Gokul Rajaram has worked as a leader at some of the most iconic companies in the world: Google, Facebook, Square, Pinterest, Coinbase and Doordash. In conversation with Caesar, Gokul dives into the motivations behind his journey from being one of the foremost ad experts in the world to being a leading tech investor and advisor.

Gokul promotes the superpower of learning how to be helpful. After sitting on more than a dozen executive boards over his career, Gokul advises listeners not to be motivated by status, but instead to focus on lending your expertise to growing businesses.

Instead of focusing on profits and promotions, he explains how over the years he has made the mission of the company – including serving consumers or small businesses – his North Star. In the abstract space of fintech, he stresses the importance of feeling excited about the product you are building for customers. He also underscores the need to work with high-caliber professionals who challenge you, because when you’re the dumbest person in the room, that’s when you learn.

In his professional leaps and bounds, Gokul has focused on regret minimization. Rather than staying in his lane as the product director of ads at Facebook, he sought out new and unique leadership roles in product development. He invites listeners before a career jump to consider the worst case scenario, and no matter the outcome, whether you will develop new skills and grow your network.

When it comes to investing, Gokul argues money making should not be front of mind. Instead, as an angel investor, he embraces the opportunity to support growing businesses and to learn. Investing is a way to stay relevant and engage in developing technologies more tangibly.

Gokul provides a motivating story of putting purpose over profits, and shares how he’s helping give back to the community now that his mindset is paying dividends.

Brandon Bouier, founder of the Data Investing Community and early Arta member, sits down with Caesar to share insights from the pivotal moments that defined his remarkable career journey. From leaving a stable government job during the 2009 recession to transitioning into the tech world, Brandon’s path is a testament to the power of embracing the unknown and living without regrets.

Brandon recounts his bold decision to move from Las Vegas to Seattle for a new opportunity, despite his family’s concerns. Unwilling to live with the nagging question of “what if,” he took a leap of faith that would expose him to the world of technology and ignite his desire to pivot from government work to the private sector.

The conversation delves into Brandon’s initial struggles with imposter syndrome and how encouragement from colleagues at the White House’s U.S. Digital Service finally gave him the confidence to make the leap into tech. He also shares invaluable lessons he’d impart to his younger self about taking responsibility for one’s life path, staying patient and focused on goals, and maintaining financial discipline.

Brandon credits his ability to take calculated risks, combined with the support of his wife’s direct approach to discussing finances as a team, as key factors in his success. His story serves as an inspiration for being thoughtful about risks while remaining unafraid to defy conventions in pursuit of one’s dreams.

In this week’s episode, Caesar hosts Diya Jolly, Chief Product Officer at Xero.

Early in the conversation, Diya shares her wisdom on the importance of following one's internal compass, emphasizing that true direction comes from within rather than succumbing to external pressures. She points out several times in her career when her family and loved ones encouraged her to do something different than what she wanted to do. Despite it all, Diya stayed her course based on her instincts and created a path that fueled her interests and further developed her skills.

Combining logic and creativity, Diya followed her gut and entered the engineering world because she wanted to build things. Sticking to her passion, Diya secured roles at leading tech giants, notably Google. Diya candidly recounts her initial hesitation to join Google, a decision she nearly passed on. However, she embraced the opportunity, resulting in a remarkable tenure exceeding seven years, during which she ascended to multiple leadership roles.

Diya also opens up about the impactful role that money plays in our lives and careers, sharing relatable stories from her own experiences.

This episode highlights the importance of embracing the journey towards greater ambitions rather than solely fixating on the destination ahead.