My Favorite Mistake — 180: Tech Expert Dave Sobel “Really Screwed Up” His First Company Acquisition

Host of the Business of Tech podcast, and owner of MSP Radio

Episode page with video, transcript and more

My guest for Episode #180 of the My Favorite Mistake podcast is Dave Sobel. He’s the host of the Business of Tech podcast, and owner of MSP Radio.Dave is regarded as a leading expert in the delivery of technology services, with broad experience in both technology and business. He owned and operated an IT Solution Provider and MSP for over a decade, both acquiring other organizations and eventually being acquired.

“The Business of Tech” is a leading IT services focused news and analysis podcast and YouTube show, with thousands of listeners and subscribers. He also co-hosts of the podcast “Killing IT”, and authored the book Virtualization: Defined.

Dave holds a bachelor’s degree in Computer Science from the College of William and Mary. He lives just outside Washington DC with his wife and two cats. His interests include travel and food, cheering the Washington Nationals and Capitals, and smoking barbeque… He was introduced to me by Jason Levin, my guest in Episode 161.

In this episode, Dave tells his favorite mistake story about “screwing up an acquisition really bad.” Why did he not really understand the full situation of the company? Was it too late to make adjustments to the business after buying it? How did he apply the painful lessons learned when he sold his company in 2011

We also talk about questions and topics including:

  • Why did he start a company?
  • What he learned about being laid off from startups as a tech person
  • Spent more time on the “paper” and not enough on the “people”
  • Was it too late to make adjustments?
  • Did you acquire other companies?
  • Sold his business in 2011
  • Applied the lessons learned… was a complete open book instead of withholding information like his seller had
  • Mistakes that small businesses make in choosing technology?
  • Examples of companies choosing software or tech because it’s trendy?
  • How often is the mistake about HOW they implement it?
  • The *delivery* of the tech is super important

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