Posted Leave a commentPosted in 4 minute read, FAILURE STORIES

Chris Sacca is as an extremely successful venture capitalist, with stakes in Instagram, Kickstarter, Uber, Twitter, and dozens of other prominent start-ups like Stripe, Lookout and WordPress. He’s widely known from being ranked third on Forbes annual Midas List of tech’s 100 top investors as well as being a recurrent quest on Shark Tank. What is not so familiar is how his incredible journey started. Investing his student loans, making tones of money, losing a lot more and ending up with 4 million in debt.


Student loans

Although Chris succeeded in school his entire life, he had no idea what should be the purpose of his life. He studied advanced mathematics and was on the honor roll for 12 straight marking periods.  By 11th grade he felt burned out and wanted to pursue a college degree where there would be no math.  Chris took the natural step of going to law school. He quickly realized that going to classes is entirely optional and he can use that time start his own company thanks to government money from his student loan checks.


Hot hand

The company quickly folded and Chris used the money that was left to hit the stock market.  He invested in several of the hottest tech stocks of the decade. Not only he was successfully investing his student loans, but he leveraged the gaps he found in the terms and conditions of day trading platforms. Chris turned tens of thousands of dollars for his student loans into $12 million by 2000.


Bubble burst

At that point, being still a very young and inexperienced investor Chris never thought of cashing out some of his virtual money. Instead, with very little diversification, he continued to double down. You can probably guess what happened next. When the stock market crashed several of Chris’ stocks quickly plummeted and very quickly he found his paper net worth had fallen to $2 million. Feeling disappointed and overwhelmed he decided to take a break, clear his mind and walk away from the stock market for several weeks.



While he was travelling to Austria the leftovers of his portfolio dived even harder. An informal remark by Bill Clinton and Tony Blair about joint policy in the notion of patents around genetic technology, when viral in the news.  As the companies from this industry were the core of Chris’s portfolio, there were not much left this time. Playing this dangerous game and not giving himself the extent of the margin in his investments, Chris immediately wind up $4 million in debt with no means of paying it back.


Adult sites

Still keeping his nerves, he refused to declare bankruptcy and negotiated a workout plan with his creditors which reduced his total debt to $2.125 million. Over the course of next five years Chris completed law school, and got his hustle on. He worked for one of Silicon Valley law firm, but got fired after 13 months. Next step was opening up his own consultancy. This journey took him through writing terms and conditions for online adult sites and a variety of other less than impressive tasks. Remarkably, he managed to pay down the two-plus million dollars in debt at some point in 2005.



For the next four years Chris worked at Google. After that started his first angel investments in PhotoBucket and Twitter, for which he is much better known. What few realize, however is that his success today very nearly didn’t happen. It was his tenacity and refusal to quit, even when reckless at times, that paved his road to becoming one of the most respected and successful angels in Silicon Valley.



Chris didn't study business or engineering, doesn't know how to program a computer or worked at a big venture firm. So how did he pulled it off? He does it by buddying up with well-chosen founders and very often serves as a mentor. It seems like he could take on everything but Chris only takes those ventures and endeavours in which he can be an asset.  On top of that neither massive debt, lay off, nor anything else is able to stop him.



Posted Leave a commentPosted in 6 minute read

Knowledge is having the right answer. Intelligence is asking the right question

We have previously learned in Power of Questions? Part 1 why it’s so important to start asking questions to yourself. Question yourself first and then start adding value to your life and other people life. Hopefully after reading this article you will jump with me on this one-day challenge. I am not asking for much. One day. One question. That’s it.


Tenacious curiosity

During the curse of our life we face a lot of problems, do you agree? Some people say that there are no problems only opportunities. Of course there are lessons to be learned in every problem, opportunity or failure but we still have to deal with them. There is a great technique to revel the roots of our problem, including inaction. It is the method of 5 Whys. It is a simple interrogative technique to explore the case, that was developed by Sakichi Toyoda and used at first by Toyota Corporation. The method simply comes to asking the question Why? As many times as it takes to raise emotions. In most cases after the 5th Why? you will discover the root cause of the problem. Besides releveling the nature of the case usually the solution will become clear. As I said the idea of this technique is very simple but getting it right is not so easy. You might think it is just asking few question, how hard it could be?


Requests for information

Well, this may come as a surprise for you, but as it turns out it’s problematic because we don’t really know how to ask questions. We ask questions without even thinking about them. How was school? How was work? Did you like it? Are we really looking for answers or are we just subconsciously feel obligated to ask them? First thing is that we are not really sure what information we want to get by asking those question? Questions are simply requests for information but we tend to forget about it. If we get to the third question, and most people stop at two, it has nothing to do at all with the first on. Even if we know what information we are looking for, we give up on this quest surprisingly easily. What you need to do to identify the roots of your inactions, is to practice asking questions based on the 5 Whys model.


Adding value

Those very simple and basic things will allow you to add a great amount of value to your life. If you’re asking yourself better and more specific questions you are going to discover greater capabilities within yourself. There is a lot in you that you don’t know yet. Don’t you want to uncover that?



It will also allow you to influence others in a far greater way. I’m not talking about manipulating. I’m talking about helping, leading, motivating and inspiring. Once you are able to help others and ask them better questions, then you are going to be the person everyone always wants at the meeting. You are going to be the person everyone always wants to ask questions. You are going to become the influencer in the group because you’re helping people think of the things they wouldn’t usually do. If you will become that go to person, all the big ideas they have, they are going to want to bounce against you. Benefit from that and let others inspire you on your Journey. 


What do you want?

From being miserable at work, to loving it. Being successful means to me to be able to respond and actually anticipate the invitation of an upcoming opportunity. It is always an opportunity to grow, to develop, to become and to progress. But the biggest, the most fulfilling of all successes is making your life what you want it to be. Now the big question is What do you want from life? What do you really want?


Dig deeper

We have much more powerful capabilities than most of us think that we have. By asking the right questions you can control your fear. You can get your priories in line and understand what is going on. Questions build your vision, your dreams and your Journey. Don’t go for the first answers. Dig deeper. Go further. Don’t be ashamed to ask 5 follow up questions. Get into the core of the case or a problem. The more you understand something, the more confidence you have in that area. Ignorance and unawareness won’t get you anywhere. Ask more and better questions, learn more about your colleagues, your friends, your business partners, your employees and understand them better. In work and business environment we actually know very little about each other. By asking those question you will get a great connection point, a great start to your next small talk. You will get them more comfortable and get yourself a very powerful leverage of knowledge, trust and personal bond. Our life is long game but not all of us are playing a long game. Treat those question as investment and don’t expect a quick payback. Payback will come but you have to be patient.


One Question

Now I dare you to ask one extra question to each person you interact with at work. One question. Tomorrow. It could be interactions by the coffee machine, at the meeting, training session, by your desk, wherever. Make this question a little bit private. Don’t ask about weather. Make it positive and light. If you are asking How was your weekend? Try to go a little bit deeper. Look for good in others. Be creative. Be playful. Ask this one question, enrich your everyday interaction and relationship. One question. How hard it can be?  


Thanks for reading! 🙂 If you enjoyed it, hit that heart button below and share it with your friends.