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No Priors · 5 min · Apr 17, 2026
A deli taught McDermott to serve customers and bootstrap
At 16, Bill McDermott bought a deli for $5,500 and learned to tailor it to three customer groups. Supplier relationships let him stock the shelves on consignment and get started without cash.
Bill McDermott is chairman and CEO of ServiceNow.

Sarah Guo, Host · Founder, Conviction
Ex-Greylock partner; early investor in Cognition, Harvey and Mistral.
About this segment
At 16, Bill McDermott bought a deli for $5,500 and learned to tailor it to three customer groups. Supplier relationships let him stock the shelves on consignment and get started without cash.
From “Scaling Global Organizations in the Age of AI with ServiceNow Chairman and CEO Bill McDermott”, Apr 17, 2026. Watch the full episode
Thanks. We'll look at and fix what's off.
“So I got them to give me the first order on consignment.”
Takeaways
- He bought the business for $5,500, or $7,000 with interest.
- He drew in different customers by understanding what each wanted.
- Supplier relationships helped him get his first stock on consignment.
In this episode
Full episode- 19:16Enterprise platforms can cost less than rebuilding with AI6:03
- 36:21AI speeds implementation and changes who companies hirePro pick 4:40
1:34A deli taught McDermott to serve customers and bootstrap5:22
- 5 more moments in the full episode
Transcript
Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.
- 1:39
Yeah, I don't, I don't deserve too much credit for, you know, doing a strange thing buying the deli because I was really trading in multiple part time jobs. At the time I was stocking shelves, pumping gas and bussing tables. And so I had a chance to consolidate all of that into the delicatessen and have one job where I could spend all of my hours. And for a kid going to high school, that kind of made a little bit more sense.
- 2:11
So I got lucky. I bought the business for 5,500 notes, 7,000 with interest. If I make the payments, I keep it. If I miss a payment, they take everything away from me. So it was a pretty cut and dry moment. And I think the biggest thing that I've learned in my life, and especially there, is it's all about the customer. In the end, the customer and the customer alone determines whether you win or lose.
- 2:38
And it's a very simple equation. If you keep them coming back, you got a good chance. And if you don't, you lose. And, you know, back then, one of the most interesting parts about that store was knowing your customer and knowing your base. And I really had, you know, three main customers. You know, one was the blue-collar worker, like my dad, as I said in the book, was rich on Friday and dead broke by Sunday morning.
- 3:08
They were the senior citizens, and this was the early days of DoorDash, I guess, because they never wanted to leave their house, and we delivered, and no one else did. And the hard part was getting the kids to walk a block and a half past 7-Eleven to come to my store, and these were the early days of video games. and asteroids and pac-man and you know you tell that to people today most of them never even heard of these games but kids would stand there for hours plucking their parents quarters into those games and that's how i got them to walk a block and a half past 7-eleven and come to my store at the end of a long day one of the young people said to me you know when we want to have good food, be treated with dignity and respect, and play video games, we come to your store.
- 4:00
And when we want to steal stuff, we go to 7-Eleven. So if you take care of your customer, you know who your customer is, and you give them what they want, just the way they want it, no matter what business you're in, you've got a really good chance. And that's all I did. And it put me through school, including college, and it got me my start. And I have to tell you, the EQ that comes with dealing with 500 customers a day is worth a lot.
- 4:34
And I have a feeling the world could use a little more EQ right now. I learned a great deal, not managing a deli, but at least being a hostess in Outback Steakhouse. See? Yeah. You can relate, right? Well, you just, you know, the repeats of dealing with a lot of different types of people is useful. So it's still, like, amazing and strange to me. You talk about this set of customers that you, you know, understood and tried to serve.
- 5:00
Like, were you just sitting there in the deli observing them before you bought the thing? Like, how did you even figure out these were the people? I worked there first, you know, and what happened was the owner was going through some personal divorce circumstances and wanted out. And I was the guy that was always there anyway. So he tried to sell it. It was only a one-year lease. You never owned the land of the building, so he was selling a one-year lease.
- 5:28
The lease was owned by Sunmark Industries, which is Sunoco gas station, and they could throw you out anytime they wanted. So only a kid who didn't know any better would pay anything for it. So eventually, that's how the deal got put together. I said, I don't have any money, but I'll, you know, take a note from you and pay you back with interest. If I miss a payment, you get everything back. What was really interesting about the story is I didn't have any money.
- 5:56
But what I did have, because I work there, is relationships with all the suppliers. So I got them to give me the first order on consignment. I said, I will always pay you back. This is not a favor. This is a chance for you to get your shelves filled up with your stuff that I'm going to sell for you. But in the end, I'll always owe you that first delivery. And probably they charged me too much on the margin, but I didn't care.
- 6:26
I was in business, and that's all I wanted was a shot. And that's all I've ever wanted is a shot. And I'm so honored that in my life I've had the shot. And when you have a chance, you can really bring the winner within you out. And all people should ever want is an opportunity because an opportunity is a gift. And it's something that you should really cherish. And every time you get one, make the most of it.
- 6:53
That resonates.