#21 - Don’t Be That Guy - Cash Flow Challenges for MSPs (Nicholas Reimer – Alternative Payments)

In this Don’t Be That Guy episode of the BMK Vision Podcast, Josh Peterson and Ryan sit down with Nicholas Reimer (Partnerships Manager at Alternative Payments) to unpack an uncomfortable truth in MSP operations: cash flow failure is rarely caused by “bad clients” alone—it’s usually caused by undefined financial expectations, gaps in the quote-to-cash journey, and a tolerance for manual friction that quietly compounds. This conversation connects directly to the leadership discipline behind Vision, and it pairs well with resources on stabilizing recurring revenue inside ConnectWise agreements and automating billing and invoicing workflows.

This is not a conversation about accounting tricks or “getting better at collections.” It’s about operational clarity. Nicholas explains what their data shows across hundreds of MSPs: many businesses are still getting paid weeks after invoices are due, and the root cause isn’t a single failure point—it’s a chain of small handoffs where momentum dies. Ryan reinforces the hard lesson most owners learn late: a company can be profitable all the way to bankruptcy, because profit on paper does not fund payroll, hardware purchases, or growth until the cash is actually in the bank.

If you’re trying to scale past the “small MSP” stage—where projects grow larger, hardware exposure increases, and a single delayed AR cycle can create a payroll crisis—this episode is a reminder that financial maturity is operational maturity. The goal is not to become “more aggressive.” The goal is to remove ambiguity, eliminate unnecessary gaps, and build a cash-flow system that matches the level of responsibility you carry for your team.

Why do “profitable” MSPs still run out of cash?

Because profitability and liquidity are not the same thing. MSPs can show strong net income while cash is trapped in receivables, delayed approvals, unbilled projects, or messy reconciliation between the PSA and accounting system. The business looks fine—until the bank account disagrees.

In the episode, Ryan frames the core danger simply: your books can say you have the money, but until it’s in the bank, you can’t spend it. That gap becomes existential when your payroll is real, hardware must be purchased upfront, and large projects create short-term cash exposure.

• Cash flow is the operating oxygen of the MSP—not a finance “nice to have”
• As MSPs grow, project size and hardware exposure increase faster than financial discipline
• Manual billing and AR workflows hide risk until it shows up as a crisis

What the data says: AR delays are still common in MSPs

Nicholas shares a blunt industry reality: across a large MSP sample, many providers are effectively getting paid well after the due date. Even when services are recurring, the cash cycle is often “invoice sent” → “client forgets” → “follow-ups” → “eventual payment,” which turns predictable revenue into unpredictable cash.

The strategic takeaway: if your MSP’s delivery model is recurring, your cash collection model should be recurring too. Autopay and systematic reminders aren’t “pushy”—they are the operational equivalent of monitoring and patching in your technical stack. You don’t wait for a server to fail before you care about uptime.

How do you reduce the “gaps” that break the quote-to-cash journey?

Most cash flow failures aren’t caused by one big decision. They’re caused by handoffs. A quote gets signed… but payment details are never captured. An invoice gets generated… but the client isn’t enrolled in autopay. A project starts… but the deposit wasn’t collected. In each gap, momentum dies—and the MSP absorbs the risk.

Nicholas describes the end-state as a quote-to-cash model: the moment a customer says “yes,” the financial system is set—billing terms are clear, payment details are captured, and recurring payments are automated so the business doesn’t rely on memory, follow-ups, or heroics.

• Remove optional steps that allow customers to “forget” the payment setup
• Use automation to reconcile PSA + accounting so payments are recorded cleanly
• Design onboarding to include financial setup as a first-class milestone

Should MSPs pass credit card fees to clients?

The episode lands on a mature middle ground: offer options and be transparent. When clients understand that convenience has a cost, many will choose ACH. Others will choose cards because points and internal processes matter to them. The key is to avoid hidden fees and avoid ambiguity—clarity builds trust.

As a leadership principle: you are allowed to run a financially disciplined MSP. If you treat margin and cash flow as optional, you’re not being “nice”—you’re making your team carry unnecessary risk.

Why deposits and financing matter more as you scale

Ryan highlights what changes as MSPs grow: you move from small, manageable billing cycles into projects that can demand hundreds of thousands in hardware and delivery costs. If your line of credit renewal slips, if a customer delays a payment, or if you’re carrying hardware without a deposit, you can end up financing the client’s project with your own cash.

Nicholas frames financing tools as a strategic “option” that can protect relationships: when a client wants a major upgrade but cash timing is tight, financing can prevent a project from stalling while still getting the MSP paid on time.

Episode highlights

• Why an MSP can be profitable all the way to bankruptcy
• How small “gaps” in onboarding quietly create massive AR problems
• Passing card fees the right way: options, transparency, and trust
• Deposits, lines of credit, and hardware exposure as the MSP scales
• Why cash flow discipline is part of leadership—not just bookkeeping

About the guest: Nicholas Reimer

Nicholas Reimer is the Partnerships Manager at Alternative Payments, working with MSPs to improve accounts receivable reliability through payment automation, streamlined client options (ACH and cards), and a tighter quote-to-cash experience. He brings a practical perspective on how billing friction, AR delays, and unclear financial onboarding can quietly undermine otherwise strong MSP operations.

Connect with Nicholas Reimer on LinkedIn →

About the host: Josh Peterson

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast, where he and Ryan explore the leadership, execution, and financial discipline required to build enduring MSP businesses.

Connect with Josh Peterson on LinkedIn →

Frequently asked questions

What’s the fastest way for an MSP to reduce AR stress?
Eliminate manual follow-up as the “system.” Capture payment details early, automate recurring payments where possible, and reduce gaps between quote signature, invoicing, and collection.

Why do MSPs struggle with cash flow as they grow?
Project size and hardware exposure scale faster than financial process maturity. Without deposits, disciplined terms, and clean PSA/accounting reconciliation, growth increases risk instead of reducing it.

Is passing card fees to clients a bad customer experience?
Not if it’s transparent and framed as an option. Offer no-fee ACH, clearly disclose card fees, and let the client choose convenience versus cost.

What does “quote-to-cash” mean in an MSP context?
It means the customer’s “yes” triggers a complete financial workflow: agreement terms are clear, payment details are captured, invoices are generated consistently, and collections/reconciliation are automated so cash flow becomes predictable.

Related resources

• Recurring revenue in ConnectWise: how to set up agreements that don’t break later
• Automating billing & invoicing in ConnectWise Manage (step-by-step)
• Why you’re not paying enough attention to agreement gross profits

Want to continue the conversation?

If you’re an MSP owner who wants cash flow to stop being a recurring source of stress—and instead become a predictable outcome of clean execution—we’d love to connect. Explore the Vision operating system or apply to be a guest on the podcast.

👉 Apply to be on the BMK Vision Podcast
👉 Learn more about Vision