5 Wealthy Military Figures Worth Studying

These five turned what they built in uniform into big second careers. Study the choices they made along the way, not the dollar figures. For each one, there's a move you can copy at any rank.

David Petraeus

After retiring as a four-star general, he led the CIA, then joined the investment firm KKR in 2013 and became a partner a year later. He chairs the KKR Global Institute, which studies geopolitics for the firm, and KKR's Middle East business, and he sits on corporate boards.

The move to copy: he didn't sell "leadership" in general. He sold one specific thing he knew better than almost anyone, how the world's hot spots work, to people who needed it. Ask yourself what you know that a civilian company would pay for.

Colin Powell

The late Powell went from an ROTC commission to chairman of the Joint Chiefs of Staff and then Secretary of State. After government, he built a second career in speaking, writing, and corporate boards on decades of earned trust.

The move to copy: reputation compounds like money does. Every evaluation, every reference, and every promise you keep is a deposit. The payoff comes years later, when people you worked with vouch for you in rooms you're not in.

William McRaven

The Navy SEAL admiral who oversaw the 2011 raid that killed Osama bin Laden commanded U.S. Special Operations Command, then led the University of Texas System as chancellor from 2015 to 2018. His 2014 commencement speech about lessons from SEAL training passed 10 million views, and the book built from it, Make Your Bed, became a #1 New York Times bestseller.

The move to copy: he took lessons he'd learned the hard way and packaged them so other people could use them. Writing down what you've learned, and teaching it, is how experience turns into something that keeps paying you back.

Robert McDonald

A West Point graduate, he served five years in the Army with the 82nd Airborne and earned his Ranger tab, then left as a captain. He spent 33 years at Procter & Gamble, the last four as chairman and CEO, and then served as Secretary of Veterans Affairs from 2014 to 2017.

The move to copy: he didn't stay 20 years. He left after five and started over in business, near the bottom, and it still worked. A short enlistment or a single contract is enough to build on.

Wesley Clark

The retired four-star general, who served as NATO's Supreme Allied Commander, went on to business and a 2004 run for president.

The move to copy: the relationships you build in uniform travel with you. The people you served with end up in companies, agencies, and boardrooms. Stay in touch with them.

The enlisted example: Bob Parsons

All five above were officers. Here's proof it works from the bottom rank too. Bob Parsons enlisted in the Marine Corps in 1968 and went to Vietnam as a rifleman, where he earned a Purple Heart. When he got home, he used the GI Bill to go to the University of Baltimore and graduated magna cum laude. He started a software company, Parsons Technology, with $40,000 and sold it for $64 million in 1994. Three years later he founded GoDaddy, and in 2011 he sold most of it for $2.3 billion. He gives the Marine Corps credit for everything he's accomplished since.

The move to copy: he treated the GI Bill as a launch pad. An education benefit you earned in uniform can be the first investment in whatever you build next. If you haven't used yours yet, start with How to Get the Most Out of Your GI Bill.

What these paths have in common

Different branches, different ranks, different careers. The same three things show up in every one:

• A skill civilians recognize. Strategy, logistics, operations, software. Something a civilian employer can put a price on.
• A reputation that traveled. Every one of them left with people willing to vouch for them.
• Using what they'd earned. The education, the network, and the credibility from service, put to work on purpose.

Start while you're still in

You don't have to wait for your last day to begin. A few free places to start:

• Your branch's COOL site. Credentialing Opportunities On-Line matches your military job to civilian certifications and licenses, and depending on your branch and eligibility, it can help pay for them. Start at the DoD COOL portal.
• A mentor. American Corporate Partners pairs post-9/11 veterans, including Guard and Reserve with 180+ days of active duty, with a corporate mentor for a free, yearlong mentorship.
• VA career counseling. In your last 6 months of service or your first year out, VA's Personalized Career Planning and Guidance gives you one-on-one career help for free.
• A civilian resume. Write down how many people you led, what you were responsible for, and the results, in plain words with the acronyms cut.
• Your reputation. It's the one asset you're building every day whether you mean to or not.

Pick one this week

Big second careers get built one small move at a time. Pick one of these and do it before the week is out:

1. Look up your job on your branch's COOL site and write down one certification that matches it.
2. Send a short message to a leader you respected. Tell them what you're working on and ask one question.
3. Rewrite one line of your evaluation or resume in civilian terms, with a number in it.
4. Check how much of your GI Bill you have left, and decide what you'd use it for.

I'm doing a version of this myself, building a cybersecurity career alongside my Guard service. Nobody on this list waited until they were out to start. What I've learned along the way is in 10 Lessons That Took Me a Decade to Learn.

You don't have to make general for this to apply. The discipline, planning, and leadership you build in uniform carry into whatever comes next, at any rank, if you build the version of those skills civilians recognize while you're still in. For the money side of each stage, see The Right Money Move at Every Stage of a Military Career.

Sources: KKR, David H. Petraeus; Hachette, Make Your Bed; University of Texas System; Robert A. McDonald; Bob Parsons; DoD COOL; checked September 2026.

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Disclaimer: I am not a financial advisor. The information provided here is for educational purposes only and should be verified independently. See the full Disclaimer.