Marketing Notes for Entrepreneurs

Jason Haeger
  • 5.0 (1)
  • Marketing
  • Updated Weekly

Most marketing advice tells you what to do. This show is about why things break — and how to think differently when they do. Marketing Notes for Entrepreneurs is for founders and leaders of impact-driven businesses who are tired of tactics that don't compound into anything real. We go deep on the systems, assumptions, and blind spots that keep good businesses from growing the way they should. Current series: Your ICP is a Lie — a look at how a wrong ideal customer profile quietly breaks your social media, content strategy, positioning, sales messaging, product development, pricing, and retention. Not one at a time. All at once. Brought to you by Grey Leaf Media — marketing strategy, brand positioning, and marketing technology for businesses that actually matter.

  1. Episode 16: How a Wrong ICP Breaks Your Retention: The Customers Who Stay Without Growing

    2d ago

    Episode 16: How a Wrong ICP Breaks Your Retention: The Customers Who Stay Without Growing

    If your retention looks healthy but growth still feels harder than it should, the problem probably isn't your retention strategy. It's who you're retaining. Wrong-ICP customers stay; not because the fit is right, but because switching is hard. This means your renewal numbers can look fine while the underlying relationship is barely surviving. No referrals. No expansion. No real engagement. Just inertia holding a customer in place until something shifts and they leave cleanly, without warning, and without a single thing you can point to as a failure. That's not churn. That's the cost of attracting the wrong customer in the first place. This episode covers: Why retention measures whether people left, not why they stayed The signature of wrong-ICP retention -- and what it costs beyond the obvious The silence before churn, and why it reads as contentment until it doesn't Why retention rate and NPS both miss this problem entirely How to diagnose it using the numbers most businesses aren't tracking What to do about it without churning customers who didn't do anything wrong Real example: AOL's subscriber numbers during the broadband shift -- millions of customers held in place by friction, not fit. The revenue looked real. The relationship wasn't. Part 8 of "Your ICP is a Lie" -- a 10-episode series on how a wrong ideal customer profile cascades through every system in your marketing. Resources mentioned: ICP Toolkit (free, 15 pages): greyleafmedia.com/find-your-icp Brand Therapy diagnostic: greyleafmedia.com/diagnostic

    14 min
  2. Episode 15: How a Wrong ICP Breaks Your Pricing: Why Customers Question Your Value

    May 22

    Episode 15: How a Wrong ICP Breaks Your Pricing: Why Customers Question Your Value

    If your pricing keeps stalling, or you keep attracting customers who negotiate everything, the problem probably isn't the price. It was set for a customer who isn't in the room. Most pricing problems aren't pricing problems. They're ICP problems. Every price you set is a market positioning signal. When your ideal customer profile is wrong, that signal is aimed at the wrong person before a single conversation happens: before your copy, before your pitch, before you have any chance to make your case. This episode covers: Why pricing is a communication problem, not a math problem The three ways a wrong ICP breaks your pricing strategy, including the margin damage that compounds quietly before it surfaces in your numbers How to read the diagnostic signals already hiding in your pricing conversations How to anchor pricing corrections to ICP clarity instead of competitive pressure Real examples: HP TouchPad, Starbucks and Dunkin' as deliberate market positioning choices, Basecamp's flat-fee model as ICP communication, and a personal story about pricing for one market while delivering at the level of another. Part 7 of "Your ICP is a Lie" -- a 10-episode series on how a wrong ideal customer profile cascades through every system in your marketing. Resources mentioned: ICP Toolkit (free, 15 pages): greyleafmedia.com/find-your-icp Brand Therapy diagnostic: greyleafmedia.com/diagnostic

    16 min
  3. Episode 14: How a Wrong ICP Breaks Your Product or Service: Why You Keep Building Features Nobody Asked For

    May 15

    Episode 14: How a Wrong ICP Breaks Your Product or Service: Why You Keep Building Features Nobody Asked For

