My First Million

Jason Calacanis, an entrepreneur and angel investor known for his early backing of Robinhood, shares his unique journey from journalist to investor. He dives into his gambling experiences and what they reveal about investment strategies. The conversation touches on the demise of tech media, the booming potential of paid communities, and his predictions for the rise of income share agreements and travel startups. With fresh insights on the evolving landscape of entrepreneurship, Jason's thoughts provoke excitement for the future of investment.

Immad Akhund, founder of Mercury and a savvy angel investor, dives into exciting discussions about the chaotic world of r/WallStreetBets and his memorable $100k bet. He shares innovative startup ideas targeting the creator economy and the need for better CRM tools. The conversation also covers the challenges in fintech and how Mercury is revolutionizing banking for startups. Tune in for insights into social media's influence on investment strategies and the future of platforms like Substack.

Jack Smith, an entrepreneur and founder of companies like Bungle and Ship, dives into fascinating topics. He discusses how WallStreetBets is reshaping Wall Street and the dynamics of retail investing. The conversation shifts to Taboola's billion-dollar success story and the challenges of the ad tech industry. Smith also unpacks Grayscale's influence in the Bitcoin market and speculates on the future of digital identities, touching on the implications of anonymity in online spaces. Finally, they explore how VC firms are venturing into media.

In this engaging conversation, Aaron Barrera, a cryptocurrency expert and trend analyst, delves into the ever-evolving world of digital finance. They explore the fascinating rise of pickleball and the business opportunities it creates, alongside the burgeoning market for romantic fiction catalyzed by Wattpad's sale. Sam shares his ingenious hack of Amazon's book rankings, while the duo tackles the allure of conspiracy theories like QAnon, discussing the financial dynamics of Bitcoin and market trends in niche sports and online entrepreneurship.

Suleman "Suli" Ali, a successful entrepreneur and investor, shares groundbreaking ideas during the chat. He discusses an innovative reputation database that could transform how individuals monetize their data. Suli envisions a new religion that prioritizes life and rational thought, moving away from traditional beliefs. He also highlights the benefits of shared ownership among friends for luxury assets and explores the potential of unique fintech solutions like creating a 'Stripe for vices'. His insights on navigating modern finance are both thought-provoking and entertaining.

Reed Duchscher, the manager of YouTube sensation MrBeast and founder of Night Media, dives into the dynamic world of digital talent management. He reveals how MrBeast's innovative strategies propelled him to fame, and discusses the emerging trend of faceless creators. Reed also explores the potential for student athletes in content creation, the rise of personal media companies, and the exciting opportunities in the gaming and sleep app markets. His insights into influencer marketing and the future of digital entrepreneurship are both enlightening and entertaining!

Delve into the fascinating world of DTC smelling salts designed for fitness buffs! Discover a mysterious anonymized app that fosters private communication, and be inspired by the groundbreaking journey of mRNA pioneer Katalin Kariko. The hosts dive into the dilemmas of sharing personal opinions and the merits of mentorship versus entrepreneurial ambition. A unique community challenge highlights the creative idea of giving away a business. Finally, they dissect the complexities of affiliate marketing and share quirky anecdotes about gimmicky business strategies.

Jeremy Cai, Founder and CEO of Italic, shares insights into his innovative e-commerce ventures, emphasizing accessible luxury through direct partnerships with manufacturers. He discusses the booming market for influencer-driven products and the vast opportunities in subscription boxes, including a playful idea for a bread subscription. The conversation also highlights the growing importance of cold chain logistics in food distribution and explores niche software solutions for homeschooling, showcasing the potential for unique business models in a changing economy.

A clever home security idea kicks off a lively discussion about innovative gadgets. The hosts delve into Wynter.io, a game-changer in user feedback for copywriting. Insights from Zuckerberg and Instagram's founder unveil the drama of tech negotiations. Amid playful banter, they explore digital meet and greets as a way to monetize fan interactions. Finally, an inspiring look at a little-known entrepreneur reveals the secrets behind a $30 million empire, sparking curiosity about his strategies.

A light-hearted awards ceremony highlights the best and worst of the business world in 2020, from the transformative influence of billionaires to standout companies like Zoom and Shopify. Predictions for 2021 spark lively debates, while discussions on innovative investment strategies and the changing landscape of e-commerce provide food for thought. The hosts also share personal reflections on fitness journeys, favorite books, and surprising quarantine joys, weaving a mix of humor and insight throughout the conversation.