I Wasted 6 Months in 2025 (Part 1: The Planning Mistakes)
Here are the 4 planning mistakes that cost me time, money, and momentum
Happy new year, and welcome back to Buyout Diary.
I wasted six months in 2025 doing things wrong. These mistakes cost me time, money, and momentum. Some were subtle, the kind you don’t notice until months later when you realise you’ve been building on the wrong foundation. Others were obvious in hindsight, the kind that make you wonder how you missed something so fundamental.
I made seven major mistakes in my first year as a European searcher, and I’m sharing them because I want you to learn from mine rather than making the same ones yourself. We cannot just copy the American approach here in Europe because we have a different market, different culture, different timelines. These aren’t just my mistakes either. They’re common patterns I see across European searchers, and I’m sharing them openly so you can recognise them faster than I did.
This is Part 1, covering the four strategic and planning mistakes I made before I even started seriously looking at deals. Next week, I’ll share Part 2 with the three execution mistakes that cost me the most time.
Mistake #1: Searching Without a Plan
This was my first and perhaps biggest mistake. I was excited about ETA, about acquisition entrepreneurship, about the whole concept of buying and building businesses. When you see something new and exciting, you want to dive straight in and start immediately. I wanted to go deep, find a business, and buy it. But I wasn’t clear about what I was actually searching for. I thought any business that looked nice and could make money would be fine, but that’s not the right way to approach this.
I started searching without a clear private placement memorandum or investment thesis, and this turned out to be a critical error. Why was this a mistake? Because I evaluated everything, but nothing had a filter. I wasted time on deals that never fit my criteria, on deep sourcing exercises for businesses that didn’t match my skills or my vision. I was essentially wandering through opportunities without any framework to guide my decisions.
The transformation came when I finally sat down and wrote my investment thesis. Everything became clear. I suddenly knew what I was looking for, what to say yes to, what to say no to, and why. The clarity was immediate and powerful. Instead of evaluating every opportunity that came my way, I could quickly filter based on my criteria. Instead of spending days analysing businesses that would never work for me, I could focus my energy on opportunities that genuinely fitted my vision.
What should European searchers do? Write your private placement memorandum or investment thesis before you start looking at deals. This isn’t optional, it’s foundational. Your investment thesis should define what you’re looking for, why you’re looking for it, what your selection criteria are, and what success looks like for you. It should be specific enough to guide decisions, but flexible enough to evolve as you learn more about the market and yourself.
Mistake #2: Not Being Clear About AI-Resistant and Recession-Resistant Criteria
This mistake is particularly relevant in 2025 and 2026 because we really need to think about these two things: AI resistance and recession resistance. I looked at businesses without thinking about long-term resilience, which was frankly stupid. I was excited about different sectors like accounting, software businesses, graphic design, and I didn’t stop to think about what would happen when AI inevitably disrupted these industries.
Why does this matter in 2026? Because AI is changing everything, and economic cycles happen whether we like it or not. What happened to me? I spent time evaluating businesses that could be easily disrupted or automated. Accounting, for example, where bookkeeping and basic financial services can increasingly be done by AI. Graphic design, where AI tools are becoming remarkably capable. These businesses might work today, but what about in five or ten years? What happens to the valuation when AI can do sixty percent of the work? What happens to your customer base when they discover they can get similar results for a fraction of the price?
The transformation came when I added AI resistance and recession resistance as core criteria in my search. My focus on businesses became much sharper. I could quickly filter out opportunities that didn’t meet these standards. But more importantly, I developed a framework for thinking about resilience that I could apply to any industry.
Here’s how I think about AI resistance now:
Can this business be easily replicated by software or AI?
Does it require human judgment, physical presence, or relationship-building that machines can’t replicate?
Is the core value proposition based on trust and personal connection rather than just technical skill?
Does it serve fundamental human needs that won’t disappear regardless of technological advancement?
And for recession resistance:
Do people need this service even when times are hard?
Is this a discretionary purchase or a necessity?
Does demand stay relatively stable across economic cycles?
Are customers locked in through habit, necessity, or high switching costs?
When I applied this framework, certain industries became obviously attractive: craftsmanship like plumbing, electrical work, carpentry, because you can’t automate a broken pipe in someone’s home. Local services that require physical presence and trust-based relationships. Machine shops that do custom manufacturing work requiring human expertise and problem-solving. Even things like luggage storage in big-city centres, which serve a fundamental need for travellers and can’t be automated away.
What should European searchers do? Define what AI-resistant and recession-resistant means for your specific search. Add this to your investment thesis and selection criteria. Think carefully about which businesses are genuinely protected from these forces. Don’t just assume a business is safe because it’s always been done a certain way. Technology changes industries faster than we expect, and economic cycles are inevitable. Build these filters into your thinking from day one.
Mistake #3: Not Choosing Your Region (Culture Fit)
I didn’t think hard enough about geography and culture fit early on. I took a scatter-gun approach, thinking, “how about all of Europe? Why not?” I’m German and I speak German. I live in the Netherlands and I speak Dutch. I speak English and studied in England. I thought I could do Belgium, Denmark, Austria, wherever opportunities appeared. But honestly, I don’t know all these countries one hundred percent.
The countries I genuinely know are Germany and the Netherlands. I grew up in one, and I’m living in the other. I speak both languages fluently, I understand the cultures, I know how business is done, I know what sellers care about. This is where I have fit. Everything else is surface-level understanding, the kind of knowledge you get from visiting or working briefly, but not from living and breathing a place.
