I didn't spend my VC money on Armani suits

I just met a fellow entrepreneur on a roof top party.
We've previously met a few months ago and I've told her my story.
At the party she told my current co-founder that I have an amazing story. I smiled, I know that I had 4.5 crazy years at my last startup. Then she said - "He had a rich co-founder and he spent all his money on perks".
I guess I was misunderstood by her (maybe by others too), so let me try again - from the beginning.

Sometime around 2006 Rodolfo called me and asked if I'd like to help him build a new company that will help people find what to watch on TV.
Rodolfo was a rich Italian media guy. "Rich" doesn't make justice with him because Rodolfo was more like a prince, coming from a royal family, having a famous Italian producer for a father.
We've met when I came to Italy to help with technical issues of an interactive TV show. Rodolfo owned the rights to use this technology in Italy and was able to run it in several sports related TV shows.

Rodolfo also approached Yoram, that was one of the founders of the previous company I've worked for.
Like all startups we had to have some brainstorming sessions before this idea forms into a company.
It all started with a brainstorm session in Paris. Rodolfo brought me, Yoram, Nick & Ping (who were helping us with the business model) and Pascal (A media business guy from Paris).

When I meet investors they like to ask me - "what have you learned from this experience?" or "what was your biggest mistake?". I've learned so many things, we (and I) made many mistakes, it's too superficial to mention one thing or one mistake.
But the seeds for the problems my company had started back then in Paris - brainstorming when you're not "hungry" is not a good idea.
Somehow a company's DNA is starting to form at the very first time the founders talk and it is almost always impossible to change it.
The DNA that was forming for us was broken. It was a "we already won" and "We are invincible" one.
Too little did we know that as a startup we are the underdog even if our chairman is a rich prince.

We've built a beautiful demo, Rodolfo had put a seed round of "money is no object" and we went big and hired about 10 employees pretty quickly.
The "royal" approach led us to meet the CEOs of the biggest telecommunication and TV companies in the world.
They all loved what we did.
We've managed to raise a few millions from a VC and hired more people.

I was the CTO of the company and it meant that not only I need to be on top of the product, but I'm also a critical ambassador for the company and had to fly all over the world to meet potential clients and partners.
I loved it.
Wearing a suit & tie from time to time. Meeting new people. Being constantly on the move. And doing all that for my own company - wow!

I did try to live well when I was traveling. It was hard not to, especially when Rodolfo was around.
When we were together in LA we stayed at the Beverly Hills Hotel. We drank a $2,000 bottle of wine (actually two of them). Rodolfo always paid for that, not the company. Ending a dinner with "Thank you Rodolfo" became the norm.
I loved the Bowery Hotel in Manhattan. It was not the cheapest place to stay at, but was not ridiculously expensive either.
My gross salary was around $120k/year but being around a rich prince, my life style was of a wealthier person.
Whenever I was in NY I bought expensive Armani jackets on their 5th Avenue store.

Back then I had a rusty and dirty 1998 Renault Clio. One time, when Rodolfo visited the Israeli office, I gave him a ride on my car.
He was reluctant to get into the car and after he did he told me in his very illustrative words - "When a girl enters this car her pussy heals".
The next week I came to the Lexus dealership store and asked to trade in my Renault Clio for a sports convertible Lexus.
I kept paying a monthly bill that equals a monthly apartment rent fee even after I had to sell it when my driving license was taken away for speeding.

So, yes, I've spent a lot of money back then. It was the money I've earned by working hard. Not taking any vacation for 4.5 years. Spending a lot of time far away from my kids, many times away on holidays.
Always trying really hard to bring value to my and my investors' company. When things were rough I was not too proud to roll up my sleeves and write code or do any other "dirty" work, even when I was already the CEO of the company.
When I became the CEO I tried to fight our awful DNA, I fired people, I minimised our burn rate, closed our fancy Milan office. But the DNA stuck up there, refusing to change and eventually killing the company.

How did I become the CEO of my company?
At the beginning Yoram was the CEO, Rodolfo the Chairman and I was the CTO.
Then Rodolfo became the CEO and Yoram left the company.
Back then Rodolfo was already fighting cancer.
That's something that most entrepreneurs will not experience - watching your co-founder die from cancer.
Rodolfo was always a strong and lively man, we were all sure that he will overcome his cancer - we are invincible, right? But things got worse and on our last meeting he looked like a ghost. He died a few weeks later.

On Rodolfo's funeral I've told his wife that I'll try to make his vision come true. I meant it. But soon after his death I realised that me and my investors don't see eye to eye on the way forward and I've offered them to resign and bring a new CEO onboard.
They were not able to bring anyone else. I've stayed and tried a "Hail Marry" to save the company.
Then, after 4.5 years, $10mm raised and many amazing experiences, my company died too.