David Stiepleman ’97: ‘Building Things,’ From Adviser to Principal

David Stiepleman ’97 is co-president and co-founder of global investment firm Sixth Street, which manages more than $135 billion in assets, but what he really wants to talk about is the amazing effects of washing the sidewalk.

Since Sixth Street’s founding in 2010, Stiepleman has helped build it into a leading private capital investment firm. He is now applying the same business-building mindset to downtown San Francisco. As chair of the San Francisco Downtown Development Corp. (SFDDC), which he helped found in 2025, Stiepleman is leading a public-private partnership to revitalize a city center hit hard by the pandemic. One of the first solutions, made possible by the $80 million SFDDC has raised: twice-daily power washing of sidewalks around the city’s Moscone Center to encourage needed convention business.

If a convention planner visits and sees filthy streets, “they are going to say no” to bringing their tradeshow to the city, Stiepleman says. “And you don’t know when they’re coming to do a site visit. So it’s got to look good all the time. And now bookings at the center are up more than 60% from 2024.”

The revitalization effort is “awesome,” Stiepleman says, “but it’s step by step. That’s the thing that you learn as a business builder. You learn just as you learn law—as an accretion of things over time.”  

Raising money for the downtown effort involves pitching to business leaders, “being persuasive and being willing to hear no and continuing to refine the rap,” he says. SFDDC’s programs to hire roving “ambassadors” to direct tourists around downtown, to arrange for street cleaning, and to fill vacant storefronts seems quite different from doing M&A law in Brussels, but Stiepleman’s career has gone through several iterations. The connecting thread in all of them is simple, he says: “I’m a generalist, and I like to build things.”  

From Lawyer to Leader

That knowledge was gained in several stages. He began his career at the law firm Cleary Gottlieb, where his introduction to finance came when a senior partner told him to come up with a strategy for a client who wanted to launch a hedge fund. As a first-year associate, Stiepleman could only nod—and then educate himself in a hurry. His focus on deal lawyering sharpened after observing the lead lawyer during a transaction in Ireland. “I watched the senior lawyer also become a general,” he says. That meant commanding the room, he recalls: “He knows enough to ask the right questions, he can write, can think on the fly, can build consensus, knows what the client cares about and what they don’t care about.” 

In the end, he says, M&A deals are about “building something. You start with parties who, though they’re not going to agree on everything, want to actually do something. So the process is constructive.” And once the deal is hammered out—including, he says, foreseeing “how would someone of less than good faith might try and misinterpret the terms, and how do you protect against that”—the deal gets executed in real life. “It’s like magic,” Stiepleman says. “I thought that was super fun.”

Stiepleman met his co-founders when they worked together at Goldman Sachs and continued his evolution from lawyer to “investment bigwig” (according to the San Francisco Examiner) at Sixth Street. He says he relished the opportunity to build a business from scratch and watch the growth of an enterprise that “did not exist before we started working on it. And now it does, and people are making a living and doing interesting things.”   

Along the way, he morphed from lawyer to leader and “from agent to principal.” 

“Until we founded Sixth Street, I was still a lawyer,” he says. “I still had a little bit of that distance where you say, ‘This is what I advise you to do, that’s the best advice in the world, and you should go do that.’” Making the shift into running a business was “a big decision,” Stiepleman says, but he was simply taking his own advice by asking himself, “What do I actually enjoy doing?” 

His inner lawyer remains, however, in his ability to “call B.S. on people’s analysis who are thinking too quickly or too narrowly.” Regardless of his current job title, he says, “You don’t lose that.”

Aunt Ruth’s Example

Stiepleman’s French major at Amherst College wasn’t an indication of a future career in law and business. Nor was the year working in the press office of Democratic Sen. Russ Feingold of Wisconsin. But when he looked for a new direction, Columbia Law School was a compelling choice, thanks to the example of the person he calls “the real Lion of Law,” his aunt, Ruth Bader Ginsburg ’59. The Supreme Court justice’s husband, Martin, was Stiepleman’s mother’s brother. Justice Ginsburg officiated at Stiepleman’s wedding to Carey Lifschultz right after he took the 1997 bar exam.

“She was phenomenal—an incandescent intellect,” Stiepleman says of Ginsburg. “And she was a pretty good aunt as well.” 

Ginsburg’s well-known maxim—that it is possible to disagree without being disagreeable—has stayed with him. “She knew she was probably always going to be the smartest person in any room that she was in, and she was unfailingly nice and patient,” Stiepleman says. “A lot of people could learn something from that.”

At Columbia Law, Stiepleman ended up in a copyright class taught by his cousin Jane C. Ginsburg, Morton L. Janklow Professor of Literary and Artistic Property Law. “There was great interest in the family as to how I was doing,” he recalls. He also loved civil procedure with Jack Greenberg, criminal law with Debra A. Livingston, Paul J. Kellner Professor of Law, and being a teaching assistant for a property law class taught by Curtis Berger. Especially meaningful, Stiepleman says, was a fair housing clinic taught by Conrad Johnson, Edward Ross Aranow Clinical Professor Emeritus of Law. 

In clinics, where law students represent clients, “you’re really playing with live ammo,” Stiepleman says. “These are real people who have a real problem.” The fair housing clinic focused on practicalities, which Stiepleman loved. “Johnson touched on all these issues: What does it mean to represent? How do you actually listen? Taking information, and interpreting that information: What are you listening for? I thought it was great.”  

 The Current Chapter

Listening well is a necessity in Stiepleman’s venture as podcast host. It’s Not Magic, which focuses on “the useful stuff” in building businesses with guests who have done just that, including Daniela Amodei, president of Anthropic, and Tekedra Mawakana ’96, co-CEO of Waymo.  

One thing Stiepleman has learned from his interviews, he says, is that all his guests reached a level of considerable achievement—and then realized they needed to, and could, expand their abilities and scope to succeed at a new level: “Are you self-aware enough and confident enough to realize you’ve got to do something new, and can you figure it out?” he says.

That insight resonates for Stiepleman since his own path has taken him from deal lawyer to investment firm principal to downtown revitalization catalyst. “I’m definitely projecting on my guests,” he says with a laugh.