Trillion $$ Club
Brex/Zip, OpenAI/io, Airwallex, Nuclear, General Matter, X outage
Today’s Sourcery is brought to you by Brex..
Brex’s modern finance stack including the world’s smartest corporate card, expense tracking, banking, bill pay, and travel tools helped fuel Scale AI’s ascent from a 2016 startup to an impending $25 billion valuation (currently rumored tender offer: Founders Fund, Greenoaks Capital & Coatue plan to participate).
Starting with autonomous vehicle data, Scale AI pivoted to power AI models for OpenAI and Microsoft, growing 2024 revenue to $870M on a projected $1.5B annualized run rate. Scale AI is on path to 2x that this year, estimating $2B in revenue. Brex’s real-time spend visibility and integrations kept pace with their global expansion. Over 30,000 companies, including ServiceTitan, Anthropic, Mercor, DoorDash, and Wiz, use Brex to spend smarter and move faster.
$1T Acquisition Spree
OpenAI has turned on the M&A machine. As of late, OpenAI has begun to make several strategic acquisitions totaling almost $10 billion, reflecting its ambition to expand beyond AI research into hardware, enterprise solutions, developer tools, and well.. surpass it’s recent $300B valuation to reach the $1T-club.
Notably, OpenAI’s recent $6.5 billion acquisition of Jony Ive's hardware startup, io, and the $3 billion purchase of AI coding tool Windsurf underscore this shift. Other acquisitions include Rockset, a real-time analytics platform, and Multi, a video-first collaboration tool. These moves position OpenAI to compete more directly with existing $1T tech giants by integrating AI across various consumer & enterprise solutions.. but more obviously, with trillion-dollar aspirations you need a trillion-dollar designer. What better place to look than Apple?
This aggressive expansion mirrors a broader trend of billion-dollar tech acquisitions aimed at consolidating AI & cloud capabilities. In March 2025, Google announced its largest deal yet with the $32B acquisition of the insanely fast-growing cloud security firm Wiz. IBM completed its $6.4B purchase of HashiCorp in February 2025 to bolster its cloud infrastructure and automation stack. These moves reflect intensifying competition among tech giants to secure strategic technology & talent to remain sharp amid the big AI restructuring. Adapt, acquire, or die.
X was down bad..
On May 22, 2025, a fire in a lithium-ion battery room at a Digital Realty data center in Hillsboro, Oregon, leased by X, triggered a global outage that disrupted the platform for multiple days. Starting around 11:00 AM PT, the outage affected millions of users worldwide.. causing them to spiral, consider touching grass, or worse, enjoy a holiday weekend with loved ones. Users faced problems like inaccessible DMs, login failures, & slow-loading feeds.. personally, I wasn’t able to make our latest Sourcery interview with Whop CTO Jack Sharkey go viral. Bummer. Long live X.
Musings
Fintech
The Future of Finance is Modular | Why Best-of-Breed Partnerships are Winning, & What It Means for Finance Teams
Brex for Zip | Brex, the modern finance platform, & Zip, the world’s leading procurement orchestration platform, announce new partnership
Groundbreaking solution seamlessly integrating Brex’s global card capabilities directly into Zip’s procurement workflows.
Energy
Last week, President Donald Trump signed executive orders aimed at revitalizing the U.S. nuclear energy sector, a move critical for addressing the surging electricity demand driven by artificial intelligence and data centers. These orders seek to streamline regulations, expedite reactor approvals, and reduce dependence on foreign uranium supplies, particularly from Russia and China.
