The Resilient Entrepreneur, Edition #129
Hi there
I hope you had a great week!
Here are the topics in today's edition:
- AI or Not AI? Sometimes You’re Faster Without It
- The Month-End Closing Checklist: Boring, but Effective
Please reach out with comments, questions, or suggestions for articles!
Talk soon,
Tom
TACTICS FOR RESILIENT ENTREPRENEURS
AI or Not AI? Sometimes You’re Faster Without It
Everyone promises you can automate your business with AI and chill at the grill. Well, automation and AI don’t always pay off.
These are the 10 ultimate AI tools to automate your business.
Here are the 5 SaaS tools every entrepreneur needs.
How to build a 1 million ARR business without a team.
We’ve all read such headlines. The internet is full of them, and they carry a disturbing promise: Chill at the grill while your business works for itself, and your only job is to collect the profits.
Sorry to be direct, but this won’t work. I know from experience; I’ve been an entrepreneur for more than 10+ years. Back in 2015, I joined an existing company as employee #20, and a few years later, I founded Yonder, a B2B SaaS company, and built it from scratch. Neither experience involved any chilling at the grill, and profits were always hard-earned.
Now you might argue that those experiences were before the age of Artificial Intelligence, and that many of my tasks from back then could now be automated easily. And that’s exactly the topic we’ll dive deeper into in this article.
Automation: Effort vs. Benefit
Don’t get me wrong; automation is great. But, like every question in entrepreneurship, it’s about balancing effort and benefit. Is it worth automating a complex, error-prone routine that takes you 30 minutes every week? Probably yes. On the other hand, should you spend 5 hours building an automation that saves you 2 minutes per week? I doubt it.
Let’s go back to the chill at the grill analogy to assess whether automation makes sense. Do you prefer to spend 5 hours on a Friday night at the computer automating a petty task, or would you rather enjoy the evening with your spouse, your family, or your friends chilling at the grill and do those 2 minutes of work manually every week?
My choice is clear.
The Ticking Time Bomb: Token Costs
When people think of automation, they usually think about AI tools such as Claude Cowork. That’s certainly one option, but it has a couple of drawbacks: First, AI tools never provide quite the same answer for two runs of an identical task. And that’s what you would expect for many automation tasks. That’s why I still think tools like Microsoft Power Automate or n8n are more useful to automate everyday tasks than any AI tool. But building your Power Automate or n8n workflows with the help of the AI tool of your choice is a great strategy.
There is a second problem with AI tools that many people aren’t aware of. With the introduction of Mythos and Faible, Anthropic moved their frontier models out of their existing subscriptions into a pure pay-per-token model. That’s an unmistakable sign that the days of the cheap AI subscriptions are counted.
What will happen to your AI automations when all your AI subscriptions move to pay-per-token models? For sure, they will still work. But they will suddenly cost orders of magnitude more than that 20$-per-month Claude or ChatGPT subscription. And the more you run them, the more tokens they consume, and the more they cost. So maybe you need to think about doing that work yourself again instead of believing you can chill at the grill and wait for the profits to roll in.
Do You Need Everything on Autopilot?
Finally, let’s ask ourselves a more fundamental question. Do we need everything on autopilot, constantly running and accessible from our phones?
I argue that for many tasks and activities, we don’t need full autopilot and access to our business from our phones. As usual, automation isn’t the silver bullet everybody claims. Some tasks can be done once a week or once a month. For many of those end-of-week or end-of-month activities, I do something that might sound a little outdated for a tech entrepreneur: I depend on Excel sheets and manual work.
And when I’m done with that work, I’ll go and enjoy an ice-cold beer at the grill.
STRATEGIES FOR RESILIENT ENTREPRENEURS
The Month-End Closing Checklist: Boring, but Effective
Many month-end checklist tasks could be automated, but not this one: Thinking of what the changes since last month mean for your business.
It’s this time of the month again: Month-end closing! No entrepreneur likes the admin work involved with month-end closing, but you can’t escape it.
Surely, you can automate it?
Well, think twice. Most month-end closing tasks take 2 minutes per month, and automating them would probably take 5 hours per task.
There is a better way that involves an Excel list and some manual work. What might sound horribly old-school and inefficient is actually the best way to avoid chaos and hectic down the road: If you keep your business in order at the end of every month, you won’t struggle to find your bank documents for your finance audit. You will notice accounting errors at the end of the month they occurred, not one day before presenting your annual results to your board. You will never be surprised by expiring contracts or higher-than-anticipated cloud costs.
