1. The Landscape
~50 YC-funded fintech startups, from (Stripe) to . Two overwhelming trends: AI agents automating financial workflows and insurance is eating fintech (10+ companies in insurance alone). They cluster into 9 categories:
| Category | Count | Key Companies |
|---|---|---|
| Insurance (AI-powered) | 10 | Panta, Casey, Fernstone, Acolite, Avallon AI, Solva, Vantel, Amera, Newfront, Corgi |
| Payments / Neobanking | 8 | Stripe, SpotPay, Munify, Ruvo, Infinite, Unifold, Razorpay, Wave |
| Trading / Exchanges | 7 | QFEX, Forum, Sequence Markets, PAX Markets, Axiom, Freeport Markets, Scalar Field |
| Lending / Mortgages | 6 | Chestnut, Ralo, Proximitty, Kita, Veritus, Casca |
| Wealth Management / Investing | 5 | Autonomous Technologies, Astor, Groww, SmartAsset, Coinbase |
| Investment Banking / Alt Assets | 3 | Maywood, Alt-X, Sava |
| Corporate Finance / Spend | 3 | Brex, Rally, Truebill |
| Compliance / RegTech | 2 | Fenrock AI, Axis |
| Payroll / HR Fintech | 2 | Shor, Zavo |
Key observation: Insurance is the surprise winner — 10 companies, more than payments or trading. Why? Insurance is a $5 trillion industry with workflows still run on fax machines, PDFs, and manual spreadsheets. AI agents can automate the most painful parts (claims processing, submissions, underwriting). The opportunity is real.
Second observation: The giants in this list are enormous. Stripe, Coinbase, Brex, Razorpay, Groww — these are multi-billion-dollar companies. The bar for "notable YC fintech" is higher than any other category.
2. Full Company List
Giants (established, multi-billion-dollar companies)
- Stripe (S2009)
- Global payment infrastructure for the internet. $95B+ valuation. The gold standard.
- Coinbase (S2012)
- Crypto exchange and wallet. Public company (NASDAQ: COIN).
- Brex (W2017)
- AI-powered corporate cards, expense management, business accounts. $12B+ valuation.
- Razorpay (W2015)
- Full-stack payments and banking for India. $7.5B valuation.
- Groww (W2018)
- India's largest stock broker and mutual fund distributor.
- Wave (W2012)
- Affordable financial infrastructure for Africa. Mobile money.
- SmartAsset (S2012)
- Financial education and advisor marketplace.
- Truebill / Rocket Money (W2016)
- Personal finance app. Acquired by Rocket Companies.
- Newfront (W2018)
- Modern insurance brokerage with real-time data. $2B+ valuation.
W2026 Batch (11 companies)
- Proximitty
- AI-native loan management system with unified lending data and dynamic risk scoring.
- Unifold
- Developer-first API for accepting on-chain crypto deposits across multiple chains.
- Maywood
- Automates deal execution for investment banks: presentations, models, diligence.
- Fenrock AI
- AI agents preventing financial crimes for regulated institutions. Compliance audit logs.
- Axis
- AI research platform for commodities trading market analysis.
- Forum
- First regulated exchange to trade on "cultural attention" via search/social data indices.
- SpotPay
- Global borderless neobank: multi-currency payments, transfers, cards.
- Sequence Markets
- Execution technology improving trade routing across digital-asset venues.
- Kita
- Document intelligence for lending in emerging markets using vision-language models.
- Panta
- Autonomous commercial insurance brokerage run by AI agents.
- Grade
- B2B fintech solution (limited details available).
F2025 Batch (9 companies)
- Autonomous Technologies Group
- "Superintelligent financial advisor" at 0% advisory fees. AI wealth management.
- Amera
- Automates health insurance claims: messy documents → structured data.
- Sava
- Platform for trusts, estates, RIAs, and family offices.
- Alt-X
- AI infrastructure for alternative asset underwriting. Automates Excel-based deal models.
- Casey
- Automates commercial insurance submissions and carrier-ready risk profiles.
- Fernstone
- Full-stack insurance brokerage for complex construction and security risks.
- Selfin
- AI-powered banking with personalized financial recommendations.
- Freeport Markets
- AI analysts translating breaking news into actionable trade ideas.
- Zavo
- AI point-of-sale for restaurants: payments, operations, automation unified.
S2025 Batch (7 companies)
- Munify
- Cross-border neobank for Middle East diaspora: USD accounts, Visa cards, remittance.
- Ruvo
- Global account connecting Pix, crypto, and Visa for USD/BRL transfers.
- Astor
- AI investment advisor for retail investors. Opportunity discovery and analysis.
- Solva
- Domain-specific AI for complex insurance claims processing.
- Shor
- Employer-of-Record using AI agents + stablecoins for global payroll at reduced cost.
- Veritus
- Omni-channel AI agents for loan servicing and collections.
- Freya
- Retail fintech with AI capabilities (limited details).
