Coach Kyle

Private Market Stock Spotlight- STRIPE INC. The New King Of Online Payments.

Newsletter LibraryPrivate marketsSpecial Edition

G.L.A. Invest Research and Coach Kyle | May 26, 2026 | Not Financial Advice or a Solicitation.

View original edition ↗Reader disclosures
Stripe: Payments and AI Commerce Research — original newsletter cover
Original artwork published with this archived edition.

Stripe Inc. “The New King of Online Payments and Online Commerce

Investment Research Report

G.L.A. Invest Research and Coach Kyle | May 26, 2026 |Not Financial Advice or a Solicitation.

Original illustration from this archived newsletter

Company Snapshot

Founded

2010 (San Francisco, CA / Dublin, Ireland)

Stage

Late-stage private / Pre-IPO

Latest Valuation

$159 billion (February 2026 tender offer)

Total Raised

~$9.4 billion

CEO

Patrick Collison (co-founder)

President

John Collison (co-founder, interviewed at Stripe Sessions)

Lead Investors

Sequoia Capital, Andreessen Horowitz, Founders Fund, Thrive Capital, Coatue

2025 Revenue (est.)

~$6.9 billion net (+36% YoY)

2025 TPV

$1.9 trillion (+34% YoY)

2025 EBITDA (est.)

~$1.2 billion

Profitability

Profitable — confirmed 2024 return to profitability; “robustly profitable” in 2025

Customers

5M+ businesses; half of the Fortune 100

Countries

46 (payments); 101 (stablecoin accounts); 102 (tax)

Original illustration from this archived newsletter

Investment Thesis

Stripe is the defining financial infrastructure company of the internet era — and it is now positioning itself as the defining financial infrastructure company of the AI era. That repositioning is not marketing language; it is happening in real time.

At Stripe Sessions in April/May 2026, President John Collison laid out a vision where AI agents become economic actors — researching products, selecting vendors, and completing purchases on behalf of humans, without a human ever touching a checkout form. Stripe already has live integrations inside Google Gemini, Microsoft Copilot, and OpenAI’s ChatGPT enabling exactly this. The company is not pitching a future — it is building the plumbing for a fundamental shift in how commerce works.

At $159 billion, Stripe is expensive. But the framing matters. This is a company processing $1.9 trillion in annual payment volume — equivalent to 1.6% of global GDP — growing at 34% YoY, generating ~$1.2B in EBITDA, and actively expanding into every layer of financial infrastructure: billing, banking, stablecoins, fraud detection, corporate cards, lending, and now agentic commerce. The number of comparable businesses in history is very small. Coach Kyle’s 2 Cents- Trillion Dollar Company in the Making!

“The economy is really replatforming around AI and businesses are doing totally different things.”
— John Collison, President, Stripe (Stripe Sessions, 2026)

Original illustration from this archived newsletter

The key question for pre-IPO investors is not whether Stripe is a great business — it clearly is. The question is when will they IPO? What the path looks like from $159B to an eventual Multi Trillion Dollar Company, and how big will the online commerce game will become with AI powering everything.

Financial Profile

Revenue & Volume

Year

Net Revenue

YoY Growth

Total Payment Volume

YoY Growth

2023

$3.82B

—

~$1.0T

—

2024

$5.1B

+34%

$1.4T

+38%

2025

~$6.9B

+36%

$1.9T

+34%

Sacra estimates 2025 net revenue of ~$6.9B, with EBITDA of ~$1.2B. The company returned to profitability in 2024 after a $1.2B pre-tax loss in 2023, and confirmed it remained “robustly profitable” in 2025 — enabling it to ship 350+ product updates and pursue strategic acquisitions (Metronome for ~$1B, Privy for crypto wallets).

Original illustration from this archived newsletter

Unit Economics

  • Core take-rate: ~0.40% net after interchange, network, and partner costs (on ~3% gross fees)

  • Revenue & Finance Automation Suite: On track for $1B annual run rate in 2026 (up from $500M in Feb 2025 — doubled in one year)

  • Stripe Billing: 300,000+ companies; managing nearly 200M active subscriptions

  • Stablecoin TPV: ~$400B in 2025; ~60% B2B

Scale Milestones

  • Black Friday–Cyber Monday 2025: 578M transactions, $40B+ in 4 days; $10B+ on Cyber Monday alone

  • Half of the Fortune 100 uses Stripe

  • 5M+ direct and platform businesses served

Original illustration from this archived newsletter

The AI Commerce Thesis — In John Collison’s Own Words

The most important strategic insight from the Stripe Sessions transcript is John Collison’s articulation of how AI is restructuring commerce at a fundamental level:

1. Consumers are transacting inside AI apps

“Customers are now researching products within AI apps… and actually completing the transaction within the AI apps.”

