🔑 Key Takeaways
- Not Boring, McCormick's one-person media and investment empire, is redefining the media business model with its unique personal touch and has already gained significant success with its number one substack newsletter on business.
- Pilot's software ensures financial accuracy and consistency while providing customers with easy access to personal assistance. Additionally, the show is not investment advice and listeners can visit pilot.com/acquired for more information and a 20% discount.
- Being honest and owning mistakes, along with a strong work ethic instilled by parents, can lead to success in a variety of fields, even during tough times. Embracing one's "nerdy" qualities can also be a source of confidence.
- Despite facing challenges in finding the right career path, it's important to keep an open mind and take advantage of new opportunities that arise. Building a strong foundation in investment banking can lead to success in other areas, such as entrepreneurship or private equity.
- Formative experiences and hardship can lead to success if you're patient, willing to get your hands dirty and apply the power of compounding.
- Starting-level jobs provide essential skills and connections needed for career growth. Learning on the job, dealing with ambiguity, and building networks can aid in future career opportunities.
- Understanding your team, market demand, and strategy is crucial for success. Overexpansion without proper demand can lead to failure. Focus on marginally adding space and a shared vision to drive positive results.
- Success in business requires a well-planned strategy, buy-in from everyone, and an understanding of the market. Starting small, taking a sabbatical, and recognizing that leaders are fallible can all lead to long-term success.
- Building a community around a hobby or interest requires effort, but the benefits are worth it. Don't give up, even in challenging times. Focus on building connections and having fun, and success will follow.
- Being true to yourself and avoiding portraying a persona can lead to better interactions, content creation, and scalability. Balancing optimism with practicality and staying true to yourself is a long-term strategy for success in personal branding.
- Having a positive attitude, a supportive network, creativity, patience, persistence, and a strategic approach are essential to building a successful venture. Don't be afraid to take risks and focus on audience growth before revenue.
- Building a successful subscription model requires a hyper-specific approach, careful consideration of content, and a dedicated business strategy. Advertising can also be a valuable revenue source, but understanding the audience and creating a compelling pitch is crucial.
- Starting a successful newsletter involves embracing multiple revenue sources, creating engaging content, and being persistent.
- Sponsored content can be successful and valuable if done with transparency and quality. Writers can use it to reach their audience and companies can benefit from a targeted audience.
- Disclosing any motivations in journalism can be helpful for readers to make informed decisions. Alternative media models like Not Boring show that journalistic integrity can exist outside traditional media, and utilizing platforms like Substack and Twitter can provide a sustainable alternative to advertising.
- When writing about tech companies, it is crucial to remain realistic and provide thoughtful analysis. Investigative journalism plays a vital role in uncovering the truth behind companies, and tying back to business principles can help convert skeptics into appreciators.
- Companies can ensure high-quality sponsored posts by putting effort into providing transparent information and maintaining the writer's integrity, resulting in valuable and interesting content for the audience.
- Maintaining journalistic integrity and empathy for others' struggles are key ingredients for startup success. Quality content and genuine sponsorship deals are more effective than short-term, unrealistic goals.
- Consistency, hard work, and never giving up are essential for achieving success. Compound growth happens over time, so stay focused on your goals and keep pushing forward.
- Crypto offers new tools for businesses and consumers, but business fundamentals still matter. Removing middlemen can create value, but a non-dismissive, business-focused approach is key. Analyze crypto with familiar concepts to evaluate potential impact.
- Despite the challenges faced in leadership and decision-making, DAOs have the potential for emergent properties. Progressive decentralization can be a good approach. Dismissing DAOs outright could lead to missed opportunities. In a few decades, solo corporations run by one person could reach a trillion-dollar market cap.
- Aspiring creators can turn their passion into a long-term business by prioritizing their content, leveraging Web 3.0 platforms, and transitioning from being in front of the camera to owning the production through smart investments.
- Transparency and a focus on the positive potential of a company are key to success in this new model of venture investing. Investment memos and public writing can aid deal sourcing.
- Prioritize the well-being of all companies, not just the winners, through thoughtful portfolio construction. Access top investment opportunities with less effort and collaborate with other investors for a more emergent approach to venture capital.
- Digital platforms like PitchBook, Substack, and AngelList have made it possible for solo entrepreneurs to compete with larger firms, providing better-informed decisions and simplifying the investment process, thus democratizing the venture capital industry.
