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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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- 1 weeks ago1h 21m
Master Your Emotions, Master Your Life!
Learn to master your emotions to change the trajectory of your life. The subconscious mind drives 95% of your daily actions. Most people operate on autopilot, unaware that their internal programming dictates their external results. In this conversation, we break down why your subconscious mind is the actual engine behind your habits and how you can begin to audit that programming to shape your reality more intentionally. Understanding these mechanisms is the first step toward true personal growth. When you stop reacting to the world and start managing the beliefs that drive your behavior, you regain control over your outcomes. We discuss practical ways to bridge the gap between what you want and what you actually do. Subscribe for weekly success mindset breakdowns, and let me know in the comments: what is one habit you are currently working to change? CHAPTERS 00:00 Intro 01:45 What Is Emotional Mastery? 11:26 Constance’s Journey 18:29 When Persistence Becomes Denial 22:33 When Career Becomes Your Identity 30:47 Emotional Mastery for Leaders 47:25 The Patterns Holding You Back 01:06:12 The Success Trap
- 1 weeks ago29 min
You May Be Closer Than You Think
You might be on the one-yard line and not even know it. Why quit now when you are closer than you think? We often measure our progress by external milestones, but real growth is usually invisible until it hits the tipping point. If you feel like your effort isn't paying off, you might just be dealing with the gap between action and results. This is where most people abandon their goals, failing to see that their persistence is actually compounding beneath the surface. Only 32% of our community is currently subscribed, which means many of you are missing the specific tools needed to maintain a high-level success mindset. Whether you are building a business or chasing a personal milestone, stop judging your journey by lagging indicators. Start trusting the process that happens before the breakthrough. Subscribe for weekly success mindset breakdowns, and let me know in the comments: what is the one milestone you are currently pushing toward? CHAPTERS 00:00 - Please Subscribe 00:30 - What If You’re Closer Than You Think? 02:20 - Why the Scoreboard Can Lie 09:54 - Hindsight Makes Success Look Inevitable 12:59 - The One-Yard-Line Problem 16:57 - Persistence vs. Stubbornness 20:00 - 3 Questions to Ask Before You Quit 26:25 - The Invisible Compound Effect
- 2 weeks ago23 min
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
- 3 weeks ago1h 9m
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.
- Aug 18, 202625 min
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
- Aug 11, 20261h 12m
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.
- Aug 3, 202650 min
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
- Jul 27, 20261h 8m
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/
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About Ten Thousand Miles
I interview people who "make it look easy" but leave it all on the field daily to do so.
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