How a flight to New York changed my perspective on entrepreneurship forever…

It had been on my ‘Bucket List’ for years: attending a Jay-Z concert in the city where he grew up: New York.

I think I’d been to about 10 Jay-Z concerts before then, but to see Jay-Z at the Yankee Stadium in New York seemed pretty amazing. During a trip to Ibiza I saw a message online that he would do a one-time concert in New York, together with Justin Timberlake – at the Yankee Stadium…

I booked straight away, of course! 


I decided to treat myself and booked front row tickets and a business class return flight.

The thing I love about flying business class is not only the luxuriousness and the electrical outlet attached to every chair (!), but also the people you meet during these flights.

These people are usually entrepreneurs with interesting stories and when I boarded this flight I had no way to know that this flight would change my entire perspective on entrepreneurship forever…

I entered the plane and got comfy. I noticed that I was sitting by myself while the rest of the cabin was fully occupied. I expected to have no neighbour on this flight, which could be nice for a change!

Even so, right before departure a guy dropped down next to me and the first impression I had of him was that he seemed like an interesting fellow. He looked like a true bon vivant.

“This is what they call ‘just in time management’!” was the first thing he said to me. Seemed like an okay guy!

He was a tad restless because he’d had to hurry, but he seemed to be in good spirits. He sat down with his sweaty forehead and all and we shook hands. Nice.

“I forgot all about the time and had some business to attend to before I left, but it worked out in the end!”

After shaking my hand he took out his iPhone to use every single second he’d still have internet to send out e-mails and other messages.

When the stewardess asked him to put his phone on flight mode he became a bit less fidgety and started a conversation with me.

“So, to the big apple!”

Yep, that was where I was headed.

New York, baby!

I really love New York. I ran the marathon there in 2006 and from that moment on the city has held a special place in my heart.

He asked me what I would be doing in New York and I told him I’d attend two concerts. He did not really react to this and started telling me about some of his earlier New York adventures.

He was a nice enough guy, but something seemed off…

I asked him what he would be doing in New York and he told me that he was going ‘for business’.

In order to keep his privacy I won’t tell what kind of business he was in, but it sounded very interesting.

He told me he’d been in business for about 30 years now.

While he was downing his second glass of champagne in 10 minutes, he told me he had a team of about 25 people and that this was the eighth time he’d been aboard a flight this year – it was July.

So, a busy man.

He remained a bit vague about what he would be doing in New York, so I did not ask him overly much.

He told me about his life. About his three children, his four grand children and about all the travelling he’d done so far.

“Being a granddad is the greatest thing ever, all the pleasure with none of the pain!”

He told me about his cars, the fat profit he’d made with his business and the ‘golden days of yore’. He was truly an ‘open book’.

Or so I thought…

He was the image of the experienced entrepreneur. 

I noticed that his entire way of being radiated a certain enjoyment of life. Within one hour, he had downed five drinks and all the while he was sharing tall tales.

I started to wonder whether, despite his obvious enjoyment of the nice things in life, he was truly happy. It was overly obvious that the man was tired, but still high in energy, if you know what I mean. A tad restless.

At a certain point I saw him take an insulin syringe from his hand luggage and he walked to the toilet to reappear after a few minutes. He made no comment on this.

(Good combination with the alcohol, too.)

He told me he would have a business meeting at 3 PM, that very same day. We would be landing at 11:30 AM, so it should be no problem. I did not expect he was going to be sober during that meeting.

He said he was going to take a little power nap and put his chair in the reclining position. Literally a few minutes later he was snoring next me and he woke up about 5 hours later, 30 minutes before landing. Respect.

He would probably be a lot fresher for his meeting as well now 😉

After landing (and two cups of coffee) I shook his hand and wished him all the luck in the world with his business endeavours in New York.

“That’ll be fine”, he said with a big smile.

It seemed like fine thing, such a guy who was still happily in business at his age.

Boy, was I wrong…

A painful story…

I spent a few amazing days in New York. On Thursday evening I went to a so-called block party in New Jersey for a “Naughty by Nature” concert and on Friday evening it was time for Jay-Z and Justin Timberlake.

jay-zjustin timberlake

On Saturday and Sunday I chilled out in New York and met up with a friend… Good times.

