Reflections on a Year of Change: Family, Startup, Portfolio Changes, and a New Book
After a whirlwind year, I am back to Substack and more. By Benjamin Tan
It has been quite some time since my last post on October 24, 2023, when I reiterated my confidence in Spotify (SPOT 0.00%↑) following their Q3 results. Back then, Spotify’s share price was under $160, and now it is on the brink of breaking $400—a gratifying development.
In the summer of 2022, I shared three picks that I believed could become the next Amazon and Spotify (SPOT 0.00%↑) was one of them. The other two were Palantir PLTR 0.00%↑ (picked by my friend John Nardi, who made an excellent call) and Block (SQ 0.00%↑), which is still grappling with slower growth in its merchant segment.
Looking back, I wish I had followed John’s lead on Palantir PLTR 0.00%↑!
Portfolio: Then and Now—A Shift Toward Stability
As a Type Five, I know I can be wrapped up in my head and get swayed by insular thinking. My worst investment mistakes have been in the small to mid-cap sector, representing the greatest allure to my intellectual side, which wants to beat the market. There, I get excited by the idea of uncovering the next big thing and frequently ignoring (or underestimating) the immense execution risks that come with trying to crossing the chasm. Maturing into an established business—think Starbucks (SBUX 0.00%↑) and ServiceNow (NOW 0.00%↑)—is a gravity-defying act that only a few can manage. Many do not make it.
When my husband and I decided to purchase a larger home late last year, it became a forcing function to reassess my portfolio. Sky-high mortgage rates made it clear that we would need to reduce borrowing, which meant selling some stocks to fund the purchase. That decision led me to re-balance my portfolio toward a more concentrated, large-cap approach.
So, walking the talk, I let go of several small-cap names to release funds and concentrated my portfolio on larger companies.
Small-cap positions sold in late 2023 and early 2024 include:
Elastic (ESTC 0.00%↑)
Sprout Social (SPT 0.00%↑)
Trupanion (TRUP 0.00%↑)
Endava (DAVA 0.00%↑)
In hindsight, selling some of these small-cap names felt like dodging a few bullets, especially with stocks like Endava (DAVA 0.00%↑) and Sprout Social (SPT 0.00%↑), which I exited near their highs. On the other hand, selling Trupanion (TRUP 0.00%↑), a position I had held well before the pandemic and has since doubled my disposal price, felt painful.
Ultimately, shifting my focus to a smaller group of larger-cap, proven names—and balancing this with increased homeownership—was compelled by a mix of lifestyle choices and a growing recognition of my biases as a Type Five investor. I still hold some smaller companies outside of the S&P 500, but with a more cautious approach to avoid the intellectual allure these stocks can have for my personality.
I will continue to share insights on managing portfolio changes, specifically how to recognize and mitigate biases, blind spots, and mental traps associated with personality-driven investing.
Startup, Family, New Home, Non-Profit, and…
Since mid-last year, life has introduced me to exciting new roles and responsibilities. I co-founded Psyntel, a mental health software company, with my good friend Sam Fargo, whom I got to know through my writing endeavors. At Psyntel, we are working to bring AI-driven insights to the mental health field, and we are thrilled to be approaching our commercial launch in the coming weeks.
On another front, I joined P.E.A.C.E, a non-profit that offers pro bono therapy to Asian Americans and Pacific Islanders in Georgia. Initially, I started as a volunteer advisor and recently joined the board. Our work in the AAPI community is incredibly fulfilling, providing meaningful ways to support those in need.
And perhaps the biggest change: On February 4, 2024, I became a father through gestational surrogacy. It has been a transformative journey, and I am immensely grateful for this experience.
…an Upcoming Book!
In the early days of 2021, I first considered writing a book—and I am thrilled to share that this vision is coming to life. My debut book, Suit Yourself, is set to be published by Köehler Book in the fall of 2025. The book will explore personalized investing strategies through the Enneagram, blending finance, psychology, and practical insights to help readers find an approach that reflects their true selves. This is a passion project and I am excited to bring this closer to fruition.
Stay tuned for more updates!
Conclusion
As I step back into sharing my thoughts here, I am excited to bring a renewed focus and share how my perspectives—and portfolio—have evolved. Whether it is refining my Type Five approach to investing, managing new roles in family and business, or preparing for the release of Suit Yourself, each step has been a learning experience. I hope to bring you along on this journey, sharing insights that combine personal finance, psychology, and tech investing.
I look forward to reconnecting with you all here and in future posts, which will be monthly and at the start of each month. Be sure to subscribe and follow along as I share portfolio updates, reflections on my investing mindset, and, of course, previews of my upcoming book!
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