I've Failed at More Business Models Than Most People Have Tried. (Here's What That Taught Me)
The lesson was never about the business. It was always about the people.
Let me give you the list.
Marketing agency. Web design agency. SaaS. Dropshipping. Print on demand. Lawn mowing company. Rank and rent websites. Ecommerce. And a few others that didn’t even make it far enough to deserve a name.
Most people read a list like that and see failure. I read it and see tuition. Expensive, time consuming, humbling tuition that no course or book could have given me.
Because here’s the thing nobody tells you when you’re starting your first business.
The model is almost never the problem.
The lawn mowing company
I want to start here because this one surprises people the most.
Yes. I ran a lawn mowing company. Not because I had a passion for grass. Because I understood the model. Low startup costs, recurring revenue, local demand, simple operation. On paper it made complete sense.
And it worked. Operationally it worked fine.
But what I didn’t account for was the people. The client who changed the brief after the job was done. The one who paid late every single time and had a different excuse each month. The one who wanted more for less and made you feel like you should be grateful for the opportunity.
I wasn’t bad at lawn mowing. I was learning, for the first time, that the hardest part of any business isn’t the service you provide. It’s managing the humans on both sides of the transaction.
That lesson cost me a lawn mowing company to learn. Worth every cent.
The agencies
Marketing agency. Web design agency. Both taught me the same thing from slightly different angles.
Agencies sound great until you’re inside one. You trade time for money, which is fine at the start. But then scope creep sets in. The client who hired you for one thing wants three things. The brief that seemed clear becomes a moving target. The relationship that started professionally slowly becomes the most draining part of your week.
I was good at the work. That was never the question. The question was whether I could manage clients, set boundaries, have difficult conversations, hold my price when someone pushed back, walk away from business that wasn’t worth the cost it was extracting from me.
Those are not marketing skills. They are not design skills. They are people skills. And nobody teaches them to you. You learn them by getting it wrong enough times that you finally figure out what right looks like.
SaaS and the dream they don’t show you
Everyone is building a SaaS right now.
AI made it possible. No code tools made it accessible. And the internet made the math look irresistible. $300 a month. 100 customers. $30,000 a month. Recurring revenue. Automated onboarding. Practically runs itself.
I did this years ago. Before it was the thing everyone was rushing into. Before the no code revolution made it feel easy. And I want to tell you what they leave out of that $30k a month fantasy.
The product is the easy part.
What nobody talks about is what happens after someone pays you. The onboarding that looks smooth in the demo and falls apart the moment a real human touches it. The support tickets that come in at midnight from customers who don’t understand the thing they just bought. The churn that happens not because your product is bad but because you couldn’t get people to the moment where it clicked for them.
SaaS is not a software problem. It is a people problem dressed up in a subscription model.
Training people on a product they don’t fully understand yet. Managing expectations that were set by a sales process that made everything look simpler than it was. Holding the hand of a customer who is frustrated and about to cancel while simultaneously trying to build the next feature that will stop the next customer from having the same problem.
I learned more about human behaviour running a SaaS than I did in any other model. Because you are not just selling a product. You are selling a transformation. And transformation requires people to change how they work, how they think, how they operate. Most people resist that even when they paid for it.
The $30k a month is real. The spreadsheet works. But between the spreadsheet and the reality is about ten thousand hours of people work that nobody puts in the YouTube thumbnail.
The product businesses
I tried dropshipping. Print on demand. And eventually something far more personal than either of those.
Dropshipping and print on demand follow the same basic logic. Find a product, find a supplier, sell it without touching it. The margins are thin, the competition is brutal, and the customer on the other side has no idea or care about the chain of people between them and the thing they ordered. When something goes wrong, and it does, you are the face of a problem you didn’t create and can’t fully control.
I learned from both. But neither of them ever felt like anything more than a transaction.
Then I tried something different.
I built a brand around leather products and put it under my grandfather’s name. Not as a marketing decision. As something personal. A way to build something that meant something. Something close to me, connected to someone I respected, carrying a name that deserved to stand for quality.
