Not Boring (with Packy McCormick)

In this engaging episode of "Acquired," hosts Ben Gilbert and David Rosenthal are joined by Paki McCormick, creator of the "Not Boring" newsletter and investment empire. McCormick shares his journey from working in finance to founding "Not Boring," which rapidly became the top Substack newsletter on business and experienced explosive growth in just a year and a half. McCormick discusses the challenges and triumphs of running a solo operation, the integration of "Not Boring Capital," and his experience with venture capital. The episode delves into the strategies behind "Not Boring," the impact of platforms like Substack and Twitter, and the potential future of solo corporations. With a transparent approach to sponsored content and a commitment to quality, McCormick's story is a testament to the power of aligning content, audience, and investment in the modern creator economy.

• David Rosenthal and Ben Gilbert introduce themselves and their roles.
• Ben Gilbert provides an overview of the podcast's theme and his professional background as co-founder and managing director of Pioneer Square Labs and PSL Ventures.
• David Rosenthal shares his background as an angel investor and mentions his return from paternity leave.
• Ben Gilbert and David Rosenthal express their excitement about covering 'Not Boring' by Paki McCormick.

"Welcome to season nine, episode six of Acquired, the podcast about great technology companies and the stories and playbooks behind them. I'm Ben Gilbert, and I am the co-founder and managing director of Seattle based Pioneer Square Labs and our venture fund, PSL Ventures."

The quote introduces the podcast and Ben Gilbert's role and background, setting the stage for the episode's theme and discussion.

"And I'm David Rosenthal, and I am an angel investor based in San Francisco. And I am back sort of from paternity leave."

David Rosenthal introduces himself and mentions his recent paternity leave, providing personal context for the episode.

• 'Not Boring' is a successful newsletter turned media and investment empire.
• Paki McCormick has achieved significant growth in a short time, becoming a top newsletter on Substack.
• The discussion highlights Paki's unique approach to media and investing, blending informative content with a whimsical writing style.

"Not boring is the number one Substack newsletter on business. If Paki decided to switch to the technology category, from everything I can tell, he would be number one there, too."

This quote emphasizes the success and popularity of 'Not Boring,' showcasing Paki McCormick's achievements in the newsletter space.

• The hosts announce the opening of the Acquired LP show back catalog to the public.
• They discuss the benefits for paid LP community members and encourage listeners to subscribe to the new public podcast feed.
• The announcement includes information on exclusive content and upcoming episodes.

"For the 98% of you out there who have not joined the acquired LP community, we are opening up every single episode of the LP show back catalog to you today."

The quote informs listeners about the availability of previously exclusive content, expanding the podcast's reach and offering more value to the audience.

• Pilot is a trusted partner for accounting, tax, and bookkeeping needs for startups and growth companies.
• The hosts discuss Pilot's growth and the importance of focusing on core business aspects while outsourcing other tasks like accounting.
• They highlight Pilot's services, experience, and the offer of a discount to Acquired listeners.

"Pilot both sets up and operates your company's entire financial stack. So finance, accounting, tax, even CFO services like investor reporting from your general ledger all the way up to budgeting and financial sections of board decks, Pilot takes care of all that."

The quote describes the comprehensive services provided by Pilot, explaining how they can benefit startups by handling financial operations.

• The hosts provide a disclaimer that the show is not investment advice and disclose their investments in Not Boring entities.
• They emphasize the informational and entertainment purposes of the show.

"This show is for informational and entertainment purposes only. And I promise you it will be both of those."

The quote serves as a disclaimer, clarifying the intent of the podcast and setting expectations for the content discussed.

• Paki discusses his childhood interests, including creating books and newspapers, hinting at his future in writing and media.
• He shares stories about his work ethic, influenced by his parents and upbringing.
• Paki's experience at Breather is discussed, highlighting his operational roles and strategic thinking.
• The conversation touches on his educational background, early career in finance, and the transition to entrepreneurship.

"I used to make these little books or newspapers on post it notes."

This quote illustrates Paki's early interest in writing and creating content, which is relevant to his later success with 'Not Boring.'

"I had all these pairs, and they would take me in the women's locker room at the pool or something like that. And I was like a five-year-old kid, and I would come home and draw stick figures of boobs."

Paki shares a humorous anecdote from his childhood, showing his early creative tendencies and hinting at his future whimsical writing style.

"That is certainly from both of my parents. My dad, as I said, was a consultant at Arthur Anderson and would literally fly to Germany for a day and come home or fly down to Miami to go to Miami Herald and then make it home by 04:00 that night to take us to the fair and then fly back out the next morning."

