One insight that resonated with me when I read How to Get Rich in American History was about retirement. The author said that one of the 25 financial ideas that have worked throughout history is “Do not obsess over early retirement.” His point was that throughout history, most people who became wealthy didn’t stop working. Their wealth made them self-sufficient, so they spent their time doing what they wanted. Often, they wanted to work (and many wealthy early retirees go back to work). Retirement has historically meant having control over what you choose to pursue and work on, not choosing to not work.

I agree with this point. In 2023, I shared the insights I gained from taking extended time off. My conclusion was that “[m]y retirement plan is to never retire.” You can see my explanation here.

After reading 300 years’ worth of history, the author came to a conclusion similar to mine. It’s good to know that my stance is supported by history.

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This weekend I caught up with a friend who’s an entrepreneur. His company builds single-family homes. I love chatting with him because we operate in completely different worlds. His world is coordinating with skilled laborers building million-dollar-ish homes. But this weekend our conversation was different. He was excited to tell me about how he and his peers have embraced AI.

My friend shared that another builder was struggling to sell his completed spec homes. The carry costs were adding up, so the builder was anxious to sell them. The builder’s granddaughter told him to use ChatGPT to help him with his problem. The builder isn’t tech savvy (he’s in his 70s), but he figured he didn’t have anything to lose. He fired up ChatGPT, and after some dialogue it suggested a marketing strategy that included offering rate buydowns and other incentives to incentivize buyers and their real estate agents. These types of incentives aren’t new, but they were foreign to the builder because he left the marketing and financing to his real estate agent and banking partners. Nevertheless, he took the advice, instructing his agent and bankers to follow the strategy ChatGPT suggested. The result: the homes sold in a few weeks. The builder’s mind was blown, and he now uses AI regularly to talk through ideas and problems.

My friend is more tech savvy, but he hasn’t needed to use AI for work. Recently, though, he’s been using AI to build a side-hustle e-commerce business for his wife. Within a week or two, he had a name, branding, a strategy, and a manufacturing plan. He and his wife are now aiming to launch the brand soon. He was amazed that AI was able to take his wife’s idea, help him work through the unknowns, and get it to a stage where it’s close to launching. This normally would have taken months and thousands of dollars paid to designers and other contractors. AI now has him thinking about other business ideas he can test cheaply. In his free time, he’s using AI regularly now.

This weekend confirmed something I’ve been thinking for some time. When Main Street entrepreneurs (i.e., not tech entrepreneurs) learn how to leverage AI, a massive wave of entrepreneurship will be unleashed. As more people who deeply understand problems and how to solve them pair with AI that can turn their ideas into reality, we’ll see more people embrace entrepreneurship.

Today I had an interesting chat with an entrepreneur about his new businesses and the trends that led him to start them. Here are a few trends that stuck with me:

• Big brands – Younger consumers don’t want to buy from big chains or brands. They want local brands they can relate to. He thinks chain restaurants will suffer massively.
• Analog – People are tired of screens and craving real-life experiences and connection. Products that enhance in-person engagement or experiences will win.
• Alcohol – People, especially young people, are drastically reducing their alcohol intake. Places where people can socialize that aren’t bars or clubs are needed.
• Tech – Technology isn’t a moat anymore. What’s important now are brands that resonate with people and distribution that puts those brands in front of people.

Interesting insights. I definitely see anecdotal evidence of these trends around me in Atlanta, especially with young adults.

Last week I read Afro Sheen, the autobiography of George E. Johnson, founder of Johnson Products Company (JPC). I learned about Johnson last month when he died and I read the Wall Street Journal’s write-up of his life (see here). The article intrigued me and reminded me of John H. Johnson (no relation), another Chicago entrepreneur who had a dramatic influence on Black culture over many decades. John H. Johnson’s autobiography (see here) was one of my favorite reads in 2024 and really solidified for me the power and influence of media companies that serve niches.

George E. Johnson’s autobiography is full of stories about encountering and overcoming challenges, and one key personality trait that I picked up on was Johnson’s ability and desire to self-educate. He didn’t have much formal education; he dropped out of high school. But his desire to succeed and lift himself out of poverty fueled an insatiable desire to learn his way out of problems and learn new things just for fun. Two vivid examples from the book stuck with me.