X2025 Batch (6 companies)
- Chestnut
- First AI mortgage lender. Automates 99% of underwriting.
- Acolite
- AI teammates for insurance: submissions, COIs, SOV mapping across AMS systems.
- QFEX
- 24/7 exchange for US equities, commodities, and FX with leveraged perpetuals.
- Scalar Field
- AI-powered terminal: financial agents test market hypotheses.
- Ralo
- Mortgage platform: lower rates by automating processing and eliminating intermediaries.
- Avallon AI
- Automates insurance claims operations: AI agents for calls and document processing.
W2025 Batch (7 companies)
- Pluto
- First regulated exchange for compute resources. Finops infrastructure.
- Infinite
- Stablecoin payment processor: global money movement via APIs and SDKs.
- Rally
- Financial platform for vehicle fleet operations: fuel, maintenance, payroll.
- PAX Markets
- Crypto CEX with in-silicon exchange technology, nanosecond latency HFT.
- Axiom
- DeFi trading platform: memecoins, perpetuals, yield products.
- Vantel
- AI-native OS for commercial insurance brokerages.
- Invo
- Fintech company (limited details).
S2024 – W2024 Batch (notable companies)
- Casca (S2023)
- AI-native platform for small business lending. Banks originate 10x more loans with 90% less manual effort.
- Corgi (S2024)
- Full-stack insurance carrier building better products for startups.
- Paasa (S2024)
- Helps wealthy Indians invest in global equities without middlemen or hidden fees.
- Lucible (S2024)
- Combined checking + investment account. Invest 100% of your money while spending via real-time loans.
- The New Money Company (W2024)
- Invoice insurance: protects invoices and helps businesses expand to new buyer markets.
- Polar (W2024)
- Helps remote workers and freelancers manage USD earnings globally.
3. Category Clusters
Insurance (AI-powered) (10 companies — most crowded, biggest opportunity)
Panta, Casey, Fernstone, Acolite, Avallon AI, Solva, Vantel, Amera, Newfront, Corgi
The surprise of this analysis. 10 companies are attacking insurance — more than payments or trading. The sub-categories:
- Insurance brokerages (AI-native): Panta, Fernstone, Newfront, Corgi
- Insurance workflow automation: Casey (submissions), Acolite (COIs), Vantel (brokerage OS)
- Claims processing: Avallon AI, Amera, Solva
Why so many? Insurance is a $5 trillion industry running on fax machines, PDFs, and spreadsheets. Back-office work is almost entirely manual. AI agents can automate 80%+ of the paperwork. The margins are enormous (brokerages keep 10–20% commissions).
Payments / Neobanking (8 companies)
Stripe, SpotPay, Munify, Ruvo, Infinite, Unifold, Razorpay, Wave
Stripe and Razorpay are the giants. New entrants target niches: cross-border (SpotPay, Munify, Ruvo), crypto rails (Unifold, Infinite), and emerging markets (Wave, Kita). The pattern: pick a corridor or region underserved by Stripe.
Trading / Exchanges (7 companies)
QFEX, Forum, Sequence Markets, PAX Markets, Axiom, Freeport Markets, Scalar Field
From 24/7 equities exchanges (QFEX) to "cultural attention" indices (Forum) to DeFi perpetuals (Axiom). Heavy regulation, massive capital requirements, and infrastructure complexity. Not bootstrappable.
Lending / Mortgages (6 companies)
Chestnut, Ralo, Proximitty, Kita, Veritus, Casca
AI automating underwriting (Chestnut), loan management (Proximitty), document extraction (Kita), and collections (Veritus). Casca is interesting: helps existing banks originate 10x more small business loans. Selling to banks rather than competing with them.
Wealth Management / Investing (5 companies)
Autonomous Technologies, Astor, Groww, SmartAsset, Coinbase
The "AI financial advisor at 0% fees" pitch (Autonomous Technologies, Astor) is compelling but regulatory-heavy. Groww and Coinbase are established platforms.
Investment Banking / Alt Assets (3 companies)
Maywood, Alt-X, Sava
Automating deal execution (Maywood), underwriting models (Alt-X), and trust/estate management (Sava). Niche, high-value, enterprise-only.
Corporate Finance / Spend (3 companies)
Brex, Rally, Truebill
Brex owns corporate cards. Rally targets fleet finance. Truebill was acquired. Brex's moat is real: integrated cards + expense management + accounts.
Compliance / RegTech (2 companies)
Fenrock AI, Axis
Fenrock (financial crime prevention) and Axis (commodities research). Compliance is mandatory spend for financial institutions — same dynamic as SOC 2 compliance in the security analysis.
Payroll / HR Fintech (2 companies)
Shor, Zavo
Shor (global payroll with stablecoins) and Zavo (restaurant POS). Shor is interesting: using stablecoins to reduce cross-border payroll costs.
