Happy Sunday, Everyone!
I hope you’re all staying cool amidst the heat wave blanketing much of the US and Europe – as you’re reading this, we’re all enjoying Rome’s blissful, 102-degree heat on the last stop of our family’s summer vacation.
And, speaking of heat - this week’s issue is a different one, inspired by the one-and-only Cory Henke (who reminded me to re-share and promote the greatest hits) – it’s 7 of the most-read, most-searched for issues from the Digital Download, summarized and updated for 2025.
Over the last 2.5 years, this newsletter has grown from 103 subscribers to nearly 7,000 (yeah, crazy) – and now has readers on 6 continents, nearly half of the Fortune 500 who collectively manage billions (likely hundreds of billions) in paid media spend. So, whether you’ve been along for the entire ride (thank you!) or you’ve just joined, I hope you’ll find it helpful, informative and maybe just a little insightful.
And with that - the single-most read issue of the Digital Download is:
Issue #78 | A Better Way To Think About The 95-5 Rule
This was one of my favorite issues of the last year - and is one I highly recommend everyone (in-house, agency, freelancers, investors, operators) read. It focuses on the “95:5 rule,” which states that ~95% of people who interact with your brand (visit a website, use your app, consume content) aren’t in-market to buy at that particular moment in time, leaving only 5% who are ready to purchase/commit to a next step. The conclusion: the vast majority of even hyper-targeted marketing investments will be directed toward individuals who are unlikely to convert right now.
The flaw that most marketers make is treating the 95:5 rule as binary (ready-to-buy or not) when, in reality, intent exists along a relatively wide spectrum. Our data (and the data from hundreds of brands) shows that beyond the ~5% ready to buy, there’s a significant group of “undecided” or “fence-sitting” users (around 7-15%) who are genuinely interested but not fully committed, and another 15-25% who are curious but lack immediate commercial intent. Everyone else is in an exploratory/low-intent state.
The problem is that most performance marketers focus too heavily on the top 5%, who are quite likely to convert regardless of further interventions (i.e. more marketing), instead of influencing the larger group of fence sitters. Moving even a small percentage of this undecided group can result in transformational increases in sales/leads, whereas obsessing over minor improvements in the top 5% yields marginal returns relative to effort.
To capitalize on this, marketing should:
- Increase conversion probability of fence sitters by adding softer CTAs, diagnostic tools, storytelling, and links to other resources to nurture interest.
- Maximize the total expected value of the audience, not just immediate transaction value, by capturing emails or other goal completions that correlate with future sales.
- Minimize spend on near-zero probability users who will never convert.
Ultimately, marketing is about maximizing the expected value of the entire audience – not just squeezing incremental returns from the small group already ready to buy.
Issue #92 | 9 Strategies For Shifting Customers From Promotion to Premium
This issue tackled a problem most brands face but few solve: what happens after your big sale. Whether it’s Black Friday/Cyber Monday in retail, Spring promotions in home services, post-holiday booms in senior care, or end-of-fiscal pushes in SaaS, nearly every industry has “momentum windows” where customer acquisition spikes. But what I’ve seen across countless brands is that while immense effort goes into running these promotions, little thought is given to what follows.
And that leads to what I call the “Fatal Five”:
- Margin Compression. Promo cohorts become addicted to discounts, only purchasing again during future sales, eroding margins or requiring perpetual promotions to retain them.
- Feast-or-Famine Cycles. Brands scale up for demand spikes only to find these customers aren’t as valuable, creating operational strain and unpredictable revenue.
- Customer Behavior Adaptation. Discounts train customers to wait for the next sale, lowering perceived value.
- Brand Equity Erosion. Frequent sales cheapen brand perception, making premium customers feel alienated and driving up negative reviews from price-sensitive buyers.
- Market Position Decline. With compressed margins and diluted brand equity, brands lose ground to competitors innovating or maintaining exclusivity.
Discounting isn’t inherently bad, but relying on promotions without a strategic post-purchase transition plan creates a treadmill of diminishing returns. To counter this, I outlined nine tactical frameworks to shift customers from promo to premium:
- Immediate Value Correction. Deploy intensive welcome journeys in the first 72 hours to reinforce your premium positioning, educate customers, and frame their “deal” as rare and earned by their timing or intelligence – not just your generosity.
- Value-Add Ons. Introduce upsells or bundles post-purchase to reset the discount anchor and rebuild full-price buying behavior. Most customers are bad at math; well-structured add-ons feel like wins while restoring margins.
- Tiered Price Normalization. Gradually reduce discounts in follow-up promotions, pushing late buyers toward higher-margin products and reinforcing the original buyers’ perception that they secured the best deal.
