Why Contractors Go Broke (And How to Stop It)

Why Contractors Go Broke (And How to Stop It)

A contractor trying to bank money without a proper system
Chris Lonergan
Chris Lonergan April 2, 2025

Are late customer payments and slow cash flow keeping you up at night? You’re not alone.

Many contractors struggle with getting paid on time—and it’s killing their companies. Let’s talk about cash flow killers and how to fix them so you can keep your business afloat.


Today, we’re tackling one of the biggest problems in the industry: cash flow. Let's break down the most common cash flow killers and show you how to fix them—so you can get paid faster and keep your business running smoothly.

Late Payments & Unpaid Invoices

Chasing down payments is one of the most frustrating parts of running a contracting business. You finish a job, send the invoice, and then… nothing. Days, even weeks go by, and the check is still "in the mail."

A lot of contractors still rely on paper invoices and checks. Paper checks can take days to arrive, and even longer to clear.

Clients are way more likely to delay payments when they don’t have an easy way to pay.

And every day you wait for a check to clear is a day you’re not reinvesting in your business.

You need to move your business to a system that lets clients pay online via credit card.

Instead of waiting on checks, you can send payment links instantly via email or text. With online payments, you:

  • Get paid faster—no more waiting for checks.
  • Reduce awkward payment conversations
  • Make it easier for clients to pay—leading to fewer delays.

That means you can get paid in an instant when the job is done... and the faster you get paid, the smoother your business runs.

Inconsistent or Irregular Billing

Many contractors lose money simply because they don’t invoice consistently. Delayed invoices lead to delayed payments—clients forget, deprioritize, or even lose track of what they owe. Without a system in place, cash flow becomes unpredictable, making it harder to cover expenses, payroll, and materials.

Why This Happens:

  • Invoices are sent late (or forgotten entirely).
  • Clients don’t get follow-up reminders.
  • You’re busy - Back-to-back jobs make manual invoicing overwhelming.
  • Relying on paper or spreadsheets instead of an actual payment system.

Set up online invoicing. By digitizing your billing process, you can ensure invoices go out on time and payments come in consistently.

  • Automated Invoicing: Schedule invoices to send immediately after project completion.
  • Recurring Billing: Easily charge for subscription-based services like recurring maintenance plans or safety clubs, a great source of steady income for your business

Inconsistent invoicing leads to inconsistent cash flow. Having the right systems in place ensures you never forget to bill a client—and always get paid on time.

Disorganized Financial Tracking

When you’re manually tracking payments—or using outdated systems like spreadsheets or paper invoices—it’s easy to lose track of what’s owed. Unpaid invoices slip through the cracks, leading to cash flow problems and unnecessary financial stress.

This happens because…

  • Payments aren’t logged in real-time, making it hard to track outstanding balances.
  • Paper invoices or spreadsheets create room for human error.
  • No centralized system means scattered records across emails, notes, and different platforms.

That’s why you need a business dashboard to track invoices, payments, and outstanding balances in real time. With automated tracking and clear visibility, you’ll always know who owes you money—and when it’s due.

Missed payments due to financial tracking issues add up fast and make the difference between operating your business comfortably and risking unnecessary loss.

How the Footbridge Dashboard Solves These Issues

The more moving parts you have, the harder it is to easily run the money part of your business. Don’t make it harder on yourself. You don’t have to struggle with cash flow.

There are a lot of systems out there that handle some parts of this problem, but most of them aren’t designed specifically for contractors and home service providers.

That’s why we’ve custom-developed the Footbridge Dashboard as part of our updated contractor marketing program.

It’s an online business management dashboard that makes it easy to get paid faster, track payments, and keep your business financially stable.

  • Accept credit cards instantly
  • Automate invoicing
  • Have a single portal for managing how your business gets paid

If cash flow issues are holding your business back, it’s time to modernize how you handle payments. The Footbridge Dashboard makes that possible - all without contracts, expensive per-user costs, and more.

"Contractor Marketing Tips And Tricks" - The Footbridge Media Podcast

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