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Why I Needed Brutal Accountability to Level Up

Years ago, when I was an early-stage founder, I was basically on an island. I was a solo founder and didn’t know many other founders. I was grinding away by myself with no one to talk to about what I was going through. Fast forward a few years and I was in EO, doing several million dollars in revenue.

One of the things that accelerated my progress the most was simple: accountability. Every month, I met with peers and presented my metrics. Good, bad, or ugly, I had to share what happened, why it happened, and what I planned to do the next month. My peers asked me pointed questions that highlighted blind spots, perspectives I hadn’t considered, or mistakes I’d made. It wasn’t always comfortable, but those sessions were invaluable and changed my trajectory as an entrepreneur and that of my company.

My lesson learned from all this was that when I’m trying to do hard things, accountability and pointed feedback (or questioning) from peers help me tremendously. That process forces me to face things I don’t want to face and to level up. It often puts me outside my comfort zone, but that feeling usually means I’m growing, as I want to be doing.

Small Audience, Big Money: The Niche Entrepreneur

Today, I learned about two entrepreneurs who have built interesting (separate) businesses based on their passion. They create 30-second to 1-minute videos in which they review board games and card games, explain how to play them, and record themselves playing them.

The interesting thing is their revenue model. These entrepreneurs each have millions of followers across various social media platforms. Their followers, I assume, are interested in finding out about new games. With a reach to consumers with a high interest in games, these entrepreneurs have become vital to companies looking for exposure for their games. They charge these companies up to $15,000 for a single post. And they create three to five posts per week. You do the math.

Whatever you’re into, other people are into it too. Your interest may seem niche, but the internet allows you to connect with enough people to turn a niche interest into a large business. These two entrepreneurs have built audiences who have the same interests they do and, in turn, created businesses around charging companies who want to access and market to those “niche” audiences.

The Accounting Book Every Investor Actually Needs

I was having a chat last week with someone who invests in public markets. I was curious how he approaches valuing the companies he invests in and determining how strong they are financially. During our conversation, I realized that he doesn’t understand accounting or the financial statements of the companies he invests in. He could recite metrics like net profit, revenue, and debt, but he didn’t really understand how they work together and the picture they paint of a company’s financial health and trajectory. For example, he didn’t understand how a company could have negative net profit (i.e., negative GAAP net income) and still be generating a large amount of cash (i.e., have positive free cash flow).

I was fortunate to have taken accounting classes in college, and I applied those learnings as the CEO of my company. But for people who don’t want to be entrepreneurs and haven’t taken accounting classes, I want to discover whether there’s a book or something else that can help them understand the accounting basics applicable to public companies.

That’s my goal. I found a few books. I’ll read them and share the ones I think are useful for public-market investors.

AI Makes Building Easy. Distribution Decides Winners.

I listened to a podcast recently in which a founder said something that stuck with me. Building a software or digital product is easier than ever. With AI tools, you can build with a fraction of the engineering team you needed 5 or 10 years ago. Or you can have AI write your code for you. Therefore, he thinks that distribution is the most important thing now. How you reach and convince potential customers to buy is the most important thing, or so he thinks.

I partially agree with this, but I’d add something else: Because everyone can build products faster, better products will have an edge and resonate more with customers. To build a better product, you must understand the problem deeply so you can solve it better than the competition can. Deeply understanding the need of the customer is vital.

If you have a superior understanding of the problem and have built a superior product, then capturing attention is critical. Capturing someone’s attention is harder than ever these days, given the amount of content and the number of ads the typical person sees in a day. Entrepreneurs who know how to get in front of the right people with a message that resonates will have a huge advantage.

Overall, I think the entrepreneurs who do well going forward will have a deep understanding of the customer’s problem and how to best solve it, be able to communicate the problem and how to best solve it concisely, and know how to distribute their solution in a creative and cost-effective way.

The Unexpected Effect of a Decision Journal

Today I was looking at my decision journal and the post I wrote about it (see here). Just looking at the journal made me see a recent decision more rationally. It was a small decision, not worthy of being recorded in my journal. But thinking about how I would describe it if I did write about it in the journal helped me think about it more clearly and quickly conclude it wasn’t the greatest decision.

I think that knowing I have a decision journal forces my brain to think more rationally. I guess physically seeing the journal may activate certain frameworks around decision-making. Not totally sure of this yet, but something I’m definitely watching.

Cash Crunches Can Spark Your Startup’s Best Ideas

This week, I had a long conversation with a founder. He’s been building his start-up for several years, and he relies on government grants for a large part of his operating budget. He’s getting paying customers too, but not enough of them that he can rely solely on that revenue to fund his operations. He has a multiyear grant from the federal government, but those funds can’t be disbursed to him until a certain act that allows a particular agency to disburse funds is passed. The founder was banking on that money to fund 2026, but he hasn’t received the funds yet and won’t until the legislation passes. He’s in a tough spot. He has about 30 days’ worth of cash left. After that, he’ll have to start reducing expenses and headcount.

This isn’t great, but it’s not unheard of for entrepreneurs. Being short on cash, for whatever reason, happens a lot. I’d argue it’s more the norm than the exception. While the times we’re living through can be stressful for founders and their teams, opportunities exist. When everyone knows that the survival of the company (and their job) is on the line, they get laser-focused. People quickly buy into any changes that align with survival and put their all into making them successful. Alternatively, these moments force founders to think about sources of capital from perspectives they hadn’t considered before. Said differently, the crisis forces founders to think creatively about how they can fund their business. I know founders who, faced with cash crunches, launched new products and services that became so successful that they generated most of the company's revenue.

