{"id":35892,"date":"2026-10-28T12:55:48","date_gmt":"2026-10-28T16:55:48","guid":{"rendered":"https:\/\/www.wellable.co\/blog\/?p=35892"},"modified":"2026-10-29T04:43:50","modified_gmt":"2026-10-29T08:43:50","slug":"richard-lee-ai-team-size-lean-teams-career-growth","status":"publish","type":"post","link":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/","title":{"rendered":"How AI Is Reshaping Team Capabilities with Richard Lee"},"content":{"rendered":"\n<p class=\"wp-block-paragraph\">In this week&#8217;s episode, Nick sits down with longtime friend, Richard Lee, founder of fintech startup Domeo and former Goldman Sachs and Capital Group alum who helped scale fintech LSQ to a 2024 exit. They discuss what it takes to build a company in a post-AI world, whether customers will simply vibe code their own software, and how career growth works when teams stay small and flat.<\/p>\n\n\n\n<div class=\"video-embed\" style=\"position:relative;padding-bottom:56.25%;height:0;\">\n<iframe src=\"https:\/\/www.youtube.com\/embed\/Hd2lZAA_Uro?si=4M5nrd0qA4pbrc2o\" title=\"How AI Is Reshaping Team Capabilities with Richard Lee\" style=\"position:absolute;width:100%;height:100%;top:0;left:0;\" frameborder=\"0\" allow=\"accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share\" referrerpolicy=\"strict-origin-when-cross-origin\" allowfullscreen=\"\">\n <\/iframe>\n<\/div>\n\n\n\n<p class=\"wp-block-paragraph\"><\/p>\n\n\n\n<div class=\"row justify-content-between\">\n<div class=\"cs-btn-light text-center mb-4 col-12 col-md-6 pr-md-4\">\n <a class=\"cs-button d-flex align-items-center justify-content-center w-100\" href=\"https:\/\/podcasts.apple.com\/us\/podcast\/how-ai-is-reshaping-team-capabilities-with-richard-lee\/id1869414001?i=1000798527640\" target=\"_blank\" style=\"gap: 8px\">\n\n<img decoding=\"async\" src=\"https:\/\/www.wellable.co\/blog\/wp-content\/uploads\/2026\/03\/Apple-Podcasts-logo.png\" alt=\"Apple podcast\" loading=\"lazy\" class=\"h-auto\" style=\"width: 24px\">\n\n<span style=\"font-size: 20px\">Listen on Apple Podcasts<\/span>\n<\/a>\n<\/div>\n\n<div class=\"cs-btn-light text-center mb-4 col-12 col-md-6 pl-md-4\">\n <a class=\"cs-button d-flex align-items-center justify-content-center gap-3 w-100\" href=\"https:\/\/open.spotify.com\/episode\/2ZXlv9bT0R2DoAjfnVR6Ey?si=uUOIcYgNSGOOY1s5J-Z5PQ\" target=\"_blank\" style=\"gap: 8px\">\n\n<img decoding=\"async\" src=\"https:\/\/www.wellable.co\/blog\/wp-content\/uploads\/2026\/03\/Spotify_White_Logo.png\" alt=\"Apple podcast\" loading=\"lazy\" class=\"h-auto pr\" style=\"width: 24px\">\n<span style=\"font-size: 20px\">Listen on Spotify<\/span>\n\n<\/a>\n<\/div>\n<\/div>\n\n\n\n<p class=\"wp-block-paragraph\"><\/p>\n\n\n<div style=\"border: 1px solid rgb(0 0 0 \/ 0.1); padding: 25px 25px 10px; border-radius: 8px; box-shadow: 0 4px 6px -1px rgb(0 0 0 \/ 0.1), 0 2px 4px -2px rgb(0 0 0 \/ 0.1);\">\n<h3 id=\"h-pressed-for-time-here-s-a-quick-summary\" class=\"wp-block-heading nitoc\">Pressed for time? Here are the key takeaways:<\/h3>\n<ul>\n<li><span class=\"ytAttributedStringLinkInheritColor\" dir=\"auto\">Richard estimates his seven-person AI-native team is about 10X more productive than the 40-person team that built a similar product a decade ago <\/span><\/li>\n<li><span class=\"ytAttributedStringLinkInheritColor\" dir=\"auto\">Software will get vibe coded, but in finance and healthcare, where the margin for error is zero, trust is still the biggest barrier <\/span><\/li>\n<li><span class=\"ytAttributedStringLinkInheritColor\" dir=\"auto\">In a world of AI abundance, taste, design, and the human touch are what set companies apart <\/span><\/li>\n<li><span class=\"ytAttributedStringLinkInheritColor\" dir=\"auto\">Most CFOs can&#8217;t name a software product they&#8217;re happy with (Excel aside), a trust problem that predates AI <\/span><\/li>\n<li><span class=\"ytAttributedStringLinkInheritColor\" dir=\"auto\">Richard believes his revenue could 10X without adding headcount, while Nick notes many employees still see managing people as the clearest path to career growth<\/span><\/li>\n<\/ul>\n<\/div>\n\n\n<p class=\"wp-block-paragraph\"><\/p>\n\n\n\n<h2 class=\"wp-block-heading\" class=\"wp-block-heading\" id=\"episode-summary\">Episode Summary<\/h2>\n\n\n\n<h3 class=\"wp-block-heading\" class=\"wp-block-heading\" id=\"building-a-startup-in-a-post-ai-world-the-10x-team\">Building a Startup in a Post-AI World: The 10X Team<\/h3>\n\n\n\n<p class=\"wp-block-paragraph\">Richard has built a similar product twice: once at LSQ in the pre-AI era and now at Domio, which helps mid-market businesses with invoicing, payments, and collections. That gives him a rare apples-to-apples comparison. He estimates the productivity gap across design, product, and engineering at around 10X, with Domio&#8217;s team of seven building at a speed and breadth that once required about 40 people. He points to the December\u2013January release of more advanced Claude models as the moment things really shifted, and believes that in software development, most code is now being written by AI. In his view, that hasn&#8217;t replaced engineers; it has made them more productive than ever, and he expects the finance profession to follow a similar path.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><\/p>\n\n\n\n<h3 class=\"wp-block-heading\" class=\"wp-block-heading\" id=\"the-saaspocalypse-why-not-just-vibe-code-it\">The SaaSpocalypse: Why Not Just Vibe Code It?<\/h3>\n\n\n\n<p class=\"wp-block-paragraph\">Nick pressed on a question many <a href=\"https:\/\/www.wellable.co\/blog\/best-human-capital-management-software\/\" target=\"_blank\" rel=\"noreferrer noopener\">software companies<\/a> are facing: if finance or HR teams know exactly what they need, what stops them from building it themselves with AI? He added that a DIY tool doesn&#8217;t need to be better to hurt a vendor; it only needs to convince a buyer not to purchase. Richard agrees that a lot will get vibe coded, but says finance is different because accuracy is non-negotiable. &#8220;A bank cannot be off by a penny,&#8221; he said, because once trust is gone, it&#8217;s gone. Domio&#8217;s approach is to expand its &#8220;surface area&#8221; into more regulated areas such as payments and lending, focus on taste and design, and serve what he calls the &#8220;real economy&#8221;: family-run and multi-generational businesses outside the coastal tech scene, where trust in AI matters most.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><\/p>\n\n\n\n<h3 class=\"wp-block-heading\" class=\"wp-block-heading\" id=\"incumbents-the-ai-roi-gap-and-the-delete-button\">Incumbents, the AI ROI Gap, and the &#8220;Delete Button&#8221;<\/h3>\n\n\n\n<p class=\"wp-block-paragraph\">Can a company build before AI reinvent itself? Richard thinks most won&#8217;t, citing culture, unit economics, and tech debt, though some will and may come out stronger. Nick shared the story of a well-known health and wellness company that rebuilt its whole application with AI and now handles 85% of support tickets through AI, but only after a steep revenue decline forced its CEO to &#8220;hit the delete button&#8221; and start fresh. Nick contrasted that with surveys showing most executives aren&#8217;t yet seeing ROI from AI, and with examples where more output hasn&#8217;t meant more value: an AI-driven hiring process where <a href=\"https:\/\/www.wellable.co\/blog\/kat-kibben-hiring-recruiting-ai-bias-job-postings-practical-tips\/\" target=\"_blank\" rel=\"noreferrer noopener\">neither candidates nor HR seem happy<\/a>, &#8220;resume Botox&#8221; as older candidates try to appear more AI-native, and (in Nick&#8217;s own speculation) a <a href=\"https:\/\/www.wellable.co\/blog\/fitbit-air-whoop-killer-tokenmaxxing-hr-ai-metrics\/#fitbit-air-vs-whoop-a-new-challenger-enters-the-screenless-wearable-market\" target=\"_blank\" rel=\"noreferrer noopener\">Fitbit-to-Google Health transition<\/a> that has frustrated users and developers. <\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Richard brought it back to fundamentals. Most mid-market CFOs can&#8217;t name a software product they&#8217;re happy with (both agreed Excel is the exception) and he believes B2B software lost customer trust long before AI arrived. He also argued that AI-native companies have a structural cost advantage over debt-heavy, private equity-backed incumbents whose pricing is shaped by servicing that debt rather than customer value.