Why Most Entrepreneurs Stay Broke in 2025

I remember the first time someone told me, “You can be high-class broke.” It stung—because I’d built a brand that looked polished while my personal books were messy. That sting pushed me to learn how money actually works in business. In this post I pull from a candid conversation with Jen Perez (the Spicy CEO) and my own missteps to create a short, practical guide to financial literacy for entrepreneurs. I promise a bit of sass, some real talk, and a few concrete steps you can use today.

1) Know Your Numbers: Awareness Over Admiration

One of the biggest problems I see (and Jen Perez called this out too) is simple: entrepreneurs don’t know their numbers—business or personal. And when you don’t know them, you can look successful and still feel stressed every Friday.

Jen Perez: "You can be high-class broke, meaning you could be making millions of dollars and still be paycheck to paycheck."

That “high-class broke” idea hits because it’s real. In our conversation, we mentioned that 83% of business owners operate paycheck-to-paycheck. That’s not always an income problem—it’s often a cash flow management and awareness problem.

Track the cash that matters (not just revenue)

For small business financial management, revenue is nice, but it’s not the number that keeps the lights on. I track two simple things:

• Personal take-home pay: what actually lands in my account after taxes and deductions
• Business cash in/cash out: money collected vs. money spent (including subscriptions and debt payments)

If you tell me your sales but you can’t tell me your monthly expenses, you’re guessing. And guessing is expensive.

Budgeting and saving: one spending plan, two lanes

I believe in a budget—call it a spending plan if that feels better. I keep budgeting and saving simple by running two lanes: personal and business. Each lane gets:

1. Fixed costs (rent, tools, payroll, insurance)
2. Flexible costs (food, ads, travel)
3. Pay yourself first (even if it starts small)

This is how you stop the “money comes in, money disappears” cycle.

15-minute weekly money check (stop rowing in circles)

Jax Crider: "If you don't have that awareness, you're just going to keep rowing the boat in a circle and not really moving anywhere."

Once a week, I do a 15-minute check: bank balance, bills due, invoices outstanding, and what I can safely pay myself. Apps and spreadsheets remove the “I’m bad at math” excuse—use whatever you’ll actually open.

2) The Emotional Ledger: Shame, Taboo, and Spicy Analogies

Why money feels so hard to talk about

Money and sex sit in the same “don’t bring it up at dinner” category. They’re both taboo topics, and that discomfort turns into silence. For entrepreneurs, that silence is expensive: shame can keep me from checking my bank balance, opening a scary email, or asking for help when I need it most. Research backs this up—emotional barriers like shame are a major reason people avoid looking at finances, even when the numbers are simple.

Jen Perez: “There’s a lot of emotion around money.”

That’s why financial literacy for entrepreneurs isn’t just about spreadsheets. It’s about building financial knowledge and confidence when my nervous system wants to hide.

A spicy bridge into personal finance concepts

I love playful framing because it lowers resistance. Jen’s book title, “69 Ways Money is like Sex”, is a perfect example: it’s memorable, a little spicy, and it gives me permission to laugh while learning. When I’m relaxed, I can actually absorb personal finance concepts like cash flow, debt, and profit.

One analogy that sticks with me: a friend once said talking about money is like going to a gynecologist for the first time. It’s the unknown. I wonder, “Are they going to judge me?” It feels like everything is happening behind closed doors. That’s exactly how money can feel—private, vulnerable, and loaded with fear.

Failure stories that teach without shaming

Even people in the financial industry hire coaches because emotions don’t disappear when you “know the rules.” I learned that the hard way. In 2013, I filed bankruptcy because nobody taught me how money works. That moment became my pivot: I had to get my act together, because whatever I was doing wasn’t working.

And it goes back further. My dad lost our family house on 40 acres because he didn’t understand money either. Nobody taught him. That story is painful, but it’s also a teaching tool: not knowing doesn’t mean I’m broken—it means I’m human.

Jax Crider: “Good at math doesn’t really have anything to do with it—apps and tools do the heavy lifting.”

If I don’t know something yet, that’s okay. I can learn it, one honest conversation at a time.

3) Reverse-Engineer Your Lifestyle: Pay Yourself First

My background is in accounting, and I’ve seen the same pattern over and over: entrepreneurs build a business, work nonstop, and only pay themselves if there’s “something left.” That’s backwards. In this financial literacy guide, I want you to flip the order and pay yourself first—on purpose.

Jen Perez: "Reverse engineer that back into the business so that your business supports your lifestyle, not the other way around."

