From Corporate Sales to CEO: How Keith Found Freedom in Business Ownership - Keith Sklarsky

Episode Summary

In this episode, Matt sits down with former client and business owner Keith Sklarsky to explore his journey from corporate sales to successful business ownership. After leaving a demanding career in sales management, Keith found his path in business acquisition, purchasing multiple businesses and leaving Corporate America behind.

Keith shares how he navigated the transition into entrepreneurship, including his experience with financing, the due diligence period, and finding "off the market" roll-up opportunities — all while successfully managing multiple businesses. He reveals key insights about building strong partnerships, empowering employees, and balancing business growth with family life.

Whether you're exploring your first acquisition or looking to scale your portfolio, this episode is packed with practical insights and valuable lessons from someone who's done it — and done it well!

 

Timestamps

[00:00] Welcome & Introduction

 

[02:06] Leaving corporate life for business ownership

 

[04:01] Did you keep your corporate job as you transitioned into business ownership?

 

[06:01] How did you find the first business you purchased, and did you use a broker?

 

[10:33] What is an "add-back"?

 

[14:05] Finding and buying an "off-market business"

 

[14:54] Key considerations for buying a business

[20:43] How to get a broker's attention

 

[23:30] Picking the right business (avoiding purchasing a business out of town)

 

[26:33] Purchasing your third business — what did you learn? What would you have done differently?

 

[30:13] Having enough operating capital as you step into a newly acquired business

 

[36:02] What's next for Keith?

 

[37:00] At what point will you need to expand your management team to keep up with your growing portfolio?

 

[39:07] Managing ownership and family/personal life

 

[41:37] Who made a difference in your life and helped you become the business owner you are today?

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