Marketing Notes for Entrepreneurs by Grey Leaf Media

Jason Haeger
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Marketing Notes for Entrepreneurs by Grey Leaf Media is for marketers, founders, and leaders of impact-driven businesses. We look at common problems, unexpected solutions, and strategies to help grow your impact. Growth is more than profits, it is measured in tangible positive impact. Without growth, your impact stalls. Featuring: The Trust Wall series! A unique look at how to think about progress, mistakes, consistency, and growth. Episodes 2-8 This podcast is brought to you by Grey Leaf Media. Marketing consulting, strategy, and marketing technology solutions for business that matters.

Episodes

  1. Episode 12: How a Wrong ICP Breaks Your Positioning: Why Your Actual Customers Don't Recognize Themselves

    6D AGO

    Episode 12: How a Wrong ICP Breaks Your Positioning: Why Your Actual Customers Don't Recognize Themselves

    When your actual customers land on your website, do they immediately think "this is exactly what I need"? Or do they have to work to figure out what you do? Most founders assume confusion is a filter. If someone doesn't understand the positioning, they're not the right customer. But confusion isn't a filter. It's a signal. When your ICP is wrong, your actual customers encounter your positioning and don't recognize themselves. The people funding your business have to squint to see themselves in it. In this episode, we break down what positioning actually is, the three ways a wrong ICP destroys it, how to diagnose whether your positioning is speaking to who's actually buying, and how to rebuild it around the people who actually buy from you. We also tie this back to the Trust Walls series: positioning is where your foundation meets the market. When the foundation is built on the wrong assumption, the positioning will always feel slightly off. Not broken enough to ignore. Not clear enough to convert. Key Topics What positioning actually is: the answer to one question in your customer's mind, "Is this for me?" Why confusion isn't a filter, it's a signal that your positioning isn't speaking to who's actually buying The three ways a wrong ICP breaks positioning: wrong problem, wrong vocabulary, wrong differentiation The Segway story: positioned for urban commuters, actual buyers were mall security, tourism companies, and warehouse operators The BlackBerry lesson: kept speaking to IT departments after the purchase decision shifted to individual employees The JCPenney mistake: differentiated on pricing honesty for sophisticated shoppers while actual customers were deal-hunters who valued the coupon ritual Four diagnostics: the recognition test, the vocabulary gap, the differentiation relevance check, and the is this for me test Four steps to fix it: rewrite around your actual customer's problem, adopt their vocabulary, lead with what drives decisions, test before publishing The connection to the Trust Walls series: positioning built on a false foundation will always feel slightly off Resources Brand Therapy Diagnostic: https://greyleafmedia.com/diagnostic/ WordPress Design, Development, and Hosting: https://greyleafmedia.com/services/ More Episodes: https://greyleafmedia.com/podcast/ Connect on LinkedIn: Jason Haeger

    23 min
  2. Episode 11: How a Wrong ICP Breaks Your Content Strategy: Why Your Content Performs but Doesn't Convert

    APR 24

    Episode 11: How a Wrong ICP Breaks Your Content Strategy: Why Your Content Performs but Doesn't Convert

    Your content is getting engagement. Comments, shares, positive feedback. But nobody is buying. That is not a content quality problem. That is a content direction problem. You are creating content for the wrong people. And right now, the tools available to create content have made it faster and easier than ever to build the wrong audience at scale. Speed without direction is not efficiency. It is just getting lost faster. In this episode, we break down the three ways a wrong ICP destroys your content strategy, why the engagement trap is more dangerous than it looks, how AI-generated content accelerates the problem when used without specific customer input, and how to rebuild your content around the people who actually buy from you. Key Topics The three ways a wrong ICP breaks content: wrong problems, wrong language, wrong format Quibi's two billion dollar wrong-ICP content mistake and what it teaches about solving for the wrong moment How New Coke reveals the difference between accurate content and content that speaks the right language The engagement trap: why positive content metrics can actively mislead you How AI-generated content defaults to the average and builds the wrong audience faster Four diagnostics to tell if your content strategy is broken by a wrong ICP Four steps to fix it: customer language first, map the actual journey, accept lower engagement, kill content that attracts the wrong people Resources Brand Therapy Diagnostic: https://greyleafmedia.com/diagnostic/ WordPress Design, Development, and Hosting: https://greyleafmedia.com/services/ Website: https://greyleafmedia.com Connect on LinkedIn: Jason Haeger

