For the last few podcast series I’ve published, I created digests of the books beforehand—a time-consuming process. Combined with recording and editing the podcasts, a significant time commitment was required.

This process left me with an uncomfortable feeling. I was spending a considerable amount of time executing—sharing what I’d learned—and not enough time strategizing the best way to share what I’d learned and how to scale my idea. I felt like I was falling into the founder trap of working in the business and not working on it (even though I technically don’t have a business yet; it’s just a project). This is dangerous because you can end up on a hamster wheel going nowhere fast.

It was unsustainable, so I slowed down and eventually paused publishing more podcasts until I found a way to create the digests more efficiently using technology. I’ve tested some technologies but haven’t found anything that has materially helped with digest creation. Since I haven’t found the solution, I haven’t published new podcasts. In retrospect, that was a mistake.

My goal is to share what I learn with others, and I haven’t been doing that at the level I know I’m capable of. That bothers me. Also, the podcast was an external and internal feedback loop that improved my communication skills.

I’ve decided to restart sharing what I’ve learned via podcast series. Because creating them takes a long time, I can’t get them out as fast as I’d like (weekly), but I shouldn’t let that stop me from doing it at all. I just have to do it at a slower pace for now. As I find new technologies that make the process more efficient, I can increase my publishing frequency.

Last week, I read Newhouse: All the Glitter, Power, & Glory of America’s Richest Media Empire & the Secretive Man Behind It by Thomas Maier. It was about the Newhouse family’s media empire but mainly focused on Samuel “Si” Newhouse Jr. I enjoyed the book, but I didn’t get a good grasp of the empire’s origin story. I’m also curious about the man who founded the empire, Si’s father Samuel Irving Newhouse Sr.

I decided to learn more about Sr., so I started reading Newspaperman: S.I. Newhouse and the Business of News by Richard H. Meeker. I’m still early in the book, but I already see clear differences between how Jr. and Sr. thought and acted as teenagers and young men. Both were great entrepreneurs, but Sr. had a founder’s and hustler’s mentality as a teen, which led him to found Advance Publications. Jr. didn’t really start to excel in the family business until he was in his 40s.

I’m sure there are way more differences between the two. I’m looking forward to finishing this book to compare the two further and understand how each achieved outsize success leading the same company.

As I understand Newhouse: All the Glitter, Power, & Glory of America’s Richest Media Empire & the Secretive Man Behind It, its author, Thomas Maier, said the Newhouse family was in the business of providing information to Americans. They owned magazines, newspapers, and cable systems, but newspapers were the empire's backbone. Growth potential was capped, but profit margins and cash flow were fat.

For many years, newspapers were the best way to distribute localized information, so they captured the attention of many readers. The Newhouses recognized this and executed a local monopoly strategy. Newhouse newspapers were often the only paper in town—the only way consumers could read local news. The papers, which had the attention of an entire community, were a microphone with which to talk to it. Companies paid a premium for the right to use the microphone to speak to the community, which drove highly profitable advertising revenue. Once a local monopoly was established, it was hard to compete with. It would generate predictable revenues and cash flows for years and wouldn’t require much reinvestment from the Newhouse family. The result was an annual stream of cash that the family invested into other businesses.

The book was first published in 1994 so it doesn’t capture how the internet disrupted their local monopoly strategy, but I’d imagine it negatively impacted their newspapers as it did the rest of the industry. The internet made information more readily available and made it easier for companies to reach consumers in a specific community. Meta (Facebook), Alphabet (Google), and others are now enormous companies and still growing quickly. Much of their revenue comes from advertising, which went to newspapers before the internet era.

The Newhouse family still has an empire, but I’m pretty sure that newspapers are no longer its backbone. I’m curious about how the family adjusted their strategy to respond to the internet’s impact and about what business is now the empire’s backbone. The Newhouse family’s companies aren’t publicly traded so information isn’t available via the SEC, but I’ll do some research and see what I can find.

For my personal project, I’ve been reading biographies about entrepreneurs and documenting and sharing what I learned from each book. My mission for this project is to create a library of wisdom from notable entrepreneurs that I and other entrepreneurs can use.