Being short on cash is no fun when you’re an entrepreneur, but when it happens, consider how you can use the situation to think creatively and get your team focused on what matters most.

Zara Founder’s $3.7 Billion Dividend Lesson

Today, I read a Bloomberg article about Inditex SA (see here) that interested me. Inditex, which owns retailers, including fast-fashion juggernaut Zara, was founded by Amancio Ortega sixty years ago. The company is publicly traded, but he owns more than 59% of its shares, according to the article. Ortega is the fifteenth-wealthiest person in the world, according to the Bloomberg Billionaires Index, and has a net worth of around $126 billion as of this writing.

The article I read caught my attention because of the dividend Inditex is about to pay to shareholders, including Ortega. Based on the number of shares he owns, Ortega will receive $3.7 billion. I assume the dividend is based on the prior year’s financial results.

This article highlights that selling your company isn’t the only way to generate cash, even outsize wealth, for yourself. If you build an amazing company that generates a ton of cash, you can maintain your ownership in it, which increases your wealth, and receive dividends (or distributions) from it, which provides cash flow that you can use to pay living expenses or invest in other assets.

Building to sell is popular, but building to hold forever is how many of the world’s wealthiest people created their wealth.

The Interview Question That Instantly Reveals Curiosity

I was listening to a founder describe his hiring process. One of the things he looks for is people who are naturally curious and learn about new things in their free time. I thought this was a great trait to look for in team members (or people in general), but I wasn’t sure how you identify it in an interview. Then he shared what he calls his most important interview question: “What’s the last Wikipedia rabbit hole you went down?”

I instantly thought about the last thing I researched, and sure enough, Wikipedia was part of it. Because of AI, this might change a bit, but I think this is a great question to quickly gauge someone’s level of natural curiosity and how motivated they are to satisfy it.

Who Speaks for the Customer at Big Box?

A friend started a new company. It’s not a tech company; he makes physical products to sell to consumers. The products are traditionally sold through big box retailers as the main method of distribution (think Walmart or Target). This poses an interesting problem because consumers don’t interact with my friend’s company. The big box retailers sell tons of stuff, and they aren’t going to spend time trying to understand or get insights from their customers who buy my friend’s products. They’ll share information like sales metrics, and if my friend’s products aren’t selling they’ll tell him that, but they won’t be able to tell him why.

My friend recognizes that not being connected to the end consumer will be an issue. He wants his finger on the pulse of his customers so he can adjust as needed to keep his products relevant to them. Otherwise, their tastes could change, and he wouldn’t know it until his sales at big box retailers decline materially. Even then, he wouldn’t know why.

So, he’s considering adding someone to his team whose entire job is to be the voice of the customer. They’d be responsible for staying in touch with end users of the products, gleaning insights from them, and translating those insights into data that their team can use to make decisions.

I’ve heard of voice-of-the-customer-type roles in software and tech, which I think is much easier to accomplish. There’s often a direct relationship with customers because they’re buying from your website. And there are plenty of tools that help you gauge how customers are using (or failing to use) your products. But I’ve never considered how you keep a finger on the pulse of customers who buy physical products through retailers like Walmart.

I’m really curious about this and can’t wait to see how this plays out for my friend. I think he’s on the right track with his voice-of-the-customer role.

Why Stack Ranking Raises Everyone’s Game

When I was in college, I took a course that was 100% based on group presentations. The goal of the class was to turn people into better team members. The idea was that if you work better in a team, your chances of success in most careers rise. But one thing they had to solve was helping people understand where they stood. Am I a good team member and just need to stay the course? Or am I a not-so-great team member who needs to make serious changes?

Their solution: stack ranking.

At the end of each project, every team member had to rate the rest of their team. The catch was that we had to order group members from best to worst. Each person submitted something that looked like this:

  1. Sue
  2. John
  3. Bob
  4. Mary
  5. Tim

Sue got the most points, and Tim got the fewest. After several projects, you began to see a pattern. If you were consistently ranking low, you had to look in the mirror and ask yourself why your peers were consistently giving you low ratings. Your class grade was heavily dependent on your overall ranking at the end of the semester.

That experience was eye-opening. It showed me the power of group members stack ranking each other. Getting a low rating from a teacher was different than getting one from your peers, with all your peers seeing it. The latter felt much worse, partly because it was public but mostly because it came from peers, not an authority figure. No one wants their peers to think less of them. So, what happened was that the stack ranking caused people who weren’t great team members to change their behavior and try to become better team members.

The stack ranking also fostered a competitive dynamic that elevated the effort of the entire class. There could be only one person in the top spot, so everyone dialed it up a notch, hoping to become #1. Ranking highest was a direct result of your ability to be a better team member than everyone else. If someone was ahead of you, you had to try harder. The other person would then try harder too, hoping to hang on to their position. The result was a bar that was continually being raised by group members.

I’m a fan of stack ranking and publicly displaying the results in group settings. It’s a great way to raise the quality of the group effort, and it gives members feedback that’s hard to ignore.