Top News | Perplexity is doing more Perplexity things: And what does that mean? Getting into legal scraps and raising money. We kid, but the company — currently pursuing a massive valuation gain on the back of quick revenue growth — does seem to get into legal trouble quite often. This time it’s the Dow Jones and New York Post alleging copyright infringement. Previously, the New York Times sent the company a cease-and-desist letter, while Forbes threatened the startup with legal remedies earlier this year. Stripe snags Bridge: Private-market payments giant Stripe is buying stablecoin technology startup Bridge in a deal pipped at around the $1 billion mark. Stablecoins have seen their star rise in recent quarters, thanks to growing prominence of Circle, the company behind USDC, and strong demand for the digital tokens. Fans of fiat currencies, don’t worry. Stablecoins bring fiat on-chain, which is an ironic killer use-case for blockchains. Sophos to acquire Secureworks: One more deal to round us out today, this time from the realm of cybersecurity. Sophos, owned by private equity, is buying Secureworks, which was public and majority-owned by Dell for around $859 million. That’s less than the value it went public, but it is another proof point that the cybersecurity M&A market is far from moribund. If you are a cybersecurity company, at least.
| A New Addition to the TWiST500 | First, an apology. I thought we had already added Perplexity to the TWiST500. We hadn’t. As of this afternoon, it’s now on the list. | Why? Because its revenue growth appears to be vertical. Here’s the WSJ: | The startup’s annualized revenue—an extrapolation of the next 12 months’ revenue based on recent sales—is currently about $50 million, the knowledgeable people said. In March, its annualized revenue was a little over $10 million. |
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| Multiplying your revenue that quickly in such a short period of time is an incredibly impressive result for any startup. Mix in eight figures worth of queries per day, and it’s clear that Perplexity has captured the proverbial lightning in a bottle. | Recall that the TWiST500 is predicated on companies with the potential to have the largest financial returns, a proxy for how much of the world they disrupt. Perplexity, if it does manage to raise at the $8 to $9 billion it is targeting, will — on paper, to start — provide a number of venture funds with a huge IRR boost. | And with a valuation that large, Perplexity is pricing itself into “IPO or bust” territory pretty quickly. Excellent. Let’s see if the startup can speed-run the private markets and list next year. — Alex | A message from Brave | Brave is an internet privacy company on a mission to protect your personal info online. Download Brave today at https://brave.com/twist to browse faster, search privately and so much more. All in a single click. | This Week in Startups | E2028: Sarika Garg joins Alex to share her startup journey founding Cacheflow, addressing challenges in B2B sales and the complexities of SaaS billing. She discusses HubSpot’s acquisition of Cacheflow, integration into HubSpot's Commerce Hub, and its positioning as an AI company, along with key lessons on early exits, product-market fit, and organizational efficiency. Sarika also reflects on shifts in SaaS buying behavior, remote work, and future growth plans with HubSpot. | Startup Finance Basics: Kruze COO Scott Orn joins Jason to share top financial advice for startups, including managing cash flow and avoiding the pitfalls of over-fundraising. They explore growth strategies, legal considerations around financial representation, and how to maintain credibility with VCs. Key insights also cover building a strong financial plan and the evolving landscape of funding with a focus on regulatory issues. | E2027: Jason and Alex discuss the FTC's new subscription rules and their potential impact on businesses. They dive into Density's announcement of their "Waffle" product and how real-time data tracking is shaping city planning and operational efficiency. Other topics include the economics of sensor technology, the rise of robotaxi fleets, and nuclear energy deals involving Google, Kairos, and Amazon. | TWiST Partner Offers | AssemblyAI: Get maximum value from voice data with AssemblyAI. Build powerful products and features for your end users on the industry’s leading speech-to-text models. Get 100 free hours to start building at https://www.assemblyai.com/twist Vanta: Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at https://www.vanta.com/twist Runway: Looking to up-level your financial planning? Runway is the modern and intuitive way to model, plan, and align your business for everyone on your team. Sign up at https://runway.com/twist to get your first 3 months free.
| Founder University | Founder University Cohort 9 will kick off on October 25th. It’s a 12-week remote pre-accelerator program tailored to navigating early-startup practices, building an MVP, and growing traction. There’s still time to apply—submit your application at Founder University. | | The TWiST500 newsletter is the new, updated, and improved TWiST Ticker. |
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