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Nathan McCauley and the trouble with keeping the keys
Lost crypto keys gave Nathan McCauley a business idea. Turning it into Anchorage Digital meant learning that securing money and earning trust require more than good code.
Joe Robinson and the art of getting people together
Before he co-founded Hummingbird, Joe Robinson brought designers and technologists into the same room. His work in financial-crime investigations keeps returning to a familiar problem: helping people, information, and tools work together.
Jeff Kolovson and the Business of Making Risk Disappear
Before Faire could connect shopkeepers and brands across borders, its co-founder learned operations the blunt way: sixty futons, thirty-six hours, and no room for excuses.
Jacqueline Reses
Jacqueline 'Jackie' Reses is the Chair and CEO of Lead Bank, a Kansas City-based chartered bank she acquired in 2022 and transformed into a banking-as-a-service powerhouse serving fintech builders. Previously, she built Square Capital from zero into a multi-billion dollar lending business at Square (now Block), served as a board member at Alibaba through its historic 2014 IPO, led 41 transactions as Yahoo's Chief Development Officer, and spent seven years at Goldman Sachs in M&A. A Wharton-trained economist from Atlantic City, she co-authored 'Self-Made Boss' and holds patents in payments, credit, and cryptocurrency. Lead Bank closed a $70M Series B in September 2025 at a $1.47B valuation backed by a16z, Ribbit Capital, Coatue, and Khosla Ventures.
Brett Browman
Brett Browman is a Growth Operating Partner at Khosla Ventures, bringing a hands-on, ER-doctor approach to diagnosing and scaling portfolio companies. A veteran of Silicon Valley's most storied growth stories - first growth hire at both Square and Opendoor - he spent seven years as Operating Partner at Andreessen Horowitz advising companies like ElevenLabs, Character.ai, and Luma.ai before joining Khosla in 2024. Known for getting in the trenches as a fractional growth leader, Browman has helped shape the go-to-market playbooks of some of the fastest-growing startups in tech history.
Rob Hayes
Rob Hayes is a Board Partner at First Round Capital, the seed-stage venture firm famous for backing companies before anyone else dares. Over 12 years as a full partner beginning in 2006, Hayes made some of the most consequential bets in tech history - writing the first institutional check into Uber when it was worth $4 million, backing Square before payments were cool, and leading investments in Mint.com, eero, Planet Labs, and Gnip. A former Palm product manager turned Omidyar Network pioneer turned VC legend, Hayes built First Round's San Francisco office from scratch and helped define what 'founder support' actually means in venture capital.
Jim McKelvey
Jim McKelvey is the co-founder of Square (now Block, Inc.), a serial entrepreneur, master glassblower, author, and philanthropist from St. Louis. He built Square after losing a $2,000 sale at his glass studio because he couldn't accept American Express - and turned that frustration into a payments company that beat Amazon when it tried to copy them. He's also founded Invisibly, co-founded LaunchCode (a nonprofit that guarantees tech jobs), serves as an Operator Advisor at Redbud VC, and is a former Chair of the Federal Reserve Bank of St. Louis.
Roelof Botha
Roelof Frederik Botha is a South African-American venture capitalist and former Managing Partner of Sequoia Capital, one of the world's most storied VC firms. Grandson of South African foreign minister Pik Botha, he rose from PayPal CFO at age 28 - overseeing the company's IPO and $1.5B sale to eBay - to become one of Silicon Valley's most celebrated investors. He wrote the original investment memo for YouTube when the company had 3 employees and a valuation of $11.5M; Google bought it 14 months later for $1.65B. Over two decades at Sequoia, he backed YouTube, Instagram, Block (Square), MongoDB, Unity, Natera, and dozens more, generating over $50 billion in returns for limited partners. He stepped down as Sequoia's Senior Steward in November 2025.
Keith Rabois
Keith Rabois is a PayPal Mafia veteran, co-founder of Opendoor, and Managing Director at Khosla Ventures whose career spans law clerk, corporate attorney, political adviser, and now one of Silicon Valley's most prolific — and outspoken — investors. He is the first institutional backer of DoorDash, Affirm, and Faire, made early bets on Stripe, YouTube, and Airbnb, and brought the iBuyer model to residential real estate before moving to Miami and catalyzing one of the biggest tech migration waves in recent memory.
Jack Dorsey
Jack Dorsey is the co-founder of Twitter and Square (now Block), a Bitcoin maximalist, and one of Silicon Valley's most enigmatic figures. He sent the first-ever tweet, built a payments empire, walked 5.3 miles to work daily, meditates two hours a day, eats once a day, and is currently obsessed with decentralizing everything from money to social media. His latest ventures - Bitchat (Bluetooth mesh messaging) and Block's Bitcoin treasury - reveal a builder who has moved far beyond the platforms that made him famous.