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Christine Tsai shares lessons from her entrepreneurial journey and angel investing at NATEA Women's Summit.
Christine Tsai, CEO and co-founder of 500 Startups, shares her career journey from employee to entrepreneur and her insights on angel investing at NATEA Women's Summit.
Founded in 2010, 500 Startups is an early-stage venture capital firm headquartered in the US. As of March, the company invested more than 2,400 startups and 5,000 founders across 75 countries. Of these, eight startups have exceeded US$1 billion in valuation. They are Bukalapak, Canva, Credit karma, GitLab, Grab, Intercom, Talkdesk, and Udemy. Under Tsai’s leadership, she has grown the company to over US$500 million committed capital, according to Crunchbase.
Little did one know, Tsai has no personal investing experience prior to founding 500 Startups. She spent more than eight years as product marketing manager at Google and Youtube.
The beginning of Tsai's investor journey
She recalled the early days of her investor journey, remembering that most of 500 Startups' deals came from referral at the beginning. Being in the ex-Googler network allowed her to connect with various talents, and what she and her team did was to further expand that network.
"The work we did was to expand that network beyond what we were comfortable with, and that's how we found great opportunities," Tsai said.
"We were expanding internationally to founders that weren't the typical founders you would expect from Sand Hill Road (the VC hub in Silicon Valley), for example, female and underrepresented founders, and that led us to build our portfolio like it is today," she elaborated.
She cited her leadership style as sapient, meaning someone who is able to navigate continuous changes, especially with what's happening with the pandemic. She listed out four crucial elements to sapient leadership: Humility as a leader, providing trust and safety to employees, empowering them, and giving them a sense of purpose.
"A lot of people think leaders have to be the one with all the answers, which is actually not the case. This is what you built a team for," she said.
To be a leader is to be humble and down-to-earth, the person to instill trust and psychological safety among teammates. She said this is the key of a high-performing team. If teammates feel trusted and empowered, they are more willing to take more risks, make mistakes, and as a result, the team as a whole is more likely to advance further.
Angel investing in today's world
Tsai said becoming an angel investor is relatively easy nowadays, compared with 10-15 years ago. The startup market is overall more mature, investing has gone mainstream, and there are emerging startup ecosystems.
Tsai said, investing is never smooth sailing. As an investor, what challenges Tsai the most is "the longevity" of an investment and "the conviction" to lead.
Longevity refers to the fact that it takes a long time to determine whether your investment is successful or not.
"You don't know if you are good for a very long time, especially if you are an angel or an early-stage investor. It requires a lot of patience. You really have to be in it for the long term," she said.
One of 500 Startups' first funds is now entering its 10-year milestone, and only till now, she is starting to see results.
As for conviction, she expands it into two meanings: One, to continue to have that conviction in the company; and two, to understand how to build conviction as an investor. It is difficult to behold or build strong beliefs in startups or founders because usually in the early stages, these startups might not have much of a product.
"It really is about the team and the founders. You have to be mindful of how you build that conviction when there is very little data to go off of. And keep in mind your own biases," she urged.
"There are certain founders where you can say 'I have very strong conviction in them'. And there are other founders who you don't feel the same at first glance, maybe because they are not presented as well, or subconsciously they got overlooked because they don't resemble the typical type of founders you meet. That's why it's important to understand your own biases," she said.
She added that 500 startups aspires to invest in the next unicorn founders that are not coming from Silicon Valley. Instead, they will be coming from other parts of the world and diverse backgrounds.
She has two tips for aspiring angel investors. The first one is setting your expectations. She frankly stated that many people think they are going to invest in the next Uber or Coupang and become rich, but in most cases, this won't happen.
"The vast majority of startups don't go anywhere. Their failure rate is very high, and that's kind of what the venture is built around. You should be doing it for reasons beyond making quick returns because that is probably not going to happen," she advised.
The second piece of advice is to think about a specific thing or sector you want to invest in and ponder over your value to the startup.
Women in venture capital or tech
As a female Asian American with a quiet personality, Tsai said she doesn't fit the traditional perception of a venture capitalist, in terms of gender, ethnicity, and personality. However, there has been a shift towards embracing diversity. Being aggressive is not the only way to succeed. She reaffirmed quiet leadership and stressed that it should not be the minority's responsibility to change in order to fit in.
Conversely, another speaker in the two-day summit, Jolie Huang, director of product management, Dictionary.com, advised the audience to "fake it till you make it". She described Asian culture as more polite and submissive, in contrast to the business world in the US, which is much more harsh and confident. She, who used to say sorry all the time, had learned only to apologize when she meant it.
Other speakers in the two-day summit have also shared tips for aspiring investors or tech workers.
Morgan Lai, founder and general partner at Formulate Ventures, emphasized the importance of building a network of experts, executives, and angel investors and developing these relationships.
Meanwhile, Grace Chou, vice president from Felicis Ventures, noted it is important to build a diverse team and board.
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