How to make a million dollars if you have the guts.
Three easy steps.
1. Go to companies that are not public yet but are looking for a liquidity event. That can mean going IPO or being sold.
This is tough for most people because they may not live in an area where there are a plethora of pre-public companies. If you live in Small Town USA, there may be several chain stores on main street but otherwise most businesses are privately owned and will be either be passed on to someone in the family or be sold to another entrepreneur. You can work for these type of companies for you whole life and just make wages. If you are lucky and understand the business, you might get a chance to buy the company.
I have a saying. If you’re a plain’s Indian you need to go where the buffalo roam. If you want to work in pre IPO companies you need to head for the technology centers on the West Coast, East Coast or down into Texas (Austin I think). But you need to go where there are many of these companies and more coming. I live in the SF Bay Area. Will I ever move? Not as long as the buffalo are here. I have worked for 18 companies in my career not including all the companies I contracted for. I have done 4 pre IPO companies. Made money at two of them. There are going to be some of these places that don’t make it. You have to be able to shrug and move on. Your goal is to make money on stock and enjoying work is a strong second (but it is second).
2. Make sure you get stock and plenty of it.
You live on your base and bonus but you make a million on equity (stock!!!!!). It is usually high level exec’s that make bonuses that might get a worker past a million and more. But for us worker bee’s stock is the answer. The CEO of Cisco’s administrative assistant made more than a million when the company went public. You don’t need to be an exec. Most people focus on title, salary and bonus when looking for a new job. I was the same for much of my career. Then I began to realize that a whole lot of the extra cash I had in the bank was due to selling company stock options. Finally I began to look for an opportunity where I could get a decent stock package that gave promise for a big hit. Once I decided to go in that direction, my whole perspective changed. At the time I was a director at a big public company that I liked and in a job I loved.
But when the opportunity came, I moved without a second thought. I was recruited heavily by a startup for a director level job. I knew I needed to be a VP to get the stock I yearned for and so I focused on title and stock. They kept coming back to me offering me more base salary and sign on bonus. Finally I told them unequivocally that the job had to be a VP and I wanted a certain amount of stock.
I WAS PREPARED TO WALK AWAY! To get what I wanted, I had to be able to do this. I was nice about it but without a certain level of equity, the job wasn’t worth moving for.
Finally they came around and lowballed me on base (I didn’t care) but gave me the title and equity package. three years later I cashed in the stock 6 months after we went public. I had what my father used to call GO TO HELL money. I never actually said go to hell, but you get the idea. I no longer had to work anyplace or for anyone I didn’t want to work for. It was liberating.
3. Be willing to move on.
Sometimes a job is just a bridge job. You make or don’t make your $$$ killing and you move on to the next opportunity. Your goal to put enough money (whatever that amount is) in the bank so you are free to work or not work. A friend of mine recently said, “All jobs are bridge jobs.” I am totally in agreement. I don’t look for lifetime employment. I am not interested in being a zoo animal waiting for my daily feeding. I like hunting for myself. I know that this is not for everyone. And trying to make a whole bunch of money isn’t for everyone. They would rather try to win the lotto. Of course the odds are better that you are going to get struck by lightning than win the lotto. Actually the odds are only marginally better playing than if you don’t play at all. That should tell you something.
I am not against lotto by the way. By all means play it. I choose to play job lotto. Once I set a financial goal which was a very humble million dollars, I set out after it the only way I knew how. Changing jobs often enough to make some extra cash on stock.
My first pre IPO came up a bit short but I still made around $100K. My second public company which was hotter than a pistol when I came on board, came up empty for me. They did a silly acquisition that dragged them to the bottom of the Pacific. Mariana Trench I think. The third was another public company which had been becalmed and then took off and got hot. I made around $250K on that one. Then I moved to a pre-IPO and went well over a million and change. Of course I had to pay taxes but one day I looked at my bank account and realized I was a poor man’s version of a millionaire (BUT, I WAS A MILLIONAIRE). It had taken 4 company moves in nine years and it had taken almost 12 years to make my million. It might have happened faster but I really liked company number three and hung around longer than normal.
It took me a long time to realize how this worked. I was slow on the pickup. I wanted freedom and got a version of it early on in my life by needing very little money. My formula was simple.
Live cheap
Work
Take time off
Live cheap
Work
Take time off
The problem was that I always had to come back to that one nasty word.
WORK
Not that work is bad but I pretty much was a magnet for bad jobs and bad bosses. I just wanted freedom from those two things.
Once I was married and we had a kid, a mortgage and car payments I was trapped into thinking of other ways out. So when I was unhappy I would just change jobs for another job. What I call job-jobs. You work to pay the bills. They have you by the short hairs. Then I wanted freedom from that. But I couldn’t take time off moving wasn’t getting me anywhere. It was a crap shoot with companies and bosses but finally I decided I needed to make this strategy of moving work for me financially. That when I became THE MERCENARY!

This meant I was a professional. Not like other people who think professional means that they get all sorts of accreditation’s and recognition from peers (read..other zoo animals). Yeah, I worked at doing my job better. I wasn’t there to short change those who elected to retain my services. And yes, I liked to mix it up a bit. But the truth was that I was in the game for a big strike. Not Trump big. I am not a comb-over type of guy anyway and admittedly I don’t play at that level. But I liked moving, fighting the battle and moving on. That’s what a mercenary does. That became my strategy. If there wasn’t the promise of some real coin at the end of the expedition then I moved on. I won some and lost some. I accepted this as part of the game.
