Are you a high-performing executive who wants to earn freedom while keeping your professional edge?
Then the Going Long Podcast with Billy Keels is for you.
This podcast shares the actionable insights you want to make more money, build more freedom, and
maintain the career you've built.
Whether you're building a business on the side, investing your capital, or identifying your passion project, you'll get real stories and tactical strategies from others who've done the same on their terms.
Hosted by international advisor and founder of The Executive Edge Advisory™️ Program, Billy Keels, this is your blueprint for creating income optionality, growing with intention, and protecting the professional momentum you've earned.
With over 550 episodes and more than five years of insights, this show delivers a mix of solo episodes and expert guest interviews.
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Leveraging Corporate Communication Habits to Build Global Career Options - Derek Smith
Season 1 · Episode 661
Wednesday, September 2, 2026 • Duration 37:58
Are you an overachieving director, VP, or enterprise leader who wants to take the high-level communication habits you mastered in the corporate world and turn them into a sovereign, global career?
In this transparent guest conversation, host Billy Keels sits down with Derek Smith—a public speaking coach and veteran MC of over 5,000 events who used his corporate foundation to engineer an international lifestyle spanning 54 houses across three continents. Derek reveals how winning Samsung's content creator competition at the 2010 Winter Olympics served as a turning point, why over 70% of communication is non-verbal when navigating global boundaries, and how asking one life-changing question shifted his entire trajectory. Discover how to leverage corporate team dynamics, overcome the fear of starting late, focus on "Who, Not How," and build a business in your personal zone of genius entirely on your own terms.
05:39 - The Critical Corporate Lesson: Leveraging Team Dynamics in Business
09:35 - Embracing the Nomadic Lifestyle: 54 Houses and Three Continents
16:05 - Unlocking Global Opportunities Through Non-Verbal Communication
22:41 - What It Actually Means to Be an MC and Hold a Room's Energy
28:39 - The Life-Changing Question That Shifted Derek's Career Overnight
33:27 - Overcoming the Fear of Starting Late & Finding Your Zone of Genius
37:22 - Schedule Sovereignty: Applying "Who Not How" to Own Your Time
📘 About Billy Keels & Corporate Optionality
If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.
With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.
This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!
Finding the Right Side Business Model for Your Corporate Skill Set
Season 1 · Episode 660
Tuesday, September 1, 2026 • Duration 13:39
Are you an overachieving director, VP, or senior AE burning the candle at both ends because you're forcing a cookie-cutter side business that doesn't fit your background?
In this highly strategic solo episode, host Billy Keels breaks down why choosing the wrong side venture model leads to intense overwhelm, wasted energy, and a loss of your most critical asset—your time. Drawing from his 26-year corporate career managing $100M EMEA operations for a legacy German enterprise software titan, Billy shares how he built a side asset engine generating $212,000+ per year in additional revenue. Discover how to analyze your current resources using the high-level "invest or build" framework, calculate your exact optionality number down to the decimal place, and trade the limiting fear of failure for a powerful mindset shift: What if it actually works?
How can a senior corporate leader find the fastest side business model to generate quick wins?
What is the hidden relationship between your available capital, required control, and the business path you choose?
Why is knowing your career optionality number down to the exact decimal point critical to stopping the endless work loop?
How does answering the question "What if it does work?" shift an executive's transition confidence?
What does it feel like to spend the last 4 years of a corporate career completely independent of a company paycheck?
⏱️ Episode Chapters:
00:00 - Creating Professional Optionality Aligned with Your Values
01:10 - Reclaiming the Global Strategy: An Overview of 26 Years in Corporate
📘 About Billy Keels & Corporate Optionality
From Cartier to Spain: How This Luxury Executive Redesigned Her Life for Impact - Katrina Logie
Season 1 · Episode 659
Thursday, August 27, 2026 • Duration 31:40
Are you a high-performing senior director, marketer, or brand strategist operating at the pinnacle of international luxury or management consulting, yet feeling an unshakeable urge to redirect your elite corporate execution into your own independent assets?
