A Conversation with Bill Ready, CEO of Pinterest

On his career, making decisions, and how technology can work for us

Editor’s Note: The Harbus is continuing its Leadership series, featuring conversations with leaders across business and society. We sat down with Bill Ready, CEO of Pinterest and former CEO of Venmo, to discuss his unique career, background prior to HBS, and how he is leading through a time of major technological change in his industry. 

Pranav Bharadwaj: Thank you for sitting down with me Bill; it’s a pleasure to interview you for the Harbus. Starting off: You’ve worn every hat - startup leader, consultant at McKinsey, C-suite at a Fortune 500. Which did you enjoy the most, and how did those experiences differ?

Bill Ready: I’m a builder at heart. I started my career as a computer science undergrad, and during the dot-com era I fell in love with how easily you could create something that people would use. That’s what I’ve always loved most, and it’s still the best part of my job.

I did two startups before HBS, but I was an accidental entrepreneur. I had a scholarship that paid tuition, but I was working two or three jobs to cover living expenses: second shift at the liquor store, third shift at UPS chucking boxes, etc. I figured out that working at a startup would let me have one job instead of three, and from that I fell in love with building things. Both startups had IPOs and later sold. My takeaway: the software really worked, but the business model didn’t. So I thought, I’ve got to figure out how to build the business model too. What’s the best place in the world to do that? Harvard Business School. I’d never met anybody who’d gone there.

When I got done at HBS, I still didn’t feel like I knew enough, so I went to McKinsey. After a couple of years, I said, I just have to go back to building. I went to an early-stage PE-backed company, my first chance running a company. Leaving McKinsey, literally 90% of the people I talked to said, “Bill, you’re nuts. You’re on track to be one of the youngest partners at the firm.” Well, it was at that startup that I got the ideas that led to Venmo and Braintree. Maybe that says something about the 90% of advice people are getting right now too.

PB: Do you think if you’d started McKinsey straight out of undergrad and then come to HBS, you’d have felt more comfortable taking a startup route out of business school? A lot of people here are wondering: do I jump ship now, or stay on the learning trajectory and leave later?

BR: Two things I generally say to people thinking about a startup. First: how much passion do you have for your idea? Choosing to build a startup is a little like jumping out of an airplane and building the parachute on the way down. So if you’re going to do it, you should have so much passion that you can’t stop thinking about it, the minute you wake up, lying in bed waiting to sleep, in the shower. You’re going to need that level of conviction because it’s really hard.

Second: it’s way easier to take risks when you have less to lose. In my first two startups, I was a broke college kid. If the startup went bust, I could always go back to the second shift at the liquor store. Had I waited until I was on the partner track at McKinsey, I’d have been walking away from a really good income and career trajectory, and it would have been much harder to ignore that 90% of advice.

Those two pieces can seem in conflict, but I think that’s the cognitive dissonance people have to hold. There’s inherent risk, so you need real passion and conviction. At the same time, it’s way easier to take a swing at a home run when the cost of a strikeout isn’t death, or isn’t perceived death. So I generally say: if you want to take that risk, better to do it earlier. And fortunately, here in the US, especially in Silicon Valley, having tried and failed is often a badge of honor.

PB: You went from king of the castle (CEO of Braintree) to being, for want of a better word, an employee at PayPal. There aren’t many people who become CEO and then step back into the ranks. Did you have to make a mindset shift?

BR: I did five startups, went through three IPOs and five sales. Each time I sold into a larger company, I’d stay for about a year and then, literally on day 366, I was off to build the next thing. PayPal was the first time I stayed, but not because I had aspirations of running a bigger company. I did it because I truly believed that for Venmo and Braintree to achieve their potential, they needed to find a home where a two-sided network in financial services was understood. PayPal was one of the only places that existed. So I chose to stay to see my babies grow up.

It can be really hard to shift from being the person in charge to fitting into a much larger company. Two things I’d say: 

1) Having that passion and conviction, “I’m here to see my babies grow up,” gave me the fuel to work through the death by a thousand paper cuts that entrepreneurs often get overwhelmed by. 2) I never stopped believing I was in charge, almost painfully so. I felt that owner’s mentality: if I see something broken and a way to fix it, I can’t not try. 

That irritated a lot of people. But I was fortunate to have great mentors who helped channel that energy more constructively, and I was willing to take on my own learning journey of figuring out how to operate differently in a bigger environment without losing the entrepreneurial drive. The payoff was building at greater and greater scale. Getting to have an idea and then, a few months later, seeing hundreds of millions of people use it, that was a new kind of high.

PB: It sounds like you love both zero-to-one and one-to-ten. Is that fair?

