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Published on:

2nd May 2025

Push Through The Dip (Why Most MSPs Fail to Scale)

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Hey, I’m Ray Green. I’m a strategic growth specialist for B2B companies.

Since this is social media and anyone can claim anything, here’s a quick rundown of my background:


Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where I 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 I led turnarounds of recently acquired small businesses.


Founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com


Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.


Founder of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com


If your MSP growth strategy doesn't make you want to chuck your computer out the window occasionally, it probably won't deliver meaningful results


I'll show you why pushing through that initial resistance leads to outsized returns while "serial starting" keeps most IT businesses trapped on a plateau.


CHAPTERS:

00:00 - Introduction to Growth Challenges

01:47 - Facing Resistance in New Initiatives

02:32 - Real-World Example of Resistance

05:42 - Understanding the Dip

06:42 - The Emotional Cycle of Change

09:33 - Navigating the Dip

11:40 - The Importance of Persistence

20:15 - Final Thoughts and Encouragement

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About the Podcast

Repeatable Revenue
A podcast for online business builders and growth-minded entrepreneurs.

Repeatable Revenue is hosted by Ray J. Green, an entrepreneurial executive who rose from sales rep to CEO of a private equity-backed company, oversaw national small business for the U.S. Chamber of Commerce, and then left the rat race and successfully drove $70k/mo.+ consulting remotely from Cabo.

This podcast is a collection of interviews, lessons learned, and other infotainment to help you build your business... and the best version of yourself.

About your host

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Ray Green