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

What I struggled with:

• No struggles this week.

What I learned:

• The International Institute of Information Technology Hyderabad is a university in India that’s well known for its curriculum around natural-language processing. Alumni and students from this school could be a good fit for my project.
• The opportunity solution tree framework in Continuous Discovery Habits is helpful. It’s a great way to lay out customers’ mini pain points and brainstorm solutions that can help resolve them. It helps you determine which pain points are the highest priority and can be solved in a way that aligns with your business objectives. The book doesn't say this, but the most important and highest level is a major customer problem or need. Adding this to the framework helped me tremendously and focused everything on the customer’s pain.
• Capturing, recalling, and using what I learn from mediums like YouTube to solve problems is just as challenging as it is with books. See more here.
• The brand journey framework is a good way to think about how to create a brand intentionally. You start with your goal and work backward to today by answering four questions:
  
  • 1. What outcome do you want, or what’s your motivation for doing something?
  • 2. What do you have to be known for to get #1 to happen?
  • 3. What would you have to do to be known for the thing in #2?
  • 4. What do I have to learn right now to do the thing in #3?
  • For a more detailed explanation, see here.

That’s what I learned and struggled with last week.

I’ve been learning more about copywriting, which most people think of as writing that makes people buy something. That’s true, but it’s more than that. It’s about persuading or influencing someone, but with the written word instead of oral communication.

I’m not great at persuasion, but I’ve always wanted to get better, which is why I’m curious about copywriting. When I read the biographies of advertising and public relations entrepreneurs Albert Lasker (see here and here) and Edward Bernays (see here), I realized that I don’t understand the fundamentals of persuasion. Before I dive into the tactics of writing persuasively, I want to learn the principles underlying them.

Influence is a famous book by Robert Cialdini. I’ve heard nothing but good things about it, and it’s been mentioned in several biographies as having an outsize impact on entrepreneurs. I’ve owned this book for several years but never read it. But that’s about to change—I’m going to read it soon. I hope it helps me understand the principles of persuasion so the tactics I learn regarding persuasive written and oral communication will be more effective.

I listen to YouTube every day. It’s one of my preferred daily learning methods (see here). I even pay for the premium version, and it’s money well spent. As I’ve ramped up my use of YouTube, I keep running into the same pain point. Today I hit it again.

A few weeks ago, I listened to an interview on YouTube in which an entrepreneur shared one of his tricks for improving his decision-making when something isn't working. It was a good trick that stuck with me (high level, at least). Today, I wanted to use it but couldn’t remember the specifics. I tried to find the interview without success. I know who said it, but I don’t know which YouTube video he said it in.

It’s a pain not being able to quickly find a specific segment of a YouTube video I’ve watched. My current workaround is to search through my viewing history and try to figure out which video is the right one. Then, I search through the transcript to find the segment I’m looking for. Sometimes I find it, and sometimes I don’t. But in all instances, it’s a painful experience.

I’d love to use a tool that looks at my YouTube history, indexes the transcripts of the videos I’ve watched, and helps me identify the segment I need via a simple chat interface. I’d happily pay for this because it would enhance my learning and give me a repository of all the information I’ve consumed on YouTube.

If you know of a tool that can solve this problem, please let me know.

A few days ago, a friend told me about Reducto. The company just raised over $24 million from venture capital firms to solve the problem of unstructured data in PDFs by making it usable. It structures the text in PDF documents so you can feed it into other systems, such as LLMs or your own applications.

Some companies are building solutions that require information from PDFs to be fed into their software to achieve a desired output. They spend a significant amount of time figuring out how to extract unstructured information from PDFs, which isn’t as easy as it sounds. The issue is that this isn’t what these companies specialize in, so it takes them a long time to figure out. In many cases, they build something that’s decent but not great. Reducto’s PDF-processing service lets them skip mastering PDF extraction. They use the output from Reducto and focus on the more important aspects of the solution they’re building.

I spent some time playing with the tool’s free version. A few notes:

• Reducto can scan any document and turn the entire document into structured JSON. The free version has a 30-page document limit.
• The tool is incredibly good at extracting information from charts, which isn’t easy.
• There are many useful settings, including extraction method, chunking method, and more.
• The tool has an API, which is great for automation.
• If you need the extracted data formatted in a particular way, you can create a schema in Reducto, and the output will be formatted using your schema. I love this feature.

This is an impressive tool that solves a boring but big problem for companies. I can see companies quickly agreeing to pay for this service, which likely led to rapid growth in revenue and caught the attention of venture capital investors.

I get the impression this service is built for enterprise clients. I wonder if Reducto plans to offer something that’s more suited to small or midsize companies.

I recently chatted with an early-stage entrepreneur who built an app that enables businesses to accept almost any payment method. As I learned about the problem he’s solving, he mentioned that his target customers are “micro SMBs.” That caught my attention—I liked that framing.

“SMB” stands for small and midsize business. It’s normally applied to any company that’s not a huge enterprise. This bucket is pretty wide. For example, a midsize company might be a retailer with $75 million in annual revenue and 150 employees. A small company might be a graphic design shop with 10 employees doing $1 million in revenue. Though they’re both SMBs, their complexity and problems differ wildly.

The micro SMB is the smallest business in this group. I think of it as solopreneurs (i.e., the founder is the only employee) and teams of up to five people doing $500,000 or less in annual revenue.

