Last year, I read a book by Felix Dennis. The title—How to Get Rich—isn’t my favorite, but it grabs people’s attention. The book is about succeeding as an entrepreneur, which leads to wealth—it’s not just about how to get rich. Dennis shares numerous lessons he learned the hard way as he built several companies, including Maxim magazine.

The book is a good read and contains lots of useful lessons for entrepreneurs. To see my takeaways, read my blog post series here.

One takeaway that stuck with me is about persistence and stubbornness. I regularly ask myself if I’m being persistent or stubborn when things aren’t going as I’d hoped. Here’s how Dennis describes the difference between the two:

Persistence is having the conviction that you’re right about something and that your point will be confirmed in the future (hopefully shortly). You simply keep going until you’re proven right. This is what entrepreneurs are known for. Simple enough, right? Well, how does persistence differ from stubbornness? Stubbornness is a form of persistence. You persist at something because you think you’ll be proven right. Stubbornness comes in when data or other evidence points to your likely not being right. Said differently, stubbornness is persisting even though signs are pointing to your being wrong.

Persistent people keep going, but they pay attention to red flags. If they’ve made a mistake, they change their plans. They persist, but in a different way—one that’s more likely to be successful. Stubborn people keep going and never course correct when they should.  

I think of persistent people as rational, clear thinkers. They’re grounded in reality and have the mental flexibility to acknowledge when they’ve made a mistake or bad decision. They acknowledge their error, regroup, and refocus their energies on the right activities so they can still achieve their goal.

I was stubborn once. I ignored signs that I was going hard in the wrong direction, and I regretted it. I vowed to do my best to avoid those kinds of mistakes going forward. Since reading Dennis’s book, I regularly ask myself if I’m being persistent or stubborn. I look for signs or data points that signal that I might be right. If I can’t come up with any, I know I’m likely being stubborn and need to course correct and put my energy into different actions that still align with my goal.

Last year, I wrote a post (see here) in which I defined wisdom:

Wisdom is the ability to apply knowledge in a manner that aligns with the outcome you desire. Wisdom means changed behavior and improved decision-making—knowing what to do and when to do it. Wisdom is acquired from experience (yours or someone else’s).

Wisdom is the entrepreneur’s friend because it allows them to hit their goals (e.g., grow their company) faster. Acquiring wisdom from the experiences of other credible entrepreneurs is best because doing so saves a significant amount of time.

How entrepreneurs acquire wisdom from others is something I’ve given a lot of thought to—after all, I’m reading biographies to do just that. Entrepreneurs pay lots of money to be in communities with people going through similar experiences so they can learn from them (EO, YPO, Vistage, Hampton, etc.).

I’ve been thinking about the difference between first-generation and second- or multi-generation entrepreneurs and how the acquisition of wisdom impacts their respective velocities, which is more important than their speed (learn why here).

I’m going to learn more about this, but I hypothesize that second-generation entrepreneurs have a material advantage starting out because they’ve acquired significant wisdom through osmosis from being around and talking to family members who are entrepreneurs. They learn from an early age what works and doesn’t work, and why, from experiences of family. So, when they start their own companies, they have a better idea of what to do and when to do it. Does that mean a second-generation entrepreneur is more likely to be successful? I don’t know. Does it mean a first-generation entrepreneur competing against a second-generation entrepreneur needs greater learning velocity? Likely so.

I’m curious about this and excited to learn more. I’m going to talk to a few entrepreneur friends who grew up in entrepreneurial families to get a feel for whether my thesis is directionally accurate.

This week I caught up with a buddy who’s a software developer. He’s been working on a software idea that he hopes will become a large business. The scope of the project is sizable, so he’s had to hire a few developers to help him get it over the finish line. He shared with me that he’s learned a lot from the experience, the main thing being that he doesn’t want to work on any project that he can’t build by himself. He doesn’t want to manage other developers. He just wants the freedom to work on software ideas he’s curious about, launch them (and hopefully get revenue), and move on to the next project.

