MAY, 2019


Deep Strategy Work.

Reflection & White Space.

Other Founders & Leaders who Get It. 

Restorative Time in Nature. 

This retreat combines these things in the most powerful way possible, so that you can continue to access your greatest capacity  to lead...

To do the meaningful, impactful work you’re meant to do in the world.



The Spring Founders & Leaders Retreat for Men is an all-inclusive, two-and-a-half day retreat that will be held at the Justin Trails Resort, just outside of Sparta, WI, right when the spring flowers will be blooming on the eco-resort’s 200-acres of woodland, meadows, and hills.

During the retreat we’ll focus on three primary themes:

  • ZOOMING UP from the day-to-day details of running a company to the big picture, with important, strategic questions and conversations that will fundamentally shape the future of your life, your leadership, and your company.

  • TUNING IN to who you are as a person, leader, partner, father, and friend; to what matters most and how to cultivate those things as part of your daily rhythms; and to the beauty of nature and its grounding power.

  • CONNECTION & COLLABORATION with a small, carefully-curated group of other founders & leaders who “get it” and are navigating similar challenges, issues, and opportunities and believe in doing the work to get to incredible outcomes.

Each day, we will hold fiercely facilitated deep-dive strategy sessions. Conversations will happen within a framework of support and understanding around the bigness of what you’re carrying and leading. This game-changing deep work will be super-charged by doing it collectively as a community (the likes of which you probably won’t find anywhere else) and will be paired with time for individual reflection and white space.

Early mornings will be reserved for (optional) physical activity and time in nature, while evenings may be spent around a bonfire or doing other activities.

The whole retreat will be designed—with your input (via a pre-retreat reflection form)—to be an intentional and thoughtful experience that’s aligned with all the different parts of your life. It will be inspiring, exciting, and profound (I know because I’ve seen it happen before).


In typical founder & leader fashion, your lifestyle is fast-paced. There are so many demands, meetings, to-do lists, and long hours. The responsibility of keeping your company alive and thriving—for a week, a month, a year, ten years— is heavily engrained in you. Every day you wear the pressure of that.

But it’s worth it because you’re doing amazing things in the world and making a positive impact.

Yet, it can be lonely at the top.

You’re doing things no other company has done before, and an ever-growing and expanding team is looking to you as their leader.

Plus, because things move so fast, it’s not the same company it was even a year ago, so you continue to look at your role in context of this growth and wonder:

Who am I now? How do I stay ahead?

You’re willing to ask yourself tough questions to come up with honest answers that will help you see yourself in a new light—to confidently transition to the next level and work toward the next opportunity.

You also want to prioritize your own wellbeing so that you can fully show up, not just as a founder, but as a spouse, family member, and friend—all while doing the other things in life that matter, like tending to your health, or doing that big house renovation (even though it feels like you’re camping in your own home until it’s done...).


This retreat will allow you to address high importance questions that can otherwise get lost amidst all the noise and urgent stuff. You’ll also get to reflect on what your most important work is and how that translates into the greatest value you can provide on a daily, weekly, and monthly basis. You’ll then be able to create a concrete plan with action steps and built-in accountability that will steer you forward.

Plus, you’ll get to connect and collaborate with other men who’ve done the crazy shit you’ve done (you guys know what I’m talking about) in service of making the thing you believe in work.  Your tribe will expand. Your significant other will be thankful that you have other people to talk to about the complex and vulnerable things that come up for you as a founder & leader.

Being in nature will ground you as you reset and exhale. You will go into your next quarter—and beyond—clearer and calmer, and with an even higher capacity to lead and do impactful work. You’ll also re-commit to routines that honor your health and wellbeing as a whole person.




·       Arrival and check-in

·       Introductions, intentions, and design

·       Welcome dinner

·       Evening activities


·       Time for physical activity and nature (optional)

·       Breakfast

·       Reflection and white space

·       Morning deep-dive strategy session

·       Lunch

·       Afternoon deep-dive strategy session

·       Reflection and white space

·       Dinner

·       Evening activities


·       Time for physical activity and nature (optional)

·       Breakfast

·       Wrap-up deep-dive strategy session: making a plan to make it real

·       Lunch

·       Closing circle

Note: Further details for our time together will be informed by the answers you share in your pre-retreat reflection form. You will receive additional information about the schedule closer to the date.


Please plan to make your own travel arrangements to and from Justin Trails Resort and plan to arrive on Tuesday October 9th between 3 and 4:30 pm, and to depart by 1pm on Thursday, October 11th. 

Note: if anyone would like to combine this retreat with a family camping adventure following the retreat, the Justin Trails campsites are available in the days following the retreat. 


Named one of the top ten Eco-Luxury Inns by the Wisconsin Department of Tourism, Justin Trails Resort is nestled in a quiet, peaceful coulee in the heart of the Wisconsin Driftless Region.

Lodging ranges from luxurious farmhouse suites, to shared Scandinavian log cabins, to more rustic camping cabins. Most include whirlpool tubs and fireplaces, as well as other amenities. Feel free to check out detailed descriptions of the lodging options via the Justin Trails website here

An elegant post and beam barn will serve as our meeting place. We’ll also have full access to the 200-acre property—including walking trails and two professional disc golf courses. Bonfires are often lit in the evenings under the open, starry sky.


Meals are prepared on-site with fresh and natural ingredients. Gluten-free, dairy-free, keto, paleo, and vegan diets can be easily accommodated. You'll have an opportunity to share any dietary restrictions or preferences in your pre-retreat reflection form. 


The investment ranges from $2,400 - $2,700 per person (depending on your lodging preference), or $6,000 for a team of three.

All-in-all, you’ll get:

·       Two nights of accommodation

·       Dinner Tuesday, all meals Wednesday, breakfast and lunch on Thursday, and snacks and beverages throughout

·       Mastermind-style deep-dive strategy sessions

·       Time for individual reflection and white space

·       Time for physical activity and nature

·       Follow up resources and materials 

·       A concrete plan with action steps and built-in accountability

·       A virtual, one-on-one follow-up/accountability session after the retreat


This retreat will include a small, carefully curated group of leaders and founders and is invitation/application-only. 


  1. Fill out the application/pre-session reflection form here. 
  2. Pay the $500 deposit via the link below. 
  3. After reviewing your application/pre-session reflection form, I will follow up with you about the retreat, and to confirm your lodging choice. 
  4. Upon confirmation of attendance and lodging, you will submit final payment. 
  5. In the weeks leading up to the retreat, you will receive additional information about the schedule, logistics, what to bring/what to pack, and the possibility of car pooling with others who will be attending. 

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