Marketing Notes for Entrepreneurs

Jason Haeger | Marketing Strategist for Entrepreneurs
  • 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 19: Bringing People to the Family Table: How to Sound Like the Same Brand in Every Room

    3d ago

    Episode 19: Bringing People to the Family Table: How to Sound Like the Same Brand in Every Room

    Your brand doesn't have to sound identical everywhere to be consistent. When it does, it usually stops connecting. The most consistent brands aren't the ones with a locked-down tone guide. They're the ones that know exactly what's allowed to change. This episode uses a single extended analogy, a family Italian restaurant three generations deep, to show how the same brand can sound completely different depending on who's talking, who they're talking to, and what room they're in. The uncle drawing in the neighborhood crowd sounds nothing like the cousin pulling in his friends. But both are protecting the same recipe. The distinction between what has to stay constant and what's allowed to flex is the difference between a brand that connects everywhere and one that struggles to be visible. Topics covered: Why brand voice consistency is applied at the wrong level in most businesses The difference between the recipe and the delivery, and why confusing them breaks every channel at once What the uncle and the cousin can teach you about multichannel marketing voice How Mailchimp ran three completely different rooms for two decades, and what Intuit actually paid $12 billion for Three diagnostic questions to tell whether your recipe is working across every room your business shows up in If you can answer those three questions honestly, you'll know whether your brand is protecting the right thing, or whether the rooms have drifted so far from the kitchen that nobody can recognize the aromas anymore. Resources mentioned: Brand Therapy diagnostic: greyleafmedia.com/diagnostic

    25 min
  2. Episode 18: The Living ICP: Your ICP Was Right Once. Is It Still?

    Jun 12

    Episode 18: The Living ICP: Your ICP Was Right Once. Is It Still?

    Your ICP was right once. Then the market moved, your customers changed, and your business kept acting like nothing had happened. That's ICP drift -- and it's quieter and more common than building the wrong ICP from the start. This is the tenth and final episode of the "Your ICP is a Lie" series -- and the one that asks the hardest question: not whether your ideal customer profile was ever right, but whether it's still right now. Most ICP drift doesn't look like failure. It looks like friction. The same friction this series has been describing for nine episodes -- messaging that requires more explanation than it used to, pricing that gets more pushback, retention that looks stable but feels hollow. Sometimes those symptoms aren't about a wrong ICP. They're about a right ICP the business hasn't followed. This episode covers: Why every ICP starts as a snapshot -- and why snapshots don't update themselves What ICP drift actually looks like, and why it arrives wearing the clothes of previous success Netflix and Qwikster: the cost of managing drift without committing to it Slack: what observation as a practice looks like when the original plan fails The permaculture principle that reframes the ICP from a document to a relationship Three things worth building into your business rhythm to catch drift before it compounds The living ICP isn't a deliverable. It's a posture. And that posture is what this entire series has been building toward. New to the show? This series started at Episode 9. If today's episode landed for you, go back and work through the full arc -- it builds deliberately. The Trust Walls series starts at Episode 1 if you want the foundation underneath all of it. Resources mentioned: ICP Toolkit (free, 15 pages): greyleafmedia.com/find-your-icp Brand Therapy diagnostic: greyleafmedia.com/diagnostic

    21 min
  3. Episode 17: How a Wrong ICP Breaks Everything at Once: Why Your Marketing Fixes Keep Not Working

    Jun 5

    Episode 17: How a Wrong ICP Breaks Everything at Once: Why Your Marketing Fixes Keep Not Working

    If you've been fixing the same marketing problems over and over — better messaging, smarter pricing, tighter retention — and nothing stays fixed, the problem probably isn't your execution. Every system in your business may be broken by the same root cause. When your ideal customer profile is wrong, it doesn't break one thing. It breaks everything downstream at once. This is the cascade effect — a systematic pattern where a wrong ICP corrupts messaging, sales, pricing, and retention simultaneously, and where fixing any one of those systems in isolation produces only temporary improvement. The problem isn't performance. It's alignment. And you can't fix an ecosystem mismatch by optimizing the organism. This episode covers: Why strong execution in the wrong environment still produces weak results How a wrong ICP breaks every downstream marketing system simultaneously Why marketing fixes plateau quickly when the root cause is upstream What alignment between ICP and business systems actually looks like Where to start when you recognize the cascade in your own business An ecology framework — niche, environment, ecosystem fit — runs through the episode as the connective analogy. Because the cascade effect isn't a marketing problem; it's an alignment problem. And the fix always starts in the same place. Part 9 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

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

    May 29

    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
  5. 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
  6. 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
  7. 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
  8. 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
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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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