- Value-Based Price Anchoring. Use calculators, peer comparisons, exclusivity demonstrations, and interactive tools to shift focus from price to value delivered.
- Exclusivity-Based Loyalty Programs. Structure multi-tiered rewards that incentivize full-price purchasing with prestige-based benefits, not discounts, reframing the customer relationship around status rather than cost savings.
- Premium Product/Service Cross-Pollination. Analyze promo cohort purchase paths to identify entry points correlated with higher LTV, then structure future promotions to drive new customers into those paths.
- Propensity-Based Reactivation Campaigns. Replace blanket reactivation emails with AI-driven propensity models to target likely buyers and send “break-up” emails to the rest, creating pattern breaks and leveraging loss aversion.
- Non-Traditional Content Monetization. Gate premium content behind activities or data submissions that only high-value prospects can/will complete, strengthening your sales pipeline while filtering out low-intent users.
- Loss Aversion Engineering. Grant promo customers temporary premium status, highlight benefits, and then remove it gradually, driving reactivation via loss aversion triggers.
The common thread is simple: stop treating discount customers as inferior or static. With the right interventions, these cohorts can become some of your most valuable buyers, but only if you move quickly to reframe their relationship with your brand from price-based to value-based.
As we enter 2025’s prime “promo-season” (Prime Day, Back to School, BFCM), remember: the true ROI of any promotion isn’t just the initial influx of customers. It’s how many you can convert from promo to premium.
Issue #80 | 23 Meta Ads Pitfalls & How To Avoid Them
After auditing hundreds of Meta accounts – from <$10k/month to >$1M/month – I’ve seen four major drivers behind underperformance, with a total of 23 unique pitfalls (in order to keep this issue under control, I’ve summarized the main drivers; if you want to read all of the pitfalls, check out this issue!)
Group #1: Preparation & Research.
Meta’s aggressive push (and performance marketer’s acceptance) of broad targeting (driven by Meta’s Power-5 campaign) has eroded the advantage broad once offered. Early on, broad targeting worked because Meta’s algorithms funneled ads to a small, underserved/under-targeted-but-purchase-happy segment of the user base. But as every advertiser piled in, competition saturated these audiences and plucked all the low-hanging fruit. That’s led to an ecosystem where more advertisers are fighting for relatively few “purchase-happy” customers (remember: surplus value declines with adoption!). Now more than ever, success on Meta requires zigging where others zag: reinvesting in audience research, building sharp LALs and interest stacks, and segmenting first-party data to guide Meta’s machine learning in smarter-but-less-traveled directions. In short, stop abdicating strategic thinking to Meta. Point the machine in the right direction and give it a firm kick in the derriere.
Group #2: Budgeting, Metrics & Data Flows.
Data is table stakes on Meta – CAPI, clean integrations, and reliable flows are mandatory. But exceptional accounts go further with robust forecasts integrated into reporting, enabling proactive optimization. High performers also set realistic budgets (campaign daily budget = # of ad sets * 7.25 * tCPA) to avoid starving campaigns. Crucially, they set distinct KPIs for new customer acquisition vs. existing customer activation, ensuring they don’t mortgage future growth for short-term ROAS boosts from remarketing alone.
Group #3: Account & Campaign Structure.
There’s no universal “perfect structure,” but common pitfalls are rampant: too many micro-campaigns fragmenting data; no coherent testing strategy; optimizing for bullshit metrics (clicks, engagements) instead of revenue actions; trying to outsmart Meta with psychographic voodoo rather than doing the basics brilliantly; ignoring whitelisting with creators; missing exclusions; neglecting comment management; and forgetting fundamentals like price bucketing DPAs or aligning creative, offer, and audience.
Group #4: Creative Strategy, Process & Implementation.
Despite all the structural and data factors, creative remains the #1 performance driver. Most brands lack a true creative strategy, produce insufficient volume (no creative velocity), and run generic one-size-fits-all ads. Other common issues include uploading TV spots without optimization, lacking creative diversity, overproducing inauthentic ads, obsessing over features instead of benefits, ignoring hook testing, copying competitors wholesale without differentiation, and failing to track creative diagnostics (hook rate, thumbstop, hold).
The common thread that connects all 4 groups:
Great Meta performance isn’t magic. It’s the outcome of disciplined preparation, realistic budgeting, robust forecasting, clear KPI splits, coherent campaign structure, and a relentless commitment to strategic, audience-relevant creative.
