A Less Outrageous Way to Optimize Your HSA

How you feel when someone asks how you’re optimizing your HSA for maximum growth and lowest tax liability

So most PF or FIRE advice around a Health Savings Account (HSA) optimization goes something like this:

  1. Make the maximum HSA contribution for the tax year (e.g. $3,550 individual or $7,100 family in 2020) and front-load the contribution if you can
  2. Invest that contribution into low-fee funds, ideally a highly-diversified index fund or a fund that that might generate lots of short-term gains or dividends for tax optimization
  3. When qualified medical expenses are incurred, DON’T USE THE HSA, but rather cash-flow those costs and keep the receipts; THEN
  4. Let the beautiful magic of compounding and historic market growth do its thing until you hit the age of 65 when you can then withdrawal the funds as ordinary taxable income Ă  la Traditional IRA; OR
  5. Withdraw the funds before 65 when an investment opportunity arises that would beat the historic, broad market growth of 8% (or, ya know, an emergency) using the receipts you diligently saved before to reimburse yourself for those qualified medical costs incurred many years or perhaps decades prior

Assuming you have the cash flow to cover those medical expenses, this approach is the mathematically correct answer and all things being equal, the logic is sound… but given our nature and fallibility as human beings, I have a couple concerns with this approach.

One, the future is basically unpredictable, especially when it comes to humans, and specifically so when it comes to matters of policy. We have no idea how tax policy and healthcare will change over the years. Will fat HSA balances be subject to a new tax? Will the IRS adopt a use-it-or-lose-it approach for qualified expenses? Will the definition of a qualified expense get narrower? Who knows.

Two, and let’s get a little morbid for second, what if you die or become mentally impaired for some reason? Do you want to leave your family with the burden of figuring this out? Or not, and effectively leave money on the table with the IRS? I think it’s a fair generalization that us PF/FIRE types love our spreadsheets and detailed, quasi-algorithmic plans, but what about the person we marry or the kids we raise? They may not think like us and I’d rather not dump this beautifully complex burden on them.

So what do I do instead?

Try to strike a better balance between math and human behavior.

  1. Make the maximum annual contribution to my HSA; this comes through payroll deduction for me, so no front-loading 😢
  2. Keep no more cash than my annual deductible amount in the HSA deposit account and invest anything beyond that in low-fee, broadly-diversified index funds or REITs
    #Protip: if your employer-sponsored HSA custodian is fee-heavy or offers no/poor investment options like mine, consider opening an HSA with Fidelity and making in-service transfers from the sad-panda HSA 🐼 over to Fidelity’s no-fee HSA 🙌
  3. And here’s the difference! As medical expenses are incurred, I cash-flow them, but simultaneously withdraw the funds from the HSA and invest them into regular, non-tax advantaged brokerage account (VTSAX FTW!); THEN
  4. Let the beautiful magic of compounding and historic market growth do its thing until an another investment opportunity occurs or retirement or… well, whenever I want for whatever reason, no penalties 😁

What do I give up with this approach? Assuming nothing changes, I’ll miss out on tax-free gains, and gains on gains, and gains on gains on gains ad infinitum over the years or decades as those HSA dollars have lost their cool tax-advantaged name-tag. Boo-hoo… that’s the opportunity cost of keeping life a little simpler. What I gained is more important to me. Namely, I get rid of the need to keep track of receipts for decades worth of medical expenses to be reimbursed ad-hoc or post age 65, won’t leave my family with the burden to figure this all out if I’m mentally-impaired or die prematurely, and dodge any policy changes to HSAs.

So that’s how I approach HSA optimization. How about you? Disagree? Have other interesting approaches? I’d love to hear them. Let me know in the comments or tweet @totesoutraged.


2019 Goals in Review + 2020 Goals

Oh snap! It’s 2020 and about a year since I wrote out my 2019 goals. Let’s see how I did.