Previously, consumers Googled, visited websites, and checked out. Now the discovery and transaction are collapsing into the same AI surface. Stripe is the payment layer for all of it.

2. Businesses are selling to coding agents

“Coding agents are doing so much work, we can delegate the work to the coding agents… increasingly tech companies are selling to coding agents directly.”

A software company like Cloudflare or Stripe itself previously sold to a human buyer. Now autonomous coding agents (Claude Code, Cursor, Codex) are procuring services — buying domains, spin up servers, subscribing to APIs — without human involvement. Stripe is building the identity and payment rails for this.

Original illustration from this archived newsletter

3. The trust curve — from research to delegation
Collison laid out a practical trust ladder for AI commerce adoption:

  • Today: AI does research; human confirms

  • Near-term: AI makes small, low-risk purchases autonomously (e.g., finding and buying a domain name)

  • Medium-term: AI makes larger purchases with pre-authorized budgets

  • Long-term: Full AI economic actors — agents managing supplier relationships, making procurement decisions, processing payments

    “People are already starting a little bit, and a huge amount of what we announced today is those little decisions people are delegating.”

    This is not a theoretical framework. Best Buy, Kate Spade, and dozens of major brands have already signed up to be part of Stripe’s agentic commerce network.

The AI Product Stack

1. Agentic Commerce Protocol

Co-developed with OpenAI. Live inside ChatGPT, Microsoft Copilot, and now Google Gemini (announced at Stripe Sessions). Handles:

  • Agent identity — verifying who the agent is

  • Payment authorization — the user authorizes once; the agent executes

  • Settlement — money moves through Stripe’s network

US ChatGPT users can now purchase from Etsy merchants in-chat. Copilot users can buy from Urban Outfitters and Anthropologie. Google Gemini is the newest and largest addition to this network. As Collison put it: “It’s never been the case in technology when you get a way more convenient way of working for consumers that they pick the less convenient one. It has to be the future.”

Original illustration from this archived newsletter

2. Link — 250 Million Users

Stripe’s consumer wallet. Saves payment details across all Stripe-powered checkout experiences — the consumer equivalent of a network moat. Now being opened to AI agents: “We have opened our Link consumer digital wallet to AI agents, allowing users to let the agent make payments on their behalf.” 250M users make Link a significant consumer identity and payment network in its own right.

3. Metronome — Usage-Based Billing ($1B acquisition)

Acquired December 2025 / closed January 2026 for ~$1B. The leading usage-based billing infrastructure, used by OpenAI, Anthropic, Databricks, Confluent, and NVIDIA.

As Patrick Collison stated: “Metered pricing is the native business model for the AI era… the associated shift in how businesses generate revenue will be as big as the advent of SaaS. It may even turn out to be considerably bigger.”

The logic: every AI product charges on a per-token/per-API-call basis. Metronome handles the complex metering, analytics, and billing infrastructure that makes that possible. Stripe now owns this layer.

4. Streaming Payments / Per-Token Billing

“All of the AI products that anyone has need to be charged on a per usage basis — there is just no other way that makes sense.”

Original illustration from this archived newsletter

Collison introduced “streaming payments” — real-time per-token billing as AI inference happens. Traditional SaaS charged per seat/month. AI charges by the millisecond of compute. Stripe is building the infrastructure for this new billing paradigm, positioning itself as the financial backbone of the entire AI software economy.

5. Stablecoins — Bridge + Temple Blockchain

Stripe acquired Bridge (stablecoin infrastructure) and has incubated Temple, a purpose-built payments blockchain. Stablecoin payment volume on Stripe’s network hit $400B in 2025(doubled YoY). 60% is estimated B2B.

The use case Collison described: micropayments for AI inference. Traditional credit card rails charge ~$0.20+ per transaction — unworkable for per-token billing at fractional cent values. Stablecoins via blockchain enable true micropayments without that floor.

“Micropayments via stablecoins makes total sense… it’s very much about real time.”

Stripe also acquired Privy (July 2025), powering 110M+ programmable crypto wallets, and offers stablecoin financial accounts in 101 countries.

Original illustration from this archived newsletter

6. Stripe Radar — AI Fraud Prevention

“Stripe Radar in the past month alone blocked more than 3 million attempted thefts just from the top 8 AI companies we work with.”

