Why Sellers Stay Broke and Stuck (Even With Big Commissions)


A Guide to Building Financial Security as a Tech Seller

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Let’s talk about something that doesn’t get nearly enough press coverage: money: moolah, dinero, coin, capital, scratch (you get the idea).

And no, I'm not talking about company money either. Not revenue, pipeline, deal size, quarterly forecasts, or annual bookings.

I'm talking about your money. What you do with it. Where it goes and why some reps earn six figures but still feel broke and stuck in a bad situation.

*Now, this isn’t financial advice. I’m not a financial advisor, planner, or CPA (I'm just an AE).

But I have spent over a decade in this business, and I’ve seen a few patterns (and learned a few painful lessons) about managing cash when you’re in a high-risk, high-reward career like tech startup sales.

Here's how to stay in the game long enough to win big.

Start With One Goal: Buy Yourself Time

You want to take a run at that early-stage startup? Start your own company? Escape a toxic company?

Well, you can't do any of that if you're living paycheck to paycheck. So step one is building a personal runway. I don’t care if you call it an emergency fund, a freedom fund, or just "sleep at night" money.

You need at least 3 to 6 months of your living expenses in cash, not stocks, definitely not crypto, and not some index fund you can’t touch.

Make it boring. Make it liquid. The more cushion you have, the more risks you can take.

But don't overdo it either. Too much liquid cash on hand won't help you outpace inflation or grow your nest egg.

Learn to Live on Your Base Salary

This one's simple on paper, but most sellers struggle to maintain the discipline to do this: Live off your base salary and use your commission checks to build your net worth.

When you start making real money, it's super easy to fall victim to lifestyle creep. You get a $20K commission, and suddenly you’re booking an extravagant vacation, buying the new gadget, or upgrading your living space.

Try to resist the urge.

Get in the habit of sweeping your commissions into a savings account the moment they're deposited. No easy access. Then decide where it goes next: investments, runway, or a guilt-free splurge you've already planned for.

Commissions are the fuel for building wealth. Stop burning them on dumb shit.

Write Down Your Plan

This is something I actually do.

I open Apple Notes and write out my financial plan. Nothing fancy. Just goals like:

  • By age 35, have $X invested
  • By 39, no debt and a year of runway
  • By 45, have the option to stop working

Do this over a solo lunch at your favorite cafe or sushi joint. Write it down on a napkin if you have to.

The point is: most reps never define what rich looks like to them. So they never stop chasing an arbitrary number.

Understand How Money Flows

The better you understand your own finances, the better you’ll be at selling. Seriously. You want to understand how enterprise budgets work? Learn how to manage your own.

If you know how money moves, how it gets allocated, and who controls it, you’ll be sharper in the deal cycle.

Some recommended reading:

  • I Will Teach You to Be Rich by Ramit Sethi
  • Rich Dad Poor Dad by Robert Kiyosaki (Take Kiyosaki with a grain of salt. He's a bit eccentric)
  • Think and Grow Rich by Napoleon Hill

Not perfect, comprehensive books, but they’ll get the gears turning.

Pay Off High-Interest Debt

If you’ve got high-interest or credit card debt, pause everything else and focus on that. I had $10K of it early in my career and it almost crushed me. Interest piled up fast, and it became a source of constant stress.

The sooner you kill that debt, the sooner you can play offense. Use the snowball method to eliminate it fast.

Build a Budget (Yes, Really)

Track your income and expenses. You can use a spreadsheet. You don’t need to get fancy and buy a bunch of budgeting tools.

Figure out your monthly burn. Then save 3 months of it. Then 6. Then 9. Eventually a year.

If you want my budget template (it’s not pretty but it works) just reply to this email and I’ll send you a copy.

Use the Right Growth Vehicle

Once you have savings (runway) and no debt, it’s time to ramp up investing.

Some basics:

  • Roth IRA: grow your money tax free
  • 401(k) with a match: never leave free money on the table
  • Brokerage/index funds: low cost, long-term
  • DRIP stocks: dividends reinvested automatically
  • Real estate investing: higher risk, higher initial capital required, but high upside if done right
  • Startup angel investing: tread carefully, but know your advantage
  • Crypto: don’t bet the house

Set it. Forget it. Let compounding do the heavy lifting.


Treat Debt Like a Tool

Credit cards aren’t evil. But if you don’t know how to use them, they’ll eat you alive.

Use them for business travel. Rack up points. Pay the balance in full, but don’t spend just to earn rewards.

This Isn’t About Getting Rich (Per Se). It’s About Getting Free.

When you have runway, no debt, and cash flowing into investments, you get to make decisions from a strategic position.

You can:

  • Walk away from a toxic job or a bad boss
  • Say yes to a high-risk, high-upside role
  • Build something of your own
  • Sleep better at night

Too many sellers stay broke and stuck because they never build a plan and a system for their personal finances. They let their lifestyle inflate with their income. And when the market turns, all hell breaks loose.

Not you though, you're a Sales Player.

If you like this topic, then be sure to check out the pod episode I did on Building Financial Security as a Tech Seller.

Here's to your financial freedom and success!

-JMW


Featured Episode: The Anonymous Tech Seller Who Built a 6-Figure Side Hustle with "Fidel Cache Flow"

Jesse sits down with "Fidel Cache Flow," an anonymous tech seller who’s built a cult following on Sales Twitter with unfiltered takes on career growth, wifi money, and escaping the W2 grind. Fidel runs Desperados, a fast-growing private community for sellers looking to build income beyond quota. In this episode, they dive into contract stacking, virtual assistants, building while employed, and why aiming for #1 on the leaderboard might be the wrong game.


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Sales Players is on a mission to reach 1,000 reps, founders, and operators in tech with FREE weekly content that explores the mindset, skills, trends, and tools used by the industry's top players to win at the game of tech sales.

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