Brittany Yoon
3 min readJun 12, 2017

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At the height of the internet bubble, people thought everything we do but don’t like to do can and should be automated.

So, VCs threw money at streams of bright eyed companies (history is funny, isn’t it?) People will always need to eat and some people really despise parking lots, so groceries became an obvious target.

When I was nine, a company called WebVan dreamed of robots picking out groceries and built elaborate technology in the hopes of deliver groceries to customers within 24 hours. For many reasons, it crashed and burned.

Since hindsight is 20/20, there is now great consensus on why WebVan failed: WebVan didn’t realize that providing Whole Foods quality produce at Safeway prices, while offering free delivery (their tagline) means they can’t make any money and they might as well call themselves a charity. The reason you hate pulling your shopping cart and loading the checkout conveyer belt is because that’s real work. But instead of getting paid for work, you’re paying the store to do that work.

While WebVan’s complex infrastructure and automated distribution center technology was impressive, it did nothing to its bottom line. Before they had mastered their business model in Oakland, they built fancy and expensive distribution centers in many cities and expanded rapidly. (“Growth at all costs.” Sounds familiar?) When investors started getting anxious about their returns, WebVan had to cut costs by compromising on all that they did for the customers. Customers, who were already difficult to acquire in the first place, were quickly disgruntled and left in swarms. Inevitably WebVan declared bankruptcy and went on a fire sale of its assets to Kaiser Permanente. In short, WebVan grew too quickly and squandered capital without ever fixing the bottom line.

18 years later, the world has almost resolved my need to go to the grocery store to avoid starvation. On Instacart, I can hire someone else with more time (and lower opportunity cost) to go shop and deliver me groceries and pay 15–20% more than I would have had I DIY. If I live in one of the urban hip cities, I can shop from Amazon or Google, who still believes in automating grocery picking and profitable grocery eCommerce through economies of scale.

But two questions still haunt me.

1. Will Brick and Mortar ever be replaced in groceries?

People now love craft beers. I love Whole Foods’ natural make up selection. Purchasing these items is a lot about the experience: eye shopping similar items in the aisle, letting the marketing copy beguile your rationality, judging quality completely based on unrelated things like logo, font, and packaging. Foodies are even worse about their produce. My mother will never buy a watermelon without knocking on it to check that it echoes back a “clear sound.” (I know as much as you do about what that means.)

2. Who cares about the non-millennial, non-1%, non-NY/SF residents?

You know, people who don’t live in the coastal cities, the people we often forget about, a la 2016 election? They still deserve convenience and may be willing to pay for it though they may not know it yet.

This led me to spend my summer at a foreign, exotic place, unlike anywhere I’ve ever lived before, with very different people, culture, and landscape:

San Antonio, Texas.

I’m working for H-E-B, 6th largest food retailer in America, looking at their e-Commerce strategies. I will save the “why am I working for H-E-B this summer” for a later post…

Here’s to 10 weeks of food retail!

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Brittany Yoon

Building in web3 || Previously early employee @ App Annie, Uber, Ethos. Investor @ NFX.