A Message To My Generation

I’ve been fired or laid off from every job I’ve ever had. No joke, I’ve been fired from delivering pizza, stringing tennis racquets, being a boating instructor at a summer camp, I was laid off from Geller Capital in early 2009 after David got sick and wound down the firm, fired from the private wealth management firm I worked at for a short time after that, and I was (technically) fired from StockTwits in March of 2011 after Howard told me that I was “an entrepreneur”, and it was “time to go make some real money”.

Every time I was fired, I went back to working for myself, and ended up loving it. I lived on a girlfriend’s couch for a few months and ate ramen noodles one time, but I loved it.

As a kid I used to sell painted rocks, shells, other arts and crafts, and even once put my little 5 year old sister out in front of the wagon with a sign saying that we were donating all money to the ASPCA, we wanted a cat, we raised $250 in an afternoon. When I got older I leveraged my notoriety as a great tennis player to teach private tennis lessons for $50/hour, it beat delivering pizza for $4/hour, or camp for $12/hour. When I was fired from the private wealth management firm, I formed Surfview Capital to build my own asset management firm which I successfully ran for 2+ years with great returns and growing assets. And when I got fired from StockTwits, I started Estimize where I’m able to execute on several different ideas I had while at StockTwits which were never going to get built there.

Until recently I didn’t understand the definition of entrepreneur. Building businesses and making money on my own was always just something that I did when I was forced to, I didn’t think of it as a job or a career. Until recently I didn’t understand the idea that being an entrepreneur permanently wasn’t something that should be looked down upon.

The story of why it took me 25 years to figure this out says a lot about my generation, the pain and disappointment many of them are feeling right now, and why they need to start thinking differently.

I was raised in a town about 45 minutes north of New York City. The Chappaqua public school system is often ranked top 10 in the nation, if you didn’t get into an ivy league school, a top northeast liberal arts college, or Michigan, well, you just didn’t. 33 of my graduating class of 320 went to Cornell. I grew up in what will eventually be seen as the epitome of everything that went wrong regarding the way upper middle class parents raised my generation, and how many Millennials see the world today.

They didn’t keep score in my little league baseball games until I was 13, lesson, everyone’s winner, no one is better than anyone else.

In school they never posted grades for the whole class, everything was private, lesson, school is not a competition and everyone is “smart in their own way”.

I once found out what another student in my class received on an 11th grade social studies paper, I read the paper, then went to the professor and confronted him over our grades. The answer I received floored me, he said that the other student deserved a higher grade not because his paper was of better quality, it wasn’t in any way, but because that student had “worked hard” and deserved recognition for his perseverance. I asked him if a college we were both applying to would take our respective grading curves into account, he told me to get out of his face.

We were indoctrinated into being good team members, to work well in groups, to collaborate. Leadership was shunned for fear that it would promote certain students and lower the self esteem of others.

On sports teams everyone was given equal playing time, because once again, we didn’t want to hurt anyone’s feelings.

Our parents and teachers attempted to build bubbles of fairness, equality, and an “effort is what counts the most” environment.

And most important, we were taught to follow the rules, to work within the system. Our lives were scheduled with activities back to back to back. School, homework, 5 different clubs, 3 varsity sports, 2 community service commitments, not a minute was left free.

The system was meant to lead us towards one thing, getting into a great college.

I don’t blame my parents, teachers, and coaches for having this view. Many of them were the first in their families to go to college, and that was a major accomplishment back then when a college degree meant a lot. I don’t blame them for coddling us from the real world, for trying to institute a sense of fairness, for teaching us to work with each other. It’s not their fault.

But it really screwed us.

My generation, more than any other generation before it, was raised in such a way as to be completely ill equip for the real world, especially the real world we find ourselves in today. We were raised in systems meant to be “fair” when the world is anything but. We were given instructions on how to succeed as children and told not to deviate from them when the real world comes with no instructions and requires you to figure out how to succeed on your own. We were taught to work together at all times, that no one is a leader or a follower, when in reality everyone is out for their own good. We were taught that everyone was equal and equally smart in their own way when the reality is that there are dumb people in this world. We were taught that effort is what matters, when in fact results are what matter.