And that’s exactly where it fell apart.
When I tried to do it with integrity, to source well, to price honestly, to sell something I actually believed in, the margins didn’t work. And when I tried to make it work financially, I would have had to compromise the very thing that made it worth doing in the first place.
I couldn’t put my grandfather’s name on something I wasn’t proud of.
So I shut it down.
Not a failure of execution. A discovery of where my line was. And the discovery that I wasn’t willing to cross it regardless of what was on the other side.
That’s not a business lesson. That’s a life lesson. And it only came from doing the thing, not thinking about it.
Rank and rent
Rank and rent is a clean model on paper. Build a website, rank it on Google, rent the leads to local businesses. No product. No client work. Just digital real estate.
I understood the mechanics. I could build the sites. I could do the SEO. The part I underestimated was the other end of the phone.
Local business owners who didn’t understand what they were buying. Who needed educating before they needed leads. Who questioned the value the moment things slowed down. Who wanted a guarantee that no honest person in this industry can give.
Again. Not a technical problem. A people problem.
The model works. The relationships around the model are where most people quietly give up.
What all of it actually taught me
Here’s the insight that took every single one of those models to arrive at.
Business is 80% how you deal with people. The actual doing, the service, the product, the model, the execution, that’s maybe 20% of the equation.
I kept changing the vehicle thinking that was the problem. New model, new niche, new opportunity. But the lesson that kept showing up, in every lawn, every client meeting, every supplier dispute, every support ticket, every refund request, was always about people.
Can you have a hard conversation and keep the relationship intact. Can you hold your price when someone pushes back. Can you walk away from money that costs too much. Can you earn trust from someone who doesn’t know you yet. Can you deliver on a promise when it’s inconvenient. Can you admit you got something wrong without it breaking you.
None of that is taught in business courses. All of it is learned in the field.
Why I’m telling you this
Not to impress you with the list. Not to perform struggle for relatability.
Because all of that, every model, every failure, every lesson learned the hard way, is what’s sitting underneath what I’m building now.
I’m building a one person business with a $1M target. No employees. No office. No overhead. And unlike every previous attempt, this time I’m not starting with a model. I’m starting with what I know. The writing. The thinking. The people skills that took years of getting it wrong to develop. The understanding of what I’m willing to compromise and what I’m not.
Every business I shut down taught me something I’m using today. The lawn mowing company taught me how to handle difficult clients. The agencies taught me how to hold my price and walk away. The SaaS taught me that selling a transformation is harder than selling a product. The leather brand taught me exactly where my line is.
And don’t get me started on the online courses.
Writing courses. Social media courses. Design courses. Sales courses. Marketing courses. I’ve spent more money on education than I’d like to admit out loud. And here’s the thing, the learning was real. I enjoyed every single one of them. There is something genuinely satisfying about acquiring knowledge, understanding frameworks, seeing how people who are good at something think about what they do.
But then comes the doing.
And the doing never looked like the course said it would.
Because a course can give you the map. It cannot walk the terrain for you. Every framework I learned had to be unlearned just enough to fit my specific situation, my specific strengths, my specific line that I wasn’t willing to cross. I know a hundred ways to do what I’m doing right now. Proven methods. Tested frameworks. Strategies with case studies attached.
I’m carving my own path anyway.
Not because the knowledge was wrong. Because the application is always personal. Always specific. Always something you have to figure out for yourself regardless of how good the instruction was.
None of that was wasted. All of it was preparation I didn’t know I was doing.
If you want to see what I’m building with all of that behind me, start here.
And if you’re at the start of your own list, somewhere in the middle of a model that isn’t working, I want to offer you a different question to sit with.
Is it the model? Or is it the people side of the model that you haven’t figured out yet?
Because the model is the easy part. You can learn a model in a weekend. The people part takes years. And it only starts making sense when you’ve failed at enough different things to see the same lesson showing up in all of them.
That’s the real education.
Everything else is just the vehicle it arrives in.
Kal