Johnson was notoriously afraid of flying. He had to fly for business, but he hated it. He decided that the best way to overcome his fear of flying was to learn how to fly a plane. Learning to fly forced him to learn the principles of aviation. Once he understood why certain things happen to airplanes, his fear of flying was cured. He even took things to the next level and bought a single-engine plane so he could fly himself for business and pleasure.

Johnson recognized early on that marketing directly to the Black community was difficult. But when color televisions became popular in the 1960s, Johnson saw an opportunity. Not only did he learn how television advertising worked, he took it further. He recognized that advertising on shows that didn’t serve his target customer didn’t make sense. Wanting to make sure his ads spoke directly to his target customer, he decided to create a TV special that his customers would love. In 1969, …& Beautiful aired. It featured Redd Foxx, Della Reese, Wilt Chamberlain, and others. Johnson had learned television advertising and television production.

…& Beautiful led to Johnson meeting Don Cornelius, then a disc jockey at a local Chicago radio station. The two partnered on a new TV concept called Soul Train, which became a multi-decade television success and skyrocketed the sales of JPC products nationwide. Johnson was an advertiser on Soul Train and owned 50% of the show at one time (read the book to find out how generous he was to Cornelius). Through Soul Train, Johnson learned about syndication. CBS, ABC, and NBC turned the show down, but Johnson purchased airtime on independent stations in nine markets with large Black populations. The result was that Johnson and his team set the stage for Soul Train to become the first nationally syndicated television show. Johnson learned the business of TV and used it to supercharge JPC’s marketing efforts and sales.

Johnson’s life is a great rags-to-riches story. Its through line is continual self-education and drive by someone who refused to be defined by his starting position in life.

This week I had lunch with a friend who’s an entrepreneur. His business sells software and services. Think software company with an attached agency. One thing he shared was that he has drastically reduced headcount and become more efficient as a CEO, so he has more personal time. This friend is a software developer by training, so I figured he was using AI to accomplish this.

I was right. AI agents that he built have helped him get more done faster, leaving him more bandwidth for personal pursuits. As he described how his agents work and what output he receives, I thought, “He’s built an AI that’s his chief of staff.” I shared what I was thinking, and he said yes, that’s exactly what he’s built. For $200 a month!

I’ve found that seeing how others are using AI is a great way for me to learn and expand my thinking around its possibilities. I asked him if he would walk me through his setup, and he agreed. I’m excited about seeing what he’s built and how he’s using it. I’ll be sure to ask lots of questions. This might spark some great ideas for things I want to build.

As I shared yesterday, I read The Bond King, a biography about famous investor Bill Gross and the investing empire he built with PIMCO. Two other things stood out to me about Gross’s story that I’ve been thinking about this week.

Even though he founded PIMCO, Gross wasn’t an entrepreneur. He started PIMCO as an experiment within the insurance company he was working for in the 1970s, Pacific Mutual Life Insurance Company. Pacific Mutual gave him and a few others $5 million to test out their bond strategies. By taking the intrapreneur route, Gross could enjoy a comfortable salary, not spend months or years trying to raise money from LPs for a fund, and use the resources and infrastructure of his employer. PIMCO made Gross a billionaire even though he wasn’t an entrepreneur and his risk was significantly reduced.

The other thing that stood out to me was the culture at PIMCO. It was sharp-elbowed and competitive, which helped them for decades. They pushed the boundaries, and it doesn’t sound like it was a fun place to work. It was an intense pressure cooker that paid extremely high salaries. People hated it, but they couldn’t leave. The culture Gross created ended up being a big part of the reason he was forced to leave abruptly.  

Bill Gross and the PIMCO story are fascinating. He’s a super-eccentric guy. He accomplished a lot, but his eccentric ways had many downsides.

I read a quote today that caught my attention:

Before you play the game, study the winners. If you don’t want their life, don’t play their game.

I totally agree. Winning at competitive games that have power law outcomes isn’t a walk in the park. It requires an immense amount of consistent work that others don’t see. People competing at these levels often build their lives around their work habits, but nobody sees that. They see only the win at the end.

Everybody wants to be Kobe Bryant and win five championship rings, but nobody wants to get to the gym every day at 5 a.m. for private practice before the team practice later that morning.

I’m a fan of studying the greats of a game before you try to play. You’ll get an idea of what it takes to win.