In this transparent guest conversation, host Billy Keels sits down with Katrina Logie, an international community strategist, startup mentor, and the visionary founder of Be Athletes. Katrina breaks down her professional trajectory, navigating high-stakes marketing, retail, and operational divisions across legendary brands like Christie's Fine Art, Cartier, and Bain & Company. Discover how an international stint working the Olympic Games shattered her conditioning regarding "institutional security" and traditional career timelines. Learn how to navigate family skepticism when stepping off the standard corporate path, leverage your enterprise strategy reps to serve startup networks, and implement a calculated "athlete's mindset" to construct powerful professional choices entirely on your own terms.
How can an executive identify the precise season when institutional security starts to limit personal growth?
What does it look like to transfer top-tier consulting frameworks from firms like Bain & Company into independent ventures?
How do you handle internal and family-driven anxieties when stepping away from highly prestigious global brands?
Why is an iterative, testing-based approach superior to standard perfectionism when building an independent community?
How does integrating the habits, visualization models, and physical disciplines of an elite athlete prevent founder burnout?
⏱️ Episode Chapters: 📘 About Billy Keels & Corporate Optionality
Shifting from Career Success to Personal Legacy: A Lesson for High Achievers
Season 1 · Episode 658
Tuesday, August 25, 2026 • Duration 10:58
Are you a senior director, VP, or elite account executive completely nose-down in your career, chasing corporate accolades, status, and wealth while your family's attention slips away?
In this highly reflective solo episode, host Billy Keels breaks his own rules to make a mandatory recommendation: anyone managing a demanding multinational career needs to watch George Clooney's movie J. Kelly. Following the story of a massively successful, wealthy superstar actor at the tail end of his career, Billy highlights the painful, subtle realities of a high performer who achieved the absolute pinnacle of external validation, only to realize his deepest true desire was simply to capture the attention of his daughters—before realizing he had spent decades being "on" for the wrong people. Learn how to find true harmony over balance, escape the corporate machine's lease option on your life, and intentionally protect the relationships that actually belong to you before time runs out.
Why should George Clooney's movie J. Kelly be considered required viewing for senior corporate leaders?
What is the hidden relationship cost when a high-performing executive focuses entirely on personal status and accolades?
What is the difference between chasing an impossible "work-life balance" versus creating true professional harmony?
How does the corporate machine trick high earners into trading away irreplaceable time with their children?
Why do physical corporate assets go back to the machine while personal relationships remain your only true asset?
⏱️ Episode Chapters: 📘 About Billy Keels & Corporate Optionality
The Subway Wake-Up Call: Engineering Your Career's Next Chapter - Rupinder Mangat
Season 1 · Episode 657
Thursday, August 20, 2026 • Duration 39:00
Are you an overachieving director, VP, or enterprise tech leader who has spent decades climbing the corporate ladder, yet feels an unshakeable urge to stop postponing the personal legacy projects that matter most?
In this transparent guest conversation, host Billy Keels sits down with Rupinder Mangat—a veteran technology executive with over 30 years leading enterprise sales, business strategy, and global initiatives at industry titans like Gartner, IBM, and Microsoft. Rupinder shares her remarkable trajectory as a British expat transitioning into corporate America, revealing the exact moment a near-miss subway injury forced her to stop doubting her value, sign her voluntary retirement agreement, and embrace true schedule sovereignty. Discover how to transfer top-tier corporate assets like "influencing without authority" into independent assets, overcome the emotional friction of surrendering your company badge, and build a vibrant second-act venture that serves underserved professional communities entirely on your own terms.
How does a 30-year tech executive handle the emotional transition of stepping away from Microsoft?
What are the subtle, critical cultural differences between executing corporate strategy in the UK versus corporate America?
How do you successfully transfer enterprise skills like "influencing without authority" into independent entrepreneurship?
Why is separating your individual identity from your corporate company badge essential for long-term career optionality?
How can women executives over 50 overcome self-doubt to launch high-impact independent assets?
