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Ten Thousand Miles: Daily Summaries Delivered
by Vic Pepe
I interview people who "make it look easy" but leave it all on the field daily to do so.
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- Yesterday1h 8m
The Hidden Opportunity Most People Never See | Anna Stallman
We're back with another episode of Ten Thousand Miles, and today I'm incredibly lucky to sit down with Anna Stallmann, founder of Ascent Strategic Communications. Whether you're a CEO trying to build influence, a founder considering a rebrand, or a professional wondering if you should start a podcast — this episode is for you. CHAPTERS 00:00 Welcome and Introduction to Anna Stallmann 05:00 From the U.S. Senate to the Department of Defense 16:00 Launching Ascent Strategic Communications 19:00 The First 90 Days of Entrepreneurship 26:00 Strategy Over Noise 33:00 Should You Start a Podcast? 40:00 The Rebrand 44:00 People First Leadership 51:00 Personal Brand vs. Company Brand 58:00 Rapid Fire KEY TAKEAWAYS * The most underrated communication move: know your white space — the message only YOU can deliver * Visibility is not influence. Influence is built through trust, discipline, and messengers * "Plans are worthless, but planning is everything." — General Eisenhower * Be famous internally first — with your family, your team, your community * Hard work ethic still builds the best leaders. Fame that is earned lasts * It doesn't matter what you say. It matters what people hear GUEST RESOURCES Ascent Strategic Communications: https://ascentcomms.com/ Book Recommendation: Made to Stick by Chip and Dan Heath #StrategicCommunications #PersonalBranding #Leadership #Entrepreneurship #TenThousandMilesPodcast #PublicRelations #CEOBranding #WhiteSpace #CommunicationsStrategy #PodcastInterview Please Comment, Like, Share, and Subscribe! Guest: Anna Stallmann
- 1 weeks ago46 min
AI First Enterprise: See Everything & Know Everything
What does it actually look like when a CIO walks into a 20-year-old technology organization and turns it AI-first in under 12 months — without shutting anything down? In Part 3 of the Sage Tech series on Ten Thousand Miles, Vic Pepe sits down with Corey Kirspel, a transformational CIO in the healthcare technology space. This is not theory. This is a boots-on-the-ground account of one of the most compelling enterprise modernization stories in the AI era. Corey walked into a private equity portfolio company three years into a five-year hold — facing a 12-million-line legacy code base, a $2M cost reduction mandate, tribal knowledge locked inside a handful of people, and a board demanding an AI-first strategy. Here is what happened next. What you'll learn: * Why Claude, Copilot, and Cursor weren't enough alone — and what Corey layered on top * How Sage Tech mapped 12 million lines of legacy code in 48 hours — architecture, vulnerabilities, and evergreen documentation included * The one-engineer experiment that turned skeptics into believers — a five-month project done in six weeks * How $1.2M in annual infrastructure savings was unlocked in three months without a ground-up rewrite * The SDLC operating model shift that took a team from 100 lines of code per day to 10,000 * What the first 90 days of AI transformation actually looks like — and how to justify the ROI fast Whether you are a CIO, CTO, PE operating partner, or business leader trying to move from talking about AI to executing it — this episode is required listening. Chapters: 00:00 — Welcome and guest introduction 02:00 — The CIO's real job in the AI era 03:53 — Walking into a PE portco with a 20-year-old code base 05:25 — Why Claude, Cursor, and Copilot weren't enough alone 08:15 — Discovering Sage Tech and the virtual architect model 12:04 — Breaking free from tribal knowledge and key-man dependency 19:34 — The product leader who thought she knew her own system 22:04 — The one-engineer experiment that changed everything 33:49 — From one engineer to eight Scrum teams — the rollout strategy 42:01 — First 90 days and a message for anyone still waiting Connect: * Sage Tech AI: https://www.sage-tech.ai * Subscribe for new episodes every week Keywords: enterprise AI transformation, CIO strategy, legacy code modernization, AI-first enterprise, Sage Tech AI, software modernization, technical debt, private equity portco, healthcare technology, SDLC AI integration, CIO podcast, technology leadership, AI tools for developers, code base analysis, digital transformation ROI
- 2 weeks ago39 min
Is This AI a Real Game Changer?
