The Resilient Entrepreneur, Edition #119
Hi there
I hope you had a great week!
Here are the topics in today's edition:
- Out-of-Office Replies Are Making You Obsolete
- Why Escalation Is Every Entrepreneur’s Worst Move
- Stop Budgeting Like a Consumer. Forecast Like an Entrepreneur
Please reach out with comments, questions, or suggestions for articles!
Talk soon,
Tom
TACTICS FOR RESILIENT ENTREPRENEURS
Out-of-Office Replies Are Making You Obsolete
Out-of-office replies feel harmless. But chain enough of them together and you’ve just killed a deal, a project, or your own career.
Life is unfair sometimes: It often feels like David vs. Goliath. You’re doing whatever you can against an almighty opponent. And the almighty opponents keep the upper hand, even though they are lazy.
As an entrepreneur, Goliath is not always your competitor commanding a large market share. Goliath often hides in time constraints: Stuff takes much longer than you want it to take. Since I co-founded Yonder, a B2B SaaS company, nothing ever moved quickly, and I don’t think it was our fault: RFPs were delayed, scheduled meetings were canceled at the last minute, or “priorities have shifted”.
It’s similar in my life as an active reserve officer in the Swiss Armed Forces. As a battalion commander, I don’t interact just with other active reserve soldiers in my battalion, but also with the military administration. The military administration is the Goliath of any army. In contrast to tactical formations in a 24/7 mission, they live an office-hours life. As a consequence, nothing ever moves quickly when you have to involve the military administration.
Why is the frustration that everything takes so long common to both my roles as an entrepreneur and an active reserve officer?
The Common Root Cause
The root cause of most delays is that people are out of the office all the time: Seminars, training, conferences, vacation, unpaid leave, illness, and long-term medical absences.
In many large organizations — including most of our customers and also the military administration — people don’t read their emails during their absences, not even if those absences are business-related. They just activate an out-of-office reply in their Outlook before they leave. And before they activate the out-of-office reply on Friday afternoon, they fire off a ton of emails. And then they close the laptop and leave everything behind.
Sometimes, they don’t even include an email address to contact in case of urgent issues. Sometimes, they include the contact details of their deputy, whom you can contact during their absence. And in many cases, when writing to that deputy, you get… an out-of-office reply. Because their vacations overlap, or one is on vacation and the other is attending a conference.
Do you still wonder why everything takes much longer than you want it to take?
The Contrast
Now contrast this out-of-office mentality with entrepreneurship.
When an RFP with a tight timeline is floated during your vacation, you will still have to answer it. If you only discover the unread email in your inbox after your return, the deal is dead.
When you’re experiencing an outage or data loss situation on your software platform while attending a conference, you will need to leave the plenary room, find a quiet place to dial into the war room call, and help get this sorted out as quickly as possible.
You can’t leave customer calls unanswered if they repeatedly try to reach you on your mobile phone while you’re away, even if the reason they called is unimportant.
No matter how you look at it, entrepreneurs are always on duty. It’s the same for military officers. No matter if you’re in the trenches or leading an exercise, you cannot just switch off your mobile phone and close your laptop. You’re there to make sure as many of your soldiers make it back unharmed.
What To Do About It
I’m not advocating being always-on for every petty issue. That would be a recipe for burnout. But if you want to advance things, there is only one thing you can do: Don’t let tasks lie around for too long. If you receive an email that needs clarification, reply or ask for a call immediately. Because if you reply with a delay, the recipient might be out of the office again. This is not cynical; it’s a coping strategy in a world of slow and large organizations.
Conclusion
As an entrepreneur or a military commander, you’re responsible for ensuring that your mission is accomplished, no matter what it takes. Even if it frustrates you, even if it’s unfair that those corporate employees warming their chairs have an easy life and are most probably better paid than you are.
Yes, it requires mental strength and frustration tolerance. But there is a silver lining: At some point, the leaders of large organizations will notice that those employees who are always out of the office don’t achieve anything, and they will be declared obsolete much earlier than any entrepreneur or military commander out there.
STRATEGIES FOR RESILIENT ENTREPRENEURS
Why Escalation Is Every Entrepreneur’s Worst Move
Q told Bond always to have an escape plan. For entrepreneurs, the best escape plan is avoiding escalation beyond what can be repaired.
At the end of the James Bond movie “The World Is Not Enough”, James Bond asks Q if he is planning to retire soon.
Q lowers himself into a trapdoor in the floor and delivers his final piece of advice to 007:
“Now, pay attention, 007. I’ve always tried to teach you two things. First, never let them see you bleed. Second, always have an escape plan.”
This article is about having an escape plan, but not quite in the sense that you might imagine. I’m not talking about scenario planning and forecasting, having a plan B, or anything like that.
I’m talking about escalation. Or rather, how to escalate in a way that keeps an escape plan alive.
Geopolitics
Escalation is en vogue in geopolitics these days. Just look at the Iran war. Irrespective of your political position, it’s fair to say that it was easy to start this war, but it will be damn hard to end it. The war was started without having an escape plan, that is, without knowing how to de-escalate. No amount of martial rhetoric on social media or political arm-twisting behind the scenes will get the monster re-chained.
So why on Earth do politicians do such stupid things? Very often, humans do apparently “stupid” things because of biases or prejudices. Or because they get stressed out, or because they are frustrated about a petty detail.
Politicians are humans after all, just like entrepreneurs or parents. That doesn’t justify launching a pointless war, of course, but biases, prejudices, stress, and frustration can catch any human off guard, including every politician.
