I was thinking about yesterday’s post (see here) about entrepreneurs completing a daily report card. The more I thought about it, the more I realized that this would be best done with peers. Isolated, you could lose motivation or let it slip through the cracks. But having peers holding you accountable would add a competitive and supportive element to it.

I also think that sharing daily reports could be a great way for entrepreneurs to accelerate their learning. In my report, I have sections for what I did wrong that day, what I did right, and what lessons I learned. If entrepreneurs were to do something similar and then share these daily report cards, peers would be learning from each other’s successes, failures, and lessons.

I need to think more about this and how it would work, but I like the idea of entrepreneurs having daily report card partners.

This week I listened to an entrepreneur describe how he determines whether he had a productive and positive day. He readily admitted that his criteria are subjective and that he isn’t tracking them anywhere. He’s figured this out in more of a hand-wavy, finger-in-the-air reflection over the past couple of weeks. He also described how impactful it is to string together consecutive productive, positive days.

A few weeks ago, I began experimenting with completing daily report cards (see here). I’m still doing them. I’ve had a positive experience, and I’m wondering if my report card (a modified version of the one discussed in my previous post), could be a useful tool for entrepreneurs.

I’m going to think about this more and chat with a few entrepreneurs to see what they think. But my gut tells me yes and that I need to find two or three entrepreneurs willing to experiment with this for a month.

Today I listened to a podcast on which a man who’d had outsized success as an investor was interviewed. One thing he stressed was the need to set deadlines when you’re learning a new skill. If you don’t, learning the skill will take longer than it should.

What this investor was talking about is covered by Parkinson’s law, which says, “Work expands so as to fill the time available for its completion.”

People have a natural tendency to pace themselves based on the time available to complete a task (e.g., learn a new skill). If that window is short, they’ll work really hard. If it’s longer or infinite, they’ll work slowly.

When I’m learning a skill (or doing any task, for that matter), I benefit tremendously from setting a deadline. Putting time constraints on what I’m trying to do forces me to figure out how to work efficiently. When I haven’t had a time-limited goal, it’s taken much longer than it should have.

Parkinson’s law is true and reflects human nature. I’m not immune to it, so I use deadlines as a constraint to avoid being falling into its trap.

I had a debate with an entrepreneur this past weekend about AI and software companies. The question was whether AI will disrupt mission-critical software companies. Think ERP, CRM, and HCM software like NetSuite, HubSpot, Salesforce, Workday, etc.

Having built an ERP system with CRM functionality, my answer is no. In the short to medium term, these software companies will continue to have a strong moat. I believe this for two reasons. First, these systems are very complex and run functions that are mission critical. The risk of replacing one of them with a system that doesn’t work as well is too high, even if the upside is saving money. Disrupted operations can lead to significant financial losses and tarnish a company’s brand. Most companies don’t want to take those kinds of risks (start-ups might, though).

When I was running my company, there was zero chance you could get me to change from the ERP/CRM system we built for ourselves. The risk and learning curve associated with switching were too high. Even if someone had given me the software for free, I would have said “no thanks.”

Cost is the second reason I believe mission-critical companies aren’t about to be disrupted by AI. Having AI build a system as complex as the ones mentioned above would take significant time and energy and cost a ton via tokens. Then there’s maintenance. You can’t just build it and forget about it; you have to maintain homegrown systems, which can require material resources. When a company thinks about the time, energy, and cost required to build and replace a system, they’ll keep what they have and allocate those resources to high-return activities.

My company’s internal software was a living thing. We were always making improvements and changes to it. I learned over the years to budget a certain amount of salary and team bandwidth for maintenance of this software.

Complex, mission-critical software is the backbone of many companies. If one of these systems stops working, a company is flying blind and in some cases can’t operate at all.

As of today, I don’t think these companies are at risk of losing customers. Whether they’ll continue to grow at historical rates is a legitimate question. I think the probability that they will is high, because I doubt that company leaders want to start building these types of systems from scratch. The return on the allocation of resources doesn’t make sense.

The book I’m reading this week is great. It’s a biographical anthology about nine people who achieved outsized success. I won’t spoil it (check the post on Monday for the title), but one of the authors said something that’s stuck with me. After reading tons of books in his field and interviewing the nine people in the book, he realized something:

[T]here is almost always someone achieving enormous success in doing something that you think is impossible.

I agree. If most people think something is impossible, it may be more the case that it’s really hard and tons of people have failed at it. If you’re one of the diligent people who figure it out, the reward could be massive. This is a classic power-law outcome. Only a small fraction of people succeed, but the ones who do receive rewards so large they’re hard to comprehend. Think Steph Curry’s salary of $62 million for the next NBA season (per spotrac) or Jeff Bezos’s $256 billion net worth (per Bloomberg as of this writing).

Hard things are . . . well . . . hard. That doesn’t make them impossible. Many hard things seem impossible but are actually quite possible if effort is applied to solving or mastering them over a long period of time. Bezos and Curry spent decades working at and perfecting their crafts. In the early years, they weren’t sure they’d succeed, but they knew their chances of success would continue to go up as they worked at it consistently. Each has achieved what, 20 years ago, many would have said is impossible. In reality, it wasn’t impossible; it was just really hard and required a ton of energy and commitment over a long period of time to make it happen.

