12 Money Tips To Help Your Commission Checks Go Further

We started GTMBA to help sellers sell more effectively and improve a big part of their lives: their careers.

Having a successful career comes with a by-product of more money, and while it’s important to get the “get good at your career” part right first, it’s also important to make sure, when you have the commission checks & equity rolling in, that you are smart with what to do with them.

As a former CPA and someone who is money-hack obsessed (shout out to my secret weapon, Chris Hutchins, with his All The Hacks podcast), I thought I’d share the top 12 tips I’ve learned to help your commission checks go further and have your money work for you.

1. Join a company with a product so good that the worst salesperson can sell it

Do your best to expand your luck by joining a breakout company.

So much of your success is defined by how easy the product is to sell.

Self-explanatory, I know. However, many reps cannot effectively evaluate top opportunities.

I wrote about the 11 traits that make a sales job desirable - but if you could only pick 1-2 of these, it’s:

• Market pull/inbound - as this is a sign of PMF and a job where you have to outbound 100% of the time is a (bad) sign they’re hiring sales ahead of demand (which should be done by someone in marketing)

  • The exception here is a product that first of its kind/to market, and just needs some light outbound to shake the tree - but these are rare

• Talent density - as working with smart, ambitious people is awesome, and those people will go to the next great startups and pull you with them - the best flywheel

Get these two right consistently, and you’re on your way to a fulfilling career in tech sales. Mainly, you’ll be able to make a ton of money, a main driver in making your commission checks go further (by making them larger).

For top candidates reading this, I'd be happy to have a conversation on this through our learning from our GTM recruiting firm, VibeScaling.

2. Be so good at your craft that you could sell the worst product (if you needed to)

Since #1 is hard to nail down, and sometimes it takes working at some bad companies & hitting singles/doubles first to realize how to analyze #1 as well as getting good at your career, the faster you speed up your professional development curve, the better off you'll be.

I wrote an article that covers #1 and #2 but focuses on ways to improve at sales - "Learn Like Mongo, Join Like Stripe."

Another self-explanatory one, but sales is a skill you need to learn (not something you're born with), so the faster you get good at it, the more you'll make. Commission checks will be larger and go further.

This one is fully in your control.

Oh, and keep reading GTMBA to help here 🙂

3. Direct Deposit Your Checks Into A High-Yield Savings Account (HYSA) Like Wealthfront

A mistake I used to make: I’d have my direct deposits go into my Chase account (which would get close to 0% return), and then I’d have to wait 3-5 days for it to transfer into another account like Wealthfront. That means I’d miss 3-5 days of compound interest on each paycheck at a much higher yield.

I just used Chase for years and had this on autopilot - Tim Ferriss finally woke me up to using Wealthfront for direct deposit and it’s been great for my wife and I.

This original strategy, compounded over the years, results in thousands of dollars lost compared to directly depositing into a HYSA. So I went ahead and changed this a little while back and kick myself I didn’t do it right when I first started working.

Currently, Wealthfront offers the highest rate I’ve seen at 4% (you can earn 4.5% if you use my referral link here). I love how intuitive the UI is, and it feels modern compared to the clunky interfaces of big banks like Chase and Wells Fargo.

However, this 4% is fully taxed at both the federal and state levels, and I’m starting to learn that there might be better ways. See #4 below.

4. Invest In Funds Exempt From Federal & State Income Tax To Get 5-6% On Your Money

While having your money in a 4% HYSA (#3) is great, the issue for folks like myself who live in the NYC area is that we get taxed up the wazoo.

I recently learned that investing in money market funds and treasuries is a way to boost your returns to a pre-tax adjusted basis in the 4.8-6% range. Municipal money market funds (which invest in bonds issued by states, cities, and local governments) are exempt from federal taxes, and treasuries are exempt from state and local taxes.

You can buy treasuries through Wealthfront's bond ladder program, but it does not offer the ability to purchase money market funds.

To supplement this, I recently started using Carry (shoutout to Ankur who just did a great episode on MFM) - their SmartYield product is killer, and while it takes me off Wealthfront it's worth it to start testing to have some money working for me closer to a ~5% pre-tax equivalent at virtually a risk-free rate.

Use my referral code here for a free $100 off the membership.

Highly recommend this hack for folks in a higher tax bracket (since you're earning those commissions now 🔥) to reduce your federal tax burden and/or in a state with high taxes (like NJ/NY/CT/CA).

5. Stop Investing In VOO (Vanguard S&P Index Fund) and Start Direct Indexing

While investing in VOO (Vanguard S&P Index Fund) is fine, I stopped doing it this year. There’s a better way if you're taxed at a high rate.

I recently discovered direct indexing through platforms like FREC, which essentially allows you to own the individual stocks that make up the S&P 500, rather than just owning the fund. (Wealthfront has a similar feature now)

The killer feature as to why do this over an index fund is tax loss harvesting - when individual stocks in your portfolio go down, you can sell them to realize losses that offset your gains, while immediately buying similar (but not identical) stocks to maintain your market exposure.

With a traditional index fund like VOO, you can't do this, as you only own one fund. However, with direct indexing, you're constantly harvesting losses throughout the year (FREC and Wealthfront do this automatically for you), which compounds into a ton of value.

