Holiday marketing, as it’s preached, is a con. A ritualized scam sold to startups by ad platforms, agencies, and marketers who profit from your desperation. Do you really think you can outspend Amazon, out-charm Coca-Cola, or outmaneuver Nike? Unless you’re secretly printing money in your garage, no. Christmas isn’t for playing Santa with jingles and 20% off codes—it’s for hunting a whale. Next year, turn your entire marketing strategy into a public obsession with one person. Not a “demographic market.” Not a target persona. A single, breathing, flesh-and-blood human being whose “yes”could grant you permanent access to Cuban’s Cabo cocktail club. Bet it all on a campaign so precise it’s borderline psychotic. Dangerous? Stupid? Obviously, and probably. But boring? Never. If it crashes, people will talk. If it flies, you’ll own the year. Either is better than begging the Internet for clicks, plus it’ll give you a great story (or a great excuse to drink). Holiday Marketing Sucks. This is a classic David vs. Goliath scenario—except Goliath has a machine gun and David forgot his slingshot. Here’s why it’s a losing battle: You’re Outgunned And Outclassed Every big brand with deep pockets is jacking up CPMs. Ad costs more than double, competition spikes, and algorithms prioritize whoever spends the most. Yeah, obviously not you. If your $10K campaign could talk, it would whisper: "Help." You’re Selling To Zombies By mid-December, your CTA is competing with drunken relatives, shipping delays, and 87 ads about the perfect gift for canine therapists. Your audience is fried and their brains are coasting on autopilot—barely capable of choosing between two brands of wrapping paper. You’re Competing With Santa Claus—Not Other Businesses Know why Apple kills it every Christmas? It’s not with Siri, but with sentiment. The holiday giants use their war chests to craft masterpieces that ride on the emotional meaning of the season—nostalgia, tradition, family values—and if you’re not on par, you come off like a door-to-door salesman in a Saint Nick suit. ROI = Regret On Investment December sales bring January sobs. Whatever you make from your festive push will be eaten alive by your CPA—and you’ll wake up next month drowning in remorse, invoices, and wondering where the cash went. (Hint: Zuck’s back pocket) Why Serenading One Person Is The Smartest Play The best presents don’t come in mass-produced packages. Neither should your holiday marketing. A custom campaign is as much a gift to them as it is to you. It’s Psychological Warfare People hate being sold to, but they love feeling chosen. Focusing on one person creates a psychological bind: If they respond, they know they’re winning because you’ve done all the work to court them.If they don’t respond, they wonder if someone else will—and if they’ll miss their shot. It’s The Ultimate Litmus Test For Your Product If you can’t convince one perfect-fit customer, how will you convince hundreds? A campaign por uno is the fastest way to figure out if your pitch, product, and strategy are sharp enough to scale. It’s The Best Marketing Boot Camp A one-person campaign is combat training. No crutches of generic strategies, no Canva, no “but our CTR was decent” excuses—survival here relies on raw ingenuity, superhuman agility, and uncompromising precision. Success isn’t guaranteed, but clarity is. The hard lessons will stick, and your team becomes immune to mediocrity. After this, they’ll be more than competent: they’ll be dangerous. It Turns Failure Into Success Even if it “fails,” it doesn’t. People appreciate balls. The audacity of your move becomes its own currency, generating buzz, controversy, and respect—all of which could bag you a new client, partner, or investor. In a one-person campaign, failure is just another kind of success. How To Execute A Campaign That Borders On Maniacal Step 1: Pick Your Whale A Dream Customer: E.g., the enterprise client whose logo would give your sales team goosebumps.A Key Partner: E.g., the CMO that could double your reach if they said yes.An Influential Investor: Not just for the check, but for the name on the cap table. Be ambitious, but realistic. Elon’s too busy running Government Efficiency. Aim for the guys two rungs below him. Step 2: Stalk Your Prey Just because you’re targeting one person doesn’t mean you get to skip the user insight phase. Oh no, this research matters even more when you’re professing love, and it doesn’t stop at their LinkedIn profile. Do they like having their ego