I flew back on Sunday evening – which is ideal, because it makes sure you’re able to sleep and arrive home pretty well-rested. Or so I expected anyway, not knowing that I wouldn’t be getting any sleep at all…

I went through customs, accidentally left my Macbook there (which I noticed when back in the Netherlands, lovely) and sat down in the lounge. Guess who I ran into!

He was sitting at the bar and I did not disturb him there. I read my book and when on the plane I was sitting by myself for quite a while, just like before. And again, he entered the plane just in time and guess where he was seated…

What are the odds!

I wondered what his story was and thought it nice to be able to enjoy his company again – yet it was not the same as on the outward journey.

He didn’t make any funny remarks and did not shake my hand.

It was almost as if he did not recognize me at all…

He looked like crap…

The huge smile he had on his face on the way to NY was replaced by a worried expression. He literally looked like he had aged 10 years  in just a few days. His skin looked ashen even though there had been a heat wave in New York the past few days.

I didn’t know what to say, so I asked the dumbest question I could’ve asked.

“Had a good time?”


Oof, I thought.

“What is the matter?”, I asked.

“I’d rather not talk about it“, he replied, so I shut my mouth and took up my book again.

He was staring ahead with a vacant expression and shook his head – no.

He kept shaking his head. It got a little uncomfortable. 

I was almost afraid that he was pissed off at me. “This is going to be a long flight,” I thought.

I felt the tension, so I could not really focus on my book. Within a few minutes he broke his silence.


“Bollocks”, he said. “Bollocks, bollocks, bollocks,”  he repeated.

I looked at him and the cheerful, enthusiastic bon vivant of the earlier flight was transformed into a depressed mess.

It got even more uncomfortable when he started crying.

I did not say anything, but I looked at him for a second.

“It’s all over ,” he said.

I did not know what he meant and I thought something awful must have happened with his family or something like that.

“It’s best if I shut everything down, all has been for nothing.”

I figured he might be facing a lawsuit or something, but that was not the case.

“It was all or nothing, and now it’s nothing.”

Where he had not really revealed too much on the way to New York and had convinced me that his business was running smoothly, he now skipped all the superficial chit-chat and became a hundred percent honest with me.

He told me that he’d gone to New York to close a deal with a customer, but that, after two days, this customer had chosen to work with a competing company instead.

I figured this wouldn’t be the end of the world.

“Those jackasses have chosen a competing company with higher rates, worse performance and more arrogance. They can go to hell for all I care.”

He told he he really needed this deal, including an advance payment from the customer, in order to be able to pay the salaries of his staff next month.

He was pretty much bankrupt and could not see any solution to change the tide.

The tax department had already sent him a couple of formal notices and he had not paid his own salary in a while now.

“I’ve had nightmares of blue envelopes for years now, and now they’ve got me.”

He had a bunch of outstanding invoices with his suppliers and was three months behind on paying his private mortgage. He was four days late in paying his team and now he had to face the facts.

“I am terribly ashamed, who would have thought.”

He had to return to the office and tell his entire team that they would not get paid this month.

He had to tell his wife he was unable to pay their mortgage and he had to notify his suppliers that he could not afford to pay their bills.

“This is so unlike me, but I just don’t know what to do now.”

Pff, tough stuff.

I’ve been working with entrepreneurs for eight years now and I am the kind of entrepreneur who usually comes up with solutions for most kinds of problems. I started asking him questions so I could give him some suggestions, but I realized the suggestions weren’t coming to me…

I had no idea what he had to do.

He was already in such deep trouble that he needed a miracle to get out of this shit.

Even if he had closed the deal in New York, he would still have been in deep shit, but he might have been able to survive for another month or two.

It would have postponed the inevitable, nothing more.

He had already had quite a lot of drinks at the airport and even though he’d said he didn’t want to talk about it, he needed to get things off his chest.

He told me he’d always had a positive attitude, but always been a bit worried about things – even so, he’d always kept going.

The light worries he’d felt always made him feel a tad restless so he often needed external stimuli to find some sort of peace and quiet.

