like coming up. We didn't have a ton of money to spend. And he lived in New York, I lived in San Francisco. So it's not like we had a ton of extra money either. It's like the two most expensive cities in the United States. So we're using like every open source thing possible and learning so much from doing it, you know, things like Twitter Bootstrap. There's so many frameworks out there that that we use, free icons sets and stuff like that. And so I was like, hey, whenever I get to a point where I can do this, I want to give back to people. And so that's like one of the big ones for me. I always wanted to do that. I always wanted to make something open source that people actually wanted to use and provided a good level of utility. And then the other piece is really some of the stuff that I talked about in my recent post on Substack. And that's like this moral obligation for designers to really help people, you know, get quality stuff out there. Because one, the stuff's gonna come out, you know, whether or not we do help. And then it's either A, gonna have a poor effect on people because they're gonna spend time with bad UX and all these other things, or it might be a really, really, really good idea what this person is doing. But because the design is off in some way or another, or it looks like AI slop, people are just gonna disregard it. So I really wanted to help people get good ideas out there and, you know, get them with a high level of polish. And then as I was using it myself, I've kept evolving it. And it's kind of like why another design tool, right? Well, there's some really good ones. You know, everyone uses Figma. It's a desktop app. It's also super slow to load things and you're drawing things on a canvas, right? So there's an MCP and they have agents on the canvas. Not really the wordflow I like to use. I use Figma when I want to go like tune some really high fidelity like visual details on stuff and kind of do like animation keyframes to feed a claw. And then you have like amazing new products like paper and Dessin. They're really cool, they actually like take your own code base in, or they actually build it right there in code and you can pull it right out. And they have cool generative capabilities as well. You know, they of course all cost money. And so for me though, I was like, hey, I don't need another, you know, and there's like old reliable sketches out there, and it actually runs locally so you don't have the speed problems with Figma. But for me, I was like, I don't want another canvas, you know, like I don't want to have to open things, have more files. I just want to work right in my app. So that's why I built it, and that's kind of like why it's different from, say, a paper or a Destin or a Figma or whatever. You know, it's got design panels that. Can use and all that sort of stuff. But then to your point, you can also use it to audit all these things like accessibility and voice and tone and give you suggestions. It'll create a design system for you. Also, now there's you know functions. It's got over a hundred tools now. I started with like 12 or 15, now it's got over 100.

Christine Kahn: Nice.

Andrew Cunliffe: Yeah, it'll like audit your designs and be like, hey, you're not using this component correctly if you have a component library, you know? And it's pretty much got all the functionality, not pretty much. I mean, I would say it's got like 75% of the functionality of your normal design tool now rendered in the canvas canvas, now like rendered in a browser. So you can just move stuff around there. I could even show that real quick too.

Christine Kahn: Yeah, yeah. No, uh, I'd love if you could show the demo mode that was on your website too. Cause I see that as a really good way for people to learn about design. Because I was clicking around and just learning about the different components and what you can do with them.

Andrew Cunliffe: This one's let me share. Okay, here we go. I think this is the right one. Can you see my screen? That's my portfolio. All right, cool. Let me just switch to uh my screen. All right, so this is my portfolio, and um it in itself is wildly controversial, I think. But also I make it so you can now design, redesign my portfolio. So in line. Um so I have Raven open right here. Any, you know, you can close it, open it. There's a tour as well. But just like any design tool, if I want to just, you know, click in here and see like, you know, what should we change this to? Um, and then I can change the size and all kinds of stuff over here. And then um here I can just drag it and you can just see what that looks like uh live. You know, so previously you would have to go and tell your agent, like, hey, uh move this up above this thing. You know, and that would be like one turn, or you try to package it all together and you know, it it wouldn't get it. But now you can just, you know, move it and see it. And of course, these are bad examples, but you can also give specific instructions right here, and then you hit, you know, this when you use it yourself, we'll say send to agent, not send three changes. Um, but this will send it to your agent, and then your agent will go ahead and make all those changes just as you set them up.

