_________________________________________________________________________________________ David
Cannon | Block
As fintech companies grow, legal complexity rarely increases in a straight line. New products bring new obligations. Regulators increase scrutiny. Customers raise new expectations. What starts as a payments platform can quickly become a business operating across lending, music, bitcoin, and financial services. For legal teams, the challenge is not just identifying risk. It is about helping the business understand which risks matter and how to move forward.
At Block Inc., David Cannon has seen that challenge evolve firsthand. Block grew from its roots as Square into a portfolio including Cash App, Afterpay, TIDAL, Bitkey, and Proto. All share a mission: increase access to the global economy and drive economic empowerment. As Litigation Counsel, David handles a wide range of matters at Block.“ They’ re really varied. Some matters involve large regulatory investigations and litigation. Others are partner disputes or customer issues. They can be small, but they’ re never dull.”
The role has grown with the business. When David first joined Square, the legal team supported a much smaller company. He has watched Block expand into consumer finance, lending, investing, music, and bitcoin. Growth brought opportunity, but also new legal scrutiny.
David recalls the difference between the company he joined and the one he advises today:“ I remember handling our first deposition. It felt like a big deal at the time. As the company expanded during the pandemic, everything changed. Now, as a financial services provider at scale, we see far more investigations and litigation.”
As Block’ s footprint grew, legal questions became broader and more frequent. For David, though, the core task stayed the same: understand what happened, evaluate the facts, and find the best path forward.
Scale changes everything
Block’ s businesses operate in very different worlds. A dispute about TIDAL’ s music platform brings up different issues than one about Cash App, merchant payments, lending, or bitcoin. David finds that variety shapes how he works:“ You must take each case as it comes and evaluate it on its own merits. Then you develop the strategy to advise your client and, hopefully, reach a good outcome. It’ s fascinating. You’ re working on different things all the time.”
Variety alone does not make the role challenging. The harder question is determining how legal teams should respond as new products, technologies, and regulatory expectations emerge. For David, that starts with changing how lawyers think about risk itself.
Finding real risk
Supporting innovation means recognizing that not every risk requires action.“ Litigators can always find a risk, and there are always risks. The key is to know which ones are real. It’ s easy to say no, but you’ ve got to be realistic about whether that’ s really warranted, or whether you can tell the business there’ s a risk here, but it’ s not a big one.”
The question is not whether uncertainty exists. In a company operating across multiple regulated industries, it always does. The challenge is deciding how to respond to it. Legal teams cannot eliminate uncertainty, but they can help the business understand it.
Gibson, Dunn & Crutcher LLP._______________________________________
David is the ideal client partner. He has a great feel for strategy and tactics, sees around corners, and sidesteps potential problems before they develop. Efficient, practical, and business-focused, he is a strong leader who helps everyone around him give their best. We’ re proud to call him a client and friend. modern-counsel. com 65