Name: Pinterest CEO Bill Ready Learned This Early — And It Shaped His Toughest Call
Uploaded: 2026-02-03T18:19:36.000Z
Duration: 40 min 12 s
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Every leader's journey is shaped by a handful of defining decisions, those moments of risk, doubt and conviction that influence their lives and careers.

To-infinitive

In this podcast, we get to hear the stories behind those choices.

Welcome to Executive Decisions with me, Steve Sedgwick.

In this episode, I speak to the CEO of Pinterest, Bill Ready?

We can get sort of trapped in the constructs of what we think is possible.

I actually think for all of us, so much more is possible than what we imagined.

Bill grew up in a small town in Kentucky, working in his parents auto repair shop.

Become the first in his family to go to college, get a stable job and have health insurance.

But he went on to exceed those expectations and move from the shop floor to Harvard Business School, Silicon Valley, and

The further I've gotten into my career, the more I look back and say a lot of the best lessons actually came from that little town in Kentucky, that little auto repair shop.

As CEO of Pinterest, Bill faced his toughest decision yet, making the platform private for users under 16.

It was controversial, but it was guided by a strong sense of accountability.

Users become sort of nameless and faceless, but

for me, I see every single one of them staring back at me.

These are Bill Reddy's executive decisions.

I can't work out what you evolve to and from vc, working for the big corporations, working for small corporations, being a CEO, setting your own companies up.

I do five startups, so I would still consider myself primarily entrepreneur.

Although I was an accidental entrepreneur.

I didn't grew up in a little town in Kentucky and you know, my aspirations were as a person, my family go to college and my aspirations were, you know, get a stable job and have health insurance with family, you know, didn't have health insurance growing up, you know, grew up in, you know, a place where, you know, I needed government assistance to get to college and things like that.

So get to college, graduate, get a stable job, actually have health care for the family.

But then have ended up having the good fortune to have built, you know, multiple of those to billions of dollars in revenue.

And so I've ended up running larger companies as a result of that.

But in my heart, I'm an entrepreneur and a builder.

I know you work for the family business, the garage, and

Tell me about the key influences and the people you drew inspiration from when you were very young.

Yes, My parents were, are small business owners, little auto repair shop in a small town in Kentucky.

And so, you know, I grew up working there and you know, later on in life I'd get to, you know, Harvard business school and McKinsey and Silicon Valley and all those places.

The further I've gotten in my career, the more I look back and say a lot of the best lessons actually came from that little town in Kentucky, that little auto repair shop of just, you know, what it means to take care of customers, what it means to do the right thing by people, what it means to have a long term relationship with your customers.

And, you know, and so those were instilled pretty early on.

I always say I started working out a repair shop when I was 13, but

Before that, I paint the building and, you know, repave the asphalt and started like 7 or 8 years old.

So hard work was a must from the beginning.

So again, these are things like the more time goes by, the more I appreciate how valuable these things were.

You know, at the time I was like, oh, my friends are getting to do all these other things and I'm here working, drive by while I'm out there, you know, sort of, you know, working in sort of wave and thinking, oh, wow, I wish I was doing that.

And I look back now like, oh no, those are like really important lessons.

So there's no way you could have been successful as you've been in Silicon Valley and elsewhere and these extraordinary companies you've worked with for and created if you didn't have a strong work ethic as well.

Has that been instilled in you that actually a job isn't just 9 to 5?

I mean, I would say, you know, for my family, a lot of it was just necessity, but

I think the work ethic was definitely there.

You know, my dad woke me up to the Navy reveille every morning for, you know, 18 years, just about.

So there are definitely things like that.

You know, that little town in Kentucky was just outside of Fort Knox, so grew up outside of a military base.

And so a lot of those things, you know, sort of in terms of discipline and work ethic sort of rubbed off in that.

But a lot of it is, you know, hard work out of necessity just because it was, you know.

You know, I always talk about the link to doing good things for customers is sort of, you know, instilled in an early age because we literally, you know, if we took good care of customers and business was good, then we ate well, if things weren't going great with customers, you know, then it was, you know, we go to the grocery store on the other side of town where, you know, the meat was only expired by a few days and probably wouldn't make you sick.

So that linkage of like, hey, take care of customers and good things happen for you was sort of there for long, but

But I actually think, you know, as an entrepreneur, one of the things back to, like, lessons I didn't realize were such powerful lessons then necessity is the mother of invention.

You know, I'm a huge believer in the theory of constraints like Silicon Valley.

You know, so much of Silicon Valley, people talk about tech titans and things.

Now, the story of Silicon Valley is not one of titans.

The story of Silicon Valley is one of, oh, an upstart with, you know, no resources, but, you know, a lot of imagination, a lot of hard work, and

a lot of ingenuity can go take on massive incumbents.

Tell me about taking responsibility as well of your mistakes.

So I was 13, had just started, you know, actually

working on cars in the shop, and I had messed up on a farmer's truck and actually donated.

It sort of actually less the mistake itself, but

more that we're going to need to keep it for an extra day for me to.

To sort of redo the work that I had done.

And, you know, I'm sort of expecting my parents to go explain to him what I'd done.

I said, no, no, you go tell them what you did and what you do to make it right.

And, you know, as I tell the story, people oftentimes imagine it's going to be like a Norman Rockwell painting or something where the farm's, oh, son, it's all right.

No, he needed that truck for his livelihood.

Like, that was, you know, it was a place where, like, most people were living paycheck to paycheck, and

he needed that for his livelihood, and he let me know it.

And so even I've told that story a few times, even telling it now.

Like, every time I tell, like, I feel the lump in my throat of, like, what it felt like at 13 to stand there, like, knees knocking and having to look somebody in the eye, explain to them, you know, the mistake I made and what I was gonna do to make it right.

And, you know, back to, like, powerful lessons from early on, I think One of the things that has happened in tech is that, you know, there's so many people running platforms with hundreds of millions or billions of users.

And I've had the good fortune to work on products that, you know, that have served billions of users.

But I think for so many people that are working on these products, they don't have to sort of look eye to eye with all the customers.

And with hundreds of millions or billions of users, users become sort of nameless and faceless.

But for me, I see every single one of them staring back at me.

When we make decisions about what we're going to do, that's sort of my bar is, could I look someone in the eye and say, you know, I did my level best to do what, in my heart of hearts, I felt was the right thing?

That's going to come up later in your story when we talk about Gen Z as well and your extraordinary actions.

You grew up in, for want of a better word, a really tough rural environment where it was really tough for the customers, it was tough for your family.

Paycheck to paycheck, customer to customer.

Is, you know, that was sort of the dream was just to get to college.