massaged? Have a fetish for cryptic puzzles? Are they nosing around for gaming collaborations? Stalk (ethically), snoop (strategically), and build a dossier so good it’d make the FBI sweat. Just remember there’s a fine line between research and “why is there a black van outside my house?” Step 3: Unleash Controlled Madness. Now that you understand your whale’s appetite, cook up the bait. Go brazen, or don’t bother. But your bravado and performance art means nothing without an unapologetic CTA and irresistible pitch. That ask needs to be so direct it’s borderline confrontational, and that pitch better feel like a bespoke Italian suit. Here are some thought-starters: Sponsor Their Daily Coffee: Find out where they get their morning coffee and prepay for a week of their orders. Include a personalized note on every receipt that says: “Fuel for your next great decision—working with us.” Ship A Literal Door: Send them a door (yes, an actual door) with a key attached and a note: “This is the key to unlocking something extraordinary. Let’s talk.” Buy An Editorial: Call up some prestigious publication they subscribe to and splurge on a paid piece. Write an open letter addressed to them, full of specifics about why they should engage with you. Be cheeky: “Hey [Their Name], Playing Small Looks Weird on You.” Step 4: Make Sure The World Knows You’re Crazy. Exclusivity is no fun if no one’s watching. Turn your serenade into a spectacle. More thought-starters: Build a Public Countdown: Launch a countdown clock on social media, with posts teasing, “6 Days Until [Target’s Name] Changes Everything.” Make sure they’re mentioned, their employees are tagged, their peers are targeted. Go Guerrilla (Literally): Hire street performers or actors to “protest” outside their HQ, carrying signs with slogans like, “[Target’s Name], Take the Meeting!”. Extra karma if it’s themed to their industry or product. Rent Their Attention: Buy ad space outside their office. A billboard. Graffiti a building (legally). Be loud to the point you start the water cooler gossip: “Dear [Name], If You Don’t Call Us, We’ll Have to Buy More Billboards. And That’s Awkward for Everyone.” Final Thoughts: Maybe It’s Not You—Maybe It’s Just Dumb Sometimes, you’re not bad at the game—the game is (likely) a waste of time. Holiday marketing for startups? That’s the house always winning, with you just the festive confetti. Stop groveling for attention in a system that turns startups into cannon fodder for ad giants. That’s not persistence—it’s herd mentality dressed up as hustle. Do something irrationally ambitious. Go unhinged, go nuclear. Not because it’s guaranteed success, but because it’s not preordained defeat. At least you’ll have had some fun, and failed in style—on your own terms, not theirs. It’s Christmas. Use the season for what it’s meant for—walking away from bad ideas. Holiday marketing, as it’s preached, is a con. A ritualized scam sold to startups by ad platforms, agencies, and marketers who profit from your desperation. Do you really think you can outspend Amazon, out-charm Coca-Cola, or outmaneuver Nike? Unless you’re secretly printing money in your garage, no. Holiday marketing, as it’s preached, is a con. Christmas isn’t for playing Santa with jingles and 20% off codes—it’s for hunting a whale. Next year, turn your entire marketing strategy into a public obsession with one person. Not a “demographic market.” Not a target persona. A single, breathing, flesh-and-blood human being whose “yes”could grant you permanent access to Cuban’s Cabo cocktail club. Next year, turn your entire marketing strategy into a public obsession with one person. Bet it all on a campaign so precise it’s borderline psychotic . Dangerous? Stupid? Obviously, and probably. But boring? Never. so precise it’s borderline psychotic so precise it’s borderline psychotic But boring? Never. If it crashes, people will talk. If it flies, you’ll own the year. Either is better than begging the Internet for clicks, plus it’ll give you a great story (or a great excuse to drink). Holiday Marketing Sucks. Holiday Marketing Sucks. This is a classic David vs. Goliath scenario— except Goliath has a machine gun and David forgot his slingshot . Here’s why it’s a losing battle: except Goliath has a machine gun and David forgot his slingshot except Goliath has a machine gun and David forgot his slingshot You’re Outgunned And Outclassed You’re Outgunned And Outclassed Every big brand with deep pockets is jacking up CPMs. Ad costs more than