Caribbean businesses are spending thousands of dollars on marketing every year — but here’s the real question:
Are they getting a return they can actually measure?
Can they tie their marketing activities directly to revenue?
Can they point to a campaign and say, “This generated sales, leads, or conversions?”
Ask that in any boardroom, and most businesses — if they’re honest — will have to say no.
Not because they aren’t trying.
Not because their teams aren’t talented.
But because the systems, strategy, and infrastructure to track real ROI just aren’t there.
I’ve been saying this for years:
The way we build and operate marketing in the Caribbean has to change.
But when Gary Vee dropped his keynote at the Possible 2025 conference — it was like someone finally said it on a global stage, with no filter and no diplomacy.
“Agencies aren’t competing anymore — they’re in crisis.”
“Stop spending to disguise bad creative.”
“If the content doesn’t work organically, don’t spend a cent on it.”
It was the global mic drop that echoed exactly what many of us on the ground already know:
The system is broken.
The strategy is outdated.
And the gap between what businesses want and how they operate keeps getting wider.
Now, with 2026 around the corner, we’re out of time.
Digital customers want convenience, trust, and personalized value.
Platforms have evolved.
AI is changing how we create, search, and transact.
But our marketing operations?
Still running on vibes, vanity metrics, and recycled campaign decks.
So I decided to go deeper.
To break down what Gary said — and respond to it like a sparring match.
Each round of this article unpacks a key moment from his keynote, followed by my take on how it applies (or doesn’t) to what’s happening in the Caribbean.
Because while Gary was talking globally, our regional crisis is very real.
And it’s time we stop pretending the house isn’t on fire.
The ONLY Video Every Marketer Needs To Watch Today | GaryVee @ POSSIBLE
🧠 Round 1: The ROI Illusion — Why Marketers Still Can’t Prove Results
🎤 Gary’s Take:
“There is actually, if I may with all due respect, zero reason to spend media dollars amplifying any piece of creative that has not been affirmed with organic reach in 2025.”
“For the first time in marketing history, the creative creates reach. That’s insane. And it creates reach based on relevance.”
🤜🏾 My Take:
Let’s start with the real question:
Can Caribbean businesses tie their marketing efforts to revenue?
In most cases — no.
Not because marketing doesn’t work… but because we haven’t built the systems to measure anything properly.
The infrastructure exists:
- You can build an e-commerce website.
- You can integrate payment gateways like WiPay, PowerTranz, SurePay, or Stripe.
- You can use Google Analytics, CRM tools, or conversion funnels.
But most businesses haven’t done any of it.
So what do we track instead?
Vanity metrics.
Likes. Shares. Reach. Impressions.
The superficial stuff — because it’s all we have access to when there’s no digital backbone.
Let’s go even deeper:
There’s nowhere in the Caribbean that teaches modern, real-world marketing rooted in attribution and digital performance.
No programs for content marketing.
No e-commerce curriculum grounded in our context.
And no institution building marketers who understand how to tie actions to outcomes.
So we’re stuck in a loop:
- Campaigns get launched with no funnel.
- Boosted posts go live with no conversion strategy.
- Agencies report inflated numbers.
- Marketers can’t prove value.
- And business owners — rightly — feel frustrated.
Gary’s point about organic validation before spending?
That’s not just a global standard. That’s a survival mechanism for regions like ours with limited marketing budgets.
If you’re not testing creative organically first…
If you’re not building systems to measure real results…
If you’re not connecting content to conversion…
Then marketing becomes a guessing game.
And ROI remains an illusion.
📊 Interesting Stats:
- E-commerce is projected to make up 21% of global retail purchases in 2025 — making digital infrastructure a non-negotiable (SellersCommerce).
- Most Caribbean businesses still lack e-commerce capabilities, CRM systems, or conversion tracking tools (Keron Rose).
🧠 Round 2: Rethinking Paid-First — Boosting Bad Creative Is a Waste
🎤 Gary’s Take:
“There is actually, if I may with all due respect, zero reason to spend media dollars amplifying any piece of creative that has not been affirmed with organic reach in 2025.”
“The creative is the reach. And most of you are spending to disguise bad creative, not amplify good creative.”
🤜🏾 My Take:
Caribbean businesses are still stuck in a “paid-first” mindset. The default response to underperforming content is:
“Boost it.”
“Throw a few dollars behind it.”
“Let’s hire a creator or run an ad.”
But here’s the truth — if that content didn’t perform organically, what exactly are you boosting?
You’re spending money to force-feed something the audience already told you they didn’t care about.
