Aaron Benway

CFP®, EA About Aaron Benway.  Aaron is a Certified Financial Planner (CFP) and IRS Enrolled Agent (EA).  He co-founded HSA Coach, a digital tool to educate consumers on HSAs, track health expenses and other documents, and provide individual financial calculators, to help consumers get the most from their HSA and other savings.  To help individuals directly with their financial planning and wealth management requirements he founded AB Financial Planning.  Prior to co-founding HSA Coach, Aaron was the CFO of ventured backed fintech startup HelloWallet, acquired by Morningstar.  Aaron has an MBA from Harvard Business School and is a graduate of the US Naval Academy.

Articles by Aaron Benway

Health Savings Accounts

Five Tips While Checking Your HSA Beneficiary Form

Estate planning may be one of the least enjoyable aspects to wealth management – does anyone enjoy thinking about their demise? – and yet arguably one the most important.  Individuals can spend a lifetime building potentially life-altering sums of money, and yet by overlooking a few estate maintenance items can significantly increase their estate tax…

3 min read

Self Employed

Self-Employed and Considering an HSA?

According to the US Bureau of Labor and Statistics, over 15 million people – 10% of the workforce – are self-employed.  A very large number, this group thinks differently than their company employee counterparts, often because they must.  For instance, being self-employed generally means knowing income, expenses and, yes, taxes, much more closely than those…

3 min read

Health Insurance

Moving From the Security of a PPO/HMO to an HDHP Paired with an Health Savings Account (HSA)?

It’s hardly newsworthy that health insurance and health payments are becoming more expensive.  This trend impacts employers, who still pay the majority of health care costs in the US, as well as employees whose share of the total costs continues to increase.  This cost sharing occurs in a few components, as well as across insurance…

4 min read


How Your Section 125 Cafeteria Plan Interacts with Your HSA

Some of you might have heard of a “Cafeteria Plan.”  A smaller number may have even heard the term “Section 125.”  However, most HSA owners have never really needed to know these terms, much less the underlying mechanics governing the employer benefits programs it created.  Still, for a minority, including those serving in a company…

3 min read


How to approach an HSA: Contributions, Savings & Investments

A Health Savings Account, or HSA, may be one of the most versatile and tax-efficient savings accounts available.  Designed to be paired with a qualifying High Deductible Health Plans (“HDHPs”), the HSA takes the tax advantages of familiar Flexible Savings Accounts (FSA’s) and adds a number of new features that turn this health-oriented savings accounts…

6 min read


HSA Funds: Spend, Save or Invest?

Perhaps the only decisions more personal than health decisions are the financial ones – How much should I save?  Where should I save? Where can I find help if I need it?  These are big questions and deserve attention.  Your choices create options after only a few years and become life-altering over a career.

6 min read