As I listened to my buddy, I thought about the indie hackers I’ve researched. The notable ones have one-person shops that have built a portfolio of several companies that collectively generate several million dollars in revenue each year (usually, one of them contributes the most revenue). From what I’ve learned, indie hackers love the process of building but also love new challenges. They don’t want to work on something indefinitely. They want to be individual contributors and work alone so they can move really fast. And most importantly, they want freedom—they want to be in the driver’s seat of their own lives.

I’m pretty sure my buddy is an indie hacker, but he might not realize it yet. I have a lot of respect for indie hackers. I think it’s amazing that they can do what they love; build cool, new stuff; turn it into companies; and generate enough revenue to give them financial freedom (in some cases, serious wealth). What I respect most about them is that everything they do is on their own terms.  

Not every software engineer wants to work at or build a large company. Some just want to continuously work on new ideas they find cool and be in control of their life. They don’t want to rule the world; they just want to live in it the way they see fit. I love it, and I think the indie hacker movement is a great part of the entrepreneurial ecosystem that will likely get much larger and well known in the years to come.

This week, I had a conversation with an early-stage founder building an AI company to help large companies manage software development. He recently completed a substantial fundraising round. He’s from Atlanta, founded his company here, and was splitting his time between San Francisco (SF) and Atlanta, but he recently moved full-time to San Francisco.

I was curious about why he moved, and he told me he had two main reasons:

• Talent – Only a few hundred people in the world know how to train large language models the way his company needs them trained, and those people are all in SF. He needs to be there to recruit talent.
• Ground zero – The biggest breakthroughs are happening daily in SF. When you’re there, you’re working alongside the people making them. Because you know what they’re working on, you can build complementary products six or eight months before other people—who aren’t even aware the breakthrough is coming. Additionally, being physically closer to large-model companies like OpenAI enables you to gain access to useful information such as product roadmaps, which allows you to stay ahead of the curve in your building and decision-making.

This founder’s perspective is unique, given his knowledge of and deep entrenchment in both cities. I found it helpful. I understand why he moved to SF, but I’m hopeful that Atlanta will attract and produce more AI talent over the next few years, making it feel like ground zero. If so, hopefully, talented AI founders won’t need to move to achieve outsize success.

I’ve been chatting with an early-stage founder and providing feedback about his pitch deck. He’s sharp and a go-getter, and I enjoy working with him. He’s looking to raise a seed round from a venture capital firm and wanted my thoughts, since I’ve been inside an early-stage venture capital firm.

One of the things I’ve been questioning is the problem he’s trying to solve. He wasn’t stating it succinctly—he alluded to it, mentioning other problems as well. It was up to me, the reader, to reach the correct conclusion about the main problem he’s solving. I’d talked to him, so I could do that, but what about the investors who see a few pitch decks a day and would see his pitch cold? They won’t take the time to try to figure out the problem; they’ll just say no and move on to the next pitch deck.

Businesses exist to solve a problem for their customers. Customers pay for that solution if it provides value to them. It’s that simple. The customer’s problem is the foundation of the business. Solve their problem in a way that customers value, and they’ll pay you for that value. If you can’t articulate the problem clearly, that failure cascades through all aspects of the business and makes everything harder. Raising money and closing customers is harder, and even recruiting may be more challenging.

Understanding the one main problem you’re solving and communicating it clearly is harder than it sounds. If you can’t articulate your problem in a way that people instantly understand (even if they disagree with it), consider spending some time refining it and getting feedback until you nail it. Getting this right as early as possible will give you a north star that will make decision-making, fundraising, and a host of other things easier (not easy!) down the road.

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.

Reading Netflixed, I learned about an entrepreneur I’d never heard of. His name was Andre Blay. He was the man who created the market for VHS tapes and a multibillion-dollar industry, VHS rentals. That industry birthed tens of thousands of video rental entrepreneurs and led to the creation of Blockbuster Video. And he did all that in a few short years.