Paki attributes his strong work ethic to his parents, providing insight into his drive and dedication in his professional life.

• The discussion begins with the recounting of the early days of COVID-19, with the cancellation of events and the initial belief that normalcy would return in two weeks.
• The speakers express a common sentiment from that period, an optimistic expectation that the disruption would be short-lived.

"Remember that? We're all going to be back in two weeks, right?" "We're all going to be back in two weeks. As soon as this blows over, we'll be back."

• These quotes reflect the early optimism and the underestimation of the COVID-19 pandemic's impact, which was a widespread attitude at the time.

• Paki McCormick discusses the growth of his Twitter following and newsletter, highlighting the strategy of welcoming new subscribers and tracking progression.
• David Rosenthal and Ben Gilbert share their experiences of feeling uncredentialed before starting their ventures and the surprising shift in public perception once they became successful.

"One of the things that I wanted to do very early on, I would say, welcome to the new X subscribers. Now there are y of us here." "It's so funny you had that impression of us because I had zero credibility before starting acquired."

• The first quote illustrates Paki's approach to fostering a sense of community and tracking growth in his newsletter, which was not initially intended as a growth hack but became an effective one.
• The second quote shows Ben's empathy towards Paki's feelings of being an outsider and the relatable experience of gaining unexpected recognition.

• Paki emphasizes the importance of maintaining his personal authenticity online, despite the growth in followers and potential scrutiny from trolls or regulatory bodies.
• Ben Gilbert discusses the trade-offs people make in growing a personal brand online and the challenge of remaining true to oneself.

"I'm really trying to just be the same person that I've been the whole time." "I think a lot of people make a lot of trade-offs to do that, where they play a part on the Internet and play a character rather than being themselves."

• Paki's quote demonstrates his commitment to staying true to his original persona, even as his online presence grows.
• Ben's quote highlights the common issue of online personas diverging from one's true self in pursuit of rapid growth, which Paki has managed to avoid.

• Paki recounts his personal situation during March 2020, including being unemployed, married, and expecting a child, while working on a start-up idea.
• He discusses the role of optimism in his life and the emotional challenges of pursuing entrepreneurial ventures, particularly during the uncertain times of the pandemic.

"Never once was there a time when I was like, my life is absolutely over." "This is incredibly embarrassing."

• Paki's first quote shows his unwavering optimism even in the face of unemployment and other life challenges.
• The second quote reveals Paki's vulnerability and the emotional toll of low attendance at an event he organized, despite his prestigious educational background and experience.

• Paki shares the evolution of his newsletter, 'Not Boring,' and the strategic decision to combine business strategy with pop culture in his writing.
• He discusses the challenges of maintaining a unique voice and the decision to avoid a subscription model to prioritize growth.

"What if I just start writing this newsletter? And what if I start writing essays and it needs to be different than Ben Thompson?" "I realized really early on that I just needed to kind of be as close to myself as humanly possible, or else it was just going to be too much work."

• The first quote reflects Paki's ambition to create a distinctive newsletter that stands out from existing ones like Ben Thompson's 'Stratechery.'
• The second quote underlines Paki's realization that authenticity is not only true to his character but also a practical approach to maintaining his writing and online interactions.

• Paki details his approach to monetizing his newsletter through sponsorships instead of subscriptions, driven by his preference for growth and reach over immediate revenue.
• He explains how he filled his sponsorship slots for the remainder of 2020 by sharing his advertising deck on Twitter, which led to a significant increase in his income expectations.

"I think a huge difference between someone like a Lenny and someone like me is that Lenny's audience is so specific and you know exactly who you are and who should be paying for that." "I was just addicted because I locked myself into this thing where I was telling people how many I grew every week."

• The first quote compares Paki's broad audience with Lenny's more targeted one, suggesting that a subscription model might not be as effective for 'Not Boring.'
• The second quote captures Paki's dedication to growth and his strategic decision to delay implementing subscriptions in favor of increasing his audience size.

• Paki discusses the ethical considerations and potential criticism of his sponsored content model, emphasizing the importance of transparency and quality.
• He contrasts his approach with traditional journalism's norms and asserts that sponsored content can be valuable if done with integrity.

"My goal is to write the best thing that's been written on that company every time I do a sponsored deep dive." "I am sponsored and this company is paying me right now to write about this."

• The first quote outlines Paki's commitment to producing high-quality sponsored content that provides genuine insights into the featured companies.
• The second quote demonstrates Paki's transparency about the financial relationship behind his sponsored content, ensuring readers are fully aware of his incentives.

