AI | There were too many big stories in AI this month to count…OpenAI's $110B funding round, the largest private funding round in venture history, was led by Amazon at $50 billion, Nvidia at $30 billion, and SoftBank at $30 billion, pushing OpenAI's valuation to $730B pre-money. The Amazon piece is particularly interesting: the two companies inked a partnership, with AWS becoming the exclusive third-party cloud distribution provider for OpenAI Frontier, the company's enterprise platform for building and deploying AI agents. OpenAI is now targeting roughly $600B in total compute spend by 2030, with revenue projections exceeding $280B. The IPO clock is also ticking, with the round coming ahead of the AI startup's expected mega-IPO later this year. On the model side, Anthropic kept its foot on the gas. Claude Sonnet 4.6 dropped on February 17, Anthropic's second major model launch in under two weeks. Customers spending over $100,000 annually on Claude have increased 7x YoY, and the number of customers spending $1M+ grew from roughly 12 two years ago to over 500 today. But it’s not all bright and sunny on Anthrophic’ side. After weeks of tense negotiations, President Trump ordered every federal agency to immediately cease all use of Anthropic's technology, and the Pentagon declared the company a national security supply chain risk, a designation previously reserved for adversarial foreign firms like Huawei. The dispute came down to two non-negotiables Anthropic refused to drop: AI-controlled weapons and mass domestic surveillance of American citizens. Anthropic announced it would challenge the designation in court. Hours later, OpenAI stepped into the vacuum, announcing its own deal with the DoD that included the same safeguards Anthropic had requested: no domestic mass surveillance and human responsibility for lethal force. The optics of that landing were complicated. Some people argue that Anthropic did this to themself as MIT physicist Max Tegmark argued that by resisting binding regulation in favor of self-governance, and then, the same week as the Pentagon fight, quietly dropping the central tenet of its own Responsible Scaling Policy, its promise not to release increasingly powerful models until confident they wouldn't cause harm. In the absence of external rules, there's not much left to protect any of these players. The beef is so real that both Sam and Dario avoided holding hands at India’s AI Impact Summit. 😵‍💫Meanwhile, Meta made its own massive infrastructure move, striking a deal to purchase potentially up to $100B in AMD chips, enough to drive roughly six gigawatts of data center power demand, as Zuckerberg chases what he's calling "personal superintelligence. AMD also issued Meta a performance-based warrant for up to 160 million shares, about 10% of the company, vesting against compute deployment milestones. Talk about a sweetheart deal 😉

IPO WATCH | SpaceX is preparing a confidential draft IPO registration targeting a June listing, pursuing a valuation above $1.75 trillion and a raise of up to $50 billion. 👀 The valuation has more than doubled since mid-2025, boosted by its all-stock merger with xAI and Starlink, and surpassed $10B in revenue last year, with 9.2 million active subscribers. At $1.75 trillion, it would be bigger than Meta, Tesla, and every S&P 500 company except Nvidia, Apple, Microsoft, Alphabet, and Amazon. Then comes OpenAI: the company has begun informal talks with Wall Street banks and hired new finance executives for a Q4 2026 listing targeting a $1 trillion valuation, with concern that Anthropic could list first and absorb retail demand, reportedly driving the urgency. Three companies at the frontier of AI and aerospace, all potentially going public within twelve months of each other. Canva is the quieter name we’re continuing to watch closely. The company closed 2025 with $4B in ARR, 265 million monthly active users, and over 31 million paid subscribers. The company was last valued at $42 billion in a secondary share sale, and leadership has indicated an appetite for a public listing.

