Are you building a business that’s doomed to fail

6am. Cologne, Germany airport.

I’m sitting in seat 14c with a small baby on my lap, nervously waiting for the plane to take off.

They just said it’s a 60 minute delay.

I'd just spent my first Christmas as a dad. A week with my parents in ice cold Germany, watching them hold their grandchild, eating way too many buttery homemade biscuits.

It was wholesome, but now it was hell.

I’m watching a guy in an orange vest scrape ice off the wing with what looked like a giant spatula.

The pilot came on the speaker with a heavy Greek accent. Bad weather conditions, extra safety protocols, de-icing procedures, engine checks.

I saw the ground crew circle the plane. Checking things and writing on clipboards.

Three people, taking their time, while 180 annoyed passengers waited.

And I started to think about how many things have to go right for a plane to not fall out of the sky. Hundreds of checks. Every single one matters.

Skip one, people may die.

I had planned to use the flight to think about the software business I'm starting to build.

In business, you don't literally die when you skip the safety checklist and crash your business.

But you pay with something almost as precious:

Your time.

You can waste years of your life building something that falls out of the sky (or worse, never takes off).

Skipped nights with friends.

Turning down holidays.

Missing out on date nights.

It’s all worth it when it works. But when it doesn’t?

Hell.

I've paid that price a few times now.

I chased ideas that no one wanted, I went for markets that were drier than the Gobi desert and chased customer who never had a dollar to spend.

I'm in the trenches of finding the next business right now. This time I’m gonna be smarter.

So I sat and wrote a 7 step step ‘pre-flight checklist’ to help you guarantee you build a business that soars off into the sky.

Don’t look for big players, look for Bootstrappers

Before I get into a market, I look at who's already making money.

If I only see a16z funded companies with a billion dollar bankroll, that's a red flag. 

They can run at a loss for years. Outspend you on marketing. Undercut you on price just to grab market share. 

You show up with your plastic bootstrap knife and they have a bazooka with infinite ammo.

But if you see bootstrapped companies thriving alongside the VC-backed ones?

That's the signal you’re looking for. 

Not an empty market but one where people like me are already winning.

Think Problem-centric, not solution-centric

This is the most common mistake I see (and I’m guilty myself).

You fall in love with an idea. A product. A solution. You get obsessed with building it.

But nobody asked for it.

A friend of mine put €500k into a software company for lawyers. Built the whole thing. Hired a team. Then found out lawyers don't have the problem he thought they had.

His mistake was building a solution before talking to people.

I try to become problem-obsessed instead. 

Start with the pain. Talk to people. 

Find out what’s keeping them awake at night.

If you start there, you're way more likely to build something people actually want.

You gotta be problem-maxxxing, homie.

Don’t sell to broke people

I don't want to target broke market segments. Indiehackers, for example, famously have no money. Aspiring creators, students, musicians are all very tough to sell to.

It doesn't matter how good your product is if your customers can't afford it. You'll end up grinding for tiny payments while drowning in support requests from people who expect the world for $9.

B2B is often better than B2C for this. Businesses already have budgets. They're not agonizing over $200/month if it saves them time.

Target broke markets, get broke.

I wrote a whole newsletter about this recently, you can read it here

Don't reinvent workflows

Humans are habit machines. Changing how people behave is hard.

When I built the AI Course Creator I came up with these unique workflows using all kinds of different tools. And I felt like a gigabrain.

Then I tested it with beta users and reality slapped me in the face.

They struggled with every new tool I introduced.

People would get stuck after the first lesson and dropped off. 

So I scrapped most of it and spent 100s of hours rebuilding everything around ChatGPT and Google Docs. 

Suddenly people flew through the course.

If your product requires people to change how they work, you're adding friction before you've even delivered value.

The better play is to find what they're already doing and make one small part of it faster or cheaper. 

Your job is not to build a complex product, your job is to get people results.

Focus on Recurring problems

I learned this one the hard way with my info products.

One-time purchases are a fucking treadmill.

You sell a course, feel great for a day, then wake up and realize you need another buyer. And another. Every month you're back at zero.

Recurring problems mean recurring revenue.

Target Revenue leakage, not nice-to-haves

There's a difference between "this would be cool" and "this is costing me money right now."

Let's say you want to sell to e-commerce stores.

You could build a nicer analytics dashboard. Pretty graphs with better insights. You'll spend six months chasing people who say "let me bring this up with the team".

Or you could build something that recovers failed subscription payments.

Store does $100k/month. They're losing $10k to failed payments. Your tool recovers $8k of that. You charge $2k.

People will take this deal any time of the day.

That conversation is over in three minutes. They can do the math while you're still talking.

I want customers who are bleeding. You are helping them to stop the leakage.

Can I make money fast?

I wanted to build an AI video tool for compliance. Seemed like a real pain point.

Then I talked to people in that space.

Turns out companies that need compliance move slower than a sloth on ketamine.

It takes six months for anyone to sign anything.

If you're a solo founder, that timeline will bleed you dry. 

I want customers who can pull out their card and buy.

I want people to discover my product organically and pull the trigger without going through 154 zoom meetings.

How to guarantee that your next business won’t fail:

Go through this list and check your business ideas against these filters. See which red flags come up.

Or feed the list into Claude with your ideas and ask: "Which of these ideas passes all the filters? Which ones fail and why?"

Kill your ego. Go for the easy wins.

Analysis matters, but nothing happens until you act.

That Ryanair flight eventually took off by the way. 90 minutes late. Baby finally asleep. I was sitting in a death triangle of three sneezing post-Christmas-party drunks.

Had the classic Ryanair shortbread. 

By some miracle none of us got sick.

Now I'm back in Cyprus, making plans to absolutely crush it in 2026.

Looking forward to sharing my software journey with you as it unfolds.

See you next week,

Ole

P.S.

I'm deep in research mode right now and need your help. Fill out this form and I'll send you my LinkedIn Viral Whisperer n8n automation (normally a $35 product) + you can join a private Q&A call with me. Go to the form.