AI companies are high-value targets for fraud — stolen inference, free trial abuse, credential stuffing. Stripe’s network-level fraud detection (trained across trillions of transactions) is one of the hardest advantages for any single merchant to replicate. Collison: “If you have things of value on the shelf, no matter what kind of shop you’re running, you’re going to have shrinkage issues.”

7. Payments Foundation Model

Stripe’s proprietary AI model trained on its unique cross-network transaction dataset. Improves authorization rates, routing, and fraud detection. At launch, improved card-testing attack detection by 64% on large businesses. This is the competitive moat that grows with every transaction processed — a data flywheel no smaller payment processor can match.

Original illustration from this archived newsletter

The “Singularity” Framing

In the Bloomberg interview, John Collison offered an unusually candid macro view — the Collison brothers have been tracking what they call “Day 1 of the singularity” starting January 1, 2026. As of the interview, they were ~190 days in.

“The coding models have gotten so good that they are now contributing in a significant way to the rate of improvement of AI itself. Today AI is really good and it’s getting better as a result of the quality of the AI.”

This is not hyperbole from a founder seeking capital. It is a thesis about why the AI era is structurally different from prior technology cycles — and why the companies building the financial plumbing for that era (like Stripe) are in an exceptionally favorable position. Every new AI product that gets built needs a payment processor, a billing engine, a fraud detection system, and increasingly a stablecoin infrastructure layer. Stripe has all four.

Original illustration from this archived newsletter

Revenue & Finance Automation Suite

One of Stripe’s most underappreciated growth vectors. This suite (Billing, Tax, Revenue Recognition, Invoicing, Radar) is on track to hit $1B annual run rate in 2026— doubling from $500M in February 2025. This is enterprise SaaS-grade revenue growing at a pace that would make it a standalone unicorn. Combined with Metronome, Stripe is building a full financial operations stack for AI-era businesses.

The PayPal Question

Bloomberg reported in February 2026 that Stripe has expressed preliminary interest in acquiring all or parts of PayPal. Collison declined to comment at the interview: “We never comment on M&A speculation.”

The strategic logic, if accurate, is straightforward:

  • PayPal has 400M+ consumer wallets — the consumer identity layer Stripe currently lacks

  • Stripe has superior enterprise infrastructure — Stripe would accelerate its direct consumer presence

  • Venmo + Stripe would create a vertically integrated payments network spanning consumer wallets, business infrastructure, and now AI agents

The challenge: PayPal’s market cap is ~$60–70B, making a full acquisition dilutive or debt-intensive at scale. A more likely scenario would be an acquisition of specific PayPal assets (Venmo, Braintree, or the consumer wallet infrastructure) rather than the entire company.

Original illustration from this archived newsletter

IPO Outlook

No formal IPO timeline has been confirmed. No lead underwriter selection or S-1 filing has been reported. However:

  • The February 2026 tender offer at $159B with Thrive Capital, Coatue, and a16z is widely interpreted as a pre-IPO liquidity signal

  • Octagon AI modeling suggests the market expects a formal IPO announcement before June 1, 2027

  • Stripe’s 2025 annual letter — stressing profitability, scale, and AI positioning — reads like an S-1 pre-read

For pre-IPO investors: Stripe has done multiple tender offers to provide employee and early investor liquidity without going public. The IPO will happen when the founders are ready, not when the market demands it. Patrick and John Collison are famously long-term oriented. COACH KYLE’s 2 Cent’s- I Think Stripe will finally come public in the first half of 2027, would think they will do a direct listing because they dont need to raise any money.

Competitive Landscape

Company

Valuation / Status

TPV (2025)

Positioning

Stripe

$159B (private)

$1.9T

Full-stack financial infrastructure + AI commerce leader

Adyen

~$40B (public, AMS: ADYEN)

~€1.3T

Enterprise-first; strong international; lower developer focus

PayPal / Braintree

~$65B (public, PYPL)

~$1.7T

400M consumer wallets; losing enterprise share

Fiserv / First Data

~$80B (public, FI)

N/A

Legacy banking infrastructure; not developer-native

Checkout.com

~$11B (private)

N/A

Strong in enterprise international; narrower product scope

Square / Block

~$30B (public, SQ)

~$245B

SMB-focused; crypto/Cash App exposure

Stripe holds ~25% of the U.S. payment management market — the clear market leader. Adyen is the most credible enterprise alternative at ~9.26% market share but is Europe-centric and does not have the AI commerce partnerships Stripe has built.

