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The Tim Ferriss Show
#635: Jason Calacanis on Brooklyn Grit, Big Asks, Angel Investing (Uber, Calm, Robinhood, and more), The Magic of Thinking Big, and St*bbing People in the Face but Never in the Back
Nov 18, 2022
02:14:42
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Quick takeaways
- Building successful brands and businesses requires timing, faster content, and leveraging the power of being first.
- Failure can be a catalyst for rebounding quickly and demonstrating adaptability and entrepreneurial skills.
- Networking and staying informed about emerging trends are crucial for creating successful partnerships.
- Success should be measured by impactful memories and cherished connections, rather than wealth and financial achievements.
Deep dives
Building a Business Empire: From Silicon Alley Reporter to Web Logs Inc.
Jason Calacanis shares the journey of his entrepreneurial success, starting with the creation of Silicon Alley Reporter and its eventual sale for $30 million to Dow Jones. After facing setbacks and being laid off, Calacanis embarked on a new venture, building a network of web logs (blogs) focused on various industries. With the right timing and the development of faster, better, and cheaper content, AOL acquired Web Logs Inc. for $30 million. This experience solidified Calacanis' belief in his ability to build successful brands and businesses.
The Significance of Blogs and Faster, Better, Cheaper Content
In the early 2000s, Calacanis recognized the potential in blogs, as they offered faster and more engaging content compared to traditional media. He assembled a team of writers and bloggers who covered a range of topics, generating revenue through ads. Calacanis understood the value of being first in a medium and leveraged this knowledge to build a successful network. Through the creation of Web Logs Inc., he became a pioneer in the blogging industry, foreshadowing the significance and impact of online content in the years to come.
Overcoming Setbacks and Harnessing Determination
After experiencing failure with Silicon Alley Reporter and losing his job at Dow Jones, Calacanis harnessed his rage and determination to prove himself again. He recognized that his success wasn't a fluke and that he had the power to build brands and businesses from scratch. With the creation of Web Logs Inc., he rebounded quickly, demonstrating his ability to adapt and seize opportunities. This experience cemented his confidence in his entrepreneurial skills and his ability to navigate the ever-changing business landscape.
The Value of Networking and seizing opportunities
Throughout his journey, Calacanis emphasized the importance of networking, connecting with others in the industry, and staying informed about emerging trends. By reaching out to individuals and engaging in conversations about new projects and ideas, he gained insights into the landscape and discovered the potential of web logs. This networking facilitated the creation of successful partnerships and collaborations, proving instrumental in his journey towards building thriving businesses.
The success of the podcast
The all-in podcast has gained popularity by capturing lightning in a bottle. The chemistry between the hosts, Jason, Chamath, Freeburg, and Sachs, creates a unique dynamic that resonates with the audience. The show's format, which includes lively debates, informative discussions, and humor, keeps listeners engaged and entertained. Jason, as the moderator, plays a crucial role in orchestrating the conversations, highlighting each host's strengths, and ensuring a cohesive flow. The authenticity and candidness of the conversations make it feel like friends having a discussion, allowing listeners to feel connected to the show. The success of all-in can also be attributed to its timing, providing a refreshing alternative to the increasingly narrow Overton window in public discourse.
Jason's view on success
Jason's perspective on success has evolved over time. He recognizes the significance of capturing memorable moments and creating lasting memories with friends and loved ones. As he reflects on the passing of friends like Dave Goldberg and Tony Hsieh, Jason is reminded of the importance of cherishing meaningful experiences. Jason aims to accumulate impactful memories and make the most of his remaining years. Success for him is measured by the memories he creates and the connections he fosters, understanding that these are the true treasures of life.
Discovering New Potential
The podcast episode delves into the idea that trying new endeavors can uncover hidden talents and potential. The speaker shares their experience of transitioning from podcasting to moderating and compares it to playing different sports. They explain how past experiences and preparation in one field can serve as a foundation for success in a different one. This realization has opened up new possibilities and perspectives for the speaker, emphasizing the importance of exploring different paths and being open to new opportunities.
Finding Real Value Beyond Money
The podcast episode touches on the realization that wealth and financial success do not necessarily equate to happiness. The speaker reflects on their personal journey of achieving financial success and the subsequent discovery that money alone does not bring fulfillment. They share how experiences with wealthy friends revealed that beyond a certain point, the scorecard of cash becomes insignificant. The speaker highlights the importance of finding purpose, passion, and joy in one's life as the true indicators of success. They emphasize that the ability to pursue what brings genuine enthusiasm and excitement is the ultimate measure of a fulfilling life.
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Jason Calacanis (@jason) has invested in more than 300 startups in the past decade (Uber, Calm, Robinhood, and more), was Sequoia Capital's first Scout, and is the author of the book ANGEL. He also hosts two podcasts, This Week in Startups and All-In.
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[05:39] Why is this only the first time Jason’s been on the show?
[06:37] Never underestimate the power of checklists.
[08:56] How Jason’s young life was steeped in blood and taxes.
[11:57] How Jason entered the world of entrepreneurship.
[29:32] What happened when Jason got fired from his own company.
[34:05] Orchestrating a comeback the very next day.
[37:49] The Mercury Club that never was.
[41:37] The origin of “Calacanis.”
[43:01] Building a blogging empire.
[48:36] Finding blog writers.
[52:51] Planning events and making memories.
[58:39] Friendship, loyalty, and collaboration with close friends.
[1:06:00] All-In: When a solo act gets tricked into joining a band.
[1:13:39] Memorable times All-In has gone off the rails.
[1:21:49] With greatly followed podcasts comes great responsibility.
[1:27:38] KeepingAll-In running smoothly with four very different personalities.
[1:34:53] Talent-wrangling techniques.
[1:39:30] Bill Maher’s moderation style.
[1:40:47] Friendly rapport can be contagious.
[1:42:26] Can you see your comfort zone from the Overton window?
[1:45:44] Transfering skills, building popularity, and co-existing with jet blockers.
[1:52:16] What happens when you catch the car?
[1:55:15] Psychedelic therapy and a big win in Colorado.
[2:01:28] Jason’s billboard and parting thoughts.
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For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast.
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Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more.
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