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><\/p>\n\n\n\n<h3 class=\"wp-block-heading\" class=\"wp-block-heading\" id=\"lean-teams-flat-structures-and-career-growth\">Lean Teams, Flat Structures, and Career Growth<\/h3>\n\n\n\n<p class=\"wp-block-paragraph\">With revenue potentially able to 10X without new headcount, how do you recruit and <a href=\"https:\/\/www.wellable.co\/blog\/employee-recognition-ideas\/\" target=\"_blank\" rel=\"noreferrer noopener\">retain people<\/a>? Richard believes &#8220;A players want to be around A players,&#8221; and that the bar for an A player has never been higher. What they want hasn&#8217;t changed: autonomy, impact, decision-making, and a <a href=\"https:\/\/www.wellable.co\/blog\/how-to-improve-company-culture-in-burnout-era\/\" target=\"_blank\" rel=\"noreferrer noopener\">culture that supports their growth<\/a>. He leans toward <a href=\"https:\/\/www.wellable.co\/blog\/ai-digital-clone-middle-management-hiring\" target=\"_blank\" rel=\"noreferrer noopener\">flat, lean organizations<\/a>, saying he&#8217;s more afraid of slack and excess capacity than of under-hiring, and puts his own ideal span of control at around 10 direct reports, a number he says AI hasn&#8217;t changed.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Nick shared the tension at Wellable: many employees still see managing people as the clearest form of career development, even as AI pulls everyone, including Nick, toward individual contributor work. He also discussed Wellable&#8217;s two-day in-office hybrid policy (with attendance now averaging closer to three days), while making clear there are no plans to change it. Richard closed with his prediction: a third political party will be taken seriously in the next presidential election.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><\/p>\n\n\n\n<h2 class=\"wp-block-heading\" class=\"wp-block-heading\" id=\"frequently-asked-questions\">Frequently Asked Questions<\/h2>\n\n\n\n <section class=\"faq-section\">\n <div class=\"faq-accordion\">\n\n \n <div class=\"faq-item card card-faq\">\n <button \n            class=\"faq-question\" \n            data-target=\"faq_1\"\n            type=\"button\"\n          >\n What is an AI-native company? <span class=\"icon\"><\/span>\n <\/button>\n\n <div id=\"faq_1\" class=\"faq-answer\">\n <p>An AI-native company is one built from the ground up with AI embedded in how it develops products and runs operations, rather than adding AI to existing processes. In this episode, Richard Lee describes his seven-person fintech, Domio, as AI-native and estimates it is about 10X more productive in product development than a pre-AI team building a similar product.<\/p>\n <\/div>\n <\/div>\n\n \n <div class=\"faq-item card card-faq\">\n <button \n            class=\"faq-question\" \n            data-target=\"faq_2\"\n            type=\"button\"\n          >\n What is the \"SaaSpocalypse\"? <span class=\"icon\"><\/span>\n <\/button>\n\n <div id=\"faq_2\" class=\"faq-answer\">\n <p>The SaaSpocalypse is a term for the idea that AI could disrupt traditional software-as-a-service (SaaS) companies, because customers can increasingly &#8220;vibe code&#8221; their own tools or switch to lean, AI-native competitors. Richard believes a lot of software will be vibe coded, but says industries with zero margin for error, like finance, still depend heavily on trust and accuracy.<\/p>\n <\/div>\n <\/div>\n\n \n <div class=\"faq-item card card-faq\">\n <button \n            class=\"faq-question\" \n            data-target=\"faq_3\"\n            type=\"button\"\n          >\n How much smaller can teams be with AI? <span class=\"icon\"><\/span>\n <\/button>\n\n <div id=\"faq_3\" class=\"faq-answer\">\n <p>It varies by company and function, but Richard estimates roughly a 10X difference in productivity across design, product, and engineering, comparing his current seven-person team to a team of about 40 at his prior company. He also believes Domio&#8217;s revenue could grow 10X without adding headcount.<\/p>\n <\/div>\n <\/div>\n\n \n <div class=\"faq-item card card-faq\">\n <button \n            class=\"faq-question\" \n            data-target=\"faq_4\"\n            type=\"button\"\n          >\n Why are companies not seeing ROI from AI? <span class=\"icon\"><\/span>\n <\/button>\n\n <div id=\"faq_4\" class=\"faq-answer\">\n <p>Nick notes that many executive surveys show little measurable ROI from AI so far. Part of the challenge is that established companies face cultural, structural, and technical barriers (like tech debt) to reinventing how they work. Some companies only make deep changes when forced, such as after a major revenue drop. Wellable is seeing positive ROI, though Nick says much of that comes from &#8220;low-hanging fruit.&#8221;<\/p>\n <\/div>\n <\/div>\n\n \n <div class=\"faq-item card card-faq\">\n <button \n            class=\"faq-question\" \n            data-target=\"faq_5\"\n            type=\"button\"\n          >\n How do you offer career growth in a flat organization? <span class=\"icon\"><\/span>\n <\/button>\n\n <div id=\"faq_5\" class=\"faq-answer\">\n <p>Richard says the fundamentals still apply: give people autonomy, real impact, decision-making power, and a culture that supports their development. Nick acknowledges that many employees still equate career growth with managing people, which creates tension as AI pushes work toward individual contributors and fewer management roles.<\/p>\n <\/div>\n <\/div>\n\n \n <div class=\"faq-item card card-faq\">\n <button \n            class=\"faq-question\" \n            data-target=\"faq_6\"\n            type=\"button\"\n          >\n How many direct reports should a manager have? <span class=\"icon\"><\/span>\n <\/button>\n\n <div id=\"faq_6\" class=\"faq-answer\">\n <p>Richard&#8217;s personal ideal is about 10 direct reports, assuming they are high performers. He says that number hasn&#8217;t changed with AI, because the human element of managing people matters more than the efficiency gains AI provides.<\/p>\n <\/div>\n <\/div>\n\n \n <\/div>\n <\/section>\n\n \n\n\n\n<p class=\"wp-block-paragraph\"><\/p>\n\n\n\n<h2 class=\"wp-block-heading\" class=\"wp-block-heading\" id=\"full-episode-transcript\"><strong style=\"color: transparent; visibility: hidden; opacity: 0;\">Full Episode Transcript<\/strong><\/h2>\n\n\n\n<p class=\"wp-block-paragraph\"><\/p>\n\n\n\n <section class=\"faq-section toc-helper-accordion\">\n <div class=\"faq-accordion\">\n\n \n <div class=\"custom-accordion-item\">\n <button \n            class=\"faq-question\" \n            data-target=\"transcript_1\"\n            type=\"button\"\n          >\n <h2><span class=\"TextRun SCXW145257824 BCX0\" lang=\"EN-US\" xml:lang=\"EN-US\" data-contrast=\"none\"><span class=\"NormalTextRun SCXW145257824 BCX0\" data-ccp-parastyle=\"heading 2\">Full Episode Transcript<\/span><\/span><\/h2>\n <span class=\"icon\"><\/span>\n <\/button>\n\n <div id=\"transcript_1\" class=\"faq-answer\">\n <p><strong>Nick:<\/strong> Welcome to the Wellable Weekly Podcast, where we talk about key topics and trends at the intersection of wellbeing, technology, and HR. I&#8217;m your host, Nick. I&#8217;m with my good friend, a guy that I&#8217;ve known for a very, very long time, 20-plus years. We met in college during a study abroad, so we didn&#8217;t go to the same school, but from there we visited each other and stayed in contact. We were roommates for a not-so-brief time here in Boston. I&#8217;ve known him so well that it&#8217;s hard for me to give the intro, but he&#8217;ll talk about his work experience. He&#8217;s an awesome person. As you get older and you have kids and all that stuff, life is so busy, and I find it hard to hang out with the people you really care about, so your list gets really short. He&#8217;s one of those people for me. We were literally just talking about trying to find time to take a trip together and see each other. Richard Lee, welcome to the podcast.<\/p>\n<p><strong>Richard:<\/strong> Appreciate it. Should I go by Nick or should I go by Nitin?<\/p>\n<p><strong>Nick:<\/strong> Go by Nick. Going old school here.<\/p>\n<p><strong>Richard:<\/strong> Exactly. Excellent. Well, appreciate you having me. Nick and I have been talking about doing a podcast together. I&#8217;m glad I finally made the list. I think I&#8217;m a fill-in for somebody who had to cancel, so appreciate it, Nick.