ABOUT
About Benjamin Tan
Benjamin Tan is an investor and writer whose work explores the intersection of psychology and financial decision-making. He previously worked in investment banking at Credit Suisse and UBS in Singapore before relocating to London and later the United States.
Benjamin holds first-class honors in Accounting and a Master’s degree in Clinical Mental Health Counseling. He is a National Certified Counselor (NCC) and has also worked as a mental health technology entrepreneur, developing software tools for clinicians. His background in psychology, finance, and technology informs his writing on behavioral investing and the emotional forces that shape how people make decisions about money.
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Raised in a humble household in Singapore, Benjamin overcame numerous early challenges to achieve financial independence. His personal journey—from a cautious value investor to a more adaptive growth-oriented investor—forms the foundation of his debut book, Suit Yourself: A Portfolio Strategy for Every Personality Type.
Benjamin writes regularly about behavioral finance and investing psychology on Substack and Yahoo Finance. He also serves as a board member of P.E.A.C.E., a nonprofit promoting mental health within Georgia’s Asian American and Pacific Islander communities. His work helps investors understand how their own psychology shapes the decisions they make in the market.
How Suit Yourself Came to Life
Suit Yourself was born out of Benjamin's unique intersection of expertise in personal finance, psychology, and the Enneagram. As someone who has evolved from an introverted, risk-averse individual into a confident investor, Benjamin found that understanding personality types—his own and others—was the key to unlocking better investment strategies. He combined this personal journey with his knowledge of human psychology and years of observing how different personalities approach risk-taking throughout the writing process. Beyond financial advice, Benjamin wanted to honor readers' individuality and infuse his book with humor and pop culture references.
The result is Suit Yourself, a book that offers personalized roadmaps aligned with the inherent strengths of each personality type and helps readers overcome the pitfalls created by unconscious biases.
If you are curious about the book, you can start here. The preview includes the introduction and a chapter about my investing journey.
My Type Five Personality:
An Ongoing Evolution A Note from the Author
Growing up in Singapore, I learned early on the importance of independence and self-reliance. Raised by my paternal grandmother and extended family, I developed a strong Type 5 personality—what the Enneagram calls "The Investigator." This made me naturally curious, analytical, and intensely focused on understanding the world through knowledge and careful observation.
As a Type Five, my instinct was always to gather information and minimize risks before making decisions. I played it incredibly safe when I started investing, focusing exclusively on government treasuries. There was a real fear of taking risks, and I found comfort in the predictability of low-yield investments. My analytical nature sometimes kept me from seeing the potential rewards of taking calculated risks. But over the years, I have evolved.
My journey in personal investing has directly reflected my growth as an individual. As I gained more experience and confidence, I embraced new perspectives. I slowly expanded my portfolio beyond treasuries, seeking a balance between new learnings, higher returns, and measured prudence. This was not an overnight change but a gradual pivot towards being more open-minded. Looking back, I adopted traits from other Enneagram types, particularly Type Seven (The Enthusiast) and Type Eight (The Challenger), as predicted by the Enneagram model. Like a Type Seven, I started to embrace the joy of exploring new investment opportunities, and like a Type Eight, I became bolder and more assertive in my decision-making. My portfolio reflects this personal evolution—I still value careful analysis but am much more comfortable taking calculated risks.
Suit Yourself grew out of this personal journey. I realize the importance of understanding one's inherent strengths and weaknesses when investing. Knowing my Type Five tendencies has helped me develop a strategy that leans into my natural strengths and mitigates blind spots while developing new traits when necessary. In the book, I explore how each Enneagram type can find its unique path to financial success, just as I have.
Podcast Interview: October 2025
Benjamin appears on Do It For The Gram: An Enneagram Podcast, hosted by Milton Stewart. In this wide-ranging conversation, they explore the intersection of personality, money, and meaning—anchored in Benjamin’s book Suit Yourself: A Portfolio Strategy for Every Personality Type. From growing up in Singapore under restrictive norms to applying Enneagram insights to portfolio construction, Benjamin shares how psychology and investing are deeply intertwined.
Media Interview: August 2025
Benjamin shares with journalist Jane Wollman Rusoff how investors’ Enneagram personality types—such as the Perfectionist, Achiever, and Investigator—can shape their financial behavior and decision-making styles. The discussion highlights key insights from Suit Yourself and how advisors can better understand their clients by tuning into their personality dynamics.
Read the interview here
Podcast Interview: June 2023
Check out Benjamin's interview on The Investing for Beginners Podcast. Host Dave Ahern and Benjamin talk about their respective Enneagram types and how personality traits have influenced their investing behaviors in the past.