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10 Success Tips From My $100M Friend Turned Homeless Man



In 2010, I met a man who was worth in 2007, $100M from starting his own business. What I didn’t know in 2010 was that the man, who would later become my friend, was actually bankrupt and homeless.

The story is quite an odd one so I will do my best to briefly tell it for you. In 2007, my friend received a legal notice to his business address. The legal notice was for something minor, and so he sent it on to his lawyer for review.

Over the next few months, his lawyer worked through the matter, and it was nearly resolved. What happened next was quite unexpected; his lawyer was shot dead in the middle of the street while trying to help a woman that was being attacked by a man.

The lawyers bravery, unfortunately, saw him shot in the head at point-blank range, although he didn’t die for nothing and will always be remembered.

What followed next was a series of bizarre events. This minor legal matter was forgotten about by my friend, and he had thought that his lawyer had resolved it. When he found out it was unresolved, he learned that the solution to the matter died with his lawyer.

Things quickly turned bad, and within a short space of time, he was met at his famous mansion by the sheriff who went and repossessed all the belongings he had including the house. One strange thing though was that my friend got to keep all of his luxury clothes as these were considered essential items (these clothes became paramount later on).

The first night he was made homeless and had nowhere to sleep, a miracle occurred; his second daughter was born. With nowhere else to stay, the hospital became his accommodation for a short while until he was kicked out onto the street.

For the next few years, he and his two daughters under five years of age lived out of his beaten up car in a rough neighbourhood. He went from eating at five-star restaurants to eating food out of a can. The most frustrating part of all for him was that he had no idea what had caused his fortune to be lost, and the only person that knew was now dead.

My friend could have been one of the greats. He used to have the power to change the world with his incredible skill of coming up with an idea and then making money from it. Over the years, he has become a phenomenal mentor and someone who has taught me many lessons through the adversity he has faced, and the pain he continues to suffer to this day.

We often think that the art of success comes from what we learn off highly successful people, but I have found that some of the best lessons can also be learned by the ones that don’t end up succeeding too.

I am conscious that by knowing this man, I have begun to have a different view of success. My worldview has not only been shaped by the sensationalism we all see on social media, but by real people, and actual reality.

Below are the ten lessons this former $100M friend, turned homeless man taught me.

1. First impressions matter (it’s also easy to be deceived)

When I first met this man he was wearing a worn out pair of cargo pants and an unbuttoned chequered shirt. He came to the company I was involved with to interview for a sales job. Everyone in the office thought he looked like a loser and couldn’t sell to save his life (including me).

For some unknown reason, the sales manager liked him, and he was hired on the spot. What he taught me next I didn’t see coming. For the next four weeks, he called prospective clients and put them in his Salesforce opportunity list with some huge revenue numbers next to each one.

He was the joke of the office, and everyone thought he was dreaming. Generally, when a new sales person started, they would make their first sale within twenty-four hours. If you didn’t, you were usually fired.

To top it off, he had lots of cigarette breaks, hid in the corner without talking to the other sales people, and drank loads of instant Nescafe coffee (one every hour). By week four he had still not made a sale.

One Friday afternoon, the sales manager and I decided that it was time to fire him. I went down the stairs and into the sales office to find him, and strangely enough, he had gone home early. So, we agreed to fire him on the following Monday.

On Monday morning, I came into the office and looked at the sales whiteboard to see that he had made his first sale, and the dollar value was large. The sales manager and I thought we better give him a bit longer to see if it was a fluke.

What proceeded to happen from here was something I will never forget; he just began to put up sales every day. It was like a waterfall, and no one could stop him. Within a few months, he outsold the entire sales team on his own.

Like anyone achieving this level of success, myself and the other guys began to become intrigued by this man. As we got to know him better, we learned that he was better at building rapport than anyone we had ever met.

None of his sales conversations spoke of the product and usually just involved him talking about the customers hobbies, promising to come to their next barbecue, and then taking an order for some product in the last two minutes of the call.

So the success tip from all of this is that the way you dress matters and it could cause you not to get a chance, but at the same time, don’t judge a book by its cover. The strangest, quietest people can also be the most successful people you will ever meet.

