“Work is love made visible.”
-Khalil Gibran
I am fascinated by life.
You and I have this one chance to live, and to live beautifully.
How will we reflect on our lives, as we come to the end?
I hold that we will find life meaningful and good to the degree we have both loved others well and have transformed into the fullness of what we can be - following the path of what Carl Jung calls individuation.
Our work can align to this end. It can be a meaningful pursuit of goodness for self and others, and a way that furthers our own transformation.
For my own work, I delight in deep complexity, in insights and strategy, in the cultivation of wisdom, in the development of others, and in work as a creative act.
Whether this is in a startup or a mature organization, whether this is in technology or the inner journey, or whether this is at scale or with an individual… for me, it’s all part of the journey.
Projects
Vervaeke Foundation
&
Scaling Anagoge
I founded Mainstay in 2004. Our mission of “We give more than we get” reflects our entire team’s commitment to business as a pursuit of the Good. We believe money is important, but that it must serve people. Who we are, and the lives we live - that is what truly matters. When Mainstay reached ~100 team members in 2024 and hit 20% of our goal to become a 100-year company, I moved from CEO to the Chair position and continue to be involved with governance and strategy. www.mstech.com
In 2023, I cofounded (alongside CTO Aaron Bassett) an future-looking AI focused startup. We focus on three things:
1: predicting the future of the MSP industry and the IT department.
2: training and equipping leaders for that future.
3: building tools and products that unlock the power of AI power, while providing us data and feedback for our mental model of the future. www.orchestrateailabs.com
While I care about business, it’s only one way to serve people. My deep, abiding passion is to walk with others on the inner journey. My own life has been transformed by the kind presence of skilled wisdom guides, and it brings me great joy to walk with others. Socratic Counseling is both a professional practice offered to clients and a distinct approach (founded by myself, Christopher Mastropietro, and Rick Repetti, under the scientific oversight of John Vervaeke), rooted in both living philosophy and cutting-edge psychology. As a Socratic Counselor, I meet with clients to explore both their inner and outer worlds and find movement, towards a more beautiful, meaningful life. www.socraticcounseling.com
Dr. John Vervaeke is one of the world’s leading cognitive scientists, and arguably the most accomplished wisdom researcher. His work has had a titanic impact on my life, and in 2022 I first came alongside him to build two nonprofits - Vervaeke Foundation and Scaling Anagoge - as organizations to support the development of wisdom practices, the promotion of teaching, and the furthering of the science of spirituality. I remain Chair of both nonprofits. www.vervaekefoundation.org and www.johnvervaeke.com
I am husband to Trish, father to Chloe, Noah, and Olivia.
I live in both central New Hampshire and Charlotte, North Carolina.
The most effective way to work with me is through one of the projects outlined above. I conduct all leadership development and mentoring through Socratic Counseling.
I also provide keynotes on understanding and leveraging AI, on aligning businesses to human flourishing, and to the pursuit of wisdom through vocation. For speaking, and for strategy consulting, please reach out directly.