If this felt like a laundry list of issues your account faces, you’re not alone. Nearly every Meta account I’ve audited has room for improvement. But acknowledging the gaps is the first step. Meta is unforgiving to laziness but immensely rewarding to marketers who do the work daily to build, iterate, and optimize systematically.
Issue #79 | What's Next In Paid Media?
I wrote this issue just over a year ago - and in re-reading it this past week, I think it may be more relevant now than it was then. There’s no denying we’re living in (and marketing through) turbulent times – the first half of 2025 has had more action than some decades. We’ve already endured a trade war, a hot war, a supply-chain crunch, multiple attempts at tech regulation, an inflation scare, an Eagles Super Bowl win (sorry, had to) and more than a few natural disasters. It’s been a year. It’s still June.
But, in times like these, where attention gets scarcer, costs rise, and control levers erode, advantage comes from doing what others aren’t. This issue focused on 3 high-impact ways to build that advantage:
1. Do More Audience Research.
Audience understanding has gone from important to imperative. Most brands rely on stale intuition and gut feel. High-performing brands invest in structured research, including:
- Keyword Research: Integrating Search Terms Reports, Paid & Organic data, customer surveys, competitors, and Google Trends to evolve keyword sets and uncover untapped opportunities.
- Customer Insights Emails: Sending daily personalized emails from senior leaders asking customers why they chose (or didn’t choose) the brand, what competitors they considered, and what they wish the brand offered. Automating these insights via Gmail folders, Zapier, and ChatGPT surfaces patterns while creating an early-warning system for churn risks.
- Third-Party Tools: Tools like SparkToro remain underused despite their unmatched ability to map influence sources for targeting, PR, sponsorship, or creative inspiration.
In a world where “broad-only” is worshipped, remember: creative alone isn’t targeting. Smart machines need smart data to outperform. Brands that invest here will outpace competitors relying purely on platform algorithms.
2. Find Under-Valued Attention.
When I wrote this issue, we were staring down the reality that Q4 2024 wouldn’t just be saturated - it was poised to be (and was) the most expensive digital ad market in history. But, records are made to be broken. We don’t yet know what Q4 2025 will hold (that will start to take shape in the next 2-3 months), though I’m quite confident it will give 2024 a run for its money. That makes it all the more important for brands to find the under-valued attention (yes, it still exists!):
- X (Twitter): CPMs as low as $0.48 with solid conversion rates make it an arbitrage play despite platform volatility.
- YouTube Shorts: Watch time growth continues to outpace ad budgets, creating value buys for brands with solid short-form creative.
- YouTube In-Feed: This is a new addition, but in-feed creative has been incredibly cheap (and incredibly effective) – YouTube is rapidly becoming the world’s most effective discovery engine, and in-feed ads are shockingly under-priced right now.
- Podcasts & Newsletters: Often undervalued if brands fail audience research; knowing exactly which podcasts or newsletters your audience consumes unlocks major efficiency.
- Linear TV: Political campaigns often cancel reserved inventory last-minute. Brands ready to move fast with known target slots can secure massive (50%+) discounts.
- LinkedIn: While expensive relative to normal Meta/Google rates, LinkedIn remains stable and comparatively cost-effective during election-season digital inflation.
There’s more than one way to win in competitive markets: you can pay more, or you can play smarter. I don’t know about you, but if given the choice, I’ll happily play media moneyball and take advantage of the value everyone else misses.
3. Leverage CRM + Offline Data.
Despite privacy changes, few brands fully utilize offline conversion tracking via Meta CAPI or Google Offline Conversions. Yet shifting optimization from basic form fills to qualified leads, retained purchases, or non-churn subscribers can transform performance:
- Create workflows to pass enriched conversion data from website forms to Google Sheets.
- Add qualification or purchase details.
- Trigger offline conversions based on those qualified events.
- Shift primary optimization actions to these events.
It’s not rocket science. In under an hour, virtually any marketer can implement the system. Once you do, the results speak for themselves: one client saw qualified lead rates jump from 11% to 62%; another quadrupled booked calls. Ad platforms give you exactly what you ask for, so ask for outcomes that actually move your business forward.
Each of these areas - audience research, under-valued attention, and offline data leverage - is a force multiplier on its own. Combined, they future-proof your marketing in a world where platform changes, economic cycles, and competitive saturation are only accelerating.
Issue #74 | 8 Hard-Learned Advertising Lessons
I (apparently) had a pretty significant winning streak in the 70s (unlike the US), with this issue cracking the Top-9 most read and most-commented issues. After re-reading it, this is honestly one of the issues I’d recommend to any person getting started in advertising/marketing (or really, business in general). My grandfather always told me, “You always pay to learn - but they don’t tell you the price until the lesson is over.”
