Founder

Portrait of a smiling man with short gray hair, wearing a dark suit jacket and light blue dress shirt, standing against a plain light-colored wall.

Get to Know John Thompson Jr.

Founder, Acertado Investments | Fee‑Only Fiduciary | First‑Generation Wealth Builder

I founded Acertado Investments because I know what it takes to build wealth from the ground up. I’m a first-generation wealth builder — someone who didn’t inherit a financial roadmap, but created one through discipline, education and intentional decision-making.

I grew up in the rural Midwest, far from the world of institutional investing. Nothing about my background guaranteed financial success. Every step — from earning scholarships to studying abroad to building a career in investment management — was the result of deliberate choices and long-term thinking.

That experience shapes how I work serve clients today. I understand the pressure, the responsibility, and pride that come with being the first in your family to build real wealth. And I know how transformative the right financial decisions can be.

Why I Serve First-Generation Wealth Builders

People like us do not take wealth for granted. We build it intentionally. Through discipline, sacrifice, and a commitment to living below our means.

My clients are typically individuals who:

  • Did not inherit a financial playbook

  • Want to create a better financial life than the one they started with

  • Value structure, clarity and long-term thinking

  • Want a partner who understands the stakes and the journey

If that’s you, we’ll work well together.‍

This focus is not a marketing angle — it’s lived experience. It’s why Acertado exists.

Institutional-Grade Experience, Personal Perspective

Before launching Acertado Investments, I spent decades managing institutional portfolios for major corporations and global financial institutions. My roles included:

  • Principal & Senior Investment Strategist, PGIM Quantitative Solutions, Newark

  • Partner & Head of Wealth Management & Investment Solutions, Aon, Chicago

  • Senior Vice President & Portfolio Manager, Morningstar Investment Management & Ibbotson Associates, Chicago

I advised on billions of dollars for insurance companies, private banks, broker‑dealers, pension plans, endowments, and asset managers — applying academic research and evidence‑based frameworks to real‑world investment decisions.

Today, I bring that same disciplined, institutional‑grade investment process to first‑generation wealth builders who want a professional who want a professional, repeatable approach — not guesswork or speculation.

City skyline in the evening with tall buildings under a purple and pink sky. One World Trade Center is visible among other skyscrapers.
A waterfront view of Chicago skyline at dusk, with tall buildings including the John Hancock Center in the distance and a curved concrete pier in the foreground.
A historic brick building with white columns and a dome partially obscured by several large trees with spring foliage, under a clear blue sky.
Night view of the Chicago River looking toward the University of Chicago's Booth School of Busiiness. A cityscape with illuminated skyscrapers, a river reflecting city lights, and a clock tower with a green and red lit top.
Montevideo, Uruguay and the General Artigas monument.

A Global Perspective, Rooted in Real Experience

My academic journey took me from the Midwest to South America, where I studied as both a Rotary Ambassadorial Scholar and a Fulbright Scholar. I earned an MBA in Finance & International Business and an MA in Latin American Studies from the University of Chicago.

I speak Spanish and Portuguese and have lived in Chicago, Hoboken, and now Fort Lauderdale, Florida.

These experiences taught me how different cultures think about money, risk, and opportunity — insights I bring to every client relationship.

Aligned Incentives, Transparent Advice

As a fee-only fiduciary, I am committed to acting in your best interest — always. And when appropriate, I invest in many of the same strategies I recommend. I believe in

  • Alignment

  • Transparency

  • Evidence-based decision-making

  • A disciplined process that keeps us moving in the same direction.

Let’s Connect

If you’re a first-generation wealth builder looking for a long-term partner who understands both the technical side of investing and the personal journey of building wealth from scratch, I’d love to talk.