Christine Kahn: Um so you know, it's just the learning element I was alluding to is here, say I am a non-designer. There are probably elements here I wouldn't even think to prompt my Claude to change versus now I'm learning, oh, actually that's what that is, and here's what I actually want it to look like, and you refine it from there.

Andrew Cunliffe: Yeah, and you know, these are things like even for someone like me, these, you know, these are all like CSS classes, and there's been so many added over the years. Sometimes I forget what's what. And so it's even good for me to see them as well. Um, and when you have different elements that have siblings too, you can select them all and change both at the same time, um, you know, making that easy as well. So, I mean, I just released this, so uh it's still a work in progress. But coming back to your question about open source versus monetization, so like I said, I always wanted to keep one open source, right? But then I have another one. Raven's got a big brother now that's kind of evolved out of it that I'm working on that's gonna be more geared towards teams. Cool. You know, so not I think a lot of the the design tools in the space are like really funny to have all the functionality to like kind of beat each other. And a lot of them, you know, pretty much all of them have a canvas still, um, even web-based ones, like a really cool animation app is Jitter, and it's still, you know, canvas-based, which works for a lot of designers and a lot of people. But also, you know, there's a lot, I think there's a lot of hybrid people out there now that are designers and engineers, and they just want to work with what's on screen. Because you're still going to be translating, even if it's rendering in a canvas and HTML, CSS, React, et cetera, it's still not the actual app itself. So I want to have somebody can do that. And then team functionality too. So, you know, a big problem always is are design tokens being followed? Like, are they being hard-coded or are they actually pulling on the right ones? Or like, is something being used that's not, you know, whatever the component is supposed to be, whether, you know, it's like a drawer or something. And like, is a drawer being used for use case that's not supposed to be used? Well, the the design team or whoever's in charge of that, back to the whole accountability piece. Like, they should be held accountable. So there's, you know, this this new, it's called Morvin, M-O-R-V-E-N. It's a Scottish word for mountain. And it's basically, you know, the mountain you don't have to climb is like all these alignments and things and like tracking down, okay, what component do they use? Do they use the right colors? Do they use the right tokens? Because it does all that for you. You know, I mean, that's the plan. That's what's I've been working on too. And then it's accountability in designers too. Like engineers could say, hey, look, I built this thing. You don't have a use case, you don't have a component that fits this, and I need one right now. And then it'll help you prioritize that stuff too.

Christine Kahn: Yeah, it's almost like they can speak the same language between the engineers and the designers now.

Andrew Cunliffe: Yep.

Christine Kahn: Yeah.

Andrew Cunliffe: So a lot of times, you know, these are conversations that like happen in Slack or in meetings and stuff like that. And then that's the other thing. Like, where do you keep the decision on where, what, why, and how? And so this helps you also hold those decisions. So it's like, why should I use this component here? And it's like, oh, you should use it here because it follows, you know, these laws, and here's why we made those decisions, you know, which is something that's like tribal knowledge that constantly gets lost.

Christine Kahn: Yeah, so true. Especially in wider teams and you're working distributed. Beyond Raven, what are you also building right now? I seen high level and an AI-narrated daily show.

Andrew Cunliffe: Yeah. So AI by AI Daily was a cool experiment. Uh I ended up like stopping to do that because it's super expensive. But basically, I wanted, this is another like just builder mentality. I wanted to see what I could do, right? So I wanted to say, okay, can AI completely research daily AI news, right? Write a script for it, then create the video as well. And so it had an AI avatar. Her name was R, and she had like a British voice. And so she would narrate the whole thing, and then it would, you know, cut up the whole video using remote. And so there was like video from Wikipedia Commons and like video of the articles and things like that. I didn't get a huge amount of traction, you know. I mean, like most videos had, I don't know, they have like 20 views or something like that. There's so many people making content out there these days, you know. Uh, but it was just a cool experiment to do and see if I could do it. So I did that and it worked, you know. So it's something I really wanted to commit to. I could. Uh, and then yes, high level is my iOS app. So I I've for a long time I've wanted to create an iOS app. There's a lot of designers out there, like a guy like Charlie Dietz, who I've looked up to, who like has a super, super sick iOS app and you know, completely coded it by hand, etc. And it's like, well, you know, I'm a dad of two. Finally, my kids are five and seven, so I actually have way more free time than I have had over the last seven years. And they actually build stuff with AI too, especially my seven-year-old.

