The $1B Stablecoin Signal + Why VCs Are Betting Big on AI Services
Inside the New Rules of Stablecoin Infrastructure, AI Services, and B2B Creator Marketing
I spent a day this week at Eric Newcomer's Breaking the Bank event and Stripe's $1 billion acquisition of Bridge that closed in February was still the talk of the event. It was not just another fintech exit—it was a declaration that stablecoins have moved from crypto curiosity to infrastructure necessity. This week, I watched VCs who've historically avoided crypto suddenly ask detailed questions about payment rails and cross-border settlements and try to get into hot deals on the spot.
The message is clear: stablecoins are eating traditional banking infrastructure, one use case at a time.
The Stablecoin Infrastructure Gold Rush
What made Bridge worth $1 billion? They built the picks and shovels for stablecoin adoption—APIs that let any company integrate dollar-backed digital currencies without touching the underlying blockchain complexity. Stripe's making the acquisition sent the bat signal to everyone that this is going to be a thing.
Three insights from Breaking the Bank that signal where this market is heading:
1. Payment rails are the new battleground. Traditional wire transfers cost $25-50 and take 1-3 days. Chase Bank actually charges $15 for incoming wires if you are not rich, and Western Union still has a $3.19 billion market cap. Stablecoin transfers cost pennies and settle in minutes. Every payment company is now building or acquiring stablecoin capabilities.
2. Enterprise adoption is accelerating faster than consumer adoption. While retail users debate crypto volatility, CFOs are quietly moving treasury operations to stablecoin rails for international payments. One fintech founder told me their enterprise clients save 40% on cross-border transactions and this unlocks a global business opportunity for them. You can instantly think about global payments and the obvious use cases are how SpaceX sells Starlink and how Scale AI pays international workers.
3. The infrastructure layer is where the money is. Bridge, Circle, and others aren't betting on specific stablecoins—they're building the infrastructure that makes any stablecoin useful for businesses.
The takeaway for founders: if your business touches international payments, treasury management, or B2B transactions, stablecoin integration isn't a "nice to have" anymore—it's table stakes.
Also, I think in general, businesses will all launch coins in the next decade. One of my friends launched one in the 2017/2018 era, and it still sits at a $370M market cap, and he and his team still own a majority of it, so this is nothing new, but I think it will become an even more normalized thing as stablecoins develop.
The $60 Trillion AI Services Opportunity (And Only 3 Ways to Win)
Matt Harris from Bain Capital delivered the most eye-opening presentation I've seen on AI's real market opportunity.
His thesis: we're not just automating software—we're replacing entire service industries. This is how VCs are thinking about their opportunities now the services industry is the market opportunity not the software, payments, lending, or other markets.
The numbers are staggering. While software markets measure in billions, the services they're targeting measure in trillions:
Legal services: $350B annually (vs. $100B in legal software)
Accounting/tax services: $ 500 B+ annually
Insurance services: $1.3T annually
Harris identified only three viable paths to build in this market:
Path 1: The Vertical AI Native Start fresh with AI-first workflows targeting specific industries. Filed's $17M raise (more on this below) exemplifies this approach—they're not improving existing tax software, they're replacing the entire tax preparation workflow with AI.
Path 2: The Service-to-Software Transition Buy existing service businesses and gradually replace human labor with AI. Harris calls this "the empire strikes back" model, where traditional firms use AI to dramatically increase margins while maintaining client relationships. General Catalyst has an entire team devoted to this new approach, and Thrive announced they are doing the same.
Path 3: The Infrastructure Play. Build the foundational tools that enable others to automate services. Think Anthropic's Claude, which just released another model today for professional services or specialized AI models for specific industries.
The key insight: unlike traditional software, these businesses require deep domain expertise from day one. The most successful teams combine technical AI capabilities with decades of industry experience.
Filed Raises $17M: Another Shot at TurboTax
Speaking of AI tax automation, Filed just raised $17.2M from Northzone to tackle the same market we're building in at ModernTax. Fortunately, we feel it is a $60 billion market opportunity by 2034.
Their approach: AI that reads tax documents, applies firm-specific strategies, and integrates directly with existing software.
What's interesting about Filed's positioning is their focus on the labor shortage crisis. Black Ore is even more well-funded and taking the same approach and Aiwyn who recently raised $100M+ from KKR acquired Taxa which was building a AI-first tax preparation software from the ground up.
With CPAs retiring faster than new graduates entering the field, tax firms are desperate for solutions that multiply human productivity rather than replace it entirely.
The competitive landscape in AI tax is heating up:
TurboTax Live/Intuit: Defending with incremental AI features
Filed: Building AI-native workflows for professionals
ModernTax: Focusing on tax intelligence and verification infrastructure for transaction-focused companies serving SMBs and individuals
Numerous startups: Targeting different segments from individual filers to enterprise compliance
The market opportunity is massive—Americans spend $546 billion annually on tax compliance—but the winners will be determined by execution speed and deep understanding of tax professional workflows.
Speaking of ModernTax, we're helping financial institutions reduce tax verification times from weeks to minutes while improving accuracy. If you're in lending, wealth management, or benefits administration, let's connect to discuss how tax intelligence can accelerate your workflows.
Creator Economy Insights: What Gamma, Intercom, and Replit Learned
I attended an AI creator panel featuring marketing leaders from Gamma, Intercom, and Replit. Here are the tactical insights that matter for B2B companies:
The Always-On Strategy Works Gamma attributes 25% of their 15 M+ users to creator-driven content. Their secret: working with 5-10 long-term creators rather than spreading budget across hundreds of one-off campaigns. The compound effect of consistent messaging from trusted voices beats viral moments.
Platform Mix is Shifting. LinkedIn is becoming the primary B2B creator platform, with surprising success on TikTok for technical products. Instagram and Twitter remain important for reach, but conversion happens on LinkedIn, no matter how much you may hate it, it is where business buyers are.
Authenticity > Scale. The most successful partnerships come from creators who genuinely use and understand the product. One creator's authentic MongoDB post generated 1.5M impressions and drove 100 K+ visitors to their GitHub repo—because it felt like genuine developer content, not an ad.
The ROI Challenge: Every marketing leader struggles with attribution. The solution: set clear campaign goals (brand awareness vs. conversion) and measure accordingly. Track first-party metrics (sign-ups, demos) alongside vanity metrics (impressions, engagement).
The bottom line: creator partnerships work for B2B, but only with authentic voices, long-term relationships, and realistic expectations about attribution.
What I'm Watching
Treasury management platforms are building stablecoin integration capabilities
AI service companies targeting "despised" industries like insurance claims processing
Creator-in-residence programs at B2B companies (following Deepgram's model) – fellow substacker Ben Lang, who runs next play recently joined Cursor
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Four Insights Finance Leader Dinner Series
I'm hosting three exclusive dinners for finance leaders this summer:
June 6: San Francisco
July 15: San Francisco
September 4: New York City
These intimate gatherings (15-20 attendees) bring together founders, CFOs, and finance tech leaders for meaningful conversations over exceptional dining experiences.
Interested in attending or sponsoring? Email me directly for details at matt@stretchfour.co
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Until next week,
Matt