For many years, I’ve been bullish on building a business that solves problems for SMBs as a way to build a large business. According to an older book by Verne Harnish, only 4 percent of businesses in the U.S. have revenue of more than $1 million a year. Translation: the market to serve small businesses is huge. If you can solve a problem they have, you can get a lot of customers.

I love going after micro SMBs because they don’t expect perfection, there are tons of them, you’re usually selling to the owner, and they make purchase decisions quickly. Solutions to problems they couldn’t solve themselves and solutions that significantly free up their time so they can work on other parts of their business do great in this market. They’ll often buy on the spot if you check either of those boxes.

One knock against micro SMBs by investors and founders has to do with the process of selling to them. Price points for solutions in this market are often lower, which means you can’t afford outbound sales teams in many cases. That’s true, but I don’t think it’s a negative. I think of this market as more of a prosumer market. You’re marketing to a sophisticated consumer who is more willing to spend than the average consumer. Instead of outbound sales, strategies that gain this customer’s attention or educate them can attract them. Easier said than done, but highly effective when done strategically.

My conversation with this founder crystallized something for me. I like serving the SMB market, but I love serving the micro SMB market. It’s a tough-looking market, but once you nail it you can build a massive business with customers who often won’t consider switching solutions because they’re too busy running their small business.

I’m committed to reading a book a week to learn and improve. Usually it’s a biography or autobiography because I get the most from reading about entrepreneurs’ journeys. I’m also committed to sharing what I’m reading in the library section of this site. Each week, after I read a book, I share it in my Learning Library, as it’s called now. My goal is to post a new book every Sunday.

This week, I shared a biography I read about Charlie Munger. Several books have been written about the life of his business partner, Warren Buffet, but I wanted to learn about Charlie’s journey, too—specifically, how he came by his multidisciplinary way of thinking and solving problems.

Damn Right! was just what I was looking for. Not only did it offer great insights into Charlie’s early career and tragedy, it also included great context about his businesses before Berkshire (including his hedge fund), his personal life, his quirky personality, and his commitment to multidisciplinary learning.

If you’re interested in learning more about Charlie Munger, consider reading Damn Right! by Janet Lowe.

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: 61
• Total blog posts published: 392

This week’s metrics:

• Books read: 1
• Blog posts published: 7

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

• Read Damn Right!, a biography about Charlie Munger  
• Finalized details of the 2025 Summer Uncomfortable Challenge
• Added this site to the Google Tag Manager platform

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Create an opportunity solution tree for this project
• Order books needed for the 2025 Summer Uncomfortable Challenge
• Tag specific actions on each page of this site to start collecting data in Google Tag Manager

Asks:

• If you know any senior full-stack developers interested in working on the software for my current project, please introduce us!

Week two hundred sixty-six was another week of learning. Looking forward to next week!

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

What I struggled with:

• For weeks, I’ve been looking for a developer to replace my friend. I’ve chatted with several developers but haven’t found the right person. This is frustrating because it’s slowing things down more than I anticipated.

What I learned:

• Ben Thompson’s Great Unbundling essay (see here) describes how technology and unbundling have impacted various media forms. This great piece articulates clearly how and why the media industry has changed. Notably, it doesn’t mention books. This essay got me thinking.
• An avid reader who shares his book reading and learning from books on X (formerly Twitter) is doing the same manual note-taking and highlighting that I do.
• Quotes and maxims are valuable and resonate with people. The person mentioned above keeps a file of quotes from the books he’s read. I’m stealing his idea.
• Cold outreach via X works well when you have a body of work to share that complements what others are doing. It establishes your credibility.
• The issue with sharing information from books is that they’re full of unstructured text. Tools like Reducto focus on the unstructured text problem. Investors are getting behind these companies (see here). These tools might be useful because we might not have to build extraction tools from scratch.
• I played around with Google Tag Manager for the first time. I’m aiming to start tracking information that’s more granular on this blog.

Those are my struggles and learnings from the week.

One of my friends told me today about an interesting start-up. It’s called Reducto, and it’s a service that turns “unstructured documents into useful insights.” The team just raised $24 million from several venture capital firms to fund its growth.

During my testing for my book project, I learned that it’s hard to feed large amounts of unstructured text to large language models, and finding insights was challenging. The responses were inconsistent or useless.

I’m curious to play with Reducto’s free playground to see how its platform addresses this problem.

This week, I met an early-stage entrepreneur. We discussed his fundraising strategy and pitch deck. He began by telling me about his background. As I listened, I could tell he’s bright and has a deep understanding of the problem he’s looking to solve and the market—but that wasn’t being conveyed in his deck.

His pitch deck jumped straight to the problem slide.

During our conversation, he established credibility before telling me about the problem. His work experience and a failed start-up gave me a glimpse of his drive and intelligence. He then told me how he discovered this problem and described all his research around it. At that point, I was hooked and engaged in his pitch.

His deck didn’t establish credibility and didn’t have a humanizing aspect (except a team slide at the end). So, the pitch didn’t resonate with me and likely wouldn’t with anyone else.

Early-stage entrepreneurs are selling themselves and their vision. Their decks should reflect this. It’s easier for someone to engage with a pitch when they sense that the person who created the pitch is worth listening to.

Think of an early-stage pitch as a conversation on paper. When you meet someone for the first time, you don’t jump straight to what you want from them. You introduce yourself and give some background info so they can get comfortable with you and become receptive to what you’re about to ask or tell them. The beginning of an early-stage pitch deck should resemble the beginning of an introductory conversation—it should establish credibility to help the reader be receptive to your pitch.