Join us as we sit down with Bruce Henderson, CTO of Sage-Tech.ai, to get an in-depth look at their platform and the #technology driving it. This conversation provides valuable insights into the technical operations and #leadership involved in their enterprise #aistrategy. Stay updated with the latest AI news and gain a deeper understanding of how AI is explained in practical applications. Bruce built his career maintaining, upgrading, and retiring the massive legacy systems that sit at the heart of the global economy. In this conversation, he pulls back the curtain on how Sage Tech actually works — from the queryable context graph and cognitive model to the AI inference layer, ephemeral environments, and why vector RAG failed them before they built something better. This is one of the most technically honest conversations about enterprise AI you will hear anywhere. No hype. No sales pitch. Just a veteran engineer telling you exactly what works, what does not, and what every CTO needs to understand before 2030. Learn more about Sage Tech: https://sage-tech.ai Miss Part 1? Watch the business track with Deepak Sharma here: [link] CHAPTERS 00:00 Introduction — Why Bruce Built Sage Tech 04:01 From Code to Knowledge — The Pivot That Changed Everything 08:07 The Queryable Context Graph Explained 10:15 Why Vector RAG Failed and What Replaced It 14:03 How the Graph Gets Built From a Real Code Base 17:14 Outputs, Documentation, and Self-Service Intelligence 24:04 Scaling From 500K to 15 Million Lines of Code 28:44 Ephemeral Environments and the Future of AI Coding LIGHTNING ROUND 38:33 Most Overrated Thing in Enterprise AI 39:16 The Underrated Risk Nobody Is Talking About (De-skilling) 40:09 Bruce's Favorite Tool Most People Have Never Heard Of 41:12 What He Would Do Differently Building Sage From Scratch 42:42 The One Thing Most CTOs Still Do Not Believe About AI in 2026 Subscribe so you never miss an episode. Please Like, Comment, Share, and Subscribe We sit down with Bruce Henderson, CTO of Sage-Tech.ai, for an in-depth discussion on their platform and its core technology . This episode offers key insights into technical operations and the enterprise ai strategy driving their work. Discover how their innovation is shaping the future of AI.
- 3 weeks ago33 min
The Insane Enterprise AI Nobody Is Talking About!
In this insightful podcast discussion, we dive deep into artificial intelligence technologies, exploring how ai works and its significant impact. Vic and Depak offer a comprehensive AI explanation for beginners, highlighting the future of AI. This episode provides valuable perspectives on the evolving landscape of technology. What happens when enterprises try to modernize decades of legacy code — and fail? In Part 1 of this conversation, Vic Pepe sits down with Deepak Sharma, a veteran transformation advisor who has guided some of the world's largest financial institutions and insurance organizations through their most complex technology challenges. Together they explore why legacy modernization almost always goes over budget, over schedule, and under-delivers — and how a new AI-powered tool called Sage Tech (sage-tech.ai) is changing the equation entirely. Deepak walks through how Sage ingests entire code bases in hours (not years), builds a living data model of how systems actually work, and gives business leaders, engineers, and compliance teams a visual map of technical debt, security risks, and organizational dependencies — across every application in the enterprise. Whether you're a CIO navigating a legacy estate, a CTO trying to separate commodity code from differentiated IP, or a transformation leader tired of projects that never finish — this episode will reshape how you think about what's possible. Learn more about Sage Tech: https://sage-tech.ai CHAPTERS 00:00 Introduction — Why Legacy Modernization Fails 03:02 Meet Deepak Sharma — Transformation at Scale 04:17 What Is Sage Tech and How Was It Discovered 07:30 How Sage Ingests and Maps a Code Base 09:28 Hours vs. Years — The Speed Advantage of AI 11:13 Connecting All Your Systems — The Enterprise View 15:04 The New Engineer — System Thinkers Over Coders 17:14 CFOs, COOs, and the Business Case for Modernization Ten Thousand Miles is hosted by Vic Pepe — Managing Partner of D&M Enterprise Group, co-author of The RFP Is Dead, and a veteran technology executive with stops at Bear Stearns, Lehman Brothers, and JPMorgan Chase. Every episode goes deep with founders, executives, operators, and innovators who are building, leading, and transforming at the highest levels. Subscribe so you never miss an episode. #LegacyModernization #AITransformation #EnterpriseTechnology #TechLeadership #SoftwareModernization #CIO #CTO #DigitalTransformation #ArtificialIntelligence #TechnicalDebt #LargeLanguageModels #AIStrategy #EnterpriseAI #TenThousandMiles #VicPepe #DeepakSharma #SageTech #FinancialServices #CloudMigration #ApplicationModernization Please Comment, Like, Share, and Subscribe!
