Ten Thousand Miles

Vic Pepe
  • 0.0 (0)
  • Entrepreneurship
  • Updated daily

The road to success is full of hard work and determination. It is never easy - you just learn to handle hard... Here, I interview people who "make it look easy" but leave it all on the field daily to do so.

  1. 23 hr ago

    Why You're Not Lucky Yet (and how to fix it!)

    Luck, success, leadership, career growth, resilience, relationships, preparation, and opportunity. Vic Pepe explains why “lucky” people may not actually have more luck. They build a bigger landing pad for it. In this episode, I pull a lesson from my first book, The Lucky 13: The Definitive Set of Core Competencies for Great Leadership, and dig into something I've thought about for most of my career: What if you could actually increase your chances of getting lucky? I used to call myself “the luckiest guy in technology.” And I've absolutely had breaks I couldn't manufacture. I met the right people. Opportunities appeared at exactly the right moment. Doors opened that I couldn't have predicted. But that's only half the story. I believe luck becomes powerful when it meets preparation, resilience, relationships, timing, choices and the willingness to act. I share how a failed career in the music business led me to an $11-an-hour technology job, how one relationship helped change the trajectory of my career, and how relentlessly learning and expanding my skills eventually helped put me in the CIO seat. We also talk about why maintaining relationships for decades matters, why you have to take calculated risks before you feel completely ready, and why some of the worst breaks of your career can eventually become the moments you're most grateful happened. I also give you an exercise I've used for years: identify the 13 moments that made you who you are today. Don't just list accomplishments. Include the people, failures, decisions, accidents, opportunities, wins, losses and turning points. Then look for the pattern. You may discover that some of the moments you once considered incredibly unlucky were actually responsible for getting you exactly where you needed to go. You can't control when opportunity knocks. You can control whether you're home to answer the door. If this episode gave you something to think about, please subscribe and leave a comment, and share it with someone who could use this message. And tell me in the comments: What's one moment in your life that felt unlucky at the time, but turned out to be a blessing later? The Lucky 13 by Vic Pepe is available on Amazon in paperback, hardcover and eBook. Chapters 00:00 - Please Subscribe + What Does It Mean to Be Lucky? 03:05 - The Black Hawk Theory: Build a Bigger Landing Pad 04:36 - The Lucky Break That Changed My Career 09:19 - How to Create More Opportunities for Luck 11:45 - Relationships, Risk and Playing the Long Game 14:00 - When Bad Luck Is Actually Redirecting You 19:48 - The 13 Moments That Made You Who You Are 23:00 - How to Become “Luckier” in Life

  2. 25 Aug

    It’s Tough Out There – Keep Going!

    Vic and JD share personal stories from their own careers, including moments when success suddenly turned into uncertainty. They explore why we attach so much of our identity to our jobs, why losing a role can feel like losing our value, and how to separate a temporary setback from the bigger story of who we are. They also dig into the realities of today’s job market, from AI-driven resume screening and recruiter ghosting to the power of relationships, referrals, and having people willing to make a phone call on your behalf. Most importantly, this is a conversation about confidence. How do you rebuild it? How do you create new evidence that you’re still capable? When should you ask for help? And what does it actually look like to support someone who’s sitting on the bench? If you’ve been laid off, pushed out, passed over, rejected, or you’re simply questioning what comes next, this episode is for you. You lost a job. You didn’t lose your value. CHAPTERS 00:00 — When Your Career Knocks You Down 05:09 — Your Job Is Not Your Identity 11:00 — Surviving Setbacks & Owning Your Story 23:38 — Confidence Is Built, Not Given 29:59 — The Job Search Is Broken 40:11 — Stop Applying. Start Working Your Network. 46:57 — Asking for Help & Actually Helping Others 56:39 — Your Setback Might Be Your Next Beginning Whether you’re actively searching for your next opportunity or helping someone who is, remember this: One bad chapter doesn’t erase the entire story.

  3. 18 Aug

    The Buy vs. Build Trap: What I Wish I Knew as a CIO (earlier).

    Everyone faces embarrassing moments when starting out, but these experiences often shape our future trajectory. This discussion focuses on reframing failure and finding the value in those awkward early career lessons. If you feel stuck comparing your beginning to someone else's middle, this perspective on professional growth will help you reset your expectations. We explore why adopting a progress over perfection attitude is essential for long-term success. By looking at how minor setbacks serve as building blocks, you can approach your daily work with more confidence. Whether you are navigating your first job or pivoting to a new industry, embracing these career lessons helps you move forward without the weight of past errors. Subscribe for weekly career advice breakdowns, and let me know in the comments: what is one mistake you made that taught you a valuable lesson? Chapters: 00:00 – Intro: The Embarrassing Story From My First Strategy Meeting 04:47 – Why CIOs Don't Need a Team — They Need an Army 09:32 – The Data Doesn't Lie: IT Project Failure Rates 13:58 – AI Is Becoming a Commodity — Stop Trying to Build It 18:32 – The Real Cost of Building In-House 24:07 – How to Buy Smart: A Framework for CIOs Referenced in this episode: Vic's LinkedIn paper, "What I Wish I Knew as a New CIO." https://www.linkedin.com/posts/vic-pepe_a-30-year-look-back-activity-7490739364658860032-XeFX?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAB0zZUB4hhw7iJ4uEsh5eZZF3GNL-u_kIo