Entrepreneurship
Let’s leave geopolitics, as most of us have zero influence on it anyway. Instead, let’s turn to entrepreneurship. In a way, entrepreneurs are a bit like politicians: They call the shots. When things go well, everybody says it was the team’s efforts. And when things turn sour, everybody points at the entrepreneurs and calls their decisions “stupid”.
That’s a fact of life, and you can’t change it. However, you can try to avoid the obviously wrong decisions.
Hm, what is an “obviously wrong” decision then? Here are some thoughts from my life as Founder & CEO of Yonder, a B2B SaaS company.
A wrong assumption about a product’s market potential is not an obviously wrong decision. It’s better to start with a wrong assumption, test the waters, and adjust your plan rather than to do nothing.
Bad hiring decisions aren’t obviously wrong decisions. Hiring is difficult and involves lots of gut feeling, which can be flawed. Furthermore, most “bad” hiring decisions only turn out to be bad decisions after some time with your new employee.
A technical decision about software architecture that doesn’t scale infinitely isn’t an obviously wrong decision. Why would you need a scalable architecture before you have hundreds of customers? You can always change and improve the architecture later, leveraging new technologies that weren’t available when you took that original software architecture decision.
Now we discussed three examples of not-obviously-wrong decisions. So, what is obviously wrong then?
I would say 95% of all obviously wrong decisions involve (unnecessary) escalation.
Getting into an argument with your co-founder happens now and then, even in the best founding teams. If both of you are agitated and emotional, don’t add more fuel to the fire. If you feel provoked by your co-founder, don’t retaliate. Maybe he didn’t intend to to provoke you, and even if he provoked you with intent, swallow it. Because if you escalate a situation between co-founders beyond what can be repaired, you’re risking the future of your company. A startup is dead if the co-founders are in serious conflict.
Customers not paying invoices on time is a standard thing nowadays, unfortunately. But if you’re confronted with heavily overdue invoices, don’t start debt collection or a legal case. Don’t interrupt service. Because if you do such things, the customer relationship might get damaged beyond repair. And a startup without customers is dead, too.
Some Homework for Yourself
There would be plenty of other examples, but that’s not the point of this article. How can we build an escape plan into situations that run the danger of escalation?
One approach is to de-escalate when something boils over. Say you’re sorry, ask how you can contribute to get back on a constructive path. It always takes two to fight, and somebody has to step back first. That somebody could be you.
A much better approach is to avoid starting an escalation in the first place. Bite your tongue before replying in a heated discussion. Think twice if the other person really wanted to insult you, or if you just felt insulted (yes, that’s one of the biases I mentioned above). Never say something you cannot roll back.
Yes, that’s hard. It’s especially hard for entrepreneurs who are usually alpha types and used to calling the shots. But give it a try. Develop a sense for situations that could easily escalate, and actively start avoiding unnecessary escalations.
Your true escape plan is when you never need it, because you don’t get yourself into situations that are beyond repair.
STRATEGIES FOR RESILIENT ENTREPRENEURS
Stop Budgeting Like a Consumer. Forecast Like an Entrepreneur
Entrepreneurs run rolling cashflow forecasts to spot trouble years ahead. I applied the same model to private budgeting.
I checked my budgeting app last Sunday morning. It told me I had spent 12% more on groceries than the month before.
Useful. But completely irrelevant to the question I actually needed to answer: can we afford to make an extra mortgage payment in Q3?
No app I tried could answer that. Nor could the spreadsheet I’d been halfheartedly maintaining since 2019 answer this question.
The Problem
Every personal finance tool I know is built around tracking. Those tools all follow the same model: Connect to your bank, categorize your spending, and get a colorful pie chart of where the money went.
To answer the mortgage repayment question, that’s the wrong model.
You’re not trying to figure out where last month’s money went. You’re trying to answer questions like:
- If interest rates rise by 1% at renewal, what does that do to our cash position in 18 months?
- We want to pay off the mortgage 4 years early — can we absorb an extra 800 per month starting in September?
- The roof needs replacing. Does that kill our liquidity, or can we absorb it?
Tracking apps answer none of these. They’re excellent rear-view mirrors and useless windshields.
The Solution
I’m the Founder & CEO of Yonder, a B2B SaaS company. Since incorporation, I have been maintaining a detailed cashflow forecast in Excel. Over time, this tool morphed into a rolling 36-month cashflow forecast.
We can see a cash crunch coming two years out and adjust. We model scenarios before committing to headcount or infrastructure costs.
Three years ago, I rebuilt my household finances with the same approach. The system has three components:
- A dynamic 3-year forecast. Not a static budget, but a living model where every change ripples forward automatically. If my wife gets a raise in March, I see the effect on our liquidity through the next two years in seconds.
- A scenario layer. Mortgage payoff options, income changes, large unplanned expenses — I model them before they happen, not after.
- A 30-minute monthly ritual. Not a weekend project. Enter actuals, check the chart, and adjust one or two assumptions if needed. Done.
I’ve packaged the whole system into a playbook called The Household CFO. It’s the third version of a guide I’ve been publishing since 2023. This edition adds two new chapters: one on mortgage payoff strategies, and one on running household finances as a couple.
What’s included in this playbook?
- A 10-chapter PDF guide covering the full system, from first setup to advanced scenario planning
- The Excel template with 24 tabs, pre-wired formulas, and a dashboard that updates dynamically
The playbook and template are available on Gumroad – get it here!
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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