- 4 weeks ago27 min
The Business Mistake Nobody Wants to Admit
In this insightful clip, the speaker discusses his book "The RFP is Dead" and explains what truly led to the demise of the traditional request for proposal process. He sheds light on the new landscape of business proposal and procurement, emphasizing what has replaced the old methods. This discussion offers a valuable perspective for anyone interested in business education and the evolution of contract management. Procurement is broken. The Request for Proposal — a process that dates back to the 1800s — is costing buyers and sellers millions of dollars in wasted time, bloated documents, and theater. In this episode, Vic Pepe breaks down exactly why the RFP died, what's replacing it, and what you should do right now, whether you're buying or selling enterprise technology.If you work in procurement, sales, or enterprise technology leadership, this one will hit close to home. Get the book: The RFP Is Dead — available on Amazon for under $7 D&M Enterprise Group: www.dmenterprise.net Contact Vic: vic@dmenterprise.netIn This Episode: • Why the RFP became a compliance exercise and a cover-your-ass tool • The 4 forces that killed the RFP • How AI is now writing — and scoring — RFPs on both sides of the table • Why "if you didn't shape it, you've already lost" is the new rule • What trusted advisors do that RFPs never could • The history of the RFP (yes, it started in the 1800s) • What buyers and sellers should actually be doing right now Chapters: 00:00 Introduction — Vic's book and why he's passionate about this 01:45 Procurement Is Broken — the 4 reasons the RFP died0 3:30 The RFP as a CYA exercise — real stories from the C-suite 04:45 What replaced the RFP — trusted advisors, POCs, peer networks 06:30 The "already won" model — why cold RFPs are a waste of time 08:00 AI vs. AI — how automation is killing the RFP even faster 10:15 The new currency: authority, trust, and relationships 12:00 D&M's authority gap event and the AI leadership divide 13:00 If you're selling — stop chasing RFPs you didn't shape 15:00 Be the advisor, not the vendor 15:45 If you're buying — the RFP protects procurement, not the business 17:00 History of the RFP — from 1800s newspapers to today 19:30 Public sector, the veil of equality, and backdoor channeling 21:00 Failure, fear, and corporate paralysis 22:30 Internal sabotage — what happens when people don't want change 24:00 The 3 things you actually need to know before selecting technology 26:30 What trusted advisors expose that RFPs never can 27:30 Closing — get the book, get a trusted advisor, go execute Please Comment, Like, Share, and Subscribe!
- May 12, 202635 min
The Addiction Nobody Warns You About | Climbing Edition
Ever felt that rush? I remember that first time, the pure dopamine hit of climbing, a powerful form of motivation that felt like a true addiction. This experience wasn't about drugs, but about the sheer happiness found in pushing limits. It's a great life lesson in self improvement. Everyone wants to climb the ladder. But do you know why you're climbing and what it's going to cost you? In this raw, honest solo episode, Vic breaks down one of the most important questions in leadership, business, and life: What is the ladder of success, and is it worth the climb? Drawing on a career that spans the music business (Alice Cooper), Lehman Brothers, Bear Stearns, JP Morgan Chase, five CIO roles, and executive advisory work, Vic shares the neuroscience behind status-seeking, the psychology of ambition, and the very real sacrifices high achievers make on the way to the top. This isn't motivational fluff. This is the truth about what success actually demands. In this episode: * Why your brain is hardwired to chase status (dopamine, serotonin, and survival hierarchies) * The difference between ambition as identity vs. ambition as expression * How to know if you're climbing the wrong wall * The trades every high achiever makes: relationships, health, faith, and presence * Why climbing fast and climbing right are two very different things * The identity collapse that happens when the badge is gone * How to raise yourself by raising others * Why are the most successful leaders the ones who bring people with them Key Concepts Discussed: Victor Frankl on purpose | Maslow's hierarchy of needs | Jordan Peterson on competence hierarchies | Leon Festinger's social comparison theory | Eudaimonic well-being (Aristotle) | The EKG climb: why success is never a straight line Chapters: 00:00 The First Hit of the Ladder 03:45 Why Your Brain Is Wired for Status 07:20 The Ladder as Meaning Making Structure 10:10 The Trap Baked Into the Structure 13:30 The Boardroom Moment That Changed Everything 18:00 The Climb Is Not a Straight Line 22:15 Your Reputation Leads Before You Do 26:40 The Trades You Make on the Way Up 33:10 Identity Collapse at the Top 37:00 How to Climb and Stay Whole 40:20 Self Examination: Was It Worth It? Tags / Keywords: success mindset leadership lessons climbing the corporate ladder executive leadership career advice ambition and success work life balance CIO career what does success cost purpose driven leadership Vic Pepe Ten Thousand Miles podcast leadership podcast business podcast career growth dopamine and success status hierarchy Jordan Peterson hierarchy Maslow hierarchy of needs Victor Frankl purpose #LeadershipPodcast #SuccessMindset #CareerGrowth #TenThousandMiles #ExecutiveLeadership #Ambition #CIOLeadership #BusinessPodcast #VicPepe #climbingtheladder
- May 4, 202654 min
Behind The Scenes With Eric Gales!
