Vlad on Leadership

About Vlad on Leadership

Interviews with technical leaders and operators about the leadership questions AI just made harder. Concrete and actionable insights to help you lead well when the ground keeps moving.

Publisher

Vlad Moskovski

Category

business · technology

Language

en

Explicit

No

First episode

25 Jul 2026

Latest episode

16 Oct 2026

Latest episodes

9 episodes in the feed.

1. 

   16 Oct 2026

   The AI Tool Is the Last Decision | Josh Norris | GTM Strategist

   **Josh Norris runs a San Francisco go-to-market firm** for B2B and B2B2C founders from seed to Series B. Since 2023 he has advised 94 startups, 14 of them YC graduates. Before that, he was the first GTM hire at Lavender through Series A and led Hyperbound past Series A, after working in startups since 2010 across engineering, product, sales, and marketing. In our conversation, we discuss: 1. Why most startup AI experiments fail, and why the pressure to adopt every new tool is the real problem 2. His rule for every founder: the tool is the last decision you make, after the goal and the problem 3. Why fully automated, customer-facing AI keeps failing, and the two things that make AI work: a human in the last step and a deep well of context 4. Why middle management is the layer getting hit first, with one manager now running fifteen people where it used to be six 5. Why the dot-com comparison only goes so far: the internet gave us a new place to work, and AI is promising to do the work 6. What to do when the pace of change outruns your nervous system: narrow your information channels, pick a lane, and stay close to other founders **Where to find Josh:** LinkedIn: linkedin.com/in/joshnorris **Where to find Vlad:** Website: vladmoskovski.com LinkedIn: linkedin.com/in/vladmoskovski **Free Somatic Intelligence Toolkit for Leaders** AI gives everyone data. The leaders who stand out also listen to their body's intelligence. Download the free toolkit here: vladmoskovski.com/handbook-landing-page **Timestamps:** 00:00 Cold open: the part of the manager's job that's disappearing 00:35 Welcome and introduction 00:52 The pressure on founders to adopt AI fast, and why most experiments fail 02:56 Opening Claude Code to build something, then scrapping it a week in 05:14 The tool is the last decision you make 06:09 Vlad's bracket framework: zooming out to the biggest goal 08:11 Where AI applications fail (content, AI SDRs, pitch decks), and the two things that make it work: a human in the last step and a deep well of context 13:47 The new skills AI is asking of people 14:54 The dot-com comparison, and why AI is different 19:44 Vlad's theory: discernment and zooming out become the skills that matter 21:01 Middle managers are the layer getting hit first 23:37 Where the flattened managers go 24:17 Overwhelm, and the sense that no one can keep up 25:11 "Get used to it": the world won't slow down 27:05 How to cope: filter your information, pick a lane, stay near other founders 32:45 His greatest hope: empathy, Disclosure Day, and universal basic income 39:46 What capitalism was meant to do 41:51 Closing

2. 

   25 Sept 2026

   Smoke to Fire: CFO Lessons on Not Letting Fear Win | Andrew Platt (CFO, Strategy & Finance)

