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January 4th, 2024
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Tailscale Raises $230M to Power Identity-First Networking
Funding | April 9, 2025
Image from Tailscale's Series C blog announcement
Toronto’s Tailscale Secures $230M and $2B Valuation for Identity-First Networking
On April 8 2025, Toronto-based Tailscale announced that they raised $230 million CAD Series C (about $160 million USD), valuing the company at approx $2 billion CAD. The round was made up of U.S. investors, led by Accel, CRV, Insight Partners, Heavybit, and Uncork Capital, along with some prominent individual investors notably George Kurtz CEO of CrowdStrike (returning investor) and Anthony Casalena CEO of Squarespace. New funds will be used to grow product and engineering teams, expand globally, and improved support for fast scaling customers.
Tailscale - A Shift from IP Addresses to Identity
Tailscale was founded in 2019 by former Google engineers Avery Pennarun, David Crawshaw, David Carney, and Brad Fitzpatrick, and officially launched in April 2020 to help users connect devices and apps securely without relying on traditional VPNs, IP rules, or firewalls.
Tailscale uses a technology called WireGuard which is easy to setup and lets devices connect directly to each other, safely and privately. What's unique about Tailscale is its approach to solving networking challenges. Instead of relying on where a device is located (IP address), it focuses on who or what is connecting. This approach is called identity-first networking, and is a more modern solution in a world where teams work remotely, apps operate across various cloud platforms, and security rules are becoming stricter.
See: AI Concierge Tech and the Future of Finance
So instead of trusting a device because it has a certain IP address, Tailscale checks and verifies the identity of every user, device, or service trying to connect, making it easier for companies working in the cloud. Models that rely on firewalls, assume that any device inside the network is trustworthy while the risk is outside. But today's networks are too distributed for that approach to hold up today, making identity-first networking a more flexible and secure alternative for modern times.
Avery Pennarun CEO Tailscale describes it as:
“You’re connecting to your app, your teammate, your service — wherever it happens to be running right now.”
Which sectors could be disrupted?
Tailscale's model reduces/eliminates the need for traditional VPNs, static firewall rules, and perimeter defence, placing VPN and firewall vendors on notice. Managed service providers on traditional network configuration, such as port forwarding, IP management or hardware firewalls, will be under pressure as they lose relevance, assuming the identity-first networking movement continues to grow.
See: Securing Your IoT Network Against Emerging Threats
Further, any 'zero trust' solution that still relies on IP allowlists or geography-based filters are also at risk. Identity-first networking is meant to offer real Zero Trust, cryptographic identity access across dynamic environments, a better fit for compliance teams needing continuous monitoring and real time enforcement.
According to Betakit, Tailscale is already being used by over 10,000 clients, such as fast growing AI and tech companies like Perplexity, Cohere, Groq, Mistral and Hugging Face, alongside enterprises like SAP, Instacart, Telus, and Duolingo.
Notable Absence of Canadian Capital?
Although Tailscale is proudly based in Toronto, none of the firms participating in this $230M Series C were Canadian, reflecting a troubling pattern of Canadian innovation meets U.S. capital.
See: How Secure Networking Can Protect Your Business Data from Threats
While deep liquidity and quick deployment of global funding accelerates Tailscale's growth, the lack of domestic institutional investors in large scale Canadian tech rounds raises questions about ecosystem competitiveness, strategic alignment and ultimately, ownership retention long term. It's great for Canadian fintechs to have this kind of access to foreign capital but a real hurdle to build stronger investment pipelines at home.
Why It Matters for Fintechs
As digital interactions and businesses become more complicated, they need better ways to keep things secure by focusing on who or what is connecting, not just where it's coming from. Financial technology companies deal with reams of sensitive data, multiple cloud deployments, third party integrations, and remote teams, and are key prospects for using an identity-first networking solution. One that's secure and can scale with real-time access control by identity (user, device, or service), improved auditability for KYC and compliance, and easier cross-border infrastructure. Fintechs should take a fresh look at how their systems are built, and retool if necessary. The future of security, compliance, and growth will likely rely on identity-based technology at the core.
The National Crowdfunding & Fintech Association (NCFA Canada) is a financial innovation ecosystem that provides education, market intelligence, industry stewardship, networking and funding opportunities and services to thousands of community members and works closely with industry, government, partners and affiliates to create a vibrant and innovative fintech and funding industry in Canada. Decentralized and distributed, NCFA is engaged with global stakeholders and helps incubate projects and investment in fintech, alternative finance, crowdfunding, peer-to-peer finance, payments, digital assets and tokens, artificial intelligence, blockchain, cryptocurrency, regtech, and insurtech sectors. Join Canada's Fintech & Funding Community today FREE! Or become a contributing member and get perks. For more information, please visit: www.ncfacanada.org
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