Join us as we dive into the creative process of a musician who believes every performance is unique. He shares his approach to live music, emphasizing following intuition rather than a rigid song list. Discover how this artist crafts his music live, making each night a fresh experience. Guitar legend @EricGalesBand - Gales joins Vic on Ten Thousand Miles for a conversation 35+ years in the making. From picking up his first #guitar at four in a music-filled #memphis household, to signing his first record deal at 16, to his recent Oscars performance and induction into the Blues Hall of Fame — Eric shares the highs, the heartbreaks, and the inspiration that have fueled nearly five decades in music. Eric opens up about the emotional making of "Stand Up" from Crown, the gut-punch of having an early record rejected by his label, the brothers who guarded him through the industry, and the gift he believes was given to him from above. https://youtu.be/DJHLkLOFEVA?si=CcKyarH3VfZzdvCM He also gets candid about gear — Magneto, Kiesel, PRS, Dunlop, Seymour Duncan, and his Mark Bass Raw Dog signature amp — and shares hard-won wisdom about letting life be life and using music as the most powerful outlet there is. Learn more about Eric: ericgales.com Chapters * 0:00 Intro * 1:18 The Gift * 3:19 Interview Begins * 5:47 Picking Up the Guitar at Four * 18:06 The First Big Disappointment * 24:15 Crown, "Stand Up," and a Vocal for the Ages * 33:00 Life Be Life: Controlling What You Can * 51:36 Advice to His 16-Year-Old Self Keywords: Eric Gales, Eric Gales interview, Eric Gales guitar, Crown album, Stand Up Eric Gales, Blues Hall of Fame, blues guitar, rock guitar, Memphis blues, guitar legends, Ten Thousand Miles podcast, Vic Pepe, Rick Beato, Joe Bonamassa, Magneto guitars, Kiesel guitars, PRS guitars, Raw Dog amp, guitar players podcast, music industry stories. Hashtags: #EricGales #TenThousandMiles #BluesGuitar #GuitarLegends #CrownAlbum #BluesHallOfFame #RockGuitar #GuitarPodcast #MemphisBlues #StandUp #GuitarPlayers #MusicPodcast #VicPepe #GuitarInterview #BluesRock Please Comment, Like, Share, and Subscribe! #shorts #shortsfeed #podcast #leaders #stories #podcast #courage #business #Success #Leadership #Motivation #Inspiration #SelfImprovement #PersonalDevelopment #GoalSetting #Mindset #Entrepreneurship #BusinessSuccess #LifeGoals #PositiveThinking #AchieveYourGoals #SuccessMindset #LeadershipSkills #MotivationalQuotes #SuccessTips #LeadershipDevelopment #InspirationalVideos #SuccessStories #money #life #rockandroll #music #CEO #COO #CFO #CAO #nextjob #goodtimes #success
- Apr 27, 20261h 12m
The Symbolic Reasoning Breakthrough Nobody's Talking About - Dain Ehring
In this insightful podcast, we explore the cutting-edge world of artificial intelligence with an expert in symbolic reasoning. Learn about the future of AI as we discuss various aspects of machine learning, neural networks, and the logic behind advanced systems. This conversation touches on innovation in AI, offering a glimpse into how these technologies are shaping our world. Vic Pepe sits down with #entrepreneur and innovator Dain Ehring for a powerful conversation about the future of #artificialintelligence financial services, compliance, risk, and the massive shift from the Information Age to the Intelligence Age. Dain shares his work with QGI, Quantum General Intelligence, a deterministic AI platform built for highly regulated industries like financial services, lending, compliance, underwriting, and risk management. Unlike traditional large language models, deterministic AI is designed to provide traceability, auditability, consistency, and defensible decision-making.Vic and Dain dive deep into: AI in financial servicesDeterministic AI vs generative AI Compliance risk and regulatory pressure AI hallucinations and why they matter The future of underwriting and lending How AI will impact jobs and productivity Autonomous agents and personal AI assistants The rise of user sovereignty Why AI will expose the bell curve How entrepreneurs and small businesses can use AI today 00:00 Show Teaser 00:54 Introduction to Dain Ehring & AI Background 03:24 The Problem with AI in Financial Services (Probabilistic vs Deterministic) 07:14 Real-World AI Efficiency Gains and Limitations 11:39 AI Risk, Lawsuits, and Compliance Challenges 17:04 What is Deterministic AI and Why It Matters 22:24 Use Cases: Compliance, Underwriting, and Risk Management 29:39 The Future of AI, Autonomous Agents, and Human Impact Subscribe to Ten Thousand Miles for more conversations with leaders, founders, innovators, and people shaping the future. Please Comment, Like, Share, and Subscribe!
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I interview people who "make it look easy" but leave it all on the field daily to do so.
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