- Specialization of labor can lead to business growth through easy-to-use software and personalized services. However, lack of outside investment and diluting core products can impact momentum. Clear expectations and focus on content and add-ons aligned with it can boost value.
- Building a team and consistent brand identity are important in scaling a personal brand business. Continuous effort and innovation are required to avoid stagnation and reach a wider audience.
- Not Boring newsletter provides an approachable and relatable glimpse into the near future by being a late early adopter and translating new developments in a tech-optimistic tone.
- The partnership between a16z and Packy McCormick aims to bring complex crypto developments closer to people and elevate the industry's growth through the Not Boring flywheel—content, audience, and investing mutually reinforcing each other.
- The success of a business investment depends on investor-founder alignment and having the right people in the audience, not just audience size. Public company shareholders consider long-term growth over short-term gains.
- Not Boring's success is dependent on building a network of readers, embracing individual writing styles, and utilizing process power to consistently generate great ideas. The lack of a community creates room for growth and counter-positioning against traditional media companies.
- While joining a venture firm may seem like a logical progression, it is important to consider the impact it may have on your independent voice and future opportunities. Think carefully about the potential trade-offs and consider the time dimension before making a decision.
- Building a billion-dollar VC fund involves a unique strategy and a phenomenal team, but not getting too greedy and maintaining control is crucial for success. Super angels can become firms and compete with established players.
- Invest in dedicated baby blankets with velcro and zippers for swaddling and consider reading "Rabbit" for a thrilling sci-fi adventure, "The Expanse" for an excellent series, or "Red Rising" for a recommended trilogy.
- Recommendations for book series and collaboration strategies in the world of science fiction, along with a nod to the successes of others in the space. Plus, the guest Packy's website, podcast, and Twitter account are worth checking out.
📝 Podcast Summary
Not Boring: McCormick's Personal Flair Reinventing Media
Not Boring, a one-person media and investment empire run by Packy McCormick, has achieved explosive growth and is reinventing the media business model while utilizing a distinct personal flair. Despite being only a year and a half old, Not Boring is the number one substack newsletter on business and would likely also be number one in the technology category if McCormick decided to switch. In addition to his success, McCormick is a part of a liquid super team at Acquired. Piloting is the backbone of the modern financial stack for startups and is the sponsor for season nine of Acquired.
Pilot offers innovative software for financial convenience, with the option of personal interaction.
Pilot uses software to ensure an accurate and consistent experience when it comes to financial observations, insights and concerns. Customers can access this easily and engage with a person when required. Not Boring founder Packy McCormick enjoyed writing funny yet informative compositions from a young age, showing an early version of his future career in writing. The show is not investment advice and the hosts are conflicted with their investments in some of the entities discussed. Listeners can visit pilot.com/acquired for more information on how Pilot can help eliminate the pain of tax prep and bookkeeping, and receive a 20% discount on their first six months of service.
The Importance of Humor and Work Ethic in Parenting
A combination of humor with the backing of serious research works well. Not Boring is both informative and entertaining, done with diligence. Work ethic can come from parents like Packy, whose dad worked all the time as a consultant and who had a mom completing her Ph.D. and working while raising two kids. The way they parented included a valuable lesson that you should be honest if you are not going to do well. Owning mistakes is another important lesson. Packy was involved in a lot of different things in college, showing that being nerdy can also be cool. Even in tough times, like in 2009, you can succeed in investment banking.
Navigating Career Transitions in Investment Banking
Getting an investment banking job during the recession in 2009 was tough. Interning for a financial desk like Packy did at Bank of America's energy trading desk required hard work, but little actual trading experience. Packy's rotational program placement into public finance led him to work on municipal bonds, which he found a little boring. Despite being number one in his class, he knew that finance was not where he wanted to stay. Packy started a company called ThrowGo, hoping it would help him get into business school, but he got rejected by Stanford's GSB. Instead, he found a new opportunity with Breather. Additionally, top-quality investment bank analysts get their PE offers early.
Learning from early mistakes in investing and entrepreneurship.
