It didn't work.
"We launched that, and what I figured out really quickly…was that people don't want a dis-integrated experience. They want to be able to go to a site and do everything in one place and checkout and be done," he says.
"That was an important lesson," says Smith, if a needlessly expensive one. "I could have really tested my initial idea by using a Google Sheet and a form and posting on Facebook and saying, 'Hey I'm delivering from these retailers, fill this form out,' and we could have built a manual process.
"The lesson learned is test the ideas first in the lowest cost way and just take a simple approach," Smith adds.
At that time, in December 2014, Smith says the company was on the brink of shutting down. The model wasn't working and people were telling him there was more of a demand for groceries than anything else.
"I kept getting emails from people that tried the service that would say, 'Hey, it's cool that I can buy a pair of Beats headphones and get them delivered the same day, but what I really want is my groceries delivered,'" Smith says.
The idea of a same-day grocery delivery service didn't initially connect with Smith until early January 2015, just a few days after his second baby was born and he experienced a stressful shopping trip with two infants in tow.
"[My wife and I] went to the grocery store for the first time with a 1-year-old and a newborn and it was such a huge pain. Both kids were crying in the store, and we just had to get the heck out of there.
"Literally in the parking lot of the grocery store I told my wife, 'You know a lot of people have been asking for grocery delivery and I want to figure out a way to solve this problem.'"
The Monday after his epiphany, Smith walked into work and told his team they were going to pivot and put all efforts into grocery delivery and focus on building a fully integrated experience, where customers could do everything from purchasing the product to getting it delivered, all on one platform.
"At the time, nobody even had an in-store pickup option. That did not exist in grocery at all like it did with general merchandise retailers like Best Buy," Smith says.
To validate that the service was indeed in-demand, he told his team not to write the first line of code until they had sold 1,000 memberships to the service. For the first time, he awarded all of his employees, roughly 10 of them, stock options in the company.
"I said, 'Look, we're going to try this. If you guys are in, awesome. If you're not interested, it's cool.' And everybody stayed on board," Smith says.