Hello, this is Rita Liao. Welcome to Episode #2 of Leapfrog, a podcast about entrepreneurs who have ventured out of their native land and are reshaping a slice of the global tech landscape. You can read more about why I started this project in About.
Hailing from a rural chicken farm in eastern China, Winston Chi sauntered into a field after school every day, picking wild berries and daydreaming. It was a carefree childhood contrasting the academically rigorous, sedentary one his urban peers had in the 90s and 2000s. Occasionally, glimpses of the outside world came through gifts from visiting relatives, speaking to his village's history as a source of the Chinese diaspora.
When a relative brought home an early-generation iPod, Winston was enchanted — not by what music he’d put in the device, but its ability to store hundreds of songs. The original iPod sparked his interest in technology and a desire to explore the world beyond the berry field.
Winston is living in the Bay Area today. I talked to him just weeks after he sold his startup, Butter, to its larger competitor, GrubMarket, a pre-IPO company that offers software tools to farmers and growers across the U.S. On this episode, Winston talked about his journey from the chicken farm to a successful startup exit, the cultural differences he overcame (and is still working on) in the U.S., and how he handled his anxieties in life simply by taking action.
Winston’s words that stuck with me:
You don't have your family here. You have very limited support. So you actually need to be able to explain what you're planning to do, what's your actions and the potential outcomes to ensure you can gain support from people.
One thing I do believe is that if everything shut down, like all the restaurants were shut down… I think there'll be a new norm. In a few years when everything is back to normal, it will not be pre-COVID-19.
When I was there [near a California wildfire], the only thing that can deviate me from anxiety is taking actions. And that's still one of the thing I do believe: if you feel like you cannot really think it through on many things, take some actions and you will see through afterwards.
Because we didn’t grow up in Silicon Valley or went to Stanford and then work here, we have even a wider view of what the world should be, right? Especially if you are from a third-world country, you've seen the countryside super poor, you've seen the country developed so much in the last 30 years, and you have the belief that the world can be changed.
Timeline:
3:30 Winston’s biggest culture shock upon arriving in the U.S.: a society that rewards presentation, a contrast to Chinese people’s faith in meritocracy
7:00 Raising capital in Silicon Valley: try to make people’s life 10x better; and pitch in a way that even your grandpa can understand.
12:17 Winston doing the intuitive-enough-for-grandpa pitch
15:51 Why Winston pivoted from the crypto industry into a backward, “web 0.5” space
16:58 How COVID-19 inspired Winston to start a food distribution tech startup
19:18 Start building if you have a strong calling. It doesn’t matter if you don’t know the exact solution.
22:05 The best ideas always come from taking a walk and grabbing bubble tea with your teammates, not over a Zoom call.
26:35 How being an “outsider” positioned Winston well in building a food tech startup in the U.S.
28:42 Winston’s childhood in the Chinese countryside
31:18 How the diaspora community in Winston’s village shaped his understanding of the world at a young age
38:42 Winston’s three life essentials
Mentions:
DoorDash founder Tony Xu’s YC pitch in summer 2013
GrubMarket buys Butter to give its food distribution tech an AI boost (TechCrunch, May 2024)
The Art of Self-Defense, directed by Riley Stearns
The Social Network, directed by David Fincher
2001: A Space Odyssey, directed by Stanley Kubrick
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