Worse yet, many marketers in the region don’t even have the space to test content organically first. Why?
Because everything they produce is tied to a campaign — and campaigns need to launch on time, regardless of whether the message is resonating.
That’s why most brands spend big money on bad creative. Not because they want to — but because the system they operate in doesn’t support real-time feedback, iteration, or in-house creative agility.
And let’s talk about the illusion of success.
Some of the very agencies getting awards for “best social campaigns” have content that got minimal engagement, zero shares, and no conversions.
But because they spent enough money to make it look like it worked, they walk away with a trophy.
This is what happens when campaign culture meets creative detachment.
There’s no audience testing. No organic validation. Just polished content, a paid media budget, and hope.
If Caribbean businesses want better returns, it starts with changing the equation:
- Validate your creative first
- Understand what resonates and why
- Then — and only then — invest in amplification
Because right now, we’re spending to cover up weak strategy — not to scale strong results.
📊 Interesting Stats:
- High campaign spend without organic validation leads to waste and low ROI — especially in systems without content testing infrastructure (Deloitte Digital).
- Marketing agency turnover is over 30%, contributing to lost brand knowledge and reactive campaigns (WorkWithOpal).
🧠 Round 3: Creative Is the Reach — So Why Is the Content So Safe?
🎤 Gary’s Take:
“Creative is the variable of success in modern marketing. The algorithm is a reflection of audience reaction — not something you hack. If your content doesn’t move people, it won’t move numbers.”
🤜🏾 My Take:
In the Caribbean, most brand content looks like a PowerPoint presentation wearing makeup.
It’s overproduced. It’s generic. It’s “safe.”
It’s trying to avoid criticism instead of trying to connect.
And that’s the root of the problem:
We’re creating content to check boxes — not to move people.
To impress the boardroom — not to speak to the audience.
You see it every day:
- A slick video with no soul
- A skit that follows a TikTok trend but has zero relevance to the brand
- A Canva post that lists five generic “tips” nobody asked for
And when none of it lands organically? We boost it.
We use paid ads to mask the fact that nobody cared.
Because the content wasn’t built to reach — it was built to avoid risk.
What Caribbean marketers need to understand is this:
Creative is the distribution.
If people don’t stop scrolling, don’t comment, don’t share — your content is invisible.
No ad spend can save that.
And here’s the irony — we have amazing stories, culture, and context.
But instead of using that to create distinctive brand content, we copy what’s trending globally and end up with work that’s invisible locally.
You can’t build long-term digital equity off of TikTok trends.
You can’t scale trust from jokes alone.
You need substance. You need storytelling. You need original thought.
And you need to stop being scared of being real.
📊 Interesting Stats:
- 75% of users say they judge a brand’s credibility based on its creative content and storytelling consistency (Nielsen)
- Over 60% of global digital marketers cite “fear of failure” and “brand risk-aversion” as key blockers to producing bold, effective content (HubSpot Marketing Trends Report 2024)
🧠 Round 4: The Education Gap — Why Your Marketers Can’t Keep Up
🎤 Gary’s Take:
“You’re not lazy. You’re just educated by a machine that stopped evolving. You’ve been taught marketing from people who never did it in this era. That’s why the ideas don’t work.”
🤜🏾 My Take:
This one hit hard — because it’s the part nobody wants to admit.
Formal marketing education in the Caribbean simply can’t keep pace with how fast this landscape is evolving.
Tertiary institutions are still focused on traditional business and marketing theory — but those fundamentals haven’t been retooled for today’s world.
And when digital marketing is introduced, it’s usually surface-level or outdated.
When they do try to bridge the gap, it’s often through:
- One-off workshops or certifications
- Priced far out of reach for the average person
- Built on assumptions that businesses are ready to implement the training
But here’s the reality:
Even when companies invest in these programs, they haven’t upgraded their systems, tools, or mindset — so the knowledge goes nowhere.
Employees come back to broken funnels, no websites, no CRM systems, and no authority to implement change.
Low enrollment leads to courses getting cancelled.
Upskilling becomes another vanity metric — a certificate to post on LinkedIn with no change in execution.
And that’s why marketing in the region continues to feel stuck.
That’s why I’ve been running my own workshops — free and paid — to fill the gap.
And that’s why I create content at scale.
Because I know that if I can’t reach them in a classroom, I need to reach them on the platforms they use every day.
Plant seeds. Spark new thinking. Show what’s possible — even if it’s just from my own capacity as a solo operator.
But we’re long past the point of waiting for the system to fix itself.
We have to rebuild it.
