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The speaker shares his personal journey of becoming obsessed with reading and entrepreneurship. He highlights the importance of studying the history of successful entrepreneurs and how it can provide valuable insights and ideas for future generations. He mentions his admiration for figures like David Ogilvy, Sam Walton, and Charlie Munger, and emphasizes the significance of learning from their experiences. By immersing himself in the stories and ideas of these entrepreneurs, he has gained valuable knowledge that he now shares through his podcast.
The speaker discusses his experience as a solo podcaster, explaining how he single-handedly creates, edits, and produces each episode. He recognizes the benefits of being an independent creator, allowing him to have full control over the content and style of his podcast. He mentions the improvements he continually makes to his show, listening back to episodes and constantly striving to enhance the quality and tighten the delivery of each episode. Although he acknowledges that there is always room for improvement, he takes pride in the high standard of his work and continues to provide valuable and engaging content to his listeners.
The speaker acknowledges the influence of other successful podcasters on his own career, mentioning Dan Carlin from Hardcore History and Bill Burr from The Monday Morning Podcast. He admires their ability to captivate audiences through their engaging monologues, and he has drawn inspiration from their storytelling styles. He explains his commitment to always striving for improvement, constantly reevaluating and refining his own content. Additionally, the speaker expresses his appreciation for the support and connections he has received within the podcasting community, and the valuable role they have played in his journey as a podcaster.
Advertising heavily during recessions can be a strategic move, as it helps to differentiate yourself and maintain visibility in a crowded market. By investing in advertising when others pull back, you can gain an edge and capture the attention of potential customers.
In the rapidly evolving venture capital space, differentiation is crucial. By finding unique ways to differentiate themselves, venture firms can stand out from the competition and attract valuable deal flow. Examples include providing exceptional value through podcasts, building strong relationships with entrepreneurs, and seeking out partnerships that drive mutual success.
Investors can gain a competitive advantage by immersing themselves in the study of history and constantly learning. By leveraging their knowledge and understanding of past business trends, successful investors can make informed decisions based on patterns and insights from the market. Sharing this knowledge and building a strong network can also lead to exciting investment opportunities.
Podcasts have the unique ability to connect with audiences through authentic storytelling. By being genuine and true to oneself, podcasts can create a strong bond with listeners. The power of storytelling allows for entertaining and informative content that can make a lasting impact on the audience.
To reach a wider audience and fulfill the potential of their product, podcasts should prioritize marketing and branding efforts. Building a strong brand and effectively promoting the podcast can ensure that more people are aware of its existence and can benefit from the content shared.
Consistency and persistence over time are key factors in the success of a podcast. By offering valuable content and remaining dedicated, a podcast can attract an audience and create a loyal following. It takes time to build a brand and fully realize the potential impact of a podcast.
The podcast emphasizes the importance of pursuing what you are intensely interested in, regardless of whether there is a clear career path for it. The speaker encourages the students to follow their passion, even if it doesn't align with traditional job roles.
The podcast highlights the significance of reading and continuous learning. The speaker advises the students to cultivate a reading habit, emphasizing that their friends may be engrossed in apps but developing strong reading skills is crucial for intellectual growth.
The podcast touches on the limitations of formal education and emphasizes the value of real-world experience. The speaker shares personal anecdotes about their own entrepreneurial journey, encouraging the students to prioritize hands-on learning and practical experiences over relying solely on traditional education.
David Rosenthal and Ben Gilbert — of the Acquired podcast — invited me to San Francisco for a discussion on our mutual obsession: spending every waking hour studying the history of entrepreneurship and sharing those lessons on our podcasts.
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This episode is brought to you by: Tiny: Tiny is the easiest way to sell your business. Tiny provides quick and straightforward exits for Founders. Get in touch with Tiny by emailing hi@tiny.com.
[3:00] David’s time with Charlie Munger
[5:30] Henry Flagler after Standard Oil
[8:30] What makes a great biography, and how to capture all sides of complex characters?
[11:00] Studying history is a form of leverage to achieve success
[13:00] How do we figure out what the true story is for an episode we're doing?
[20:30] Silicon Valley should focus more on durability than growth
[21:30] How David got into reading biographies and podcasting
[25:40] What were each of their influences before starting Acquired and Founders?
[35:30] How to suck less over time
[37:30] What motivates, Ben, David, and David to get better?
[45:00] Dead ends: business model changes, paid podcasts, changing the name to “Adapting”, and Senra's “Autotelic”
[51:30] “You’re not advertising to a standing army, you’re advertising to a moving parade”
[56:00] Comparison of podcasting business models
[1:00:10] Senra’s insane Readwise "healthy twitter" habit
[1:04:30] Is it possible for the ultra-wealthy not to mess up their kids?
[1:14:30] The fleeting moments you get to spend with your kids
[1:17:00] The value of building relationships with best-in-class peers
[1:19:30] How the book publishing industry works
[1:28:45] How to differentiate yourself as an investor in 2023?
[1:38:30] The greatest historical examples as content marketing
[2:02:00] The best businesses are cults (and Senra starts one on the episode)
[2:07:00] Senra gives feedback to Ben and David on Acquired episode format
[2:15:30] Steve Jobs’ 1997 product matrix
[2:17:00] The moral imperative to market products that help people
[2:23:00] Ray Kroc and Steve Jobs: deeply flawed founders
[2:23:30] The founders we idolize are world-builders
[2:28:00] When yachts and jets are underpriced assets
[2:32:00] How to compete when money is cheap vs. when there are real interest rates
[2:39:30] When Ben and David have fixed broken episodes in post-production
[2:44:30] Why masters of craft are so interesting to study
[2:45:30] Should you listen to advice?
[2:51:00] David’s first job detailing cars
[2:52:30] The Cuban experience immigrating to Miami
[3:01:00] College entrepreneurship programs
[3:04:00] Ben’s experience learning UNIX as a kid
[3:08:30] David remembers Tim Ferriss guest lecturing in college
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