My First Million

Brian Halligan, Co-founder and former CEO of HubSpot, shares his entrepreneurial journey and insights on scaling companies. He discusses the emotional rollercoaster of building a startup, including the reality of imposter syndrome. Halligan explains HubSpot's unique 'pothole report' process to learn from mistakes and emphasizes the importance of maintaining a risk-seeking culture as companies grow. He predicts that while AI might seem like a bubble now, strong players will emerge, making it an exciting time for new entrepreneurs.

Chris Camillo, an observational investor and founder of Ticker Tags, shares his incredible journey of turning $20K into $60M through social-arbitrage investing. He dives into the concept of observational investing, highlighting how he identifies market opportunities using social data rather than traditional charts. From garage sale hustles to leveraging Google Trends for big bets, he reveals unique strategies like predicting demand shifts based on TikTok comments. Chris emphasizes the importance of expanding the investor class to bridge the wealth gap.

In this lively discussion, Steph Smith, a product and trends writer known for her data-driven insights, joins hosts Sam Parr and Shaan Puri to celebrate the 2025 Milly Awards. They dive into captivating topics such as the best and worst investments of the year, including Steph's brave decision to take Accutane for her confidence. The trio also share hilarious personal mishaps and memorable moments, from gorilla trekking to life-changing encounters with inspiring figures like Jesse Itzler and Will Guidara, rounding off with intriguing takes on parenting and social habits.

Ryan Deiss, a marketing entrepreneur and founder of DigitalMarketer, shares his insights on creating efficient business systems. He discusses the paradox of founder value potentially harming company value and emphasizes transitioning from operator to owner. Ryan outlines essential steps for business process mapping and highlights the importance of hiring functional leaders over just replicating oneself. He also touches on the psychological aspects of money and the significance of attracting top talent for sustainable growth.

Join John Morgan, a trailblazing trial lawyer and entrepreneur behind Morgan & Morgan, as he dives into his fascinating ventures. He reveals the magic of WonderWorks, his unique upside-down attraction, and shares the gritty origins of Alcatraz East, a profitable crime museum. Morgan discusses branding inspirations from Disney, his innovative legal tech platform Litify, and strategies for repurposing dying malls into vibrant community hubs. Plus, his wisdom on testing business ideas reminds us all to 'shoot bullets before cannonballs.'

Explore the transformative power of systems over feelings to achieve your goals. Discover the impact of reminders and accountability in personal change. Dive into Shaan's experience as a high school basketball coach, focusing on repetition and clarity to enhance player performance. Learn to craft memorable slogans that stick and the importance of honest feedback from peers. Lastly, reflect on the evolution of work and the significance of video in today's content-driven world.

Jesse Cole, the creative force behind the Savannah Bananas, discusses his journey transforming a struggling baseball team into a billion-dollar entertainment phenomenon. He shares his unique idea-generation habits, inspired by showbiz legends like Disney and Barnum. Learn how Jesse navigated through financial hardships, embraced outrageous promotions, and prioritized fan engagement. He reveals his influences from viral creator MrBeast and emphasizes building a culture of creativity in his organization, all while pursuing the exhilarating challenge of delivering a memorable experience.

Discover how simple businesses like gutter cleaning can thrive with clever marketing strategies. Uncover the unique success story behind Billy Bob's Teeth and the art of creating novelty brands. Learn about a roofer's viral tactics, transforming local trades into engaging content. Get insights into the lucrative live events sector and how storytelling boosts niche markets. Plus, explore the impact of noise on cognition and innovative product ideas like specialty noise-canceling earbuds. Perfect for aspiring entrepreneurs seeking inspiration!

In this engaging chat, Ben Horowitz, co-founder of Andreessen Horowitz, shares insights from his diverse journey—from reshaping the Tupac murder case to writing leadership principles. He critiques why most management books fail, emphasizing the need for emotionally intelligent decision-making. Ben also provides strategies for confronting difficult team members and building CEO confidence. Plus, he discusses the exciting potential of AI in startups and the importance of creating a vibrant company culture through actionable rules.

Sheel Mohnot, dubbed the 'most interesting man in tech', is an investor and entrepreneur with a knack for innovative ideas. In this chat, he dives into intriguing business concepts like AI tools for landscaping and an eHarmony-style platform for surrogacy, addressing market inefficiencies. He also discusses the booming peptide industry and a potential EMS fitness venture. Sheel shares his belief in the potential of prediction marketplaces and argues that podcasts can often replace reading books for valuable insights.