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.

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!

A friend read my post about reading multiple biographies and autobiographies to understand an industry. He suggested that I also read books that explain how an industry works. His argument is that information in these books will fill gaps in my understanding of the industry that exist because everything isn’t covered in biographies. Reading both should give me a superior understanding.

I’m always open to trying new things, so I agreed to read a book on the media industry, given the biographies I’ve read recently. I’m going into this with an open mind, but I have some reservations. I learn best by hearing about the experiences of other people. If there’s no story, no personal journey, it may be harder for these books to keep my attention. We’ll see.

I’m excited to see if doing what my friend suggested resonates with me and leads to a better understanding of the media industry, or at least a subset of it.

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

Cumulative metrics (since 4/1/24):

• Total books read: 30
• Total book digests created: 12
• Total blog posts published: 168
• 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 Roy Thomson and his son Kenneth Thomson
• Created first draft of a pitch deck
• Located commercial-grade book scanner in Atlanta
• Had one additional feedback session

What I’ll do next week:

• Read biography about Samuel “S.I.” Newhouse Jr.
• Continue tweaking the pitch deck
• Continue tweaking custom GPT

Asks:

• None

Week two hundred thirty-four 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:

• The more information you upload to ChatGPT’s custom GPTs, the more the quality of returns diminishes.
• Study groups (e.g., Bible study groups or book clubs) are valuable because they bring people together to share ideas about what they read. The varied interpretations and perspectives are helpful.
• Chronology is likely the best framework for a dataset that captures a person’s journey.

Those are my struggles and learnings from the week!

This week, I was asked several times about my personal project, so I took the opportunity to work on my pitch. A few learnings:

• Starting by describing the problem and the emotion it creates in entrepreneurs got people hooked. Then when I said I’m solving the problem, they wanted to talk more about their experience with it.
• Technically oriented founders dove deep into how to build the solution.
• Communicating the supply-and-demand dynamics around the problem helped people understand the size of the opportunity.
• Expressing the “why now” resonated with people.
• Shorter responses from me were better and led to a conversation about the problem and the solution.
• When I shared my vision, it missed the mark. I need to work on this.

Getting the pitch right is a process. The best time to start was yesterday. The more I pitch and work on my deck, the better it should get.

Last week, I shared my updated thoughts on reading multiple biographies about one entrepreneur. Multiple books provide multiple perspectives on an entrepreneur’s experiences, which gets me closer to a 360-degree view of that person’s journey. From a data perspective, I’ve been thinking about the best way to capture an entrepreneur’s journey so it adds value to others.

Multiple books can be written about a person, so there’s a one-to-many relationship between people and books. Therefore, a data record needs to be created for each entrepreneur, and information from various books enhances that record with details about the entrepreneur’s journey.

So, what’s the best way to structure this record for each person? I talked with a few developer friends with experience working with large data sets. Among other ideas, most strongly suggested that I create a proprietary framework optimized for entrepreneurs and fit details from each person’s journey into it. I didn’t like that idea for various reasons, so I continued to ponder. I asked myself, what biographies are best and worst at communicating an entrepreneur’s journey? And why? I also looked for clues in the digests I’ve created.

I realized a few things. The biographies I gained the most from portrayed an entrepreneur’s life with a clear, chronological story. The hardest to digest were the ones with lots of jumping between different periods throughout the book. The person’s journey wasn’t clear, or I didn’t know where I was in the journey. One of my favorite entrepreneur autobiographies, and a highly regarded bestseller, is Shoe Dog: A Memoir by the Creator of Nike by Phil Knight. I read parts of it again and concluded that one reason so many entrepreneurs like this book is its concise chronology of the struggles Knight endured in Nike’s early years. The book makes sure the reader knows where they are in Knight’s journey by making the title of each chapter a calendar year in Knight’s life (e.g., 1966). Chronology was a key to communicating Knight’s journey effectively.

I read a few digests that I created about books. In each one, I structured the information with a chronological tilt. It wasn’t intentional, so it must have been the best way for me to make sense of and document an entrepreneur's journey. I was trying to create a timeline of the entrepreneur’s journey.

As I thought about this more, I got comfortable with the idea that time could be my framework. Everyone has a birth date and a death date. Their journey is everything that happens in between. People learn from other people’s journeys and the wisdom they gain along the way. I can enhance every entrepreneur’s record in my data set with events and actions at specific times to chronologically document their journey. Every biography or autobiography helps create a clearer picture.

I still have more thinking to do around this, but chronology as a framework resonates as a logical way to organize a data set of entrepreneurs’ journeys.

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I had a good text exchange with a friend about my book project. It got me thinking. He said that because I’ve read so many biographies about entrepreneurs, in media at least, the wisdom is natively engrained in me and it will be hard for others to compete with me. Here are a few thoughts on this comment and our text conversation:

• I love it when people give me unsolicited feedback and ideas. It usually gets me thinking about things from a different perspective.
• Lots of entrepreneurs have read significantly more biographies about entrepreneurs than I have. True, I’ve done it at a rapid clip this year, but others have been doing it for years or decades and are far ahead of me. Consistent execution is the difference maker in something like this, especially when considering knowledge's compounding nature. If I can maintain this pace for years or decades, then I might have a shot at having an edge over others, but I’ve got a lot of ground to make up and I’m not doing it to get some title or prize. A big positive from this project is habit formation. I can comfortably read at least one book a week, and I think maintaining that pace for years is doable.
• To make something really stick in my brain, I have to do extra work. Reading doesn’t, by itself, ingrain in me the wisdom from an entrepreneur’s story. Creating the digest for a book forces me to understand their journey clearly and make connections (i.e., insights). Writing blog posts and creating a podcast series to share what I’ve learned forces me to get crystal clear on the strategies and ideas that propelled that entrepreneur. This entire process helps ingrain the wisdom and insights from each book. It’s time consuming, but it’s helpful. Doing it all manually isn’t sustainable, though.
• I don’t have a photographic memory. What I’ve learned is pretty fresh in my mind now, but to keep it at the forefront of my mind, I need to begin reviewing my highlights and digests regularly. Developing that habit will be painful—but a game changer, I suspect. Thirty minutes a day reviewing takeaways from biographies will be enough. I just need to cut out something that wastes thirty minutes a day to make room for this new habit.
• I want to lean into helping more entrepreneurs benefit from the valuable lessons in these biographies, but I don’t want to be the product. I want to share the information so others can use it as they see fit. I don’t want people to come to me to help them apply what I’ve read to their situation. I’m only one person, and that isn’t scalable. I want maximum impact; therefore, I can’t be the product. Figuring this out is top of mind.

Thanks to my buddy for initiating the text conversation that got me thinking!