Why Leverage Matters More Than Hustle: Real Lessons From a Decade of Entrepreneurship
Solopreneur Letters #12
Two five-year cycles.
Two completely different approaches to leverage.
Both failures in their own way.
First five years: I built a hotel from nothing.
Managed a huge team.
Handled millions in investment.
Created something real and tangible.
Next five years: I became a solopreneur.
Started over from zero.
Pretended none of that experience mattered.
Here's what I've learned about leverage: it's not just about automation.
It's about creating assets that can pay you back repeatedly.
And most of us are terrible at getting the maximum juice out of what we've already built.
The Clean Break That Cost Me
When I left the hotel project and started freelancing, I wanted a clean break.
Emotionally, I needed distance from my partners and that whole experience.
So I did the stupidest thing possible: I ignored five years of expertise.
I had experience managing teams and budgets.
I understood the travel and tourism industry.
I knew digital marketing.
I had a network of contacts.
The smart play?
Become a freelancer focused on travel and tourism.
Do digital marketing for hotels. Consult on hospitality projects.
Instead, I started from scratch in a completely different space.
Why?
Because leverage felt too much like the past I wanted to escape.
When Hustle Without Leverage Burns You Out
I've spent most of my time as a solopreneur in survival mode.
When you're just trying to stay afloat, creating systems feels like a luxury.
You're not even sure what's going to work, what's worth putting the effort into.
What's going to be a one-off thing that you try once and it doesn't work versus something that you should double down on?
The hotel was supposed to be leverage - a business that would run itself and pay dividends.
I imagined having this asset that earns money, pays me a salary, opens doors.
I put everything I had into it, including my life savings and some of my best productive years.
But I left before it became fully operational, and I wasn’t able to extract value from what I'd built.
As a solopreneur, I've been starting and stopping, second-guessing and questioning everything.
Even when I commit to something, a few days in the doubts start sticking up their heads.
The result?
Five more years of hustle with minimal leverage.
Building assets I either never fully finish, or that I give up on too early.
What Leverage Actually Means
Leverage isn't just automation and AI workflows (though those matter).
It's an asset you build once that pays you back multiple times:
Content that brings leads for months
Systems that save hours every week
Experience that makes you the obvious choice
Networks that open doors
Templates that speed up your work
Frameworks that solve problems repeatedly
Hustle without leverage just burns you out.
Hustle with leverage makes you free.
The Fumbling Reality of Building Systems
Here's the truth about being a solopreneur: most of us are fumbling through the dark.
I'm building some systems that work.
SOPs, bots, automations.
But in other areas, I'm failing miserably.
Half-systematizing.
Building things once and then not reusing them properly.
I write newsletters but don't repurpose the content.
I solve problems for clients but don't turn solutions into templates.
I learn lessons but don't document them into frameworks.
How to Know What's Worth Systematizing
The key question:
How do you decide what's worth the investment of creating systems and leverage?
I think once you realize something is going to be a regular part of your work - whether daily, weekly, monthly, or quarterly - that's your sign.
Start with the daily things because that's where you can get the most leverage.
If you can automate or systematize the things you're doing daily or weekly, those efficiencies pay off faster.
But you've got to do the thing a few times to even know what to systematize.
You can't create a system for something you haven't done enough times to understand how it works.
Maybe This Is Just How It Goes
Sometimes I think fumbling in the right direction is the best any of us can do.
You build something.
You learn from it.
You try to extract more value.
You mostly fail at maximizing it.
But you learn something along the way.
And you carry that with you to the next thing.
The hotel taught me project management, team leadership, and how to handle pressure.
Each thing I’ve tried as a solopreneur has taught me something.
About what works.
What doesn’t.
About myself and what I want.
And about how to build true leverage.
What I'm Asking Myself Now
As I build things now I'm asking:
How can I reuse this?
How can I extract maximum value?
What would squeezing every drop of juice from this look like?
And then actually doing it instead of moving on to the next shiny thing.
This is Letter #12 of 'Solopreneur Letters' – a series I’m writing where I share the hard-earned wisdom I wish I’d had when I started on my solopreneur journey. See the full list:
