Leigh Marie Braswell likes a game of risk, particularly if it’s a game of math.

Braswell grew up in rural Alabama, and wasn’t introduced to poker until she was an undergrad at MIT. And it wasn’t until she was an intern at Jane Street, the famed quantitative trading firm, that she was hooked on the game.

“We didn’t go out and party in New York—we stayed in and played poker,” said Braswell. “So, that’s how I really learned by playing every day against people at Jane Street.”

Braswell immediately joined the MIT Poker Club, where she reunited with Alexandr Wang, who she’d first met at a competitive math competition in her junior year of high school. Braswell went on to be an early employee at Scale AI, at the time knowing nothing about venture capital. 

“I barely knew what VC as a concept was,” she remembers. “Alex told me ‘oh, we’re signing a Series A term sheet.’ And then I went off and Googled: ‘What’s a Series A term sheet?’”

Braswell, now a partner at Kleiner Perkins, may be an unlikely VC, but her path to venture was built slowly and then all at once. She started angel investing in 2020, her last year at Scale: Her first check was into Ambience Healthcare, now valued at $1.1 billion. After more than two years at Founders Fund, Braswell joined Kleiner, a legendary firm in the midst of a turnaround led by Mamoon Hamid and Ilya Fushman. I spent more than six months getting to know the team at Kleiner, including Braswell, to tell the story of that turnaround (a 3,600-word feature published this past weekend). And Braswell repeatedly came up as someone who’s a rising star, not just at Kleiner, but in VC. 

Why? It’s simple: Braswell has been a key investor behind some of the buzziest AI deals that materialized in 2025. At Kleiner, she backed Windsurf (an Alphabet acquihire) and Neon (acquired by Databricks), and her Founders Fund deal to back Chronosphere ultimately saw the company acquired by Palo Alto Networks. (Yes, 2025 was a big year for Braswell, who’s been in VC for six years if you squint, an industry where often people are successful with one or two real exits after a decade.)

Braswell—whose current Kleiner portfolio includes Nooks, Convoke, Reevo, Avoca, and Forge—doesn’t exactly consider herself an AI investor, though. 

“I do describe myself as relatively generalist,” she said. “However… you definitely want to have unfair advantages, or pools of certain people and networks that you’re really in. And when you look at those networks of people—especially these days and with good reason—that’s ideally in and around AI.”

Braswell had started hosting regular poker nights with Wang while she was at Scale, and she still does—over time, they’ve become a piece of her investing strategy. It’s a recurring way to source deals, build founder relationships, and help portfolio companies hire. But it’s also a mindset. 

Because in the end, poker’s about tracking probabilities and making decisions with incomplete information, much like early-stage investing. And though there may be things you can’t know, you can know your odds. 

“The core lesson from poker,” said Braswell, “and it’s something I’m grateful for as a VC: If the odds are in your favor, you push your chips to the center.”

Read the entire feature on Kleiner Perkins’s past, present, and future here.

Exclusive…TRM Labs, a blockchain analytics firm that builds crime-fighting software for government agencies and the private sector, raised a $70 million Series C valuing the startup at $1 billion. You can read all about it here.

Term Sheet Podcast… The Term Sheet Podcast is back this week, and our latest guest: Kristina Shen of Chemistry. In 2024, Shen left her role as a general partner at Andreessen Horowitz to start new VC firm Chemistry with Mark Goldberg and Ethan Kurzweil. Kristina and I talk about starting a VC firm from scratch, how she thinks about AI revenue, and healthcare. Watch and listen here.

See you tomorrow,

Allie Garfinkle
X: @agarfinks
Email: alexandra.garfinkle@fortune.com
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VENTURE CAPITAL

- Skyryse, an El Segundo, Calif.-based developer of aviation automation technology, raised $300 million in Series C funding. Autopilot Ventures led the round and was joined by Fidelity Management & Research Company, ArrowMark Partners, Atreides Management, BAM Elevate, Baron Capital Group, Durable Capital Partners, and others.

