Crosscut’s Investment in Coaching, Leadership Development, and Mental Health of Founders
By Brian Garrett, Managing Director and Co-Founder, Crosscut
Around Thanksgiving, I shared stories about my overdue journey of self-care, along with advice for founders who have embarked on entrepreneurial endeavors full of risk, stress and personal responsibility.
Today, I am proud to finally announce how Crosscut and I are putting a financial stake in the coaching and leadership development of our founders.
We are partnering with Evolution, an elite coaching team that specializes in high growth startups. After years of testing their services personally and as a firm, and we couldn’t be happier to bring them into the Crosscut community.
First, let me tell how we got here
I am a hard worker. I have spent the majority of my career relentlessly pursuing opportunities, one after the next, and this has been especially true over the last eleven years at Crosscut.
That focus enabled me to achieve career goals, but over time, I’ve come to realize it was also was a coping mechanism for something deeper. My persistent hustle buried traumatic personal crises and keeping them hidden eventually led to multiple health scares that literally broke down my body.
Two years ago, it became clear: I needed to focus on taking care of myself.
“The last time I saw my father was saying goodbye and kissing his cold, dead body on a metal table in the hospital. Would it be too much to ask for a hug?”
Getting DEEP
My journey to self-care started at a fully immersive leadership retreat called DEEP that is designed to uncover self-awareness as a founder. Our friends at Evolution created DEEP to follow the arc of the Hero’s Journey and although I knew roughly what that meant, I didn’t know what I was truly getting myself into. Still, off I went.
As it turns out, DEEP ended up opening me up to one of the most powerful, healing experiences I’ve ever had. A facilitator asked me, in front of a small group, to have a conversation with my dad and also my sons about the grief I felt losing my dad at thirteen.
Forced to revisit the night of his death, I talked about losing him and told him I missed him, sobbing uncontrollably as I promised my boys that I wouldn’t leave them the way I was left. As the session ended, the facilitator asked me if I needed anything else. I said, “the last time I saw my father was saying goodbye and kissing his cold, dead body on a metal table in the hospital. Would it be too much to ask for a hug?”
And what a hug. He held me and told me he loved me and that he was proud of me. It unlocked my pain and changed me forever.
“Why do I not live in a state of joy with the life and success that I have?”
Emerging from the depths
Ever since I was thirteen, I attempted to turn this painful event into an opportunity, a lesson on how to not take life or love for granted. At DEEP I was confronted with how my pain both fueled my aspirations and shackled my happiness. It affected how I approach my goals.
Rather than engage my grief, I would simply put my head down and work. This strategy worked for a while: I was able to achieve my goals and move on to the next, deflecting the whole way. But there was one important question I simply never asked until I got to DEEP, “Why do I not live in a state of joy with the life and success that I have?”
Obstacles and traumas shape us. I know my trauma shaped me into the businessman, husband and father I am today. I waited too long before stepping back to look at the stories that make me who I am. Ignoring these shadows was keeping me from living to my greatest potential. Facing them with the same intensity and focus I typically reserved for work has put me on a path to a much happier and successful future.
Our commitment to founders: we’re in this together
Starting today, Crosscut commits one percent or more of all capital invested in our portfolio companies toward programs for both team and individual coaching and development.
If founders want it, partners at Evolution can be brought in early—as early as while closing the investment—to kick-off discovery sessions with them. We will share all of the information about ourselves—good and bad—that will help the founders understand what it will be like to work with us as well.
Our goal is to understand the behaviors, personalities and opportunities for leadership development that will propel our companies. In collaboration with the founders, bespoke programs can be created to enhance their chances of success, both as a human and as a rising entrepreneur and leader.
Our agreement with Evolution is meant to support all levels of career development for founders, including individual founder coaching and management training, co-founder alignment (research suggests that 65% of startups that fail do so because of co-founder conflict!), coaching groups and organizational design. And because this is also about fostering the growth of our founders as people, these programs will also support emotional IQ development, mental health and stress management.
By baking this mindset of continuous development and introspection into our investment process from the beginning, and not simply as a reaction or a one-off, we can help develop founders—and companies—from Day 1. It also helps us be the best, most accountable partners we can be. We have always started from trust and transparency, and now, we’re putting our money there too. We can tackle the future more aligned and connected with our entrepreneurs as we take this journey together.
The Future: this is about growth
We are proud to announce this program, but we are not the first and hope not to be the last. We want to honor the trailblazers in the Bay Area—Felicis and Alpha Bridge—who have made valuable pledges to the companies and humans under their wings. We also applaud Freestyle’s recent announcement and their more structured offering for Freestyle founders. Our hope is that this trend continues to pick up momentum and that other firms in Los Angeles and beyond join in.
For me, this is also about the growth of the greater tech community here in Southern California and beyond. Starting with LA, I want to foster dialogue on the importance of founder wellness. My hope is that in the future, mental health and founder well-being are interwoven into the fabric of the venture capital landscape and VCs also consider the human side of startups. We believe it will drive the returns we seek.
Crosscut is committed to creating space for vulnerability and a true human partnership as we work with our entrepreneurs. We hope the rest of our industry will follow suit and we’d be happy to help.
Please say hello if you’re interested in learning more: brian@crosscut.vc.
Sources:
Michael Gorman and William A. Sahlman, “What do venture capitalists do?,” Journal of Business Venturing, 4:4 (July 1989), pp. 231–248.)