<\/p>\n<p><strong>Nick:<\/strong> See, it&#8217;s gonna get spicy here, because Rich is technically a fill-in, but he&#8217;s someone I&#8217;ve always wanted to include and could never fit in because his schedule&#8217;s too busy. Even though we&#8217;re good friends, he&#8217;s one of those friends who doesn&#8217;t always answer his texts. You see the read receipt, and then you wait a while until he responds. All right, Rich, let&#8217;s get a quick rundown. Rich and I were roommates in Boston. Both of us were in finance, though that&#8217;s not why we knew each other or hung out. He has bulge bracket experience at a firm everyone knows, Goldman Sachs, and he left to get into the startup world but stayed in finance for a bit. Do you want to give a brief history? It&#8217;ll fit well into our conversation. We&#8217;re gonna talk about building teams and AI and all that stuff.<\/p>\n<p><strong>Richard:<\/strong> Sure. I grew up in New Jersey. My parents are South Korean, and I was born here. I&#8217;ve got a younger brother as well. I spent the first seven years of my life in New Jersey, then did about eight years in Seoul, South Korea, and then came back to the States for high school and went off to Michigan for school. I graduated in 2006, as did you. Back then the dream was to be in finance, so I started my career at Goldman Sachs here in New York. Then I overlapped with Nick, where we were roommates. We had a stint in Boston for about three or four years. Then I went over to Capital Group, another large investment firm. Then I had an itch to become an operator, so I joined a fintech about 10-plus years ago. These were the early days of fintech, when blockchain was just getting started and the Bitcoin paper was just being circulated in small communities. I joined a firm down in Orlando, Florida, which was about a 100-person organization building a lot of technology and a lot of financing, working with mid-market businesses across the US. We exited that business in 2024. And about 15 months ago, I joined the journey that you are on, Nick, which is founding another fintech firm, in this post-AI world, here in New York.<\/p>\n<p><strong>Nick:<\/strong> And how big is your team now? What does the company do?<\/p>\n<p><strong>Richard:<\/strong> We&#8217;re a team of seven people today. We work with mid-market and lower mid-market businesses across the US, helping them with everything from invoicing to payments to collecting on those payments, and helping these finance teams really scale their operations and hopefully also grow their revenue.<\/p>\n<p><strong>Nick:<\/strong> Nice. My version of what you do is you help companies collect money. Is that fair? Okay. So the question I have is, if I was starting Wellable today, I wonder what the team size would be at the various milestones, one year, two years, et cetera, relative to when we started in 2013. My guess is with AI and all these things, it&#8217;d be smaller. I don&#8217;t know the answer to this, but what would the seven-person team today have looked like in the 2010s? Maybe 2X, 3X, probably some multiple. That&#8217;s one of the pitches: you can do more with less with AI. I know your company, so I know you&#8217;re in that bucket of really maximizing the use of that technology and your team&#8217;s potential given the size. But doesn&#8217;t someone today who is in that finance position, the person you&#8217;re selling to, just vibe code this product? If they&#8217;re saying, &#8220;I know my financial situation best,&#8221; is it know-how? Is it the difficulty of actually using AI to create something novel? What&#8217;s the barrier for someone to just do what you&#8217;re doing? Or what&#8217;s the barrier for a more established company you&#8217;re trying to replace to stop you from coming in and overtaking them?<\/p>\n<p><strong>Richard:<\/strong> Wow, okay. That was a lot, so let me try to answer all those questions. One of the questions was about starting a business in this post-AI world, which I consider to be about 18 months ago. But really, I feel like the big change happened in the December\u2013January timeframe, when Claude came out with Opus, whatever the right version number was. What does that look like versus 10 years ago, the pre-AI world? When I was at LSQ, we built a very similar product to what we are building today, and we were serving the same office of the CFO and finance teams. So I feel like I have an apples-to-apples comparison of the pre-AI world and the post-AI world, at least for building our product. I&#8217;m sure every product is different. I think this multiple is sometimes hard for folks to really grasp, but I would say it&#8217;s around a 10X difference in productivity, at least around software and product development, which comprises designers, product folks, and software engineers. When I think about the speed at which we&#8217;ve built our product here at Domio, and the breadth of that product, it&#8217;s about a 10X multiple in team size. We had a team of about 40 folks at my prior company versus today. So that&#8217;s your first question about the pre- versus post-AI world and what a team looks like. And I think this is just really early days. It&#8217;s very hard to predict what this will look like in 12 months as frontier models continue to get better and better. That&#8217;s just comparing pre versus post as of today. Remind me, what was the second question?<\/p>\n<p><strong>Nick:<\/strong> It&#8217;s this theme of the SaaSpocalypse. For established SaaS companies&#8230;<\/p>\n<p><strong>Richard:<\/strong> Right.<\/p>\n<p><strong>Nick:<\/strong> &#8230;the IT person, finance person, HR, whatever function you&#8217;re selling to, they know exactly what they want. They just can&#8217;t push it into code.<\/p>\n<p><strong>Richard:<\/strong> Yeah.<\/p>\n<p><strong>Nick:<\/strong> And maybe there are some internal resources, maybe it&#8217;s themselves. What prevents someone from doing what you&#8217;ve done? You&#8217;ve obviously built a really substantial product in a very short period of time. Good for you. But in this day and age, a lot of people can do that. Maybe the hard part is you have to know the process you need. Not the technology process, but how an invoice moves from step A to step B. These finance teams presumably know that. They just don&#8217;t have the technology background, I&#8217;m guessing. So what prevents them from doing what you&#8217;re doing on their own? Do you believe in the SaaSpocalypse, I guess?<\/p>\n<p><strong>Richard:<\/strong> I don&#8217;t know if I believe in the SaaSpocalypse or not. There are a couple things I&#8217;ll share that I&#8217;ve learned working with different finance folks and teams over the last 18 months or so. One, I actually believe a lot of things will get vibe coded, and I think it will only get better and better. Think about the industry most disrupted by AI, software developers. I don&#8217;t believe most engineers are writing more than 10% of their code base anymore. I actually think more than 95% of code in this world is now being written by AI. That doesn&#8217;t mean software engineers are out of a job. I&#8217;d argue they&#8217;re more effective and more productive than they&#8217;ve ever been, so it&#8217;s really augmented that profession. I think the finance profession is no different. In fact, I think many other domains will also become more productive with AI. That&#8217;s at least my belief.<\/p>\n<p>I&#8217;ve been speaking with some very technical CFOs who have vibe coded a lot of things. But at least for today, here&#8217;s how we&#8217;re approaching the marketplace. One, because we serve the finance function, the margin for error is zero. Think about your bank account. A bank cannot be off by a penny, because if you&#8217;re off by a penny, you might as well be 100% off. You&#8217;ve lost the most important thing in a financial function, which is trust. So that helps, at least with what we&#8217;re doing. But as frontier models get better and better, maybe there will be no margin for error. So what do we do going forward?<\/p>\n<p>There are a couple things I talk to my team about that I think really matter. AI brings abundance to this world, and abundance can be excessive. So I talk about scarcity, I talk about design, I talk about taste. At least for us at Domio, those are areas where you can differentiate in this world of AI, because everybody&#8217;s just building stuff. And the last item I&#8217;ll mention is that we don&#8217;t necessarily sell to the coastal, Y Combinator, tech-heavy businesses. We work with what I&#8217;d call the backbone of this country, the real economy. Think of businesses that have been around for decades. Some are still run by families, multi-generational businesses. They&#8217;re not as tech-savvy, and there&#8217;s an element of trust with AI that&#8217;s very important to them. That has really resonated for us. I&#8217;m trying to build that brand with these customers and introduce AI to what we consider non-coastal, middle-of-America companies.