  4. 11 Aug

    AI Didn't Replace Us, It Multiplied Us! | Jason Tanaka

    Technology leadership requires more than just code. Learn how to balance serious decision-making with genuine joy. Sit down with Jason Tanaka, a fellow technologist and leader, as we break down the realities of managing technical teams. This conversation moves beyond standard management theory to focus on the human side of engineering management, exploring how we maintain authenticity while navigating high-stakes projects. We discuss the specific challenges of career growth in the current landscape. By examining our own experiences—from serious strategy sessions to lighter, joyful exchanges—we highlight how technical mentorship and building strong workplace dynamics can define your trajectory. You will walk away with a clearer understanding of how to lead with both competence and character. Subscribe for weekly technology leadership breakdowns, and let me know your biggest management hurdle in the comments. CHAPTERS 00:00 - Meet Jason Tanaka and the AI-First Conversation 04:04 - The "Cocoon": Reinventing Software Development With AI 13:54 - What Does It Really Mean to Be AI-First? 21:39 - AI Governance, Risk and the Fear of the Unknown 26:36 - Will AI Replace Employees or Make Them More Powerful? 31:20 - Shadow AI and the New Role of IT 48:34 - Experimentation, Failure and Psychological Safety 01:05:07 - Growth Mindset and the First-Year Chef If you're a CEO, CIO, CTO, technology leader, developer, entrepreneur, or business executive trying to understand how AI will reshape organizations, this conversation offers a practical and thought-provoking look at what comes next.

  5. 3 Aug

    What A CEO Learned After Hitting $100M in Revenue! | David Karandish | Capacity

    David Karandish, founder and CEO of Capacity, returns to Ten Thousand Miles to unpack how his company rocketed from $5M to over $100M in annual recurring revenue in just three and a half years. David breaks down the three (soon to be four) big bets that built Capacity: automating customer support with AI, raising capital outside the traditional VC path, and running a "compound startup" playbook — a strategy borrowed from Rippling's Parker Conrad — to build, partner, and acquire (19 acquisitions in 39 months) their way into an all-in-one customer experience platform. Vic and David dig into how founder-to-founder relationships and a reputation for closing deals fuel Capacity's M&A engine, how agentic coding unexpectedly solved the "impossible" problem of integrating 19 acquired companies, and why differentiated AI models — not one-size-fits-all LLMs — will define the next wave of AI economics. The conversation also covers AI's role in education, why "problem describing, selecting, and solving" should never be collapsed into one step, how Capacity thinks about competition when everyone claims to be an AI company, and what inning we're really in when it comes to enterprise AI adoption. Chapters 00:00 – Welcome Back: David Karandish Returns 01:16 – From $5M to $100M ARR: The Three Big Bets 05:05 – The Compound Startup Playbook (Parker Conrad's Framework) 12:23 – How Capacity Finds, Diligences, and Closes Acquisitions 20:15 – Agentic Coding: The Hidden Unlock for M&A Integration 25:42 – Token Costs, Model Economics, and the Future of Compute 42:20 – AI in Education, Work, and the "Agents Everywhere" Bet 52:33 – Competing on the Oval: Problem-Solving Framework and What's Next Guest: David Karandish, Founder & CEO of Capacity, previously founder of Answers.com

