Meet Alicia Castillo Holley

We were lucky to catch up with Alicia Castillo Holley recently and have shared our conversation below.

Alicia, thank you so much for joining us. You are such a positive person and it’s something we really admire and so we wanted to start by asking you where you think your optimism comes from?

It is a combination. A bit part comes from an accident. I fell off a horse at 13 and ended up in a coma for few days. I remember watching myself dead on a hospital bed and feeling sorry for dying without living life. I woke up few days later and ever since I have felt that life is a gift not to be wasted.

Another part comes from growing up in a small town in Venezuela. Like many people in small towns, the people I grew up with would find joy and pleasure in small things, being able to go for a hike, having a warm piece of bread, singing over a fire, learning how to dance, making something out of nothing. Many decades later, I still think that we have much more pleasure figuring and making things instead of buying them.

And part of my optimism was firmly cemented when my dad, almost deaf and blind, came to live with him in his later years. His sense of joy and gratitude was so big! He was funny and witty and we had so much fun. We even created our own language so we could communicate. Dad could talk and most of his words were insightful and joyful.

Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?

I am a venture capitalist, financing early stage companies that use technology to make a positive impact in the world, creating a massive amount of wealth. I run a boutique investment club (for individuals) and a venture capital fund (for large investors). Besides capital, we are active supportera of the companies qw invest in. The business model originated after watching with frustration how founders would spend a considerable amount of time filling the last portion of a round, and, at the same time, watching angel investors make bad decisions and not having the proper support to reduce risks and increase profitability.

My journey has had many pivoting moments, I started my professional life as an academic researcher, studying genes in plants for over a decade, and growing up in a socialist country to socialist parents. One of my students invited me to talk to his boss and after many months I joined the corporate world as head of product development, with a keen interest in creating value. Several years later, I lost all of my money to a bank crisis and decided to learn more about business and pursue an MBA. I couldn’t be more fortunate, as I attended Babson College, the top entrepreneurial school in the world. From there I started several companies, and moved from founder to investor as I grew my wealth. Many countries later, I moved to Silicon Valley to change the way we teach business using the Wealhting principles: create and share wealth, balance creativity and productivity, use the past to create a future. However, I realized I would have much more impact using my capital and the Wealthing principles to invest in companies. In 2020, the Wealthing VC Club was founded to provide investors access to vetted post-seed deals. In less than five years, we have invested in 35 companies, including 5 unicorns, and in few of those companies we have invested multiple times. In 2024 we invested over $1M.

After over 90 investments, including 12 funds, I launched Wealthing VC Fund to offer institutional and family offices access to our best deals and pro-rata rights. Then late in 2024, I laid the foundation of the Wealthing Family Office, with my children and their children, allowing us to have a larger impact that would expand beyond my life.

In 2025, the Wealthing Podcast is launching, provided a non-nonse, after-dinner style family conversations about how we create wealth for us and for others.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

1. Grit. People talk about resilience, but grit is more about recharging. I have always been protective of my time to recharge, so I am full of energy because that energy does not get depleted.

2. Excellence. I have high expectations for everything I do, and people that work with me know that I have high expectations. We always talk about how to make things better. Attention to details is very important, and we openly criticize each other and the work that we do. Training as an academic scientist taught me the value of tossing knowledge to create new one. Others’ criticism help advance faster. We welcome criticism with curiosity, because we know the results are better when we can be free to express our opinion… but criticism with kindness is much easier to manage.

3. Kindness. We are our best when we can recognize that others need to be respected. We can do that tossing judgement away, and seeing through their challenges and opportunities, their inspirations and defeats.

Awesome, really appreciate you opening up with us today and before we close maybe you can share a book recommendation with us. Has there been a book that’s been impactful in your growth and development?

Rich Dad, Poor Dad. It helped me reflect immensely in my two lives: one as an academic and one as entrepreneur. It also helped me become better investor, help the founders I invest in, and the students I used to teach.

Contact Info:

Image Credits

All photos are mine

Suggest a Story: BoldJourney is built on recommendations from the community; it’s how we uncover hidden gems,
so if you or someone you know deserves recognition please let us know here.
Betting on the Brightside: Developing and Fostering Optimism

Optimism is like magic – it has the power to make the impossible a reality

What’s more important to you—intelligence, energy, or integrity?

There is no one path – to success or even to New York (or Kansas).

Finding & Living with Purpose

Over the years we’ve had the good fortunate of speaking with thousands of successful entrepreneurs,