2019 Post-Mortem


  1. Max 401k ($19k) ✅
  2. Max IRA ($6k) ✅
  3. Max HSA ($3,500) ✅
  4. Pay off Student Loans ($16,231.52 remaining as of 1/1/19) ✅


  1. Take a sabbatical to redefine my purpose ?
  2. Get a dog ❌
  3. Develop a regular fitness routine ❌
  4. Give regularly to something I care about ❌

2019 Commentary:

Ok, so clearly the financial goals were a lot easier to hit as these were all automated. While I didn’t end up taking a sabbatical as planned due to a bizzaro medical mystery (mostly harmless) that forced me to burn through my deductible and out-of-pocket max, I did end up attending a CampFI event and Jillian’s Adventures to FI (#A2FI) event in Montana, which was effectively a mini-sabbatical (thus the participation ribbon I gave myself ?). With my sabbatical plans in limbo, I decided to delay getting a dog, but good news is that many furry friends have made their way into my life, so I’m subsisting for now. I would also like to claim that the bizarro medical issue prohibited me from getting into a regular exercise routine, but I would be lying. I need to develop a better system/schedule and that’s part of my plan for 2020. It’s a similar situation with the last goal; I didn’t put enough attention into defining what I wanted to do, which is something I plan to work on this year as well.

So now, what’s in store for 2020?

2020 Goals


  1. Max 401k ($19.5k)
  2. Max IRA ($6k)
  3. Max HSA ($3,550)
  4. Buy 3 Investment Properties
  5. Elect a charity as my financial beneficiary

Health and Fulfillment:

  1. Develop a regular fitness routine by:
    1. lifting weights at least 1x/week and cardio at least 1x/week
    2. playing Ultimate for at least 3 seasons
    3. practice yoga at least 1x/week
  2. Continue going to therapy at least 1x/month
  3. Identify a charity or cause to give my time to at least 1x/month
  4. Record a voice-over demo and take at one job
  5. Take voice/singing lessons and/or join a choir
  6. Help my parents identify/pursue/achieve one goal this year
  7. Minimize waste: electric, water, plastic/packaging
  8. Purgefest: declutter and sell/donate stuff
  9. Write a blog post at least 1x/month focusing on tips/tricks I’ve learned that might help others
  10. Budget so that Alcohol/Bars + Restaurants is less than 2x Groceries
  11. Help my roommate garden in the spring/summer

2020 Commentary

Yeah, so I have a lot more goals for 2020, but they’re all achievable, mostly measurable, and a good mix between helping myself and others. I’ve been lucky to meet a whole lot of super cool people in the PF/FIRE space in the last six months that have inspired me in one way or another to chase these goals.

Be well.


2019 Goals

Let’s keep this brief.


  1. Max 401k ($19k)
  2. Max IRA ($6k)
  3. Max HSA ($3,500)
  4. Pay off Student Loans ($16,231.52 remaining as of 1/1/19)


  1. Take a sabbatical to redefine my purpose
  2. Get a dog
  3. Develop a regular fitness routine
  4. Give regularly to something I care about


Financial goals are looking real good with the exception of the HSA as I plan to take a sabbatical during the year and not sure what the medical insurance situation will be (and therefore HSA eligibility). For now, 401k is being front-loaded on autopilot (will be fully funded by April) and I already made my 2019 IRA contribution in full. Although precluded from contributing to a Traditional IRA for 2018, I went with a Traditional for 2019 on the basis that I expect my income to be lower (if I’m wrong, I can always recharacterize). I would just rather take the discount today than in the future, ya know? Student loans should be gone or close thereto by May. Even if I still have a balance, my loan is variable and resets quarterly, so after paying against principal in Q1, the required payment should be unnoticeable.

Other goals are still a work in progress, but I’m striving to make some more concrete definitions by the end of the month. Just wanted to put them down in writing.

Mr. PTM Net Worth

Mr. PTM’s July 2016 Net Worth

So first, to address the sad elephant in the room:

The blog has been pretty silent lately and it’s not like our track record was that great to begin with, but ya’ know, life happens and stuff gets pushed to the side.

But I’m back!

I was recently gushing (yes, gushing) to a friend about my high-yield emergency fund strategy (post upcoming) and he said I should write a blog. Ah, that was nice to hear and honestly, I find myself wanting to write more lately. I know almost no one reads this and I’m ok with that – this is a creative outlet. If this blog serves as nothing more than something to have a few laughs over as Ms. PTM and I remember this time in our lives, that’s fine!

