Sheila and Bill Blakeslee (Blakeslee Vineyard Estate)

“I knew I could make it work, I just knew I could.” Wine-making is a tough business. Competition is abundant, and the capital requirements are enormous. Despite these challenges, the Blakeslees have created a thriving winery and vineyard, and I know they have a lot of local fans in Sherwood and the surrounding areas. This episode focuses on how Sheila and Bill went about creating their own winery and vineyard. Probably it’s fair to say that this episode is 80% about the business, and 20% about wine (whereas my previous interview with Jared Rallison was closer to 80% focused on wine-making, and 20% business oriented). I think both episodes are good in their own right, especially since they cover different aspects of the industry.

Subscribe on iTunesGoogle PlayOvercast, or Stitcher.

Topics Discussed:

  • Creating a beautiful vineyard
  • Bringing in outside experts
  • Dry-farming
  • Previous business ventures (Bilet Products Co and Ceragem International)
  • Managing working capital in a wine business

Both Sheila and Bill are great examples of the kinds of people I want to learn from through Why Try.

Sheila and Bill Blakeslee came to wine-making after retiring from successful careers as entrepreneurs. Since buying the property in 2005, they’ve created an absolutely beautiful vineyard. Specifically, Sheila is a master of creating a fun and welcoming customer experience, and generously hosts a variety of events at the vineyard ranging from a Wings Over Wine release of a red-tailed hawk, to meet-ups for the Women of Willamettenetworking group, and a number of fun summer events for wine-club members. Something I thought was pretty unique was how 4 out of 5 Yelp reviews mention Sheila by name out of appreciation for the experience she provides.


Then, on the business side of things, Bill has figured out how to make one of the most challenging, competitive businesses (ie a winery and vineyard) produce consistent, positive cash flows. After all, Bill has many, many years of experience in running capital intensive businesses, having founded a company that manufactures wooden pallets in 1973.  His insights are worth listening to.


Thanks again to Sheila and Bill Blakeslee for taking the time to do this podcast episode with me. You can find their business Blakeslee Vineyard Estate at, and on Facebook under Blakeslee Vineyard Estate.

Music for this podcast comes from a ragtag band of spell-flinging sorcerers…In Space! Check out Cambrian Explosion on Facebook under Cambrian Explosion. If I’m not mistaken, they have a show coming up on September 2nd, and you can learn more about it there. You can also find their music on itunes, spotify, and

You can find more episodes like this one at where you can subscribe to the podcast, or stream episodes in your browser. You can also get new episodes by hitting subscribe in your podcast app. Also, check out Why Try, the Podcast on Facebook, for updates on new episodes, photos, etc. Why Try the Focus Group is still going strong, so if you want to be more involved in the podcast, consider joining that Facebook group. Thanks for listening.

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