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What Are You Willing to Give Up?

A SaaS Founder's Hardest Question

Scale To Freedom
Episode 19

Most People Get "SaaS Freedom" Completely Wrong

9th July 2026  •  Scale To Freedom  •  Kelvin Holliday

IMany entrepreneurs dream of creating a software business that runs without them — imagining automation, AI, and recurring revenue will finally buy back their time.

But the reality of scaling a SaaS business is very different.

In this episode of Scale to Freedom, Kelvin Holliday sits down with Gary, founder of myCRMsim, to uncover the real journey behind building, scaling, and evolving a SaaS company.

Gary shares how he built myCRMsim from solving his own agency problem, why he rebuilt the entire platform when it outgrew its original structure, and the sacrifices required to create something meaningful.

This conversation goes beyond technology it explores leadership, building remote teams, using AI effectively, and understanding what you're truly willing to give up to achieve your version of freedom.


WHAT YOU’LL DISCOVER IN THIS EPISODE:

00:00 — Gary’s journey from agency owner to SaaS founder and his definition of true freedom.

02:30 — How building a business around family values and personal priorities shapes success.

05:00 — The reality behind building a SaaS company and why freedom requires more than just technology.

10:00 — Lessons from scaling myCRMsim, hiring teams, and overcoming growth challenges.

15:00 — Building a remote global team and creating an AI-first business culture.

25:00 — The biggest question every entrepreneur must ask: “What are you willing to give up to achieve


Connect with Kelvin Holliday:

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