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Lessons from Running and Growing Multi-million Dollar Online Businesses with Joel Stevenson [Ep.118]

Lessons from Running and Growing Multi-million Dollar Online Businesses with Joel Stevenson [Ep.118]

Greg Elfrink January 24, 2023

Running a big online business can be like captaining a large ship. As the business grows, it can become less nimble and harder to adapt to new trends and changes in the industry. 

But, with the right kind of foresight and knowledge of the online business landscape, you can steer your business to even greater heights. 

This is where Joel Stevenson thrives. With his experience as Vice President of Wayfair and now as CEO of Yesware, an email outreach software, he’s helped take multiple industry giants to new heights of success.

In this episode, Joel gives us a behind-the-scenes glimpse at his approach to growing businesses and explains some of the unique challenges that large businesses face as they scale. We discuss the differences between growing eCommerce vs SaaS businesses, and how to navigate the competitiveness of mature markets. 

Joel also shares details of Vendasta’s recent acquisition of Yesware, explaining how the acquisition came about, and how he worked to make Yesware an attractive asset for interested buyers. According to Joel,

“I really tried to rebuild the company in such a way that it would be acquisition friendly. We tried to have a minimal overhead cost structure. We tried to be very efficient. We paid down a ton of tech debt. My goal was for somebody to see our product, and see that the business itself is in good shape, and know that it would be easy to take it over and really accelerate it.”  

We also dive into why Yesware opted for a stock sale over an asset sale and discuss the appropriate use cases for each option. 

If you want to peek behind the curtain to learn more about the operational intricacies of large online businesses, then look no further!

Listen to The Opportunity Podcast Episode #118

  • Apple Podcast
  • Google Podcast
  • Spotify Podcast

Topics Discussed in This Episode:

  • How Joel achieved incredible business growth at Wayfair (03:02)
  • Joel’s approach to growing businesses and solving problems (05:49)
  • The differences between growing eCom vs SaaS businesses (13:51) 
  • The roles that SEO and SEM played in the growth of Wayfair and Yesware (17:12)
  • How Joel navigates mature markets (22:40) 
  • The story of Yesware’s growth and an explanation of the product (29:15)
  • Vendasta’s acquisition of Yesware (34:46)
  • The differences between a stock sale and an asset sale (44:44)
  • The common mistakes people make when sending out cold emails (48:10)
  • The best piece of professional advice Joel has ever been given or heard (53:37)


Sit back, grab a coffee, and discover what it takes to operate and grow a large online business!

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