$100 Million Dollar Entrepreneurs
Anthony Pompliano X Tom Sosnoff = Regular Guys That Did It
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Today’s edition is part of My Stories where I share vulnerable thoughts around my opinions in Finance.
Charts & Chit Chat will be the next edition coming out within a few days where I share Financial Data/Charts alongside quick takeaways that get right to the point.
After that is a weekly Video Post you can think of as a coaching call where I chat about whatever is most relevant over the last week.
For now, let’s get vulnerable.
Two of my favorite entrepreneurs on the internet are Tom Sosnoff and Anthony “Pomp” Pompliano.
Pomp recently had Tom on his YouTube Channel, which was interesting to me because Tom doesn’t make a lot of appearances on YouTube, and Pomp’s channel is not really a channel for option traders.
I’ve been watching Tom on the TastyLive network since 2013.
TastyLive is a Finance network that streams live content on their website during the day, where Tom and his friends banter about strategies in the market and what’s for lunch on any given day.
Mostly option strategies, and takeout from the West Loop in Chicago.
Tom and his trading buddies aren’t your normal desk traders though.
Tom was a former floor trader at the Chicago Board of Options Exchange in the early 80’s. By the mid-late 90’s he could see the writing on the wall that the industry was moving online, so he started building the first retail trading platform with a few of his trading buddies.
That platform was ThinkOrSwim, otherwise known as TOS.
Before TOS, it was basically impossible to trade options like we can today as a retail trader from home.
After working on TOS for 10 years from 1999 to 2009 he sold it TD Ameritrade for $750 million dollars.
2 years later in 2011 he started the TastyLive Network, streaming free content online all day. How the heck can they monetize that you ask?
Well, in 2017 he launched ANOTHER retail trading platform from scratch.
That’s the TastyTrade platform we know today.
They combined the media content with the brokerage, and they really cared about their audience along the way. Tom is one of the only people worth over $100 million dollars on Google that will answer an email from a Joe Shmo like you and me within 24-48 hours.
As long as they aren't too crazy of course. Don't send him your excel spreadsheet of daytrades to review.
They educated and entertained, cultivated an audience, and quietly built a trading platform catering to option traders like them which paid off big, for the second time.
In 2021 he sold TastyTrade to IG Group for over 1 billion dollars.
That’s billion with a B.
The man has almost 2 billion dollars in exits from building the same company from scratch twice.
It’s amazing.
I’m really jealous of all of that.
My dream job that no longer exists is to be a trader in the Chicago trading pits back in the 1980’s like Tom and his friends. A floor littered with alpha males who are given a license to steal as a market maker on the trading floor before computers existed.
You either got really really rich, or you lost absolutely everything because you were too leveraged and caught offsides at the wrong time in the market.
There was no inbetween.
It doesn’t get much cooler than that.
Trading in the pits.
The opportunity to make money and network with other rich people would set you up for life, like it did for Tom and anybody else who was able to stay alive in those trading pits.
I’ve heard Tom tell several stories of how Michael Jordan would hang with the pit traders sometimes, mostly to gamble on something like cards or golf.
One of my favorite stories is Tom was sitting courtside with a trading buddy at one of the Chicago Bulls games in the 1990’s. Jordan walked up to him and said, “I’m working right now so I can make as much money as you two clowns one day.”
It's pretty amazing to think these guys from the trading pits in the late 80’s and early 90’s were making more money than athletes like Michael Jordan.
Just for the right to stand in the trading pits you needed to “buy a seat” that would cost anywhere from $100k to over $1 million dollars depending on the exchange or market conditions. Then there were annual fees after that.
So if that “seat” cost $300k, that means some guy standing in the pit needs to make $300k for the year just to break-even. And this is in the 80's.
That makes for a lot of testosterone rolling around in that trading pit 5 days a week.
Usually you find an Uncle Jimmy or an experienced pit trader to buy your first seat.
Then you’re indebted to this Uncle forever like it’s the mafia.
You better pay back and make the family proud, or else you won’t get a room in the penthouse suite the next time the boys take a trip to Vegas for the weekend.
TastyLive
Tom starts the TastyLive show every morning with Tony “Bat” Batista, who he’s known since the trading pit days.
Bat is hilarious.