• The speakers reflect on the broader implications of Paki's business model for the media industry and the shifting definitions of journalistic integrity in the digital age.
• They discuss the potential impact of independent content creators like Paki on traditional journalism and the importance of maintaining a high standard of analysis and disclosure.

"There's a lot to unpack. So first of all, the platforms of all in web three now certainly rely on web two platforms in a really big way." "I think everybody has incentives and motives, and at least if I'm saying I am sponsored and this company is paying me right now to write about this, it is just very out in the open what I'm trying to do."

• The first quote acknowledges the reliance of modern content platforms on the infrastructure provided by web two companies, which has enabled the rise of independent creators.
• The second quote reiterates Paki's philosophy of complete transparency regarding his incentives, contrasting it with the sometimes opaque motives in traditional journalism.

• David Rosenthal expresses understanding for the challenges faced by founders.
• He acknowledges that while he can relate to their experiences, the content must stand on its own merit.

"gives me a great empathy for what founders are doing, but the content has to stand for itself."

The quote shows David's ability to empathize with founders due to his own experiences, yet he emphasizes the importance of content quality and independence.

• Paki McCormick discusses the rapid growth of his newsletter, Not Boring, and his ambitious revenue target of $1 million for the year.
• He credits a combination of factors for his optimism, including successful sponsored posts, high engagement with his content, and a positive outlook influenced by his environment in Miami.

"Yeah, so I'd been thinking a little bit about not boring capital, and so that was there, but really was talking about just purely making a million dollars off of the newsletter."

Paki explains that while he had considered expanding into Not Boring Capital, his primary focus was on generating significant revenue through the newsletter itself.

• Paki reflects on the positive reaction he received from his audience after tweeting about his million-dollar goal.
• He suggests that people resonate with others taking risks and aiming for success, and that his audience didn't perceive his tweet as arrogant but rather as hopeful and ambitious.

"And then, as I think happens often with those tweets, the support was actually huge from them."

This quote captures the idea that audiences can be supportive of content creators who openly share their aspirations and challenges, fostering a sense of community and mutual encouragement.

• Paki distinguishes between personal income goals and business revenue targets, noting that a million dollars in revenue for a business is a reasonable milestone that could potentially attract investment in certain markets.

"And the other thing is, I guess there is like a tiny buffer between just like, me saying I'm going to make a million dollar salary this year and saying, not boring, will make a million dollars because it's still a business."

Paki's statement clarifies that his revenue goal is set within the context of business growth, not personal income, which carries different implications for the company's future and potential fundraising.

• Paki provides an update on Not Boring's financial progress, indicating that the newsletter is on track to cross a million dollars in revenue for the year.
• He acknowledges the business's informal financial management and the positive impact of compounding on revenue growth.

"I think chances are we're going to just kind of cross a million dollars in 2021."

This quote reveals Paki's confidence in reaching his ambitious revenue goal, reflecting the success of his content strategy and audience engagement.

• Paki discusses the rapid increase in his Twitter following, which has grown significantly faster than his newsletter subscriber count.
• He expresses a desire to balance his time between engaging on Twitter and growing his newsletter audience.

"There's a little bit of a bummer in those Twitter numbers, which is a point of pride for a while was that I had more subscribers than I had Twitter followers."

Paki acknowledges the challenge of maintaining a balance between different platforms and the importance of focusing on the core content that drives his business.

• Paki reflects on his transition to writing about Web3, noting that it was a turning point for Not Boring.
• He emphasizes the importance of providing a balanced perspective on Web3, avoiding extremes, and relating the concepts to familiar business ideas.

"So the web three was a turning point."

This quote captures Paki's recognition of Web3 as a significant area of interest and potential growth for his content, marking a strategic shift in focus for Not Boring.

• Paki addresses concerns from some audience members who preferred his earlier content focus and are skeptical of his increased coverage of Web3 topics.
• He discusses the importance of retaining an audience that values fundamentals while accepting that some may leave due to changing content themes.

"But if people are just like, hey, you're writing about web three and I think it's stupid, and they leave, then that's totally fine."

Paki's comment illustrates his acceptance of audience turnover as a natural part of evolving content focus and the pursuit of topics he finds most compelling.

• Paki discusses the concept of "solo corporations" and the potential for individuals to run trillion-dollar market cap organizations.
• He expresses uncertainty about Not Boring's long-term plans, highlighting the tension between focusing on content quality and exploring additional business opportunities.

"Like, would I love not boring to be a big and lasting thing that builds actual products and does things that kind of outlive me 100%?"

This quote reflects Paki's aspiration for Not Boring to have a lasting impact beyond his direct involvement, despite current uncertainties about how to achieve that goal.