double, competition spikes, and algorithms prioritize whoever spends the most. Yeah, obviously not you. If your $10K campaign could talk, it would whisper: "Help." If your $10K campaign could talk, it would whisper: "Help." You’re Selling To Zombies You’re Selling To Zombies By mid-December, your CTA is competing with drunken relatives, shipping delays, and 87 ads about the perfect gift for canine therapists. Your audience is fried and their brains are coasting on autopilot—barely capable of choosing between two brands of wrapping paper. You’re Competing With Santa Claus—Not Other Businesses You’re Competing With Santa Claus—Not Other Businesses Know why Apple kills it every Christmas? It’s not with Siri, but with sentiment . The holiday giants use their war chests to craft masterpieces that ride on the emotional meaning of the season —nostalgia, tradition, family values—and if you’re not on par, you come off like a door-to-door salesman in a Saint Nick suit. sentiment that ride on the emotional meaning of the season that ride on the emotional meaning of the season ROI = Regret On Investment ROI = Regret On Investment December sales bring January sobs. Whatever you make from your festive push will be eaten alive by your CPA —and you’ll wake up next month drowning in remorse, invoices, and wondering where the cash went. (Hint: Zuck’s back pocket) Whatever you make from your festive push will be eaten alive by your CPA Whatever you make from your festive push will be eaten alive by your CPA Why Serenading One Person Is The Smartest Play Why Serenading One Person Is The Smartest Play The best presents don’t come in mass-produced packages. Neither should your holiday marketing. A custom campaign is as much a gift to them as it is to you. A custom campaign is as much a gift to them as it is to you. A custom campaign is as much a gift to them as it is to you. It’s Psychological Warfare It’s Psychological Warfare People hate being sold to, but they love feeling chosen. Focusing on one person creates a psychological bind: If they respond, they know they’re winning because you’ve done all the work to court them. If they don’t respond, they wonder if someone else will—and if they’ll miss their shot. If they respond, they know they’re winning because you’ve done all the work to court them. If they don’t respond, they wonder if someone else will—and if they’ll miss their shot. It’s The Ultimate Litmus Test For Your Product It’s The Ultimate Litmus Test For Your Product If you can’t convince one perfect-fit customer, how will you convince hundreds? A campaign por uno is the fastest way to figure out if your pitch, product, and strategy are sharp enough to scale. It’s The Best Marketing Boot Camp It’s The Best Marketing Boot Camp A one-person campaign is combat training. No crutches of generic strategies, no Canva, no “but our CTR was decent” excuses—survival here relies on raw ingenuity, superhuman agility, and uncompromising precision. Success isn’t guaranteed, but clarity is. The hard lessons will stick, and your team becomes immune to mediocrity. After this, they’ll be more than competent: they’ll be dangerous. Success isn’t guaranteed, but clarity is. It Turns Failure Into Success It Turns Failure Into Success Even if it “fails,” it doesn’t. People appreciate balls. The audacity of your move becomes its own currency, generating buzz, controversy, and respect— all of which could bag you a new client, partner, or investor. In a one-person campaign, failure is just another kind of success. all of which could bag you a new client, partner, or investor. all of which could bag you a new client, partner, or investor. How To Execute A Campaign That Borders On Maniacal How To Execute A Campaign That Borders On Maniacal Step 1: Pick Your Whale Step 1: Pick Your Whale A Dream Customer: E.g., the enterprise client whose logo would give your sales team goosebumps. A Key Partner: E.g., the CMO that could double your reach if they said yes. An Influential Investor: Not just for the check, but for the name on the cap table. A Dream Customer: E.g., the enterprise client whose logo would give your sales team goosebumps. A Dream Customer: A Key Partner: E.g., the CMO that could double your reach if they said yes. A Key Partner: An Influential Investor: Not just for the check, but for the name on the cap table. An Influential Investor: Be ambitious, but realistic. Elon’s too busy running Government Efficiency. Aim for the guys two rungs below him. Step 2: Stalk Your Prey Step 2: Stalk