I’ve been playing with ways to create this library. Each time I’ve finished a biography, I’ve created a digest—my interpretation of the book and its most essential elements. The digests contain ideas and experiences from the entrepreneurs’ journeys. I use them when I’m trying to solve my own entrepreneurial problems. That usually involves reviewing a digest to find relevant experiences of an entrepreneur. It’s better than rereading an entire book, which saves me time. But it’s still not great because leveraging multiple digests simultaneously means reading multiple digests again. For the sake of time, I usually have to pick the one or two that I think are relevant.

Creating a library of digests or entrepreneurial wisdom is helpful but not enough. It’s still too hard to use all that wisdom. I’ve been exploring ways to solve this. I’ve been learning about retrieval augmented generation (RAG). I’m still new to RAG, but my elementary understanding is that it’s a way to improve AI responses. RAG allows you to provide a knowledge base to AI to complement its large-language model (LLM). The result is more-accurate responses—or it’s supposed to be, at least.

If I can complement an LLM with multiple digests and ask AI for suggestions on solving my problem, I can leverage the wisdom of all the entrepreneurs I’ve read about to solve a single problem. Or at least that’s what I hope.

I’ve encountered an issue, though. Implementing RAG appears to require some technical abilities, but I’m not technical. I need to test my thesis and have been looking for ways to use RAG. This week, a friend told me about the latest updates to Google’s NotebookLM. NotebookLM is a productized way for people to leverage proprietary data and AI easily. It’s basically RAG made easy for nontechnical people like me. I’m oversimplifying because it does lots of other stuff, but you get the point. NotebookLM is my best option right now, so I’ll test my thesis using it until I can get some technical help.

NotebookLM has come a long way in the few months since I first heard about it. I’m excited to play with the latest version to test my thesis.

Current Project: Reading books about entrepreneurs and sharing what I learned from them

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

Cumulative metrics (since 4/1/24):

• Total books read: 31
• Total book digests created: 12
• Total blog posts published: 175
• Total audio recordings published: 103

This week’s metrics:

• Books read: 1
• Book digests created: 0
• Blog posts published: 7
• Audio recordings published: 0

What I completed this week (link to last week’s commitments):

• Read biography about the Newhouse family and Samuel “Si” Newhouse Jr.

What I’ll do next week:

• Read a biography or autobiography
• Create a notebook in NotebookLM using one of my book digests and get feedback from two people on it

Asks:

• None

Week two hundred thirty-five was another week of learning. Looking forward to next week!

Current Project: Reading books about entrepreneurs and sharing what I learned from them via blog posts and audio podcasts

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

What I struggled with:

• No material struggles this week

What I learned:

• ChatGPT’s custom GPTs allow you to upload “knowledge”—documents that ChatGPT will use in responses. After I uploaded several of the book digests that I created, the responses to my questions weren’t great, even after many rounds of adjusting the prompting.
• Some historical books about companies or families don’t provide enough depth about an entrepreneur’s journey. Still, they’re great tools for discovering more entrepreneurs and books about them.

Those are my struggles and learnings from the week!

After I wrote a post earlier this week, I became more curious about Reddit’s business and how it complements the Newhouse family’s media empire. I shared some reported numbers about the business in that post but didn’t dig into the business or its SEC filings.

When I get some bandwidth, I’ll read its entire form S-1 SEC filing and maybe its latest 10-Q filing too. It’s a pretty nerdy thing to do, but I always learn a ton when I read S-1s about companies I’m interested in (see here and here). I have some other filings in my queue to read first, but I’ll share what I learn from Reddit’s filings when I finish reading them.

I’ve learned a lot about the Newhouse media empire by reading Newhouse: All the Glitter, Power, & Glory of America's Richest Media Empire & the Secretive Man Behind It by Thomas Maier. In my post earlier this week, I shared that the family owned 26.5% of Reddit when the company IPO’d earlier this year.

I did some digging and found no filings indicating that they sold any of their position. This SEC filing says there’s an agreement with the Reddit CEO to vote Newhouse shares (owned by their Advance Magazine Publications entity) for certain nominees to the board of directors. The probability is high that they still own their 26.5% stake.

