The Reboot Quest

“It may be that when we no longer know what to do, we have come to our real work and when we no longer know which way to go, we have begun our real journey.” - Wendell Berry
Dates TBD

Know you're not alone. Join us for our The Reboot Quest.


  • "The two words that best capture my Reboot Quest experience are clarity and connection. The exercises and ceremonies helped me feel emotionally clear and the fasting surprisingly helped me feel physically clear. In that state, I was able to "clear my pipes" of remnants from my past that were still holding me back today. And then, I was able to clearly envision what I genuinely want out of my life, now and in the future. This was the clarity I sought from my quest and it was only possible through connection. Throughout the week, I felt deep connection with our wise and skillful guides, Jim and Jade, with the other questers, who all fully showed up with openness and vulnerability, and with Mother Nature, who supported us in a way I can only describe as energetic. I am very grateful for this life-changing and life-affirming experience and would recommend Reboot Quest to anyone who is seeking the support and connection to have clarity in their lives."

    Greg Tseng

    Greg Tseng

    Co-founder and CEO of Tagged

  • "As a lifelong skeptic of touchy-feely methods to answer complex questions, I wasn’t sure the Vision Quest was going to do anything for me. I gave it a shot because I wasn’t making progress any other way. I found that just like computers resort to heuristics for computationally intractable problems, people can tap into emotional and physical heuristics to help solve complex personal challenges. The Vision Quest provided a structure for employing these unfamiliar tools, and (despite my skepticism) I came home with a much clearer vision of what was truly important to me, as well as the tools to make that vision actionable into a more joyful and fulfilling life. I would highly recommend this experience to anyone stuck in a life challenge that resists rational solution - for this engineer, the Vision Quest was transformational."

    Tom Shields


  • "Once I began to realize how valuable this work is, I went all in...And I came back with some pretty deep insights that I predict will help me be more joyful, more fulfilled, and more successful. I have a lot of work still to do, but I know the way forward, and I’m no longer stuck in a rut. I think a Vision Quest can be a deeply rational structure for addressing life challenges, and a path to becoming more joyful and fulfilled."

    Tom Shields

    Tom Shields

    Programmer and Entrepreneur

Are you in the midst of a major life change and feeling alone in that quagmire of feelings? Are you longing for more meaning in your personal or professional life? Or are you already in the midst of the turmoil and excitement of a business or role transition? If so, join us…

The Reboot Quest is truly a one-of-a-kind experience to support startup CEO’s, founders and other leaders who are confronted with personal and professional questions that won’t go away. Questions like “What’s next for me?” “What am I really here to do?” “Who am I really beyond my business identity?” “What if I really lived the life that is mine to live?”

Designed for members of the startup community who are in the midst of change or sense it coming.  If you are experiencing that maybe you long to enrich your personal life as much as your business world but don’t know where to turn. This life-changing experience is based on the arc of a journey of transformation in which we acknowledge what is ending, dying or being shed so that we can more clearly see and welcome what is coming forth.  In our return, we will recognize a more authentic self-emerging and will see more of our true work to do in the world.

This quest has its roots in a traditional pan-cultural rite of passage sometimes called a Vision Quest; a remarkable ceremony that people have turned to for support in difficult times throughout history. It is a return to nature as teacher and as a mirror for our truest selves. It’s a journey that supports our wholeness as human beings, helping us to better understand and embrace parts of ourselves we may have ignored, misunderstood, hidden or judged, and the unique artistry, gifts, and authentic voice we have to bring forth in our lives and in our work. Humans who have embraced this wholeness make better leaders.

The impact that can come from this journey can be understood in the shifts in our own identity and self-awareness for who we are and who we’re becoming, how we show up in our relationships, how we are to lead the work we are a part of and living a unique and authentic life.

Do you love yourself enough to listen with the ears of your heart to the other voices of yourself speaking? – Beno Kennedy

We know the transformative power of the wilderness intrinsically here at Reboot. Jerry’s Vision Quest, led by our own Jim Marsden and Jade Sherer, whom you’ll meet on this special episode of the podcast, was a pivotal moment for him. (In fact, it’s Jerry who cries in this episode.)

So when our heart started beating fast and our palms got sweaty as we talked about designing a Vision-Quest-type-Bootcamp for startup leaders, we leaned.

This is your opportunity. Are you hearing the call?


Startup CEO’s, business leaders, or founders experiencing significant change in their life or the sense of impending and momentous personal shifts. 8-10 participants will be led by Reboot’s Jim Marsden and Jade Sherer, who’ve been guiding quests for more than 30 years combined, through a rigorous yet restorative nine-day adventure. This program is limited to 10 participants.


2019 dates to be determined.


Like the “vision quest” of many indigenous cultures, this contemporary approach is rooted in dedicated time in wild nature and we’ve chosen a special, wild location near majestic, Great Falls, MT.


The cost is $7000, and includes the following ($100 extra for a shuttle to and from the nearest airport):

  • All meals from arrival to departure
  • Retreat center accommodations
  • Guide fees, insurance, and permits
A non-refundable deposit of $1, 000 is due upon acceptance to the program.



Participants will be invoiced $1,000 upon acceptance into the program. If you have questions about the quest, reach out to and

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