Alex Su @heyitsalexsu

A Biglaw associate once used cold calls to build up a niche specialty in an exclusive practice area and ended up creating one of the most important legal media companies in the world. Here’s his story:

1:58 PM ∙ Dec 21, 2021

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I love stories about lawyers who have done extraordinary things. During challenging times as a young lawyer, I’d read their biographies obsessively, hoping to gain insight into how to navigate my career. I’d file their stories away in my mind, and use them as a roadmap on how to move forward.

One of the stories that has always stuck with me is Tom Goldstein’s. Today I’d like to share his journey, not only because it’s motivational, but because it was one of the stories that ultimately helped me decide to leave the practice of law to go into legal tech. Which, by the way, I’m still in the middle of telling—and I promise the next part will be out soon!

You can’t really understand The Why behind my decisions without Goldstein’s story though. Which, yes, is about encountering setbacks and blazing your own trail. But more than that, it’s also a story about an outsider who struggled to fit in, who ignored established customs and traditions, and who earned the mockery and scorn of insiders. And in doing so, created something incredibly, absolutely wonderful.

This is Tom Goldstein’s story.

What Is SCOTUSblog?

Let’s start with the basics first. If you don’t know what SCOTUSblog is, just ask any lawyer or law student. If you’re too lazy to Google it, let me help you: It is the foremost authority on and the most influential website covering the U.S. Supreme Court. The website receives an enormous amount of web traffic, especially around the time notable opinions are released.

But more than that, SCOTUSblog has attained enormous relevance within the legal profession:

In fact, many news organizations no longer bother sending reporters to the Court, because they can get what they need off the blog. (source)

I’d argue that SCOTUSblog is the most influential law-related media company, hands down.

It was never designed to make any money.

The Beginning

Tom Goldstein was a terrible student in college. His grades were so bad that when he applied to law school, not a single school accepted him.

That person went to the law school's director of admissions and pleaded on Goldstein's behalf. "He said, `This is my favorite cousin, Tommy, and I think he'd be a really good law student,'" Goldstein recalled. "And they admitted me to the evening program." (source)

Unlike his future colleagues at the Supreme Court bar, Goldstein did not spend his summers working in Biglaw. Instead, he spent 1L and 2L summer interning for Nina Totenberg, who was the NPR’s Supreme Court correspondent. That internship, by the way, ended up helping him land a federal clerkship on the D.C. Circuit, which then helped him get a job at Jones Day in Washington D.C.

The Jones Day job wasn’t perfect. Goldstein was passionate about constitutional law, but most of his work there involved the drudgery of commercial litigation. Anyone who’s worked in Biglaw knows. You’re responsible for billing a million hours doing all sorts of mundane tasks. Goldstein found a way to carve out time to do what excited him though.

Making Big Things Happen With Cold Calls

Goldstein would go into Lexis/Westlaw, and start researching circuit splits or circuit conflicts.

“Some people like to play basketball, some go to movies. Tommy likes to do circuit splits." (source)

Goldstein then took it a step further. When he did find a circuit split, he cold called the lawyers who represented the losing party. As he later said:

“People have never viewed the Supreme Court as a place where you can use legal salesmanship to reach out and find cases.” (source)

Goldstein was a fourth year associate when he shared this quote. I wonder how many ex-federal clerks & Biglaw associates have the ability to make cold calls. I mean, his pitch must have been pretty simple: “Let me, Tom Goldstein, handle your complicated case for free.”

And it worked. Goldstein quickly got several of these attorneys to say yes. As one of them later recounted:

“We were very, very busy at the time. It was a major case…There were a lot of issues we weren't very expert in…And so I was thrilled." (source)

After his fifth successful cold call, Goldstein decided that it was time to tell the bosses. This was around 1996 or 1997, so he was still very junior. Goldstein asked the partners for permission to argue the case—on the off chance that the Supreme Court decided to take the appeal.

The higher ups had other thoughts:

As a kind of consolation prize, the partners at Jones Day agreed to put him on track to argue a Supreme Court case eventually--by first having him argue a number of appellate cases, then working his way up to the big show. It was a reasonable offer, but absurd in its own way. Goldstein reckoned that, had he accepted, it could have been more than a decade before he finally argued before the Court. (source)

What followed will give you insight into how Goldstein approaches setbacks.