But let’s get on with it

July was a wild month that included such highlights as: spending time with Ms. PTM’s family for the 4th, starting the Whole30 diet (deserving of its own post), and selling my car! But first, let’s share some numbers.


Cash – $19,813

First, a little real talk. This is artificially inflated. I did something most financially responsible people would balk at – I used a convenience check from Chase to borrow $13k. Why? Well, you’ll have to read my follow up post to find out. Also important to note here is that this reflects a change in strategy for both Ms. PTM and I: a shift from throw-everything-and-the-kitchen-sink at debt payoff to squirrel-away-every-free-penny to savings. In short, we’re trying to build our emergency funds. More to come on the what, why, and how.

Also one of my accounts doesn’t show up in Mint (I can’t blame them, the bank’s online banking website is terrible, like 1990s GeoCities terrible), so I’m not including about another $3k here.

Credit Cards – $19,373

This is the other side of the inflated cash coin, but also includes about $1,900 of Ms. PTM’s work travel expenses and almost $3k that I paid towards my student loans in order to hit a $400 signup bonus (thanks, Wells Fargo!).

Loans – $99,319

Finally under $100k!!! I hit this milestone in June and it still makes me happy to no longer have six figure student loan debt. Obviously the real dollar difference is small, but it feels like such a symbolic victory.

Investments – $116,695

Brexit. Oil. US election. I have no idea what’s going on here, but it doesn’t matter. I’m in it for the long-term and still on track to max out my 401k, IRA, and HSA for the year, so high fives all around.

Property – $0

Property $0? Yup, I sold my car for $2,200 and it felt great, although I was overwhelmed with feelings of nostalgia as I watched the new owner drive away. BUT, instead of a depreciating asset, I know have a compound-interest-earning-engine-of-growth. (See what I did there with the car metaphor? 😉 )

Net Worth – $17,816

After 5 years, I went net worth positive as of my March 15th paycheck this year and market-willing, it’s going to stay that way.

Pennsatucky - Praise The Market


Well that’s it for me. How was your July? Any new milestones, financial or otherwise?


Protip: Best Credit Card for Costco Purchases

Overdue 2020 Update: Fidelity changed card management firms and now the Amex version is gone, replaced by an equally excellent Visa version, which nicely coincided with Costco’s move from only accepting Amex to only accepting Visa, so the advice still stands. 🙂

TL;DR – The Fidelity American Express earns 2% cash back on all purchases, even at Amex-only Costco. Both firms are ending their relationship with AmEx, but this card and Costco are both transitioning to Visa network cards sometime this summer, so the 2% will continue.

After a long work day yesterday, Ms. PTM and I were looking forward to a relaxing night on the couch watching a movie. We get home, take care of the pups, order a pizza (#treatyoself), go to turn on the TV, and… nothing. TV was dead. No light, no sound, no nothing. Thanks to an alert from SimpliSafe earlier in the day, we knew we lost power for about 15 minutes, which was confirmed by the blinking time on the oven and microwave, but power loss doesn’t typically break shit. It did this time though. After a Google search to find a quick fix, it looked like power supply problems were fairly common with this model TV and would require a more in-depth repair than was worth our time. I’ll also admit that this looked to be a good opportunity to replace an old, heavy, power-hungry plasma TV.

So it was off to Costco!


We made a quick decision to get a replacement that night from Costco (it was fastest electronics purchase decision I’ve ever made and apparently the slowest for Ms. PTM). Why Costco? They tend to have comparable prices to Amazon (especially now that Amazon is collecting CO sales tax) and have a highly respectable return policy. How did we decide which TV to get? I’m partial to Vizio TVs for providing a nice sweet-spot between affordability and features and their recently released D-series seem to fit the bill. Power efficient (seriously, like $18 a year), ‘Smart TV’ apps built in (hooray Netflix, Amazon Video, PLEX!), and 4K resolution (not a lot of content, but Netflix seems to be adding more and more), plus their sister M-series was well reviewed by CNET. Although we were looking for a 50″ version, Costco was sold out except for the display (which was minimally discounted), so we went big: $699 58″ big. The difference between the 55″ and 58″: $10. So what were we to do but buy the giant ass TV?

