In this special episode of the Buying Online Businesses podcast, Jaryd Krause sits down with Michael Frew, M&A advisor at WebStreet (formerly Empire Flippers Capital), to answer those exact questions—and more. Michael’s journey is a masterclass in strategic growth: from buying his first Amazon affiliate site to managing a multi-eight-figure portfolio of digital businesses across SaaS, e-commerce, content, and ad-based models.

With a background in business, economics, and over 20 years in software development, Michael brings a rare blend of technical and financial insight into what makes a great acquisition—and what to avoid at all costs.

In this episode, you will learn:

How do you assess your budget and decide the right entry point for buying a business?
Why can some deal structures kill a deal, and what works better?
What did Michael’s multiple acquisitions teach him about risk, leverage, and operational focus?
The evolving role of AI in online business—and whether it’s a threat, an opportunity, or both.

Packed with insights from someone who’s seen it all, this episode is essential for first-time buyers and seasoned investors.

Now, let’s dive in!

Episode Highlights

05:00 What Does It Mean to Buy an Online Business?

08:25 Challenges Faced When Buying Your First Online Business

14:50 Financing Your First Business Purchase

21:00 Lessons Learned from Multiple Acquisitions

27:30 Systems and Automation for Business Growth

32:40 Adding Value After Acquisition

38:00 Avoiding Common Mistakes in Business Acquisition

Key Takeaways

➥ Buying an online business offers a shortcut to entrepreneurship with established revenue streams and growth potential.

➥ Conducting thorough due diligence and evaluating financials are critical to making a successful online business acquisition.

➥ Acquiring multiple businesses diversifies risk and increases cash flow by expanding your revenue sources.

➥ Learning from multiple acquisitions helps streamline processes, identify successful strategies, and integrate businesses efficiently.

➥ Effective delegation and building a strong team are key to managing multiple businesses successfully.

About Michael Frew

Michael Frew is the M&A advisor for Webstreet which was formerly Empire Flippers Capital. He received his B.S. and MBA in Business and Economics while studying in China, Hong Kong & The Netherlands, as well as several post-graduate information security certifications.

Having been a successful software developer and consultant for two decades, he pivoted to collaborating with other developers on small side projects to help them gain traction and grow their bootstrapped businesses.

This led to a deep dive into the niche world of digital business M&A. What started with the acquisition of a small Amazon Affiliate site led to managing an eight-figure portfolio of e-commerce, SaaS, content, and advertising businesses a decade later. Michael's business acquisition insights have been featured in dozens of media outlets like FE International, Indie Hackers, and Empire Flippers.

Connect with Michael Frew

➥ https://www.michaelfrew.com

➥ https://content.devdrivenacquisitions.com

Resource Links

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

➥ 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

➥ Cloud Ways (Website Hosting) - https://bit.ly/40tjyjG

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

➥ Market Muse (Content Marketing Software) - https://bit.ly/3Me39L0

🔥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

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

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