95% of AI projects fail. Here’s why yours won’t.
Fix your AI strategy before you burn another million on tools
Your competitor just announced their “AI transformation.” Your board is asking about your AI roadmap. And every vendor pitch starts with “our AI-powered solution.”
But here’s what nobody’s saying: 95% of organizations see zero return on AI investments, according to MIT’s latest study. And 42% of companies have already abandoned most of their AI initiatives this year.
This week, I’m showing you exactly why most AI projects crash—and the structural shifts that separate winners from the 95% who are just burning cash.
Today’s agenda:
📉 Why 95% of organizations see zero return on AI investments
💎 Asset tokenization is eating financial services (and what it means for you)
🚀 The AI marketing stack that’s actually working for fintech
💼 Briefly: Workslop costs, energy plays, and VC’s AI obsession
⏱️ Up & coming: Tokenization hits $24B—and it’s just getting started
Your AI strategy is failing because your org chart is broken
The problem isn’t your AI tools. It’s not your data quality. And it’s definitely not a lack of budget.
The problem is structural. You’re trying to bolt AI onto an organization designed for predictable, repeatable, autonomous processes, not creative, dynamic, complementary predictive work.
In a recent deep-dive analysis I conducted on why enterprise AI projects fail, I found the same pattern repeating across industries: disconnected processes working in silos. Product teams are stuck in waterfall processes. Infrastructure teams scaling bandwidth, not compute and memory (making infinite data accessible). Data teams focused on legacy structures and systems. Meanwhile, compliance teams are slowing everything down with review processes that can’t keep up with hyperscaling productivity.
Meanwhile, 95% of AI projects fail to deliver any measurable return—according to MIT’s recent study on enterprise AI adoption.
🎯 Here’s what actually works:
Purpose-built AI organizations. Not traditional companies trying to retrofit AI into legacy processes, but teams specifically designed to deliver AI outcomes from the ground up.
The winning playbook:
Flat hierarchies that emphasize agility over traditional reporting structures
Strategic Execution Teams (SETs) that embed AI across strategy, execution, and tactics—not just in a single department
Outcome focus over tool fetishism—measure business results, not model performance metrics
User buy-in first—successful implementations start with change management, not technology deployment
Before you fund another AI initiative, ask: Is your organization actually structured to execute it? Or are you just creating another failed project for the 95% pile?
📊 Read a complete analysis of enterprise AI project failures
Robinhood’s CEO says tokenization will “eat the entire financial system”
While most fintech executives are still trying to understand blockchain, $24 billion in real-world assets have already been tokenized across 194 issuers in 2025, according to a comprehensive market report from RedStone, Gauntlet and RWA.xyz.
And the pace is accelerating.
Robinhood CEO Vlad Tenev recently declared: “Tokenization is like a freight train... it’s going to eat the entire financial system.” His company launched 200+ tokenized US stocks for European customers this year.
Next up? Real estate.
It’s not just Robinhood making bold moves. Figure holds 70%+ market share in Real World Asset tokenization, with over $13 billion in HELOC originations already on blockchain—and they just achieved the first S&P AAA-rated blockchain-native securitization.
💡 What this means:
24/7 global trading. Assets that used to be locked into 9:30am-4pm EST trading windows can now move around the clock.
Fractional ownership unlocked. High-value assets—private companies, real estate, credit instruments—become accessible to smaller investors through tokenization.
Faster settlement, lower costs. Blockchain eliminates intermediaries and reduces friction in the transaction process.
Programmable compliance. Smart contracts automate regulatory requirements and distributions.
The question isn’t whether tokenization will reshape financial services. It’s whether you’ll be positioned to capitalize on the shift—or get disrupted by it.
Tenev predicts most major markets will have tokenization frameworks within 5 years. Figure’s addressable market in credit tokenization alone exceeds $2 trillion.
The AI tools actually moving the needle for B2B fintech
Let’s cut through the AI marketing hype and talk about what’s actually working in fintech go-to-market right now.
I’ve been testing AI-powered sales and marketing tools with clients over the past six months. Some delivered. Most didn’t. Here’s what made the cut.
✅ The AI stack I recommend to every founder:
For outbound at scale:
Comet Browser - Research, prospecting, and a companion to my Close CRM sales activity and management
Claude or ChatGPT Projects - Copywriting and strategic planning
v0 - Quick app development, custom calculators, and instant pitch decks
For marketing automation:
Vibe Marketing approach—AI handles campaign execution (visuals, copy, variants) while humans provide strategy and emotional intelligence
Predictive analytics tools that analyze customer behavior to prioritize leads based on actual buying signals, not vanity metrics
What’s real vs. what’s pie in the sky:
Real and working now:
Automated prospecting with accurate lead scoring
Personalized email sequences at scale that don’t feel robotic
Real-time campaign optimization based on engagement data
Compliance-aware content generation for regulated industries
Still oversold:
“AI will replace your sales team”—human relationship building is still crucial in high-trust B2B sales
“Set and forget” automation—strategy and oversight are still required
“Instant results”—building trust in fintech still takes time, AI just accelerates it
The key insight: AI doesn’t replace your GTM strategy. It amplifies the one you already have. If your fundamentals are broken, AI will just help you fail faster at scale.
📆 Schedule a Discovery Call to discuss your AI GTM strategy
Briefly
📊 AI-generated “workslop” is destroying productivity. More than half of white-collar workers admitted to producing AI-generated content that appears productive but lacks substance. Harvard and Stanford researchers found this costs large organizations millions in lost productivity annually.
⚡ Nuclear energy is surging as the only viable solution to AI data center demand. While traditional energy stocks surge, the real opportunity lies in small modular reactors (SMRs). Training GPT-4 alone requires 30 megawatts of continuous power—enough to supply 20,000 homes. Major tech companies like Google and Amazon are making massive SMR investments as AI data centers could grow more than thirtyfold by 2035.
💰 AI venture capital investment hit record highs in 2025. Venture funding for AI startups reached unprecedented levels, with some AI engineers commanding compensation packages exceeding traditional levels. Industry experts debate whether this represents a sustainable market or another tech bubble.
📱 “Vibe marketing” is transforming B2B campaigns. The approach combines AI efficiency with human emotional intelligence, reducing campaign creation time from weeks to hours and enabling small teams to compete with large marketing departments through AI-powered personalization. Marketing teams are reporting significant efficiency gains.
Up & coming: The $5 trillion tokenization wave
$24 billion in real-world assets have been tokenized across 194 issuers in 2025. That includes $7.4 billion in tokenized Treasury funds alone—up 80% year-to-date.
Real estate tokenization has reached approximately $20 billion, with projections soaring to $1.5 trillion in the coming years.
The global tokenization market is projected to reach $5.25 trillion by 2029—a 43.36% compound annual growth rate.
This isn’t a future trend. It’s happening now. And every major financial institution is scrambling to figure out their positioning before the wave crashes over traditional infrastructure.
Read a complete tokenization market analysis →
We’re your personal Chief of Staff, keeping you strategically informed
Bill Rice | Founder | Strategic Advisor to Fintech CEOs