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Last Week’s Struggles and Lessons (Week Ending 4/20/25)

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:

  • Copywriting Course is a great service for getting feedback on your messaging for a product if you already have product–market fit.
  • Google’s search algorithm changed about a year ago. Google began prioritizing blog content over other content types, such as lists.

Those are my struggles and learnings from the week.

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How I'm Fixing My Blog's Leaky Bucket

Last year, I wrote a few popular blog posts on biographies I’d read. Traffic to the blog increased, so people apparently found them useful. Since then, I’ve been trying to be more intentional with the blog. One area several people pointed to as a weakness was email capture. They said I was getting more people visiting the site, but they weren’t likely to read my new posts or come back to the site—unless I gave them a reason or reminded them. Capturing their email would give me a way to keep a reader I’d acquired engaged with (or at least aware) of my new material.

Email capture wasn’t something I ever thought about when I created this blog. People could enter their email address and be notified of new posts, but email capture wasn’t a priority. I never looked at the stats around how many emails I was capturing.

After hearing the same thing many times, I added a new feature a few months ago. A pop-up asking people to subscribe was added to the bottom of the site. Subscribers are notified of new posts.

The messaging in the pop-up was never really optimized. It was a placeholder to test whether the feature worked correctly. I’ve been learning about copywriting and am eager to put that knowledge to use. Today, I decided to adjust the pop-up message. I made some mistakes and broke some stuff, but it’s updated now.

This will be a process of iteration and experimentation, which is best done with data. So, I began tracking more subscription-related data. I can now experiment and see how effective changes are. I think these small experiments will be fun, and I’ll learn a lot.

If you have thoughts on this pop-up feature or the messaging, I’d love to hear them (criticism welcomed too). Write me at hello(at)jermainebrown.org.

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Books Read: Updates Coming This Weekend

The last month or so has been busy. Hitting my goal of reading a book every week has been harder, but I’m doing it. But I’ve slacked off in a related area. Earlier this year, I added this section, which shows the books I’ve read, to this site. My intention is to update that section weekly when I finish a book. I’m missing the mark in April—I haven’t added the books I’ve read this month.

I plan to fix that this weekend by adding my latest books. I aim to have the books added to my site by 12 p.m. ET on Sunday.

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Another Uncomfortable Summer Challenge

Last year, I set a goal to create 100 podcast episodes about the biographies I was reading. That challenge was uncomfortable, but it led to unexpected learnings. And it led to a new habit of reading a book every week (I’ve been doing this for over a year), my software idea, and other things.

I want to set another goal for this summer. It needs to be uncomfortable but directionally congruent with my current interests. I want something that will force me to grow by pushing me to the limit. Something I can focus on intensely with an end in sight.

I’m not sure what it’ll be, but my gut is telling me I should do something related to writing. I’ve been reading a lot about newsletters, copywriting, persuasion, etc. This challenge could be a good way to put everything I’ve learned to work.

I’ll think about it more, but another summer challenge is likely to be in my future.

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Tariffs Might Kill Stores—And Spark Reinvention

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.

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Tariffs Spooked His Investors—Now What?

I caught up with a founder who shared an update on his fundraising. The story stuck with me because of how the tariff turmoil is impacting him. That’s not something I anticipated for technology companies raising from venture capital firms.

He’s raising a $1 million round and had a lead investor committed for $500k. He was deep in diligence with a few other firms to fill out the rest of the round. Then, the tariff turmoil hit. All the investors in deep diligence simultaneously pulled out. His lead investor has notified him that it will pull out too if the remaining $500k isn’t raised within a tight window.

This founder went from seeing his fundraising go from a clear path to completion to complete uncertainty because tariff and stock market turmoil rattled the investors he was talking to.

This story was surprising to me since this founder is early stage, but it was a reminder. The tariffs and stock market turmoil they caused are prompting uncertainty, which will show up to entrepreneurs in all sorts of unexpected ways.

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Weekly Update: Week 263

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: 58
  • Total blog posts published: 371

This week’s metrics:

  • Books read: 1
  • Blog posts published: 7

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

What I’ll do next week:

  • Read a biography, autobiography, or framework book
  • Create an opportunity solution-tree diagram for this project

Asks:

  • If you can get me an invitation code to Manus, please let me know!
  • 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-three was another week of learning. Looking forward to next week!

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Last Week’s Struggles and Lessons (Week Ending 4/13/25)

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:

  • I struggled to stay focused this week amid all the tariff turmoil.

What I learned:

  • I need to be specific about the skills I’m looking for in a senior engineer.
  • Visually showing how biographies and other books are connected would be valuable to entrepreneurs.
  • Writing blog post series about biographies is a way to both create magnetic luck and connect with entrepreneurs who love to learn.
  • The opportunity solution-tree diagram method detailed in Continuous Discovery Habits is a great way to capture all customer needs, pain points, and desires—and to show all the ways you can satisfy or solve them and to determine which of your ideas are good ones.
  • I need to apply the methods from the above-mentioned book to this project.

Those are my struggles and learnings from the week.

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A Builder’s Cold Email Taught Me a Lot

An engineer recently reached out to me, cold. I wasn’t sure how I got on his radar, so I asked. He’s an avid learner who’s trying to round out his business skills to be a better entrepreneur. He shared that he’d read one of my blog post series about a biography I’d read and decided to reach out to me. This engineer is sharp, so I’m glad we connected.

I thought about that conversation more today, and I have a few takeaways:

  • This engineer has a portfolio of side projects and cool things he’s building. Seeing them made me curious to learn more about them and him. They showed me that he isn’t just a talker. He’s executing, which gave him credibility.
  • Whenever I hear from a reader that my posts helped them, it fires me up. That kind of feedback motivates me.
  • In the last year, every person who reached out after reading my blog mentioned a post about a biography adding value to them and triggering them to reach out. I need to write more in-depth posts about biographies.
  • Sharing my learnings about biographies has led to my meeting smart and interesting entrepreneurs across the country whom I’d never have met otherwise.
  • The posts about biographies are helping me create magnetic luck (see here).
  • Posts about entrepreneur biographies have filtered the type of people who reach out. It’s been entrepreneurs who are serious about reading to learn.
  • I want to connect with more entrepreneurs who get value from my posts about biographies. I need to figure out how to let those readers know I want to hear from them.  
  • I need to turn the old posts about biographies in these posts (and future posts) into a newsletter.
  • Cold outreach works. More people should do it more often (in the right way). There’s zero to lose and lots to gain.

I never would have thought it, but writing about what I’m reading adds value to others and is a good way to connect with entrepreneurs who love to learn (my kind of people).

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Why Startup AI Projects Miss the Mark

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.