<\/p>\n<p><strong>Nick:<\/strong> Let me push back a little bit on that. First, take the idea that maybe people could vibe code it. Someone sitting in your kind of role, how do they come in when they talk to a client? You have a workflow. Everything&#8217;s about optimizing some type of workflow, from sending the invoice out, receiving it, collecting it, reconciling it, et cetera. The opportunity cost for you is very high. You exit LSQ, you have a great resume, you can go somewhere else. Maybe it was a throwaway comment, but you said these models may eventually get really good and possibly be able to do that. Do you really believe that&#8217;s the case? And if so, why start a business if you think that&#8217;s possible? I think about this a lot for our company. It doesn&#8217;t need to be better to really mess up your company. Someone could believe they can vibe code a wellness app, and whether they can really do it or not doesn&#8217;t matter. They&#8217;re still not going to purchase yours. They&#8217;re going to invest their time and energy in doing something else, and that&#8217;s one less customer and all this extra friction. So it doesn&#8217;t need to be better to disrupt your business. I heard your story and thought, &#8220;Why make that leap?&#8221;<\/p>\n<p><strong>Richard:<\/strong> I don&#8217;t know. Maybe I like pain. Building is certainly fun. And what&#8217;s important is that the world will not stay static. In this world of AI, where things are moving faster than ever, part of your question is how is Domio going to survive? Why do this if everybody can just vibe code?<\/p>\n<p><strong>Nick:<\/strong> How are you gonna survive?<\/p>\n<p><strong>Richard:<\/strong> Great question.<\/p>\n<p><strong>Nick:<\/strong> Yeah.<\/p>\n<p><strong>Richard:<\/strong> For us, there&#8217;s a sense of paranoia we operate with, which I think is probably healthy for any business. You and I have more gray hair today than we did 25 years ago, and we&#8217;ve seen a lot of ups and downs and a lot of changes. There have been many times where there was fear around, &#8220;How are you going to survive this? How is this industry going to survive this?&#8221; But truth is, I think that&#8217;s the nature of capitalism. So what are we doing today in this world of AI? What we think is very important is increasing our surface area, and increasing it into areas that are maybe not just traditional workflow in its most fundamental sense. It&#8217;s going into areas where there&#8217;s some regulation. Payments is a great example. When you start moving money around in any form, the bar for getting that right is much higher, the margin for error is smaller. Maybe it&#8217;s getting into lending, again a highly regulated space. I don&#8217;t think that&#8217;s going to get &#8220;AI-pilled&#8221; right away, and it buys you more time to figure out survival in this world of AI. So increasing surface area is one area that&#8217;s been very important to us.<\/p>\n<p>And finally, I&#8217;m not a believer in a world of AI where everything is just agents talking to other agents. I think humans like work. I think humans like doing stuff. I think how humans work with AI will change, but not in a way where everything gets automated away and nothing&#8217;s left for humans to do. That&#8217;s how we&#8217;re approaching the current state of AI. How are you approaching it at Wellable?<\/p>\n<p><strong>Nick:<\/strong> I&#8217;ll get into that in a little bit. The challenge I have, which is why I&#8217;m really interested in this conversation, is the question I&#8217;d throw back to you: do you think LSQ could have become Domio? I&#8217;m sure there are nuances in the product, but remove that. Say they were trying to solve the exact same problem. Do you think that was possible? Or structurally, because it was founded and built at a time when AI wasn&#8217;t there, is the shift too material, whether that&#8217;s a people shift, a technology shift, or a process shift? Let&#8217;s start there, because that&#8217;s a question that&#8217;s really alive for me. Us starting today and trying to create what we created is a very different analysis and decision than when we started 13 years ago.<\/p>\n<p><strong>Richard:<\/strong> I won&#8217;t speak for LSQ specifically, but what you&#8217;re getting at is pre-AI incumbents versus post-AI companies. We can just focus on the software industry specifically. I don&#8217;t think most will make it. I do think there will be exceptions. And this is no different to me from 10 years ago with venture-backed companies or new startups. Can they survive long enough? Can they acquire enough customers while the incumbents figure things out and wake up one day? Or will the incumbents get disrupted? It&#8217;s no different today. It&#8217;s just a different medium, which is this thing called AI. AI is certainly much more powerful, and maybe things will move faster, but the fundamental dynamic hasn&#8217;t changed. So I don&#8217;t think the fundamental outcome will be that different. You&#8217;ll have exceptions where incumbents figure things out, and I&#8217;m sure there will be a lot of industry dynamics depending on other hurdles or barriers to entry. And you&#8217;ll have a lot of disruptors. When I think about my field, there&#8217;s literally a new Y Combinator company coming out doing exactly what we are doing. They sound exactly the same. Their website says the exact same thing. Some of them will survive. Most of them will not. Just because you&#8217;re AI doesn&#8217;t mean you&#8217;re going to make it. You might not figure out go-to-market. You might not get enough runway to figure stuff out. It&#8217;s the same thing for both incumbents and startups. Most of them will not make it. And for incumbents, it&#8217;s very hard to just AI-pill your company because of cultural dynamics, unit economics, tech debt, everything else. So I don&#8217;t know if LSQ would have made the transition, but across the broader software and technology complex, I think most will not. But some will figure it out, and probably even thrive more because they survived and got to the other side of AI.<\/p>\n<p><strong>Nick:<\/strong> I&#8217;ll give you an example. I wasn&#8217;t trying to call LSQ out, I was just using them as an example. Last week I was talking with a company, not to be named, that you would know. It&#8217;s a direct-to-consumer company in the health and wellness space, so there&#8217;s some small corporate business, and it&#8217;s down 60\u201370% from its peak revenue. It&#8217;s struggling for a lot of different reasons, so they&#8217;re in survival mode. How do you lose that much revenue and make it work? When I was talking to them, they told me, &#8220;We just rebuilt our whole application to make it more scalable, and we did that strictly with AI. Not a single coder wrote a single line of code.&#8221; And they did it with a way trimmed-down team, because they had to reduce the workforce substantially. They actually brought a whole new team in because they had to retool. That&#8217;s how an LSQ would have to do it. And they said, &#8220;Our support used to be managed through X number of people, and now 85% of tickets are handled through AI.&#8221; They went through the list, and it sounded like an incredible success story in some ways, absent the financial piece.<\/p>\n<p>And I told them, since we were having a casual conversation, &#8220;It&#8217;s almost unbelievable.&#8221; I juxtapose this with what we see in our day-to-day lives and what I read online in almost every survey of executives and management about whether there&#8217;s ROI on AI today. The answer is almost universally no, well past the margin of error. I&#8217;m not saying that just because there&#8217;s no ROI today, there won&#8217;t be in the future. But right now, people are still trying to figure it out. Then I see companies like yours and what this company did, and it&#8217;s a completely different story. I asked, &#8220;What does it take for a company like us to do it?