3 Things I’ve Learned From Women in VC

Especially as a Woman Lawyer Turned VC.

Sylvia Kim
Startup Grind
8 min readSep 14, 2020

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Photo Courtesy of Valentina Conde on Unsplash

I am a lawyer by trade and an advocate by nature. But after 15 years of working in law, policy, and advocacy, I recently made a major career pivot and joined the world of venture capital.

Both the world of law and VC have similarities; both are generally quite hierarchical and male-dominated with ongoing aspirations to better represent the diversity of the communities they serve. But so many of my interactions with fellow lawyers have always had an inherently transactional or adversarial tone while I have received nothing but affirmation and encouragement — even with my non-linear journey into VC — from those I have interacted with in the world of VC.

This has been especially true in my interactions with fellow women.

Women in Law

It really wasn’t until I had my first job out of law school — a coveted articling position at a prestigious criminal appellate firm — that I first experienced this strange world where women were the ones I wanted to avoid most. Whether it was opposing counsel, partners, or judges — it was the women who were harshest and most unforgiving; the ones who always ended up making you want to cry.

Of course, not all my interactions with fellow women lawyers have been negative and the cattiness, so commonly seen in female interactions, may have been amplified in the adversarial world of criminal litigation. I’m still unsure if my experiences were unique to the criminal law context in Toronto back in the late 2000s; a world in which I was too often the only woman of color in the room and repeatedly mistaken for administrative staff…both in my firm and in the courtroom.

Even when I left criminal litigation and moved to the US, my interactions with fellow lawyers have always had a certain wariness. Perhaps it is the hierarchical nature of the legal profession or the constant sizing up we all do to one another based on which law school, law firm, or networks we come from. To this day, a part of me still feels this reluctant feeling of deference when I speak to a senior partner or judge.

Although I’ve long left the world of law, I have had ongoing interactions with lawyers in many different capacities; some of my closest friends and most trusted professional mentors are all lawyers. But whether it is my residual trauma from many scathing adversarial encounters or not — I would never describe my interactions with lawyers as heart-warming or uplifting. Especially with fellow women lawyers.

I am now in my late 30s and have made several major career pivots — including a cross-country move with 2 kids in tow. By far, the most momentous pivot was the one I recently took from the nonprofit world of philanthropy to medtech venture. A series of personal and professional circumstances led me to search for the most impactful medical technologies and, in my new role, I am proud to invest in life-saving medtech ideas in order to turn them into vibrant commercial ventures.

Such a significant pivot requires a critical expansion of one’s professional network and as I sought to expand my network, I came upon the ‘Women in VC’ network —the world’s largest database of female venture investors with over 2,500+ global members.

Becoming a Woman in VC

It has now been over 3 months since I first joined the Women in VC network and I have had over 40 incredible conversations with some of the most inspiring, impressive yet genuinely kind and warmhearted women. Never before, in my professional career, have I been so encouraged and uplifted; I have walked away from some of these conversations totally blown away by the vision, the effectiveness, and the like-mindedness of fellow women who are seeking the most innovative and strategic ways to make a positive impact in our world today.

Photo Courtesy of Women in VC

It is no wonder the ‘Women in VC’ network is such a vibrant community — 2,500 strong and growing. I know law and VC are not completely analogous but having experienced a taste of this remarkable community where fellow women — no matter how senior or junior you are — actually want to help and connect, I am inspired to better embrace this professional intersection of being both a lawyer and a VC.

As I reflect on what it means to be both a lawyer and a VC — especially as a woman — here are 3 things I’ve learned from ‘Women in VC’.

1. Kindness is not a weakness (and being nice matters!)

Throughout my career, I’ve often viewed my natural tendency to be kind or nice as a weakness. Perhaps it is because of the many times I’ve been told, invariably by well-intentioned older women, to talk louder, to act more authoritatively, to smile a little less…to cover up my ‘niceness’ as a way to prep me for long days in the courtroom.

But, in my opinion, this tradition of ‘toughening’ up junior lawyers is becoming extinct; this type of archaic thinking perpetuates the very systemic behaviors that prevent women from reaching the upper echelons of the legal profession.

