00:00 Paki McCormick is the founder of the successful newsletter and media empire, Not Boring, which has quickly gained popularity and is now the number one substack newsletter on business.

08:47 Paki McCormick's family is originally from County Cork, and he grew up in the Lehigh Valley area of Pennsylvania, where he showed early signs of his future as a writer and entrepreneur by creating his own newspapers and books as a child.

16:17 Paki McCormick had a boring internship on Wall Street where he wasn't allowed to trade and had to ask dumb questions, but he still excelled and was offered a position at Bank of America, which eventually led him to work on municipal bonds.

23:45 Packy McCormick had a challenging but rewarding experience working at Breather, where he had to convince landlords to rent spaces to the company and even cleaned the spaces himself, eventually growing his team to 25 people and becoming VP of Experience.

31:00 Packy McCormick and his team at Breather were able to turn the company around and go from negative 25% margins to positive 25% margins by implementing a new strategy that involved adding monthly spaces and competing with companies like WeWork and No Tell.

38:12 Packy McCormick started building the Not Boring Club by creating a Slack group and using his newsletter to attract early applicants, but the launch was put on pause due to the COVID-19 pandemic.

45:31 Packy McCormick decided to pivot his startup idea into a newsletter called Not Boring, which started gaining traction and subscribers, leading him to delay implementing a subscription model in order to focus on growth.

52:56 Packy McCormick decided to pivot his startup idea into a newsletter called Not Boring, which started gaining traction and subscribers, leading him to delay implementing a subscription model in order to focus on growth and eventually explore advertising sponsorships.

01:00:16 Packy McCormick started writing sponsored posts on his newsletter, Not Boring, as a way to generate revenue, but he made sure to maintain high standards and only write about companies he believed in, which ended up being well-received by his audience, including founders and entrepreneurs.

01:07:54 Packy McCormick aims to be an optimistic voice in tech journalism, providing thoughtful analysis and converting skeptics to at least consider the industry's advancements.

01:15:19 Packy McCormick aims to write the best thing ever on a particular company in his sponsored deep dives, even if it's a two-year-old company, and he believes that as long as the company is happy with the analysis, the open rate is not as important.

01:23:20 Packy McCormick started writing about Web3 and crypto as a turning point in his content, initially apologetic but eventually realizing the value and potential of the technology, leading to more frequent articles on the topic.

01:30:50 Packy McCormick aims to approach his writing on Web3 and crypto by highlighting the value and potential of the technology, tying it back to familiar business concepts, and acknowledging both the positive and negative aspects of decentralized autonomous organizations (DAOs).

01:38:17 Packy McCormick acknowledges that he is not a good planner and doesn't have a long-term plan for his writing on Web3 and crypto, but he recognizes the need to establish some structure around his work in order to focus on other opportunities; he also discusses the potential for building a decentralized autonomous organization (DAO) or a loose structure to tap into the Not Boring audience and network.

01:45:44 Packy McCormick discusses the trade-offs he makes in his investment approach, acknowledging that he may not conduct as much diligence as traditional investors but focuses on identifying what can go right in a company; he also emphasizes the importance of maximizing winners in venture capital and the value of portfolio construction.

01:53:56 The trade-offs of running a one-person corporation like Not Boring include the risk of losing momentum if the person doesn't show up to write, limited ability to build other businesses around the brand, and the potential dilution of the core offering if too many other products or services are promoted.

02:01:41 The host discusses the challenges of scaling the business and building an organization around the core product, highlighting the difficulty of hiring and managing a team while maintaining the unique content and voice of the brand.

02:09:09 The biggest risk to the business in the short term is that people are becoming tired of the optimism and are feeling that things are tough right now, but the recent growth and success of the podcast has been driven by various factors such as writing a piece on Discord, appearing on CNBC, and partnering with Andreessen Horowitz to help explain what is happening in the industry and why it can be a positive thing.

02:16:40 The content of the podcast has attracted a valuable audience of founders and company leaders, and the alignment with the venture business is the key to its success.

02:24:31 The speaker discusses the concept of "process power" and how it relates to the creation of a product, highlighting the difficulty in articulating the process by which a product comes to fruition.

02:32:41 The speaker discusses the possibility of turning Not Boring into a platform for launching a billion-dollar fund, but acknowledges that it would require a different strategy and competing with established firms.

02:40:36 The hosts discuss their current book recommendations, including "Rabbits" and "The Expanse," and express their excitement for the release of the final book in "The Expanse" series.