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

Episode Summary

This in-depth conversation between Bering McKinley, Ryan, Josh, and guest Nicholas Reimer — Partnerships Manager at Alternative Payments — dives into one of the toughest operational challenges MSPs face: cash flow management. Nicholas shares insights from working with over 700 MSPs across North America and highlights how payment automation is changing the financial stability game for service providers.

The discussion covers the evolution from check-based billing to credit card payments, DSO reduction, and quote-to-cash automation. Ryan brings candid stories from his MSP experience — from balancing payment fees and customer relationships to surviving payroll crises — illustrating the real impact of poor cash flow discipline and manual processes. Together, the panel explores AR automation, complex client payment structures, and the critical role of PSA/accounting integrations in building financial health.

Episode Highlights

• [00:01:00] 💰 Alternative Payments is on track to process $1B annually for MSPs.
• [00:06:50] 🏦 Ryan discusses the shift from checks-only to digital payments.
• [00:17:30] ⏳ MSPs are typically paid 20 days past due, driving AR stress.
• [00:20:40] 🔄 Managing deposits and lines of credit for large hardware projects.
• [00:23:40] 🏛 Municipal and education clients still rely on checks, complicating AR.
• [00:32:30] 🔗 How quote-to-cash automation solves MSP billing bottlenecks.
• [00:40:00] 📉 Bookkeeping errors that nearly derailed payroll — and what to learn from them.

Key Insights

💡 Cash flow is the lifeblood of every MSP. Nicholas’ $1B payments projection highlights the sheer scale — and stakes — of financial management in this industry. Ryan’s transition stories and cautionary tales underscore the growing need for automation and transparency in AR workflows.

From reducing Days Sales Outstanding (DSO) to streamlining quote-to-cash integrations, the discussion points MSPs toward adopting systems that protect liquidity and remove friction between sales, finance, and client payments.

For MSPs still managing invoices manually or juggling multiple payment vendors, this episode is a wake-up call: true operational maturity requires financial maturity.

Learn More

For more on financial health and operational maturity in your MSP, explore our related articles: Recurring Revenue in ConnectWise: How to Set Up Agreements That Don’t Break Later, How to Build Profitable Service Agreements for MSPs, and Improving MSP Financial Operations Through Better Data.

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About the Guest

Nicholas Reimer is the Partnerships Manager at Alternative Payments, where he helps over 700 MSPs streamline their accounts receivable processes, automate payments, and improve cash flow reliability. With a background in financial technology and channel partnerships, Nicholas brings a practical, data-driven perspective on how automation is reshaping MSP business models.

🌐 Connect with Nicholas on LinkedIn →

About the Hosts

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast. Alongside Ryan, a former MSP owner and regular contributor, they bring candid and actionable insights for MSP operators striving to master their business fundamentals — not just their technology.

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