In this conversation with Justin Welsh, we go beyond the usual “how-to” tactics and explore his struggles with imposter syndrome, money anxiety, and the deep-seated drive to prove himself stemming from childhood experiences. Justin’s story illustrates the complexities of transitioning from a high-pressure corporate role to building a thriving online business, highlighting both the challenges … Read More
I recently talked with Cate Hall on my podcast. Cate is a former Supreme Court advocate turned professional poker player who has since co-founded startups and explored various creative pursuits. Her journey of embracing agency resonated deeply with my own experiences of leaving the default path. Cate shared insights from her popular article on agency, … Read More
In this episode with Matt Bateman, I dive into a fascinating conversation about the intersections of work, education, and personal development. Matt, an early childhood educator, philosopher, and the founder of Guidepost Montessori, shares his unique perspective on growing up without the traditional work scripts and how it influenced his approach to education and life. … Read More
In this episode with David Pakman, I delve into the complexities and challenges of the political commentary space, exploring not just the professional hurdles but also the deeply personal aspects of such a career. David shares his unique story, from his family’s immigration from Argentina to his early engagement with technology and the internet, which … Read More
In this episode with Justin Jackson, co-founder of Transistor, we dive into his fascinating journey from early internet ventures to establishing a calm business model that prioritizes life’s margins. Justin shares his experiences growing up in a family where entrepreneurial spirit was a necessity, the lessons learned from running a snowboard shop, and how these … Read More
In this episode with Joe Hudson, I delve into his riveting life story, exploring his journey from a challenging childhood dominated by a sense of conflict and anger, to his eventual awakening and self-discovery. Joe’s experiences living in various countries, coupled with his personal transformation, offer invaluable insights into dealing with adversity, embracing emotional fluidity, … Read More
In this conversation with Erin, we explored the transformative power of inner wisdom and the courage it takes to step off the beaten path. Erin shared her experiences of living abroad and the deep personal shifts that followed, highlighting the importance of listening to one’s inner voice and the profound realizations that can arise from … Read More
In this episode of the “Pathless Path” podcast, I had the pleasure of sitting down with my good friend Jovian Gautama. Jovian’s story is a fascinating one, tracing his roots back to Indonesia and detailing his evolution from selling steel in Taiwan to becoming the CEO of Castro (a role he’s since moved on from). … Read More
I had the pleasure of welcoming back Steph Smith for her second appearance, this time on the renamed “The Pathless Path Podcast.” We dove into a wide array of topics, ranging from the success of creators like Mr. Beast to the balance of side gigs and full-time work. We reflect on the scale and opportunities … Read More
Dan Vassallo walked away from a $500k a year salary at Amazon to become self-employed. He didn’t do this to make more money and he didn’t do this to trade the identity of a successful worker for the identity of a successful founder. He did it because he couldn’t quiet the feeling that there was … Read More