From the ground up.
📊 Interesting Stats:
- 47% of marketing professionals worldwide say their university education did not prepare them for the current digital landscape (LinkedIn Learning)
- Global search interest in “self-taught marketing” and “how to become a content creator” has more than doubled since 2021 (Google Trends)
🧠 Round 5: The Broken Funnel — No Website, No CRM, No Sale
🎤 Gary’s Take:
“We have this insane moment in time — where you can build everything around content. But if there’s no infrastructure behind it, if there’s no funnel, if you don’t understand where you’re pushing people, you’re just playing.”
🤜🏾 My Take:
This right here is the root of why most Caribbean marketing efforts never translate to revenue.
We’re spending money on content without building the systems that make content work.
We’re generating attention — but have nowhere to send it.
Let’s look at the funnel.
- No website? That’s strike one.
- Website but no e-commerce functionality? Strike two.
- No CRM? No lead capture? No segmentation?
You’re out before the game even starts.
Most businesses in the Caribbean operate on static websites — a few pages, maybe a product list, and a “Contact Us” form.
No blog. No search strategy. No sales pages. No automation. No analytics.
And yet… they expect social media content to “drive sales.”
Worse, marketers are expected to report on ROI — when the infrastructure to even measure it doesn’t exist.
No attribution. No sales tracking. Just some boosted posts, a few likes, and maybe a PDF report from Hootsuite.
This is why marketers in the region are burnt out.
They’re not just underpaid — they’re set up to fail.
Because without a digital foundation to build on, all marketing becomes a hamster wheel of content with no conversion.
Here’s the kicker:
We actually do have infrastructure in the region.
- E-commerce platforms? Check.
- Payment gateways like PowerTranz, WiPay, SurePay, First Atlantic? Check.
- Access to tools like Shopify, Wix, WordPress, and regional alternatives? Check.
- CRM options like HubSpot, Zoho, or Mailchimp? All available.
So it’s not a tech issue.
It’s an execution issue.
We’re not using what we already have.
And because of that, everything we do online stays at the surface — no depth, no systems, no scale.
📊 Interesting Stats:
- 70% of digital transformation efforts globally fail due to lack of internal alignment, infrastructure, and leadership buy-in (McKinsey)
- Only 12% of Caribbean businesses report having functional e-commerce platforms with payment integration (Caribbean Export Development Agency)
🧠 Round 6: Overproduced, Underperforming — Why “Polished” Content Falls Flat
🎤 Gary’s Take:
“People think they’re producing great content because it looks good. But it’s not about polish. It’s about connection. That’s what scales — not cinematography.”
🤜🏾 My Take:
This one stings — because we see it every day across the Caribbean.
High production value, beautiful visuals… and absolutely no traction (unless boosted).
Businesses are spending real money — hiring professional videographers, photographers, and editors — to create polished brand content.
But the content isn’t designed to connect.
It’s designed to impress a room of executives, not resonate with real people online.
And when that $1,500 shoot doesn’t perform?
They boost it.
They throw more money at the media spend to make up for a message that never landed in the first place.
Here’s what most people don’t understand:
Daily content is the marketing now.
Your feed is your brand.
Your stories are your sales team.
And if you’re only showing up during “campaign season,” you’ve already lost.
Yes, campaigns have their place — but in 2025 and beyond, marketing is an always-on engine.
You should be teasing products, sharing customer journeys, showing behind the scenes, educating your audience — every day.
That’s how you build familiarity, trust, and conversion paths over time.
But instead, most brands treat content like a “get rich quick” scheme.
They want one viral post to drive a quarter’s worth of sales — instead of building consistent IP that compounds in value.
And to make it worse, they’re not creating content they can reuse.
Because it’s all trend-based, skit-based, or moment-specific.
So instead of building a content library they can repost, redistribute, or repurpose — they’re starting from scratch every week.
It’s exhausting.
It’s expensive.
And it’s unsustainable.
What they need is strategy.
Content that educates, sells, and builds community over time.
Creative that feels native to the platforms — but also anchored in brand DNA.
But right now?
They’re just spending to hide bad strategy behind glossy footage.
📊 Interesting Stats:
- 67% of consumers say authenticity is more important than production quality when deciding whether to engage with a brand’s content (Stackla / Tint)
- Only 5% of marketers say their organization has a robust content repurposing system in place (Content Marketing Institute)
Case Study: Nothing Phone’s Pre‑Launch Ecosystem
- Pre‑Launch Teasing & Anticipation: Instead of relying solely on traditional launch campaigns, Nothing builds consistent buzz by teasing upcoming devices (like the Phone 2A Plus) with carefully timed visuals and strategic content releases.