Making mistakes early on and learning from them can help you become a better investor. It's difficult to buy and hold when you're in a position where cash is useful and a material amount of your net worth, but it's important to be patient and let compounding do its thing. Formative experiences, even if they seem silly or insignificant, can help with future career opportunities. It's important to get your hands dirty and deal with the gritty aspects of running a company if you want to be a successful entrepreneur. Chris Sacca's quote about hiring individuals who had a challenging upbringing is a reminder that adversity and struggle can ultimately lead to success.
Importance of Starting-level Jobs and Building Networks
Packy's experience of doing odd jobs and taking up a job at Breather helped him gain essential skills and experience required for his career growth. He learned to compete, design, and furnish spaces, convince landlords, and work with cleaning companies and Uber Rush messengers to clean Breather spaces. He even got on his knees and begged landlords for spaces. Apart from that, he also formed connections and networks that would later help him in his career. Packy's story shows the importance of taking up starting-level jobs, learning on the job, dealing with ambiguity and uncertainty, and building connections that can aid in future career growth.
The Secrets to Turning a Struggling Startup Around
Startups are not glamorous, and the hard work is a product of the system designed. It's essential to understand the people within your team and throughout the company. Overexpansion without proper demand can lead to disastrous results, as seen in the case of Breather. It took a serious memo, full of data science and ideas, to turn the company around and make it profitable. Understanding strategy is critical, and it's important to hire people who also grasp it. Positive results can come about by adding marginally to monthly space and competing with other companies. A successful company needs a collective buy-in with a shared vision.
Strategies for Success in Business
Having a well-planned strategy, getting people to buy into it, and offering something that makes sense and fits within the market are crucial for success. This was evident when we flipped spaces and went from -25% margins to +25% margins. Although it was difficult for some teams, everyone bought in, and it was a meaningful thing. Additionally, starting small by remixing ideas from respected individuals like Ben Thompson and writing about them can lead to bigger things, as seen in the case of starting Not Boring. Taking a sabbatical can also be valuable in providing clarity and giving the team a chance to see that the company can thrive without a particular individual. Lastly, realizing that everyone in leadership positions is also as human and fallible as oneself can be empowering.
Building a Passionate Community: Challenges and Rewards
Building a community around a particular passion or hobby is hard, but rewarding. Not having small groups bonded around shared interests after college can feel isolating. Starting a physical space for like-minded people to come together and connect is a great idea but building the community comes before signing a lease or raising money. The COVID outbreak has put a pause on events and social gatherings, but it's important to keep the end goal in mind and not give up. Starting something new can lead to unexpected opportunities and success, even if it doesn't look like it at first. It's important to be passionate and have fun with whatever you choose to pursue.
The Importance of Authenticity in Personal Branding
Remaining true to yourself and being authentic is important, especially when building a personal brand. While it may be tempting to play a character or persona to quickly gain followers, it can be exhausting and lead to a miserable experience. Being genuine and being yourself can make interactions and creating content easier, and more scalable for a one-person operation. Being optimistic can also be a helpful trait, but it's important to balance it with practicality and realism when pursuing ideas and ventures. While it's easy to make trade-offs to boost engagement and followers, focusing on being yourself is a long-term strategy that can lead to success.
Tips for Success in Entrepreneurship
It is important to have a positive outlook and not be afraid of taking risks, even if it means sacrificing some comfort. Having a supportive network, including family and friends, can help in making important decisions and pursuing entrepreneurship. Being creative and finding a unique approach can help differentiate oneself in a crowded market. Patience and persistence are key in building a successful venture, even if it means delaying revenue generation in favor of audience growth. Finally, it is important to be strategic in growth, leveraging tactics such as landing pages and Product Hunt launches to drive audience engagement.
The Challenges and Strategies of Implementing Subscriptions as a Business Model
Subscriptions can work as a business model if it is architected well, but it is a big challenge to convert more than 2-3% of your audience to paid offerings. Additionally, hyper-specificity and companies willing to pay for the content play a big role. It is crucial to build the entire business and content strategy around subscriptions. Advertising can be another source of revenue. Understanding the audience's characteristics is necessary to pitch to potential advertisers. An excellent deck is essential to get sponsors interested. The internet and Twitter can be a great way to market the deck. Packy decided not to go the subscription route due to challenges in figuring out what could be put behind a paywall without handicapping the main content.
The journey to profitable newsletter: insights from Packy's experience.