&#8221; And the CEO said, &#8220;We had to press the delete button. We had to delete the whole company. We had to literally say, &#8216;Look, we have this history, we have these customer relationships, but we have to start fresh.'&#8221; That was really the genesis of rebuilding the whole thing. It would be nice to modernize the platform, but they had to press delete, because for what they wanted to do, they couldn&#8217;t start from the old platform or the old support system, even though that seemed easier. They had to make the hard call, and they would never have made that decision in a practical sense if their revenue was even flat. What forced it was the precipitous drop in the financials that said, &#8220;Our only way to survive is to do this.&#8221;<\/p>\n<p>We&#8217;re not in a situation where we&#8217;re going through a precipitous drop in revenue. We see those stories and value that experience for how they&#8217;re able to drive success in their business. We could talk for hours about why we&#8217;ve struggled to make it really work materially in our business. No question, I would say we have a positive ROI from AI, but I also think we&#8217;re just grabbing the low-hanging fruit, so it&#8217;s easy to do that.<\/p>\n<p>And to your point about agent versus agent, I don&#8217;t know if that&#8217;s the future. I certainly hope it&#8217;s not. But I think you may be asking the wrong question. You said people want to interact with people, and I completely agree. But the real question is, do managers care about the interaction? If senior folks go, &#8220;I can cut my support team by 20% by making it mostly agents,&#8221; they&#8217;re making the decision. Maybe they value interactions with people, but they&#8217;re fine with their workforce shrinking by 50%. It&#8217;s like the Jack Dorsey Block story. I bet Jack Dorsey, who built a social network, cares about social interactions. I&#8217;ll give him the benefit of the doubt. But it didn&#8217;t stop him from laying off 40% of the people and espousing a vision where there&#8217;s only a single layer of management, him and 6,000 people reporting to him. Dystopian aside, it&#8217;s hard to see how certain companies adapt, ourselves included. That&#8217;s why I was asking: do you think LSQ could do it, not to call them out specifically, but in general, what does it take? Does it take the delete button, or can you do it organically over time, and will it be quick enough?<\/p>\n<p><strong>Richard:<\/strong> It&#8217;s interesting, because I feel like AI sometimes distorts other, more fundamental questions about the software complex, at least in the world I traffic in, which is B2B software. Think enterprise software, not consumer-focused. I always ask CFOs, who are my customer base, &#8220;Can you name me one piece of software that you are happy using?&#8221; I don&#8217;t ask whether it&#8217;s AI or not. Just, what are you happy with, and what&#8217;s the ROI of that software? The honest answer is I get silence. There is not one piece of software I consistently hear about across the CFO landscape of mid-market American companies where they say they&#8217;re happy with it. Usually, they&#8217;re on some ERP, which is kind of a grown-up version of QuickBooks. It could be NetSuite, Microsoft, SAP, Oracle, you name it. Then they have some FP&amp;A software, some payment software, maybe some invoicing software. That&#8217;s the finance tech stack. That has actually been my number one takeaway, and it&#8217;s unrelated to AI.<\/p>\n<p>Since 2010 or so, software has really taken off across both consumers and businesses, and I don&#8217;t see a lot of happy customers. So when you think about building a business, I&#8217;d say keep it pretty simple. Do you have a happy customer who feels they are getting a high return on investment from the software you&#8217;re selling them? Right now for the incumbents, I think that&#8217;s a resounding no. And that&#8217;s where trust has been lost for many industries served by B2B software. That&#8217;s where I see the most opportunity, and to me, it&#8217;s unrelated to AI. Having seen the ups and downs of different market cycles, I&#8217;d go somewhere much more basic. Is your customer happy? Do they love your product? Do they have a delightful experience? Do they feel like they&#8217;re getting a high return on investment? The CFO especially cares a lot about that. And they can&#8217;t even tell me what the ROI is. So I think AI may be hiding the fact that software was cool 10 or 15 years ago, but has largely sucked for the customer since. Part of it is that software companies over-indexed on a sticky moat, and AI has removed that stickiness. But the truth is, I think they just lost trust. So AI or not AI, it doesn&#8217;t matter. Start with: is your customer happy with the product you&#8217;re selling them?<\/p>\n<p><strong>Nick:<\/strong> Going back to the happy thing, I&#8217;ll say this half in jest but half true: I don&#8217;t think any CFO is being legit if they don&#8217;t think Excel is a great product. It&#8217;s maybe the greatest productivity tool of all time.<\/p>\n<p><strong>Richard:<\/strong> I agree with that 100%, by the way. Excel is the only thing.<\/p>\n<p><strong>Nick:<\/strong> It&#8217;s never gonna be&#8230;<\/p>\n<p><strong>Richard:<\/strong> Correct. I think the broader tech and software complex poo-poos Excel, but I&#8217;d argue it&#8217;s the greatest product ever sold to the CFO. They&#8217;re very happy with it, with a very high ROI. For all the other software, I&#8217;ve yet to see or hear about a happy customer.<\/p>\n<p><strong>Nick:<\/strong> Going back to AI, I feel like I&#8217;m kind of poo-pooing AI, but that&#8217;s not how I feel. My optimistic vision is that the future is yet to come, and it&#8217;s going to be amazing. But a lot of people talk about it as if it&#8217;s here today, and I personally ask myself, what am I missing? What are we not doing well enough? Why don&#8217;t we have that narrative of 85% of support tickets addressed through AI? Not that specifically, but generally that level of AI adoption and ROI.<\/p>\n<p>I come back to one of the Wellable Weekly newsletters, for example. There were two articles in it. One talked about how recruitment is one of the biggest stressors in HR today, mostly driven by AI. Then there was the opposite one about something called &#8220;resume Botox,&#8221; where candidates are trying to make themselves seem younger, because if you&#8217;re younger, it looks like you&#8217;re more AI-native. People always used to make themselves look younger on LinkedIn with edits or a new headshot. But in this article, people are saying, &#8220;I&#8217;m going to remove my title. I&#8217;m going to remove my graduation date or remove my university completely.&#8221; They&#8217;re trying to literally rewind the clock for someone who&#8217;s not just taking a cursory look at their resume but actually going to their LinkedIn page. They do it because being 50, or whatever the cutoff is, doesn&#8217;t seem like you&#8217;d know how to adopt AI.<\/p>\n<p>Those don&#8217;t strike me as two good use cases of AI, and they seem relatively prevalent. Everyone I know in the job market has told me how AI improved their resume, or how they perceived it improved their resume. I hear tons from HR in surveys saying they&#8217;re getting more applicants than ever. So it&#8217;s easier to apply to a job than ever before, and it&#8217;s so hard to sort through those resumes as an individual that they have an AI tool filter them. It&#8217;s very agent to agent. No one seems super happy. Both sides seem a little bit dishonest or mistrustful of the situation. And that&#8217;s one direction of a post-AI world.<\/p>\n<p>The last thing I&#8217;ll give you, and this is all speculation: in my world, Fitbit very recently became Google Health. From my perspective and our users&#8217; perspective, it&#8217;s been a real step back. The Google Health app has been really bad. And online, a lot of people are saying, &#8220;This must be vibe coded.&#8221; It&#8217;s such a small business for Google, like a $5 billion product. It&#8217;s a drop in the bucket, and they probably don&#8217;t care about it. Again, I&#8217;m speculating, but maybe they said, &#8220;Let&#8217;s just vibe code this thing.