The competitive moats are deep and compounding:

  1. Network effects — 250M Link users; Payments Foundation Model improves with every transaction

  2. Switching costs — A company running Stripe Payments + Billing + Tax + Radar + Capital is effectively locked in

  3. Developer love — Stripe invented the “developer-first” payments experience; competitors have never caught up on API quality or documentation

  4. AI partnerships — Google, Microsoft, OpenAI, Anthropic, Meta, Perplexity all work with Stripe; this network is an enormous distribution moat

Original illustration from this archived newsletter

Key Risks

Valuation
At $159B, Stripe is priced at approximately 23x 2025 net revenue. That is a premium multiple that requires continued high-growth execution. Any IPO below this valuation would represent a down-round for recent tender offer participants.

Regulatory / Stablecoin Compliance
Bridge’s card program was paused in early 2026 following fraud incidents tied to Venezuela-linked client activity. Ongoing OCC charter opposition could limit cross-border stablecoin expansion. This is a real, near-term risk to one of Stripe’s most exciting growth vectors.

Take-Rate Compression
At 0.40% net take-rate, large enterprise customers have pricing leverage. As Stripe scales toward the very largest merchants and platforms, margin pressure is structurally built in.

Bank Partner Dependency
Stripe relies on partner banks (Wells Fargo, Cross River, Evolve, Lead Bank) for BaaS infrastructure. Wells Fargo’s exit from BIN sponsorship in 2024 created operational disruption. Regulatory scrutiny of fintech-bank partnerships is increasing.

Modular Competition
Best-in-class point solutions — Orb (billing), Lithic (card issuing), Anrok (tax) — compete for specific layers of Stripe’s platform. Enterprises that want the absolute best tool for each function rather than an integrated platform may prefer this approach.

IPO Pricing Uncertainty
The gap between the $159B tender offer price and what public markets will bear at IPO is unknowable today. If the broader tech market contracts, pre-IPO investors could face mark-to-market losses before any IPO occurs.

AI Commerce Adoption Speed
The agentic commerce thesis requires consumers and businesses to trust AI agents with purchase authority. The trust curve Collison describes is real — but could move slower than anticipated, particularly in regulated industries or high-value transactions.

Original illustration from this archived newsletter

Macro Tailwinds

  • AI replatforming of commerce — Every AI product built needs a payment layer; Stripe has positioned itself as the default infrastructure for the AI software economy

  • Stablecoin adoption — USDC and stablecoin payment volume is growing rapidly; Stripe is the primary on-ramp between fiat and stablecoin commerce at scale

  • Usage-based billing as the new SaaS model — Metronome + Stripe Billing creates the definitive metering and monetization platform for AI-era software companies

  • Global e-commerce growth — 57% of businesses newly onboarded to Stripe in 2025 were outside the U.S.; international expansion is a durable multi-year tailwind

  • Developer ecosystem flywheel — Stripe remains the default choice for developers building new products; this creates a constant flow of new businesses entering the Stripe ecosystem

  • Recursive AI improvement — As Collison noted, AI improving AI creates an accelerating technology cycle; every acceleration creates more demand for financial infrastructure

Conclusion

Stripe is one of the most exceptional private companies in the world — and it is at an inflection point. The transition from “payments infrastructure for the internet” to “financial infrastructure for AI” is not a pivot; it is a natural extension of what Stripe has always done. The company that built the default payment API for startups is now building the default payment layer for AI agents, per-token billing, stablecoin commerce, and agentic transactions.

The numbers back it up. $1.9 trillion in payment volume, $6.9 billion in revenue, $1.2 billion in EBITDA, 34% growth, profitable, and accelerating. The product surface area is expanding — Metronome, Bridge, Privy, Link at 250M users, Radar blocking 3M+ fraud attempts per month from just eight AI companies. This is not a single-product company riding one wave; it is a financial operating system for the modern internet.

The risks are real — valuation at $159B, stablecoin compliance exposure, take-rate pressure, IPO timing uncertainty. But for long-horizon investors with access to pre-IPO allocation, the core question is simple: will the internet economy and AI economy continue to grow, and will Stripe continue to take its share of that growth? The answer to both appears yes.

Stripe is not a bet on payments. It is a bet on the financial layer of the internet — and increasingly, the financial layer of artificial intelligence itself.

– “ Stripe is a blue chip disrupter and Trillion Dollar Company on sale for $150 Billion” – Coach Kyle

Original illustration from this archived newsletter

G.L.A. Invest Research — For informational purposes only. Not financial advice. Past performance does not guarantee future results.