This issue is an attempt at paying it forward, so you can learn from some of the more expensive mistakes I’ve made (hopefully, with a far lower tuition cost):
Lesson #1: Clear Beats Clever.
Most marketers write clever copy to impress themselves or peers, but clarity sells. Simplicity matters because a large portion of the audience reads at or below an 8th grade level. If a drunk person can’t understand your offer in 3 seconds, it’s too complicated. Clear + Simple = Understanding; Understanding + Surplus Value = Sales.
Lesson #2: The Best Ads Aren’t Ads.
People hate ads, but love authentic, relatable content. “Anti-ads” – unpolished, organic-feeling creatives – outperform slick, brand-centric commercials. Study what your audience consumes organically and make ads that feel the same.
Lesson #3: The Hook Is 80% of the Ballgame.
If your hook sucks, no one sees the rest of your ad. Obsess over the first 3-10 seconds. Script multiple hook variants and treat it like a chess opening: a strong opening shapes the entire game.
Lesson #4: Make More Ads.
Quantity drives quality. Creative performance is power-law distributed: a small minority of ads yield the majority of positive outcomes (sales, leads, subscriptions). Increase volume, keep marginal production costs low, and accept small losses to find your winners faster.
Lesson #5: Align Ads, Offers, and Landers.
Many brands kill performance by misaligning ad messaging with landing page content. Ensure consistency in offers, products, visuals, and audience targeting throughout the funnel to avoid confusing and losing prospects. It makes no sense to have 1,000 ads that talk to a dozen different audience segments, all going to a handful (or worse, a single) lander. Stress test your entire funnel, from the ad impression through the entire post-click experience. If you don’t think it’s remarkable, odds are your audience won’t, either.
Lesson #6: Most Tests Should Be Big Swings.
Incremental testing has its place, but big swings (radical offers, new products, bold positioning) are what drive exponential growth. Too many brands make the mistake of relying on incrementalism - and they end up optimizing themselves into mediocrity. The brands that win are the ones that take big, bold swings + seek out breakthroughs that can fundamentally shift the business.
Lesson #7: Roll With The Tides.
Don’t try to manufacture demand and urgency simultaneously. Instead, align marketing pushes with natural demand peaks (holidays, seasonality, fiscal year starts) and ride those waves for greater efficiency and volume.
Lesson #8: Miss In The Right Spot.
Success is less about hitting the perfect shot and far more about minimizing downside risk while maintaining upside. Build simple structures, leverage data-informed targeting, deploy clear messaging, and set budgets/targets smartly. Set up your campaigns so that even misses leave you in an acceptable position to “make par.”
My big takeaway: 90% of success in marketing isn’t a result of flashy campaigns or marketing heroics. It’s built on doing the simple, boring things remarkably well and consistently. While everyone remembers the sexy campaign, the reality is that those campaigns only succeed because the fundamentals are so well-executed, they’ve become invisible.
Issue #120 | The AI Reality Check
Over the last ~24 months, it’s been impossible to talk about anything in marketing without mentioning the thing at the forefront of everyone’s mind: AI.
But, after the spring conference season (plus way too many to count conversations), I’ve come to the conclusion that we (collectively) are on the precipice of the AI valley of disillusionment.
Put another way: there’s a staggeringly large gap between the polished demos we all are being shown at events, on X and on “AI-powered” SaaS websites and what AI tools can reliably deliver day-to-day for the vast majority of brands. Most CMOs + marketing execs think AI will replace entire departments – but the on-the-ground reality is that most teams can’t get it to produce consistent on-brand copy or functional code.
Part of that is, without question, user error (or user inexperience) – but that, in and of itself, is an indictment on the state of AI. The promise of AI isn’t to replace one deterministic set of instructions (most workflows were glorified if-then sequences) with a more opaque, probabilistic one (after all, what good is it if we need to memorize crazy prompts just to get a usable result – all we’ve done in that case is traded one set of instructions for a book of incantations – that hardly seems like progress) – it is to augment human intelligence and capacity in previously imaginable ways.
That just has not happened yet.
But, here’s the reality: friction is your opportunity. When a tool becomes easy for everyone, its competitive advantage goes to zero. Right now, GenAI is weird, inconsistent, and counterintuitive – which means most people give up. The winners will be those who accept what AI can do today and integrate it to multiply their teams’ productivity, freeing up time for truly strategic, human marketing work.
This issue contained seven practical AI use cases we’re deploying now to do just that:
- Competitive Intelligence Automation.
Use Gemini or ChatGPT to scrape, summarize, and trend competitor offers, messaging, and positioning weekly – freeing up 10+ hours per month and equipping you with insights to act faster than competitors.