Starting a newsletter is not an easy task, especially when thinking about revenue sources. Packy was an optimist, and he believed that he could make good money through sponsorships as long as he had enough readers. Although he initially planned to rely solely on subscriptions, he eventually embraced advertising. He had an addictive personality and loved the growth. The journey to breakeven was short, and Packy blew past it, as he had looked forward to getting there for a long time. Creating content that people love to read and share is a rewarding experience, but it takes a lot of effort and dedication, as Packy's story shows.
Sponsored Content: A Valuable Tool for Writers and Companies
Packy McCormick's success with sponsored content challenges the notion that writers should not use newsletters to shill. By only writing about companies he is bullish on and would invest in himself, he has set a high bar for himself and is aware of the negative connotation surrounding sponsored content. Nevertheless, he has found success with his unique sponsorship format and has even gained behind-the-scenes access to fast-growing startups, which has been well-received by his audience. This shows that, with transparency and a focus on quality, sponsored content can be a valuable tool for both writers and companies looking to reach a targeted audience.
The importance of transparency in alternative media models.
Disclosure and transparency about sponsored content and investments build trust with readers and can provide valuable insights for startup founders. Alternative media models like Not Boring demonstrate that journalistic integrity can exist outside traditional media organizations, and that traditional tech journalism can be overly cynical and lacking in understanding of the challenges faced by small startups. Web 3.0 platforms like Substack and Twitter have enabled independent creators to operate with low costs, and subscription-based models can provide a more sustainable alternative to advertising. Incentives and motives are present in all journalism, but disclosing these openly can help readers make more informed decisions about the information they consume.
Balancing Optimism with Realism in Writing about the Tech Industry
Being optimistic about tech companies and the industry as a whole can attract an audience of like-minded individuals who are also optimistic. However, it is important to remain realistic and well-reasoned in writing about these companies and not waste people's time. Assuming the audience is smart is a primary principle in writing and it is crucial to provide thoughtful analysis. Investigative journalism plays a vital role in uncovering the truth behind companies that may not be what they seem. Overall, being thoughtful about the industry and tying back to business principles can help convert skeptics and pessimists into thoughtful individuals who appreciate the advancements made in the past few decades.
The Importance of Effort and Transparency in Sponsored Deep Dives
The success of a sponsored deep dive depends on the effort put in to make it great and the willingness of the company to be open and transparent about their operations. While Thursday pieces may not always be as interesting as Monday pieces, the goal should be to write the best thing ever written about that particular company. The key question to ask as a company is whether the sponsored deep dive is the best thing they can do to get a great deep analysis done about their company. Companies can choose how interesting they want the piece to be by being open and transparent with their information. The success of the sponsored post ultimately depends on maintaining the writer's integrity and providing high-quality content that is valuable to the audience.
The Importance of Journalistic Integrity and Empathy in Startup Success
Journalistic integrity is important for a strong democracy and must be maintained by being fully disclosed and incentivized. Independent journalism has its place but must be applied correctly, and startup or company failures should not be held to the same standard as Watergate. Compounding success takes time and effort, and it's important to have empathy for others' struggles and failures. Not Boring's success was due to its founder's years of experience working for a startup and failure. While aiming to make a million dollars from the newsletter may seem crazy, Not Boring's success was driven by quality content and sponsorship deals like the piece on Excel that got picked up by prominent media outlets.
The Power of Compound Growth: A Success Story
Consistency, hard work, and compound growth are the keys to success. Packy's business is an excellent example of how persistence pays off. Despite starting with zero revenue, he successfully built his business, and now he is making around $20,000 per month after a year only. This is the result of his hard work and never giving up. He doubles down despite the challenges and continues to write sponsored posts, which in turn attract more followers and, consequently, more money. As his success shows, compound growth happens, and the numbers keep getting bigger as the time goes on. So, it's worth staying focused and working on your goals if you want to achieve success.
Leveraging Crypto for Business and Consumers
Crypto, or Web 3.0, offers a new set of tools that can be used in business and can have a positive impact on consumers and creators. Taking a step back and removing the middleman can create more value for both parties. However, it is important to approach it from a non-dismissive and business-focused perspective. While DAOs may offer a new way of organizing, business fundamentals and structure are still necessary in order to achieve goals and ship products. Crypto is not a panacea, but rather a new toolkit that can be used in certain situations. When analyzing crypto, it is important to tie it back to familiar business concepts and evaluate it based on its potential impact for both businesses and consumers.