2. Any skill can be learned if repeated enough times

As I delved a bit deeper into this man, I found out that before working with us he actually worked for a charity. Straight after he became homeless, he lost all belief that he could be successful again and found the quickest job he could.

The money he earnt at this job didn’t really help his homeless situation. His job every day was to be tied to a phone, working in a call centre, and calling people one after another to ask for a donation to the charity.

He rapidly learned how to get people’s attention and then quickly get money from them – it was all about trust. At this job, he became the highest grossing salesperson too and worked like a dog with only one or two very short breaks.

While he was good at sales in his startup career, the charity job took him to the next level and taught him many lessons, including the importance of confidence. As he was able to rebuild his confidence again by becoming the number one salesperson, he quickly decided it was time to move on from this job, and that’s when I met him.

3. Even a homeless man can get a loan for a Mercedes

This next success tip again took me by surprise. I used to tell my ex-millionaire friend about all these people I would meet that had very nice luxury cars. He told me anyone could get one even a homeless man.

I didn’t believe him until one day, he calls me up and says, “I just bought a new Mercedes Benz four-wheel drive.” At this time in his life, he was again unemployed and looking for the next job. I didn’t believe him and told him to come and show me.

Sure enough, he arrives at my house with the Mercedes-Benz. He explains to me that lots of people appear rich and that even a homeless man like him can have the same effect. He told me that getting a car lease is not that hard, but paying it back is a whole other story that takes discipline. What was interesting is that he had every intention of paying the loan back because he was optimistic he would earn the money he needed to, to fulfil his debt.

He told me that sometimes you have to take a risk even when you don’t know the outcome and to just have faith that you will find a way. In fact, he was adamant that having the loan was more likely to motivate him to get out of his current situation.

The success tip here is that you should never be fooled by possessions or someone’s perceived image. I personally have met many people who appear rich and are actually dead broke. It’s often their addiction to luxury cars that can keep them broke too.

Try to buy things that you can afford and focus on building a business or acquiring income-generating assets, and not material things that will never make you happy. At the same time, don’t forget to give a percentage of all the money you earn to create good in the world and help others.

4. Dishonest people will fall on their own sword (they don’t need your help)

Before all of my self-development training, I used to believe that it was my job to highlight dishonest people. What my ex-millionaire friend taught me was that dishonest people will bring themselves down and by bad mouthing them; I am only bringing myself down with them.

This lesson that he taught me has been proven time and time again. The best example is his brother who he introduced me to one night. After meeting his brother, he told me that I shouldn’t spend time with him because he was dishonest.

Initially, I didn’t get the message and stayed in touch with his brother until I learned the hard way.

“I quickly realised that having a toxic person in your network is a very bad idea”

Many people would ask me my opinion of his brother and rather than say bad things about him I learned to distance myself from him instead.

To make things worse, his brother would drop my name in conversations and pretend that we did business together. I would often get phone calls from people I knew saying that my friends brother had mentioned me, and they would ask me about him, I would just tell them that he was someone I didn’t know well (which is true) and that I am not currently doing any business deals with him.

Pretty quickly, my friend’s brother fell on his own sword, and people realised who he truly was. While I sometimes wished I never were introduced to him, I learnt a valuable lesson about dishonest people at the same time, which I will never forget.

5. The cost of missed opportunity

Following on from the previous point, my ex-millionaire friend taught me about how your own personal brand and your level of honesty can cause you to miss opportunities. He explained to me that when you screw someone over, the ripple effect and opportunities you will miss can never be measured.

The scary part about this success tip from my friend is that you will never know what those opportunities were, so, therefore, you will never know the true effect that being dishonest will cost you.

Every day that goes by, opportunities will be presented to people that are in the dishonest person’s network, and they will be turned down behind their back. They will never be able to have visibility of these opportunities or the chance to defend themselves. When you meet a dishonest person, they will often spend their entire life wondering why they are not happy or why they are unsuccessful.

On top of this, they will blame their circumstances on luck or timing. The hardest part of this concept is that it’s not something many of us learn, and the act of being dishonest separates us from realising the consequences of our action.