&#8221; They produced it, and everyone seems to hate it. Developers hate it because with the API we&#8217;re getting all these weird error responses. And it&#8217;s not just us. I&#8217;m seeing MyFitnessPal send messages with apologies and things like that, so it seems to be more than just a Wellable issue. So if the success story is that they somehow rebuilt all of Fitbit into Google Health in three weeks, I don&#8217;t see a big win. And the last point I&#8217;ll make: I think I saw a stat that the number of apps released in the App Store is up something like 500%, something insane, while the number of downloads is pretty much flat, down 1% just because of saturation. We&#8217;re producing more than ever, but clearly not more value.<\/p>\n<p><strong>Richard:<\/strong> I go back to keeping it simple. Can you build something that somebody actually loves using? Is it a delightful experience? Get that right, and it doesn&#8217;t matter if it&#8217;s AI or not. AI is a world of abundance. There have probably never been more companies starting with AI, and it&#8217;s never been easier to develop an app and put it in the App Store. But that doesn&#8217;t win. I think what that means is it&#8217;s a higher bar if you want to win in this world of AI, because everybody can now do more. That doesn&#8217;t mean everything you do more of is good. Think about all the AI slop. I can create an unlimited amount of marketing collateral today with AI. But when I think about the pieces that actually resonate with our customers or prospects, it&#8217;s the ones with really good taste, really good design, and a human layered on top of the AI. Maybe the frontier models will get there, and the next version of collateral that comes out of whatever Fable or Claude model it is will have that human touch and feel authentic because the models got so good. I don&#8217;t see it right now. So in today&#8217;s world of AI abundance, I think scarcity, taste, design, and that human element are what differentiate, and that&#8217;s what wins today. AI isn&#8217;t winning alone. What&#8217;s going to be interesting is what this looks like in 12 or 24 months when the models get even better. That, I have no idea. We&#8217;ll have to pivot again, just like humans always do.<\/p>\n<p><strong>Nick:<\/strong> Let&#8217;s move to development. You&#8217;ve been a manager at a bunch of companies of different sizes, from super large organizations to mid-size ones to now a startup. In this world of AI, where everyone seems to be a super individual contributor, what&#8217;s the pitch to someone on your team? In the old world, 10 years ago, it was, &#8220;You&#8217;re an early employee. We&#8217;re going to have success. You&#8217;re going to grow. You&#8217;ll be a senior developer, then an engineering manager. There&#8217;s all this structure.&#8221; What&#8217;s that pitch now? It could be, &#8220;You&#8217;ll always be an IC, and that&#8217;s great because we&#8217;ll distribute our gains.&#8221; How are you thinking about recruiting and retaining people in a world where what we&#8217;re seeing organizationally and structurally hasn&#8217;t been the norm and may be the new normal?<\/p>\n<p><strong>Richard:<\/strong> What&#8217;s that saying you always used to say? A players want to be around other A players. I think that was incredibly true back then, and it&#8217;s incredibly true today. But maybe the standard for what an A player looks like has never been higher, in my opinion. You need to give them a lot of latitude and a lot of autonomy, and the ability to make an impact and have influence, so they feel really good about the work they produce, at least in software development, and feel like it&#8217;s making an impact. Those attributes haven&#8217;t changed from 15 years ago. I have friends who are way smarter and way more successful than I am, and they wanted those qualities 20 years ago when they graduated. It&#8217;s no different today. The new grad wants the exact same thing. So that has not changed.<\/p>\n<p>Now, I do believe the output of individuals who have taken AI seriously and added it to their toolkit, whether they&#8217;re straight out of school or 50 years old, has never been higher. You&#8217;ve heard of the term 10X engineers from the pre-AI world. I feel like there are a ton of 10Xers now. Everything&#8217;s relative, so maybe that 10Xer is now a 100Xer, and I&#8217;m sure some of those exist, with agents orchestrating their code. But it comes back down to: do you give them enough autonomy? Do they feel micromanaged or not? Do you give them decision-making ability and influence? What cultural environment do you help foster? How do you help with their career progression? Those things still matter, and they&#8217;re the same things that mattered 10 and 20 years ago.<\/p>\n<p><strong>Nick:<\/strong> Let&#8217;s fast-forward. Your revenue quadruples. Do you think your team quadruples at this stage? Maybe it&#8217;s different when you&#8217;re much bigger. Does it double? And as it grows, do you see yourself as the sole manager of everyone because the team may be small enough? Or will there be several layers? How do you envision that?<\/p>\n<p><strong>Richard:<\/strong> I think our revenue can 10X and we&#8217;ll stay the same team size. So it&#8217;s not just quadrupling. This is where I&#8217;m curious to see how it plays out, and I do think it&#8217;s a structural advantage for companies like us. When I think about our incumbents, I think about all the reasons they won&#8217;t be able to serve the end customer, the CFO. What&#8217;s the denominator on ROI? It&#8217;s the ACV, the annual contract value. The numerator is all the value you bring. Let&#8217;s assume the numerator is the same for everybody. The denominator is where, as an AI-native company, I&#8217;ll have significant structural advantages over my incumbents. My incumbents have a ton of debt on the balance sheet because of acquisitions, because they&#8217;re private equity-backed, or because they took venture debt. Let&#8217;s just start there. Debt is really expensive. Rates are high. My guess is they&#8217;re borrowing at somewhere between 12 and 14%. And they LBO&#8217;d these businesses at the peak of COVID at very high valuations. Valuations have now gone to about a third of what they were, and they have to keep servicing this debt. There&#8217;s no worse use of capital than interest expense, and they can&#8217;t get rid of it. That&#8217;s the American economy. Debt is never repaid, it&#8217;s just rolled over again and again. How they price a product to a customer is driven by unit economics, and part of that equation is how they service their debt. That has nothing to do with how happy the customer is or whether it&#8217;s a delightful experience. None of that matters. It&#8217;s related to something else, like the founders who got to cash out five years ago. So when I think about that structural change and team size, my guess is their engineering team, for the same level of output, is probably 10X the size of ours. That&#8217;s where we have a structural advantage. We don&#8217;t have to add another headcount, and I think we have significant operating leverage. Can the incumbents do that? They should be able to. Will they? That I don&#8217;t know. So I&#8217;m curious to see what this looks like over the next 12, 24, maybe 36 months, and who&#8217;s better at serving that end customer, whether you&#8217;re AI or not AI. How do you think about this? You&#8217;re a pre-AI company, but you&#8217;re obviously thinking hard about this and paying a lot of attention to how to position your company in this world of AI.<\/p>\n<p><strong>Nick:<\/strong> Let me ask you one question first. Right now, assuming your revenue grows but your headcount doesn&#8217;t, does everyone report to you? Are you small enough to manage that?<\/p>\n<p><strong>Richard:<\/strong> Yes, for now. I don&#8217;t think it will always be that way. There&#8217;s probably a ceiling, at least for me, and I think every manager is different in terms of the right number. For me, the ideal number of direct reports is probably around 10, if I have 10 really high-performing individuals. Over time, I generally lean toward flatter, leaner organizations. I&#8217;m okay pushing the boundaries on removing slack, because I&#8217;m more afraid of there being slack and too much capacity. That scares me more from a cultural standpoint. So I probably tend to under-hire, maybe sometimes for too long, but I&#8217;d rather operate that way than create more slack and too much capacity. So for now, we&#8217;ll try to keep it flat as long as possible. I don&#8217;t think it will be that way forever, but for me, that number is probably around 10, where I think there needs to be some form of hierarchy.