    23 min
  3. Episode 10: How a Wrong ICP Breaks Your Social Media: Why Your Engagement Doesn't Convert

    APR 17

    Episode 10: How a Wrong ICP Breaks Your Social Media: Why Your Engagement Doesn't Convert

    Your social media is getting engagement. Likes, comments, shares. But the people engaging are not buying. That is not a content problem. That is a foundation problem. When your ideal customer profile is wrong, your entire social media strategy breaks. You are posting on the wrong platforms. You are using the wrong messaging. You are measuring the wrong metrics. And you are building an audience that will never convert. In this episode, we break down the three ways a wrong ICP destroys your social media, how to diagnose whether you are posting to ghosts instead of buyers, and how to rebuild your strategy around the people who actually buy from you. Key Topics: The three ways a wrong ICP breaks your social media: wrong platforms, wrong messaging, wrong metrics Broadcast platforms vs. conversation platforms: Instagram and TikTok vs. Reddit, Threads, and Bluesky Why your engagement does not convert and what that means about your ICP How to diagnose if your social strategy is broken: follower to customer conversion, engagement analysis, content message alignment The four steps to fix it: go where your customers are, rewrite your messaging, audit your audience, change what you measure Why a smaller audience of buyers is far more valuable than a large audience of browsers The hard truth: you might need to start over on the right foundation Resources: 1. Free Social Media Audit: https://greyleafmedia.com/social-audit 2. Brand Therapy Diagnostic: https://greyleafmedia.com/diagnostic/ 3. Website: https://greyleafmedia.com 4. Connect: LinkedIn - Jason Haeger

    19 min
  4. Episode 9: Your ICP is a Lie: Why Most Marketing Strategies Are Built on False Assumptions

    APR 11

    Episode 9: Your ICP is a Lie: Why Most Marketing Strategies Are Built on False Assumptions

    Your marketing probably isn't working. Not because you're doing it wrong. Because you're doing it for the wrong people. Most businesses build their entire marketing strategy around an ideal customer profile based on assumptions, not reality. Based on who they want to serve, not who actually buys. And when your ICP is wrong, everything downstream breaks. In this episode, we break down why most ICPs are lies, how the gap between theoretical and actual customers kills businesses, and how to find who you actually serve instead of who you think you serve. This is the first episode in a new series exploring how a wrong ICP cascades through your entire marketing system. Key Topics:  Why most ICPs are created based on assumptions instead of who actually buys  How you end up with two customer bases: the theoretical one you market to and the actual one funding your business  The cascade effect: when your ICP is wrong, it breaks social media, content, positioning, messaging, product, and pricing  The gap between who you think you serve and who actually buys  How to find your actual ICP: analyze customers, interview your best ones, map the gap, build from reality  Three common niching problems: too broad, wrong direction, too early  Why discomfort about your actual ICP is information, not failure Resources: Brand Therapy: greyleafmedia.com/diagnostic Website: greyleafmedia.com Connect: LinkedIn - Jason Haeger

    14 min
  5. Episode 8: The Cost: What It Actually Takes to Build a Business That Lasts (Trust Walls pt 7)

    APR 3

    Episode 8: The Cost: What It Actually Takes to Build a Business That Lasts (Trust Walls pt 7)

    Everyone wants a business that works. A structure that stands. A brand that lasts. But not everyone is willing to pay what it actually costs to build one. This is not about money. This is about the full cost: patience, focus, consistency, sacrifice, and the willingness to keep building when the results are not visible yet. In this episode, we explore the three costs everyone underestimates when building a business, why people consistently miscalculate what it takes, and the hidden expense of trying to build cheap. We break down how to count the cost before you start and how to decide if you are willing to pay it. Key Topics: The three costs everyone underestimates: patience, focus, and consistency Why people quit (it is not because building is too hard, it is because it feels repetitive) The hidden cost of building cheap: you always pay twice Five questions to decide if you are willing to pay what it costs Why counting the cost is strategic, not discouraging The difference between resourceful and cheap Resources: Brand Therapy: greyleafmedia.com/diagnostic Website: greyleafmedia.com Connect: LinkedIn - Jason Haeger