  6. 27 Jul

    Scaling Through Recessions, AI, and Everything Else That Goes Wrong

    CEO Interview - What does it really take to grow a company from $6 million to more than $100 million in revenue? Leadership... In this episode of Ten Thousand Miles, Vic Pepe sits down with Josh Gould - CEO of The Big Word, investor, and entrepreneur who has spent decades building and scaling businesses through recessions, wars, AI disruption, and private equity ownership. Josh shares the unfiltered realities of entrepreneurship: why failure is the norm, how resilience beats brilliance, and why the companies that survive aren't always the prettiest—they're the ones built like cockroaches. The conversation dives into scaling, private equity, AI, leadership, difficult decisions, and the mindset required to build businesses that can withstand almost anything. Along the way, Josh offers practical lessons on hiring, innovation, and why having fun may be one of the most underrated business strategies of all. Whether you're a founder, executive, investor, or aspiring entrepreneur, this episode is packed with hard-earned wisdom from someone who's lived every lesson he shares. In this episode: - Growing a company from $6M to $100M+ - Why most entrepreneurial decisions fail—and why that's okay - The "cockroach" philosophy for building resilient businesses - Lessons from surviving multiple waves of AI disruption - What it's really like selling to private equity - Build vs. buy: making smarter technology decisions - Hiring leaders who complement your weaknesses - Why entrepreneurship is both freedom and sacrifice - The overlooked importance of having fun while building something meaningful Chapters 00:00 Welcome to Episode 120 & Meet Josh Gould 03:26 The Mission That Has Driven Josh's Entire Career 09:42 Why Failure Is the Real Path to Entrepreneurial Success 19:14 Scaling from $6M to $100M Through Constant Reinvention 29:39 Selling to Private Equity: What Every Founder Should Know 47:00 AI, Automation, and the Future of Business 01:12:31 Lightning Round: Leadership Lessons, Hiring, and Why You Should Never Forget to Have Fun https://www.linkedin.com/in/joshuadgould?utm_source=share_via&utm_content=profile&utm_medium=member_ios https://youtube.com/@exec_craft?si=pZ-kiXjXXgsFn69r https://www.instagram.com/execcraft?igsh=YzNtbGR5bmg5OHNo https://en-us.thebigword.com/

  7. 20 Jul

    This Is What Reinvention Really Looks Like! | Lori "ICE" Fetrick

    See how a former Gladiators star handles public criticism. Learn how she pivots from being mocked to turning that attention into profit.In this candid Gladiators interview, we sit down to discuss the reality of life after the show. Many public figures face ridicule online, but this conversation explores a different approach: embracing the attention rather than fighting it. If you have ever wondered how to shift your mindset when people are laughing at you, this discussion offers a practical perspective on taking control of your own narrative.We cover the challenges of public perception and the specific moment of clarity that led to this change in strategy. By dealing with criticism head-on, the guest explains why choosing to monetize the memes was the smartest business decision they could make. This is a must-watch for anyone interested in personal branding and the realities of modern media fame. Subscribe for weekly media and entertainment breakdowns, and tell us in the comments if you would do the same in their position. 00:00 Meet Lori “ICE” Fetrick: The Queen of Reinvention 03:17 From San Bernardino Athlete to Bodybuilder 13:32 Auditioning for American Gladiators 23:40 Fame, Madison Square Garden, and Life Behind the Scenes 26:31 Muscles & Mayhem and What Happened After Gladiators 34:10 The Hustle Years, Failure, Fear, and Reinvention 47:02 Staying Relevant and Unapologetically Yourself at 63 53:13 OnlyFans, Fitness, Longevity, and What Comes Next https://lorifetrick.com/ https://www.instagram.com/lori.ice.fetrick/ https://www.facebook.com/Lori.Fetrick.Ice/ https://x.com/LoriIceFetrick https://www.youtube.com/@UC8JWfhbLQ_2MCMAUBeHqaQA https://onlyfans.com/Lorifetrick

  8. 13 Jul

    Strength, Discipline, Legacy! | Josh Holyfield

    Josh Holyfield discusses the realities of building a legacy and the discipline required to sustain it. Get a raw look at his personal story and the specific mindset shifts needed for long-term growth. This session explores the journey behind the Josh Holyfield brand, moving past standard interview surface-level questions. We examine the foundational experiences that prepared him for his current trajectory and analyze the practical steps he takes to maintain daily consistency. This is for listeners who want to understand the rigorous work ethic that drives high-level performance. By examining his personal philosophy, you will gain a clearer picture of how to handle professional friction. We break down the specific mental hurdles Josh Holyfield faced and how his approach to obstacles has evolved over time. If you are looking for actionable insights on discipline, this conversation provides a blueprint for applying those lessons to your own path. Chapters 00:00 – Meet Josh Holyfield: Reinvention Through Service 06:00 – From Homelessness to the U.S. Military 13:00 – Iraq, Afghanistan, and Finding Purpose Under Pressure 20:00 – Obedience vs. Discipline: The Lesson That Changed Everything 28:00 – Heartbreak, Identity, and Reinventing Himself 36:00 – Building a $15 Million Business by Serving First 46:00 – The Truth About Health, Hormones, and Lasting Transformation 56:00 – Life Lessons, Legacy, and Becoming the Man You Were Meant to Be

See All (135)

About

The road to success is full of hard work and determination. It is never easy - you just learn to handle hard... Here, I interview people who "make it look easy" but leave it all on the field daily to do so.

Information

  • Creator
    Vic Pepe
  • Years Active
    2024 - 2026
  • Episodes
    135
  • Rating
    Explicit
  • Copyright
    © Copyright 2025 Ten Thousand Miles
  • Show Website
    Ten Thousand Miles

You Might Also Like