Courtesy of Sherry Jiang
As a business school student at UC Berkeley, Sherry Jiang felt like she had three career path options: accounting, banking, or consulting — or, "the ABCs," she told Business Insider.
She gravitated toward banking, landed a summer job at Goldman Sachs after her junior year, and wrapped up the internship with two main takeaways.
"Number one was I absolutely hated investment banking," said Jiang, who graduated from college in 2014. "And number two was, I realized how crazy of an opportunity it was to work in the tech industry. As I was working on these deals I was seeing these price-to-earnings ratios that were through the roof for tech companies."
That prompted her first career pivot, and she took a job at Amazon in 2014.
Courtesy of Sherry Jiang
In 2015, she switched to Google, a role that eventually brought her to Singapore to work with a team called Next Billion Users and essentially build products for just that: "The next billion users coming from markets like Indonesia, India, and Brazil, versus a first-billion user mindset, which would be more the US or European markets," she explained.
The opportunity gave Jiang a taste of what it's like to build something from scratch.
At a tech giant like Google, "most people are handed a billion-user product already, and you're trying to maintain it, but in this case, we got to work on essentially a startup within Google," she said.
After a few years, the product she was working on "grew to a stage where it wasn't that zero-to-one, super exciting, scrappy, hyper-growth stage anymore," she said. "I wanted to do something different and take a risk."
In 2021, Jiang left to try to build her own startup. She wanted to fully commit rather than start a company as a side hustle.
"I went all-in," said Jiang, who was 29 at the time and quit before she even had a fully formed business idea. She wouldn't necessarily recommend the same strategy, she added: "This is really personal style. Whatever I did is not a reflection of what you should do because it just depends. For me, I'm all or nothing. I need to have my mind be here and fully committed."
That said, she took a few steps to set herself up financially to leave the corporate world. She applied to and was accepted into an accelerator program called Entrepreneur First, which paid a stipend, connected her to other startup founders, and provided mentorship and structure. She eventually built a personal finance platform called Peek.
The timing was better than it would ever be, she added: "I had enough savings where I could sustain myself, I wasn't at a point where I had dependents or kids." Plus, it was early Covid when there were strict stay-at-home requirements, and it was "the best time to be heads-down, go all-in, and try the entrepreneurship journey."
Jiang could afford to take the leap, thanks to smart investments she made in her 20s, including Tesla. She also received RSUs as part of her compensation package with Google.
She pointed out that luck certainly played a role in her portfolio growth.
Courtesy of Sherry Jiang
For asymmetric returns, you have to "go where the growth is early on," she said, which happened to be tech in the 2010s. "I do feel like it was a bit of a 'right time, right place' type of thing, where I happened to go to a school in the Bay Area, I happened to work in the Bay Area, and so tech was part of my psyche during a time when tech just did super well."
But she also prioritized landing a high-paying job and consistently saved and invested a portion of her tech income.
"You want to work somewhere where not only you're earning hopefully a lot in cash, but you have RSUs or stock options," she said. "That's where a huge amount of my net worth growth came from — maybe even 50% of it was just from RSUs because Google stock did really well."
Her advice to young investors is to "go where you actually have the opportunity to earn a lot early on and make sure you don't spend all of it. Don't get lifestyle creep, don't burn all your money, invest that money, and be super disciplined about it."
When Jiang was thinking about quitting, she looked at her net worth and approximate investment income percentage. "I can basically live a much more bare-bones life and get by," she realized. "It was almost like I had essentially an infinite runway if I downsized completely."
She made a few lifestyle changes to lower her cost of living, including moving in with two roommates.
"It was one of those things where I never thought I would do it again but I decided to live with roommates in my 30s," said Jiang, whose roommates are also startup founders. "I used to pay about 50% more in rent, so that makes a huge difference."
She also travels less and is generally more aware of where her money is going.
At Google, she had what she calls "cash flow without consequences " and spent more freely. "Now, I'm way more conscious about what I truly value."
Courtesy of Sherry Jiang
When it comes to tracking her financial life, she pays attention to two main numbers: Her savings rate, which she ensures is at least 30%, and her net worth.
She uses the personal finance platform she built to stay organized, noting that a lot of good startup ideas start with a problem you're trying to solve in your own life.
"I have a very complex personal finance life. I have a lot of accounts in the US, I have my stuff in Singapore, and then I also do a lot of crypto investing so I have a handful of wallets and random holdings," she said.
It turns out, she wasn't the only person in Singapore finding it challenging to manage personal finances. While well-integrated wealth aggregation is not new in the US, it is in Southeast Asia. After talking to peers and people in her network, she found that "there is effectively zero solution except Excel in Singapore."
Peek addresses that problem, and thanks to her financial preparation, she built it in a relatively low-pressure environment.
After all, once she calculated her runway and realized that she had enough in savings and investment accounts to sustain her lifestyle without earning a consistent paycheck, it gave her time to "explore and make sure that entrepreneurship is really for me — and if the ideas that I have really have legs."