    24 min
  6. Episode 7: Load-Bearing vs. Decorative: Stop Polishing the Wrong Things (Trust Walls pt 6)

    APR 1

    Episode 7: Load-Bearing vs. Decorative: Stop Polishing the Wrong Things (Trust Walls pt 6)

    Most businesses spend 80% of their energy on things that look impressive but don't actually hold weight. They perfect their Instagram aesthetic while their delivery model is broken. They redesign their logo while their unit economics don't work. Your business has two kinds of elements: load-bearing (the things that hold it up) and decorative (the things that just look good). The problem? Most people can't tell the difference. In this episode, we break down how to identify what's actually structural in your business, the danger of building decorative-first, and why effort spent on the wrong things doesn't create growth. Key Topics: The 5 load-bearing elements every business has (and the decorative ones most people obsess over) 5 diagnostic questions to figure out what's structural in YOUR business Why decorative work feels productive but doesn't build capacity When decorative becomes load-bearing (and vice versa) The two-list exercise to audit where your energy actually goes Free Download: Load-Bearing vs. Decorative Exercise: greyleafmedia.com/is-this-structural Resources: Brand Therapy: greyleafmedia.com/diagnostic Website: greyleafmedia.com Connect: LinkedIn - Jason Haeger

    27 min
  7. Episode 6: The Blueprint: Business Strategy vs. Just Being Busy (Trust Walls pt 5)

    MAR 30

    Episode 6: The Blueprint: Business Strategy vs. Just Being Busy (Trust Walls pt 5)

    Most businesses confuse being busy with making progress. They're launching campaigns, posting content, running ads, attending events but there's no plan connecting any of it. The difference between businesses that work and businesses that just look busy? One has a blueprint. The other is just stacking bricks. In this episode, we break down what a business blueprint actually is (it's not your goals or your vision), why most people skip this step and pay for it later, and how to know if you're building strategically or just reacting to whatever's in front of you. We cover the five components of every business blueprint and the critical difference between beautiful businesses that don't work and functional businesses that aren't beautiful yet. Key Topics: What a business blueprint actually is: the intentional design of how your business works as a system Why people skip the blueprint (and what it costs them) The 5 components: structure's purpose, system connections, customer journey, load-bearing vs decorative, build sequence The danger of decorative-first building Beautiful vs. functional: design for function first, then add form When to follow the blueprint vs. when to adapt strategically Resources: Brand Therapy Website: greyleafmedia.com Connect: LinkedIn - Jason Haeger

    31 min
  8. Episode 5: Building in Public: When Transparency Builds Trust (And When It Destroys It) (Trust Walls pt 4)

    MAR 27

    Episode 5: Building in Public: When Transparency Builds Trust (And When It Destroys It) (Trust Walls pt 4)

    Should you show people what you're building, or keep it private until it's perfect? The answer depends on what you're building WITH. Most people get this wrong. Transparency is trendy. "Build in public" is everywhere. But here's what nobody talks about: transparency only works if what you're building is actually solid. If your foundation is weak or your materials don't match your promise, transparency just reveals that faster. In this episode, we explore when building in public accelerates trust and when it destroys it, the difference between authentic vulnerability and performative transparency, and how to decide what to share vs. what to protect based on your foundation, materials, and personality. Key Topics: Why transparency works (and when it backfires) The three factors that determine whether to build in public: foundation, materials, personality Buffer, indie makers, open kitchen restaurants—examples of transparency done right Vulnerability vs. victimhood: the difference that matters When privacy builds more trust than transparency The decision framework: Does showing my work serve what I'm building, or just my ego? Resources: 90-minute diagnostic:  Brand Therapy Website: greyleafmedia.com Connect: LinkedIn - Jason Haeger

    19 min
  9. Episode 4: The Materials: Why Different Businesses Need Different Bricks (Trust Walls pt 3)

    MAR 11

    Episode 4: The Materials: Why Different Businesses Need Different Bricks (Trust Walls pt 3)

