We recently caught up with Rick Estacio (NY, ’09), Senior Director and Global Head of Commercial and Advertising Legal at Reddit. Rick started as a litigation associate in the Davis Polk New York office, focusing on commercial disputes, regulatory investigations and enforcement. In 2018, he transitioned to in-house practice, first at JPMorgan Chase, then Coinbase and, since 2023, Reddit. In his current role, he leads a team that negotiates agreements globally with Reddit’s advertising, content licensing, tech and AI clients, partners and service providers.
Read on to learn about Rick’s experience in various industries and the strategies that have helped him adapt to new roles.
Tell us about your experience transitioning into and working in different industries, particularly the move from JPMorgan and Coinbase, both finance-related companies, to Reddit.
I’ve consistently found the most success and enjoyment in my career happens when I step outside my comfort zone, because I love the challenge of learning new skills and subject matter. After eight years as a litigator at Davis Polk, I accepted a non-litigation in-house role at JPMorgan. There, despite little prior understanding of the technologies, I volunteered to help advise the bank on asset tokenization and its development of a proprietary blockchain network. That work provided a stepping stone to being hired as product counsel for Coinbase’s institutional client business.
Coinbase went public shortly before I arrived, but it was still very much a rapidly growing Silicon Valley startup. The clients and substance overlapped with those at JPMorgan, but the work environment was drastically different. Outlook and Word were replaced by Gmail and Slack, and pressed dress shirts gave way to hoodies. Organizational charts at tech companies are also generally more fluid than at JPMorgan. On my first day as a product counsel at Coinbase, for example, I agreed to instead head its short-staffed institutional commercial legal team.
At Reddit, my role continues to evolve and expand as the company grows, and I’ve enjoyed every minute of the journey so far. The key to happiness in an in-house role is to work with colleagues who you like and respect, and I couldn’t have asked for more incredible colleagues and business partners than I have found at Reddit.
How did your experience at Davis Polk prepare you for your roles at JPMorgan, Coinbase and Reddit?
Davis Polk’s generalist litigation practice was the perfect place to nurture my natural curiosity. It allowed me to develop an incredibly broad practice representing public companies, financial institutions and auditors in everything from B2B contract disputes to bankruptcies and before state, federal and international regulators. I also spent six months working from Davis Polk’s Hong Kong office and a year as a secondee in-house with JPMorgan, where I led a risk assessment project spearheaded by the general counsel. It was during this secondment at JPMorgan that I discovered my love of in-house work and formed the relationships that ultimately led to my role there.
At JPMorgan, Coinbase and now Reddit, I’ve worked on and led teams of product and commercial lawyers located across the United States and abroad. These lawyers serve as comprehensive legal advisers for the businesses they support, seeking to identify practical solutions to complex real-world problems. We advise on how to design products and structure deals, and we negotiate deal terms. In all this, we are striving to drive revenues and cut costs, while mitigating legal and business risks – such as risks in connection with adopting AI tools, launching new platform features, expanding geographic reach, or entering into partnerships with financial services, media and technology companies.
Working as a Davis Polk litigator honed skills and exposed me to areas of the law that have proven critical in these roles. Spending years litigating B2B contract disputes, for instance, drives home which contract provisions and edits truly matter – and, equally as important, which don’t. And presenting my clients’ positions to judges and regulators ingrained persuasive skills that seamlessly translate to my in-house work.
Tell us about your experience at Reddit, which you joined 10 months before its IPO.
I had an incredibly exciting first year at Reddit, highlighted by Reddit going public! Because we aspired to IPO when I joined, my first year was laser-focused on building a world-class commercial legal department, replete with the personnel, processes, procedures and controls required of a public company signing contracts globally and publicly reporting its financials.
During my inaugural year, I also focused on advising Reddit on the launch of its content licensing business. As our latest 10-K notes, Reddit has one of the largest bodies of information on the internet and that content is particularly important for artificial intelligence.
I would have been lost during my first year without the support of my manager, Milana McCullagh, who I also consider a mentor. She’s intelligent, builds strong relationships effortlessly and draws on decades of experience leading legal teams at top tech companies, which gives her an uncanny ability to instinctively make the right strategic judgments. During one of my first days on the job, I reviewed a “decision doc” intended for senior business leaders, analyzing the pros and cons of different strategic paths forward, and I peppered it with extensive edits (many of which were unnecessary). Milana, seeing my markup, provided two incredibly valuable pieces of advice for starting a new role: She encouraged me to take a beat, learn the ropes and earn trust before trying to impose my viewpoint. And she recommended reading The First Ninety Days by Michael Watkins, which makes the same point.
Building on that last point, what strategies have helped you successfully adapt to new roles and industries throughout your career?
The first is to listen and learn. You’ll add the most value after you’ve put in the effort to acquire an in-depth understanding of your business models, legal processes, strengths and weaknesses within the team, and what’s working and what’s not.
Second, dedicate time outside of work to staying current on industry news. I gain an incredible amount of valuable industry knowledge from podcasts, which I listen to at 1.8x speed for at least 30 minutes every day while walking my dog or riding the subway. Sharp Tech, Dithering and Stratechery, all hosted or co-hosted by Ben Thompson, are a few of my current favorites.
Third, work outside of your comfort zone. Working on matters outside of my job description has been critical to my career development and is what has kept me excited about going to work every single day – well, to be honest, almost every day. Unexpected transitions can be stressful, but when they inevitably happen, it’s important to stay positive and remember transitions create opportunities.
You went on a six-month secondment to Davis Polk’s Hong Kong office from 2014 into 2015. Tell us about that experience.
I loved my experience in Hong Kong. The office was much smaller than New York. Litigation teams of 10+ in New York shrank to two or three in Hong Kong. I fondly remember working with James Wadham, Jennifer Newstead (current Meta CLO) and Raul Yanes on investigations for global financial services companies. When I returned to New York, I continued working on the U.S. components of several matters that I worked on in Hong Kong.
Davis Polk provided housing for me and my wife, Lauren, that was in a wonderful part of the city and within walking distance to the office. Plus, the timing of my secondment allowed me to trade a particularly cold New York winter for warmer Hong Kong weather. I’d highly recommend living and working in another country if the opportunity arises. I frequently travelled on weekends to explore other parts of the Asian continent, and the work provided me with a valuable global regulatory perspective.
What advice have you received during your career that you would pass on to lawyers interested in following a career path like yours?
The most valuable life and career advice I ever received came from my dad when I was young. When I was applying to colleges, he said to set your sights high, unbelievably high, and just go for it. If you hear a voice in your head saying you can’t do it, ignore it. The worst thing that can happen when you try is that you fail. But failure is okay because you definitely won’t reach your goals if you don’t try.
If you’re considering a new job, don’t worry if you don’t satisfy 100% of the listed job criteria. If you want the job, apply. You’ll often find that your work experience has created transferable skills that companies need, even if the connection between your current work and the role you want isn’t immediately obvious.