<\/p>\n<p><strong>Nick:<\/strong> And is 10 what you&#8217;d say has always been the case, or is that 10 in this new AI world, where you can rip out call notes and follow-up emails? Is that 10 new, or has that always been the case?<\/p>\n<p><strong>Richard:<\/strong> No, I think this is the 10 in the AI world.<\/p>\n<p><strong>Nick:<\/strong> Okay.<\/p>\n<p><strong>Richard:<\/strong> Yeah.<\/p>\n<p><strong>Nick:<\/strong> What was it before?<\/p>\n<p><strong>Richard:<\/strong> I don&#8217;t know. I think in the old world this would probably be an organization of 50 to 75 people, is my guess.<\/p>\n<p><strong>Nick:<\/strong> I&#8217;m saying how many people do you think is the ideal number of direct reports?<\/p>\n<p><strong>Richard:<\/strong> Hmm. No, I&#8217;d say that&#8217;s always been 10 for me. The human element there is more important than the other things.<\/p>\n<p><strong>Nick:<\/strong> Yeah. To answer your question about Wellable, the tricky part is we hear this a lot from people looking for career development. They want all the things you mentioned: autonomy, purpose-driven work, all those types of things. But they also want to see demonstrable career development they can point to. Some of that is title, some of that is comp, but those can only go so far. At some point, people want to manage people. They want to get out of individual contributor work, which is odd, because AI is dragging everyone, including myself, more toward it. I get excited about individual contributor work. I still like to open an Excel document every now and then and really get my hands dirty. I do QA, all that type of stuff. But that&#8217;s counter to the general population, I think, so there&#8217;s a natural tension there. Wellable&#8217;s no different. Someone&#8217;s been around for a long time and asks, &#8220;When do I get to start managing people?&#8221;<\/p>\n<p><strong>Richard:<\/strong> Yeah.<\/p>\n<p><strong>Nick:<\/strong> Before, there was a path. &#8220;Eventually we&#8217;re going to have to hire, and someone&#8217;s going to become a director and have direct reports.&#8221; But in this current world, it becomes harder and harder to see how that happens. We&#8217;re trying to make a shift, and it&#8217;s hard to make that shift. We&#8217;re trying to identify it, and each functional group is a little bit different. It&#8217;s not that simple, because part of what you want to do is hear what the employee wants. Everyone&#8217;s different, but generally there&#8217;s a thread, and a not-insignificant portion of people want career development in the form of being a manager, and that&#8217;s increasingly hard to do. So we&#8217;re trying to figure it out.<\/p>\n<p>I think part of it is also societal. We are an in-office, two-days-a-week company. If I had my way, I think the proper number is three.<\/p>\n<p><strong>Richard:<\/strong> Hmm.<\/p>\n<p><strong>Nick:<\/strong> But we came to two. We originally told everyone it was going to be three, and when we actually came back from COVID, we stuck to two, mostly because we wanted to be competitive as a hybrid workplace, and 2.2 days was the average. Now I think the average is right around three days in, and it&#8217;s slowly creeping up. I suspect if there&#8217;s ever a recession, that number will increase, because remote employees unfortunately tend to get marginalized in that situation. If it ever came to the average employee being in four days a week, we&#8217;d probably consider being a three-day-a-week company. I&#8217;m not sure we would do it, because there&#8217;d still be a ton of pushback from the employee base, but we could say, &#8220;Hey, we&#8217;re competitive in the market.&#8221; I haven&#8217;t even gone that far out to really think about it. But I think how society and other jobs out there evolve will dictate how we try to accommodate this shift. The reality is when you do that, you&#8217;re kind of driving from behind. I&#8217;m aware of that. But it seems a little bit easier, and there&#8217;s no shortage of other things we&#8217;re working through.<\/p>\n<p><strong>Richard:<\/strong> Good luck going from two to three.<\/p>\n<p><strong>Nick:<\/strong> Yeah, right? I say that now, and I guarantee there are people in our company listening to this going, &#8220;What? We&#8217;re going to three?&#8221; To be abundantly clear, there&#8217;s no plan to do so. It&#8217;s just my personal view, and there are a lot of things I hold personally that just don&#8217;t happen here, for a lot of good reasons.<\/p>\n<p><strong>Richard:<\/strong> Well, what are the odds of going from two to one?<\/p>\n<p><strong>Nick:<\/strong> I would need to see a good case. At that point, I think you go to zero. Why pay for office space and all that?<\/p>\n<p><strong>Richard:<\/strong> Yeah.<\/p>\n<p><strong>Nick:<\/strong> No one&#8217;s ever asked me that question, but that&#8217;s my first reaction. Even now, it&#8217;s hard to pay for office space and all the infrastructure with two days a week. You&#8217;re kind of burning it for 60% of the days. And we have optional flex weeks too. If you count the full year, holidays, and our optional flex weeks, there&#8217;s a significant portion of dead time you have to pay for. And Boston, San Diego, DC, Halifax, these are not necessarily cheap real estate markets.<\/p>\n<p><strong>Richard:<\/strong> Yeah.<\/p>\n<p><strong>Nick:<\/strong> One question before we wrap up. I ask all of our guests for a prediction. It could be anything. It could be what we discussed, or it could be that the Knicks are going to win it again, although they just lost to the Celtics. Any predictions for us?<\/p>\n<p><strong>Richard:<\/strong> Well, I&#8217;m a Brooklyn Nets fan, so we&#8217;re in the basement. I won&#8217;t make an NBA prediction. Oh boy.<\/p>\n<p><strong>Nick:<\/strong> They play the Celtics tomorrow, by the way.<\/p>\n<p><strong>Richard:<\/strong> Oh, is that right? Okay.<\/p>\n<p><strong>Nick:<\/strong> Yeah. We&#8217;re recording this on Monday the 26th, if anyone&#8217;s curious, and they play on the 27th. Go ahead.<\/p>\n<p><strong>Richard:<\/strong> Excellent. If folks are still listening, I&#8217;m assuming most people have already snoozed off. So a prediction. Oh man. Okay. I think we will have a third political party that will be taken seriously in the next general election.<\/p>\n<p><strong>Nick:<\/strong> You don&#8217;t mean November, you mean the next&#8230;<\/p>\n<p><strong>Richard:<\/strong> The next presidential election.<\/p>\n<p><strong>Nick:<\/strong> I was going to say, that&#8217;s a bold prediction if you&#8217;re talking about two weeks from now.<\/p>\n<p><strong>Richard:<\/strong> And I don&#8217;t think it&#8217;s going to be Mark Cuban.<\/p>\n<p><strong>Nick:<\/strong> Okay, that would have been my first guess. All right, awesome. How can people stay in contact with you, connect with you, and hear your thoughts?<\/p>\n<p><strong>Richard:<\/strong> Feel free to email me at <a href=\"mailto:richard@domio.ai\">richard@domio.ai<\/a> or find me on LinkedIn. This was fun, Nick. Really appreciate you having me on, and happy to do this whenever.<\/p>\n<p><strong>Nick:<\/strong> Of course. Thanks for coming. I really appreciate it. Long overdue, so I&#8217;m glad we made it happen. Thanks to all of our listeners as well. You can catch us on Apple Podcasts, Spotify, or wherever you get your podcasts. Be sure to like, subscribe, and sign up for our newsletter.<\/p>\n <\/div>\n <\/div>\n\n \n <\/div>\n <\/section>\n\n \n","protected":false},"excerpt":{"rendered":"<p>Richard Lee joins Wellable Weekly to discuss AI-native startups, lean teams, vibe coding, and how to offer career growth when companies stay small and flat.<\/p>\n","protected":false},"author":1,"featured_media":35901,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_feature_clip_id":0,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_post_was_ever_published":false},"categories":[23],"tags":[],"class_list":["post-35892","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-podcasts"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO Premium plugin v20.6 (Yoast SEO v28.7) - https:\/\/yoast.com\/product\/yoast-seo-premium-wordpress\/ -->\n<title>How AI Is Reshaping Team Capabilities with Richard Lee | Wellable<\/title>\n<meta name=\"description\" content=\"Richard Lee joins Wellable Weekly to discuss AI-native startups, lean teams, vibe coding, and how to offer career growth when companies stay small and flat.