   **Andrew Platt is a CFO who leads finance teams at mid-market professional and field services companies**, where he builds the AI-powered tools his team runs on. Last quarter his team cut its monthly close time by 30% by writing its own automation rules. Before that, he spent twenty years in events, lighting shows for five U.S. Presidents and two Popes, and started out as a paralegal on a Supreme Court case. In our conversation, we discuss: 1. Why AI at any company bigger than a five-person startup is enterprise transformation, and why it needs a PMO, a stakeholder council, and clean data before anything else 2. The data problem nobody budgets for: when Andy P, Andrew Platt, and Drew Platt show up as three different people in your time-entry system 3. Smoke to fire: how to tell work that looks busy from work that produces something, and what happens to "Betty in accounting" when AI absorbs 80% of her tasks 4. The CFO reframe on the layoff headlines: if AI makes your people 40% more efficient and you cut 40% of them, you've announced you have no growth plan 5. Three things AI still does poorly: reasoning in volatile, ambiguous conditions, judgment calls built on twenty years of context, and ethics 6. AI slop, the Starbucks latte, and why craft is where the value goes next 7. What "AI maxing" actually means: fifteen minutes on the patio thinking through a decision, not fourteen more analyses 8. Why fear wins by default, what the CEO, the C-suite, and department leaders each have to say out loud to stop it, and the line between leading and managing **Where to find Andrew:** LinkedIn: linkedin.com/in/andrewdavidplatt (https://linkedin.com/in/andrewdavidplatt) Website: andrewplatt.com (https://andrewplatt.com) **Where to find Vlad:** Website: vladmoskovski.com (https://vladmoskovski.com) LinkedIn: linkedin.com/in/vladmoskovski (https://linkedin.com/in/vladmoskovski) **Free Somatic Intelligence Toolkit for Leaders** AI gives everyone data. The leaders who stand out also listen to their body's intelligence. Download the free toolkit here: vladmoskovski.com/handbook-landing-page (http://vladmoskovski.com/handbook-landing-page) **EPISODE LINKS:** Spotify: Vlad on Leadership on Spotify https://open.spotify.com/show/033z600k53oJJi7CneGCed?si=5cc9vvfCSZmmf_cExjm8Vg&utm_source=copy-link&nd=1&dlsi=b9fa939ffd154488 (https://open.spotify.com/show/033z600k53oJJi7CneGCed?si=5cc9vvfCSZmmf_cExjm8Vg&utm_source=copy-link&nd=1&dlsi=b9fa939ffd154488) Apple Podcasts: Vlad on Leadership on Apple Podcasts https://podcasts.apple.com/us/podcast/vlad-on-leadership/id1896931445 (https://podcasts.apple.com/us/podcast/vlad-on-leadership/id1896931445) Timestamps: 00:57 Welcome 01:03 What a CFO should do first with AI, and what not to do 02:14 Why clean data comes before anything else 04:58 Smoke vs. fire, and the Betty in accounting problem 07:59 IKEA's reskilling move and the fear of job loss 08:59 You can't cut your way to success 10:58 Pulling four days out of the monthly close 12:05 What stays human: reasoning, judgment, ethics 18:48 Monuments Men and ethics under pressure 20:20 AI 2027 and who gets to choose the speed 24:10 AI slop, Starbucks, and why people want the real thing 28:40 Craft and mastery: the Tokyo sushi counter 31:48 Clearing the calendar for work only you can do 35:05 What "AI maxing" actually means 36:35 The smoke to fire ratio 42:04 Fear wins unless leaders talk about it 44:51 Leaders vs. managers

3. 

   15 Sept 2026

   The Paradigm Shift of the Vibe-Coding C-Suite | Jamin Brazil | COO Parsec Education

   Jamin Brazil is the COO at Parsec Education, where his team turns student outcome data into dashboards superintendents can act on. He's a 3x founder and 4x exit operator, best known for building Decipher, now used by 75% of the Fortune 500, and running the #1 market research podcast for a decade. He hosts Jamin's Podcast, interviewing founders and operators including the former head of strategy at Publicis and a CMO of American Express. In our conversation, we discuss: 1. Why the real moat moved from the interface to the data and judgment behind it, and what that means for companies that spent decades building the UI layer AI just commoditized 2. The exact moment his CEO opened Claude Code mid-meeting and built the dashboard everyone had been debating for weeks, and why it left the room humbled instead of relieved 3. Why treating AI like a vending machine (put in the goal, expect the outcome) fails the same way an un-scaffolded new hire fails, and the fix that actually works 4. The heart attack he had on February 7th, and how he and his wife used AI to translate his diagnosis and medications when he couldn't advocate for himself 5. What he hopes his kids inherit in a world where AI hands out more validation than most humans ever will Where to find Jamin: LinkedIn: linkedin.com/in/jaminbrazil (http://linkedin.com/in/jaminbrazil) Jamin's Podcast: bit.ly/jamins-vlad (http://bit.ly/jamins-vlad) Where to find Vlad: Website: vladmoskovski.com (http://vladmoskovski.com) LinkedIn: linkedin.com/in/vladmoskovski (http://linkedin.com/in/vladmoskovski) Free Somatic Intelligence Toolkit for Leaders AI gives everyone data. The leaders who stand out also listen to their body's intelligence. Download the free toolkit here: vladmoskovski.com/handbook-landing-page (http://vladmoskovski.com/handbook-landing-page) Timestamps: 00:00 Cold open 00:56 Welcome and introduction 01:43 The pattern across three tech waves 02:57 The new moat: data and judgment replace the UI 05:28 Why leaders are afraid to admit it, and SaaS multiples in free fall 07:58 Tech-enabled services, and whether everyone becomes the expert 11:31 Knowledge vs. experience, and AI's scaffolding problem 13:06 The CEO who vibe-coded the dashboard live in a meeting 17:00 What it means for the C-suite when everyone can build 19:59 Reconciling "slow down and plan" with "just build and iterate" 22:50 Aging, AI, and his heart attack 31:29 Boardy: an AI built entirely on trust 36:11 The vending machine problem, and managing AI like a new hire 40:31 Meta-thinking: giving AI objectives so it doesn't drift 44:01 Closing thoughts: what he hopes his kids inherit