“Because of that damned stress I now I have to press a needle in my stomach every day,” he said, referring to the fact that he’d become a diabetic.

“It’s all my own fault.”

It hurt to hear his story.

“I’ve never really got my act together, yet I always thought I would be fine. I always made it eventually, but now I’ve really failed.”

The things that was really painful to hear was that he experienced some amazing moments, but that hadn’t been able to truly enjoy any of them.

He told me of his son’s marriage, which supposedly was a great day – he doesn’t really remember any of it.

He had awoken that morning and to find a direct payment order in his mailbox. Luckily he had just enough funds left to pay this specific bill, but it had ruined his day.

His son, who was also his best buddy, noticed he wasn’t truly ‘present’ that day, and later on he drunkenly reproached him for this.

There were a bunch of similar stories, all rather painful to tell and definitely not nice to hear about.

He told me his life was grand ‘on the outside,’ but that it had been a long time since he had felt truly relaxed and happy.

“I always felt rushed, I can’t find any peace and I can’t remember not being tired.”

“I have earned so much money and then spent it all.”

“I haven’t told my wife, but she noticed ages ago that things aren’t going well. She’ll be picking me up from the airport and I will have to be honest with her. I am not even sure we can keep living in the same house. I am so embarrassed.”

No matter how much I wanted to, I couldn’t think of a solution for his problems.

“Shit man, I don’t know either,” I had to confess…

“I am going bankrupt. Utterly bankrupt.”


It wasn’t an ideal flight, but no matter how odd it sounds, it did bring me a lot and gave me a couple of powerful insights.

It may be painful to read this story and even writing it down makes my stomach ache, but the painful reality is that this story is no exception.

I often hear these kinds of stories, in many shapes and sizes…

When consulting statistics, you will notice that the majority of entrepreneurs go bankrupt or out of business, simply because their revenue isn’t what it should be and, perhaps even more importantly, they don’t make enough of a profit.

A large percentage of entrepreneurs who do stay in business – I call these types of entrepreneurs ‘builders’ – work unitl they drop, don’t build their capital and are ‘trapped in their own business’.

Then there is that relatively small percentage of entrepreneurs who seem to have their businesses running smoothly. They work ‘on’ their business rather than ‘in’ their business.

They work ‘normal’ hours, are relatively relaxed and are able to distance themselves from their business and still make good money. I call these entrepreneurs the ‘architects’.

The architect has taken control of his business rather than allowing his business to take control of him.

If, twenty years ago, my neighbour had decided to make the transition ‘from builder to architect’, then his story would’ve been very different. Now it is too late.

He made a lot of money, worked his ass off and it took him ten years to learn that his way of working turned out to be the wrong one. He had always been the builder and was convinced that he just had to work harder to solve his problem.

He went bankrupt and lost a lot. I do not know how he is doing now, but I can tell you he was in a tough situation.

No matter how hard we work in our businesses, if we find out after many years that this hard work did not bring us anywhere, then it is time to make a choice.

How much money is there in your bank account compared to, for example, three years ago? Is it more or less than before? How many hours do you work per week and is this more or less than three years ago?

If your results are the same, or perhaps even worse, then it is time you make a choice. Doing the same thing over and over expecting different results is madness, according to good old Einstein. The man had a point.

“When you do what you did, you will get what you got.”

As entrepreneurs, we’re supposed to become better and smarter and the special thing about entrepreneurship is that you can literally measure becoming a ‘better entrepreneur’ by measuring your finances, the amount of hours you work per week and your stress level.

My big insight is that we should not make concessions when it comes to creating the company that is right for us; we should not chicken out when it comes to creating a buffer and making a lot of money and using this to build ‘ON’ our business in a completely relaxed way, rather than IN our business.

Stress is killing.

Freedom is a great thing and too many entrepreneurs experience the opposite.

My insight is that we should constantly be aware of whether we are adapting our lifestyle to fit our business, or adapting our business to fit our lifestyle.

Making money is hard enough in itself, keeping money is ten times harder.

Was this story of value to you? Feel free to share, Tweet or plus it! A personal tweet to @EelcoDeBoer is always appreciated as well :)

Good luck!

Eelco de Boer

  • 9 November 2014
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