You need to understand the local market, culture, and language of wherever you’re searching. This isn’t just about speaking the language well enough to negotiate a deal. It’s about understanding unspoken rules, cultural expectations, how decisions are made, what matters to people, what sellers worry about when they’re thinking about succession. It’s about knowing whether a handshake still means something in this market, or whether everything needs to be in writing. It’s about understanding regional pride, local business practices, and the thousand small things that make-or-break relationships.
What happened when I ignored this? I looked at opportunities that were too far away or culturally difficult. I considered businesses in Belgium, the UK, Austria, places where I didn’t have deep cultural understanding. This was a waste of time and energy. The conversations were harder, the trust-building took longer, and I could never quite get past the sense that I was an outsider trying to understand an insider’s world.
The transformation came when I focused on Amsterdam and my local area. Everything changed. The deals became more real, the conversations more substantive, the relationships more authentic. Sellers could see I understood their world. I could pick up on subtle signals that I would have missed in another culture. The due diligence was easier because I knew what questions to ask and what answers meant. Even simple things like understanding local regulations, tax structures, and business norms became advantages rather than barriers.
What should European searchers do? Pick your region based on where you want to live and where you understand the culture deeply. This needs to be written into your thesis. I see many searchers picking the wrong area, like Germany because it’s the biggest economy in Europe, even though they don’t speak German and have never lived there. The hidden champions, the Mittelstand companies, they’re not all in Berlin or Munich. They’re spread across the country in different regions with different cultures and different business practices.
You cannot manage a German business from Amsterdam if it’s somewhere like Flensburg near the Danish border. The sellers will want you there as the owner, living in their community, understanding their world, becoming part of the local business ecosystem. If you can’t or won’t do that, you’re not the right buyer for that business, regardless of how good the deal looks at paper.
Think about this carefully and write it into your investment thesis. Geography and culture fit matter more than you think. They affect everything from deal sourcing to due diligence to post-acquisition success. Get this right at the start, and you’ll save yourself months of wasted effort.
Mistake #4: Thinking You Had to Choose One Industry Immediately
I felt enormous pressure to pick one industry from day one. I thought this was what serious searchers did. They picked their industry, built expertise, and focused relentlessly. So I started wandering between industries: digital businesses, then accounting, then retail, then maritime, then agriculture, then logistics, then craftsmanship. At the time, this felt like failure. I thought I was being indecisive, that I couldn’t commit, that I was wasting time whilst other searchers were already deep into due diligence on their perfect target.
The transformation came when I realised this wasn’t wandering at all. It was research. Each pivot taught me something important about what I was looking for, what I was good at, what excited me, and what didn’t. I needed to check which industries actually fitted my experience, my knowledge, and my interests. More importantly, I needed to understand which industries met my AI-resistance and recession-resistance criteria, which ones had the kind of businesses I could actually afford, and which ones had sellers who valued what I could bring beyond just capital.
Looking at digital businesses taught me I would rather not compete with venture capital and wasn’t excited about the constant technology refresh cycle. Exploring accounting firms showed me that AI disruption risk was real and immediate. Retail revealed that most businesses in this space were either too small to be viable or too dependent on founder relationships that couldn’t be replicated. Maritime was interesting but too capital-intensive and too far outside my expertise. Agriculture and logistics taught me about supply chain complexity and the importance of physical assets. Each of these pivots added to my understanding, even though I didn’t buy any of these businesses.
By the time I focused on craftsmanship and local services, I knew why I was choosing them. Not because someone told me they were good industries, but because I’d systematically explored alternatives and understood what made these businesses attractive. They were AI-resistant, recession-resistant, affordable, locally rooted, relationship-based, and aligned with my skills and interests. That conviction came from exploration, not from picking something on day one and forcing myself to stick with it.
What should European searchers do? Give yourself permission to explore, but do it with intention. Each pivot should teach you something, not just be random movement. You’re not failing if you look at multiple industries early in your search. You’re gathering data, building pattern recognition, and developing conviction about what you actually want to buy. The key is intentional exploration. Look at different industries with a learning mindset, extract the lessons from each one, and gradually narrow your focus based on what you discover about yourself and the market. Document what you learn from each industry you explore, so the time isn’t wasted even if you don’t buy in that sector.
But here’s the important caveat: this exploration phase should be time-boxed. Allow yourself three to six months to explore industries, not eighteen months. At some point, you need to commit to a focus area even if you’re not one hundred percent certain because conviction often comes from commitment rather than from endless analysis. The goal isn’t perfect clarity before you start, it’s enough clarity to begin and the discipline to keep learning as you go.
I Need Your Help to Shape 2026
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Seriously, stop reading and take the survey. I’ll wait. Your input shapes everything I create this year.
Coming Next Week
In Part 2 of this series, I’ll share the three execution mistakes that cost me the most time in 2025. These are the mistakes I made after I started searching, the relationship and timing mistakes that I only recognised months into the process. If the strategic mistakes in this newsletter cost me clarity, the execution mistakes cost me momentum.
I’ll also share a deeper reflection on where I am now with the fund question I mentioned in my last newsletter. The deadline I set for myself is the end of February, and I want to walk you through the thinking process as I work towards that decision.
Closing
Thank you for reading my newsletter. Part 2 comes next week with Mistakes 5, 6, and 7. Until then, keep building, not flipping. Keep focusing on succession, not extraction.
Reply to this email and tell me which of these four mistakes resonated most with you.
Which one did you recognise in your own journey?
Which one are you working on right now?
I read every reply and I learn from your experiences just as you’re learning from mine.
Until next Monday,
Alexander