4. 

   9 Sept 2026

   Automating Main Street | Logan Shimmer | Founder of Shimmer Labs

   Logan Shimmer is the founder of Shimmer Labs, an AI automation consultancy helping Main Street businesses in Stillwater, Oklahoma automate the work they dread without losing what makes them human. He's built AI courses for Oklahoma State University and local technical colleges, and runs free weekly office hours where anyone in town can walk in and ask him anything about AI. Before that, he spent 15 years building automation across manufacturing, marketing, and the energy grid. In our conversation, we discuss: 1. Why he builds a harness around AI instead of a fully autonomous pipeline, and why the companies behind ChatGPT, Claude, and Gemini have no incentive to tell you that 2. Running bi-directional retros with his own AI agents, what one of them told him about his productivity, and why he calls them his "innies" 3. The real story behind automating a yoga studio owner's cancellation process, and what she got back that had nothing to do with software 4. Why "yes, and" from an improv class became his best tool for resetting client expectations about what AI can and can't do 5. What's left for humans once the routine work is gone, and why he thinks trust, connection, and creativity get more room to grow, not less 6. His five-part prompt framework (role, context, task, format, constraints) and the one part most people skip LOGAN LINKS: LinkedIn: https://www.linkedin.com/in/loganshimmer/ (https://www.linkedin.com/in/loganshimmer/) Website: shimmerlabs.co (http://shimmerlabs.co) VLAD LINKS: Website: vladmoskovski.com (http://vladmoskovski.com) LinkedIn: linkedin.com/in/vladmoskovski (http://linkedin.com/in/vladmoskovski) Free Somatic Intelligence Toolkit for Leaders AI gives everyone data. The leaders who stand out also listen to their body's intelligence. Download the free toolkit here: vladmoskovski.com/handbook-landing-page (http://vladmoskovski.com/handbook-landing-page) EPISODE LINKS: Spotify: https://open.spotify.com/show/033z600k53oJJi7CneGCed?si=5cc9vvfCSZmmf_cExjm8Vg&utm_source=copy-link&nd=1&dlsi=b9fa939ffd154488 (https://open.spotify.com/show/033z600k53oJJi7CneGCed?si=5cc9vvfCSZmmf_cExjm8Vg&utm_source=copy-link&nd=1&dlsi=b9fa939ffd154488) Apple Podcasts: https://podcasts.apple.com/us/podcast/vlad-on-leadership/id1896931445 (https://podcasts.apple.com/us/podcast/vlad-on-leadership/id1896931445)

5. 

   7 Aug 2026

   Technology Moves Faster Than We Can Decide | Itai Green (Open Innovation Expert)

