Steadily vs Stripe
Side-by-side comparison of AI visibility scores, market position, and capabilities
Austin landlord insurance insurtech at $250M+ annualized GWP; $89.5M total ($30M Two Sigma Series C April 2025 at $355M) with Inc. 5000 #63/4,606% growth and own carrier launch Q4 2024 competing with Obie for individual landlord insurance.
About
Steadily is an Austin, Texas-based insurtech specializing exclusively in landlord insurance — backed with $89.5 million in total funding including a $30 million Series C in April 2025 led by Two Sigma Ventures at a $355 million valuation — providing America's 18 million individual rental property owners with fast, mobile-first insurance quotes for single-family rentals, multi-family units, condos, ADUs, short-term rentals (Airbnb/VRBO), and small apartment buildings in all 50 states, with $250+ million in annualized gross written premium. Inc. 5000 ranked Steadily #63 in 2025 with 4,606% three-year revenue growth. Steadily integrates with 400+ proptech platforms including Roofstock, TurboTenant, FurnishedFinder, and BiggerPockets. In Q4 2024, Steadily launched its own insurance carrier (Steadily Insurance Company), vertically integrating from MGA/distribution to risk-bearing carrier. Founded 2020 by landlords Darren Nix (CEO), Datha Santomieri, and David Tulig who experienced the limitations of the existing landlord insurance market firsthand.
Global payments infrastructure founded by Patrick and John Collison (YC W10); $1.4T payments volume in 2024; $18B+ revenue; $106.7B valuation as of Sept 2025; powers everything from startups to Fortune 500 companies with developer-first API design.
About
Stripe is a global payments infrastructure company founded in 2010 by Irish brothers Patrick and John Collison, headquartered in San Francisco, California and Dublin, Ireland. Stripe was born from the insight that accepting payments online was unnecessarily complex for developers, and that a well-designed API could unlock an entire generation of internet businesses. The company went through Y Combinator's Winter 2010 batch and grew to become the defining payments infrastructure layer of the modern internet economy, processing payments for businesses in virtually every industry worldwide.\n\nStripe's platform provides payment processing, fraud prevention via Stripe Radar, subscription billing, revenue recognition, banking-as-a-service through Stripe Treasury, corporate card issuance, identity verification, and tax compliance tools. It serves a spectrum from early-stage startups to publicly traded enterprises including Amazon, Google, Salesforce, and Shopify. Stripe's developer-first philosophy — comprehensive documentation, SDKs in every major language, and a sandbox testing environment — created an ecosystem of millions of businesses built entirely on its infrastructure.\n\nStripe processed $1.4 trillion in total payment volume in 2024 and generates over $18 billion in annual revenue, with a valuation of $106.7 billion as of September 2025. The company has remained private longer than most comparably sized technology companies, giving it flexibility to invest in long-term product expansion. An April 2024 partnership with Apple Pay extended Stripe's reach further into mobile and in-store commerce. Stripe competes with Adyen, Braintree (PayPal), and Square, but its developer ecosystem depth and global infrastructure make it the default payments platform for a generation of technology companies.
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