How to Build a Great Career Without Following the Rules with Mallun Yen

“Sometimes not knowing the rules is the thing that lets you see what’s possible.”Mallun Yen’s life and career have been shaped by not quite fitting the mould — and learning to see that as an advantage.Growing up as the daughter of immigrants, Mallun often felt like an outsider. She spent years trying to blend in, to understand the unspoken rules around her. But over time, she realised that being on the edges gave her a different perspective — one that allowed her to observe more closely, spot patterns, and see opportunities others might miss.Her career reflects that same thinking. From starting as a lawyer, to leading intellectual property at Cisco, to building a company from zero to public in just three years, Mallun has consistently taken paths that didn’t quite follow the traditional route. Not having the “right” background became a strength — freeing her from assumptions about how things are supposed to be done, and allowing her to think differently.In this conversation, we explore the deeper lessons behind that journey — from the importance of relationships and feedback, to the courage it takes to speak openly about things that are often left unsaid.Mallun shares candid reflections on identity, grief, mental health, and menopause — and the power of talking about experiences that many people carry quietly. Her perspective is grounded and thoughtful, offering a reminder that connection often starts with honesty.We also explore her work with Operator Collective, a venture fund built around community, bringing together experienced operators to support founders based on real-world experiences with people who have been there, done that, and are currently doing it.This is a conversation about perspective, courage, and rethinking where value comes from — and a reminder that not fitting the mould might be the very thing that allows you to build something meaningful.Episode HighlightsWhy being an outsider can become a powerful advantageThe freedom that comes from not knowing “the rules”How feedback can shape better decisions and relationshipsRethinking what it means to be “political” at workThe role of community in building companies and careersWhy sharing personal stories creates connectionThe reality of grief, mental health, and high performanceOpening up conversations around menopause and women’s healthBuilding a different kind of venture capital modelWhat it means to live a bountiful lifeChapters: 00:00 – Thinking differently by not knowing the rules03:00 – Growing up as an outsider and trying to fit in10:00 – Observation, pattern recognition, and advantage15:00 – Learning relationship building and feedback20:00 – Sharing stories, grief, and mental health25:00 – Menopause, identity, and workplace realities30:00 – Career journey from law to founder to VC35:00 – Building Operator Collective40:00 – Feedback, naysayers, and decision-making44:00 – What it means to live a bountiful lifeGuest Bio: Mallun Yen is the Founder and CEO of Operator Collective, a venture capital fund and community designed to bring experienced operators into startup investing. The fund manages over $150 million and brings together operators from leading technology companies including Salesforce, Stripe, and Slack.With more than two decades of experience across law, technology, and venture, Mallun has built and scaled organisations from startups to Fortune 100 companies. She previously served as Vice President of Worldwide Intellectual Property at Cisco, where she led global strategy and played a key role in major acquisitions.https://www.linkedin.com/in/mallun/About Bountifull:Bountifull is a podcast where we explore what it means to live a bountiful life in a world that often feels fast, noisy, and complicated. Through thoughtful conversations with interesting people from diverse backgrounds, we explore the ideas and experiences that shape how we live, and how we can have more joy in our lives, every day.