The only true way to avoid this problem happening to you is not to be dishonest – period. Personally, this is one of my favourite success tips from my friend and it’s become a true law of my universe that I swear by.

6. Your family is all you have

When my ex-millionaire friend had all of his material possessions taken away, he taught me a groundbreaking success tip. He taught me that above all else, your family is what truly matters. Even when my friend had nothing, he still had his family by his side that supported him and helped make him smile.

This idea is so simple, yet it’s truly inspirational when you think about it properly. In the early days of having money myself, people used to tell me how lucky I was and how my life was set. I would always respond to them with the same answer; “as quick as you can make money you can lose it. Always stay humble and remember what matters.”

7. Money is made through your passion not get rich quick schemes

For the last five or so years, my friend has still struggled with poverty and homelessness. The reason I believe this is the case is because he broke a universal law; he spent the last few years on get rich quick schemes.

My friend has tried to do things he doesn’t care about to make money and then he has quickly given up on each business venture.

Unless you tie passion to the act of making money, you will never be able to sustain the habits that are required to follow through on your business.

The good news is, in recent times he has gone back to what he’s passionate about and what made him rich in the first place. Since doing this, he finally looks like he may be able to get back on his feet and provide the essentials for his family again.

It’s been such a long road for him but sometimes, as much as you want to, you need to let those around you make their own decisions and learn the basic success principles themselves. Eventually, when they come to understand the same principles that we are all learning on Addicted2Success, they finally start achieving their goals.

8. Real friends give you the best advice when you’re down

A few years back I went through my own struggles as we all do, and my ex-millionaire friend taught me a lot. Due to his ability to sell to almost anyone, I thought that he could save me from my problems. I made the mistake of initially thinking that somebody else could do the growing for me.

My friend observed what I was going through, gave me some advice, but left me to take the action. He knew that if enough time went by I would be forced to act, and he used this to my own advantage. Sure enough, I took his advice and completely changed my life around.

This taught me that real friends give you the best advice when you need it, but they force you to get the lesson yourself because they know that’s the only way you’ll learn. Real friends give you direction and ideas, not forced opinions.

9. Smoking will cripple your health (and your energy)

Over the time, I have known my ex-millionaire friend he has smoked cigarettes heavily. Now we all have known for some time that this is not good, but through my friend’s eyes, I have seen something more worrying.

For the last few years, he has had some serious medical issues that have had the potential to take his life away, but that appear to be unrelated to his smoking. With each new illness, the link to his smoking has been ignored.

Part of the reason he hasn’t been able to get back to his former glory is that he just doesn’t have the energy to do so. Creating value for others in the form of money takes a lot of energy and hard work, and if you deprive your body of the one thing it needs (oxygen), then success can quickly become an impossible task.

10. Be humble and gracious

The final success tip my ex-millionaire friend taught me is always to be humble and gracious. Even with all of the pain he has experienced, he still does his best to come back to his family every day with just enough money to feed his daughters, and he will happily starve himself for his loved ones.

He never complains about what happened to him, and he always stays optimistic that he will be back on top one day. Back on top may seem like having his money again, but somehow, I think back on top for him will be seeing his children grow up and knowing that he taught them good values.

***Final thought***

So as you can see, my ex-millionaire friend taught me a lot of what I know. Still to this day, he has no income and barely keeps a roof over his head. While I still keep the faith that he will one day prove to the world his sheer brilliance, I also know that it’s a possibility that I am the only one that will ever know.

Many people walk by him in the street and have no idea of his gift. He comes across as a hard man, but deep down he is very kind. Deep down he has the principles of success buried inside of him, and I can only hope that he will reveal them to the world one day.

Don’t ever let money define you and never give up on your dream. Whether that’s building a nine-figure startup like my ex-millionaire friend, or doing something as simple as writing a book, remember what you have learned in this article, keep your head up, and stay humble no matter what.

Do you know someone who has fallen from their former glory? What did they teach you? Let me know in the comments section below or on my Twitter and Facebook pages.


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