War Room Wisdom: Battle-Tested Marketing for Founders with Lee Pepper
The Relentless Pursuit of Winning Podcast
Release Date: 09/09/2025
The Relentless Pursuit of Winning Podcast
đ„ Excerpt âEither I will win, I will learn, or I will transform.â ⥠TL;DR Frances Strickland joins me to explore value, pricing, clarity, and faith in business. She outlines how structure, leadership, and flow reveal the hidden leaks that keep founders from predictable profitability. We talk about defining an ideal customer, practicing value based pricing, and selling in a way that honors both the buyer and the work. Frances shares stories about financial pressure, reinvention during COVID, and spiritual nudges that shaped her offers and networking strategy. At its core, this...
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đ„ Excerpt âPeople change when the pain of remaining the same is greater than the pain of the change itself.â ⥠TL;DR John Gallagher left a secure corporate role at IBM to build a purpose-driven coaching practice rooted in faith, intentionality, and transformation. In this episode, we unpack his journey from executive leadership to entrepreneurship â exploring how feedback, surrender, and alignment with purpose shaped his lifeâs work. John and Rick discuss leading with integrity, building Kingdom impact through business, and finding harmony between faith, work, and personal growth....
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đ„ Excerpt When you give yourself the space to fully process and be present with all of it, every breakdown has the potential for a breakthrough.â ⥠TL;DR Dr. Camille Prestonâbusiness psychologist, author of Living Real, and founder of AIM Leadershipâjoins Rick Meekins to unpack what it means to lead and live authentically in the midst of compounded crises. From grief and burnout to self-love and leadership, Camille challenges the illusion of success and explores how embracing intensity, presence, and vulnerability can transform both leaders and organizations. đ Show Notes We live...
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đ„ Excerpt âReferrals arenât the icing on the cakeâin a lot of businesses, they are the cake.â ⥠TL;DR Bill Catesâbest-selling author, keynote speaker, and the renowned âreferral coachââjoins Rick Meekins to dissect the intersection of money, mindset, and business growth. From challenging the scarcity myth to reframing referrals as the foundation of sustainable revenue, this episode explores how founders can build wealth, relevance, and credibility through generosity and strategic relationship-building. đ Show Notes Iâve met plenty of founders who treat referrals as...
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đ„ Excerpt âAnything can be fixed financially. Anything. Sometimes itâs just within the companyâmaking small tweaks to how youâre charging, what youâre not charging for, where your moneyâs goingâand then laying it out so you have a plan.â â Lillia Sanders ⥠TL;DR Fractional CFO Lillia Sanders joins me to talk about rebuilding from the ground upâpersonally and financiallyâand what every founder needs to know to protect profits, make data-driven pricing decisions, and stop running blind. We dig into the discipline behind clean books, the courage to raise rates, the...
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đ„ Excerpt âYou have to assume the visionâbut donât take those assumptions as facts. Test them. Thatâs where you learn to fail fast.â ⥠TL;DR Author and product builder Kingsley Maunder joins me to dismantle the romance of âbig ideasâ and replace it with a system founders can actually use: start with the problem, define success and failure lines, ship the smallest thing that solves the biggest pain, and iterate on evidenceânot ego. We unpack bleeding-edge vs. table-stakes features, why messaging misses are data (not drama), and how to prioritize a roadmap with impact,...
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đ„ Excerpt What if the way you speakâor the identity you cling toâisnât the problem? Speech therapist and coach James Burden unpacks stuttering, ego, and the surprising power of letting go to actually win. ⥠TL;DR James Burdenâspeech therapist and founder of Stuttering Blueprintâjoins me to challenge the myths around stuttering, reframe it through a neurodivergence lens, and trace how a season of personal upheaval (divorce, burnout, a brain tumor) led him to a different definition of success: inner peace. We dig into radical self-acceptance, âwhite-knuckle fluency,â...
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đ„ Excerpt âIf I donât trust you, I wonât buy from you.â We go straight at the hard stuff: building trust at scale, using AI without losing the plot, and what happens when life redlinesâand then resets your purpose. ⥠TL;DR Sales enablement pioneer and keynote speaker Roderick Jefferson joins me to break down go-to-market enablement, why trust and empathy still close deals, and how to use AI as a productivity force multiplierâwithout outsourcing your judgment. We also get personal: his near-death stroke, the wake-up call that reordered his priorities from workâlife to...
