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Jason Mickool | He Got Fired From Every Job… Then Built a $130M Company artwork

Jason Mickool | He Got Fired From Every Job… Then Built a $130M Company

School of Hard Knocks Podcast

September 30, 2026

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Speakers James, Jason Mickool, Josh, Jack

TopicsBusiness

James (0:00)

Jason, I want to talk about money.

Jason Mickool (0:01)

I want to dive into it right now. You're broke at 500 grand.

James (0:05)

You consider them broke?

Jason Mickool (0:06)

I consider them broke.

James (0:07)

So at what point financially does somebody have money?

Jason Mickool (0:10)

If you have a net worth 250, you can kind of do whatever you want.

James (0:13)

250 what?

Jason Mickool (0:14)

No.

Josh (0:17)

So what about the 25 million?

Jason Mickool (0:18)

You could have a bad summer and blow 25 million.

I get paid quarterly today. I think today is a payday for me. It's like $4.9 million.

Josh (0:28)

Decent payday.

Jason Mickool (0:30)

Yeah. 90 days later. If I was young again and I was telling people, what should I do? Don't ever go work for a b****.

Jack (0:37)

Your wife puts you to be an entrepreneur.

Jason Mickool (0:38)

My wife is a very kind, amazing human being. And I was trying to get a job. I was looking for a job. This fate looks comes over her face and she says, can I be honest with you? And I said, yeah, of course you can. I would expect nothing else. And she goes, you're just being a b****. Well, let's just start. You do it yourself.

James (0:53)

Mr. Jason Mickool. This was an incredible conversation. This is a good conversation or what?

Jason Mickool (0:57)

I loved it. The only way to true generational wealth, as you put it, James, is to.

James (1:05)

What's going on everyone? Welcome back to the School of Hard Knocks Podcast. I'm James. I'm here with Jack and Josh. And we have an incredible guest for you all today. An expert on building generational wealth, Mr. Jason Mickool. You sold a part of your company a couple of years ago for about a hundred million dollars. Is that correct?

Jason Mickool (1:21)

Yeah, just about, right? When it's all combined and everything, it's probably in the 130 or so amount. I still own 20 percent of it.

James (1:29)

Jason, did you come from a rich family?

Jason Mickool (1:31)

No, sir. Did you come from a rich family?

James (1:33)

Not really.

Jason Mickool (1:35)

Military parents. Oh, military parents.

My dad was a pastor. And before that, my grandfather was a Lebanese immigrant, came across on the boat, and built a boat business, lost it in 1980 We literally ate tomato sandwiches.

James (1:51)

What were you initially exposed to the fact that you could build a hundred million dollar company? Because correct me if I'm wrong, right? And for context, you're one of the biggest financial planners in the entire world. You're managing hundreds of millions of dollars for some of the wealthiest people alive. So I want this podcast to serve for the people watching as a blueprint on how to build generation of wealth. Can we make that happen today?

Jason Mickool (2:11)

I think so. I think so. It's clear.

I'm not a financial advisor today. I own a financial advisory platform, which is different. We have 800 financial advisors in 28 locations and 17 states. I'm across the country and my wife and I started it from scratch.

James (2:28)

But let's talk about, I want you to take me back to the exact moment that you realized that you were exposed to the fact that it was possible to create a nine-figure business and ultimately build a nine-figure net worth.

Jason Mickool (2:39)

I didn't know that that was actually possible. I dropped out of college. Did you finish school?

James (2:43)

I did finish school.

Jason Mickool (2:44)

You did, right there for you. Well, that guy did right there. I'm going to jump out right there. Go on.

Jack (2:47)

Thank you.

Jason Mickool (2:49)

I grew up in a shitty town in a new Bedford area, Dartmouth, Massachusetts. I always say if this is the Cape in the Boston, that the armpit would be where I grew up.

James (2:59)

The armpit.

Jason Mickool (3:01)

Most of my friends are great people. I still hang around with them all the time, but it's a very blue-collar community. Never liked school, never liked passing exams or taking exams. I like to work. I like to make a buck. If I could make a buck, if I could wait tables or bartend or cut a lawn, that was where my passion was. I dropped out of school, so I didn't think I had an opportunity to get into finance. Took an entry-level job and doing new business processing. My dad went from the cloth to selling boats. I used to sell boats part-time, so I had a little bit of sales experience. I got lucky once and found myself introducing to a financial advisor who took a liking in me and taught me the way to get my licenses. I went and got my licenses. I went into sales, and then that was my rock. I wasn't going to give that up. I'm like, all right, this is my opportunity to compete with people at a different level.

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