• Paki explains how Not Boring Capital emerged from his newsletter activities and how it complements his content creation by allowing him to invest in the companies he writes about.
• He values the opportunity to engage with founders and contribute to their strategic discussions, leveraging his insights from writing about various industries.

"But it really came from one time where I wrote an essay to help a friend who was trying to explain how his company worked, and then he raised a syndicate with somebody else."

Paki describes the organic development of Not Boring Capital as an outgrowth of his desire to help founders articulate their business models and strategies through his writing.

• Paki discusses his venture capital strategy, which includes a high volume of investments and reliance on other investors' due diligence.
• He acknowledges the trade-offs of his approach, such as potentially missing red flags, but emphasizes his focus on what could go right with investments.

"I'm doing probably less diligence on a specific company than most people who are investing in a company will."

Paki's quote highlights the intentional choice to prioritize the potential upside of investments over exhaustive due diligence, aligning with his content-driven access to deal flow.

• David Rosenthal discusses the challenges of hiring, managing, and maintaining a team.
• The process requires a significant commitment and can be risky.
• Building a team necessitates a step back to establish the structure of an organization.

"It would require a big pause and a step back where I was like, all right, I can't do as much content for the next three months because I need to build out a team."

The quote highlights the need for a strategic pause in content creation to focus on team building, which is a difficult but necessary step for organizational growth.

• Ben Gilbert explores the concept of maintaining a brand voice through different team members.
• The example of Morning Brew demonstrates the success of this approach.
• Hiring the right people is crucial to maintain the consistency of content.

"There is a brand voice and a format here. And if we can hire correctly for people that can do the not boring thing, kind of like they did for the Morning Brew."

This quote emphasizes the importance of finding the right team members who can replicate the brand's voice and format, as exemplified by Morning Brew's success despite changes in the writing team.

• Paki McCormick reflects on the benefits of partnerships in content creation and organizational management.
• Partnerships can allow for a division of focus between content and building the organization.
• Paki contrasts his solo work environment with the partnership dynamic at Acquired.

"It is nice, I think, for them that they've had this partnership where I'm sitting in a room alone here."

Paki's quote illustrates the contrast between working alone versus having a partnership where responsibilities can be shared, highlighting the potential advantages of the latter.

• Paki mentions his support system, including his brother's editing help and his wife's assistance despite her own commitments.
• The support system plays a role in managing his workload and business considerations.
• Paki acknowledges the value of this support in his work.

"I have my brother who edits the vast majority of my pieces and helps me think through the business side. Pooja is a saint, and in addition to kind of working a full-time job and managing our growing boy, also knows when she's dead tired on Sunday, read drafts."

This quote recognizes the personal support system that contributes to Paki's ability to produce content and manage his business, showing appreciation for the help received from family.

• David Rosenthal questions the necessity of expanding content when the core offering is strong.
• He considers the scalability of content on the internet and its direct relation to capital.
• The discussion revolves around the potential ceiling of content-based growth.

"What is the ceiling to the core thing? Like, if the core thing is great and continues to be, do you need all the other stuff do you need more shows? Do you need more content?"

David's quote prompts consideration of the limits of content expansion and whether a strong core offering is sufficient for growth on the internet, especially when capital is also a factor.

• Paki McCormick discusses the scalability of his newsletter and its interconnected growth with his portfolio of companies.
• He contemplates the possibility of reaching a million subscribers and the impact of audience size on content and business.
• The growth trajectory of the newsletter is a key focus.

"I think it can scale with this one thing pretty well. And everything also kind of continues to feed off each other where if I have a bigger portfolio of companies, but each time I mention a company in a newsletter, it has a bigger impact because the audience has gotten bigger."

Paki's quote illustrates how audience growth can enhance the influence of his content and create a scaling effect with his business ventures, reflecting on the potential of reaching a larger subscriber base.

• Paki reflects on the growth rate of his audience and the potential saturation point.
• He acknowledges that growth may become linear rather than exponential over time.
• The content's evolution and its ability to attract new readers while retaining existing ones are crucial for continued growth.

"The chart where it still grows 1000 to 2000 people a week, the newsletter, but 1000 to 2000 people a week is a lot different when you're at 40,000 versus 80,000."

The quote highlights the changing impact of audience growth numbers as the subscriber base increases and the need for content to evolve to maintain growth momentum.

• Paki discusses the importance of content strategy in maintaining audience interest and relevance.
• He emphasizes the balance between being forward-looking and approachable in content creation.
• The challenge is to provide insights into the near future without losing touch with the audience's understanding.