One morning on the show, a kind researcher from TastyLive asked Bat if he remembered any memorable breakfasts in Vegas from back in the day.
Bat rolled his eyes and responded with, “yeah, her name was Tina!”
Spoken like a true risk taker right there.
Him and Tom make a great duo on the show together.
Tom is very unorthodox with his thoughts and opinions, so an interview with him on “another platform” that isn’t TastyLive is always fun to listen to because he tends to confuse the person on the other side a lot.
Pomp
Pomp is top grade though, especially with his ability to lead a conversation and find ways to learn from it.
He’s 36 years old, and when I compare his life to mine I have to say I get a little depressed. He’s done so much and is only 3 years older than me. We had the same opportunities, and he excelled beyond belief with them.
Google tells me he’s worth over $50 million dollars, and some websites state over $100 million. It’s tough to trust Google on these things, but I’ll know I’ve made it when Google starts assuming numbers like that about me.
Those are almost Tom Sosnoff numbers.
Pomp played football and studied Finance at Bucknell University, and following that he served in the U.S. Army for a few years as a part of the military intelligence division.
When he got back from the Army he ventured off into a tech career.
He worked for companies like AOL, Facebook, and lastly Snapchat where he was a growth and product manager. He looked at data and figured out ways to increase the platform’s user base.
He didn’t stay at many of those companies long, and shortly after leaving Snapchat he co-founded a private investment company in 2018.
Morgan Creek Digital Assets. They have almost $2 Billion in assets under management today.
This firm focuses on cryptocurrency investments and asset management.
Today, Pomp has become one of the most outspoken advocates for Bitcoin that you can find on the internet. Not because he is a crazy Bitcoin loony like me though, but because he is really good at breaking down complex topics in a simple manner.
He really understands Bitcoin and blockchain technology, and uses his platform to educate others about the potential for digital assets.
You can find him on YouTube, Twitter, Substack, Spotify, CNBC — the guy is all over the place.
His work at Morgan Creek and his media presence established him as a prominent figure in crypto, and that branches off to trading, investing, and macroeconomics as well.
You find him around all types of people in Finance, from the degens to the suit and ties.
Today, CNBC introduces Pomp as the Founder and CEO of Professional Capital Management. To be honest I am not sure what the connection is there, if any, with Morgan Creek Digital.
This is just another sign that the guy keeps making plays, moving and shaking.
Pomp is someone I found around 2020, and he really made me feel more comfortable about making bigger investments in digital assets, primarily Bitcoin.
Being known as one of the main Bitcoin advocates on the internet, with $50 or $100 million in net worth per Google, a beautiful wife and newborn child, constant CNBC appearances, a network of the coolest people in the Finance industry, a football and Army background — and only 36 years old...
Pomp is kind of the man.
Just imagine what his empire looks like when he is 66 years old like Tom is.
These are two people that have been very influential in shaping my financial framework today.
They have a lot of similarities.
They both took a lot of risk in their lives, and still do.
They both are extremely confident in their financial frameworks.
They both use a network of people to propel themselves to the next level.
We can learn a lot from both of them.
In the interview, Tom made some really good points against passive investing in anything, even Bitcoin!
Tom notes that many have profited from passively investing in Bitcoin, but questions if they've learned anything of value in the process.
Even if it makes you rich, you don’t learn anything by buying and holding an asset, and then checking on it in 5, 10, or 30 years.
On the other hand — being an active trader in markets daily helps you become a better decision maker and risk taker. Trading helps us understand ourselves and our emotions better. This translates to other areas of our lives.
Learning to trade increases your emotional discipline faster than passive investing does.
I am constantly told that I have a calm or “chill” presence, even during hectic times. That is 100% because Finance, Trading, and Investing have been a huge part of my life for the last 11 years.
I’ve learned control over my emotions. I’ve increased my emotional discipline. I’ve become better at taking accountability for the risks I take, and I look to grow from failures rather than complain about them or blame others for them.
I am at peace with myself.
Tom has had an incredibly positive influence on my life as I was first learning how to trade and take risks in markets and in life.
If it wasn’t for finding Tom and TastyTrade back in 2013, I would not have found Sky View Trading and the job I have with them today, which I love.
I would not have had the courage to quit my comfy accounting job and pursue my trading obsession either. Learning to trade at 22 years old was the best thing I ever did in my life.