4. Applying the DHH / Jason Fried Filter
The fintech problem: Most fintech categories require licenses, banking partners, compliance teams, and significant capital. This kills 80% of the bootstrap options. The filter is even stricter here:
5. Categories to Skip
| Category | Why Skip |
|---|---|
| Payments / Neobanking | Stripe exists. Banking licenses, money transmission, compliance, capital reserves. The most regulated fintech category. Skip. |
| Trading / Exchanges | Requires exchange licenses (SEC, CFTC), matching engines, custody solutions, massive capital. 7 VC-funded companies already. Skip. |
| Lending / Mortgages (as a lender) | Requires lending licenses, credit underwriting, capital reserves, loss provisions. Skip being a lender. But selling tools to lenders is viable. |
| Wealth Management (consumer) | SEC/FINRA registration, fiduciary obligations, compliance. Skip. |
| Investment Banking | Enterprise-only, long sales cycles, relationship-driven. Skip. |
| Corporate Cards / Spend | Brex at $12B. Requires bank partnerships and credit underwriting. Skip. |
The pattern: anything that involves touching money or being a regulated financial institution is not bootstrappable. What is bootstrappable: selling software tools to financial institutions.
6. What Survives the Filter
Option 1: Insurance Workflow Automation — the #1 pick
Why: 10 YC companies in insurance = massive validated demand. But most are building brokerages (regulated, capital-heavy). The bootstrappable angle: sell software tools to existing brokerages. Casey (automates submissions), Acolite (COI management), Vantel (brokerage OS) do exactly this.
Insurance brokerages are:
- Small businesses (thousands of independent brokerages in the US alone)
- Using ancient software (Applied Epic, AMS360 — decades-old, universally hated)
- Willing to pay for tools that save time on paperwork
- Not price-sensitive (they make high commissions)
The DHH play:
- A simple SaaS tool that automates one painful insurance workflow.
- Start with: certificate of insurance (COI) tracking or submission automation.
- $200–500/month per brokerage. Self-serve.
- No insurance license required — you are selling software, not insurance.
- LinkedIn is full of insurance brokers who hate their current tools.
Option 2: Financial Compliance / RegTech Tools
Why: Fenrock AI (financial crime prevention) validates the demand. Every bank, fintech, and money services business is legally required to do KYC, AML, and SAR filing. Same dynamic as SOC 2 compliance: mandatory, recurring, non-optional spend.
The DHH play:
- A simple KYC/AML screening tool for small fintechs and MSBs.
- $100–500/month. Pay per check or flat rate.
- Incumbents (Chainalysis, Jumio, Onfido) charge enterprise prices.
- Small fintechs and crypto companies need affordable compliance.
- API-first: easy to integrate, hard to churn.
Option 3: Lending Tools (sell to lenders, don't be one)
Why: Casca helps banks originate 10x more loans. Proximitty does loan management. Kita does document extraction for lending. The pattern: don't be a lender — sell tools to lenders. Banks and credit unions are desperate to modernize but move slowly.
The DHH play:
- A document extraction tool for loan applications: upload PDFs, get structured data.
- Or: a simple loan servicing dashboard replacing spreadsheets.
- $300–1000/month per lender.
- Target: community banks and credit unions (thousands in the US, underserved by enterprise vendors).
Option 4: Invoicing / Billing Tools for SMBs
Why: Lumen Payments (from the open source analysis) does complex pricing models. The New Money Company does invoice insurance. Every small business needs to send invoices and get paid. FreshBooks does $100M+ ARR. Wave (accounting, not the African fintech) was acquired for $537M.
The DHH play:
- A dead simple invoicing tool. Send invoice → get paid. No accounting suite bloat.
- $15–50/month. Or take a small % of payment volume.
- Target freelancers and micro-businesses (millions of them).
- No banking license needed if you use Stripe/PayPal as the payment rail.
- Add AI: auto-generate invoices from time tracking, auto-chase late payments.
Option 5: AI Financial Document Processing (productized service)
Why: Multiple companies are building AI for financial documents: Kita (lending docs), Amera (insurance claims), Alt-X (deal models), Maywood (IB presentations). Financial institutions drown in PDFs. This is a service you can sell today with existing AI tools.
The DHH play:
- Not a platform. A productized service.
- "Send us your financial PDFs, we extract the data into spreadsheets."
- $500–2000/month per client, or per-document pricing.
- Use Claude/GPT-4 + custom prompts to process documents.
- Target: small lending shops, insurance agencies, accounting firms.
- Zero code to maintain. Pure margin.
7. The Street-Smart Verdict
| Option | SNOLOC | TTFP | Recurring? | Bootstrap Score |
|---|---|---|---|---|
| Insurance workflow SaaS | Medium | Weeks | Monthly | |
| Financial doc processing (service) | ~0 (service) | Days | Monthly | |
| Compliance / RegTech tool | Medium | Weeks | Monthly | |
| Invoicing for SMBs | Low–Medium | Weeks | Monthly | |
| Lending tools | Medium–High | Months | Monthly |