"What I will hopefully continue to do well at is looking into the very near future never being the earliest person on something, but kind of being the person who can say, like, all right, this is actually probably worth taking a look at now."

Paki's quote captures his approach to content creation, focusing on timely and accessible insights into emerging trends and developments, aiming to keep the audience engaged and informed.

• Paki reflects on writing an optimistic newsletter during a bull run and the potential impact of a market downturn.
• He considers how persistent optimism in content could become tiring for the audience during tough economic times.
• The balance between maintaining hope and addressing reality is considered as a risk to his business model.

"If there's a two year bear market, we come out the other side and reload and continue to grow and things continue to get better and all of that. But those two years are going to be a really interesting time and not boring."

Paki's quote contemplates the challenge of sustaining an optimistic tone in his content amidst a potential bear market and the importance of adapting to maintain audience engagement during economic downturns.

• Paki McCormick discusses the compounding effects of success and the opportunities that arise from it.
• He mentions significant milestones, such as increasing Twitter followers and appearances on CNBC.
• The relationship between these achievements and the growing influence of his work is explored.

"Last month, speaking of compounding, like, all this somehow happened in one month."

The quote reflects on the rapid accumulation of successes and the surprising rate at which opportunities and recognition can compound, highlighting a period of significant growth for Paki.

• Paki recounts an incident involving Discord and his influence on the platform's decisions.
• He also discusses his advisory role at Andreessen Horowitz and the alignment of values and goals.
• The partnership aims to help companies tell their stories and navigate the complexities of the industry.

"Mario and I wrote this piece on Discord. And then Discord CEO, in the replies to my tweet about the piece, announced that they were adding web three integrations and then announced that they were not adding web three integrations."

The quote illustrates Paki's influence on significant industry players and his role in shaping narratives within the tech community, as well as his involvement in advising companies on strategic communication.

• Paki considers the trade-offs between maintaining independence and joining a venture capital firm.
• He values the freedom and control of his current work over the potential financial gains of a venture capital position.
• The discussion highlights the importance of aligning personal values with professional choices.

"I don't want to raise money because then I'd have bosses and I don't think I'd get a valuation that I'd be happy to sell part of myself for."

Paki's quote emphasizes his preference for independence and control in his work, valuing these aspects over the financial and structural changes that would come with joining a venture capital firm.

• Paki describes the "Not Boring Flywheel," which includes audience, founders, and sponsors.
• The interconnected nature of content, audience, and investing is discussed.
• The flywheel concept is used to illustrate the self-reinforcing aspects of his business model.

"Audience at the center of the flywheel is maybe not exactly the thing. Like, if I had a million person audience of people who didn't care about startups or whatever, it wouldn't be kind of as powerful."

The quote highlights that the core strength of the flywheel is not merely the size of the audience but the alignment between content, the specific interests of the audience, and investment activities, creating a synergistic effect.

• Paki discusses the impact of audience quality on securing investment opportunities.
• The distinction between audience size and audience engagement is made.
• The relevance of audience members' familiarity with his content to investment discussions is considered.

"The divide is, did the person actually read not boring before and really get value out of something that I've written or not?"

This quote underscores the importance of audience engagement and familiarity with Paki's content in determining the success of investment opportunities, rather than focusing solely on audience size.

• Ben Gilbert and David Rosenthal discuss the valuation of media companies and the impact of founder dependence on multiples.
• The conversation explores the long-term orientation of public company shareholders and its influence on valuations.
• The unique challenges of valuing creative and media businesses are highlighted.

"Hamilton Helmer makes the point that actually public company shareholders are not short term oriented, they're long term oriented."

The quote from Ben Gilbert references Hamilton Helmer's perspective on shareholder orientation, which is used to frame the discussion on the valuation of media companies and the implications for businesses like Paki's.

• Paki McCormick and the hosts discuss the difficulty of articulating and replicating the creative process.
• The uniqueness of Paki's content creation process is likened to a form of "process power."
• The conversation acknowledges the intangible aspects of producing quality content.

"You could not write a document such that you could hand it to someone else and they could do your job like that."

Ben Gilbert's quote captures the idea that Paki's creative process is unique and not easily transferable, suggesting that it is a distinctive advantage that contributes to the quality and success of his content.

• Paki considers the possibility of managing a larger fund through Not Boring Capital.
• The implications of scaling the investment strategy and the potential changes to the business model are discussed.
• The conversation explores the evolution of individual investors into larger funds.

"It's such an interesting question because I keep telling myself no."

Paki's quote reflects his hesitation and the complex considerations involved in potentially scaling Not Boring Capital to manage a larger fund, highlighting the differences in strategy and operation that would be required.