Every venture capitalist needs capital, too. Samir Kaji’s podcast and newsletter examine the less glamorous decisions that turn an investor into a fund manager.

His parents trusted their union pensions. Nearly three decades into a career at HarbourVest, John Toomey is asking what it takes to bring that same investment discipline to a much wider public.

At Centricity WealthTech, the founding member and investment product head works amid an expanding menu of investments. His public arguments keep returning to a quieter question: what belongs in a particular portfolio?
Independent advisors wanted private markets. What they lacked was the institutional plumbing. CAIS spent 17 years assembling access, diligence, education and paperwork into one operating system - and turned the boring middle into a company valued above $2 billion.

An accountant turned asset-management operator spent decades learning where good investment teams get stuck. His answer was North Square - a bridge between boutique managers, financial advisers, and the portfolios they are trying to improve.
Prime Quadrant started after one family discovered that a liquidity event can buy almost anything except unbiased advice. Now the firm serves more than 260 families, caps the roster near 300, and wants to manage the arguments around wealth as carefully as the assets themselves.
Two Chicago traders spent a decade turning hedge-fund tactics into a wealth business for families who aren't endowments. In 2026 they sold it - $5.6 billion later.

Before financial AI became a category, Scavo had already spent two decades moving between code, markets and data. Streetbeat is his attempt to turn that unusual apprenticeship into an agent that can make financial work less manual - without pretending judgment has disappeared.
iCapital is a New York-based financial technology platform that opens private-market and alternative investments - private equity, hedge funds, private credit, real estate, structured investments and annuities - to wealth advisors and their high-net-worth clients. Founded in 2013, it replaced the paperwork-heavy, high-minimum world of alternatives with an end-to-end digital infrastructure connecting asset managers and wealth managers, and now services more than $1 trillion in client assets across 2,100-plus funds for roughly 118,000 financial professionals.

Taylor Pearson is the CEO and co-founder of Mutiny Fund, a multi-strategy long volatility and tail-risk hedge fund whose sub-advisors manage over $10 billion in client assets. Before building Mutiny, he wrote 'The End of Jobs' (2015), an Amazon #1 bestseller translated into five languages that argued entrepreneurship had become safer than employment. He runs 'Interesting Times,' a monthly newsletter for 27,000+ founders, investors, and executives exploring complex systems, finance, and the future of work. A former college football offensive lineman who once marched for Bolivian workers' rights in Argentina, Pearson cold-called his way into digital marketing at minimum wage before buying a software company and eventually co-founding a hedge fund - all while living across eight countries.