BR: That’s exactly right. Not everybody loves both, and it’s a hard transition, which is why you do see a dichotomy. But I really do love both, and if you can do both well, it just amplifies the joy. I had to be willing to learn what it means to operate differently at scale, while consciously shifting between the zero-to-one and one-to-N modes and knowing which moment calls for which.

PB: From the outside in, it feels like an inevitable rise to the top. Was there any self-doubt along the way? Any moments where you felt you got something wrong?

BR: My mentality is that only the paranoid survive, which means you’re always questioning yourself. Even twenty years later, I’m still convinced I was an admissions mistake in my HBS class because the rest of the class is just so talented. But I’ve always tried to channel that self-doubt in a healthy way. Maybe I was just the quota, maybe you’ve got to have at least one kid from a small town in Kentucky in the class. So what? I’m going to work as hard as I can so that when the next kid like me, first in the family to go to college, from a little town in the middle of nowhere, applies, I don’t mess up their shot.

I think anybody who’s truthful will admit they’ve had some element of imposter syndrome. The question is what you do with it. My choice was to make it fuel in the tank.

PB: When making consequential decisions, like leaving McKinsey when 90% of people said it was a bad idea, what’s your thought process?

BR: On career decisions, a lot of it comes down to being honest with myself about what I’m really passionate about. Am I choosing to work on something I actually care about, regardless of whether it’s conventional or aligns with the advice of others? Love what you do and you never work a day in your life. It’s a cliché, but these truisms exist for a reason.

On the things we build for others: it should sound like motherhood and apple pie to say we should build things that are good for the people who use them. But I think tech as an industry has lost sight of that. Is AI a tool that serves humans, or are humans the product? That’s a very fundamental question. When you look at why AI polls so negatively, with about 70% of the US population feeling negatively about it, I think it’s because there hasn’t been nearly enough thought put into how we make sure this technology is actually good for the people who use it.

I grew up working in a small family storefront from the time I was in elementary school. If we made customers happy, we ate well. If we didn’t, we didn’t. Even now, serving hundreds of millions of users, my mental model is: could I look them in the eye and say I did my level best to make sure what I was building was good for them?

Then there’s a second framework for the really consequential decisions, the near-term versus long-term tension: am I evaluating this from next quarter, or from my deathbed? When we made Pinterest private-only for under-16s, we took a big hit to our stock price. But through the deathbed lens, what would I rather have on my epitaph: that I got fired for trying to protect kids, or that I made a lot of money but ruined a lot of kids’ lives? Through that lens, it was an easy decision.

I remember the Tylenol case at HBS. If you just did the statistics, it was 0.0001% of bottles. But the decision was: if one person dies because we didn’t pull these products off the shelf, you can’t live with yourself. Of course you pull them. That 0.001% applied to billions of people is really consequential. We’ve got to be willing to say: we can’t ship these things if we don’t make them safe. As we get deeper into an AI-driven world, I think our biggest risk is losing our humanity. I really hope the next batch of leaders coming out of HBS will have at their core: how do we make sure AI is a tool that serves humanity well?

PB: Where do you fall on the role of business in society, purely maximizing shareholder value, or a wider obligation to be a positive force in the world?

BR: I’ve always seen massive value creation in breaking false dichotomies. The notion that you can either maximize shareholder value or do the right thing is a totally false dichotomy. It’s truly about near-term versus long-term. In the long term, taking good care of your customers and making sure your products are safe, how can that not be in the long-term interest of shareholders? The question is what about the near term.

Now, focus matters. You can’t solve all the ills of the world. With Pinterest, we’ve looked at youth online safety and said: we can prove that a more positive alternative exists, we can prove better is possible. That’s where we’re going to make our impact. And when there’s a trade-off between short-term and long-term, we’re going to choose what’s in the long-term interests of our users because I fundamentally believe that is also in the long-term interest of our shareholders.

PB: How did you manage the backlash from the under-16 decision, internally from employees and externally from the board?

BR: Looking back, it was actually core to how we ended up winning with Gen Z. Yes, we were doing great things on shopping and recommendations, but Gen Z was also looking for a safer alternative, a place they understood had their well-being in mind. Now it seems obvious, in the same way that a social feed inside Venmo seems obvious now, but it sounded crazy when we first did it.

I went to my board and said: this is what I think we should do, and here’s the bet I’m willing to make. One, it’s fundamentally the right thing. It’s in our long-term interest, otherwise this is going to catch up with us later. Two, I’m making a bet that there’s going to be real consumer demand for this. I used the seatbelt as my analogue: it’s not that long ago that major auto manufacturers said seatbelts were against the business model. Then Volvo invented the three-point safety belt, built a brand around safety, and showed that consumers will choose safety. My board backed me.

