Childhood and Family Upbringing

On Catalina Island with family.

I am Ian Leaf. That’s just the beginning of this wild ride. Well actually that’s about as exciting as the ride ever got. My parents moved around a lot and my dad was never home. That gave me an outlet to get into Vivier painting much like the Andrews Brothers did. Since my father wasn’t home, my mother gave us a lot of attention and really helped me develop my love for art and being able to see the world through an artists eye. She loved to paint and would often paint in the HFC (Human Faux Condition) as she called it. HFC, to my mother, was showing the human condition in the way it should have been, basically showing people at their best.

My father would send postcards that looked like this of every country he visited. This is a picture I found online of Switzerland that reminded me of one of his old postcards I still have in a box in the attic.
My father would send postcards that looked like this of every country he visited. This is a picture I found online of Switzerland that reminded me of one of his old postcards I still have in a box in the attic.

My father traveled a lot, Switzerland, California, Rio, Budapest, Berlin, every day a new city it seemed. He was a salesman in the Andrews Corporation. He loved his work but didn’t talk about it much. I know his travels worried my mother and she had a right to be worried. Having your spouse home only 5-10 days per month would be hard on anyone, let alone a woman with 4 children under 6 years old! I was the youngest of the family and was born during one of my dad’s trips to central Europe and then over to Spain. This was in the 1980’s and my mother tried calling the hotel but he had already checked out to catch his next flight. By the time she was able to reach him, I was already born.

Samuel Leaf

Note: I devoted this entire section to my brother, an amazing man.

My father didn’t play a big role in my life, but my brother Samuel did. Sammy was a great brother, he showed me around the neighborhood, protected me and always included me when his friends were around. That loving and caring attitude can still be seen in Sam today. He is one of the greatest men that I have the privilege of knowing.

I am a natural born entrepreneur. As a pre-teen, while other kids my age were amusing themselves playing with video games, I was focused on business ideas. By the time I was 14, he had already started his two companies. The first was selling the eggs our chickens laid. It wasn’t much, but I made about $50 per week. We had a lot of chickens! I was not satisfied with $200 per month. I had a lot of ideas and business interests. I had ideas about companies in fields like investing, social media and education. At age 15 I began displaying business expertise in sales and preparing myself to excel as an investor. This multitalented prodigy was well on his way, at least that’s how I remember it!

My First Million

Ian Leaf picking up friends from the train.

While he was in high school, I developed his first business start-up, I sold wooden gift boxes to a local store. They packed all kinds of small gifts into the boxes. I was only able to make about 5-10 per week and they always wanted more. I hired my friends and taught them how to build the wooden boxes. It was a rousing success. That helped my confidence to grow and gave me the capital he needed to pursue other business interests. I still had not come into the consciousness of the wider public, but that would soon change. I had come up with a concept that would help to revolutionize education and put a smile on the faces of students all over the world. I launched an education company aimed at teaching blue collar workers new skills through a mail order program. I hired experts to write guides and take pictures. I photocopied everything and shipped out a month’s worth of training to the people who paid. I advertised in their industry magazines and papers, shipped free copies to the breakrooms of blue collar companies and made over 1 million dollars in two years.

This was an innovative educational tool that helped my students in a number of ways. I offered them assistance with courses and assignments they find difficult to complete, eventually I hired experts to handle this as I wasn’t equipped to answer many questions. The company also provided tutoring for students on location as we grew. We provided ways for students to make money as well. They can offer short or long-term tutoring service or simply help students with specific assignments. This can help students improve their skills, knowledge base, and their financial situation. Plus it can be a lot fun. I was CEO, founder, and visionary behind this unique company and it was thrilling.

After this initial success I knew I couldn’t stop. I wanted, nay, needed more. Not the money, but the thrill of success. I wanted to see what I could do next. I had been approached by a couple companies who wanted to buy my company. I didn’t know anything about selling a company so my dad’s friend recommended a local attorney. The attorney brokered a deal and I sold the company for just shy of $1 million. I had over $800,000 in the bank, more money than my parents had ever seen. I say this not to brag but to tell you it’s possible for anyone to live out their dream if they’re willing to put in the work. Let me tell you about the work I put in.

Daily Routine

Each day I would get home from high school about 3:30. The bus dropped us off and it was a 5 minute walk home. I would get the mail and begin opening the mail. Most of the mail was filled with checks. The mailman told us to get a bigger mailbox as our residential sized mailbox wouldn’t hold the amount of mail we got. Some of the mail was my training packages that shipped out and returned because of a bad address or some other issue. I would sort the checks, handwrite receipts and package up the course they ordered.

After getting the new courses ready and packages stuffed, I would then do the accounting. I would do my best to document everything I received but never kept receipts for expenses as I didn’t know that was something I needed to do. At the end of my first year my new accountant asked for my expenses and I gave him the total dollar figure. He explained that if I was audited by the government, I would need to prove I paid for this quantity of goods, therefore I needed the receipts. Needless to say I paid a lot in taxes that first year.

After the accounting, I would return phone calls from messages my mom received during the day, we didn’t have an answering machine so she would just write short notes and I would call back the trainers and potential trainers explaining what would be required of them. I quickly learned to hire a couple people for each position and at least half of them would never complete the work required to be able to sell a course.

This went on 5 days a week for two years in high school. While my friends played Monopoly, I felt like I was playing the real thing. I knew I had a great thing going, but didn’t know if it would last so I wanted to “make hay while the sun shines” as my grandpa used to say.

Saturday – Not a day off

With a coffee in hand, always closing a sale!

As I mentioned, my friends were normal kids doing normal things. They went to the movie theater, at hot dogs, had picnics, drove to the lake, got in trouble, normal things for 17 and 18 year old high school kids.