Quitting Biglaw With Nothing Lined Up

What Goldstein did next was completely unexpected and something that would likely horrify most lawyers in his situation:

He quit Jones Day in 1997 without so much as a single job interview in hand. It took him a few weeks to line up an offer at another firm--"long enough to make my wife nervous," he said. (source)

But then, through a combination of luck and circumstance, Goldstein landed a job at David Boies’ firm, Boies Schiller. Boies was at the time arguably the top trial lawyer in the country, and he asked Goldstein if he’d like to join the firm’s Washington D.C. office.

Let’s level set for a second. Because the Boies Schiller of today looked nothing like it looked in 1997. David Boies had just left Biglaw powerhouse Cravath Swaine & Moore to open his own practice with Jonathan Schiller. It’s unclear to me if the firm had more than a handful of lawyers at the time. But this quote from Schiller highlighted the firm’s philosophy and why Goldstein decided to join:

We were aware that a number of lawyers in private practice were expressing a lack of satisfaction in their work. We also knew that partners in various settings were unhappy with their firm’s management, including . . . partners pulling their associates up through their systems – all kinds of things that had become too standard in the law business. (source)

In other words, it was the complete opposite of Jones Day. It was full of opportunity and upward advancement. It was a great environment for an ambitious, up and coming lawyer who wanted to do big things without waiting too long.

And that’s what happened. Within two years, Tom Goldstein was able to second chair the case on behalf of Vice President Al Gore in Bush v. Gore challenging Florida ballot counts. David Boies served as first chair, and Goldstein was responsible for managing all of the lawyers, organizing filings, and “did some writing.” It was as high profile of a Supreme Court case you could work on.

Goldstein was just 30 years old.

Walking Away From It All To Go Solo

At this point, I think many of us would’ve paused to take stock. Goldstein was five years out of law school, had a prestigious clerkship on his resume, and had worked on a massively high profile Supreme Court case. I don’t know about you but I might have counted my blessings and protected what I had. But at this moment Goldstein decided to strike out on his own, and hang up his own shingle.

It’s important to point out why he made this decision. It wasn’t to make a lot of money, although I’m sure he was aware that he’d capture most of the upside by running his own business vs. working in someone else’s. The real goal behind going solo was to double down on what was working:

“I just decided that I really wanted to be able to focus; and if I didn't go out on my own, it would always be just a side show to what I was trying to do," he said. "I knew if I really wanted the opportunity to do this, I was going to have to give it a whirl.” (source)

It made sense. If you work at someone else’s firm, it’s hard to specialize in such a narrow practice area if there’s limited demand. You’d have to work on other stuff in the meantime. Maybe you’d have to manage discovery or even worse, run doc reviews. Boies Schiller probably paid well, but they needed associates to work up cases, even if it had nothing to do with the Supreme Court.

Note: It’s also interesting to note how focus comes up again. Subscribers will recognize that theme from the Wilson Sonsini origin story I shared recently, where Larry Sonsini decided to focus on startups instead of serving the (ostensibly) more lucrative institutional investors that funded them.

Another, More Personal Note: The story of Tom Goldstein going solo was one of the reasons I decided to go solo myself. I mean, yes, there were multiple reasons behind that decision. But Goldstein’s story helped. He gave me at least one data point that showed why hanging my own shingle could work.

Back to Goldstein: It should be clear by now that he is an entrepreneur at heart. I mean this is a guy who hustled his way into law school after getting rejected everywhere, and who cold called his way into becoming a Supreme Court specialist. He’s not going to wait for things to happen—he’s going to make things happen.

Success Draws Out The Haters

Of course, like most solos, the first few years were hard. Goldstein, who launched his practice from the laundry room of his house, reportedly earned $15,000 in his first six months. I have no doubt the day-to-day was tough. Going solo was completely off the beaten path and likely the least prestigious of the many options he had at the time.

But within a few years, things were humming along. His wife, Amy Howe, joined the practice a year later, and things really took off. By year five, it was clear. The firm was a financial success:

Last year, Goldstein & Howe raked in more than $1 million in revenue, Goldstein said. (source)

Despite this success, not everyone was a fan of Goldstein’s approach. His colleagues and peers who practiced before the Supreme Court ridiculed him. Not only because he went to a lower-ranked school which is highly unusual for someone who litigates before SCOTUS. It was probably his whole mentality, philosophy, his approach to the practice of law.