Then I had to bring the same conversation to our employees. I didn’t have to convince them it was the right thing to do. I had to convince them it wasn’t going to ruin the company or their career track. People inherently want to do the right thing, but they also feel the pressure of: I’ve got to deliver on my OKR, and if I don’t, my career track is messed up. That was a good amount of work, but it was work worth doing. What’s right isn’t always popular, and what’s popular isn’t always right.

PB: When you walk into a new role knowing changes need to be made, as you did at Pinterest, how do you build trust and credibility?

BR: You have to do a lot of listening first. People need to feel heard. Pinterest was rapidly declining in users when I came in, a dire situation, but you still had to listen first.

As I was listening, I was solving for two things simultaneously: people need to feel heard, and I’ve got to figure out what Pinterest’s real core competency is, what it can do that others either can’t or won’t. Once I’d done that, I moved quickly and with conviction: this is who we’re going to be, this is what we’re going to stand for, and I’ve heard it from all of you. But then I also addressed directly: here are all the places where we’re not doing that, and here’s what we’re going to have to stop doing. We had to reduce staff and cut a lot of projects. There was a culture of letting a thousand flowers bloom, but if nobody curates the garden, the weeds win.

That sequencing really mattered. And the last thing I’d say: that work is never over. One of the best pieces of career advice I ever got was a rhetorical question from an early mentor: “Bill, with whom do you choose to build your army: the conscripted, mercenaries, or freedom fighters?” My instinctive answer was freedom fighters. And he said: not everybody gives that answer. Freedom fighters are way harder to manage. They will call you on your nonsense in a second if you’re not authentic to the mission. A lot of people choose mercenaries because they want people who are easier to manage. But if you have a mission that matters and you’re true to it, nobody will give you more than the freedom fighters. Alignment doesn’t mean unanimity. You’re never going to get unanimity. You need enough listening that people feel heard, but then you have to have clarity, otherwise you’re rudderless.

PB: When recruiting, how do you identify the freedom fighters? Is there one trait or question you’d look for?

BR: Part of how you tease it out is being really clear about what you stand for. Strategy is as much about what you’re not going to do as what you are going to do. And there’s a related point: you don’t really know what someone’s values are until it costs them something to stand by them. So I look less at what people say their values are and more at what they do when it costs them something. That’s when you really see it expressed.

PB: Lastly, there is a perception that AI could fundamentally threaten the existence of something like Pinterest. What do you think about the consumer of the future in a world of AI, and where does Pinterest fit in?

BR: AI is already having a massively consequential impact, and there’s a lot of good it’s doing. Basically everything you see on Pinterest, we’re using AI to make better: more relevant recommendations, using AI to be additive rather than addictive.

But people are fundamentally rethinking their relationship with technology in a way none of us has previously seen. They’ve already lived through social media. You just had one of the largest settlements in US history (Meta), right behind big tobacco and the BP oil spill, for knowingly harming kids. So people are saying: the last decade of stuff that was promised to be so good for us did some good things, but also some really bad things. And they’re already seeing it with AI. I could never afford a tutor growing up. A world where everybody gets a personal tutor is an amazing thing. But then you also see examples of AI helping people commit atrocities. 

The most fundamental question is what distinguishes humans from every other species? We are toolmakers. Is the AI the tool for us, or are we input for the AI? If we as tech companies can’t answer that clearly, can’t make a compelling case for how this is going to make someone more prosperous, then consumers should continue to feel negatively about it. One of the biggest places where people get meaning and purpose is from the work they do. How is AI actually going to enhance human creativity and human ability? It clearly can be that. But I don’t think the case has been made compellingly enough. That’s incumbent on tech companies to solve.

As things become more scarce, they become more valuable. In a world of AI-generated content, authenticity is being valued far more. We see counter-trends on Pinterest, with people craving analog experiences. Digital detox is a massive trend. We as tech leaders have to do a better job of showing that this is a great tool for humanity, not something that sees humanity as input for its purposes.

PB: Very well said. Thank you so much for your time Bill, from myself and the Harbus.

Bill Ready is the CEO of Pinterest, leading the company since 2022. He champions a more positive and purposeful internet, positioning Pinterest as a leader in responsible AI, online safety, and digital wellbeing, particularly for younger users. Previously, he held senior leadership roles at Google and PayPal and served as CEO of Braintree and Venmo. He also serves on the boards of Visa and Williams-Sonoma and is a strong advocate for purpose-driven leadership, innovation, and diverse teams.

Pranav Bharadwaj (MBA '27) is from London, UK. He studied Economics & Management at the University of Oxford before beginning his career in consulting at OC&C. He then moved into healthcare operations, most recently serving as Head of Strategy & Operations at Cera, one of Europe's fastest-growing health tech companies. He is the current CEO of the Harbus News Corporation.