Photo by Jon Anderson
Bill Smith, the founder of Shipt and the Landing aparrtment rental company in Birmingham, Alabama, talks with people after speaking to the Vestavia Hills Chamber of Commerce at the Vestavia Country Club on Tuesday, June 10, 2025.
The man who sold the Shipt same-day delivery company to Target for $550 million in 2018 started out as a high school dropout, but he was no slacker.
Bill Smith initially got a job selling Nextel phones while he was still in school at Homewood High School. He was so good at it that he was making $5,000 a month and decided to rent some office space without his parents’ knowledge and quit going to school, he told the Vestavia Hills Chamber of Commerce Tuesday.
After about two weeks, the school counselor called his parents and asked if he was OK because he hadn’t been to school in a few weeks, he said. They had a meeting at school, and Smith ended up dropping out of school and going to work — with the support of his parents, he said.
During a luncheon speech to the Vestavia Hills chamber at the Vestavia Country Club, Smith on Tuesday recounted a series of business startups he undertook and shared some of the challenges he faced along the way and how he overcame them.
Smith started a financial services company when he was 19, built it up and sold it to a private equity firm when he was 23. He then founded Insight Card Services, a company that offers reloadable prepaid Visa cards, in 2009 and sold the company to Green Dot Corp. in 2014. Next came the Shipt same-day grocery delivery business, and after selling Shipt to Target, Smith in 2019 started Landing, a Birmingham-based furnished apartment rental company that offers flexible leases with no deposits.
But while Shipt ended up making Smith a multimillionaire, the business didn’t start out as a success, he said. “It was actually a total failure.”
When he first called Target to offer a same-day delivery service for its website, “they pretty much hung up in my face,” Smith said.
He invested a lot of money, built a website and “literally nobody used it,” Smith said. “I couldn’t pay people to use it.”
But Smith didn’t’ give up; instead, he used a little ingenuity. He set up a website that offered people a free dozen of Krispy Kreme doughnuts delivered to their door within an hour and used those responses to build an email list and survey people about the idea of getting same-day deliveries from various stores.
He was envisioning delivering merchandise like computers and headsets, but the responses he got from a lot of mothers is that what they really wanted was to have their groceries delivered to their house, and that’s what motivated him to get into the grocery delivery business, he said.
They sold 1,000 memberships before they even had the first line of code written to run the delivery system, and by the end of April 2015, they made their first grocery delivery, he said.
“It was really an overnight success,” Smith said. “It was just beginning really at the right time. We were serving a need that really had always been there. Nobody had recognized it. A lot of people had had the idea; they just never did it.”
One of Smith’s biggest pieces of advice for people in business is that ideas are worthless unless they are executed. “If you just execute, you’re ahead literally of 99% of the people,” he said.
A lot of people are “wantrepreneurs,” Smith said. “They want to be an entrepreneur, but they won’t take that step, take that risk and just go do it.”
Smith also said that entrepreneurs have to be flexible and be willing to change their plan if it isn’t working.
“With just about every idea I’ve had, what ended up working was not what I set out to do in the first place,” he said. “It’s usually something else.”
A lot of people also spend too much time worrying about everything that could go wrong when, most of the time, those things don’t actually happen, he said.
“So what I really encourage people to do is you just gotta get out there and do it,” Smith said. “You just have to start. If you just get in the game and take it day by day, you’ll wake up, and the compounding you’ll experience is incredible.”
If you can get 1% better every week, in 10 years, your business will be 150 times better, he said, and if you improve 1% a day, you’ll be about 15,000 times better.
Smith also helped start a bank in Alabama called CommerceOne Bank and said what helped that business grow to almost $1 billion in assets was “just a little bit of hustle.”
Most bankers are lazy, he said. He found that if his people would just answer their phones, respond to text messages quickly and get loans approved quickly, they could be better than 99% of the banks that are out there, he said.
“You just have to hustle a little bit harder,” he said. “You don’t have to launch rockets into space to be really incredibly successful.”
Smith said he loves living in Birmingham because it’s not as congested as a lot of larger cities and commute times are reasonable, giving people time to get home to their families. Also, the business climate in Alabama is such there aren’t a lot of regulations that cause unneccesary burdens, he said.
His bank, like others, is highly regulated, he said, “but if you’re talking about starting up companies and small businesses, the less the government can be involved in your business, the better it is for everybody because it allows you to create opportunity,” Smith said. “If you have to worry about getting this license, that license, this report, that compliance exam, all of that takes away from your ability to create. And so I really appreciate the regulatory environment we have here in this state, in this city. It certainly has made it easier.”