Potential of DAOs and Challenges Ahead
DAOs have the potential for emergent properties that would not have been possible in a traditional corporation. However, there are still leadership and decision-making issues that need to be resolved. Progressive decentralization can be a good approach where control is given up to users and owners over time. It's important not to dismiss DAOs outright despite the challenges. In business, it's important to get the audience you deserve and not alienate those who have a sense of the fundamentals. The author predicts that within a decade or two, there will be solo corporations run by just one person that could reach a trillion-dollar market cap. Not Boring has achieved its revenue goal and Packy has become a prominent figure in the creator economy.
Building a Lasting Creator Empire
Creators have the potential to build a solo corporation and create something big that outlives them. For instance, Not Boring can be turned into something more than a newsletter that could create lasting products and opportunities. However, this requires a long-term plan and structure. Aspiring creators should prioritize their content and focus firmly on what they like doing, rather than constantly looking ahead without any planning involved. They can leverage Web 3.0 platforms to build networks, collaborate with others, and create something more significant than a few million-dollar companies. Creators can also transition from being in front of the camera to owning the production by investing in startups and shaping their trajectories.
A Hands-On Approach to Scalable Venture Fundraising
Running a venture fund scales better than traditional methods of fundraising, but it requires a hands-on approach. Writing investment memos isn't necessary for all investments, but it helps to show up prepared. Writing about different industries and companies is helpful in sourcing deals. By publishing his thoughts publicly, he is transparent about his investment strategy. He doesn't lead a single round or write any term sheets. He focuses on what can go really right with a company rather than finding its flaws. Running a venture fund this way is a new approach and it remains to be seen whether it will work. Overall, transparency is key to success in this model of venture investing.
The Not Boring Approach to Venture Capital and the Emergent Way of Investing
In venture capital, the focus should be on maximizing the winners, not avoiding mistakes. Not Boring's innovative approach involves portfolio construction that prioritizes the wellbeing of all companies, not just the winners. Although diversification is important, founders should focus on ensuring their employees get the best outcome possible. The Not Boring strategy has enabled access to top investment opportunities with less effort than traditional venture investors. PitchBook is a useful resource for anyone seeking information on funds, their histories and fund size. The emergent approach to venture capital involves sharing deals, advice and thoughts among a group of investors, rather than one specific way of thinking.
Digital Platforms Revolutionizing Venture Capital Industry
The use of digital platforms like PitchBook, Substack, and AngelList has revolutionized the venture capital industry, enabling firms to operate with minimal staff and reorganize their value chain. With tools like these, it is possible for solo entrepreneurs like Packy to compete with larger firms by leveraging software and off-the-shelf solutions to streamline their operations. The massive amounts of data available through platforms like PitchBook allow investors to make better-informed decisions, while the ease of communication and organization provided by AngelList make fund management much more manageable. The author argues that the use of these tools has democratized the venture capital industry, giving more power to individuals and simplifying the investment process.
The Benefits and Challenges of Specialization in AngelList Model
The AngelList model exemplifies how specialization of labor can lead to the growth of businesses. It offers access to software that is easy to use, with a personal touch of integration. There are also experts who provide advice and services. The downside of a one-person corporation is the lack of outside investors, which makes it difficult to take time off and maintain momentum. Building other businesses on the side can dilute the core product and cause confusion among the audience. Expectations should be clear with the focus mainly on content and other add-ons that align with it. The sponsorship model works well, but building a personal product can have higher equity value. Specialization of labor can lead to a super liquid way of stitching all those together.
Challenges of Scaling a Personal Brand Business
Unlike other businesses, where founders need to pull themselves out of the core product and build an organization to scale, in the case of being the product, the founder will always be in the first phase. Scaling out in a predictable way can be challenging. Hiring the right people who can do what the founder does and building a brand voice and format may help build an organization on top. Growing the audience and scale can happen linearly or exponentially, depending on the founder's energy and effort. Being lazy about the content side can result in hitting the saturation point of the S-curve more quickly. Continuously feeding off each other, a bigger portfolio of companies, and a larger audience can lead to a million-person newsletter in the next five years.
