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  • Gail Wong

My First Year of Women Investing in Women (Part 1 of 3)

Updated: Nov 24, 2023

Working alongside women at Ladies Investment Club (L.I.C.) and SheEO crystallised a reinvented personal investment philosophy - one that integrates emotions, beliefs, purpose, and values.


When people learn I spent a decade on Wall Street as an Investment Banker, they automatically presume investing comes naturally.


While I had an illustrious career advising on >$10Bn of corporate finance transactions at a white-shoe firm - developing "brain-damage" level financial modelling skills along the way - I only fully owned being an investor after unlearning certain "rules" of the investing game:

  • maximise financial returns;

  • winner takes all;

  • don't trust anyone; and

  • there is no room for feelings.

Fairly, or unfairly, I associate this dispassionate approach to investing/business with men. 90% of the people I worked with at Morgan Stanley - clients, colleagues and bosses - were men. (In the UK/US, white men, and in Asia, Chinese men. But this Privilege conversation is for another day.) They were my teachers, role models, and controllers of my destiny. Even after leaving banking, the overwhelming majority of my investment discussions were with men.


2017 was when I consciously stepped away from this investing paradigm, and evolved a new personal investing philosophy. I don't think it's a coincidence that I started being almost exclusively around women.

  • Day 1 in 2017, I took charge of my family's investment portfolio.

  • Through 2017, I transformed my relationship with money, risk, and uncertainty, and created a proprietary coaching program guiding other women to do the same.

  • Discovered gender investing, embraced the SheEO model and got involved at L.I.C. (eventually becoming a co-founder) in late 2017.

  • In 2018, L.I.C. invested in 3 female-led businesses, reviewed 16 others, and currently engaging 2 live opportunities. Our membership base grew 3-fold, and we hosted 2 female entrepreneurship panels. SheEO Founder Vicki Saunders introduced SheEO to Singapore where awareness is growing, and I activated for SheEO Australia.

As a leader actively engaged across all initiatives, I've had both bird's eye view, and up-close-and-personals with business founders and community members, from which I'll share 4 lessons over 3 articles.


Lesson 1: Believe in Yourself.


I have to start with my personal investing journey. Looking up from a 5-year vortex of parenting young children to an economic landscape of "blockchain," "AI," "Belt Road initiative" was humbling. It helped that 2017 markets were kind to everyone - I got room to formulate, test and validate my personal thesis.


My biggest discovery?

Investing with all parts of oneself - head, heart, gut - aligned is rather extraordinary and (shocker!) joyful.

Some victories:

  • followed a single stock, trading it twice to generate 20% each time;

  • concentrating positions I had both knowledge and conviction in, instead of trying to catch the latest trend (cough, crypto);

  • choosing long-term themes over short-term upside opportunities with bragging rights;

  • keep moving when one decision didn't work out.

You will lose some. And it's OK.

How does fear and self-doubt come in? They can be very helpful if you lean into it: examine your questions; articulate your fears; respond consciously. I spent as much time researching markets, as working internally to be free of past, and build resilience through volatile markets.


The cautionary phrase "Past performance may not be indicative of future results" can be a helpful reminder: keep self-judgment and "should have"s about past investment decisions out of your future-oriented decision making.


Besides, that judgment can change like the wind. At different points of 2018, one single bet might show a very different performance.


If 2017's investing journey was about establishing individual performance, 2018 was about doing it alongside others, being curious about their views, and integrating perspectives. Read on for Lessons 2/3 and the final part of this series.


If you enjoyed this, please share the article with others who might benefit. I'd enjoy hearing your feedback/ questions via PM.

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