Guys Trip: An Intro

How did Guys Trips become a thing? Who is Kyle Depiesse? All this and more in this blog post.


Hi, I'm Kyle.

Here are some quick, get to know you things about me:

I'm from a small town in SE Wisconsin.
I got married to my beautiful bride in 2013.
We have a son, Cal, who runs the show.
I love adventure, health/wellness, corvettes, golf and Jesus.

In my mid 30’s, about 13 years into my Corporate America career climbing the ladder, I hit rock bottom. I found myself caught up in the insatiable quest for more, bigger and better. 

From success at work to possessions at home. I had an “ah-ha” when I realized the tradeoffs I was making to achieve said success, just weren’t worth it anymore.

“For what does a man profit if he gains the whole world but loses his soul?”

After taking the ultimate promotion to a stay-at-home dad in 2017, I started putting the pieces together on what a full life looks like for me. 

The blank canvas I was given to start over allowed me the chance to create a solution to something that would’ve greatly impacted me when I needed it most during my delusional pursuit of self-centered success.

I now measure success in more wholistic ways. In 2020, we left the city and moved to the Northwoods of MN where I found myself in love with a simpler way of life. 

While I enjoy all the conveniences of modern day, I’m a vintage throwback man who craves the solitude and enrichment the Northwoods has given me.

You’ll see me facilitating once-in-a-lifetime Guys Trips all over the world, but I’m happiest splitting wood with an axe at our cabin in the woods. 

Now let's talk about Guys Trip.

There is an undeniable pull on my heart towards the call of adventure.  It’s a chance to explore beyond the boundaries of our comfort zones, venture out into the unknown and embrace a myriad of possibilities.  Many of which, when we adventure, are outside of our control.  

Yet, perhaps the most profound journey we can ever take on is the one that takes place on the inside.  Self-discovery.

One is sexy.  One we often avoid.

But perhaps the most profound transformation that unfolds during an adventure is the metamorphosis of our inner world.  

One you want.  One you need.  

Why not do both?  That’s my belief behind Guys Trip.

The trips I architect, the invitation extends for a 2 for 1.

Two trips at once.  The bucket list one you want, the inner journey you need.

Thank you for reading.  If any of this inspires you or causes you to want to learn more about what we're doing, I'd encourage you to join our Saturday morning newsletter!  You can do that HERE

Cheers to your success! I’m rooting for you.