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đ„ Excerpt âYou can chase adrenaline or you can build a life that matters. One keeps you entertained. The other keeps you proud.â đ Show Notes I donât often meet someone who literally ran toward war just to see what he was made of. John Graham didâand then spent the next few decades turning that raw hunger for danger into disciplined service and leadership. In this conversation, we trace his arc from Algerian border crossings and frontline diplomacy in Vietnam to a mid-storm bargain with God in the Gulf of Alaska, and ultimately to a life committed to peace, justice, and building...
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đ„ Excerpt âYouâre never going to feel confident enough until you just do it. Act firstâthe confidence follows.â ⥠TL;DR RN-turned-founder Lauren Bensakovich joins me to break down how she built a boutique healthcare recruiting firm on an abundance mindset, disciplined outreach, and zero-nonsense personalization. We get into masterminds, automation (used intelligently), coaching candidates with integrity, and how AI helpsâbut doesnât replaceâhigh-stakes recruiting đ Show Notes Abundance isnât a hashtag. Itâs a way of operating. In this episode, I sit down with Lauren...
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âIf youâre still âtrying tacticsâ and calling it strategy, youâre losing ground. In this episode, we translate force multiplication, the anvil-and-hammer, and commanderâs intent into a practical marketing playbook you can deploy by Monday.â
⥠TL;DR
Army veteran and former CIO/CMO Lee Pepper joins Rick Meekins to unpack how battlefield strategies translate directly into business growth. From repurposing content like force multiplication to wargaming competitor moves, this episode delivers a disciplined, no-fluff blueprint for marketing that actually drives revenue.
đ Show Notes
Most leaders donât have a marketing problemâthey have a strategy problem disguised as âchannel hopping.â In this conversation, I sit down with Lee PepperâArmy veteran, behavioral health executive, and author of Never Outmatchedâto break down military tactics that work just as well in the boardroom as they do in the field.
We cover how force multiplication turns one piece of content into a multi-platform machine, why commanderâs intent is the antidote to micromanagement, and how the anvil-and-hammer strategy keeps you from cutting the very investments that drive conversion. Lee also shares the importance of wargaming, the danger of buying tools without training, and why pivot speed is the moat that keeps you alive in shifting markets.
If youâre tired of vanity metrics and tactic-chasing, this episode arms you with tested frameworks that align teams, protect budgets, and create scalable wins.
â Key Takeaways
- Force multiplication: repurpose one core asset into many channels, multiplying reach without multiplying cost.
- Commanderâs intent: set the mission, constraints, and goalsâthen let your team execute. Micromanagement is attrition.
- Anvil-and-hammer: donât cut the âexpensiveâ holding force that enables your real conversion strike.
- Tie marketing to business KPIs: focus on calls, demos, revenueânot likes or impressions.
- War-game quarterly: model competitor plays and pre-plan your counters.
- Operational readiness: tools fail without training, support, and ownership.
- Pivot by day 30â45: own the miss, redeploy, and move. Speed of learning wins.
- Partner across the enterprise: marketing should solve Finance and HR problems too.
đ€ Bio
Lee Pepper is an Army veteran turned enterprise operator who served as CIO and CMO across behavioral health companies before writing Never Outmatched. His work translates battlefield strategyâforce multiplication, commanderâs intent, anvil-and-hammerâinto modern marketing systems that drive revenue. He volunteers with the Veterans Treatment Court in Nashville and speaks nationally on leadership, go-to-market, and organizational readiness.
đ§ Chapters
00:00 Introduction to Military Marketing Strategies
01:03 Lee Pepperâs Background and Transition to Marketing
03:26 Force Multiplication in Marketing
06:09 Setting Commanderâs Intent for Business Success
09:25 Tying KPIs to Business Outcomes
10:35 The Anvil and Hammer Strategy
15:55 The Importance of Competitive Intelligence and War Gaming
17:36 Operational Readiness in Business
19:40 Evaluating New Technologies
20:44 Leadership and Team Dynamics
22:05 Learning from Historical Figures
23:43 The Importance of Pivoting
26:20 Staying Ahead of Competitors
27:45 Cognitive Biases in Marketing
29:34 Building Strategic Alliances
31:12 Fostering Company Culture
33:21 The Journey of Writing a Book
36:59 New Chapter / Close