   Itai Green is the founder of an open innovation consulting firm, where he helps corporations and governments run innovation programs with startups. He spent 15 years as an entrepreneur before heading innovation for Amadeus in Israel, and has since run open innovation with hundreds of organizations worldwide. His book, Innovation or Elimination: Winning in a World of Constant Change, published in May 2026. In our conversation, we discuss: Why the pace of technological change now moves faster than most corporate decision making, and what has to change about how executives decide Why 95 percent of failed corporate-startup pilots have nothing to do with the startup failing to deliver Inside his bootcamp process: from three ranked priorities per VP, to ten shortlisted startups, to two pilots, to one integration Why board incentives built entirely on quarterly P&L are the real block on innovation Why he treats every employee as a sensor for the next disruption, and the shift from ego to curiosity that comes with it His advice to corporate VCs: pilot before you invest, because a pilot is the best due diligence money can buy Itai Links: LinkedIn: linkedin.com/in/itaigreen (http://linkedin.com/in/itaigreen) https://www.globalinnovationandstrategy.com/ (https://www.globalinnovationandstrategy.com/) https://www.linkedin.com/in/itaigreen/ (https://www.linkedin.com/in/itaigreen/) Book: Innovation or Elimination: WINNING in a World of Constant Change. An Executive Playbook (https://www.amazon.com/dp/1606494961?lv=shuf&channelId=500&plpRedirect=mhFallback) Vlad Links: Website: vladmoskovski.com (http://vladmoskovski.com) LinkedIn: linkedin.com/in/vladmoskovski (http://linkedin.com/in/vladmoskovski) Free Somatic Intelligence Toolkit for Leaders AI gives everyone data. The leaders who stand out also listen to their body's intelligence. Download the free toolkit here: vladmoskovski.com/handbook-landing-page (http://vladmoskovski.com/handbook-landing-page) Timestamps: 00:00 Welcome and introduction 00:47 Itai's path: entrepreneur, then head of innovation at Amadeus, to founding his own open innovation firm 02:16 The real bottleneck in corporate innovation, and why it isn't finding the right startups 03:33 Why corporate and startup cultures move at completely different speeds 06:05 How three and a half years of AI acceleration made his job easier 08:01 What it costs leaders to let go of the operating model that made them successful 10:16 Speed of decisions versus slowing down for strategy: comparing notes with Vlad 11:54 Treating the ecosystem as a threat or an opportunity, and what McKinsey can't see 17:01 Why board incentives built around quarterly P&L are the real blocker 19:10 Inside the bootcamp: from three ranked priorities per VP to one integration 22:31 Why 95 percent of failed pilots aren't the startup's fault 23:07 Vetting a startup partner like a marriage, not a vendor contract 25:19 What changes in a leader once open innovation works: curiosity over ego 40:19 Closing: let's go make miracles happen

6. 

   3 Aug 2026

   The Identity Crisis Nobody's Naming, with Annie Tsai

   Annie Tsai is Chief Operating Officer at marketing technology company Interact, where she has spent 25 years building, growing, and scaling software companies. She also serves as COO of Moms in Tech, a global community of over 19,000 working mothers in the industry, and writes two weekly columns on technology and AI. Before this, she spent more than fifteen years leading customer experience and cross-functional teams from the C-suite. In our conversation, we discuss: Why the shift from orchestrating work to actually executing it herself is creating a very real identity crisis, and not just for junior workers The real cost of running twenty concurrent strategic initiatives without gaining any personal capacity, and the systems she had to build, then open source, just to keep track of it all What she had to let go of to get here: the clout that comes with a title, and the belief that time served still earns you anything Why taste and craft, not raw skill, is what separates someone with institutional knowledge from a new grad using the same AI tools Why almost nobody in a room full of early AI adopters knew what "planning mode" was, and what that reveals about how most people are still using AI wrong Why she thinks this identity crisis might finally break America's habit of letting work define who we are Where to find Annie: Personal: annietsai.co (http://annietsai.co) momsintech.com (http://momsintech.com) Where to find Vlad: Website: vladmoskovski.com (http://vladmoskovski.com) LinkedIn: linkedin.com/in/vladmoskovski (http://linkedin.com/in/vladmoskovski) Free Somatic Intelligence Toolkit for Leaders AI gives everyone data. The leaders who stand out also listen to their body's intelligence. Download the free toolkit here: vladmoskovski.com/handbook-landing-page (http://vladmoskovski.com/handbook-landing-page) Timestamps: 00:00 Introduction, and why work now means holding twenty conversations at once that never end 00:58 Who Annie Tsai is: COO at Interact, Moms in Tech, and her upcoming third book 02:44 The premise behind her column: a generation trained to become one expert thing, now disrupted 04:27 From orchestrator to executor: how her actual role changed over the last few years 08:21 The cognitive cost of running twenty strategic initiatives at once, and the systems she built to survive it 10:43 What she had to let go of: the clout that comes with a title 12:20 Taste and institutional knowledge as the real differentiator AI can't replace 17:15 Her hope for the American workforce: that what we do stops being who we are 18:24 The grief of losing a skill you used to love, and why it deserves to be named as grief 20:47 Painting murals, and finding the time to fill the buckets that make you feel like yourself 21:55 Advice to her thirteen year old son on what to study and why 25:10 Creativity as the new white picket fence 29:58 Metacognition as the most underrated AI skill, and why almost nobody in the room knew what planning mode was 32:32 Why "AI native" is the wrong hire, and what to look for instead 35:35 Modeling AI use as a leader, and the CEO who built the dashboard instead of just talking about it 36:30 Closing: what people will be pleasantly surprised to evolve into