Scott Nolan, Founder & CEO of General Matter - Enriching uranium in America to fill the nuclear fuel gap
VC
Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN [20VC]
Cendana's Michael Kim on Characteristics of the Top VCs, How Seed Funds Compete vs Multistage Firms, Portfolio Construction Best Practices [The Peel]
204x DPI funds, why high ownership to fund size drives outlier returns, how secondaries are generating most early stage VC returns, the 60x rule, and inside Cendana's early days
More
PW is Back! Jony Ive & Sam Altman, Air Travel Is Awful, The Left's Joe Rogan, & Tech Updates [Pirate Wires]
Top Interviews
EXCLUSIVE: How Whop Hit $1.2+ Billion GMV Run Rate with Just 20 Engineers, CTO Jack Sharkey | 5B+ Creator Views, 28K+/mo Earners, $100M/mo
Erik Kriessmann, Partner at Altimeter: How Altimeter Is Investing $100M+ Checks | Anduril, SpaceX, K2 Space
Windsurf: The Making of a Billion-Dollar AI Company | Leigh Marie Braswell, Kleiner Perkins
→ Follow Sourcery on: X, YouTube, Spotify, Apple, Linkedin
Last Week (5/19-5/23):
Relevant deals include the 70+ deals across stages below. I've categorized the deals below into seven categories, Fintech, Care, Enterprise / Consumer, HardTech, Sustainability, Acquisition/PE, and Fund Announcements, and ordered from later-stage rounds to early-stage rounds.
VC Deals
Fintech:
- Airwallex, a Singapore-based global payments and financial platform, raised $300 million in Series F funding at a $6.2 billion valuation from Square Peg, DST Global, Lone Pine Capital, and others.
- RevenueCat, a San Francisco-based consumer app monetization platform, raised $50 million in Series C funding. Bain Capital Ventures led the round and was joined by existing investors Index Ventures, Y Combinator, Adjacent, and others.
- Slash, an SF-based "vertical banking" startup, raised $41m in Series B funding at a $370m valuation. Goodwater Capital led, joined by YC, NEA, Stanford University, and Menlo Ventures.
- Clair, a New York City-based earned wage access provider, raised $23.2 million in Series B funding. Upfront Ventures led the round and was joined by existing investors Thrive Capital and others.
- OpenFx, a cross-border payments infrastructure startup, raised $23m led by Accel
- Miter, an SF-based provider of human capital management software for construction and field services, raised $23m co-led by insiders Bessemer Venture Partners and Coatue.
- Keep, a Toronto-based financial platform for small businesses, raised $23 million in funding. Tribe Capital led the round and was joined by Rebel Fund, Liquid2 Ventures, Cambrian, and others.
- iAltA, a New York City-based private markets infrastructure company, raised $20 million in funding from WestCap and founders Laurence A. Tosi, Scott Ganeles, and Bill Sherman.
- Catena Labs, an "AI-native financial institution," raised $18m. A16z led, joined by Breyer Capital, Circle Ventures, Coinbase Ventures, CoinFund, Pillar VC, and Stanford Engineering VF
- Filed, a New York City-based AI-powered tax preparation platform, raised $17.2 million in funding. J Ventures led the $2.2 million pre-seed round and was joined by Neo, Raine, Greens Ventures, and angel investors. Northzone led the $15 million seed round and was joined by Day One Ventures and existing investors J Ventures, Neo, Raine, and Greens Ventures.
- Affiniti, a provider of expense management software for small businesses, raised $17m in Series A funding led by SignalFire, with insiders Indicator Ventures, RiverPark, and Lightshed Ventures participating.
- True Markets, a DeFi trading mobile app, raised $11m in Series A funding. Accomplice and RRE Ventures co-led, joined by Reciprocal Ventures, Variant Fund, and PayPal Ventures.
- Seeds, a New York City-based investing platform for financial advisors, raised $10 million in Series A funding. Portage led the round and was joined by existing investors Social Leverage and Blank Ventures.
- Button Finance, a New York City-based home equity lending fintech, raised $5 million in Series A funding. Hildene Capital Management led the round and was joined by existing investors
- Pay-i, a Redmond, Wash.-based cost management platform for GenAI projects, raised $4.9m in seed funding co-led by Fuse Partners and Tola Capital
Care:
- Strava, an SF-based fitness tracking platform, raised new funding at a $2.2b valuation. Sequoia Capital led, joined by TCV, Jackson Square Ventures, and Go4it Capital
- Sprinter Health, a Menlo Park, Calif.-based mobile healthcare services provider, raised $55 million in Series B funding. General Catalyst led the round and was joined by existing investors a16z Bio + Health, the Regents of the University of California, Google Ventures, and Accel.
- General Medicine, a telehealth provider and medical marketplace , raised $32m. Matrix Partners led, joined by BoxGroup, Founder Collective, VXI Capital, and JSL Ventures
- Dazos, a Boca Raton, Fla.-based software platform for behavioral health providers, raised $25m in Series A funding led by Radian Capital
- Axle Health, an LA-based provider of scheduling and workforce management software for in-home care providers, raised $10m in Series A funding. F-Prime Capital led, joined by YC, Pear VC, and Lightbank.