⏱️ Episode Chapters: How to connect with Rupinder: LinkedIn: Event and Tickets: 📘 About Billy Keels & Corporate Optionality
Shifting Your Priorities: Why Your Title Can't Buy True Family Time
Season 1 · Episode 656
Tuesday, August 18, 2026 • Duration 11:49
Are you a senior executive or elite tech leader spending all your working hours riding a corporate treadmill, sacrificing deep presence with aging parents or growing children just to secure the next title?
In this transparent and deeply reflective solo episode, host Billy Keels breaks down a powerful life lesson on how life experiences fundamentally reshape a high performer's priorities. Billy recounts his recent 3,925-mile transatlantic investment—flying from Barcelona to the United States for a brief five-day trip purely to celebrate his mother's birthday and watch basketball on the couch with his father. Drawing contrast against his 26-year corporate history managing $100M EMEA operations for a blue-logo German enterprise software giant, Billy breaks down what it truly feels like to exit corporate dependency. Learn how to achieve a lifestyle where you no longer need to beg a boss for personal time off (PTO), how to transition your relationship with your 168 weekly hours, and how to build a predictable pathway to optionality that lets you be fully present for the moments that matter most.
How do an executive's personal priorities radically shift as their parents and children grow older?
What does true time control feel like compared to chasing corporate titles and enterprise perks?
How can a high achiever build a sustainable professional model without needing to request PTO?
What is the reality of battling severe jet lag as a mature professional compared to traveling early in your career?
How do you realign your weekly 168 hours to focus on personal impact and deep presence with loved ones?
⏱️ Episode Chapters:
📘 About Billy Keels & Corporate Optionality
The Resilient Executive: Turning Life's Toughest Reset Points into Career Options - Diwas Timsina
Season 1 · Episode 655
Thursday, August 13, 2026 • Duration 46:08
Are you a senior tech leader, architect, or enterprise sales executive sitting on high-value technical acumen, wondering how to channel your skills into an independent venture without sacrificing your corporate career?
In this transparent guest conversation, host Billy Keels sits down with Diwas Timsina, a Customer Success Architect at a market leading enterprise software and services company, founder and CTO of Sarva, and former TEDx speaker. Born in a refugee camp in eastern Nepal, Diwas details his journey of arriving in the U.S. at age 14, changing high schools three times, and ultimately earning his MBA while navigating corporate consulting and enterprise software. Discover how Diwas uses the methodology of "building quietly" to prove concepts to himself before sharing them publicly, how he translates C-suite enterprise client conversations into grassroots multilingual AI tools for small vendors, and how to maintain total perspective during career challenges by remembering your ultimate starting point.
How can an enterprise tech professional quietly build a side business without disrupting their main career track?
What does it look like to transition from a refugee camp background into C-suite enterprise consulting?
How do you leverage high-level corporate architecture reps to solve real-world problems for small businesses?
Why is "building quietly and proving it to yourself first" the ultimate strategy for high performers?
How do you maintain mental resilience and perspective when facing high-stress corporate or business obstacles?
⏱️ Episode Chapters: Contact Diwas: LinkedIn: 📘 About Billy Keels & Corporate Optionality
The Corporate Line Item Trap: Why Executives Are Afraid to Invest in Themselves
Season 1 · Episode 654
Tuesday, August 11, 2026 • Duration 14:48
Are you a senior corporate leader or high-performing director relying on your company's learning and development budget to dictate your personal growth and future security?
In this empowering solo episode, host Billy Keels reacts to a powerful life lesson from fellow podcaster Chris Williamson: no one is coming to save you. Billy pulls back the curtain on why market-leading multinationals constantly put their money where their mouth is—investing massive financial resources into technical skills, soft skills, and elite methodologies like MEDDIC or Challenger Sales to fuel their corporate organism. Discover why you must break the habit of putting yourself last, treat your personal transition as your own business line item, and aggressively invest your own time, effort, and capital into guided frameworks that unlock a predictable pathway to optionality while you continue to excel at your 9-to-5.
What does Chris Williamson's phrase "no one is coming to save you" mean for corporate leaders?
Why do large multinational corporations invest so heavily in training their frontline executives?
How do you shift your mindset from a corporate line item to creating your own personal L&D budget?
What is the true opportunity cost of trying to launch a side business completely alone?