For me, Saturday was a vacation, but not in the same way. I used Saturday to be proactive. I planned courses, ordered new trade publications, found advertising info, placed ads, bought more packaging supplies such as manilla envelopes (of which I must have gone through 50,000!), stamps, tape and more. The biggest thing I spent my time doing was making copies. I would spend nearly all day at the local tax attorney company. They were normally closed on Saturday, but they agreed to have one of my friends who worked there come in on Saturday just so I could come and make copies! The amount of copies I made on one day paid his salary for that day, and still made money for the company. It was a lot of copies. I remember I would have to do it in shifts. I would start making copies (no collate or staple!) and have boxes full. I would transport boxes home, head back over to the tax corporation office, and back home, back and forth all day. It must have looked like a giant scam or couple of fraudsters stealing stuff!

My mother, the artist

Of course, this was part of the investment. My mother, the artist, had the mind of an artist as well. She saw colors when the only color I saw was green. I remember her saying, “You shouldn’t spend money on copies, then you won’t have any money for college!” I couldn’t help but laugh. At this rate, I would never go to college, after all, what would be the point? They would take 4 years of my life and $20,000 and give me what? A job that paid $25,000 per year if I’m lucky? No thanks! I had bigger plans, plans that didn’t rely on anyone but myself.

After my mothers suggestion that I shutter the business, I stopped sharing all of the details with her. I had recently turned 18 and would be graduating in just a couple months. After graduation I would get my own place and be able to store copies in all of the bedrooms and not have to sleep between boxes in my bedroom. There were days I had so much stuff in my bedroom, I couldn’t stretch out to sleep! In fact one night while asleep, I stretched out my legs and papers landed all over me. Of course they were in a specific order and I had to get up at 2:00 a.m. and spend 20 minutes resorting the papers so I could ship them before school.

On My Own, Finally

Ian Leaf on his yacht off Catalina Island.

I loved my mother and wouldn’t have changed anything, but a man with over $200,000 in the bank needs some space. My mom suggested I should rent an apartment so I could see what it was like and come home if I was lonely. I took her advice, but rented a house instead. The tax man whose office copier I had been using offered a rental house that he had. It was a month to month lease which worked out perfectly. He was also brokering the sale of my company at the same time and the house was close to his office, it was just about perfect.

Until One Day…

This is how most stories end. Everything was going so well…until it wasn’t. I’m happy to say that isn’t how my story ends. I sold the company and when I did I made a lot of money. The company that bought it expanded into many other industries and they kept me on as a consultant for 6 months paying me $50,000 per month. I was required to drive down to their headquarters about 4 hours away and spend one week per month with them. During that time I would help them brainstorm new ideas and since I had signed a non-compete agreement, I was happy to help them succeed where I left off. The power of their corporation was eye opening for me. Seeing how a well oiled machine like that worked was worth all the money I had made. It was an education that college never could have given me. Towards the end of the 6 month agreement, I was spending more time than was obligated. I was learning from the president of the company who was very successful and in his early 40’s.

Thomas Andrews, My New Mentor

A 42 year old man who has millions of dollars and broke parents is something that caught my attention. It was similar to my situation. My parents weren’t broke by common standards, my dad made good money, but they were still upper-middle class. They lived in the suburbs and would need my dad’s pension to stay solid if he were to ever retire.

Thomas Andrews was different. His parents were the same as mine. “Regular working folk” as he called them. He was different, not “working folk” and certainly not “regular”. His mind worked in ways that I couldn’t keep up with. He had a plan and people in place to make his plans happen. He was good too. Even being good, he wouldn’t always come up with a winning plan.

“Winning Requires Losing, Sometimes” – Thomas Andrews

I learned a lot from Thomas and was grateful to him for taking me under his wing. After my agreement ended, I stuck around. I didn’t have anything to do, plenty of money and was eager to learn. My non-compete protected him and he didn’t see my as a threat, but an ally. I think he could sense my motivation and passion, I was a stand up guy and he knew that from all of our time together.

One day Thomas bought a company as he was wont to do. This company was a little different as they were loaded with physical equipment and also loaded with debt. About 6 months after buying the company, it had failed to make a profit and Thomas had to sell off the equipment and book of clients for 25 cents on the dollar for what he had paid. He lost more money on that deal that I had earned in all my life!

With a Rolls Royce after a garden party.

His advice to me is something I still remember to this day. “If you’re going to play a high stakes game, and there is no better game to play, remember that you can’t win every time. The best poker players, the best pitchers, the best quarterbacks, the best CEO’s, the best presidents, all of them will lose, but they will win more than they lose. Winning requires losing, sometimes. If you find yourself losing more than you win, or if you find yourself losing bigger than you win, you’re not cut out for the game you’re playing. The fish are too big in this pond and you need to humble yourself, and play in a different pond. Don’t take this as an attack, but realize when you’re outmatched and make a strategic withdrawal, don’t let you pride force you to go all into a battle you can’t win. Chose to live and fight another day, in another place, in a smaller pond.”

Wow, I was blown away. Thomas gave me advice that couldn’t be learned, couldn’t be taught, but had to be lived and I had the chance to stand right by him and learn it first hand.


Between Thomas’ advice and my experience I’ve learned where my pond is. I’ve focused my efforts and endeavors and typically only make a bet I know I can win. These bets are never based on luck, they’re based on skill and my personality. I don’t like to be overdrawn or overstretched therefore I don’t overreach. If the pot is big but I can’t adequately handle the work, that’s a fish someone else can have, it’s not worth the risk.

That’s my history, hope you enjoyed the read!