7. 

   27 Jul 2026

   Get Comfortable With Your Discomfort | Berk Algan (SVB, Ernst & Young, vCISO)

   Berk Algan is the founder of Virtual Cyber Risk Office, where he works as a fractional CISO and Chief Compliance Officer for growth-stage companies. He built the security and risk function at Silicon Valley Bank from the ground up over more than a decade, growing it to a team of 40 as the bank scaled to $200 billion. Before that, he audited Google, Apple, and Facebook at Ernst & Young, and left corporate for good in 2023. In our conversation, we discuss: Why the first wave of AI hit structured, repeatable knowledge work first, and what the next wave (the review layer) is already coming for The compression trap: how AI shrinks the time it takes to do the work while the scope quietly expands to fill the gap, so people end up working more, not less Why more AI tools and more options are creating more decision fatigue, not less, and what that means for how you decide anything right now What actually separates people who adapt well from people who don't, and why it has less to do with skill than most advice suggests His three-part response to this moment: get closer to the actual business problem, protect the right things instead of the familiar things, and use your own unsettledness as fuel instead of something to fix What he'd say to a technical leader who feels the ground moving and doesn't know where they're headed yet Where to find Berk: LinkedIn: linkedin.com/in/berkalgan (http://linkedin.com/in/berkalgan) Website: virtualcyberriskoffice.com (http://virtualcyberriskoffice.com) Where to find Vlad: Website: vladmoskovski.com (http://vladmoskovski.com) LinkedIn: linkedin.com/in/vladmoskovski (http://linkedin.com/in/vladmoskovski) Free Somatic Intelligence Toolkit for Leaders AI gives everyone data. The leaders who stand out also listen to their body's intelligence. Download the free toolkit here: vladmoskovski.com/handbook-landing-page (http://vladmoskovski.com/handbook-landing-page) Timestamps: 00:00 Welcome and introduction 01:00 The three waves of AI hitting knowledge work 04:30 Why more options are creating more decision fatigue 09:30 The compression trap: doing more, not less 14:40 Overwhelm, burnout, and the case for human flourishing 26:40 Choosing optimism without ignoring what's real 29:25 Life design and finding gratitude in the noise 30:25 Why he left corporate, and what made the leap possible 35:20 Relationships as the real currency after corporate 37:10 Get closer to the business problem 41:45 T-shaped vs. Z-shaped: what to actually get deep in 45:15 Closing line: get comfortable with your discomfort

8. 

   27 Jul 2026

   Why AI Can't Replace Your Judgment Yet | JD Margulici (Cruise)

