Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
Full method →
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q So I'm, I'm looking at the, uh, Facebook page for Shipt and you can tell how quickly this thing blew up. Like you start in Birmingham and suddenly like Shipt is everywhere. How many cities did you get to in year one?
A 15 cities. Shortly after we launched Birmingham, we said, all right, well, what are we launching next? I mean, it might've been six weeks later, we were looking at launching the next city. We ran the same playbook in every market. We did a pre-sale campaign for memberships, half price if you signed up before launch, and we launched Nashville. It was great. We launched Dallas, and it was a dud. Then we launched Tampa, and I call it, and my team, we, we all call it Kablampa because 2000 people signed up. We launched Miami. We had the same thing happen. 2000 memberships before we launched, and that's when I knew, I mean, this is going to work, and The company just exploded overnight. I remember having to go in the office Saturday, Sunday to answer the phones and talk to customers and shoppers and solve problems. We were all hands on deck just to, just to handle the demand.
AI assessment note: “15 cities. Shortly after we launched Birmingham, we said, all right”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q What did Graycroft think? I mean, they had just led the Series B. So, presumably, they had a price they wanted you to hit. Like, were they ok with you selling at that point?
A My partner there really pushed me to consider not selling. He said, look, I'm, I'm going to do whatever you want to do. I mean, you're the CEO and, you know, whatever you want to do, we're with you. And that was a tough decision to make, but ultimately what I came back to was If, if I had continued as an independent company and something else had changed or not worked out, how would I feel if I hadn't taken the. Five hundred and fifty million dollars is actually a little more than that. That was on the table and an all cash deal. And I said, you know, this, this makes sense to do this deal because once I've done this deal, then on the next company or the next one, I can hold the cards as long as I want to, and I can do all types of other deals, buy companies, start them up, whatever, I'll have so many options available to me.
AI assessment note: “My partner there really pushed me to consider not selling.”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Can you describe the day shipped sold to Target? You were 32 years old, and the company sold for over five hundred and fifty million dollars. Like, what was that day like?
A Oh, it was a great day. So it was December 17th, and I'll back up before the day it was announced, because the day it was supposed to be announced was actually December 18th. And I got a call from the COO of Target, and he said, hey, we actually want to announce this a day early. We're afraid it's gonna leak. So we're sending our plane down to pick you up this afternoon, flying you to Minneapolis. We're announcing tomorrow morning. So, I jumped on the target plane and flew up there. And the next morning, I'm on a call, um, we're doing interviews with the CEO of Target and myself. We're interviewing with CNBC and Bloomberg and the Wall Street Journal. All these things started at six a.m. in the Target headquarters. I'm watching the sun come up. I'm in this amazing office, um, and just, I mean, this is a dream. This is everything an entrepreneur dreams about doing, and I'm doing it. In the Target headquarters, they have a A bullseye, the, the, the dog, the mascot built out of Legos.
AI assessment note: “All these things started at six a.m. in the Target headquarters.”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Why did you start with smaller cities instead of the classic New York or LA?
A So at the time there was a company called Instacart. They had raised something like two hundred and fifty million dollars before shipped was even open. And they were very focused on the coast. They were New York, San Francisco, LA type markets, and they didn't do anything in the center of the country. So we just said, all right, well, we're just going to own the south and the center of the country, and we're going to focus on the rest of America. Because You know, it turns out people in, um, Grand Rapids, Michigan want groceries delivered just the same as someone in New York does, and even more than that, there's a lot more families in the middle of the country than there are in, you know, there's people with a bunch of kids, I thought. So, uh, it just worked out that way.
AI assessment note: “Instacart... were very focused on the coast... we're going to focus on the rest”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Can you imagine a point where there's Bill Smith not running a business?
A I think about that. I've thought about that a lot. Um, I, I don't believe that'll happen. Um, that's not my desire. Now, when I fast forward 20 years, 25 years down the road, um, I'm 38 today, and I think, you know, would I be a CEO at 65? Do I want to be doing this every single day? I don't know. Um, but I think I'll always own businesses, and that's something that I'm, you know, really am interested in. Um, I bought a business recently. I don't run it. Someone else runs it, and it's really more like an investment, but I can see making that transition at some point to owning companies, uh, working closely with the president or the CEO, coaching them, and kind of providing that guidance, but not being in one single business every single day.
AI assessment note: “I don't believe that'll happen. Um, that's not my desire.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q What did you think going into that suite? Did you feel like a big deal?
A No, no, I didn't. I felt like a little guy because I knew they were a big public company. I told him about our business and our size and before I even walked out of the room, he said, well, we're trying to grow in this space. We'd be interested in acquiring your business. And, uh, and he just threw out a number to me and said, you know, how does that sound? Is this something you might be interested in? And I said, well, let's let me, let me think about that a little bit. I, I, I didn't want to respond immediately. So I just, Said, hey, I'll get back to you, and that was the start of our relationship.
AI assessment note: “No, no, I didn't. I felt like a little guy”
