About Winged Wealth


Winged Wealth Management and Financial Planning began in 1997 with an idea: In order to get sound financial advice, pilots and the military community shouldn’t have to use a giant financial services company that sells high-priced, high-commission, and often inappropriate financial products.   Instead, they deserve sound, fiduciary advice and they should be able to choose how they get it.

Over 23 years serving in the Air Force and flying the F-16 and F-35 in combat, test, and training, I’ve helped hundreds of airmen, soldiers, sailors, marines and veterans understand how to max perform their income to produce the opportunity for wealth, a secure retirement, realization of life goals, and financial peace of mind.

Aside from delivering and raising my daughters, marrying my best friend, and having the opportunity to defend our nation, learning to build wealth and help others do the same has been my focus.

So, after years of study and practice, I earned my Certified Financial Planner® (CFP) designation and opened Winged Wealth Management and Financial Planning LLC.

Our Mission is to help pilots and the military community—young, and not-as-young-as-they-wish to gain the same superiority with their financial life, that they attain in their professional life.  Air superiority for your financial life—if you will.

Our Vision is pilots and their families, confident in their financial planning and choices, on glidepath for a wealthy and secure retirement.

Our Values

  • Integrity – Not just doing the right thing regardless of who’s watching, but saying what we’ll do, and doing what we say we’ll do.
  • Excellence – Our clients deserve and receive the best service we can deliver, but we’ll always be improving it. Full stop.
  • Humility – There is no such thing as perfection. When we make a mistake, we will own it and fix it to your satisfaction.
  • Learning – A life spent learning is a life well-spent. We plan to live one of those.

Our Philosophy

Investing: According to the SPIVA® report from S&P Global, active fund managers fail to beat their appropriate passive index most of the time.  Winged Wealth believes that a better approach is to seek market index returns in order to suppress investing costs and potentially taxes. Time in the market beats timing the market.  Build an investing plan that works for the decades and stick with it.

Insurance: If it could ruin you, you should probably insure against it… efficiently.  Insurance is not an investment.

Cash Flow:  Tell your money where to go and what to do, or someone else will.

Debt: “When the tide goes out, you can tell who’s been skinny-dipping.” (Warren Buffet)

Taxes:  No need to leave the IRS a tip, especially over the decades.  Tax planning integrates with all financial decisions.

Estate Planning:   No one knows their expiration date.  Everyone hates probate.  Honor your loved ones with estate planning documents.

Wealth: It makes us more of what we are, but it gives all of us choices.  We didn’t become pilots to become mediocre in any aspect of our lives.  Let’s work from the target back and flight follow to make sure we get there!

Brian O'Niell

Frequently Asked Questions:

We find that most investment advisors only focus on your investment portfolio. Does it matter if your portfolio is up 10% if you’ll overpay $79,058 in taxes because a retail investment advisor said you needed to talk to a tax advisor about the tax implications of your investments? YES! A Financial Planner integrates all aspects of your financial life. It’s a subtle conflict of interest, but if an investment advisor doesn’t know that you don’t have adequate life insurance, and still recommends an investment… that may not be in your best interest. Winged Wealth performs Comprehensive Financial Planning and evaluates the whole picture before making recommendations.

It depends on your requirements.  We find that clients benefit the most from an ongoing relationship so that there are no limits to how we can help you.  That said, we’ll work with you to craft the best fit for the scope of our engagement.

Advice, not products.  Full stop.  We partner with our clients to bring education, accountability, organization, objectivity, and proactivity.  Selling products, such as insurance, or accepting commissions on investment transactions works directly against that relationship.

100% by you.  Winged Wealth does not take compensation from anyone but it’s clients.  We do not accept or pay referral fees either.

Yes.  Winged Wealth will work with you to establish a relationship model that has you 100% comfortable with your asset management.

You know the answer- it depends! While this one of our favorite discussions to have, we can’t act as a fiduciary and sling “one-size-fits-all” advice around.

This is a big deal, but the waters in the financial world are murky.  Certified Financial Planners® are always held to the fiduciary standard, meaning we must put the client’s best interest first at all times.  This forms a legal standard and provides the best protection for a client.

This is where the waters get murky.  In 2019, the SEC’s regulation Best Interest came into effect for Broker Dealers.  Previously a stock broker only had to consider whether an investment recommendation was “suitable,” e.g. Can you afford it? Do stock funds belong in your portfolio? This allowed brokers to recommend high risk, high commission, or otherwise suboptimum investments to clients.

Regulation Best Interest requires a slightly higher standard of care in that recommendations must be in the client’s best interest at the time of the recommendation.  There is no comprehensive, ongoing fiduciary requirement.   Winged Wealth believes this still puts clients at unnecessary risk.

Want to know more? Contact us or schedule a complimentary introductory call.