As I pivoted into the world of nonprofit and philanthropy, I was no longer told to cover up my niceness but the kindness I saw and experienced was often cloaked in expectation and a layer of artificiality. There always seemed to be some strings attached to any act of kindness received; kindness was just the tip of the spear and I was always wary of what came next.

Over the years, I’ve learned to embrace my natural disposition to be ‘nice’ by balancing it with an absolute intolerance for unethical behaviors (surprisingly much more common than what I expected of the nonprofit world) and an ability to unequivocally cut any ties in order to maintain my personal integrity and reputation.

However, my recent pivot into VC has astounded me with the amount and frequency of unabashed kindness I have received. In the world of VC, it appears that kindness is a strength that is distributed freely and openly. Indeed, I recently got plugged into a group called “VCs Who Care” and had one of the most authentic and vulnerable conversations I’ve ever had in a professional setting. Comparably, just last week, I met a veteran investor who, despite his many successes, told me how he kept himself grounded throughout his 20+ year career by following a mantra that was memorialized on a poster he had kept up in his office: “being nice matters”.

In a world where cutthroat aggression has become the norm in business interactions, what a humbling reminder that kindness is not a weakness! Kindness is a sign of humanity, of authenticity, of trust-filled interactions and relationships. So thank you to the fellow Women in VC, VCs Who Care, and all the other investors who have inspired me to embrace my natural disposition and to freely express kindness in all of my professional interactions…because ‘being nice’ truly does matter.

2. Pedigree and experience do not equate to the potential for impact

After many years of advocacy work, I can confidently say that our pedigree and years of experience do not always equate to our potential for impact. Of course, our education, background, and network can open doors and provide credibility — but innovation and impact often come from unexpected intersections and diverse perspectives who bring a fresh approach to an unresolved problem.

The Medici Effect is a good example of how the intersection of diverse disciplines and industries can lead to disruptive innovation. So not always following the usual pathways into law or VC is a good thing. I’ve seen this to be true with the Women in VC network who have accepted and embraced me with such open arms despite my ‘junior’ state in the industry. Somehow the transferability of my skills and experiences have been seen as an asset and as a greater potential for impact than my mere months of limited VC experience.

Additionally, our world — especially the world of innovation and technology — is not entirely hierarchical. You never know where your next big deal will come from and innovation seems to live more instinctively among the next generation of leaders.

It’s also important to remember that none of us will ever have an unlimited potential for impact; there is only a limited window during which we have the right skills, experience, and connections to actually make an impact. So let’s stop following the same old formulas or only going down well-trodden pathways. Let’s embrace our potential for impact instead of focusing on hierarchy, pedigree, or years of experience.

3. Take the time to listen and pay it forward

As I started connecting with women investors all over the globe, I started looking forward to these ‘intro’ calls where I would listen to such incredible stories and powerful journeys into the world of VC.

Some common themes definitely emerged: a communal struggle with imposter syndrome; the unspoken bond we all share as women in a male-dominated world; the strong and almost urgent desire to connect, to collaborate, and to provide value to one another.

As I heard story after story, I was constantly inspired to hear such passion, resilience, and a shared vision to make a positive impact in our world today. I realized how we all come from somewhere, we all struggle, we all strive and overcome. Taking the time to listen to these testimonies of success has really helped me to build genuine relationships as opposed to mere transactional encounters.

I was also constantly amazed by how these trailblazing general partners and managing directors were taking the time to connect with me and to hear my own story; they really took the time to ‘pay it forward’ and to encourage me as a novice VC.

Even as a ‘new’ VC, I am realizing that I am still in a privileged position to give back and ‘pay it forward’ to other women. I wonder how different my perspective and experiences would have been as a young lawyer had I also been encouraged to listen and to pay it forward.

Photo courtesy of All Raise

Ultimately, whether we are lawyers or VCs, women need to do a better job of championing one another.

In industries where we are often the only woman in the boardroom (or courtroom), we need to do a better job of raising one another up. I’m thus proud to be a part of All Raise’s inaugural Visionary Voices Speakers Bureau — another phenomenal testament to the ability for women in VC to mobilize and elevate one another.

After all, empowered women empower women. May we continue to reach greater heights of empowerment while uplifting and emboldening other women — no matter what industry we are in.

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