(Latterly case study) - Community Co‑Creation for Engagement: Their “Community Edition” campaign invites real fans to contribute design ideas—over 900 submissions fed into a glow-in-the-dark phone release that created ownership and excitement.
(The Verge) - Mindful Guerilla Campaigns: With Flipkart, Nothing ran a fresh “Don’t Buy Me” campaign—disrupting expectations with counter-intuitive messaging about mindful phone usage that was more meaningful than promotional.
(Campaign Brief Asia)
🧠 Round 8: The Two-Platform Trap — And Why There’s No Scale
🎤 Gary’s Take:
“You can’t build a business on rented land. If your whole brand lives on two platforms, you don’t have a business — you have a vulnerability.”
🤜🏾 My Take:
This is the most dangerous illusion of digital success in the Caribbean right now.
Most businesses are only on Facebook and Instagram — and now maybe TikTok.
That’s it.
No website.
No YouTube.
No email list.
No CRM.
No owned ecosystem.
And if any one of those platforms changes the algorithm, gets restricted in your country, or disappears tomorrow — you’re done.
This is what we mean when we say brands are not scalable.
Not because they don’t have great products.
But because they’ve built everything on a foundation they don’t control.
You can’t build long-term ROI in a space where you don’t own the customer journey.
Worse, they’re doing all of this without even leveraging the search engine visibility of platforms like YouTube, Pinterest, LinkedIn, or even Instagram’s new ability to show up in Google.
Let’s be real:
If you’re creating only trending content, you’re invisible in search.
You can’t be discovered.
You can’t be referenced.
You can’t be cited in AI tools or pulled up in Google results.
That’s why content strategy needs to evolve.
But we don’t even have SEO specialists on marketing teams.
Why?
Because in most companies, SEO is just a line item thrown into the job description of the “social media manager” — who may not even have a website to optimize.
It’s laughable… if it weren’t so damaging.
So let’s ask the uncomfortable question:
If you removed Facebook and Instagram tomorrow — would your business still exist online?
For most brands, the answer is a hard no.
📊 Interesting Stats:
- 63% of all shopping journeys begin online — and 49% of those start with a search engine, not social media (Think With Google)
- 88% of marketers agree that having a multichannel strategy is critical for long-term success — yet only 31% say they actively use more than two channels to reach their audience (HubSpot)
🔍 AI Search Drives Sales, Not Just Clicks
This recent chart from Neil Patel Digital (June 2025) says it all.
Even though AI search only accounts for a fraction of the traffic, it drives an almost equal percentage of sales — especially in B2B. That means people coming from tools like ChatGPT or Perplexity aren’t just browsing — they’re ready to buy.
This isn’t about vanity metrics or reach.
This is about qualified traffic with intent — and businesses who don’t have content designed to be found in search (traditional or AI) are leaving serious money on the table.
This is why you need SEO, searchable content, and platforms like YouTube and your website working 24/7.
Because sales don’t happen in your skits. They happen when people are searching for solutions — and find you.
Round 9: Chicken & Egg — Who’s Supposed to Fix This?
🎤 Gary’s Take:
“Companies keep saying, ‘But who’s going to make all this content?’ My question is — who’s running your business?”
Gary challenged the entire premise that marketing should still be treated like a silo or outsourced afterthought. In his view, brands need to stop acting confused about who will execute and start treating content as core to business survival. You don’t need 15 people — you need clarity, commitment, and consistency.
🤜🏾 My Take:
This is exactly what I’m seeing on the ground. When I show people everything I do for my brand — my workshops, my website, my podcast, my video content, my newsletter, my SEO strategy — I always hear the same thing:
“Our business doesn’t have the budget to do all that.”
And I always respond:
“I am one person. You have a team. What’s really the excuse?”
Here’s the truth: when businesses ask “Who’s going to do it?” what they’re really saying is “We haven’t built our teams for this reality.”
And when I ask, “What is your internal marketing team doing?”, they often admit that no one on their team actually has the skills needed to execute the plans we lay out. So now we’re in a full-blown chicken and egg scenario: the work doesn’t get done because the skills aren’t there, and the skills never develop because the work never gets done, which is why it all gets outsourced, leading to double spending of marketing budget. Paying for the internal and external resources.
At this point, Caribbean brands will either sink or swim.
