Buying Online Businesses Podcast How Acquirers Get Swindled Into Dud Deals Without Understanding Proper Business Due Diligence with Elliot Holland
Strap in for a brutally honest conversation as Jaryd Krause sits down with none other than Elliot Holland, a Harvard Business School alum, seasoned entrepreneur, and strategic founder. Elliot runs a seven-figure due diligence firm that performs "mini audits" on businesses, helping investors avoid being misled by clever sellers and slick brokers.
With nearly 20 years of experience in small business acquisitions, Elliot has seen it all—and then some. From hidden red flags in financials to smoke-and-mirrors marketing metrics on Amazon and SEO-driven sites, he shares exactly where buyers get it wrong—and how those mistakes can cost you hundreds of thousands, or worse, your entire investment.
This episode will pull back the curtain on how unsuspecting buyers get swindled into buying dud deals, all because they skipped real due diligence.
Highlight the critical considerations buyers often miss in the acquisition process:
✔️ The most common (and costly) mistakes buyers make in due diligence
✔️ Why relationships with sellers matter—and how they can go sideways fast
✔️ How sellers can mislead or manipulate the narrative to close a deal
✔️ Financial vs. marketing due diligence—what most acquirers overlook
✔️ The frameworks Elliot uses to assess businesses like an expert
This is not just theory—Elliot has personally helped countless clients dodge bad deals and secure multi-million-dollar wins, all by demystifying the due diligence process. With his signature humor, straight talk, and lived experience, he makes complex business buying principles not only clear but actionable.
Whether you're a first-time acquirer or scaling your portfolio, this episode will save you more than money—it could save your sanity. Don’t even think about buying a business until you listen to this conversation.
Episode Highlights
04:15 – Red flags usually show as many small issues rather than one big problem
10:30 – Verifying seller’s time commitment by reviewing task lists and holding strategy meetings
18:45 – Wanting shortcuts in due diligence can lead to costly mistakes
23:00 – Sellers often resist reasonable buyer requests like strong non-competes and management interviews
26:10 – Negotiation is a strategic dance where sellers test buyer strength
29:15 – Cheaper advisors often bring higher risks and lower value on seven-figure deals
Key Takeaways
➥ Red flags are subtle and require a sharp, skeptical mindset to detect
➥ Sellers use stories and distractions instead of admitting flaws outright
➥ Due diligence takes time and can be uncomfortable but shortcuts are costly
➥ Experienced advisors are critical for high-value deals to avoid disaster
➥ Buyers need to be ready to walk away if sellers are not transparent or cooperative
➥ Emotional detachment helps buyers make better decisions and negotiate smarter
About Elliot Holland
Elliott Holland is a Harvard Business School alum, former business acquirer & OG in small business acquisitions. He runs TheBusinessBuyingMasterclass.com and a 7-figure business that does "mini audits" on businesses before clients acquire them to be sure they're not swindled. With nearly two decades of experience, Elliott empowers everyday investors to acquire million-dollar businesses because he's been in their shoes and offers insight others cannot.
Elliott simplifies complex small business buying concepts with humor so that everyday investors can understand. With over 100 podcast appearances and speaking engagements at top business schools, Elliott shares expertise on entrepreneurship, investing, and business buying.
Connect with Elliot Holland
➥ https://www.linkedin.com/in/elliottholland/
Resource Links
➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com
➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/
➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/
➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/
➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause
➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u
➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld
➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH
🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥
➥ Empire Flippers - https://bit.ly/3RtyMkE
➥ Flippa - https://bit.ly/3wGa8r5
➥ Motion Invest - https://bit.ly/3YmJAmO
➥ Investors Club - https://bit.ly/3ZpgioR
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