#170 - The Get Rich Slow Strategy for Passive Investors with Jeremy Roll

Tait Duryea and Ryan Gibson sit down with veteran passive investor Jeremy Roll to discuss building wealth beyond traditional stocks and 401(k)s. Jeremy shares how more than two decades of alternative investing shaped his approach to market cycles, diversification, liquidity, and passive cash flow. They also discuss preparing for market corrections, creating life-changing income through a “get rich slow” strategy, tax advantages of alternative investments, and managing dozens of K-1s. For pilots looking to build additional income without relying entirely on the stock market, this episode offers a long-term investor’s perspective.

Jeremy Roll is the Founder and President of Roll Investment Group and a longtime passive investor in real estate and private businesses. Before becoming a full-time investor, he spent more than a decade in the corporate world, including roles at Disney and Toyota, and earned his MBA from The Wharton School. Jeremy is also a co-founder of For Investors By Investors (FIBI), a nonprofit investor education and networking community. Known for his disciplined, research-driven approach, he has participated in more than 200 managed investments over his investing career.

Show notes:

(0:00) Intro

(2:28) Jeremy Roll’s investing background

(4:21) Investing through market cycles

(7:21) Preparing for a market correction

(11:43) Market concentration and margin debt

(16:34) Diversifying beyond the 401(k)

(18:59) Building life-changing passive income

(23:38) The get rich slow strategy

(26:30) Tax advantages of alternatives