   JD Margulici is a technologist with more than twenty years of experience building information technology for transportation, industrial automation, and autonomous driving. He cofounded Vehicle Data Science in 2013, pioneering the use of connected fleet data to build high-definition maps, and later served as CTO at Infinite Uptime and a senior staff engineer at Cruise. Before that, he trained in mathematics and physics at Ecole Polytechnique in Paris, then earned a master's in transportation engineering and an MBA at UC Berkeley. In our conversation, we discuss: How AI has shifted from an autocomplete assistant to the default first move in his day to day coding and design work, and what that shift costs in terms of owning your own knowledge Why raw intuition and taste, not access to tools, is what now separates good work from bad, since everyone has access to the same AI The real bottleneck in software engineering: not writing code, which is under 20 percent of the job, but interpersonal communication, translating vision into requirements into architecture into code A cautionary story about two AI-written memos on his team's wiki that sounded confident but didn't hold up, and why he chose not to argue with an AI's reasoning Physical AI and the "floating brain in a tank" problem: why language-only intelligence still lacks a toddler's intuition for how the physical world works, and what robotics could change The structured to unstructured to structured pattern that makes AI agents actually useful, and why he's still unsure what to tell his own kids about their future Where to find JD: LinkedIn: https://www.linkedin.com/in/jdmargulici/ (https://www.linkedin.com/in/jdmargulici/) Where to find Vlad: Website: vladmoskovski.com (http://vladmoskovski.com) LinkedIn: linkedin.com/in/vladmoskovski (http://linkedin.com/in/vladmoskovski) Free Somatic Intelligence Toolkit for Leaders AI gives everyone data. The leaders who stand out also listen to their body's intelligence. Download the free toolkit here: vladmoskovski.com/handbook-landing-page (http://vladmoskovski.com/handbook-landing-page) Timestamps: 00:00 Introduction, and being the first ever podcast guest 00:46 How the day to day of coding and design has shifted with AI in the past year 01:54 Democratized tools, and what actually separates good work from bad now 04:11 Why interpersonal communication, not code, is software engineering's real bottleneck 07:24 The AI-written memos on the wiki that didn't hold up 09:34 AI slop, and the flood of easy to generate, hard to evaluate content 13:07 Guardrails, and hoping the growing pains are just transitional 14:29 Physical AI, digital twins, and managing real-world infrastructure 16:58 The "floating brain in a tank" without senses 19:30 Representations, notation, and why code is often the most precise language 23:11 The structured to unstructured pattern that makes AI agents work 26:10 Closing thoughts: feeling clueless, parenting, and what to tell his kids about the future

9. 

   25 Jul 2026

   How AI Shapes Human Identity and Flourishing | Swapnil Shrivastava (Adobe)

   Swapnil Shrivastava is a product leader at Adobe, where he works at the intersection of AI, creativity, and product strategy. He has spent over 23 years at Adobe, moving from engineering into design and product leadership, and today leads agentic imaging and AI-powered creative workflows for Adobe Express. Before that, he helped shape Adobe's creative tools from the ground up, and outside of work he studies Indian classical music and the bansuri. In our conversation, we discuss: Why AI is, at the core, nothing more than next word prediction, and why that fact does not make what is coming any less real Why running an AI agent has gotten as addictive as coding used to be, and what that says about attention and control What is actually left of a person's identity once AI can do most of the doing: judgment, taste, and the ability to set the objective the model is chasing Why training everyone on the same intelligence risks making all of us more similar, not more capable Why the loneliness cost of an AI-driven work life worries him more than losing a job, and what the old studies on touch and love still prove What he tells his teenage son, who wants to be a DJ instead of a coder, and the project he is building to teach AI how to carry Indian classical music forward Where to find Swapnil: LinkedIn: linkedin.com/in/swapnil-shrivastava-2b493637 (http://linkedin.com/in/swapnil-shrivastava-2b493637) Where to find Vlad: Website: vladmoskovski.com (http://vladmoskovski.com) LinkedIn: linkedin.com/in/vladmoskovski (http://linkedin.com/in/vladmoskovski) Free Somatic Intelligence Toolkit for Leaders AI gives everyone data. The leaders who stand out also listen to their body's intelligence. Download the free toolkit here: vladmoskovski.com/handbook-landing-page (http://vladmoskovski.com/handbook-landing-page) Timestamps: 00:00 Introduction, and why AI is just next word prediction 01:09 The story behind the background: Adobe's decades-old office puzzle tradition 04:43 Inside Adobe's "code red" moment on AI 07:46 AI alignment and the idea of human flourishing 09:36 Why running an agent while playing flute felt so addictive 13:28 What is left of identity when AI can do most of the doing 16:40 Taste versus judgment, and reading thought directly 19:23 The patterns AI can learn, and who Swapnil is outside them 20:23 Man as the measure of everything, and Sam Altman's line about kids never outsmarting ChatGPT 23:14 The Nigerian call center story behind ChatGPT's word choices 25:23 Advice to his teenage son, who wants to be a DJ 27:51 The orphanage studies on touch, love, and what people actually need to survive 29:19 The loneliness epidemic, and why it worries him more than job loss 32:54 Manifesting the future: teaching AI to carry Indian classical music forward 35:37 Closing line: "May there be resonance"

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