The Hardest Dealership to Buy Is the First One

September 9, 2025
Everyone dreams of owning a store. Few understand what it really takes.
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Most people in automotive talk about growth in units or revenue. Gerrick Wilkins talks in terms of entire dealerships. After 20+ years running stores himself, Gerrick now leads Omega Advisors, helping dealers buy, sell, and scale their groups the right way.

In this conversation, he explains why getting your first store is the hardest, how family legacy transitions can create unexpected tax traps, and why he believes the franchise dealer model will only get stronger in the face of disruption. For anyone thinking about acquisitions, succession, or the future of retail auto, Gerrick’s perspective is both practical and energizing.

Takeaways

0:00 Intro — Meeting Gerrick Wilkins at NAMAD

0:41 From dealer to CEO of Omega Advisors

1:46 How running stores shaped his approach to valuations

2:53 The capital challenge: why buying your first store is the hardest

3:38 Why Gerrick wants to sell clients their 3rd, 4th, and 5th stores

4:01 Legacy dealers, succession, and the tax traps no one talks about

4:59 How the next generation of dealers is more aggressive about growth

5:13 What COVID forced dealers to innovate — and why tech stuck

6:07 Will direct-to-consumer shrink the dealer count? Gerrick’s take

6:49 Why hometown dealers beat DTC on service and community

7:19 A personal story: how a local Honda dealer saved his daughter’s day

8:17 What sets Omega apart: advice from former dealers, not just MBAs

9:46 Why buying a store should mean making more money, not less

10:50 Where to find Gerrick and Omega Advisors

Connect with Gerrick Wilkins at https://www.linkedin.com/in/gerrick-wilkins/

Learn more about Omega Advisors at https://omegadvisors.com/

NAMAD Sessions is brought to you by Mia and produced by the More Than Cars Media Network - https://www.mia.inc/

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