General Counsel Sydney Brie Schaub Works with Visionary CEOs

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Sydney Brie Schaub has gleaned some unique insights from serving as general counsel of several high-profile companies across a range of industries. She has also learned what it takes to work effectively with visionary CEOs and how to support their disruptive ambitions while navigating legal challenges.

Building an Exciting Career as a General Counsel

Ms. Schaub has had an admirable career. With degrees from Stanford and Harvard Law School, she began her legal career at Google. In 2011, she moved in-house at Jack Dorsey’s Square, when it was a 150-employee startup. Square has recently changed its corporate name to Block. As an Associate General Counsel at Square, she grappled with complex, evolving legal issues that faced the fintech industry.

Ms. Schaub pivoted away from the tech industry and took a position as General Counsel of Rent the Runway. At the time she joined, Rent the Runway was a late-stage private company reshaping the global fashion industry. In 2018, less than 2 years later, she pivoted back to tech and joined Gemini Trust Company as its General Counsel.

She is currently at Gemini Trust and leads its legal, compliance, and government affairs functions. Gemini is digital asset exchange, wallet, and custodian, and has emerged as a leading player in the crypto industry.

Advising Gemini Trust on Crypto Legal Challenges

Founded by twin brothers Cameron and Tyler Winklevoss in 2014, Gemini is a New York trust company regulated by the New York State Department of Financial Services (NYSDFS). This means the company is subject to a variety of compliance standards under New York Banking Law. The NYSDFS also imposes certain cybersecurity and capital reserve requirements.

In addition to its core focus on crypto trading, Gemini Trust also works with non-fungible tokens, or NFTs. In November 2019, Gemini acquired the NFT startup Nifty Gateway. Interestingly, like Gemini, Nifty Gateway was co-founded by identical twin brothers. These steps required the assistance of talented general counsel.

The NFT platform has captivated the high-end art market. In March 2021, because of attention-grabbing art sales on the digital marketplace, Nifty Gateway established a partnership with auction house Sotheby’s. Nifty Gateway sold the first NFT collection through Sotheby’s and fetched $17 million in only three days.

Supporting Visionary CEOs and Outside Counsel

Ms. Schaub explains there is a special spark that attracts her to work for visionary CEOs. “There is something special about being a key advisory to someone who is as invested in the success of their business as its founders are. And I have great respect for anyone who creates a thriving company out of their own idea—particularly Jenn Hyman and Jenny Fleiss, who conceived of and raised capital for Rent the Runway at a time when few women were getting venture capital funding.”

Working for leaders who take on established industries and attempt to reinvent them has its challenges. Deviating from established practices often comes with a new set of legal challenges for general counsel. This is especially the case in regulated industries like fintech, where the legal issues can become front and center to facilitating the business operations.

General Counsel Must Find Out-of-the-Box Legal Solutions for Visionary Leaders

As a legal advisor to a visionary leader, it is important to find legal solutions without stifling the leader’s creative vision. This can be challenging given that disruptive products and services often do not fit within existing legal and regulatory frameworks. A lawyer who can think of creative, out-of-the-box solutions is best suited for this challenge.

General Counsel Out of the Box
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As general counsel, Ms. Schaub seems to enjoy this process. “The audacity of taking on that challenge is incredibly inspiring, and the legal issues associated with the business tend to be front and center, which is fun for me because I like how innovative this forces lawyers to be. Existing law is usually not a good fit for disrupters’ products and services, so we as attorneys have to be creative in applying that law and tenacious in molding and changing it,” Ms. Schaub commented. “Maybe it’s the contrarian in me, but I like that challenge. It’s never been done before? Great: we’re going to do it.”

Business executives can sometimes feel that lawyers are a hindrance to innovation. This is because lawyers can come with disappointing news, explaining the various legal and regulatory roadblocks that stand in the way of implementing ambitious business goals. Ms. Schaub has learned some tips for how to bring up legal concerns without crushing a business leader’s vision.

Among the most important tip is simply demonstrating you believe in the leader’s vision as their in-house lawyer. “When my CEO and President see that I believe in the vision and that everything my team is doing is in service of bringing it about, they’re more receptive to the legal concerns we raise.”

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