One of the country’s leading Supreme Court litigators at the time, John Roberts, who would eventually become the Court’s chief justice, made fun of Goldstein, saying:

“If I’m going to have heart-bypass surgery, I wouldn’t go to the surgeon who calls me up.” (source)

It wasn’t just Roberts:

Former Justices William H. Rehnquist and Sandra Day O'Connor were known to look pained when presiding over Goldstein cases. Many of the clerks themselves--some of the top legal minds in the country, who exert enormous influence behind the scenes--apparently feel the same. Each year, they perform an annual revue, in which they impersonate the justices and a small number of unofficial fixtures at the Court. It is a sign of both his status and the scorn he evokes that Goldstein has merited his own personal roasting. (source)

Even Goldstein’s own supporters gave him backhanded compliments. According to Harvard law professor Larry Tribe, who worked with Goldstein in the Bush v. Gore case, and was undoubtedly trying to praise him, threw some accidental shade:

“Even though [Goldstein’s] background was different from people I usually hire, when I met him I was very impressed,” Tribe says today. “His background is irrelevant. He has the intellect, judgment and insight to be absolutely first-rate. He doesn’t have an inflated ego that people with even half of his experience have.”

I mean look, Goldstein was probably self aware enough to know how he was perceived. It wasn’t just the cold calls or his resume. It was what he represented. Which was a proactive approach to breaking into this clubby, exclusive world where others thought he didn’t belong.

“It was incredibly controversial in the beginning,” Goldstein recalled. “I stood for things that they didn’t like. I think they were very comfortable with an elite Supreme Court bar. I didn’t know enough to care. I was so completely on the outside, that the acceptance of this group meant nothing to me.” (source)

I love that last sentence. To me it represents exactly what made everything possible.

The Creation Of SCOTUSblog

In 2002, just a few years after going solo, Goldstein and his wife Amy, who had joined the practice as his partner, made a website to help with business development.

They did it for the same reason Goldstein took cases pro bono: If they were viewed as experts on the court, they thought that might draw in clients. (source)

This is where you can probably see why this story resonates with me so much today, in 2021. There are so many parallels to my own career. Because I started off in legal tech by cold calling potential clients, and then eventually moved to content creation on social media for business development. Which led to something completely wonderful and unexpected.

I digress. Back to the main story:

Over the years, Goldstein has shared how much it costs to keep SCOTUSblog up and running. It’s not exactly cheap.

Which makes me wonder: Why exactly has the website been so successful?

Well, for one, it has always filled a gap in the media landscape. When SCOTUSblog was first launched, there was no dedicated resource that covered the Supreme Court back when it was founded in 2002. As Goldstein shared with CSPAN a decade later:

And yet with all of the coverage of Congress and the President, there was no place that was playing complete attention to what the justices were doing. There was just a gap. It was just an opportunity. (source)

This is a great quote because it highlights the same pattern throughout Goldstein’s career. He identified a gap, and moved into the space. And he made the bet with his own money, his own reputation.

You could imagine what it might have been like if he approached VCs or investors back in 2002 and pitched them the idea of creating this website. They would have thought he was insane. The market’s not big enough. There’s no established model of success. You didn’t go to the right schools. You’re crazy, they might have said.

I mean, it’s probably not unlike how they thought he was crazy in 1997. For cold calling potential clients and handling cases for free.

But ultimately, there is one more part of the recipe that I believe doesn’t get enough coverage. It’s not just about the money. SCOTUSblog, and all of Goldstein’s Supreme Court work appears to mean much more to him than just money. You don’t plug away for decades, get hated on by the justices & by the other members of the bar, and do something crazy like launch a website in your niche practice area. There are easier ways to get rich.

Just look at all of the other Biglaw firms that handle Supreme Court cases. They have more money, more resources, and a ton of lawyers with elite resumes. Why haven’t they been able to do the same? I think your motivations have to be more than just about ROI or money.

You’d have to do it for the love of the game.

Of course, I have no idea if this is actually true. I’ve never spoken to Tom Goldstein. And yeah, maybe I’m just reading things into this story, seeing what I want to see. But I like to think that the best summary of Goldstein’s intentions comes from someone who knows him well, and who’s known him for many years: His wife Amy.

“I think of SCOTUSblog as my beach house,” she said. “It’s expensive. But we feel like it’s a public resource, and it’s too much fun to stop.”

Thanks for reading! Let me know if you have any feedback or what you think. I plan to write more about lawyers who are doing awesome things with their law degrees, because they help explain why I decided to go into legal tech to pursue an unconventional career. Subscribe if you’d like to follow along!