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This past weekend, I created a flowchart with swim lanes to dissect what went wrong in a critical situation at a friend’s company. The details are complex, but one thing stood out to me. The more parties that stand between you and what’s happening with your customer or your product, the harder it becomes to understand the issue and quickly resolve it.

I had a loose idea of what happened based on a long email chain, but it wasn’t crystal clear and I wasn’t familiar with all the nuances. Creating the diagram this weekend helped me a ton. I was able to get my head around the situation by visualizing who did what. That helped me identify the parties that likely caused the issue and where and when in this complicated process everything transpired.

I now have a good idea of what needs to happen to prevent a repeat of this problem in my friend’s company. This exercise took longer than I expected, but the output was worthwhile. It’s definitely something I’ll keep in my toolkit.

As I shared two days ago (see here), I’m helping my friend’s start-up. He created his own brand and products for it, and he’s manufacturing, warehousing, and shipping them to customers. I’ve been trying to help him resolve some logistics challenges. Here are our insights so far:

• Partners – International manufacturing and logistics partners are important, especially when things don’t go as planned, so it’s important to choose reliable, communicative ones.
• Network distance – The more network distance there is (that is, the more companies there are) between you and a shipment, the longer it takes and the harder it is to resolve problems.
• Cross border – Language and cultural differences can affect how fast problems are solved.

It’s still early and I’m sure I’ll learn more, but those are the lessons so far.

I’m helping a friend with his start-up. He’s created his own brand and products for it. He sells the product directly to consumers online. Because he’s selling his own branded products, he has to manufacture them, warehouse them, and then ship them to customers.

It’s early in his company’s journey, and his product and marketing strategy are great. However, the logistics of moving products between different countries and fulfillment centers and to customers’ doorsteps haven’t been smooth.

When people buy a product, they underestimate how much is involved in going from an idea to a physical product in their hand. Their minds would be blown if knew what was happening behind the scenes, including the number of people who touch the product and the number of times it must be moved.

Creating a branded product is hard. If you’re an entrepreneur considering that path, like it or not, logistics know-how will be a factor in what makes or breaks you (you can choose how much of it is internal vs. outsourced, though).

As I shared last month (see here), I’ve been working with Atlanta entrepreneurs and moderating an accountability group. The group meets once a month for a few hours. I’m aiming for the group to be highly engaged and open to sharing so they’ll learn from peers' experiences and can solve their own problems faster. My goal is to make each meeting a better experience for the entrepreneurs than the last.

We had our second meeting this week. The members rated the meeting highly (this is at the end of each agenda), but the meeting didn’t meet my expectations. “High engagement” means everyone is showing up, being prepared to share, and learning from their peers. During our first meeting, we had 100% attendance. I also had everyone go through their calendar month by month for the next six months. We found dates that worked for everyone and committed to those dates as a group. I sent meeting invites out for the next six months. Stuff happens, but as much as possible, I wanted to mitigate scheduling issues that would prevent a busy, type-A entrepreneur from attending.

This month, two members couldn’t make it. Another member was late. I’ve realized that I didn’t fully set expectations with the group. The expectation related to being late had been set (no admittance after the meeting starts), but I hadn’t crystallized what happens if someone misses a meeting (whether that’s planned or because of tardiness).

My thinking is that A players want to be around other A players. They get annoyed when they’re forced to work alongside less-than-A players and often remove themselves from such situations. I think everyone in this group is an A player, but this week, not everyone gave A-level effort. Three members missed. To maintain the high-engagement, high-effort culture required to make this group a success, I need everyone to give A-level effort every meeting. That means showing up on time and prepared.

Last month, everyone gave A-level effort. The challenge this month is that some members gave A-level effort and others didn’t. I’m pretty sure (though this is an assumption; no one said anything to me) that attendees who did give A-level effort noticed the difference. I need to address this and have the members who missed demonstrate to their peers that they can and will put forth A-level effort going forward.

I’m not 100% sure how I’ll do this, but I’m thinking about having each member who missed explain, in two minutes, why they want to continue being part of the group and what they’ll do to avoid missing future meetings. The members can then vote on whether that person can continue as a member (i.e., do we think this person will give A-level effort going forward?).

Regardless, the second meeting is in the books, and the members got value from it. I’m looking forward to tweaking this format to make the rest of the meetings better than the first two.

I recently caught up with a founder who’s had a rough few months. Money has been tight, and fundraising hasn’t been going so well. The company was down to less than a month’s worth of cash, and it has been operating like this for several months. The founder was forced to keep the company afloat using his personal savings. He was stressed. But he managed to stay alive and keep pitching investors.

This month, he received the largest single check the company has received from any investor since it was founded a few years ago. The $500,000 check was from an angel investor, an entrepreneur who sold his company and believes in this founder’s vision.

Just like that, the fortunes of the company have changed and the founder’s funding worries are over, at least for now.

This story is a reminder of two things: luck plays a bigger role in success than many people realize, and there’s something to staying alive long enough to get your lucky break.