    In business, what you build WITH matters as much as what you build ON. Imagine standing in a brickyard with three options in front of you: premium bricks (expensive, last forever), standard bricks (solid, reliable), and cheap bricks (fast, but already cracking). Which should you buy? The answer depends entirely on what you're building. In this episode, we explore what you're building WITH—the materials that determine whether your business stands or collapses. We break down why different businesses need different "bricks," when each quality level is appropriate, and why the mortar (consistency, communication, follow-through, time) is what actually holds everything together. This is the missing piece most businesses ignore until it's too late. ⏱️ TIMESTAMPS 0:00 - Introduction: The Choice 3:12 - Different Businesses Need Different 'Bricks' 6:30 - Service vs Product vs SaaS vs Mission-Driven 9:42 - Quality Levels: Premium, Standard, Cheap 12:36 - The Mortar (What Holds It Together) 14:36 - Strategic Material Selection 16:38 - The Cost of Inconsistency 18:12 - Here's what I want you to think about 📌 KEY TAKEAWAYS Service businesses need relationship bricks; Product businesses need hard bricks; SaaS needs system bricks; Mission-driven needs integrity bricks Premium bricks = expensive in time/energy/money, signal quality over efficiency Standard bricks = reliable, repeatable, the backbone of most businesses Cheap bricks = strategic when testing, dangerous when permanent Mortar = consistency, communication, follow-through, and time Inconsistency destroys trust faster than low quality Materials must match your mission   🔗 RESOURCES Struggling to figure out which "bricks" your business needs? If you're mixing quality randomly, cutting corners you shouldn't, or watching competitors outpace you despite having a better product, you might have a materials problem. 📞 Book a Diagnostic: https://greyleafmedia.com/diagnostic/  – diagnose what's misaligned and build a strategy that actually grows your business. 🎧 More Episodes: https://greyleafmedia.com/podcast/    🌐 Our Services: https://greyleafmedia.com/services – Marketing strategy, positioning, and brand development for long-term growth. 💼 Connect on LinkedIn: Jason Haeger Grey Leaf Media ABOUT GREY LEAF MEDIA Grey Leaf Media helps businesses build brands that convert. We believe profit and purpose don't have to be at odds, and we prove it through strategic clarity that drives growth. This is the Trust Walls series: exploring how trust is built, brick by brick, in business.

    20 min
  10. Episode 3: The Foundation: What You Build ON Determines What Stands (Trust Walls pt 2)

    MAR 11

    Episode 3: The Foundation: What You Build ON Determines What Stands (Trust Walls pt 2)

    The Foundation: What you build on matters as much as what you build. There's a luxury apartment building in San Francisco that's sinking. Millennium Tower: 58 stories, hundreds of millions of dollars invested, and a beautiful glass facade. It's tilting 16 inches because the foundation wasn't anchored to bedrock. You see this in business all the time: A beautiful brand with impressive marketing and growing revenue. Then overnight, collapse. Because the foundation was never solid. In this episode, we explore what actually goes into a business foundation, why most companies skip this work entirely, and what happens when the ground shifts underneath even the strongest structures. ⏱️ TIMESTAMPS 0:00 - Introduction: The Sinking Tower 1:54 - Digging Down Before Building Up 5:57 - What Goes in the Foundation 11:52 - The Cost of Skipping Foundation Work 15:00 - The Shifting Ground (Blockbuster, Kodak, Netflix) 20:00 - Winterizing Your Foundation 24:30 - Closing Thoughts 📌 KEY TAKEAWAYS • The taller you want to build, the deeper you need to dig first • Your foundation = your values, why, who you serve, what you stand for/against • Foundation work is invisible, slow, expensive—but determines everything • Markets shift: your WHY stays constant, your HOW must evolve • Winterize before the cold comes: diversify, build reserves, insulate 🔗 RESOURCES Struggling with your business foundation? If your decisions feel chaotic, your team doesn't know what you stand for, or you're building fast but it doesn't feel sustainable—you might be building without a foundation. 📞 Book a Brand Therapy Session: https://greyleafmedia.com/diagnostic 90 minutes to identify what's missing and build a path forward 🎧 More Episodes: https://greyleafmedia.com/podcast/ 🌐 Our Services: https://greyleafmedia.com/services  Marketing strategy, positioning, and brand development for mission-driven businesses Web development, web maintenance, logo design, brand voice creation, marketing strategy, and more. 💼 Connect on LinkedIn: Jason Haeger Grey Leaf Media ABOUT GREY LEAF MEDIA Grey Leaf Media helps businesses build brands that convert. We believe profit and purpose don't have to be at odds, and we prove it through strategic clarity that drives growth. This is the Trust Walls series: exploring how trust is built, brick by brick, in business.