Now to the #protip!

Costco, at least until this summer, is still an Amex-only shop. Their own True Earnings card issued by American Express only earns 1%, but the Fidelity Investment Rewards card (issued by FIA Card Services, a subsidiary of Bank of America) earns a full 2%. This card has earned a top spot in my wallet for its simple 2% cashback program. The scheme is simple: each dollar in purchases yields 2 WorldPoints, which can be auto-swept into a Fidelity Cash Management Account, i.e. checking, at $50 increments (5k points). Once in the Cash Management Account, you can ACH that money out to your primary bank, use free bill pay and free ATM withdrawal, or even invest it. Now what about Costco’s switch to Visa this summer? Conveniently, this is about the same time that Fidelity Investment Rewards cardholders are being transitioned to a Visa card themselves, which is issued by Elan Financial Services, a U.S. Bank subsidiary (bad news for AmEx, good news for you), so the 2%-cashback-at-Costco-love will continue.

Hope this was helpful. Thanks for tuning in! 😉


August 2015 Expenses (Mr. PTM)

Happy September! Here in Denver, fall hasn’t poked its head out yet, but fret not, winter is coming.

In fact, we expect this winter to be a doozy due to the El Nino weather phenomenon. Of course, terrible weather makes for low Lyft-supply, so there should be some good arbitrage opportunities for Lyft drivers who aren’t afraid of a little snow, i.e. me. 🙂

So let’s get to it; my first monthly expense breakdown!

I used to Mint to categorize the data, then exported it as a CSV file to Excel, so that I could create a chart with data labels. Mint’s charts are much more lovely, but there’s no option to add data labels. Bummer.

Spending Breakdown August

Student Loan – $872.90, 29%: Usually my largest monthly expense, this is my standard monthly payment to DR Bank. In a future post, I’ll share how I refinanced my student loans from 6.8% to 2.78%.

Home – $588.56, 20%: This includes $500 for “rent” (paid to Ms. PTM) and some various Home Depot buys to get our refurbished grill up and running again.

Food and Dining – $502.76, 17%: Sadly, this is much too high in my opinion. Ms. PTM and I had several weekend adventures last month, which resulted in more dining out than usual. We’ll again have some out-of-town adventures this month, but I’ll work to be more conscious on how we can only eat out when it’s really going to bring us pleasure.

Bills and Utilities – $444.67, 15%: Also higher than usual due to a $260 f@$& up where I washed Ms. PTM’s iPhone 6 with the laundry (if you knew me personally, you would know I never make this kind of mistake, which makes it doubly frustrating and embarrassing). Fortunately, she was kind enough to endure the flip-phone life while we had T-Mobile mail us a replacement. At least I didn’t end up having to pay full retail for the replacement.

Auto & Transport – $257.98, 8%: Gas, gas, and gas. This is both from a couple of intra-state trips this month (woot! Gunnison and Crested Butte) and from Lyft driving.

Travel – $214.04, 7%: Full-day kayak adventuring during our upcoming trip to the Seattle-Anacortes area for a friend’s wedding next week. I’ll cover this while Ms. PTM will cover part of our lodging.

Personal Care – $21.15, 0.7%: Dry cleaning, a bimonthly expense, which it turns out is surprisingly cheaper for men than women. I brought in 5 shirts and 2 slacks for ~$21, while Ms. PTM’s 4 dresses cost her ~$54. Seriously.

Fees & Charges – $17.71, 0.59%: My employer’s 401(k) custodian, Fidelity, charges a $12.50 quarterly fee for access to a full brokerage account for retirement funds, which was the only way for me to access Fidelity’s biotech fund (FBIOX) and Vanguard’s Real Estate ETF (VNQ). The rest of this was from ATM fees that will be refunded by USAA sometime this month.

