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  • Gail Wong

My First Year of Women Investing in Women (Part 2 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.


This article is a continuation to the Introduction/ Lesson 1 and covers Lessons 2 and 3.


If 2017's investing journey was about establishing individual performance (mostly to myself), 2018 was about doing it alongside others, being curious about their views, and integrating perspectives. In addition to public markets, I personally reviewed over 25 angel/ seed financing private opportunities, and engaged primarily with female investors.


At this early stage of business existence, one's investment is essentially in the person/ people behind the idea. Given my wholistic coaching philosophy, I am always keen to understand the complete picture of a business leader.


Lesson 2: Human Beings, First.


I've found myself incredibly inspired by business owners who are human beings, first. They care, and not only because they could be handsomely paid to. They recognise that their business' value is in the hands of their people, and pay attention to this.


They care about hiring inclusively, paying fair wages, using sustainable resources, giving back, while altering humanity with innovations and of course, making money. An enlightened CEO I met this week pointed out that her business can only create lasting impact if it stays alive. Others I've met would not choose entrepreneurship as a living, if not for a mission that had to be served.


Such a refreshing departure from Wall Street, where it seemed that non-financial factors were a waste of time, distraction for management and seen as a threat to returns.


Operating in a crowdsourced environment revealed to me how much of the competitive, scorched-earth approach was unconsciously buried in my financial decision-making. I’ve unlearnt some aspects of the supposedly-hallowed financial training that don’t leave room for humanity - e.g. Growth at all costs/ Emotions are bad.


I realised that for years, I had opened pitch decks with a default skepticism. Perhaps I have heightened appreciation for this since I've started running my own business - the courage to ask is the only way to cause change. Shelving the vestiges of the "every man for themselves" mentality, I welcome Founders with equally open heart. Transparency of intention is one trait that catches my attention as an investor.


Lesson 3: Then, Relationship.


While track record, leadership, motivation and grit are important criteria, the Investor-Founder Relationship is paramount. The care and emphasis that Relationship has been discussed in the all-women deals I've been part of is quite exceptional.


And this is a two-way street. Trust and support open up a channel for invaluable influence/ advice and leverages investor resources. It can be turnkey to shaping a business' trajectory and return, to the extent of opening a whole new business segment for one such portfolio company.

  • At L.I.C., we have leveraged our collective membership's networks to introduce investee companies to new clients, hires and capacities

  • SheEO amplifies this effect with a 1:100 Venture-to-Activator ratio and a core culture of Radical Generosity

Underpinning it is the belief that it's possible for everyone in the relationship to enrich themselves abundantly.


It also makes a difference to the CEO who champions a disruptive or purpose-driven enterprise to know there are people in their corner, sharing their vision of the world, however great the gap to reality today. Where capital is plentiful, Relationship is a clear differentiator.


The Relationship also lays the groundwork for any discussions that might be deemed "difficult." For example, understanding hard limits, creating compromise on deal terms, making the case for valuation. The dynamic of "We" alters the flavour of such conversations.


Two final points I'll say here on the topic of human beings:

  1. Vision, track record and leadership is usually evident but even CEOs with all three attributes talk, think, and cry in their unique way. I encourage any CEO pitching to honour their whole self, even as the financing community's expectations of a "dream CEO" converge. Currently, there is a rising movement encouraging Founders to question raising lots of venture capital as a default "must-do".

  2. On top of hard skills and purpose, I pay attention to whether a person is set up to succeed sustainably. I often say,

Entrepreneurship is the Olympics of Uncertainty

Are the Founders we invest in nurturing their whole self - health, mind, spirit - for peak performance in the long haul? Are they taking care of themselves in the simplest of forms? How would they define success for themselves? Try finding this criteria in a due diligence checklist!


If this investment approach strikes you as uncharacteristically heavy on soft factors, I urge you to read on for Lesson 4 where I offer my view on how it all hangs together.


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

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