    27 min
  11. Episode 2: The Anatomy: How Trust is Built Brick by Brick (Trust Walls pt 1)

    MAR 11

    Episode 2: The Anatomy: How Trust is Built Brick by Brick (Trust Walls pt 1)

    Imagine standing in front of two walls. One represents a major brand: tall, polished, millions of dollars invested. The other was built by a person you just met.  Which do you trust more? The answer reveals everything about how trust actually works in business. In this episode, we explore the trust wall framework: how trust is built brick by brick, why brands start at zero while people start with lent trust, and the difference between recoverable mistakes and catastrophic collapse. ⏱️ TIMESTAMPS  0:00 - Introduction 1:23 - The Trust Wall Metaphor 3:51 - Why Brands Start at Zero 6:28 - Lent Trust: The Human Advantage 9:30 - How Trust Gets Damaged 13:15 - Practical Applications & Closing 📌 KEY TAKEAWAYS Trust is built brick by brick through consistency and integrity Brands start with zero trust; people start with lent trust Referrals work because you're borrowing someone else's trust wall Some trust violations can be repaired; others cause total collapse Person-to-person marketing works because of our shared humanity 🔗 RESOURCES Need help building trust with your market? If you're struggling with inconsistent messaging, low conversions, or unclear positioning, that's a trust-building problem. 📞 Book a Growth Diagnostic Session:  https://greyleafmedia.com/diagnostic/ - diagnose what's holding your business back and build a path forward in as little as 90 minutes. 🌐 Our Services:  https://greyleafmedia.com/services - Marketing strategy, positioning, brand development for mission-driven businesses, and implementation offerings. 💼 Connect on LinkedIn: Jason Haeger Grey Leaf Media ABOUT GREY LEAF MEDIA Grey Leaf Media helps mission-driven businesses build brands that convert. We believe profit and purpose don't have to be at odds, and we prove it through strategic clarity that drives growth.

    19 min
  12. Episode 1: The Three Gaps: Why Marketing Fails Mission-Driven Businesses

    MAR 10

    Episode 1: The Three Gaps: Why Marketing Fails Mission-Driven Businesses

    You're doing meaningful work. Your team cares deeply. Your mission matters. So why isn't growth happening the way it should? Welcome to Grey Leaf Media: the podcast for mission-driven business leaders who are done spinning their wheels. In this first episode, I break down why good work alone isn't enough for great growth, and introduce the three critical gaps holding most purpose-driven businesses back. The Three Gaps: The Clarity Gap - Your team describes what you do seven different ways  The Systems Gap - You're stuck in tasks instead of building strategy  The Positioning Gap - You're serving everyone, so you resonate with no one  These gaps don't just slow growth—they burn out founders, frustrate teams, and leave money on the table that could be funding MORE impact. Featured content: The Clarity Audit: A 30-minute exercise you can do this week to identify which gap is costing you the most. ⏱️ Timestamps: 00:00 - Introduction: The Solar Company Story 01:00 - Who This Podcast Is For (And Who It's Not For) 02:28 - The Three Critical Gaps 5:49 - The Clarity Audit (Take Action This Week) 7:35 - Remember This 7:55 - Closing --- 👋 About Me: I'm Jason Haeger, founder of Grey Leaf Media. I've spent years building marketing operations, brand strategies, and growth systems from the ground up for companies across finance, law, healthcare, sports writing, and more. I help businesses build trust and achieve lasting growth by aligning their strategy with the impact they're trying to make. 🔗 Connect: LinkedIn: Grey Leaf Media company page (https://www.linkedin.com/company/grey...) Website: https://greyleafmedia.com Instagram/Threads/Facebook: @greyleafmedia 📅 New episodes coming soon. Subscribe.

    9 min
  • 12 Episodes

About

Marketing Notes for Entrepreneurs by Grey Leaf Media is for marketers, founders, and leaders of impact-driven businesses. We look at common problems, unexpected solutions, and strategies to help grow your impact. Growth is more than profits, it is measured in tangible positive impact. Without growth, your impact stalls. Featuring: The Trust Wall series! A unique look at how to think about progress, mistakes, consistency, and growth. Episodes 2-8 This podcast is brought to you by Grey Leaf Media. Marketing consulting, strategy, and marketing technology solutions for business that matters.

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