- Tomorrow.io, a Boston, Mass.-based weather modeling company, raised $175 million in funding. Stonecourt Capital and HarbourVest led the round.

- Ares Interactive, a San Francisco and Berlin, Germany-based game developer, raised $70 million in Series A funding. General Catalyst led the round and was joined by others.

- Alaffia Health, a New York City-based agentic AI platform designed to manage health plan claims, raised $55 million in Series B funding. Transformation Capital led the round and was joined by FirstMark Capital, Tau Ventures, and Twine Ventures.

- Lotus Health AI, a San Francisco-based developer of an AI doctor platform, raised $35 million in Series A funding. CRV and Kleiner Perkins led the round.

- ORION Security, a New York City and Tel Aviv, Israel-based AI-native data security company, raised $32 million in Series A funding. Norwest led the round and was joined by IBM and existing investors.

- Avalanche Energy, a Seattle, Wash.-based fusion energy company, raised $29 million in funding. RA Capital Management led the round and was joined by 8090 Industries, Overlay Capital, and existing investors.

- Veremark, a London, U.K.-based background screening, whistleblowing, and credential verification platform for workplaces, raised $26 million in Series B funding. Gresham House Ventures led the round and was joined by others.

- Pasito, a New York City-based AI-native employee benefits platform, raised $21 million in Series A funding. Insight Partners led the round and was joined by Y Combinator and MTech Capital.

- Synthpop, a Cambridge, Mass.-based agentic AI platform designed to automate health care workflows, raised $15 million in Series A funding. Ansa Capital led the round and was joined by others.

- Breezy, a Los Angeles, Calif.-based AI operating system designed for residential real estate professionals, raised $10 million in pre-seed funding. Ribbit Capital led the round and was joined by Fifth Wall, DST Global, Liquid 2 Ventures, and others.

- enclaive, a Berlin, Germany-based cybersecurity company, raised €4.1 million ($4.8 million) in seed funding. Join Capital and the Amadeus APEX Technology Fund led the round and were joined by Auriga Cyber Ventures.

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PRIVATE EQUITY

- AEA Investors acquired a majority stake in Magna5, a Canonsburg, Pa.-based provider of managed IT, cybersecurity, and cloud-based services. Financial terms were not disclosed.

- Arax Investment Partners, backed by RedBird Capital, acquired GFP Private Wealth, a Cleveland, Ohio-based investment advisor. Financial terms were not disclosed.

- Pendo, backed by Thoma Bravo, acquired Chisel Labs, a San Francisco and Pune, India-based AI-powered platform designed for product management teams. Financial terms were not disclosed. 

- Skyline Investors acquired Buddy’s Home Furnishings, an Orlando, Fla.-based furniture, electronics, and appliances retailer. Financial terms were not disclosed.

EXITS

- Littlejohn & Co. acquired 80/20, a Columbia City, Ind.-based provider of configurable, modular framing solutions, from MPE Partners. Financial terms were not disclosed.

 - Vivo Capital agreed to acquire Dutscher Group, a Bernolsheim, France-based consumables and equipment distribution company for R&D laboratories, from LBO France. Financial terms were not disclosed.

IPOS

- ARKO Petroleum, a Richmond, Va.-based energy distributor, plans to raise up to $210 million in an offering of 10.5 million shares priced between $18 and $20. ARKO Corp. backs the company.

FUNDS + FUNDS OF FUNDS

- Otro Capital, a New York City-based private equity firm, raised $1.2 billion for its first fund focused on companies in the sports ecosystem.

PEOPLE

- ATL Partners, a New York City-based private equity firm, promoted Lauren DiBartolomeo to chief operating officer. The firm also promoted Josh Raj and Daniel Wu to vice president.

- Vista Equity Partners, an Austin, Texas-based private equity firm, hired Suzanne Donohoe as chief operating officer and chief commercial officer.