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May 26, 2024
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Steering the ship through a fintech revolution, controversies, and more


On a cloudy mid-October day at PayPal’s (PYPL) New York City headquarters, I find Dan Schulman — who I’ve been getting to know beyond the standard reporting stuff for close to seven years — a wee bit more relaxed than usual.

To be clear, Schulman, 65, is often on the cool, calm, and collected side — the most outwardly relaxed and mentally present public company CEO I’ve ever encountered. He literally wears his down-to-earth leadership philosophy.

I’ve told him countless times I’ve never seen him in anything other than his trademark black shirt, light blue jeans, and brown cowboy boots that surely hide his well-toned, Krav Maga-produced physique (I have never told him about the last part…).

At first, I thought this chiller-than-norm vibe was a reflection of him rallying back from an emergency appendectomy a couple weeks earlier.

Former PayPal CEO Dan Schulman (right) reflects on his leadership journey inside the PayPal NYC headquarter he opened with Yahoo Finance Executive Editor Brian Sozzi (left).Former PayPal CEO Dan Schulman (right) reflects on his leadership journey inside the PayPal NYC headquarter he opened with Yahoo Finance Executive Editor Brian Sozzi (left).

Former PayPal CEO Dan Schulman (right) reflects on his leadership journey inside the PayPal NYC headquarter he opened with Yahoo Finance Executive Editor Brian Sozzi (left). (Yahoo Finance) (Yahoo Finance)

Maybe that’s part of it. But then I realized — after years of taking bold stances on hot button social issues and dealing with complex business matters, Schulman finally has a few extra minutes in his week.

His last official day as PayPal’s CEO was Sept. 26, 2023, almost nine years after the then top exec at American Express (AXP) took the top gig. Schulman handed his reins to former Intuit (INTU) exec Alex Chriss, 46, after a lengthy search.

With this transition, Schulman is now taking a moment to reflect on his leadership resume.

“I really don’t have any regrets,” Schulman told me in a new episode of Yahoo Finance’s “Lead This Way.”

“I would have regrets if I wasn’t making decisions, if I had felt like, ‘OK I need to be really cautious now and not make difficult decisions,'” Schulman added. “But I think as leaders, you need to be quietly confident in your ability to take in as many facts as you can. You’ll never have all the information you need, but you must make decisions and move forward.”

About that resume…

Before PayPal, Schulman served in big-time leadership roles at AT&T (T), American Express, and Priceline. He even helped launch Virgin Mobile with Sir Richard Branson shortly after the Sept. 11 terrorist attacks. The billionaire entrepreneur reaffirmed to him what it means for leaders to take risks and be bold, Schulman tells me.

But no doubt his leadership legacy will be closely aligned with his time atop PayPal.

And rightfully so.

Schulman arguably kicked off a golden decade of fintech in the mid-2010s, establishing a new need to “democratize” financial services for the average person.

Expanding PayPal’s reach beyond store payments to crypto and payment sharing (via millennial brand Venmo) were but a few of Schulman’s achievements.

In the process, PayPal’s market cap surged from $50 billion around the time of its Nasdaq debut in 2015 to more than $362 billion at its peak in the summer of 2021.

The company’s total payment volume is estimated to have hit 1.5 billion in 2023, up from 282 million in 2015. Active accounts have gone from 179 million to roughly 430 million during that same stretch.

Dan Schulman's leadership tips. Dan Schulman's leadership tips.

Dan Schulman’s leadership tips.

Schulman disciples — aka PayPal leaders — have gone on to major C-suite roles elsewhere, such as Walmart’s (WMT) CFO John David Rainey (former PayPal CFO) and Pinterest (PINS) CEO Bill Ready (former PayPal COO).

As PayPal’s profile rose, so did Schulman’s, spurring him to tackle social issues he thought should be addressed by a prominent leader that isn’t afraid to speak out.

None was more headline-grabbing than the decision to cancel plans to open a global operations center in Charlotte, N.C., after lawmakers passed a controversial law targeting LGBT people in 2016.

“The new law perpetuates discrimination and it violates the values and principles that are at the core of PayPal’s mission and culture,” Schulman said in a statement at the time.

Schulman concedes today that the decision to speak out came with unintended aftershocks.

“I felt like that was anathema to our values,” Schulman tells me. “And so we pulled out of North Carolina. I had no idea that it would be front page news of the New York Times. I had no idea the number of death threats that I would get as a result of that and hate email.”

“My view is that our platform should be a platform where you can have civil discourse, where you can raise money for organizations that don’t advocate violence or extreme hatred,” continued Schulman. “You would think there wouldn’t be much controversy of taking down neo-Nazi sites or KKK sites, but there always are.”

The exit — and the path forward

As they say in life, nothing is perfect. And even Schulman had a few bumps in the road retiring from PayPal.

Today, PayPal’s market cap stands around $65 billion, amid slower growth and rising competition from newer entrants such as Robinhood (HOOD), Affirm (AFRM), and Coinbase (COIN), and legacy payment brands like his former employer Amex and Mastercard (MA).

Apple (AAPL) and Google (GOOGL) have also made strong inroads into the payments industry with offerings of their own.

Towards the end of Schulman’s tenure, PayPal was attacked by famed activist investor Elliott Management in the summer of 2022. Elliott demanded cost cuts to offset pressures on the top line and boost the sagging stock price.

The company went on to outline $900 million in cost cuts — mostly through layoffs, real estate consolidation, and project cutbacks. It also uncorked a $15 billion stock buyback plan.

With that situation done and dusted, Schulman and the board got to work on picking his successor.

By December 2023, Schulman left PayPal’s board, with the ship firmly in the hands of Chriss, who’s been in the trenches outlining his plans for the company Schulman took public.

As for what’s next, Schulman hints he has a lot of well-earned options — including “senior” government roles — being offered. He declined to share specifics.

He plans to reveal his next move in the coming months, after taking some time off and assessing the choices with his wife and kids.

“One of the things that I am struggling with a little bit right now is the number of opportunities in front of me and trying to think about what do I want my life to look like going forward,” Schulman says. “I feel no pressure in making a lot of decisions right away.”

Wherever Schulman ends up, this journalist thinks a black shirt, light blue jeans, and cowboy boots won’t be too far behind. That and the teachings of Krav Maga and learnings from a life in the C-suite.

Lead this way, catch it weekly Thursday at 3pm ET.Lead this way, catch it weekly Thursday at 3pm ET.

Lead this way, catch it weekly Thursday at 3pm ET.

Brian Sozzi is Yahoo Finance’s Executive Editor. Follow Sozzi on Twitter/X @BrianSozzi and on LinkedIn. Tips on deals, mergers, activist situations, or anything else? Email brian.sozzi@yahoofinance.com.

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