The Intentional Investor #27: Daryl Fairweather

From bagpipes to bouncing to betting markets, Andrew Mack’s journey to becoming a successful trader and sports bettor is anything but conventional. In this deeply personal and wide-ranging conversation, Andrew opens up about the detours, doubts, and decisions that shaped his unlikely path from rural Canada to algorithmic trading. Along the way, he shares what working in oil fields, selling used cars, and studying sociology taught him about risk, discipline, and finding conviction in uncertainty. This is a story about reinvention, self-reliance, and the grit it takes to build your own edge from scratch.

In this episode of The Intentional Investor, Matt Zeigler sits down with Andrew Cohen, a former market maker at Bernie Madoff’s firm whose life took a dramatic turn when the largest Ponzi scheme in history unraveled. But this isn’t just a story about scandal—it's about resilience, reinvention, and redefining success on your own terms.

In this captivating episode of The Intentional Investor, Matt Zeigler sits down with Kris Abdelmessih, the mind behind Moontower. From his immigrant family upbringing in New Jersey to becoming a seasoned market maker who covered virtually every trading pit imaginable, Kris shares his fascinating journey through the financial world. Learn how key mentors, family influences, and pivotal life moments shaped his path from trading floors to becoming a respected financial writer.

In this episode of The Intentional Investor, Matt Zeigler sits down with Brent Kochuba, founder of financial research firm SpotGamma. Brent shares his remarkable journey from network administrator to options trading expert, including his experiences at major financial institutions, surviving market crashes, and ultimately building his own successful derivatives research business. With humor and candor, Brent reveals the unexpected paths that led him to where he is today, including family influences, career pivots, and seizing opportunities during uncertain times.

Join Matt Zeigler on The Intentional Investor podcast as he interviews Daryl Fairweather, Chief Economist at Redfin and author of the new book "Hate the Game: Economic Cheat Codes for Life, Love, and Work." In this engaging conversation, Daryl shares her journey from MIT to the University of Chicago, her experiences navigating corporate America, and how she applies economic principles to everyday life decisions. With her unique background spanning academia, tech, and real estate, Daryl offers fascinating insights on using economic frameworks to understand human behavior and make better decisions.

Join host Matt Zeigler as he interviews Danika Waddell, founder of Xena Financial Planning, in this engaging conversation about career pivots, financial independence, and creating a more inclusive financial services industry. Danika shares her journey from accounting to launching her own financial planning firm during the pandemic, and how her personal experiences shaped her mission to help women in tech achieve financial independence.

In this episode of The Intentional Investor, host Matt Zeigler sits down with Cullen Roche, an economist, writer, and financial maverick who has carved out a unique space in the world of finance through his independent thinking and unconventional approach. From his large Irish Catholic family to his journey through finance, Cullen shares an intimate look at how curiosity, non-conformity, and a commitment to understanding complex systems have shaped his professional and personal life.

In this profound follow-up conversation, Matt Zeigler welcomes back Ben Hunt to explore the evolution of Hunt's writing and worldview. Beginning with reflections on their childhood relationships with religion and storytelling, the discussion moves into Hunt's journey with Epsilon Theory – from its market-focused origins to his current philosophical crossroads.

Kevin Muir, author of the Macro Tourist newsletter and a seasoned trader, joins The Intentional Investor for a fascinating conversation that weaves together trading, life lessons, and Canadian culture. From his early days mastering Monopoly statistics to pioneering computer-driven trading strategies at RBC in the 1990s, Kevin shares candid stories about finding his path in finance. Kevin discusses growing up as the older brother of a professional hockey player, his journey from discount brokerage manager to institutional trading desk, and how becoming a father changed his perspective on risk and career. He offers unique insights into market psychology, friendship, and the importance of finding work you genuinely love.

In this engaging episode of The Intentional Investor, host Matt Ziegler interviews Eric Markowitz, exploring his fascinating journey from investigative journalism to investment research. The conversation weaves through Eric's formative years, professional evolution, and life-changing experiences, offering valuable insights into the intersection of media, investing, and personal growth.