Christine Kahn: No way, that's yeah, yeah.

Andrew Cunliffe: Yeah, he's made an arcade uh that's runs on iOS and iPad OS that anyone in the house, as long as you're on the tailnet, connected to the tailnet, can play in. So we can have like, you know, multiplayer family games and little like different games he's made, size throwing stuff. There's like a little plain one, it's really cool.

Christine Kahn: Fun.

Andrew Cunliffe: Yeah. So uh I always wanted to have an iOS hat myself. And also I do jujitsu right now, and I've been a power lifter before, and like there's weight classes in both. So, like, you know, the last 20 years of my life, it's like my weight's going up or going down or whatever, and it's always about tracking calories. And there's probably a thousand calorie tracking apps out there, honestly. It's like super saturated. And I've tried a bunch of them, but none of them like were really geared towards athletes and more towards coaching. A lot of it was just like recording, like, here's how many calories you ate that day, you know. But mine has multi-model orchestration in it. So depending on the tier, you know, you get higher levels of frontier models. They'll literally help you plan out, and it's I try to keep it as simple as possible, too. There's like three pages in the whole app. There's just a chat, which is like your log. There, no, there's an actual log that shows like all your meals over every day. The chat's the main thing interact with. And then there's a weekly planner and settings, and that's it. So, like four places. And the weekly planner, it usually only touches like once a week. You usually you just plan out your whole week and you know, like people have lives. So you can be like, hey, on Saturday, I'm going to a wedding. Like, I'm not going to be following the diet. So I need you to like cut extra calories other days and it'll meal prep for you and be like, okay, here's your whole grocery list. And so one of my friends was using it and he was like, Hey, it'd be great if I could just, you know, point this at a grocery store's API. And there's really no good ones out there. So the solution for that was it'll create a grocery list for you. You copy it, open the app, whether it's Instacart, whatever, their AI agent, and just paste the list in there. And it'll just go and add all of it to your cart. So, you know, plans out your week like that based on your goals. And then, you know, you can log it via text, via type, via picture. And again, there's a lot of apps that do that, but it's also a lot of times they're approximations or it's community-entered stuff, you know, whereas mine actually talks to multiple APIs like the USDA food source API. So it's very defensible data on the calories instead of, oh, someone just, you know, estimated this, et cetera. You know?

Christine Kahn: Wow. That's super cool. And really niche for someone who's looking for that experience. I love that you've made this. Well, what is it called again? High level. High level.

Andrew Cunliffe: H-I-G-H-L-V-L. Yeah, and I'm actually planning on with that one, scaling it to different sports and other things. Like high level is more like a brand. And this is the, you know, the diet calorie tracking app. But I think there's a lot of opportunities out there for different sports. And so you, you know, there's a lot of people who do it for lifting, like they have AI-powered workout programs and stuff like that. But as the models get smarter and they can actually coach and can critique more via vision and other things, we're gonna see it doing that live.

Christine Kahn: Uh, very cool. I meant to ask earlier when you were talking about the the AI generated show that you were experimenting with, where would taste fall in that sort of thing where a lot of it's just automated? Would it be plugged into the original infrastructure or would you like check in on it every so often?