I want to learn more about him and how his vision led to a multibillion-dollar industry. He wrote a memoir that’s nearly impossible to find at a reasonable price, but I’m determined to get a copy. When I do, I’ll share what I learn.

Students versed in AI are concerned because entry-level software developer jobs are hard to land.

This week, I spoke with a computer science student at a top-tier school known for computer science. He’s about two years from graduation and already all in on AI. He’s creating side projects and is well versed in the latest technological developments.

He said the job market is tough for entry-level software developers (and internships). He and his friends are looking for ways to gain more practical AI experience to increase their chances of getting full-time roles after graduation.

As he talked, I couldn’t help but think of myself and early-stage entrepreneurs. I haven’t found the right developer to help with the next phase of my book project. And I know several other entrepreneurs with internal and customer problems they think AI can help solve, but they too haven’t found the right talent to help them.

I’m out of touch with the job market for entry-level software developers. But if it’s as tough as this student says, then helping entrepreneurs build AI solutions to sell or use internally is a great option for students. They would learn how to use technology to solve real problems and get to see firsthand how doing so creates value for a business. That experience could give them a leg up in recruiting or give them the know-how and confidence to start their own company to solve a problem.

This week, I had a long conversation with an entrepreneur who owns retail stores. The conversation centered on how tariffs are impacting her business. Most of the items she sells are imported from China. The only other countries with manufacturing capabilities are also subject to high tariffs, albeit lower ones than China. So, shifting to other countries wouldn’t solve her problem.

This entrepreneur traveled to the West Coast to understand how her wholesalers are planning to react. It wasn’t good. Some are raising prices to reflect the full tariff amount. Others plan to close up shop and walk away (after decades in business).

This entrepreneur’s wholesale costs will more than double, and she will likely have to double her prices. The challenge is that she doesn’t think her customers will be willing to pay double. She figures that revenue will decline regardless of what she does; the question is how much.

She also shared that she’s now considering starting other businesses. The possibility of her retail store failing for reasons beyond her control is real. It’s forcing her to be open to new opportunities in other industries to pay the bills.

I don’t know what will happen with tariffs. I suspect lots of entrepreneurs are rattled and thinking about plan B. I’m curious about what this will lead to. We could see a burst of entrepreneurial activity. When entrepreneurs’ backs are against the wall, they’re forced to do their best work. With tons of them facing this situation at the same time, some good is bound to come out of it.

AI is a hot topic among entrepreneurs right now. It’s a fantastic technology that makes the previously impossible possible. In the last few weeks, I’ve talked to several founders who want to use AI in their companies. They’re thinking along the lines of chatbots and other features. This struck me as odd because it’s not clear if these things would add value to their customers.

After I left one of these conversations, I realized that the founder is building technology in search of a problem. To his credit, he knows that AI is powerful and can change his company and benefit its customers. But he just doesn’t know enough about the technology to determine how to apply it in his business. So, he defaulted to building what he’s seen be successful at other companies: chatbots and the like.  

Companies exist to solve problems. By solving problems, they add value to customers, and customers pay them for that value. If a technology doesn’t help a customer materially or help you help the customer, what’s the point of using the technology in your business?

AI is powerful, and all entrepreneurs should explore and use it in their businesses. I think the best approach to adopting it, if you’re unfamiliar with it, is to pinpoint a problem that’s painful for you or your customers—one that you can’t solve or that’s painfully expensive to solve. Then, search the numerous AI tools for one that can help you solve that problem. Evaluating each AI tool to understand whether it can do that will expose the limitations of each tool and the technology as a whole. This process will accelerate your AI learning and help you get comfortable with the technology.

This approach will help you create a better solution for yourself or your customers and give you a deeper understanding of AI capabilities that you can use to solve future problems.