- Biostate AI, a Houston-based GenAI developer for disease and drug response prediction, raised $12 million in Series A funding. Accel led the round and was joined by Gaingels, Mana Ventures, InfoEdge Ventures, existing investors Matter Venture Partners, Vision Plus Capital, and Catapult Ventures, and angel investors.
- WellTheory, an Atherton, Calif.-based AI-powered autoimmune care platform, raised $5 million in funding from Samsung Next, Opal Ventures, Up2 Fund, and existing investors Accel, OVO Fund, and BoxGroup.
Enterprise/Consumer:
- Awardco, a Lindon, Utah-based employee recognition and rewards platform, raised $165 million in Series B funding at a $1 billion valuation from Sixth Street Growth, Spectrum Equity, and existing investors General Catalyst and Ryan Smith.
- LMArena, a San Francisco-based AI models evaluation open community platform, raised $100 million in seed funding. a16z and UC Investments led the round and were joined by Lightspeed, Laude Ventures, Felicis, and others.
- Gravitee, a Denver-based event stream and agentic AI management platform, raised $60 million in Series C funding. Sixth Street Growth led the round and was joined by existing investors Riverside Acceleration Capital and Albion VC.
- LMArena, an SF-based AI model reliability platform, raised $100m in seed funding co-led by a16z and UC Investments co-led, joined by Lightspeed, Laude Ventures, Felicis, Kleiner Perkins, and The House Fund.
- Ascendx Cloud, a London-based CRM startup, raised £45m in equity funding co-led by Osprey Investors and Columbia Lake Partners.
- Veesion, a Paris-based AI-powered surveillance software, raised $43 million in Series B funding. White Star Capital led the round and was joined by Red River West, Bpifrance, and existing investors Odyssée Ventures, Verve Ventures, and Founders Future.
- DataHub, a Palo Alto-based AI and data context management platform, raised $35 million in Series B funding. Bessemer Venture Partners led the round and was joined by 8VC, Tru Arrow, SineWave, and others.
- Palmstreet, a San Francisco-based rare plants, handmade crafts, and other goods live-shopping app, raised $25 million in funding. a16z, Craft Ventures, and Headline led the round and were joined by others.
- Sweep, a New York City-based agentic workspace for enterprises, raised $22.5 million in Series B funding. Insight Partners led the round and was joined by Bessemer Venture Partners.
- FanBasis, a Miami-based digital businesses operating system, raised $20 million in Series A funding. Left Lane Capital led the round and was joined by Ryan Serhant, Upside Ventures, Gerard Piqué, and Connexa Capital.
- BreachRx, a San Francisco-based intelligent incident response platform, raised $15 million in Series A funding. Ballistic Ventures led the round and was joined by SYN Ventures, Overline, and Silver Buckshot Ventures.
- Pixee, a Baltimore-based automated product security platform, raised $15 million in seed funding. Decibel and Wing VC led the round and were joined by TEDCO, PrimeSet, Zach Holman, and others.
- TrustCloud, a Boston-based AI platform for GRC, raised $15m. ServiceNow Ventures led, joined by Cisco Investments, Presidio Ventures, OpenView Venture Partners, and Tola Capital
- Rhino Federated Computing, an Israeli AI platform for regulated industries, raised a $15m Series A led by AlleyCorp, with participation from LionBird, Fusion Fund, Arkin Digital Health, Qiming Venture Partners USA, and Telus Global Ventures.
- Barndoor AI, a New York City-based agentic AI control plane, raised $13.6 million in seed funding. Crosslink Capital led the round and was joined by Preface Ventures, Precursor Ventures, Gaingels, and others.
- Tern, a Plymouth, Mich.-based business platform for travel agencies, raises $13 million in Series A funding. Viewpoint Ventures led the round and was joined by existing investors Upfront Ventures and Haystack VC.
- GrowthX, a San Francisco-based AI-powered marketing platform, raised $12 million in Series A funding. Madrona led the round and was joined by angel investors.