Let’s get specific. Here is an overview of my month-end closing list I use at Yonder, the B2B SaaS company I co-founded.
1. Finance Checklist
The most important month-end closing tasks are finance-related:
- Accounts Receivable: First, I check whether we have sent all due invoices to our customers. Sending invoices is the first step towards a positive cash flow, and many entrepreneurs “forget” to send customer invoices on time. That’s cash thrown out the window. Once all customer invoices are sent, I check for any overdue customer invoices. Unfortunately, payment morale has declined in recent years, so chasing money from customers is a constant task.
- Payroll: This one is pretty obvious. You have to run your payroll on time, or your team will soon lose trust in your financial situation. But payroll goes beyond wiring the money — settle social security, file the documents, etc. If you do this only once a year, it will be much more work than if you do it monthly.
- Foreign Exchange Rates: Foreign exchange rates change, and if you’re doing business internationally, this will affect your bottom line. If you have an imbalance of revenue and costs in a certain foreign currency and the exchange rate fluctuates, you might make or lose money. Updating foreign exchange rates manually takes 2 minutes, and it could be easily automated. However, every time I manually update the foreign exchange rates, I also spend a few seconds thinking about what it means for our business. I doubt you could automate this task, too.
- Accounting: Of course, you have to bring your accounts up to date at the end of the month: Accruals, cross-checks, etc. If you do this thoroughly every month, you will have two benefits in one: First, you get a good gut feeling for your company’s financial situation. And second, you will discover accounting errors before they propagate.
- Cash Flow Management: Accounting gives you a rear-mirror view of your finances, but what you really need is a forward-looking forecast. Updating your cash flow plan at the end of every month improves forecast accuracy and helps avoid surprises.
- Investor Reporting: Last but not least, you need to inform your investors about the company’s progress and setbacks. The investor reporting is a condensation of all the financial month-end closing tasks described above. Regularly informing your investors about positive and negative developments builds trust, and you never know when you’ll need that trust.
2. Admin Checklist
Month-end closing is not just finance-related: There are a few other tasks worth doing every month.
- Absence tracking: I ask all our employees to report their absences once a month — holidays, sickness, military duty, mourning, etc. What might sound like overkill for a team of 20 is, unfortunately, necessary. I had to fire a co-founder who cheated on holiday allowance and sickness days. If you document all the absences every month, your life will be much easier if you run into an issue like this.
- Expiring contracts: Once a month, I check all customer and supplier contracts for their expiry and termination dates. This helps me avoid being caught by a contract expiry or missing a termination deadline to renegotiate an existing contract.
- Updating internal processes: If you’re ISO 9001 certified, you need to demonstrate ongoing updates to your internal processes. If you update your processes one day before your recertification audit, your auditor will notice, because your team doesn’t know the valid processes. If you do this continuously, it’s less work, and your team has time to adapt to new processes before the audit. The same goes for updating your risk list, which is also part of your ISO 9001 certification.
3. IT Checklist
And last but not least, there is IT. If you’re ISO 27001 certified, you need to demonstrate ongoing improvement of your information security management system. Here is what I do at the end of each month:
- Backups: Yes, it’s old-school to back up cloud tool data to a local hard drive. I do it anyway — you never know. It doesn’t take much time, but the benefits can be huge in case one of your key cloud providers goes belly-up.
- Cloud Costs: I manually track our cloud costs every month. This helps me to spot anomalies in resource consumption and avoid surprises down the road. Again, tracking costs can be automated, but the thinking of what cost changes mean cannot be automated.
- Vulnerability Reports: The internet is full of dangers, and those dangers change all the time. Running an automated vulnerability report once a month helps us spot all the packages and components of our SaaS application that need updating. Scanning is automated; assessing the risks and prioritizing the fixes is not.
Conclusion
Does it take lots of time to work through this month-end closing list? And is it fun to do so? No, and no; it’s not time-consuming, and it’s not fun. But it’s necessary.
And it takes much less time to do those tasks every month than automating them and running into surprises: You can automate the work, but not the thinking of what the changes since last month mean for your business.
About Me
I’m a tech entrepreneur, active reserve officer, and father of three — writing about entrepreneurship, leadership, and crisis management from hard-won experience. No AI, no fluff, no promos. Just plain-text insights for people building and leading under pressure.
When I’m not solving problems, I find clarity in the mountains around Zermatt.
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