Mallun Yen has spent most of her career feeling like an outsider. She started out as a patent litigator, before making a leap to the tech sector for an in-house role. Two years later, she landed the Chief IP Counsel role at Cisco. It was a prestigious title, and the job looked great on paper. But once again, Mallun’s gut told her it was time to make a move.
Like many creative thinkers we’ve interviewed on CZ and Friends, she bet on herself and became a founder. Along the way, Mallun also became an angel investor for other “outsiders” with big ideas, and it’s become something much bigger than she initially imagined.
"Being an outsider can be a benefit and can give you a fresh perspective,” Mallun said. “Sometimes knowing too much makes you think inside the box too much. You want to know enough to be dangerous, but not so much to be too jaded."
Today, Mallun runs Operator Collective, a venture fund backed by over 250 operators who have built and scaled companies like Salesforce, Stripe, and Google. She is also the founder of RPX, a patent risk management company that went from zero to $100 million in revenue and public in three years. And she still is, perhaps a little reluctantly, a lawyer.
GC AI founder Cecilia ZIniti and Mallun have been in the same legal circles for many years, and in this conversation, they discuss what the “outsider advantage” looks like in practice, building around collective intelligence rather than individual brilliance, and why Mallun has come around to the idea that lawyers make great founders.
Know Enough to Be Dangerous: How Lawyer Became Founder
For a long time, Mallun didn't want anyone in her investor circles to know she was a lawyer. She wanted to be known as a founder and an investor. Her identity as a lawyer felt stifling; she felt it was a signal that sent people's minds in the wrong direction.
"For a long time, I didn't even want to tell anyone I was a lawyer because I wanted to be known as a founder. And then I realized: you know what? Lawyers make some of the best founders," Mallun said.
She began thinking back to how each step in her career had prepared her for the next. As a patent attorney, she learned to dissect ideas down to their essential claims, and consider what someone else might pick at. She also learned how to sit with engineers, ask thoughtful questions, and get to know the minutia of a product. All of these are crucial skills for a successful founder.
Mallun realized she had been every kind of lawyer in her journey to entrepreneurship, including intern in a district attorney's office, federal law clerk, litigator, tech transactions attorney, in-house counsel, outside counsel, government attorney, and finally, startup GC. That diverse experience taught her adversarial thinking, precision with language, and an obsession for small details. When she put all of the pieces together, Mallun finally understood that being a lawyer had taught her how to think like a founder, little by little.
"As a lawyer, we are taught to dissect everything,” she said. “What are all the things that could possibly go wrong? You can't let things fall through the cracks. What is somebody else gonna pick at? I think it's great training for being a founder."
Using ‘Outsider Advantage’ to Build Something Different
Every major career move Mallun has made was one that people said was a bad idea. She left patent litigation during the heyday of patent cases to move to a small tech transactions practice. Then she left Cisco's chief IP counsel role, a job people stay in for decades, to co-found a startup. She built a venture fund with 250 operator-founders when everyone in venture capital said managing that many executives was impossible.
In each case, the people advising against Mallun’s move knew more about how things had always been done than she did. That was exactly the point.
"Had I been in venture, I might have said, oh yeah, that's not gonna work. And I just wouldn't have done it,” she said. “But I could rebuild it from the ground up to optimize for operators. I knew enough about venture capital to know you've got to comply with the regulations, but then I could rebuild it."
Mallun used this ‘outsider advantage’ strategically as she built Operator Collective. She knew what founders needed because she had been one. She knew what operators could offer because she had been one of those too. She didn’t know the “traditional way” venture funds were supposed to be structured, and she didn’t particularly care. She was building something from the ground up, optimized for a group of people the existing model had never been designed to serve.
"Sometimes it's good not to know, because if we knew how much work it was, we might not have done it," she said.
This wasn’t the only time Mallun had used what she didn’t know to her advantage. Several years before Operator Collective, Mallun co-funded an organization called ChIPs with six other women who were chief IP counsel at major tech companies in 2005. None of them had planned a conference before, but they decided to plan one anyway. The organization now has 30 chapters worldwide and 7,500 members, and all because seven people didn't know enough to be discouraged.
Note from CZ: The ChIPs story is one of the best examples of strategic productive naivete I've heard. Seven women at the top of their field decide to have lunch, and plan a conference without any experience planning one. They had the grit and audacity to do something they’d never done, and avoiding the “traditional way” made all the difference.
Building the Fund That Everyone Said Was Impossible
When Mallun left Cisco to found her risk management firm, RPX, she learned quickly that an entrepreneur’s success largely depends on help and support from the right key players. She also learned that getting that help was inefficient, fragmented, and mostly inaccessible to the people who needed it most.
Mallun couldn’t readily find a solution to that problem, so she built it herself. Operator Collective is an atypical venture fund, by design. A community of over 250 experienced business scalers, Operator Collective is made up of former executives from Salesforce, Stripe, Google, and other tech giants who can offer founders the distributed expertise no single investor can replicate.
Everyone in the venture capital space told Mallun her model was completely unmanageable. Fortunately, she didn’t know enough to be discouraged and kept going anyway.
"The collective is always stronger than the individual. It's not just one plus one equals two. It's one plus one equals a thousand,” she said. “When you can bring together incredible people who are so busy, and make it easy for them to participate, it's a multiplier."
Operator Collective’s unique model also reflects Mallun’s personal ethos. She doesn’t consider herself a public figure and doesn’t care to be a social media influencer or the face of her brand. Instead Mallun prefers to point to the extraordinary people around her and say: look at what we can do together. To that end, she also looks to back other “outsider” founders who may not fit the ‘traditional’ founder profile.
"Look beyond the usual suspects,” she said. “When you do too much pattern recognition, you miss the people who don't look like the usual suspects: who can bring something amazing to the table because they're an outsider."
Finding Your Superpower and Building Around It
Mallun's advice for lawyers interested in entrepreneurship is to figure out what you know more deeply than anyone else. Then, own that superpower and build around it rather than spending all of your energy trying to ‘fix’ what doesn’t come naturally.
For Mallun, that meant being honest about who she is. She is not a self-promoter. She’s most comfortable building communities, connecting people, and pointing to the collective rather than the individual. She created the very organization she wished she’d had when her founder journey first began.
"Everyone out there has a superpower. Own it and lean into it,” Mallun said. “There is something that you know and you love and really understand more deeply than anyone else. Just find out what that is, because you all have it."
Mallun’s mission to build community for other outsiders is deeply rooted in her family history. Her father was an immigrant engineer who etched circuit boards in the garage, held patents, and sent a pitch to Sequoia that generated a rejection letter she only found after he died. Mallun leans on collective intelligence because she had watched one person try to do it alone and struggle. She wanted to build a tech community that would have been welcoming to her father, and other “outsiders” with unique points of view.
What AI does for lawyers, Mallun argues, is create the space to lean further into their superpower. The analytical depth, the precision, the ability to dissect a problem from every angle are the things that make lawyers uniquely valuable. AI handles the research, the drafting, the document review, but it can’t replicate your brain, build the framework from legislative history when there is no precedent, or found the company that solves the problem you have been living inside for 20 years. If you’re ready to lean into your unique superpower and start building faster, try gc.ai for free.