As of the writing of this post, Reddit’s market capitalization (i.e., valuation) is $11.2 billion (see here), which means the Newhouse family’s stake is worth just under $3 billion. I was curious how a traditional media-focused company obtained sizable ownership in a technology company.

Steve Huffman and Alexis Ohanian launched Reddit in 2005. Roughly eighteen months later, in 2006, Condé Nast, another Newhouse family company, purchased Reddit. In this tweet thread, Ohanian referred to the company’s sale and a “$10M exit.” I’m not sure if that was his share of the proceeds or the entire transaction amount, so I’d assume the Newhouses acquired Reddit for roughly $10–$20 million.  

That was eighteen years ago, and a lot has happened since then, including several fundraising rounds. Assuming the family invested in some of those rounds and covered the company’s early losses for years, they likely invested more than the purchase price. But even if those assumptions are accurate, their investment has paid off handsomely. Reddit, a technology company founded roughly twenty years ago, likely represents a material percentage of this family’s empire, which was born about a hundred years ago with Advance Publications.

The family’s empire has historically consisted of mature media properties such as newspapers, magazines, and cable operations that grew steadily but not rapidly. How the family deployed the cash from these mature properties led to the accelerated compounding of their empire (and wealth). They used cash generated from their mature properties to invest in a technology company with high growth potential because the cost of marginal replication of its product was zero. Said differently, if one person or a million people use Reddit, the cost to run Reddit doesn’t change much at all, let alone proportionally to user growth. Reddit could grow revenue and value faster than the Newhouses’ mature media properties. The Newhouses’ investment in a company whose business model had built-in leverage was the shrewd move that led to an outsize outcome and rapid compounding.

I haven’t been a fan of books that tell the history of a company or a group of people (i.e., a family). These books introduce numerous people but don’t go very deep into any of their journeys. I enjoy biographies more because the in-depth coverage of a single person’s journey usually includes challenges encountered, lessons learned overcoming adversity, and details about how they applied lessons learned to achieve their goals. Biographies get me thinking and often lead to new ideas and insights, which excites me.

Though books about the history of a company or group of people aren’t my favorite, I now recognize they’re useful for something: links to other people or companies in an industry or time period.

I’m currently reading Newhouse: All the Glitter, Power, & Glory of America’s Richest Media Empire & the Secretive Man Behind It by Thomas Maier. It’s about the Newhouse family and their media empire. But because it covers so many decades and so many people, it’s introduced me to other companies and founders I wasn’t aware of. I’ve ordered biographies about several people mentioned in this book.

My thinking on the value of reading this type of book has changed. While I’m not learning as much about an individual as I’d like, I’m being introduced to more people in the publishing industry and can read about each person’s journey. These books are good discovery mechanisms and help me understand industry periods. I don’t want these to be the majority of my reading, but they’re a helpful supplement to biographies.

Last week, I shared a post about Roy Thomson’s strategy for growing his media empire. It focused on cash flow. He bought small-town newspapers, many of them monopolies in their communities, that had strong cash flows. The newspapers were low to no growth in some cases but generated healthy cash. Roy then used those yearly cash flows to purchase more cash-flowing newspapers and other media assets.

I’m now reading Newhouse: All the Glitter, Power, & Glory of America's Richest Media Empire & the Secretive Man Behind It by Thomas Maier. It’s about Samuel “Si” Newhouse Jr. and his family’s media empire. This billionaire family owns numerous newspapers through Advance Publications and also owns Condé Nast, which publishes famous magazines like Vogue, Vanity Fair, GQ, and The New Yorker. Advance Publications owned 26.5% of Reddit when it began trading on the public stock market this year (see here, page 194). As of this writing, Reddit’s market capitalization (i.e., valuation) is just under $12 billion.

As I read more about Si and his family’s growth strategy for their media empire, I see that it’s similar to that of the Thomson family and others, including Warren Buffett and Mark Leonard of Constellation Software. The Newhouse family initially purchased cash-flowing newspapers and used the cash from those businesses to buy more businesses. They’ve done this over decades and built a sizable empire.

It’s notable that several people (and families) who’ve achieved outsize business success have used a similar strategy.

I’m curious to learn more about the Newhouse empire and family members, especially the patriarch, Samuel Irving Newhouse Sr.