Knocking on Destiny's Door
Desperation ignites an unforgettable first entrepreneurial leap
Working Hard with Grace Beverley
Jun 8, 2026 · 1 hr 12 min · 22 segments
I wanted to talk to Simon, because his whole thing isn’t really “quit your job and become a millionaire”, it’s much more about building a life that actually feels like yours and being honest about the…
Grace BeverleyHostI en- I enjoyed taking something from nothing and making it real, and I got a bit addicted to that.
So when I was in a job, what was security, I guess, which was the salary bit, wasn't enough to take away ...
The, I would pitch an idea to my boss, and they would say, "No, no, Simon, that's not what we do here.
That's, you know, we're not gonna take the inquiries and turn it into a business.
My, my ability to accept commands that didn't make sense or opportunities that were being missed, I, my brain just wouldn't accept it anymore.
If I had, if I hadn't started something that failed, I wouldn't have felt that feeling I'm talking about.

It's so funny, 'cause when you say that, that really makes me think of what I felt originally when ... 'Cause I only did 13 months in corporate before I, I guess, I became an entrepreneur.

And the only reason that happened, I think I would've done well more had I started that corporate, in that corporate world after university.

But because I did that before university when I was 18, and I had s- the one main thing I had issues with in the corporate world, I didn't mind the hours, I didn't mind having a boss, I didn't mind ... or I found it very glamorous.

The thing that frustrated me the most was when things were being done slowly, inefficiently, or in a way that didn't make sense to the business, and there was no way to change it-

I think had I not got so frustrated with that, I would've gone to university, started the businesses as I did, and still gone back into corporate.

Because I would've thought, "Just as I haven't tried entrepreneurship, I haven't tried my corporate dream yet."
I en- I enjoyed taking something from nothing and making it real, and I got a bit addicted to that.
So when I was in a job, what was security, I guess, which was the salary bit, wasn't enough to take away ...
The, I would pitch an idea to my boss, and they would say, "No, no, Simon, that's not what we do here.
That's, you know, we're not gonna take the inquiries and turn it into a business.
My, my ability to accept commands that didn't make sense or opportunities that were being missed, I, my brain just wouldn't accept it anymore.
If I had, if I hadn't started something that failed, I wouldn't have felt that feeling I'm talking about.

It's so funny, 'cause when you say that, that really makes me think of what I felt originally when ... 'Cause I only did 13 months in corporate before I, I guess, I became an entrepreneur.

And the only reason that happened, I think I would've done well more had I started that corporate, in that corporate world after university.

But because I did that before university when I was 18, and I had s- the one main thing I had issues with in the corporate world, I didn't mind the hours, I didn't mind having a boss, I didn't mind ... or I found it very glamorous.

The thing that frustrated me the most was when things were being done slowly, inefficiently, or in a way that didn't make sense to the business, and there was no way to change it-

I think had I not got so frustrated with that, I would've gone to university, started the businesses as I did, and still gone back into corporate.

Because I would've thought, "Just as I haven't tried entrepreneurship, I haven't tried my corporate dream yet."
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3 of 5
Knocking on Destiny's Door
Desperation ignites an unforgettable first entrepreneurial leap
Purpose Found Inside Personal Pain
He links purpose directly to past wounds
Every Entrepreneur Has A Boss
Founders admit who truly signs paychecks today
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