Shopping – $0.99, ~0%: I offered to replacement Ms. PTM’s mother’s iPhone 6 cracked LCD. I purchased the replacement part on eBay for $68.99 and funded $68 of it with an eBay gift card using my 6%-cash-back-at-grocery-stores AmEx Blue Cash Preferred (I’ll share more about this easy, cash saving strategy in a future post). Of course, she’ll reimburse me for all costs and it never hurts to earn a little goodwill from your future MIL.


Ok, so that’s August, totaling in at $3,004.26, which keep in mind is only my expenses (*groan*). Lots of room to cut down for the next month if we can keep travel-related indulgences to a minimum (or maybe value-maximum…that sounds better). Just for grins, I’ll leave you with a chart of my month-to-month spending since the beginning of the year to put this into perspective. I’ve had a couple of pricey months here, so the rest of the year will be focused on getting as close as I can back to that June 2015 number (seriously, ~$750?!).

Spending by Month


Mr. PTM Net Worth

Mr. PTM’s July 2015 Net Worth – Let’s Do This!

Ugh, finally!

We bought the domain and set up hosting with Dreamhost and love them (more to come in a future post!), set up Zoho as our email host (sure, let’s review that too), and picked our WordPress theme (it seems clean enough, content focused, and works well on mobile too) – so now to get on with what we came here to do and put out some content for you all! To start us off, let me share my first net worth update!

Net Worth End of July

Whoa – maybe not what you were expecting to see. Or maybe it was. Regardless, a negative net worth is not the most exciting thing in the world and I’m working tirelessly to get it positive.


Suffice to say, I’ve made some good progress (almost $25k increase in 6 months), but more on that later. For now, let’s break down my accounts (thanks to Mint):


USAA – my primary bank since I was a tot. Fantastic customer service. I keep multiple checking and a savings account here.

HSA (company-sponsored through BCBS’ BenefitWallet) – I keep $3k in here for medical emergencies and anything beyond is auto-transferred to an investment account (these things are a triple-threat in the tax avoidance world).

Mango Money Checking and Savings Accounts – almost $2k, but I’m growing to $5k as to be my Emergency Savings (it doesn’t get much better than 6% APR and FDIC-insured – more to come here too).

Chase – basic checking account set up to take advantage of a recent $300 offer (free money!) and should also help me pay down an outstanding balance on a certain Chase Freedom card as mentioned below.

Credit Cards:

More than half of this is due to to a convenience check I wrote to myself earlier this year (as part of a sweet balance transfer offer with 0% APR for 14 months and a 2% fee) in order to partially front-load my IRA and cover a cash-flow issue). Unfortunately, this has taken me longer to pay than I would have liked, but I’m working on it and it will die. 🙂

The rest of the balance is split amongst the following cards that I pay in full every month (believe it or not – I actually have more cards than this, but these are the only ones I use regularly or semi-regularly… more to come on this in future posts):

  1. Amex Blue Cash Preferred
  2. Barclaycard Rewards
  3. Barclaycard Upromise
  4. Chase Sapphire Preferred
  5. Chase Freedom
  6. Citi ThankYou Preferred


Student Loans from grad school held by Darien Rowayton Bank. Although consolidating and refinancing these 8+ loans from The Iron Bank Nelnet to a single loan at a much lower rate from DR Bank was a life-saver, this loan is the bane of my existence and my primary impediment to freedom.



Fidelity – holds my workplace 401k accounts (traditional and Roth), which includes a brokerage account for ETF purchases.

Vanguard – the golden child of the personal finance world, they hold both my Traditional and Roth IRA accounts, plus my after-tax accounts I set up long before I knew how to shield my investments properly.

BenefitWallet HSA Investment Account – currently makes up a very small part of my portfolio.


My good ol’ 1999 Subaru Impreza Outback Sport that I affectionately call Babu is a champ. According to Mint vis-a-vis Kelly Blue Book, she’s valued at $2,185, but I’m not sure that’s what I could get for her.

Feast your eyes on this Japanese supercar! (cowboy and horse not included)

Alright – that’s all I can muster for now. If you’re still reading – thank you! I hope to deliver some better posts that help you on your personal finance journey (you know, pay it forward as they say).