- Audience Segmentation & Virtual Personas.
Segment your customer or lead files, feed the segments into SparkToro for behavioral insights, then build custom GPTs to act as “virtual personas” for ad testing, offer validation, and content feedback – creating an always-on focus group.
- Search Term Cleanup at Scale.
Upload your keyword lists and search terms to AI to rate relevance (0-10). Quickly exclude irrelevant queries, identify new ad group opportunities, and stop budget bleeds – critical for Performance Max campaigns.
- Rapid Landing Page Prototyping.
Generate lander wireframes, copy blocks, and HTML/CSS prototypes within hours. Validate with your custom GPT personas before dev teams refine, cutting launch cycles from weeks to days.
- Ad Copy Generation & Pre-Testing.
Prompt AI to create dozens of headline/description variants for your personas, funnel stages, and offers, then run them through your virtual personas for resonance feedback – delivering faster, better creative without endless revisions.
- Content Repurposing at Scale.
Turn one blog post or podcast into LinkedIn posts, Twitter threads, YouTube scripts, Quora answers, short-form hooks, and visuals in minutes. Prioritize which content to repurpose based on persona resonance and competitor gap analysis.
- Real-Time Audience Feedback Loops.
Send a handful of personalized, plain-text emails each day to customers or prospects with a few questions. Pipe replies into Google Sheets via Zapier, summarize insights weekly with AI, and gain real-time churn risk, feature request, and language data to humanize your marketing.
My (unconventional) takeaway: the winning teams this year won’t be those chasing AI hype or moonshots. They’ll be the ones deploying these boring, effective workflows that save time, surface better insights, and let marketers get back to what matters most: crafting strategies, stories, and experiences that move people.
Skip the hype. Start building.
Issue #93 | Are You Ready for Q5?
Last, but not least, is the Q5 issue – it’s a bit early for 2025, but not as early as you might think. We’re already getting started on Q4 + BFCM planning for some brands, which means Q5 is next on the docket.
In the spirit of updating this for 2025, imagine we’re in early December: BFCM is over, the holiday rush is peaking, and smart marketers are already thinking beyond December – into Q5, that magical ~25 day window from the shipping cutoff (~Dec 21) to early January.
During Q5, ad costs drop as brands pause campaigns, while consumer attention skyrockets (gift cards, returns, cash-in-hand, more device time). B2B buyers are finalizing reports and strategic plans. Everyone is online, in-market, and thinking about change.
The smartest brands will leverage this with three approaches:
1. Build Relationships + Add Value
Most brands treat Q5 as a pure revenue period. The savvy ones see it as both revenue and relationship-building. Start by gathering data on net-new customers from BFCM and Holiday: surveys, quizzes, or personal outreach to understand their goals, challenges, and motivations. Use this to deliver educational, value-add content that helps them maximize what they’ve already purchased – not to immediately upsell, but to build trust and loyalty. For B2B brands, Q5 is prime time to re-engage dormant leads with insights, calculators, frameworks, and real solutions as decision-makers plan 2025.
2. Focus on Future-State Enablement
Q5 is driven by transition psychology. Move beyond “new year, new you” platitudes and create pathways that make desired outcomes feel inevitable, not just possible. Pair your product or service with concrete steps, plans, or accountability mechanisms. For B2B buyers worried about adoption risk, this eliminates objections. For consumers, it shifts from selling features to selling results they believe will happen. Ads during Q5 should obsess over the future state and position your offer as the vehicle + roadmap to get there.
3. Get a Head Start on Diversification
Most brands wait until January to test new channels. That’s a mistake. Q5 is the ultimate low-cost, low-risk testing window:
- Cheaper CPMs. Experimental platforms like Reddit, X, Snap, TikTok, LinkedIn, and YouTube Shorts see dramatically reduced costs.
- Accelerated learning. You gain 2-3 weeks of data before competitors even launch.
- Competitive differentiation. Capture low-hanging fruit while others sit out.
- De-risked tests. There’s no pressure, as December’s performance is already locked in. If it works, you’re ahead for 2025. If not, you pivot before the year starts.
At the end of the day, Q5 is a marketer’s cheat code. Understand the shift from Q4’s discount-driven mindset to Q5’s reflection and transformation focus. Build relationships, enable future results, and diversify before the calendar turns.
Run through the finish line of 2025 and hit 2026 at a sprint (yes, I’m really closing this issue on a point that we’re closer to 2026 than we are to Christmas 2024).
We’ll be back to our regularly-scheduled programming next week – but until then, stay cool!
Cheers,
Sam
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