You must build your own digital ecosystem around your business:
- Digital + traditional content (radio, TV, podcast, blog, YouTube, social)
- Thought leadership from your team
- E-commerce, lead funnels, automations
- Behind-the-scenes storytelling, customer education
- Real-world engagement through events and tradeshows
Consumers are evolving. They want convenience and experiences. They want to shop online and/or show up at your store for a deeper connection. They want you to know what they want — and they expect you to keep showing up with value before you ever pitch a sale.
In the Caribbean, we say we offer both — but the reality is most businesses offer neither.
And then they wonder why the marketing team can’t show results.
📊 Interesting Stats:
According to a 2024 global survey by HubSpot,
75% of marketing leaders say they are investing in content operations and internal team building in 2025, not just external campaigns.
In contrast, most Caribbean businesses still rely on external agencies or one-man marketing teams — with no content strategy, no in-house training, and no sustainable workflow. This gap in execution is exactly what’s killing ROI and burning out marketers.
Round 10: Building a Brand in 2025+
🎤 Gary’s Take:
“If you’re not documenting, storytelling, and educating every day, you’re not building a brand — you’re just running ads.”
Gary emphasized that daily content — not just campaigns — is the heartbeat of modern marketing. From founder-led storytelling to behind-the-scenes videos, you need to be present. You need to show up. Because in 2025 and beyond, brand awareness, trust, and conversions are built in real time — not in quarterly bursts.
🤜🏾 My Take:
Caribbean businesses still treat content like a one-off event.
They’re stuck in campaign mode — budgeting for bursts of content that are overproduced, expensive, and require boosting to even get views.
Meanwhile, brands like Nothing Technology have shown us what always-on marketing looks like. Their CEO Carl Pei reacts to product reviews on YouTube. They tease new features in real time. They involve their community before launch. They make marketing feel like a conversation — not a broadcast. And it works.
We have creators. We have platforms. We even have tools. But most businesses here don’t have:
- A YouTube channel (despite YouTube being one of the top search engines)
- A content library of searchable or evergreen content
- A distribution system outside of Instagram or TikTok
- An understanding of content as IP and marketing assets that compound over time
Instead, we treat content like a get-rich-quick scheme — chasing the next trend, blowing the budget on one flashy video, and expecting overnight success. And when the return doesn’t come, we say “marketing doesn’t work.”
No — that marketing doesn’t work.
📊 Interesting Stats:
A June 2025 study by Neil Patel Digital revealed that AI search now drives fewer clicks but significantly more qualified sales.
For example:
- B2C Sales: 11.4% from AI Search vs 21.5% from Traditional — despite AI getting just 0.49% of the traffic.
- B2B Sales: 9.7% from AI Search vs 11.6% from Traditional — again, with far less traffic.
This means content that shows up in AI tools — like ChatGPT, Perplexity, and Gemini — is driving high-intent sales, even if it doesn’t get massive clicks.
And yet, most Caribbean businesses don’t create searchable content, don’t invest in SEO, and don’t repurpose.
They chase trends… and miss the traffic and the sales.
Final Round: We’ve Been Exposed — Now What?
The Gary Vee keynote didn’t say anything revolutionary —
It confirmed what many of us in the Caribbean already knew deep down.
Marketing, as it stands in the region, is broken.
Agencies are delivering content without context.
Businesses are spending without strategy.
Marketers are burning out without systems.
And no one can prove the work is working — because nothing is set up to measure it.
What Gary did was put a global spotlight on the dysfunction we’ve normalized.
And now… there’s no hiding.
🤜🏾 My Final Take:
I’ve been in this industry for a decade — not just watching trends, but building businesses, doing the work, and teaching from results.
Every backend dashboard I show in a workshop is mine. Every strategy I teach is tested on myself first.
Because I had to learn this the hard way — as a practitioner, not a theorist.
That’s why I’m so loud about fixing this. Because we have options.
We might not have the full tech stack of North America or Asia…
But we do have:
- Access to e-commerce platforms
- Local & international payment gateways
- YouTube, Instagram, and search visibility
- CRM and email tools
- Platforms to build and distribute our content
- Communities ready to be engaged
What we’re lacking is execution.
Vision.
Accountability.
And a willingness to own our brand ecosystem instead of renting attention.
As we head into 2026, the brands that win will be the ones who:
- Build in-house capabilities
- Integrate digital and traditional
- Shift from campaign thinking to ecosystem thinking
- Create content with purpose, not just presence
- Learn, test, and scale based on real-time data
No one’s coming to save us.
We either evolve — or we disappear.
That concludes my sparring session with one of my mentors from afar and one of the best in the game, Gary Vaynerchuk.