Then we were handed the worst labor economy in 80 years, where labor is being massively devalued by both globalization and technological innovation. Our college degrees are worthless because everyone has one, and because most of us (save for the engineers and mathematicians) were taught useless academic crap in college which has little to no practical purpose when it comes to the labor market. We went into interviews boasting the ability to dissect Shakespeare and were asked to run a pivot table in Excel, we flunked. Our institutions of higher learning failed us, miserably, with their inability to provide an education that was relevant to our goal, getting a job. What did we get? How about enough student debt to weigh down a whole generation for the next 30 years.

On top of it all, our parents who run the government refuse to cut their own entitlements and continue to steal from future generations in just about every way. They use government money to bail out failing industries which keep their generation in business retarding the ability for younger innovative individuals to build new industries. Yes, they fought hard to change our world, to make something of themselves after their parents had lived through some very tough times, but that doesn’t excuse their selfishness.

We got a raw deal all around.

So what. Life isn’t fair, something my generation needs to learn, in a hurry.

The message that I have for my generation is this. There is no better time than now to build something of your own. We played within their rules and look where it got us. Their system is broken and their ideals where noble but destructive to us. It’s time to grow up, be realists, stop asking for things from the system and start taking them.

Stop thinking that someone is going to give you a 60K/year job and start finding ways to lower your costs and make build your own businesses. Our parents owned too much stuff, we don’t need 90% of it. The things you buy should be experiences, not physical goods. Don’t let your possessions own you, own what you can pack in a few suitcases, and don’t own things you can borrow or rent.

Utilize the spare capacity in the assets you do own to make extra money. If you rent an apartment, stay at a friend’s place a few nights a month to make some extra cash by renting on Airbnb. If you own a car, make some extra cash by renting it on Getaround. If you own a box of tools, allow your neighbors to rent it from you on NeighborGoods. There are a million ways to simply make more money without someone else having to hire you. You need to learn to live with less income.

Don’t conform to the idea that you need to settle down in the suburbs and get married by 30. This was our parents’ dream, it’s not ours, don’t pretend it is.

Technology has given us a great gift, the ability to pay for less and make more by sharing. And this enables the most important thing, the ability to build your own businesses.

Counting on other people to hire you is the last thing you should be doing. It’s time to be resourceful, to create things that people want. You have nothing to lose, you can work at McDonalds for $8/hour or you can start your own business, struggle for yourself, and be successful for yourself. Or fail, fail again, fail again, and then succeed, you have nothing to lose, so why not. You have nothing to live up to, especially the philosophies of our parents, so don’t be scared.

Take the time to learn new skills through Skillshare, learn to develop software through Code Academy, or simply go through the basics on Kahn Academy.

It’s never been cheaper to start a tech company and there’s never been more upside. You can make things and sell them on Etsy, or make food and sell it on any one of the different artisan food platforms. You can even pick up extra cash by doing things on TaskRabbit while you build your business.

Stop waiting for the broken system to give you the life they said you’d have and start taking it for yourself.

As a child my father constantly berated me by saying that I didn’t believe the rules applied to me. He begged and pleaded with me to play within the system. I was a natural rule breaker and had a great disdain for authority, particularly hypocritical authority. I consider myself lucky in this regard.

And while I grew up in overachievementville, I was lucky to receive some decidedly different lessons as a child. Without knowing it my parents taught me the value of being an entrepreneur as a child, always pushing me to go and sell things to make money for the stuff I wanted. Ironically as I got older they scoffed at getting fired from camp so that I could teach tennis lessons.

I was a great baseball player, but at the age of 12 I quit to play tennis and hockey full time. Tennis, unlike other team sports, didn’t offer the ability to hide behind your team mates. You either won or you lost, it was all on you. I learned hard lessons about getting out what you put into something as I made my way through the junior regional and national circuits. This broke down many of the horrible ideas I was taught in school.

Instead of playing hockey on a school team I played on a regional travel team. Playing time was merit based, and leadership was an extremely important characteristic. I learned how to lead people on the ice.

I feel lucky that my general disposition made this economic transition easier for me than it most likely will be for many other people. And I don’t kid myself about the fact that while I did not grow up the wealthiest, I was given ever opportunity one could ask for.

I don’t believe in equality of income or assets, but I do believe strongly in the equality of opportunity.

I feel lucky that I’ve been fired so many times, and that it has finally registered with me that I don’t need to rely on anyone else to give me what I want.

My generation can choose to feel sorry for themselves now, or they can capitalize on the huge opportunity in front of them. They can wait around for the old paradigm to completely fall apart and get dragged down with it, or they can choose to build their own futures. It’s all within their reach, no excuses.

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