Why Some MSP Owners Stay Broke

Why Some MSP Owners Stay Broke

From The Ray J. Green Show by Ray J. Green

May 13, 2026 · 8 min

About this episode

This episode discusses how defensive hiring decisions among MSP owners can lead to stagnation and the importance of investing in sales for business growth.

A lot of MSP owners think they’re making “safe” hiring decisions when they delay or minimize sales investment. But many of those decisions are actually driven by a hidden assumption: that sales won’t materially change the business. This episode examines how defensive thinking creates growth ceilings, why underfunded sales hires often fail by design, and how strong MSPs use sales to expand the size of the business instead of protecting the size of the budget. What You’ll Learn in This Episode Why hiring sales based only on today’s budget creates long-term stagnation How “safe” decisions quietly reduce the odds of sales success The difference between businesses that protect revenue and businesses that create it // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. About Ray: → Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more. → Former CEO operator for several investor groups where he led turnarounds of recently…

People in this episode

Host: Ray J. Green

Topics covered

  • MSP owners
  • sales investment
  • business growth
  • hiring decisions
  • sales success

Keywords

  • MSP owners
  • sales investment
  • business growth
  • hiring decisions
  • revenue protection

Mentioned in this episode

Organizations: U.S. Chamber of Commerce, MSP Sales Partners, Repeatable Revenue Ventures

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