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Due Diligence Deciphered: How to Avoid Buyer’s Remorse with Elliott Holland

Due Diligence Deciphered: How to Avoid Buyer’s Remorse with Elliott Holland [Ep.144]

Greg Elfrink September 12, 2023

There’s a lot on the line when you buy a business, so you want to make sure you buy a business that is primed for success. 

An important lesson you need to learn as a buyer is that you can’t take businesses at face value. There’s a lot going on below the surface that you need to uncover.

That’s where due diligence comes in. 

Few people know more about the due diligence process than Elliott Holland. Elliott is the Co-Founder and CEO of Guardian Due Diligence, a diligence solution for first-time buyers and self-funded searchers.

In this episode, Elliott takes us on a deep dive into the due diligence process. 

He highlights red flags buyers should look out for, the common mistakes buyers make, and he breaks down the due diligence process, step by step. According to Elliott,

“There are four main buckets of due diligence in online business. Financial, Operational, Commercial, and Online metrics. In online business, 70 to 80% of due diligence is focused on financials. Financials are created through the operations of a business, and so they are a great way to really understand the story of the business.”

Elliott also shared his top due diligence war stories and the lessons buyers can learn from them.

If you’re in the market to buy an online business, this episode is jam-packed with useful information that could make or break your acquisition!

Listen to The Opportunity Podcast Episode #144

  • Apple Podcast
  • Google Podcast
  • Spotify Podcast

Topics Discussed in This Episode:

  • Elliott’s background and how he became involved in business acquisitions (02:22)
  • What is Quality of Earnings? (14:13)
  • The best time to hire a due diligence service (21:50)
  • The different areas of due diligence (23:09)
  • What Elliott looks at when examining a business’s financials (25:37)
  • How Elliott examines a business’s operations (32:19)
  • The classic due diligence mistake experienced entrepreneurs make (41:54)
  • Top due diligence questions buyers should ask (44:50)
  • Elliott’s favorite due diligence war stories (53:16)


Sit back, grab a coffee, and learn how the due diligence process really works!

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