Your Prey Just because you’re targeting one person doesn’t mean you get to skip the user insight phase . Oh no, this research matters even more when you’re professing love, and it doesn’t stop at their LinkedIn profile. Do they like having their ego massaged? Have a fetish for cryptic puzzles? Are they nosing around for gaming collaborations? doesn’t mean you get to skip the user insight phase doesn’t mean you get to skip the user insight phase Stalk (ethically), snoop (strategically), and build a dossier so good it’d make the FBI sweat. Just remember there’s a fine line between research and “why is there a black van outside my house?” Just remember there’s a fine line between research and “why is there a black van outside my house?” Step 3: Unleash Controlled Madness. Step 3: Unleash Controlled Madness. Now that you understand your whale’s appetite, cook up the bait. Go brazen, or don’t bother. But your bravado and performance art means nothing without an unapologetic CTA and irresistible pitch. That ask needs to be so direct it’s borderline confrontational , and that pitch better feel like a bespoke Italian suit. But your bravado and performance art means nothing without an unapologetic CTA and irresistible pitch. so direct it’s borderline confrontational Here are some thought-starters: Here are some thought-starters: Sponsor Their Daily Coffee: Find out where they get their morning coffee and prepay for a week of their orders. Include a personalized note on every receipt that says: “ Fuel for your next great decision—working with us. ” Sponsor Their Daily Coffee: Fuel for your next great decision—working with us. Ship A Literal Door: Send them a door (yes, an actual door) with a key attached and a note: “ This is the key to unlocking something extraordinary. Let’s talk. ” Ship A Literal Door: This is the key to unlocking something extraordinary. Let’s talk. Buy An Editorial: Call up some prestigious publication they subscribe to and splurge on a paid piece. Write an open letter addressed to them, full of specifics about why they should engage with you. Be cheeky: “ Hey [Their Name], Playing Small Looks Weird on You .” Buy An Editorial: Hey [Their Name], Playing Small Looks Weird on You Step 4: Make Sure The World Knows You’re Crazy. Step 4: Make Sure The World Knows You’re Crazy. Exclusivity is no fun if no one’s watching. Turn your serenade into a spectacle. More thought-starters: More thought-starters: Build a Public Countdown: Launch a countdown clock on social media, with posts teasing, “ 6 Days Until [Target’s Name] Changes Everything. ” Make sure they’re mentioned, their employees are tagged, their peers are targeted. Build a Public Countdown: 6 Days Until [Target’s Name] Changes Everything. Go Guerrilla (Literally) : Hire street performers or actors to “protest” outside their HQ, carrying signs with slogans like, “ [Target’s Name], Take the Meeting! ”. Extra karma if it’s themed to their industry or product. Go Guerrilla (Literally) [Target’s Name], Take the Meeting! Rent Their Attention: Buy ad space outside their office. A billboard. Graffiti a building (legally). Be loud to the point you start the water cooler gossip: “ Dear [Name], If You Don’t Call Us, We’ll Have to Buy More Billboards. And That’s Awkward for Everyone. ” Rent Their Attention: Dear [Name], If You Don’t Call Us, We’ll Have to Buy More Billboards. And That’s Awkward for Everyone. Final Thoughts: Maybe It’s Not You—Maybe It’s Just Dumb Final Thoughts: Maybe It’s Not You—Maybe It’s Just Dumb Sometimes, you’re not bad at the game—the game is (likely) a waste of time. Holiday marketing for startups? That’s the house always winning, with you just the festive confetti. Stop groveling for attention in a system that turns startups into cannon fodder for ad giants. That’s not persistence— it’s herd mentality dressed up as hustle . Do something irrationally ambitious. Go unhinged, go nuclear . Not because it’s guaranteed success, but because it’s not preordained defeat. At least you’ll have had some fun, and failed in style— on your own terms, not theirs . it’s herd mentality dressed up as hustle it’s herd mentality dressed up as hustle Go unhinged, go nuclear Not because it’s guaranteed success, but because it’s not preordained defeat. on your own terms, not theirs It’s Christmas. Use the season for what it’s meant for—walking away from bad ideas. It’s Christmas. Use the season for what it’s meant for—walking away from bad ideas.

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