Dan Dressman Proves There’s No Substitute for Experience

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Dan Dressman didn’t grow up with lawyers in his family, but from an early age, he knew he wanted to be one. He watched his dad navigate legal issues as a small business owner and was drawn to the way laws impacted people on a day-to-day basis. Also, as a lifelong athlete, he sensed the field aligned with his competitive nature.

Today, Dressman serves as senior counsel of litigation and risk at Lyft, where he’s charged with creating risk mitigation strategies for the Express Drive program that enables people to rent and drive cars for the company. While his winding career path was filled with many lessons, one stands out that permeated each chapter of his journey.

“There’s no substitute for experience and that lesson has been with me from the very beginning,” he says. “I worked a lot during law school, and I didn’t go to a top tier school. The opportunities I was going to have had to be because I took them during the academic year, not just the summer. That’s why I externed at a public defender’s office and the US Attorney’s office and through those opportunities, I got to stand up in court, make arguments, and be around talented attorneys on the defense and prosecutor side.”

“There’s no substitute for experience and that lesson has been with me from the very beginning.”

Dan Dressman

Dressman emphasizes, “As a young attorney, getting experience will get you where you need to go.”

That piece of advice was imparted on him by a mentor in law school and helped him continue to hone his legal skills after getting his JD in 2012. First, he participated in a seven month-long post-graduate fellowship in litigation at his alma mater, where he taught litigation skills to students and served as a coach for the mock trial team. Then, he spent a year at the San Francisco Superior Court as a legal research attorney in the law and motion department, an experience he says was “as foundational as it gets.”

“We had five-days-a-week, twenty-plus matters on our court calendar on every issue you can imagine in San Francisco. We were analyzing issues and writing bench memoranda for the judge to critique,” he remembers. “You talk about litigation and that’s it. You’re analyzing, digesting, and critiquing work from some of the biggest, most elite firms in the city to solo practitioners. You got to see the full gamut of legal writing and how advocacy is done at the highest level.

There’s no substitute for familiarizing yourself with substantive legal issues and procedural issues every day, and even as someone who isn’t on the front lines anymore, I still use that stuff all the time,” Dressman continues.

“This is a tough profession, so be humble, knowing that you’re going to fail, but use it as an opportunity to learn.”

Dan Dressman

From there, the attorney took on another foundational experience at Gordon Rees Scully Mansukhani LLP. Up until that point, he didn’t have plans of moving in-house and was unaware of the kinds of opportunities companies had for a litigation lawyer like him. But after he learned about a friend’s experiences at Lyft who had recently joined the company, it piqued his interest.

“Once, I found out they were handling all sorts of litigation issues, regulatory issues, and product issues, I jumped at the opportunity, and I don’t regret it for a second,” Dressman says. “I had lived through rideshare bursting onto the scene in 2013, it was something I used every day, and the opportunity to work for a company that seemed so new at the time intrigued me.”

He began his tenure at Lyft in 2019 with a portfolio of litigation cases around the country, including issues tied to personal injury, regulatory, and intentional tort. Since then, Dressman has added product counseling and regulatory responsibilities to his plate. A typical day involves coordinating with outside counsel partners to develop, update, and hone litigation processes and tools to defend Lyft’s interests in litigation. It’s a role that keeps him on his toes and allows him to work collaboratively with different stakeholders.

“Prior to my time at Lyft, it wasn’t very often that I was analyzing in new or emerging areas of law. Now, I am frequently crafting strategies to address new case law and new legislation and to support new products,” he says.

While Dressman has seen success in balancing those priorities, he admits that it took some time adjusting to an in-house environment and mindset. “You go from being part of a firm that only deals with niche legal issues to being part of a business,” he explains. “Your role is to support the growth, products, and mission. Your job is to identify what a win is, and that win may be drastically different depending on the issue. It’s been an enlightening part of moving in-house and one that I enjoy.”

“Dan is the whole package: a talented litigator, a leader who truly understands the business and makes the right strategic calls, and a fun person to work with,” says James E. Gillenwater, litigation shareholder at Greenberg Traurig LLP. “It has been a pleasure teaming up with Dan to set precedents in the rideshare industry, which has benefited from his leadership.”

A highlight from his time at Lyft involves being heavily involved with the product launch process for Express Drive.

“In a law firm setting, I wasn’t a part of advice and counsel,” Dressman says. “I was in the courtroom, doing discovery, taking depositions. So, being a part of something new was really great. I’m really proud of how matured our internal processes have become and I think there’s visibility across the legal team and the business.”

Young attorneys who want to follow in the accomplished attorney’s footsteps should not only seek out valuable experiences but should remain humble as they navigate them. “This is a tough profession, so be humble, knowing that you’re going to fail, but use it as an opportunity to learn,” he advises.

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