The math works out to potentially 1-2% additional annual value through tax alpha, which compounds nicely over time. Plus, you still get the same broad market exposure in the S&P 500 that you'd have with VOO for a similar low cost.

6. Contribute To A Health Savings Account (HSA)

Most people do this through their employer, but you can also do it through a bank.

If you have a high-deductible health plan (pre-requisite), an HSA is probably the best tax-advantaged account you're not maximizing.

It's triple tax-advantaged - you get a deduction when you contribute, it grows tax-free, and you can withdraw it tax-free for medical expenses. No other account gives you that trifecta.

A ton of things you're probably already buying are HSA eligible - obvious items like doctor visits and prescriptions, but also things like sunscreen, contact solution, band-aids, and even massages if prescribed by a doctor. The list is way longer than most people realize.

Unlike an FSA, you don't lose it at the end of the year - the money rolls over and stays yours forever. And once you hit 65, you can withdraw for any reason without penalty (though you'll pay regular income tax on non-medical withdrawals).

It's essentially a way to reduce your effective medical expenses and save money on items you're already purchasing. Plus, it reduces your taxable income right now, which means more money in each commission paycheck that you’re direct depositing in Wealthfront or Carry 🙂.

If you're eligible, this should be one of the first accounts you max out after getting any employer 401(k) match. Another way to make those commission checks go further.

7. Negotiate Your Stock Exercise Window To 1+ Year(s)

Most companies give you 90 days to exercise your stock options after you leave, which is honestly brutal if you don't have the cash sitting around (plus the tax bill if the company has grown) or are not sure about the company’s long-term growth potential in that short of a window.

I've seen people lose serious equity because they couldn't come up with the money in time, and this happens way more often than you'd think. I’ve also seen people be forced to buy stock that ended up being worthless because they had to make a quick decision in the 90-day window.

The move: negotiate a longer exercise window (ideally 1+ years) during your offer process so you're not forced into a terrible financial decision if you leave.

This costs the company nothing but could save you from walking away from potentially hundreds of thousands down the road (or wasting the same amount).

8. Backdoor Roth IRA

If you're making good money from those commission checks, you're probably over the income limit to contribute directly to a Roth IRA (around $140k for single filers).

The backdoor Roth allows you to bypass this - you contribute to a traditional IRA with after-tax dollars, then immediately convert it to a Roth.

This way, you still get tax-free growth and tax-free withdrawals in retirement, even though you're "too rich" for a regular Roth contribution.

It's a legal loophole that allows high earners to continue building tax-free retirement funds.

9. Consider Getting A Short-Term AirBNB Rental To Avoid Taxes

If you're making good money and looking for a solid tax hack, short-term Airbnb rentals (under 7-day average stays) qualify for bonus depreciation under Section 179, which lets you write off a huge chunk of the property cost in year one.

This differs from regular rental properties, where depreciation is spread over 27.5 years. With short-term rentals, you can potentially offset a significant portion of your W-2 income immediately.

The bonus depreciation was recently phased down, but there is talk from the current administration about reinstating it to 100%, which would make this an even bigger opportunity.

Obviously, this requires buying real estate and actively managing it, but if you're in a high tax bracket and want to diversify anyway, it's worth exploring with a tax professional or some Perplexity searches.

10. Managing This Myself And Not Using A Financial Advisor (Yet)

I have a ton of respect for financial advisors, but with all the new technology and most of us being tech-savvy enough to handle the basics, paying 1% annually to get not much more alpha than the market adds up to serious money over time.

When you're earlier in your career and have $100k-$500k invested, that 1% fee could be $1k-$5k per year for advice you might not really need yet. The tools available now (i.e., Wealthfront) make it pretty straightforward to handle asset allocation, rebalancing, and tax-loss harvesting yourself.

That said, definitely review whether the fee you're paying is actually worth it - sometimes it is if they're doing real tax planning or estate work, but it might not be for basic portfolio management. YMMV.

11. See If Your Employer Has A Non-Qualified Deferred Compensation Plan (NQDC)

(disclaimer - I haven’t done this, but just recently learned about it as a level 2 money hack)

Most high earners at startups and growth-stage companies have never heard of NQDCs, but if your company offers one and you're making serious commission money, it can be a way to defer income to you'll pay lower rates later (whether by taking out less or living in a lower-taxed state).

You basically ask your employer to set aside some of your compensation, invest it tax-free, and pay you out later when you're in a lower tax bracket - it's tax arbitrage that allows pre-tax money to compound.

The problem: Unlike your 401(k), this money isn't protected if the company goes under - you're essentially lending money to your employer with no guarantee of repayment.

At a high-growth startup where you're already taking massive company risk with your equity, adding more risk by deferring cash comp probably doesn't make sense unless you're at a later-stage, well-funded company.

12. Using Claude To Pressure Test Assumptions & Portfolio Balancing

Claude is my secret weapon (pretty much my therapist at this point) for asking all the dumb questions throughout the learning process of these hacks.

I highly recommend using any LLM and having it act as a financial expert to help give you confidence that you are making 80/20 decisions.

Hope you all enjoyed this - a little different type of article for today, but if you have any questions, shoot me a DM!

Chris