Iconoclastic Capital Management LLC

Jack Hills is a financial advisor at Iconoclastic Capital Management LLC with 10 years of industry experience. He holds a Series 66 designation and has worked at firms including Christopher Haigh, Northwestern Mutual Investment Services LLC, and Merrill. Hills has been with Iconoclastic Capital Management since 2020. Iconoclastic Capital Management provides discretionary investment management and modular wealth management and financial planning to individuals, high-net-worth households, trusts, and business owners. The firm uses an evidence-based, core-and-satellite investment approach featuring low-cost broad ETFs, active sleeves, and AI-driven tools with human oversight.

Gene Thompson Jr. is a financial advisor at Iconoclastic Capital Management LLC with 10 years of industry experience. He holds the CFP® and ChFC® designations and has previously worked at Northwestern Mutual and Northstar Money. Iconoclastic Capital Management provides discretionary investment management and modular financial planning services to individuals, high-net-worth households, trusts, and business owners. The firm employs an evidence-based, core-and-satellite investment approach incorporating low-cost ETFs and active sleeves, and offers specialized services including cryptocurrency advisory and coordinated tax-preparation support.

If you’re looking for a traditional advisor who wants to talk at you in a conference room for two hours and then sell you a product, we are probably not your firm. Iconoclastic Capital is a fee-only fiduciary financial planning and investment management firm with offices in Rochester and Brooklyn, NY. We work with high earners, business owners, tech professionals, startup founders, Gen X families, artists, creatives, and crypto investors who have outgrown generic advice. Most people come to us when their financial life has become too complex for YouTube, Reddit, or the advisor who “has a guy.” Equity compensation, business cash flow, tax planning, retirement projections, real estate decisions, insurance, estate planning, and crypto all have a way of colliding at the same time. Cute system. Our job is to turn that mess into a clear plan and then help execute it. We are true fee-only fiduciaries. That means our compensation comes directly from clients, not commissions, kickbacks, insurance sales, or product payouts. We are legally obligated to put your interests first, explain how we are paid, and give advice that is actually about you. Strange concept, apparently. What we help with: Comprehensive financial planning Investment management and portfolio strategy Cash flow and tax planning Business owner planning Retirement and income planning Equity compensation, RSUs, ISOs, and AMT planning Insurance and risk management reviews Real estate and major purchase decisions Crypto and digital asset planning Crypto is one area where we are especially different. Most advisors either panic when they hear “wallet” or pretend digital assets are magic internet money. We integrate crypto into real financial plans, including portfolio strategy, tax loss harvesting, cost basis tracking, estate access, custody, and risk management. If you need a crypto financial advisor who understands taxes, wallets, and risk, that is not a side quest for us. I’m Christopher Haigh, CFP®, RICP®, CEO and co-founder of Iconoclastic Capital. I started this firm because financial advice should be normal: clear, honest, useful, and built around the person sitting across from us. No product pitch dressed up as planning. No pretending complexity makes advice better. No ego trip. If you want a planning team that is direct, technically sharp, slightly allergic to industry nonsense, and serious about making you feel less alone with your money, we should probably talk.