Business Acquisition Mistakes Buyers & Sellers Make When Acquiring Online Business with Ross Gerson

Many buyers overlook one of the most valuable yet intangible assets that come with acquiring an online business. 

This episode features Ross Gerson, founder of DealSlide.com and a former broker at Empire Flippers. With extensive experience on both the buy and sell sides of online business acquisitions, Gerson shares key insights into the most frequent mistakes buyers and sellers make—and how to avoid them.

The discussion covers several compelling topics, including Krause’s near-experience as a broker at Empire Flippers, a role Gerson had originally approached him for. Gerson also explains his transition into acquisition advising and consulting, detailing his work with WebStreet and his involvement in acquiring over 15 to 20 content sites.

You will gain valuable insights into critical acquisition mistakes, such as the importance of direct communication with sellers, defining clear acquisition criteria, and navigating the transition period after a purchase. The conversation also highlights Deal Slide, Gerson’s marketplace that aggregates listings from over 20 brokers, streamlining the search process for buyers.

Packed with expert advice, this episode guides anyone looking to buy or sell an online business, helping them maximize their acquisition strategy while setting themselves up for a successful exit.

Let’s get started!

Episode Highlights

03:00 Why Ross moved into online business acquisitions?

11:00 Ross learnings from being a broker at Empire Flippers

19:00 Get an extra from the deal!

25:00 Surprises in the seller's side

39:00 Where to find Ross?

Key Takeaways

➥ Many buyers enter the market without a clear understanding of what type of business suits them best. Taking the time to assess personal skills, experience, and workload preference is crucial. 

➥ New buyers often fear looking inexperienced, but embracing the learning process leads to better decision-making.

➥ Off-market deals are not always better. Broker-listed businesses provide structured deal flow and often undergo vetting, making them less risky.

➥ Some sellers don’t even realize their business can be sold, while others prioritize terms over the highest price. Understanding seller psychology can create win-win deal structures.

About The Guest

Ross Gerson is the Founder of DealSlide.com, former broker at Empire Flippers for 2.5 years acquisition Advisor to WebStreet for roughly 3 years, bought and sold approximately 15-20 content sites for his portfolio

Connect with Ross Gerson  

➥ https://dealslide.com/

➥ https://www.linkedin.com/in/ross-gerson-888ba241/

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/

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause 

➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u

➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM

➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx

🔥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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