- StackHawk, an SF-based API security platform, raised $12m from Sapphire Ventures and Costanoa Ventures.
- Parkade, a San Francisco-based private parking management technology platform, raised $10 million in Series A funding. Navitas Capital, MassMutual Ventures, and 9Yards Capital led the round and were joined by existing investors CRV, Heartland, and Box Group.
- Cartwheel, a New York City-based AI-powered 3D animation AI tools provider, raised $10 million in funding. Craft Ventures led the round and was joined by WndrCo, Tirta Ventures, Runway, and existing investors Accel, Khosla, and Human Ventures.
- Optura, a Nashville-based AI-powered operating system for healthcare, raised $6.5 million in seed funding. Susa Ventures and Matrix led the round and were joined by angel investors.
- Mura, an AI platform for commercial field service operations, raised $6m in seed funding co-led by Level One Fund and Lerer Hippeau
- Zoca, a Tempe, Ariz.-based AI-powered marketing solution, raised $6 million in seed funding. Accel led the round and was joined by GTMfund, Elevation Capital, and Better Capital.
- AskElephant, a Draper, Utah-based AI-powered orchestration platform for customer-facing teams, raised $6 million in seed funding. Jump Capital led the round and was joined by High Alpha, Tandem, SaaS Ventures, and others.
- VOYA Games, a Berlin-based game studio, raised $5 million in funding. 1kx and Makers Fund led the round and were joined by RockawayX and angel investors.
- Theo Ai, San Francisco-based predictive legal AI platform, raised $4.2 million in seed funding. Existing investor NextView Ventures and Collide Capital led the round and were joined by Four Acres Capital, existing investors nvp capital, Ripple Ventures, Beat Ventures, SCVC Fund, and angel investors.
- Pay-i, a Redmond, Wash.-based ROI intelligence platform for GenAI, raised $4.9 million in seed funding. Fuse Partners and Tola Capital led the round and were joined by Firestreak, Pear VC, Gaia Capital, and angel investors.
- Studio 42, a Limassol, Cyprus-based mobile game studio, raised $3.6 million in seed funding. Play Ventures led the round and was joined by GEM Capital and Arcadia Gaming Partners.
- Algoma, a Brooklyn-based AI-powered real estate development platform, raised $2.3 million in seed funding. Zacua Ventures led the round and was joined by SOSV, Iron Prairie Ventures, DOMiNO Ventures, Compose VC, and angel investors.
- ThriveAI, a San Francisco-based AI-powered junior product manager, raised $1.2 million in pre-seed funding. 500 Global led the round and was joined by Iterative and Hustle Fund.
- PlaySafe ID, a London-based digital identity platform for online gaming, raised $1.1 million in pre-seed funding. Early Game Ventures led the round and was joined by Hartmann Capital and Overwolf.
HardTech:
- The Nuclear Co., a Lexington, Ky.-based nuclear energy developer, raised $51.3m in Series A funding. Eclipse led, joined by CIV, Goldcrest Capital, MCJ Collective, True Ventures, and Wonder Ventures.
- CX2, an El Segundo, Calif.-based electronic warfare technology developer, raised $31 million in Series A funding. Point72 Ventures led the round and was joined by 201 Ventures, Pa
- Blues, a Boston-based IoT connectivity startup founded by Ray Ozzie, raised $25m led by Sequoia Capital
- Converge, a concrete sensor startup, raised $22 million in new Series A funding. ABN Amro led, joined by Climate Investment, Move Energy, Pi Impact, J-Impact, TO Ventures, and Force Over Mass Capital.
- RoboForce, a Milpitas, Cali.-based robotic labor system developer, raised $5 million in funding from Myron Scholes, Gary Rieschel, and others.
- PsiQuantum, a Palo Alto-based quantum computer developer valued by VCs at $6.75b, is in talks to receive an investment from Nvidia
Sustainability:
- Novisto, a Montreal-based ESG data management and sustainability reporting company, raised $27 million in Series C funding. Inovia Capital led the round and was joined by existing investors White Star Capital, SCOR Ventures, Sagard, and all others.
- Rivan, a London-based synthetic fuel plants developer, raised £10 million ($13.4 million) in funding. Plural led the round and was joined by 20VC, NFDG, and angel investors.
