David Felicissimo
5 min readMar 10, 2016

The Practice of Law as a Springboard:

The Curious Cases of Chris Sacca and Mitch Garber.

This April will mark the 15th year anniversary of my law school graduation. Like most law students, I went through several stages vis-à-vis my career ambitions from becoming a prosecutor to working with an NGO and eventually ‘settling’ for a coveted spot at a national firm. However, since 2008, I find myself General Counsel for a technology company in a position years away from where I began my career.

Entering a company as General Counsel one quickly realizes that the skills ‘acquired’ in law school and in a legal career can (if used correctly) be extremely useful as a springboard in business. As many can attest, being General Counsel is much more than purely being a lawyer. A General Counsel is the trusted, go to advisor which both heads of departments and shareholders will confide in. In certain instances, this background and experience can be a valuable asset to take on a greater role within a company.

I recently came across two individuals, each a very unique career trajectory, which offer an interesting insight on how law school and early years in the practice of law can be the quintessential springboard into a completely different and successful career.

Namely, Silicon Valley venture investor Chris Sacca and Mitch Garber, CEO of Caesars Acquisition Company.

Chris Sacca founded ‘Lowercase Capital’ arguably the most successful venture capital fund in Silicon Valley. Recently, he has appeared as a guest on a few episodes of ABC’s Shark Tank. Chris Sacca’s ascent into the venture capital is one of the most interesting I have ever come across.

Chris attended Georgetown University Law School and managed to graduate with top grades without attending classes. From there, he joined Fenwick & West in Silicon Valley only to be let go with his entire graduating class four days before 9/11.

He spent the next few years expanding his ‘contact list’ by attending every networking event possible and ‘surviving’ in Silicon Valley. This included everything from drafting contracts for 50$ on craigslist to voice over work on sites such elance. He eventually landed at Speedera Networks and later joined Google. Although officially hired as Corporate Counsel reporting to General Counsel David Drummond, Sacca got hired as they were looking for a lawyer with knowledge in data space to negotiate and purchase data centers across the country. Sacca excelled at Google even winning the ‘founders’ award early on.

After leaving Google in 2007, Sacca founded Lowercase Capital and through a series of early investments in Twitter, Uber and Instagram has managed to create what is regarded as the most successful fund in Silicon Valley.

While Sacca’s success can be attributed to various factors including his experience at Google and entrepreneurial drive, law school helped ‘fast track’ him where he wanted to be. In a podcast interview with Tim Ferriss, Sacca explained “I went to law school because I thought it was the fastest path to a seat at the table in Silicon Valley and wanted to be in the middle of the deal to have people listen to me.” A law degree from Georgetown enabled him to join one of the most prestigious law firms in Silicon Valley where he handled venture capital, mergers and acquisitions and licensing transactions for technology clients such as MacroMedia and Kleiner Perkins.

Sacca has indicated time and time again in various interviews that it is important is to make yourself useful to founders, having skills from being able to draft contracts, advise on a corporate structure or even negotiate with third parties all picked up in a legal practice is no doubt part of being helpful.

Mitch Garber is another interesting example whose path from law school to his present role was almost set in stone early on.

Garber graduated from the University of Ottawa with a Civil Law Degree and began specializing in gambling law for a boutique firm. It was here Garber learned about the gaming industry and when the internet opened many business opportunities in the late 90’s he was in a position of having deep knowledge of the industry in relation to the internet.

He later left the profession to join SureFire Commerce Inc., a NASDAQ-listed payment-processing company whose clients included all major licensed online gambling sites around the globe. After corporate re organizations he was CEO of the newly formed Optimal Payments Inc. In 2006, he moved to the pinnacle of the industry when he was appointed head of the world’s largest online gaming company PartyGaming PLC.

Since 2009, Garber is CEO of Caesar’s Acquisition Company, head of Caesar’s Interactive Entertainment and since last year Chairman of Cirque du Soleil.

Garber’s knowledge into the legal, financial and technological aspects of gambling can be traced to his early years as a lawyer. As such, use of his law degree and experience as a lawyer was the perfect ‘jump start’ for his rise to the most coveted position in his industry.

Traditionally, a law degree has been undervalued in the business world and companies are reluctant to see their General Counsel in the same light as business executives. Typically, lawyers begin their careers in a “world” where risk is frowned upon and decisions are only made after thorough analysis and paperwork. Entering a company, General Counsels are often regarding as ‘deal breakers’ for their caution and being risk averse which ‘throw’ cold water on deals. The perception is that there is an obsession with details, which makes them, fail to see the larger pictures. I have often witnessed entrepreneurs claim lawyers will lack the bold vision, marketing skills and financial savvy to lead a company.

In reality, law schools with its entrance exam and limited admission is typically made of ambitions and intelligent individuals that have already made significant academic achievements. A legal career further allows them to be at the heart of important matters in a relatively short period of time and get a broad understanding of a specific vertical be it technology, venture capital, etc. A General Counsel (or even outside) is actually in a unique and privileged role in a company giving them an all around understanding of both operations and management while attaining an unmatched level of trust among all sectors of the organization. This allows one to foresee both managerial and operational issues that may arise from certain decisions.

Collectively, this is the perfect ‘training ground’ to enter specific verticals and succeed.