    You built something real. It works. Customers are using it. Just not quite the way you built it to be used. That gap is one of the most expensive product positioning problems in marketing for entrepreneurs — and one of the hardest to see while it's happening. The product is shipping. Revenue is coming in. The team believes in the vision. What's underneath it, usually, is a set of assumptions about your customer that were never validated against the people actually buying. This episode looks at what happens when a wrong ICP gets locked into a product or service — through engineering time, design decisions, and roadmaps built on conviction instead of evidence. The Amazon Fire Phone and why it failed (it wasn't the wrong customer — it was wrong assumptions about what that customer would trust Amazon with). Google Glass, and the enterprise customers who raised their hand before anyone thought to ask. And a concept from urban design called desire paths that reframes what customer workarounds are actually telling you about your market positioning. What this episode covers Why wrong product failures are the most expensive ICP problem — and why they're invisible while they're happening The difference between Apple's ecosystem trust and Amazon's commerce trust — and why it matters for entrepreneur marketing strategy Vision without validation: how product roadmaps get defended by conviction instead of corrected by evidence Desire paths — what customer workarounds are actually telling you about where your product positioning should have been Google Glass and self-emerging validation: the right customer showed up before anyone thought to look How to talk to customers who stayed and customers who left — and what each conversation can and cannot tell you Resources Brand Therapy — if your product or service feels misaligned with who's actually buying: https://greyleafmedia.com/diagnostic Free ICP Toolkit (15 pages) — walks you through exactly who's actually buying from you and how to build your messaging around them: https://greyleafmedia.com/find-your-icp WordPress design, development, and hosting: https://greyleafmedia.com/services More episodes: https://greyleafmedia.com/podcast Connect on LinkedIn: Jason Haeger

    20 min
  4. Episode 13: How a Wrong ICP Breaks Your Sales Messaging: Why Your Sales Conversations Feel Like Pushing Uphill

    May 8

    Episode 13: How a Wrong ICP Breaks Your Sales Messaging: Why Your Sales Conversations Feel Like Pushing Uphill

    Most sales training tells you to get better at objection handling, sharpen your close, follow up more. And most of the time, that's not the problem. The problem is that your entire sales approach was built for a customer who isn't actually buying from you. When your ICP is wrong, your scripts, your objection handlers, your discovery questions — all of it is calibrated for a person who isn't in the room. The resistance you keep running into isn't sales resistance. It's a mismatch between who you think you're talking to and who you're actually talking to. This episode is about the difference between executing a script and understanding the person in front of you deeply enough to adapt to them in real time. That's a harder skill than most people want to admit — and it's also the one that actually changes outcomes. What this episode covers Why persistence in the wrong direction is stubbornness with a quota attached, not a sales skill problem The Encyclopaedia Britannica story: what happens when a world-class sales operation loses its ICP and can't adapt Why the weight of a transaction should determine the depth of the conversation, and what goes wrong when it doesn't The phantom objection problem: preparing for resistance your actual buyer doesn't have, while missing the concerns they do What it actually takes to understand your customer deeply enough that the script becomes internalized rather than performed Resources Brand Therapy: https://greyleafmedia.com/diagnostic Free ICP Toolkit (15 pages): https://greyleafmedia.com/find-your-icp WordPress design, development, and hosting: https://greyleafmedia.com/services More episodes: https://greyleafmedia.com/podcast Connect on LinkedIn: Jason Haeger

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

    May 1

    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
  6. 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
  7. 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
  8. 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
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About

Most marketing advice tells you what to do. This show is about why things break — and how to think differently when they do. Marketing Notes for Entrepreneurs is for founders and leaders of impact-driven businesses who are tired of tactics that don't compound into anything real. We go deep on the systems, assumptions, and blind spots that keep good businesses from growing the way they should. Current series: Your ICP is a Lie — a look at how a wrong ideal customer profile quietly breaks your social media, content strategy, positioning, sales messaging, product development, pricing, and retention. Not one at a time. All at once. Brought to you by Grey Leaf Media — marketing strategy, brand positioning, and marketing technology for businesses that actually matter.

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