Bridging the Gap Between the Present and Near Future
Not Boring newsletter aims to provide a glimpse into the near future that's explained in an approachable and not crazy-sounding way. The author, Packy, strives to bridge the gap between the three to six months possible future that he lives in and the one-month probable future that people generally inhabit. He achieves this by being a late early adopter, someone who can say when to take a look at a new development. As technology and the future keep evolving, Packy believes that if he can continue to translate what's going on and make people feel comfortable with it, his newsletter will continue to grow irrespective of market conditions. He believes in being tech optimistic and writing in a voice that the audience can relate to.
Explaining Crypto Developments and Supporting Growth through Partnership.
The partnership between a16z and Packy McCormick aims to explain complex crypto developments and their potential benefits to people. They work together to tell the stories of companies in their portfolio and why investing in them can be a good thing. The team at a16z is passionate about supporting and elevating the growth of the crypto industry by providing necessary resources and expertise. The Not Boring flywheel, which centers around content, audience, and investing, works well together in attracting valuable audience members who are more likely to start or run companies. The mutual reinforcement between content, audience, and investing is the powerful aspect of the flywheel.
Importance of Alignment in Business Investments
The success of a business investment does not solely depend on the type of company or industry it belongs to but rather if the investor and the founder are aligned with each other, and if the founder is already a reader of Not Boring. The audience size is not as important as having the right types of people in the audience, which makes introductions warm and appreciated, rather than transactional. On the sponsorship side, there is more of an equation there, and people are willing to pay more with a bigger audience. Public company shareholders are long-term oriented and account for the future trajectory of the business rather than the next quarter.
Not Boring's Success and Future Prospects
Not Boring's future value is dependent on network economies and counter-positioning compared to traditional media companies. While there may not be Facebook-level network effects, the more people in the target audience that read Not Boring, the more powerful it becomes. The lack of a community to organize these effects may be seen as an opportunity for Not Boring in the future. Process power plays a significant role in Not Boring's success, as it's difficult to articulate the consistent way lightning strikes to create great ideas. Finally, while The Economist has a strict brand guideline, Not Boring embraces the beauty of writing style that reflects the individual author rather than a brand voice.
Joining a Venture Firm: Limitations & Trade-Offs
Joining a venture firm may limit the upside and options for Packy McCormick because he will lose his independent voice, and everything he writes will go through legal and compliance teams. It may make sense for him to take this step when he is deeply in the S-curve, and people assume that he knows what he is talking about. However, the fund may not get what it paid for because Packy will lose half his value as soon as he set foot in the door. Delaying the upside for 5-7+ years and cutting down something that is at an inflection point right now may not be the best idea. The decision should consider the time dimension and the trade-offs because sometimes the ultimate value may be higher.
Strategies for Building a Billion-Dollar VC Fund
Building a billion-dollar venture capital fund from Not Boring Capital is possible but requires a different strategy as deploying a billion dollars in follow checks is not feasible. It would require a phenomenal team and going head-to-head with established firms. However, staying greedy can lead to lowering the bar on who to write sponsored posts or who the advertisers are and mess up the current success of Not Boring. It's important to maintain control and not get too greedy. Being a super angel can turn into a firm and competition with established firms is doable, as seen in the examples of Andreessen and Josh and [...].
Tips for Swaddling Babies and Book Recommendations
New parents should not attempt to swaddle their babies in a regular blanket as it can be quite challenging and cause heartache. It's better to get dedicated baby blankets with velcro and zippers, and bring them to the hospital. A review of technical merits and possibilities of Web3.0, with a focus on engineering analysis, has been published by Pioneer Square Labs. The book "Rabbit" is a thrilling sci-fi read that combines the styles of Haruki Murakami and Ready Player One. The Expanse series of books are an excellent read, with the final ninth book coming out soon. The first two are amazing, the third is good, and the subsequent books are still really good. Red Rising trilogy is also recommended for reading.
Book recommendations, podcast strategy, and science fiction success.
The hosts of the podcast recommend reading books one through three of Red Rising because they were good, but advise against reading book four because it is considered an abomination. They also discuss the strategy of making podcast episodes free to listeners after a limited period, which was inspired by Packy's Not Boring newsletter. Additionally, they talk about the success of The Expanse, a science fiction series written by two authors who collaborated and were George R.R. Martin's assistants. Finally, they thank Packy for being a guest on the show and recommend listeners to check out his website, podcast, and Twitter account.