Pomp has been very influential for me too, but for different reasons.
Pomp introduced me to the macro side.
That was the other side I was missing.
Macro was boring, stupid, and didn’t matter — until Covid and the massive amounts of money that were printed to stimulate economies around the world after a global lockdown happened.
Pomp isn’t really a macro-guy, but the intersection of Bitcoin and macro started to grow a lot stronger in 2020 when Bitcoin pumped massively as the US government was printing money to stimulate the economy.
Learning more about Bitcoin forces you to learn more about money, which forces you to learn more about macro, which forces you to learn more about the global economy.
They don’t teach you this in school though.
Or I guess they try, but learning about Macro is boring when you’re not also learning about money too. Bitcoin makes learning about macro more fun.
At least, for me.
Understanding the history of money, what money has evolved into today, how it is created or destroyed, and what affects that has on the global economy at large is a complex topic we could always learn more about.
Especially now in this current era of running higher fiscal deficits than normal as a percentage of GDP, especially for “non recessionary” periods.
So while you don’t learn much from buying and holding Bitcoin, it certainly leads you down some rabbit holes that could help create a stronger financial framework over time.
Finding Pomp led me to finding so many other people on the internet in the world of macro.
I don’t use any of that macro stuff for the trading I do, but having an understanding of the macro stuff alongside the benefits of being a shorter term trader gives me the confidence I need to set up my net worth in a way I am extremely comfortable managing on my own.
I make the decisions and I live with the results.
I manage my own balance sheet, the same way Central Banks around the world try to manage their balance sheets — hopefully I do it with less debt and more assets of course!
As I learn more about how money is being debased and the trend that different Central Banks around the world are going in, it helps give me more confidence in the longer term investments and allocations that I choose for myself.
Pomp has led me to finding people like Raoul Pal, Lyn Alden, Michael Saylor — and those 3 people led me to finding a floodgate of all their friends, lookalikes, and enemies on the internet.
This allows me to hear both sides of the story from really smart rich people, track their narratives and results over time, and make the best decisions for myself along the way.
Being a short term trader helps me shift through these macro narratives, look at the incoming data, and find confidence to bet on the trends I can see unfolding over the long term.
This has helped increase my confidence to invest more in technology and Bitcoin over the years, which as of now have been outperforming most asset classes over recent history.
Of course, Tech and Bitcoin could crash any day now and I might wish I used that money for trading more 0DTE options instead. In any event…
It’s helped me find true confidence in the fact that saving in dollars is a suckers game over the long term term.
My parents generation lived by the code “cash is king,” but it’s not anymore.
Cash is trash.
Times are changing, and these smart rich people on the internet have helped me identify the changes in the world and that I need to make in order to prosper.
It's not just about Tech or Bitcoin either -- it's more about trading cash for assets over the long term.
Passively investing in the market index sounds really boring and stupid, until you realize that in the last 50 years the US Dollar has lost -52% of its purchasing power while the S&P 500 has an inflation adjusted return of +972%.
Again, cash is trash.
I’m lucky I found both Tom and Pomp when I did, and all the roads they both have led me on along the way.
I’m a risk taker.
I live with my results.
I make quick decisions.
I have high emotional discipline.
I am trained in the option markets.
I have experience with digital assets.
I am learning a ton more about macro.
I am thinking bigger and like an entrepreneur.
We all can’t be Tom or Pomp, but today we have the internet to help us find folks like them and tap into their thought process.
That wasn’t really a “thing” 10 years ago. Youtube is only 19 years old, and Finance YouTube didn’t start blowing up until 2020.
So as depressed as I might be when I compare my accomplishments to theirs — I know we’re all just out here jogging our own pace and playing against ourselves.
All we can do is use the tools around us at the time to become the best version of ourselves along the way.
Take risks, take accountability, and take notes.
And once you are ready, you’ll take off.
Here’s to $100 million.
LFG.
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Disclaimer: These are not recommendations and I am not a financial advisor. These are just my two cents, or two satoshis as the kids say. Remember to do your own homework before making any financial decisions. Also, keep in mind I usually have some personal investments in the things I discuss.
Any friend of SOS and Tony is a friend of mine. Fantastic article!
Amazing listening, always interesting hearing other people’s stories!