Helping my friend grow his start-up over the last few weeks has solidified something for me about selling physical products. You can now build a massive company, in terms of revenue and units sold, with a very small team. I believe you can easily reach $10 million in revenue with a team of three or four people. You can probably get to $50 million with a team of eight to ten people. And you can get to $50 to $100 million in two or three years. This was unheard of when I started CCAW.

So, what changed? AI is one of the obvious answers. Each person can be much more productive than before. And some tasks can be easily handled 100% by AI. But an equally big change is what I call infrastructure as a service. Think Amazon Warehouse Distribution (AWD), Amazon Multichannel Fulfillment, and TikTok Multichannel Fulfillment. The infrastructure needed to scale massively doesn’t need to be built from the ground up or managed. You can just rent the capacity you need when you need it. Combine that with outsourced manufacturing and demand-generation platforms like TikTok, and you can now scale massively in a short amount of time.

You used to need a team of builders, executers, and managers. Today you just need a few high-level strategic thinkers who don’t mind getting into the weeds and who can manage service providers closely.

This is a massive change in the landscape of selling physical products.

For the last few weeks, I’ve been helping a friend scale his start-up. His company sells its own branded physical product. One of its biggest pain points has been logistics; specifically, shipping companies picking up and delivering products undamaged and on time. If you don’t have room for error, then a small shipping issue can ripple and cause much larger problems.

I’ve dealt with lots of shipping companies, and I saw them make all kinds of crazy mistakes when I was running CCAW. Over the years, I learned a few things:

• Things are going to happen. When they do, learn from them and try to identify ways to prevent them in the future. Document those learnings somewhere.
• Processes for dealing with shipping companies make resolving errors more efficient and help get things back on track faster.
• The cheapest shipping company isn’t always the best choice because you’ll pay for the money you save with time and energy.
• There’s a big difference between small-parcel (e.g., UPS and FedEx) and less-than-truckload (LTL) shipping. LTL is like the wild, wild west. Small-parcel networks are highly tuned systems built by industrial engineers. LTL networks, not so much.
• Check your bills. Overbilling is rampant in the shipping industry.
• Shipping to consumers and small businesses is very different than shipping to warehouses and distribution centers (DC). The latter have lots of products and trucks coming and going, so it’s hard to get a clear answer on the status of a single shipment. If you’re shipping to a warehouse or DC, it’s helpful to understand how the location operates before you ship there. Some require appointments or other extra steps.
• Small-parcel shipping has historically been a duopoly with FedEx and UPS, but that’s changing now with Amazon Shipping and other last-mile service providers.
• The cost to ship to a residential address is very high, which historically has made it prohibitively expensive to ship certain types of products to residences. Amazon Shipping and other service providers are changing this as we speak, though.
• If you’re shipping a material number of packages daily, a central system where you can see the status of all shipments across all carriers and locations is crucial. Separate systems that don’t talk to each other create chaos and make it difficult to scale and run a smooth operation.
• Labeling and preparing shipments properly can help prevent 50% of issues down the road.

That isn’t a comprehensive list, but if you address everything on it, you’ll drastically increase your ability to scale and the chances that you will scale, and you’ll catch and fix issues faster, prevent issues, and save on shipping expenses.

A little over a month ago, I began testing a one-page daily report card. Learn more about the idea and my experiment here. I now feel that I have enough data to evaluate this experiment and what I’ve learned from it.

I’ve decided that I like this habit. It feels like a natural extension of my blog-post habit that’s focusing on daily execution. Starting each day by detailing what I want to get done and ending the day by listing what I actually did has helped illuminate the gap between the two every day, which helps me recalibrate for the next day. The sections on mistakes and lessons learned are useful because they force me to stop and think about what I did wrong (no shortage of material there) and what I learned from those mistakes. Reflecting on this daily has led to insights that have helped in my daily recalibration. Grading my time in two-hour blocks has surfaced patterns that I might not otherwise have noticed.

Overall, this habit is a way to create an accelerated feedback loop on how I work. I’m evaluating myself and reflecting every day, which lets me make micro changes every day. I can see how making small improvements daily (e.g., 1%) would compound to big changes over a longer period.

Will it become a long-term habit like this blog? Time will tell. It’s still an experiment, but right now I’m getting value from it, and it’s challenging in a fun way.