Josh Roseman
About Josh

Hi, I'm Josh.

30 years in finance. And I still had to figure out how to manage my own money the hard way. Lots of mistakes. A lot of learning. Eventually, a simple system that actually worked.

I spent my entire 30 year career inside finance, and still had no idea how to manage my own money.So I built something better.

Ivy League education. MBA. And in my 20s I still had no clue. I tried everything. Stock tips. "Top rated" mutual funds. Listening to the so-called experts. It all felt like guessing. Meanwhile, fees were eating my returns and I was spending beyond my means without realizing it.

It was all more or less "fine" until 2008 hit. And then it caught up with me in a hurry.

We lost our home. Took on debt. Had to make major cutbacks.

It was a massive wake up call. And it forced me to do something different to make sure nothing like that ever happened again.

I used my finance background to create something real. I simplified everything. Built a system with clear structure, real goals, and intentional investing. One that tracks the market, minimizes fees, and actually fits real life.

That system has now worked for nearly 20 years. Our net worth has grown more than 10x since then, without ever paying an advisor.

And we did not do it by saving every penny. We did it while raising two kids and actually enjoying life along the way. Travel, concerts, sporting events, a home we love.

Because when your money is working the way it should, you actually have more of it. More for today and more for tomorrow. And more importantly, you stop worrying about it.

What I learned

Most people don't have a money problem.
They have a clarity problem.

The industry either gives you complexity from advisors trying to justify ongoing fees, or generic advice that does not translate into a real plan. For high earners especially, neither works.

That's why I created Living Freely. Through The Simple Investing Method™, I help high earners simplify their finances, take control of their investments, and build a clear plan they actually understand and trust.

Background

Three decades of
real world finance.

The same institutions that train Wall Street analysts trained me. The mistakes I made with my own money taught me everything else.

MBA, Real Estate Finance
UCLA Anderson School of Management
BS, Business & Finance
Cornell University
Senior Underwriter
Wells Fargo, Real Estate Capital Markets
Senior Vice President
George Smith Partners
Associate
Stonewater Partners, Private Equity
Founder & Coach
Living Freely, LLC
Josh outside
Why I do this

A coach in your corner.
Nothing to sell.

I do not manage your money. I do not take commissions. I do not sell products. I teach you the system I built for myself after 30 years of watching the industry profit off confusion.

When you finish coaching, you walk away owning the knowledge. Not renting it from someone with a fee meter running. So you can focus on living your life freely while your money does the heavy lifting.

If that's what you've been missing,
we should talk.

Free 60 minute strategy call. No pressure. No pitch.

Book your call