How can making a significant personal financial investment dramatically accelerate your business decisions?
⏱️ Episode Chapters:
00:00 - Solo Strategy: Moving Beyond General Corporate Concepts
📘 About Billy Keels & Corporate Optionality
What Does Optionality Mean If You Don't Want to Quit Your Corporate Job? - Chad Greenlee
Season 1 · Episode 653
Thursday, August 6, 2026 • Duration 41:28
Are you a senior executive or elite corporate leader who thinks achieving true career optionality means you are forced to quit the corporate game you actually enjoy?
In this highly unique guest conversation, host Billy Keels sits down with Chad Greenlee, a partner at Creative Planning and one of the very first members to go through what is known today as the Executive Edge Advisory Program. Chad pulls back the curtain on why typical "popular opinions" regarding financial independence are flawed, sharing how a midnight flight unlock forced him to ditch cookie-cutter definitions of work-life balance and build a customized "ideal day" model. Discover how Chad utilized ghostwriting, marketing, and copywriting skills honed in his side venture to build a multi-million dollar intern pipeline for his employer, land a massive promotion to Vice President of Sales after seven previous rejections, and confidently master his career on his own timeline.
What does career optionality actually look like for a senior leader who chooses not to quit their corporate job?
How can an executive handle the emotional transition of scaling back a side business to go "all in" on a major corporate acquisition?
Why is the foundational equation "Am I valuable and am I available?" the ultimate key to permanent employability[cite: 3, 5]?
How can a senior professional bounce back after being turned down seven times for leadership positions to secure a VP of Sales role[cite: 3, 5]?
What are the benefits of having an outside mentor regurgitate your words back to you to identify what tasks to stop doing?
⏱️ Episode Chapters: Contact Chad Greenlee: Website: 📘 About Billy Keels & Corporate Optionality
Every Corporate Relationship Ends: Lessons from Pep Guardiola
Season 1 · Episode 652
Tuesday, August 4, 2026 • Duration 14:12
Even the greatest leaders in the world eventually hit the end of the road. Pep Guardiola, for the decade that he was at Manchester City, won 20 titles. But when it was time for him to walk away, it was the inner voice inside of him that told him it was that his time was up. This episode reveals exactly why every corporate relationship ends and what you can do to make sure that you don't have complacency destroy your edge.
Going Long Podcast Episode 652: Every Corporate Relationship Ends: Lessons from Pep Guardiola
( To see the Video Version of today's conversation just CLICK HERE. )
In today's episode of The Going Long Podcast, you'll learn the following:
[00:24 - 00:53] Billy welcomes us to and introduces today's show.
[00:53 - 09:31] Billy discusses the inevitability of corporate relationships ending, using Pep Guardiola's career as an example. emphasizing the importance of recognizing when it's time to move on and preparing for transitions.
[13:10 - 14:11] Billy wraps up the show.
If you're a corporate executive who wants to make your role optional, then grab your FREE ebook with Billy's proven 3 step process at: www.makeitoptional.com
What you can expect to get out of this ebook:
Learn how to achieve corporate optionality
Gain true control over your career
Turn corporate skills into personal assets
With 26 years of experience in corporate sales leadership, achieved optionality through multiple income streams, Billy has helped dozens of executives build their paths to take control of their time.
02:30 - The Illusion of the President's Club and the Reality of Paycheck Dependency
03:40 - Burning the Candle at Both Ends: Reaching a Year-and-a-Half Breakthrough
04:55 - 5 Years Outside the Enterprise: Why the Corporate Game Stays the Same
05:40 - The Strategic Fork in the Road: Evaluating the Invest vs. Build Model
06:35 - Tracking Your Escape Route: Why You Need an Exact Decimal Number
07:50 - Navigating Unfamiliar Spaces and Embracing the Discomfort of the Unknown
08:35 - Shifting the Focus: Olivier Jadoul and asking "What If It Does Work?"
09:50 - The 41 Streams of Income Engine: Managing 400+ LP Units
11:00 - Walking into Boardrooms by Choice: Shifting From Theory to Skill Mastery
If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.
