Ep. 4: From Harvard & Yale Law to a $40k calling with Lewis Bollard

Ep. 5: Inner frameworks for outer success, with Pauline Brown

Our guest today is Pauline Brown. She’s spent her career at the intersection of business, brand, and human judgment - starting at Bain, and going on to leadership roles at Estée Lauder, Avon, The Carlyle Group, and later as Chair of LVMH North America. Today, she focuses on something most people overlook: the part of judgment that goes beyond data - taste, meaning, and emotional resonance - through her work on her company, Aesthetic Intelligence. She also teaches these principles at Harvard and Columbia. In this conversation, we talk about the gap between success and significance, and why prestige alone eventually stops feeling like enough. Pauline shares how she chose alignment over optics, leaned into work that felt natural to her, and made career decisions that weren’t always obvious - but were right. We also get into why human judgment still matters, especially in an AI-driven world - and why qualities like taste, self-awareness, and emotional understanding will matter more, not less, going forward. This is a conversation about reinvention, identity, and having the courage to define success on your own terms. If you want to go deeper into Pauline’s thinking, she writes on Substack under Aesthetic Intelligence: https://substack.com/@paulinegarrisbrown?r=wxhof&utm_medium=ios&utm_source=profile&[…]EFLL-fxlTXXcnog6VX9VaCYFJDnvnFZOYDM_aem_6daQduul7yvO5kqxp5yz0Q You can also find more details about her upcoming Global Fellowship Retreat here: https://aestheticintelligence.com/ — Samana is a term for people in ancient times who stepped away from the mainstream to pursue an ideal higher than themselves. On this podcast, we get to know modern-day samanas: ambitious professionals who carved a unique path, not because they failed, but because they were brave enough to ask better questions.Brought to you by Vijay Wealth. Production and marketing by AQ Productions. —

Ep. 4: From Harvard & Yale Law to a $40k calling with Lewis Bollard

Our guest today is Lewis Bollard. He’s spent his career at the intersection of power and purpose - moving from Harvard to Bain, to Yale Law, and ultimately into his current role as Managing Director at Open Philanthropy, where he deploys capital to solve a largely overlooked global issue: factory farming. The real story goes beyond his resume - it revolves around the internal tension he learned to navigate between security and meaning, and between fear and conviction. Lewis grew up wrestling with big questions earlier than most. As a teenager, he confronted purpose head-on, a process he describes as painful but clarifying. That clarity eventually led him away from conventional prestige tracks - even when every social script told him to stay. He took a 4x pay cut after Yale Law to pursue work that aligned with his values, resisted the gravitational pull of “keeping all doors open,” and built a life around contribution rather than comparison. In this episode, we talk less about the polished highlights and more about what it costs to build a life that actually feels like yours. Lewis reflects on the fear that shapes high achievers, the illusion that more money always equals more security, and how identity can become entangled with status if you’re not paying attention. He shares stories of donors learning to let go, the psychology of “enough,” and why so many successful people struggle to close doors - even when the open ones are making them miserable. This conversation goes beyond career ladders - it’s about the inflection points where you decide what matters, what doesn’t, and what you’re willing to trade to build a life that's yours. — Samana is a term for people in ancient times who stepped away from the mainstream to pursue an ideal higher than themselves. On this podcast, we get to know modern-day samanas: ambitious professionals who carved a unique path, not because they failed, but because they were brave enough to ask better questions. Brought to you by Vijay Wealth. Production and marketing by AQ Productions.

Ep. 3: From Bain to the box office with Dick Boyce

Our guest today is Dick Boyce. He began at Bain & Company, rose to Partner, moved into operating leadership at PepsiCo, became CEO of J.Crew, and ultimately founded and led TPG’s Operating Group - the team that drove performance across a 100+ company portfolio at the top private equity firm. He later chaired brands like Burger King and Del Monte Foods, serves on the Board of Allbirds, and recently crossed into Hollywood as a producer. In this live episode, we talked about the experienced that shaped Dick through his career, how he earned credibility and trust from bright leaders around him, and what mindsets took him to the top 1% of investing, operating, and advisory roles. — Samana is a term for people in ancient times who stepped away from the mainstream to pursue an ideal higher than themselves. On this podcast, we get to know modern-day samanas: ambitious professionals who carved a unique path, not because they failed, but because they were brave enough to ask better questions. Brought to you by Vijay Wealth. Production and marketing by AQ Productions. -- (01:00) Introduction: Meet Dick Boyce (From Bain → Pepsi → J.Crew → TPG) (03:08) Lessons from Bain: Mentorship, Culture, Integrity (09:26) Becoming Partner in 5 Years at Bain (13:12) From Consulting to CEO: The J.Crew Turnaround Story (15:50) Leadership & Culture: Fixing Broken Companies (20:40) Career Superpower: Strategic Networking (24:15) Building the Operating Group at TPG (26:23) Managing Up & Influencing Leaders (29:48) Reinventing Yourself: From Business to Hollywood (34:43) Audience Q&A: Career Moves, Investing, Advice (1:00:00) Legacy, Purpose & Final Advice

