My First Million

Andrew Wilkinson, entrepreneur and co-founder of Tiny, shares his entrepreneurial journey and the challenges of transitioning from active entrepreneur to investor. He discusses the evolution of Pixel Union and its surprising success in e-commerce. Wilkinson reveals the hardest and easiest businesses to start, providing insights for aspiring entrepreneurs. He also touches on the unique position of AeroPress in the coffee market and candidly addresses deceptive practices in the investment sector, giving listeners a behind-the-scenes look at the realities of business and investment.

The podcast dives into the shocking collapse of FTX, unraveling the chaos that ensued after Sam Bankman-Fried's downfall. They discuss the massive loss of trust in the cryptocurrency market, highlighting the fraud allegations that led to FTX's bankruptcy. Insights from social media reactions reveal shifting public perceptions. The hosts explore leadership failures and the troubling connections within FTX, while drawing parallels to past financial scandals that have shaken investor confidence.

Sahil Bloom, an entrepreneur and former private equity investor, shares his journey into content creation and insights on building multiple businesses. He talks about the shift from finance to a creative career, emphasizing passion over traditional paths. Bloom presents three money-making business ideas, including mobile podcast studios and innovative newsletter strategies. The conversation also touches on the dynamics of social media, personal branding, and the amusing challenges of content creation, all while maintaining a humorous take on professionalism and personal aesthetics.

Kaitlyn Michelle Siragusa, known as Amouranth, is a social media entertainer and OnlyFans creator who has built a $40 million business empire. She shares her journey from running a character party business to becoming a digital star. Amouranth discusses her strategies for online growth and collaboration, emphasizing the importance of brand-building and community. The conversation touches on managing content on adult platforms and the mental health challenges creators face. She even reveals her bold investment in a Chinese ball pit manufacturer!

Dive into hilarious negotiations over a domain name as entrepreneurs blend comedy with business. Discover the quirks of non-techies in the tech sector, tackling trends like AI and crypto. Unpack the importance of grit and learn why patience often beats instant gratification, illustrated through a famous marshmallow experiment. It's a rollercoaster of laughs and insights that showcases the fun side of entrepreneurship.

Kevin Rose, an entrepreneur and VC known for founding Digg and Hodinkee, dives into his $100M/year watch blog and his fascination with crypto. He shares intriguing stories about early tech figures like Zuckerberg, emphasizes the need for focus in entrepreneurship, and explores the emotional aspects of creativity. The conversation also covers investment strategies in the unpredictable startup landscape, alongside insights into AI's impact on creative industries and the ethical considerations of longevity research using pets.

Discover the hilarious tale of two pranksters impersonating Twitter employees to fool the media, showcasing the absurdity of modern news. Dive into the booming business of Halloween, from consumer spending to quirky side hustles that cash in on the festivities. Explore the mysterious tech company Humane and its potential to reshape mobile interaction. The conversation wraps up with inspiring stories of successful entrepreneurs redefining work and fulfillment, blending humor with insights on navigating the holiday market.

Dive into the fascinating world of luck and risk! Discover the four types of luck and how being prepared can turn chance encounters into golden opportunities. Uncover how building your reputation can attract success, just like early adopters who recognized game-changing trends. Plus, learn about the different levels of risk entrepreneurs navigate, from market uncertainties to execution pitfalls. This insightful conversation will inspire you to embrace risks while enhancing your fortune!

The hosts dive into the drama of a hostile takeover involving Sara's List, sparking discussions about strategic investments and tech industry implications. They celebrate the meteoric rise of the GAS app, revealing how it raked in a million dollars in just ten days. Humor ensues with a ransom note twist, while they also tackle the chaotic world of couple collaboration in business. With insights on startup success and the changing dynamics of job boards, this episode blends entrepreneurial tips with engaging anecdotes.

Palmer Luckey, the billionaire founder of Oculus and Anduril, shares his journey from flipping iPhones on eBay to selling Oculus for $2 billion. He dives into his innovative ideas for revamping the prison system with a nonprofit model aimed at rehabilitation. Luckey also discusses his bold ventures into synthetic foods and the challenges of competing in the defense industry. With a take on national security and controversy in the Ukraine-Russia conflict, he proves that creativity knows no bounds. Plus, find out why he still chooses to fly coach!