The ZenFounder Couples Retreat Is For Tech Entrepreneurs And Their Partners

If you are a tech entrepreneur or you vicariously observe them, no doubt it’s hard out there at times.  While startups are not for just anyone — statistically, less than 1% of Minnesotan’s will even try  — it always helps to have camaraderie and companionship along the way.

The ZenFounder Couples Retreat was created by Sherry & Rob Walling to address the growing relationship and familial  challenges which inevitably occur in modern entrepreneurship.  In fact, a large-scale study of mental health found that entrepreneurs and their spouses were more likely to be prescribed anxiety medication than a matched control group of 9 to 5ers (non-entrepreneurs).

“It’s no surprise that entrepreneurship can create anxiety,” she says. “What is most interesting is the science says that it can be contagious, also affecting entrepreneurs partner adversely.”

Dr. Sherry Walling is a Minneapolis-based clinical psychologist who specializes in working with founders and CEOs; you may recognize her from our Candor podcast.   She has professionally trained at Yale, Fuller, and Boston University, in addition to seventeen years of experience in the start-up world through her marriage to serial software founder, Rob Walling, the cofounder of Drippurchased by LeadPages last July.

Together with their two boys, ages 11 and 7, the Walling’s uprooted from California to Minnesota one year ago this month and continue to build and reinvest locally.


The first of it’s kind couples retreat happens this fall, Sept. 29 – Oct. 1, at Oak Ridge in Chaska across 130+ acres of sprawling lakeside serenity:

“Two and a half days of quality time, in a beautiful place, surrounded by a small group of entrepreneurs and better halves. We’ll gather from all over the country to rest, connect and reflect on the unique relationship challenges that are part of the entrepreneurial life.”

The experience is limited to 15 couples at an all-inclusive cost of $1,200 per person and joining the Walling’s will be two other entrepreneurial couples co-facilitating:

  • Cory & Lindsey Miller — married 6 years, two children:
    • Cory Miller — co-founder of iThemes and The Div, Inc.
    • Lindsey Miller — partner manager at Liquid Web, previously founded her own political fundraising company
  • Shawn & Kay Hesketh — married 22 years, three children:
    • Shawn Hesketh — creator of WP101, the popular WordPress video tutorial series for beginners
    • Kay Hesketh — a former 8th grade science teacher, she worked alongside Shawn in their business, and now home schools their children

“There are unique challenges that come with being a founder family…the stress and isolation is unique…it’s difficult to relate if you don’t live it. The well being of a relationship at home will make or break the business.”


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