Start with your personal number (your owner salary target)

Financial planning for entrepreneurs gets easier when you stop guessing. Decide what you need personally to support your lifestyle. Think: housing, food, insurance, debt, savings, and fun money. Your goal is a clear monthly take-home number.

Use this simple prompt:

Turn “pay yourself first” into a business line item

Next, reverse-engineer that personal salary back into the business. I like to set “Owner Payroll” as a fixed line item in the business P&L, just like rent or software. This protects your pay and removes the emotion from the decision.

• Step 1: Pick your monthly owner payroll amount.
• Step 2: Schedule it (weekly or biweekly) so it’s consistent.
• Step 3: Treat it as non-negotiable in both your business and personal budgets.

Working backwards from lifestyle needs also creates clearer revenue and pricing strategies. If you know what you must pay yourself, you can set sales targets that actually support it instead of hoping your pricing “works out.”

Set time-bound targets (financial goals in 2026)

Time-bound goals improve accountability. Don’t just say, “I want to make more.” Set financial goals in 2026 with a date and a number, then align your pricing and sales plan to match.

4) Build a Support Circle: Advisors, Books, and Free Resources

Start with one trusted person (and be fully honest)

I don’t believe you have to fix your money story alone. You also don’t have to announce it to the world. But you do need someone in your corner—your spouse or partner, a financial coach, or a trusted advisor—so you can talk through the real numbers without shame.

Jen Perez: “You just have to be open to that, build that trust... do it not with some random stranger, but with someone you trust.”

When I meet with an expert, I bring the full picture: debts, late payments, cash flow issues, and the “one huge thing” I’m tempted to hide. If I leave details out, I’m blocking the solution.

Jax Crider: “If you start hiding some things, then the whole reason we want to know all the details is so we can better help you.”

Use books and podcasts to bridge the gap

Sometimes I just need a simple explanation before I’m ready to ask better questions. That’s where self-study helps. Books and podcasts can close knowledge gaps fast and make conversations with lenders, accountants, and advisors less stressful.

• Mortgage One-on-One (Jax Crider) for home-buying basics and lender language
• 69 Ways Money is Like Sex for mindset, communication, and money confidence

This mix—learning on my own plus getting coached—has been the quickest path to financial readiness and stronger access to funding.

Tap free and low-cost financial literacy resources

We’re living in a time with more free or low-cost education than ever. If budget is tight, I start here and build momentum.

• SBA and SBA partners often provide small-business-focused financial literacy resources, templates, and courses
• Local small business development centers and “centers of excellence” that offer targeted support
• Financial literacy workshops (including specialized tracks and workshops for women entrepreneurs)
• Online classes and community sessions that function like entry-level financial literacy training

My “support circle” checklist

1. Pick one expert I trust (not a random stranger).
2. Share complete details so they can actually help.
3. Pair coaching with self-study and workshops for faster progress.

5) Wild Cards: Games, Spicy Analogies, and Tiny Experiments

Money and sex have something in common: they’re both taboo topics. That’s why I love Jen Perez’s line, because it gives me permission to bring a little humor into a tense room.

Jen Perez: "I wrote my book called '69 Ways Money is like Sex' because they're both taboo topics."

When I’m building a financial literacy program for entrepreneurs, I don’t start with spreadsheets. I start with feelings. A friend once told me I’m like going to a gynecologist for the first time: the unknown, the fear of being judged, and the awkward “what happens behind closed doors?” vibe. That’s exactly how many founders feel when they open their bank feed or look at their profit and loss statement.

Jax Crider: "A lot of it is more deeply rooted in a shame factor... people feel like if they take a look they don't understand."

A 30-Minute “Money Gynecologist” Check-In

I run a time-boxed, no-drama session that makes money review feel normal. For 30 minutes, I use a simple checklist: cash balance, bills due, top spending categories, and one “what surprised me?” note. The rule is no judgment, only clarity. Framing matters—when it feels playful (even a little spicy), people show up and stay present.

Prototype a Team Workshop with Financial Literacy Games

Interactive approaches boost engagement and retention, so I like to test financial literacy games in team meetings. I run three quick rounds where we score points for clarity, not perfection: (1) explain this month’s numbers in plain language, (2) check if spending matches the budget, (3) name one action item for next week. It’s a low-stakes way of learning practical money skills together, and it turns “finance” into something we can actually talk about.

Tiny Experiments That Build Confidence Fast

Instead of big overhauls, I run small tests that are measurable and easy to repeat: a 14-day spending fast, a small price increase test, or a 30-minute weekly finance huddle. These tiny experiments are scalable and low-risk, but they compound. Each one reduces fear, improves cash flow decisions, and makes the next money conversation less awkward—until “checking the numbers” feels as routine as any other part of running the business.