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"How AI Is Reshaping Team Capabilities with Richard Lee | Wellable\" \/>\n<meta property=\"og:description\" content=\"Richard Lee joins Wellable Weekly to discuss AI-native startups, lean teams, vibe coding, and how to offer career growth when companies stay small and flat.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/\" \/>\n<meta property=\"og:site_name\" content=\"Wellable\" \/>\n<meta property=\"article:publisher\" content=\"https:\/\/www.facebook.com\/GetWellable\/\" \/>\n<meta property=\"article:published_time\" content=\"2026-10-28T16:55:48+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2026-10-29T08:43:50+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.wellable.co\/blog\/wp-content\/uploads\/2026\/10\/How-AI-Is-Reshaping-Team-Capabilities-with-Richard-Lee-2.png\" \/>\n\t<meta property=\"og:image:width\" content=\"1280\" \/>\n\t<meta property=\"og:image:height\" content=\"720\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/png\" \/>\n<meta name=\"author\" content=\"Wellable\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:creator\" content=\"@getwellable\" \/>\n<meta name=\"twitter:site\" content=\"@getwellable\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Wellable\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"5 minutes\" \/>\n<!-- \/ Yoast SEO Premium plugin. -->","yoast_head_json":{"title":"How AI Is Reshaping Team Capabilities with Richard Lee | Wellable","description":"Richard Lee joins Wellable Weekly to discuss AI-native startups, lean teams, vibe coding, and how to offer career growth when companies stay small and flat.","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/","og_locale":"en_US","og_type":"article","og_title":"How AI Is Reshaping Team Capabilities with Richard Lee | Wellable","og_description":"Richard Lee joins Wellable Weekly to discuss AI-native startups, lean teams, vibe coding, and how to offer career growth when companies stay small and flat.","og_url":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/","og_site_name":"Wellable","article_publisher":"https:\/\/www.facebook.com\/GetWellable\/","article_published_time":"2026-10-28T16:55:48+00:00","article_modified_time":"2026-10-29T08:43:50+00:00","og_image":[{"width":1280,"height":720,"url":"https:\/\/www.wellable.co\/blog\/wp-content\/uploads\/2026\/10\/How-AI-Is-Reshaping-Team-Capabilities-with-Richard-Lee-2.png","type":"image\/png"}],"author":"Wellable","twitter_card":"summary_large_image","twitter_creator":"@getwellable","twitter_site":"@getwellable","twitter_misc":{"Written by":"Wellable","Est. reading time":"5 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/#article","isPartOf":{"@id":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/"},"author":{"name":"Wellable","@id":"https:\/\/www.wellable.co\/blog\/#\/schema\/person\/81c5d87251e10f83d01bf69eb099f792"},"headline":"How AI Is Reshaping Team Capabilities with Richard Lee","datePublished":"2026-10-28T16:55:48+00:00","dateModified":"2026-10-29T08:43:50+00:00","mainEntityOfPage":{"@id":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/"},"wordCount":878,"publisher":{"@id":"https:\/\/www.wellable.co\/blog\/#organization"},"image":{"@id":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/#primaryimage"},"thumbnailUrl":"https:\/\/www.wellable.co\/blog\/wp-content\/uploads\/2026\/10\/How-AI-Is-Reshaping-Team-Capabilities-with-Richard-Lee-2.png","articleSection":["Podcasts"],"inLanguage":"en-US"},{"@type":"WebPage","@id":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/","url":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/","name":"How AI Is Reshaping Team Capabilities with Richard Lee | Wellable","isPartOf":{"@id":"https:\/\/www.wellable.co\/blog\/#website"},"primaryImageOfPage":{"@id":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/#primaryimage"},"image":{"@id":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/#primaryimage"},"thumbnailUrl":"https:\/\/www.wellable.co\/blog\/wp-content\/uploads\/2026\/10\/How-AI-Is-Reshaping-Team-Capabilities-with-Richard-Lee-2.png","datePublished":"2026-10-28T16:55:48+00:00","dateModified":"2026-10-29T08:43:50+00:00","description":"Richard Lee joins Wellable Weekly to discuss AI-native startups, lean teams, vibe coding, and how to offer career growth when companies stay small and flat.","breadcrumb":{"@id":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/#breadcrumb"},"inLanguage":"en-US","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/"]}]},{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/#primaryimage","url":"https:\/\/www.wellable.co\/blog\/wp-content\/uploads\/2026\/10\/How-AI-Is-Reshaping-Team-Capabilities-with-Richard-Lee-2.png","contentUrl":"https:\/\/www.wellable.co\/blog\/wp-content\/uploads\/2026\/10\/How-AI-Is-Reshaping-Team-Capabilities-with-Richard-Lee-2.png","width":1280,"height":720,"caption":"How AI Is Reshaping Team Capabilities with Richard Lee"},{"@type":"BreadcrumbList","@id":"https:\/\/www.wellable.co\/blog\/richard-lee-ai-team-size-lean-teams-career-growth\/#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/www.wellable.co\/blog\/"},{"@type":"ListItem","position":2,"name":"How AI Is Reshaping Team Capabilities with Richard Lee"}]},{"@type":"WebSite","@id":"https:\/\/www.wellable.co\/blog\/#website","url":"https:\/\/www.wellable.co\/blog\/","name":"Wellable","description":"Latest Research &amp; News in Wellness","publisher":{"@id":"https:\/\/www.wellable.co\/blog\/#organization"},"potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/www.wellable.co\/blog\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"en-US"},{"@type":"Organization","@id":"https:\/\/www.wellable.co\/blog\/#organization","name":"Wellable","url":"https:\/\/www.wellable.co\/blog\/","logo":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.wellable.co\/blog\/#\/schema\/logo\/image\/","url":"https:\/\/www.wellable.co\/blog\/wp-content\/uploads\/2022\/06\/favicon-wellable.webp","contentUrl":"https:\/\/www.wellable.co\/blog\/wp-content\/uploads\/2022\/06\/favicon-wellable.webp","width":155,"height":157,"caption":"Wellable"},"image":{"@id":"https:\/\/www.wellable.co\/blog\/#\/schema\/logo\/image\/"},"sameAs":["https:\/\/www.facebook.com\/GetWellable\/","https:\/\/x.com\/getwellable","https:\/\/www.linkedin.com\/company\/wellable-inc-\/","https:\/\/www.youtube.com\/channel\/UCtTLlvZR-tKRBcb32l-rFXg"]},{"@type":"Person","@id":"https:\/\/www.wellable.co\/blog\/#\/schema\/person\/81c5d87251e10f83d01bf69eb099f792","name":"Wellable","image":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/secure.gravatar.com\/avatar\/acf8de6b4e70889e608d47410dcdc1ac0fea5050a1d89c468bea5ae977f4eda7?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/acf8de6b4e70889e608d47410dcdc1ac0fea5050a1d89c468bea5ae977f4eda7?s=96&d=mm&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/acf8de6b4e70889e608d47410dcdc1ac0fea5050a1d89c468bea5ae977f4eda7?s=96&d=mm&r=g","caption":"Wellable"},"sameAs":["http:\/\/34.168.145.72"],"url":"https:\/\/www.wellable.co\/blog\/author\/wellable-admin\/"}]}},"jetpack_sharing_enabled":true,"jetpack_featured_media_url":"https:\/\/www.wellable.co\/blog\/wp-content\/uploads\/2026\/10\/How-AI-Is-Reshaping-Team-Capabilities-with-Richard-Lee-2.png","_links":{"self":[{"href":"https:\/\/www.wellable.co\/blog\/wp-json\/wp\/v2\/posts\/35892","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.wellable.co\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.wellable.co\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.wellable.co\/blog\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.wellable.co\/blog\/wp-json\/wp\/v2\/comments?post=35892"}],"version-history":[{"count":6,"href":"https:\/\/www.wellable.co\/blog\/wp-json\/wp\/v2\/posts\/35892\/revisions"}],"predecessor-version":[{"id":35899,"href":"https:\/\/www.wellable.co\/blog\/wp-json\/wp\/v2\/posts\/35892\/revisions\/35899"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.wellable.co\/blog\/wp-json\/wp\/v2\/media\/35901"}],"wp:attachment":[{"href":"https:\/\/www.wellable.co\/blog\/wp-json\/wp\/v2\/media?parent=35892"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.wellable.co\/blog\/wp-json\/wp\/v2\/categories?post=35892"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.wellable.co\/blog\/wp-json\/wp\/v2\/tags?post=35892"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}