With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.
This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!
00:00 - Recording Track Intro: Redesigning a Luxury Corporate Path for Deep Personal Impact
01:10 - The Generation Trajectory: Unpacking Traditional Career Expectations vs. Creative Curiosity
01:54 - Christie's Fine Art & Cartier: Gaining Elite Institutional Experience in London
02:30 - The Olympic Catalyst: How Living in Sydney and London Disrupted Corporate Conditioning
03:00 - Bain & Company: Shifting from the Outside In to Master Organizational Strategy
03:45 - The Startup Jump: Moving Beyond Multi-Layered Corporate Hierarchies
05:00 - The Sovereignty Shift: Moving to Spain and Launching as an Independent Consultant
05:40 - Overcoming the Safety Narrative: Navigating Parental Concerns Regarding Career Risk
06:35 - The Who Factor: Why Your Core Professional Network Dictates Your Long-Term Value
07:50 - Defeating Academic Perfectionism: Embracing an Iterative Solution-Finding Process
08:35 - The Genesis of Be Athletes: Injecting Rigor and Good Habits into Founder Networks
10:15 - Breaking Stagnation: Using Movement and Sport to Shift Mindsets and Get Out of Your Head
11:00 - 6-to-12 Week Sprints: Launching High-Impact Programs for Teams and Leaders
12:15 - Reclaiming Your Freedom and Connecting with Katrina Logie
If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.
With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.
This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!
00:00 - Breaking the Rules: A Mandatory Movie Recommendation for Senior Leaders
01:10 - Sunday Reflection: Unwinding on the Couch to Analyze J. Kelly
02:15 - The Superstar Trap: Accolades, Wealth, and High-Performance DNA
03:30 - The Tail End of a Career: What Matters Most to a 60-Year-Old Achiever
04:30 - The Subtle Truth: Realizing You Are Constantly Alone Inside the Machine
05:15 - The European Travel Trap: When Your Family Rejects Your Time
06:05 - Who is Standing Beside You in the End? Agents vs. Family
07:00 - The Lease Option: Why Corporate Fame and Luxury Cars All Go Back
08:15 - Reclaiming Harmony: Intentionally Investing in Those Looking for Your Attention
09:30 - Reclaiming Your 168: Moving from Success Theory to Personal Practice
If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.
With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.
This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!
If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.
With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.
This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!
00:00 - Tipping Point: How Life Experiences Rewire Your True Priorities
01:10 - Investing 3,925 Miles Across the Atlantic for a Birthday Celebration
02:15 - Reflecting on 26 Years of Corporate Enterprise Software Accolades
03:30 - The Reality Shift: Aging Parents, Growing Kids, and Long-Distance Realities
04:30 - Reclaiming Time Autonomy After Shifting Through Personal Change
05:40 - The Power of Independence: Traveling Stateside Without Asking a Boss
06:35 - Couch Time with Dad and Car Time with Mom: Reclaiming Precious Moments
08:15 - Mother Time Catches Up: Navigating Jet Lag in an Over-40 Transition
09:30 - Escaping the Corporate Treadmill of Constant Growth and Always-On Stress
11:00 - Moving From Time Management Theory to Radical Personal Practice
If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.
With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.
This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!
If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.
With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.
This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!
01:10 - Reacting to Chris Williamson: Life Lessons in 60 Seconds
02:00 - The Loud Inner Voice: Shifting from Promotable to Optional
02:45 - The High Cost of Going It Alone on Your Side Business
03:40 - Why Market Leaders Put Their Money Where Their Mouth Is
04:55 - MEDDIC, Spin, and Challenger: Analyzing Corporate L&D Investments
06:15 - Becoming the Market Leader of Your Own Personal Optionality
07:10 - Breaking the Habit of Putting Your Own Growth Last
08:35 - Billy's First Six-Figure Investment in a Personal Coach
09:50 - Maximizing the 168: Using Guided Action to Hit Your North Star
11:00 - Reclaiming Your Worth: Shifting From Theory into Practice
If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.
With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.
This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!
If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.
With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.
This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!
This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and start living your IDEAL day - today!
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