VENTURE CAPITAL | We’ve got liquidity!! Stripe announced a tender offer valuing the company at $159B, with investors including Thrive Capital, Coatue, and Andreessen Horowitz buying shares from current and former employees. That's a 74% jump from its $91.5B valuation a year ago. Total payment volume hit $1.9 trillion in 2025, up 34% year over year, and the company's revenue suite is on track to hit a $1B annual run rate this year. The Collisons remain in no hurry to go public, which is increasingly a strategic posture rather than a hedge. A week later, Plaid confirmed employees had sold shares at an $8B valuation, a 31% increase from the $6.1B it reached in April, with the round partly designed to help employees cover taxes on expiring RSUs. Despite the bump, Plaid is still 40% below its $13.4 billion peak from 2021. Together, the two deals sketch a clear picture of where private fintech infrastructure is heading: tender offers as a liquidity strategy, AI firms as the fastest-growing customer cohort, and no urgency whatsoever to list. The transatlantic performance gap in VC is also widening. North America's rolling one-year IRR reached 7.7% in Q2 2025, while European returns oscillated in negative territory, hitting -4.8% in Q2. The core driver is AI concentration: US deal value rose nearly 90% in the first half of 2025 compared to the same period the prior year, while VC funding in Europe dipped nearly 4%, with US AI funding reaching $222 billion versus roughly $28 billion in Europe. Exits are happening faster and at higher multiples in the US, which compounds the IRR gap. Europe has dry powder, but dry powder doesn't produce returns.

BYE FROM BLOCK | Jack Dorsey announced this month that Block is cutting more than 4,000 employees, nearly half its global workforce, taking it from over 10,000 workers down to just under 6,000. He broke the news in an all-lowercase post on X, telling staff directly: "today we're making one of the hardest decisions in the history of our company." (very genz) Regardless of Block's strength, gross profit is growing, but a significantly smaller team using AI tools can simply do more and do it better. Stock surged more than 24% in after-hours trading. Dorsey's parting message to the rest of the industry was pretty direct: "I think most companies are late. Within the next year, I believe the majority of companies will reach the same conclusion and make similar structural changes." Block nearly doubled its headcount between late 2020 and 2025, and its share price fell by more than 75% over the same period.

DISNEY TO DEFENSE PIPELINE | What have you been doing as Bridgit Mendler was spending her teens as the face of Disney Channel, her 20s at Harvard Law, and is now the CEO of one of the more interesting defense-adjacent startups in the country? This month, she closed a $100M Series B co-led by a16z and Washington Harbour Partners and a $49.8M Space Force contract in the same week. Her company, Northwood Space, is building Portal, a modular phased-array ground station that can be built and deployed in as little as 12 hours, versus an industry standard of 18 months, tracking satellites across LEO, MEO, and GEO orbits simultaneously without mechanical movement. The Space Force contract covers a three-year agreement to increase capacity on the Satellite Control Network, including support for tumbling or lost-contact satellites after deployment. Turns out you can just do things! 🫡

KALSHI | A Bloomberg analyst published a report this month arguing that prediction market users lose money faster than traditional gamblers. The data, sourced from a small outfit called Juice Reel, showed that the bottom quarter of prediction market users lost about 28 cents of every dollar bet in their first three months, compared to 11 cents on traditional online gambling sites. For the worst decile, first-90-day losses climbed to 44%. Uncomfortable numbers for a category that has spent the last two years pitching itself as a smarter, more intellectually serious alternative to sports betting. Kalshi's response? The company told Bloomberg the analysis was part of an "extortion" plot by Juice Reel, alleging that the firm's founder had previously sought investment from Kalshi and offered to help quash the report in exchange for a meeting with Kalshi's CEO. Juice Reel's founder, Ricky Gold, said the exact opposite: that it was Kalshi that reached out to him, trying to get him to repudiate the data, and that the extortion allegation came as a complete surprise. Hours later, Kalshi quietly walked back the characterization, saying that while it continued to dispute the findings, it no longer believed the intention was extortion. Oops 😀.

Omaha-based Alpaca wrapped a $1.2M Seed round

7 Rivers wrapped a $5M Series A, based in Milwaukee

Graici, an Ohio-based AI company, closed a $7.5M Series A

Ann Arbor-based Circadian Risk raised a $6M Series A

Minneapolis-based Mazzah raised a $2M Seed

Chicago-based startups closed a few rounds this month

and across Illinois

Indy-based Bearing wrapped a $4.5M Seed