Alicia Castillo Holley is a serial entrepreneur and angel investor who invests in 8 new companies a year.

What’s your story?
I’m a serial entrepreneur, and angel investor. I grew up in a small town in Venezuela, and was a scientist (presented my first paper at 15), then head of R&D, and found entrepreneurship through a Babson College MBA. I’ve had a fascinating life, moving to 6 countries, creating startups, investing in them, and teaching and researching about passion, socio economic development, and venture capital. I now live in Silicon Valley and am a full time angel investor. I’m also a writer and speaker.

What is your involvement with Investment?
I invest in around 8 new companies per year, and I’m also an LP in three (soon to be 4) small VC funds. I created and ran Chile’s first seed capital fund so I enjoy the many colors of equity investment. I’m a member of Sand Hill Angels too. I also run programs for entrepreneurs and consultants and I’m a frequent speaker.

How did that come about?
When I first raised money, I developed a profound admiration for the angel investors that supported my projects. I valued their wisdom and now that I have enough resources, I decided to follow those steps. I also liked the research I read about angel investing. In terms of managing a VC fund, I noticed that I could not find in Chile an organization that provided the support (capital and non-capital) that some great companies needed. I had a consulting company then, and later a research and training organization. I noticed then that socioeconomic development is a stick with two ends, one is the entrepreneur and the other is the investor. We need both to lift the economy. As I did not see who could be the early investor, I created a model, organized it into a fund, raised the capital and resources, and executed it.

What are some of the key things you have learnt about Investing?
Action reigns. There is no substitute for action. An entrepreneur that is good at thinking but does not act does not work for me.
Also I like to work with individuals who are curious and that curiosity turns any disagreement into an opportunity to explore new ways of doing things.
I also learned to say NO.

What mistakes do you see less experienced investors making?
Being greedy, wanting to control the entrepreneur (instead of supporting him or her), and being comfortable with the idea that failure is an option.

What mistakes do you see Entrepreneurs making?
Mistrust and lack of preparation are on the top. If an entrepreneur wants my money but does not trust me, and does not appreciate my knowledge and wisdom, why should I take the risk of supporting them?
The lack of preparation and the ignorance about business topics and the topics critical to the industry makes me lose interest.
Last, some entrepreneurs listen to consultants that have not raised money and get ill advice, or they follow news that are incomplete or inaccurate. Money is a commodity but people are not looking to throw away or gamble money in start ups.

What’s the best piece of advice you ever received?
Close that company. One of my biggest failures was driving me crazy. I had been working on it for 4 years without making a sale – we had users but not paid customers. We kept pivoting, improving it, expanding it. I even had to fire my co-founder, the CEO of the company. It was painful. A friend who was also an angel investor called me up and offered to put funds in the company to give it a runway of 6 months. With the promise that I would close it if we did not make a sale. We made big changes, but within a couple of months, I could tell that we did not have a viable model and closed the company (and returned the unused cash).
Years later, I had to convince another co-founder on another company that we had to close it. We had had the opportunity to sale it and he did not take it. It was his first angel investing deal, and he was fixed in making a good return. We ended up selling at a loss months later.

What advice would you give to those seeking funding?
Never miss the opportunity to learn from rejection: What do I need to change to make this a more attractive deal? Is a great question.
Also do not take NO personally. Investors have many reasons to reject a deal.
Last, be prepared. Understand what are the key issues you are solving and what is the deal you are offering.

Who inspires you?
Individuals who are passionate.

What have you just learnt recently that blew you away?
How cryptocurrencies and e-sports are disrupting the financial and sports industries respectively.

What business book do you recommend the most?
Rich Dad, Poor Dad by R Kiyosaki
Mindset, the new psychology of success, by C Dweck
And of course my book How to Fund your Million Dollar Idea, by A Castillo Holley, and the Ten Unwealthy Habits.

Shameless plug for your business/organisation:
I developed the Wealthing® Method to help people manage: passion, profits and purpose.

How can people connect with you?
[email protected]; My assistant: Daniel Chapellin

Social Media profiles?

This article is part of the World Business Angel Forum media partnership with

If you would like more information about WBAF, please contact Callum Laing WBAF High Commissioner for Singapore. [email protected]

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