Andrew Cunliffe: Yeah. So that one, the taste is really yeah, up front again, right? And so you really kind of want to nail one. I don't think I ever actually nailed one. I think I probably got to like 70%, to be honest. Because it's kind of a hard problem to solve, right? Where it's like I have to have it generate everything and I can't do anything on it at all. And also I was doing that back in, it's crazy how fast stuff has evolved because I was doing that back in like April and May. And I think there was, you know, not that many frameworks available. Like Remotion was like the only one. And now there's like so many more things that have come out, or at least I didn't know about any more and I couldn't find any more at the time. But really, the taste there is like, okay, how do you set up the video? Obviously, the avatar. I worked a ton of time on the avatar. I worked on it with my daughter. She really was like interested in doing that with me. Um, so we worked on that together, getting the voice right, getting the tone right, the look, et cetera. Then, you know, it's like, okay, how should the flow go? Like, how is the intro? And then a kind of template for, you know, how the run-of show goes. And of course, I had Claude watch numerous, you know, YouTube videos with where they have a ton of followers on the channel and kind of borrow their best practices. So, like, when to cut, and like, you know, moving the avatar down to a smaller circle down here, and then you know, taking over full screen at certain points. And so there's like these different cues, you know, and then okay, what should, you know, where do we kind of have colored and different typography assets as part of the template as well? So all kinds of things like that, you know?

Christine Kahn: Yeah, interesting. And even if even if you're no longer doing it, there's still maybe a lot of learnings there that you could harness for something else, I would think.

Andrew Cunliffe: Yeah. Yeah. I mean, there's so much stuff that I've done that have been just total experiments and I've just wasted like hundreds of dollars on in tokens that I've learned a ton of stuff from, though. And like that's been really kind of the journey. I think even though I didn't monetize it, and in fact, I lost money on it, I lot I've, you know, learned enough from it that it's just gonna carry me forward in other places.

Christine Kahn: Yeah, I think it's so cool how you started out the 82nd, and now you have your own agents, like almost your own fleet of AI. So it feels like a full circle from your where your career started and where you're at now. But uh for those who are starting their UX career, what tips would you give them in this new environment with AI in the mix?

Andrew Cunliffe: Yeah, I mean, number one, be super curious, right? Like that's so the biggest difference. I I feel like I hadn't really evolved my tool set that much over the last few years is like basically incremental here and there, because a lot of the stuff was the same, you know? It was like, okay, I'm getting faster at Figma, like, you know, 20% faster, 10% faster, whatever, every quarter, every year, something like that. You know, better at doing user interviews and things like that. But there were there haven't been like a ton of new tools, at least that I was seeing until we really got a hold of AI. And like this is how new I am to AI, too. So I got Cloud Code in April and it's now almost August. And in that time, I have built and released my own design tool. I have an app in the App Store, I have another one in the Google Play Store that's waiting to get approved, like done all this stuff. That's how fast you can do it. And that's someone who's working a full-time job and has two kids. So if you're just getting into this, like beg, borrow, and steal anything you can in order to get token access. And uh, you know, go out there and, you know, build stuff, make stuff real. Like you can make whatever you want if you have the time and unfortunately the money because of tokens, you know. But um, that would be my biggest thing is learn all of the things you need to know, like UX best practices, really focus on your visual design because that's something where it's always going to be subjective. It's almost the number one thing people react to. Even like any design hiring manager, that's the first thing they look at because it's the easiest thing to react to. You know, like how's your spacing? How is your typography? I mean, typography is like 90% of design, right? So yeah, I would be definitely focused on those core things and then really pushing the limits on the AI stuff. And I would say try to be as much of a generalist as possible in terms of design versus engineering. If you can do both really well, like the whole design engineer role now is really taking over a lot. Like I'm pushing PRs. I pushed two PRs in the last two weeks, you know, at like the senior staff level. And so if you're a you know, a junior designer coming in and you're like really in the weeds of tactical delivery all the time. I think if you can push PRs and take that off of one, take it off your engineer's plate, and two, champion that for your design org, those are things that will really set you apart.

Christine Kahn: Awesome. Well, thanks so much, Andrew. Really great hearing your stories and all the tips. And definitely we'll share all the links to the different tools that you spoke about today. Cool.

Andrew Cunliffe: Thanks so much for having me. I could honestly talk about this stuff for like hours on end.

Christine Kahn: To everyone listening, if this resonated, subscribe and share it with someone who needs it. I'm Christine Kahn, and this is Dreams and Delivery.