Ep. 2: From simple beginnings to leading Tennis Australia with Cedric Cornelis

Our guest today is Cedric Cornelis, a global leader whose career has carried him from Europe to Asia, Australia, and the US - not by chasing comfort, but by following curiosity. An engineer by training with an MBA from Kellogg, Cedric began in consulting at Bain & Company before taking on senior strategy and operating roles at DHL and across a wide set of industries. Today, he serves as Chief Commercial Officer at Tennis Australia, where his commercial instincts meet a lifelong love of sport. But this isn’t a list of titles. It’s a story about the choices behind the moves. Cedric talks about how an engineer’s mindset shaped his approach to strategy, what reinvention really demands when you change industries, and how aligning personal passions with professional bets can create a career that compounds in meaning as well as scope. This isn’t about collecting stamps in a passport or climbing a corporate ladder for its own sake. It’s about how curiosity, when taken seriously, can turn reinvention into identity - on and off the court. - Samana is a term for people in ancient times who stepped away from the mainstream to pursue an ideal higher than themselves. On this podcast, we get to know modern-day samanas: ambitious professionals who carved a unique path, not because they failed, but because they were brave enough to ask better questions. Brought to you by Vijay Wealth. Production and marketing by AQ Productions. - (01:42) Introduction (03:08) Early Years & Education (04:03) Bain & Moving into Operations (07:58) Career Decision Framework (09:29) Family, Timing, & Global Moves (11:29) Lessons from Bain (13:43) Long-Term Value of Staying (15:51) Continuous Learning (17:57) Imposter Syndrome & Confidence (21:33) Leading Through Crisis (28:03) Joining Tennis Australia (33:47) Redefining Success (39:10) The Organic Path to C-suite (42:52) Advice for Young Professionals (44:22) Quickfire Round (47:29) Closing Remarks

Ep. 1: Growing StubHub, and knowing when to leave with Chris Tsakalakis

Our guest today is Chris Tsakalakis. He's led some of the internet’s most recognizable platforms as CEO: StubHub, Vivino, and Kiva, after his stint in consulting at Bain. But his path to the top wasn’t a straight line, and it wasn’t always smooth. The son of Greek immigrants, he spent his early years working for his father, learning the rhythms of labor before the language of business. He made his way through an Ivy League school, into Bain, and eventually into the upper ranks of eBay. Along the way, he learned how to lead through growth, through crisis, and through reinvention. In this episode, we talk less about the milestones and more about what it took to get through them. Chris reflects on how his relationship with ambition changed over time, why identity can so easily get tied to a job title, and how personal setbacks - including major surgery and moments of professional doubt - reshaped how he thinks about success. This isn’t a story about the rise of a CEO. It’s about what happens before the title comes and after it goes away. — Samana is a term for people in ancient times who stepped away from the mainstream to pursue an ideal higher than themselves. On this podcast, we get to know modern-day samanas: ambitious professionals who carved a unique path, not because they failed, but because they were brave enough to ask better questions. Brought to you by Vijay Wealth. Production and marketing by AQ Productions. — (00:00) Opening (00:22) Introduction to Samana (01:14) Early Career and Identity at Bain (05:10) Feedback, Insecurity, and Performance (08:52) Imposter Syndrome and Growth (13:00) Leadership and Vulnerability (15:23) Redefining Success Beyond Titles (22:49) Money, Parenting, and Values (27:30) Separating Identity from Career (31:39) Career Pivots and Following Curiosity (37:40) Lessons from Vivino and Moving On (40:39) Operating Principles and Daily Structure (44:25) Investment Wins and Losses (49:33) Legacy, Priorities, and Perspective (51:13) Closing Reflections