- Alt Carbon, an Indian carbon removal startup, raised $12m in seed funding led by Lachy Groom.
- Rhizome, a Washington, D.C.-based climate resilience planning platform for power grids, raised $6.5m in seed funding led by Base10 Partners.
Acquisitions & PE:
- Charter Communications, a Stamford, Conn.-based cable company, agreed to merge with Cox Communications, an Atlanta-based cable company, at at an enterprise value of approximately $34.5 billion.
- OpenAI acquired io, an AI product startup founded by iPhone creator Jony Ive, for $6.5 billion.
- DICK’S Sporting Goods agreed to acquire Foot Locker, a New York City-based footwear retailer, at an equity value of approximately $2.4 billion and an enterprise value of approximately $2.5 billion.
- Together AI acquired Refuel.ai, a San Francisco-based data structuring solution. Financial terms were not disclosed.
- Match Group (Nasdaq:MTCH) acquired Her, a dating app for queer women
- Tripledot Studios acquired the mobile games studio portfolio of AppLovin, a Palo Alto-based audience growth and monetization technology developer, and a minority stake in the company for approximately $800 million, half cash and half equity.
- Robinhood Markets agreed to acquire WonderFi, a Toronto-based centralized and decentralized crypto company, at an equity value of approximately $250 million CAD ($179 million) in cash.
- Life360 invested $25 million in Aura, a Boston-based AI-powered online safety solution.
- Databricks agreed to acquire Neon, a San Francisco-based serverless Postgres platform. Financial terms were not disclosed.
- Huma acquired Aluna, a San Francisco-based lung health monitoring technology company. Financial terms were not disclosed.
- Regeneron Pharmaceuticals (Nasdaq: REGN) agreed to acquire the assets of bankrupt genetic testing company 23andMe for $256 million.
- Publicis (Paris: PUB) acquired Captiv8, a San Mateo, Calif.-based influencer marketing platform whose backers included UTA Ventures, Lone Wolf Partners, Launch Fund, and Joyance Partners.
IPOs:
- Hinge Health, a San Francisco-based musculoskeletal care devices developer, raised $437 million in an offering of 13.7 million shares (38% secondary) priced at $32 on the NYSE. The company posted $432 million in revenue for the year ending March 31, 2025. Insight, Atomico, 11.2 Capital, Coatue, Tiger Global, and Bessemer Venture Partners back the company.
- MNTN, an Austin-based TV advertising software provider, raised $187 million in an offering of 11.7 million shares (28% secondary) priced at $16 on the NYSE. The company posted $246 million in revenue for the year ending March 31, 2025. Baroda Ventures, Mercato Partners, Greycroft, Qualcomm, MGD Holdings, Bonfire Ventures, BlackRock, Fidelity, Peak Investment Holdings, Sylvina Capital, Anna McMurphy, Brederode, Dogwood Acquisition, George Dewey, IAG Capital Partners, Marwan Soghaier, Mohammad Hassan Afkham-Ebrahimi, and Staley Capital back the company.
- Voyager Technologies, a Denver-based defense and space technology company, filed to go public on the NYSE. The company posted $148 million in revenue for the year ending March 31, 2025. Dylan Taylor backs the company.
Funds:
- QuantumLight, a London-based venture capital firm, raised $250 million for its first fund focused on AI, Web3, fintech, SaaS and healthtech companies.
- Munich Re Ventures, the San Francisco-based venture capital arm of Munich Re Group, raised $125 million for its fifth fund and second fund from HSB focused on built world startups.
- Creator Ventures raised $45m for its second fund
- Factorial Funds, a Menlo Park, Calif.-based VC firm, raised $200m for its second institutional fund, with Hyundai Motor and Kia Corp. as anchor LPs
- Scribble Ventures raised $80m for its third fund.
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The material presented on Molly O’Shea’s website are my opinions only and are provided for informational purposes and should not be construed as investment advice. It is not a recommendation of, or an offer to sell or solicitation of an offer to buy, any particular security, strategy, or investment product. Any analysis or discussion of investments, sectors or the market generally are based on current information, including from public sources, that I consider reliable, but I do not represent that any research or the information provided is accurate or complete, and it should not be relied on as such. My views and opinions expressed in any website content are current at the time of publication and are subject to change. Past performance is not indicative of future results.