Finding the Right Fit in ECommerce
After building out Walmart’s multi-channel businesses in the rapidly changing early aughts, Mike Smith was ready for a new challenge. And while he would have been hard-pressed to go much bigger, leaving the commerce juggernaut — where he was responsible for nearly 15,000 people in the field — for the four-employee direct-to-consumer startup Stitch Fix was hardly the obvious choice.
“I was looking for something that felt more like a co-founder relationship,” says Smith, who discovered that partner in founder Katrina Lake. Smith went on to spend nine years at Stitch Fix holding a series of senior roles — and eventually taking the company public in 2017.
That eye for what makes a great founder (for starters: humility, hunger, and clarity of vision) led Smith to his next venture, too: venture capital.
In early 2021, Smith joined his operational expertise with Nikhil Basu Trivedi’s investment prowess to co-found Footwork VC, where they focus on consumer technology and the consumerization of enterprise technology.
In building the next generation of category-defining companies, Smith says he gravitates toward organizations led by women and those from underrepresented groups: “What do I want my legacy to be? Where do I want to give time? And where do I think the ecosystem needs a lot of work? I do believe, fundamentally, that early stage investing, early stage founders, the LP base, all needs to be more diverse.” And with Footwork, he adds: “I think we’ll show that diversity matters and diversity delivers great results.”
For the Iconversations series, Smith sat down with Greylock general partner Mike Duboe to suss out the startup vs. incumbent dynamic from the inside, as well as discuss what he looks for in founders (and what founders should look for in early hires), the unit economics that make or break direct-to-consumer companies, and what he anticipates in the next decade of commerce. You can watch the video from this interview on our YouTube channel here.
You can listen to the full conversation here: