Why I left everything to join a monastery, then left to start SENT
A few weeks ago at the inaugural SENT Summit, I shared my testimony for the first time of how SENT came to be. It was a powerful moment for me and the community, so I’ve decided to share it with you today.
Holy Daring
St. Teresa of Avila, one my favorite saints, was a contemplative, cloistered nun. She traveled by horse-pulled wagon across Spain founding 15 monasteries. The global order she founded, the Discalced Carmelites, continues almost 500 years later. She encouraged her spiritual daughters to have a “holy daring.”
This “holy daring” means being bold and ambitious in the best sense. It means seeking God above all else and being daring in your openness of how you can be an instrument for His mission in the world.
As Spirit-led founders and executives, we are on a bold, courageous, adventurous journey. This means first of all being driven and daring for God and holiness. And in how to serve Him and make Him known in this life. You want to be transformed through your faith and then transform the world around you through your work or venture.
My Conversion
Like most of you, I’ve always had a strong drive, but this hasn’t always been channeled in the right ways. Growing up, I wanted to achieve, to be somebody, to win, to have people recognize me, and it worked. I was able to get into some of the best schools in the world including Harvard and Oxford. I advised politicians and worked on billion-dollar deals as an investment banker.
I worked hard, but I also saw the shadow side of high-octane business culture. At Harvard Business School, we’d take weekend trips to NYC clubs or Arizona resorts just for fun. In banking, we’d work 90-hour weeks, including most of Sunday after partying hard the night before. I didn’t even have time for Mass, nor was I particularly interested at the time. While there was often lip service to ethics and idealism, at the end of the day, business was primarily a-moral, about winning, making money, and success.
In 2008, I joined a startup with a climate change mission. Although the company was visionary, growing, and doing important work, the leadership was manipulative. To have things look good and keep things appearing successful, clients, investors, and even our team were misled about what was really going on. Eventually, the company collapsed.
I asked myself: Is this what business is supposed to be?
I began to see that if I kept going on the path I was on, I would be like this – doing whatever it took to fuel the appearance of success and get what I wanted.
Around this time, at one of my lowest points, God in his mercy allowed me to have an intense and transformative encounter with Him. One day I returned from the gym and was taking a shower. At that moment, the veil pulled back, and I seemed to see within myself. I saw a cancer within me – no amount of water could wash off the pain and sin I saw within.
But God could.
I felt Him inviting me to change. It was the most powerful experience of my life.
I left the energy startup, started a consulting business, and within a few months, I started thinking: how could I give everything to this God who had given me so much and showed me so much?
The Monastery
I wanted to run to a cave or hidden monastery somewhere to pray and be with Him. I went on a retreat and spent a day praying and fasting in the middle of the woods, in nowhere West Virginia. While sitting in the woods, I buried my business card – a symbol of my professional identity – in a rock crevice by a stream. I thought I needed to leave behind my ambition and success to follow God. I left behind a thriving consulting business. I thought it was good to leave behind business because I didn’t understand how this could be compatible with this new spiritual journey.
In 2012, I entered a Carmelite monastery in California. I ended up spending the next 7.5 years living as a Carmelite friar in monasteries in the Western US and Africa. We spent 3-4 hrs a day in prayer, did ministry everywhere from the seedy tenderloin of San Francisco and Skid Row to nursing homes and Catholic schools. I did hard manual labor and cleaned a lot of toilets.
Building SENT
About 6 years into my time with the Carmelites, things shifted within me again, and I felt like God was inviting me to harness my experience and gifts in “the real world.” I dug up that business card. The Catholic faith had changed my life. I hoped that others could experience some of what I had tasted. I studied Catholic founders of movements – how they had led revitalization of the Church in the past. I found that the Saints were Holy and Entrepreneurial. They knew how to marshall resources and mobilize teams. They were often Wise in the ways of God and the world.
Mother Cabrini, the first American saint, founded 67 hospitals and orphanages on 3 continents in 25 years – every 6 months she founded a new institute. She wasn’t afraid to raise millions of dollars for the projects, but she also prayed for hours a day and surrendered any “success” to God. These capabilities are often something we miss when we think about the saints. You can be bold and radical in seeking God and also in building with Him at the core.
I discerned to not continue in the monastery, left with nothing, and worked out of my aunt’s basement. I wanted to integrate a drive to build & create with a radical pursuit of holiness. I found that there were many others who shared these longings. SENT became a community and hub for founders and leaders seeking a radical holiness and impact. Drive for change and ambition is a good thing, but it needs to be purified and refined so that God can use it.
This doesn’t just happen on its own. No one has ever built anything great alone. We need God. And we need each other. Saints never did great things alone – they had community, support, and allies. They integrated prayer and radical pursuit of virtue with their drive for impacting those around them – whether in the halls of the cloister or the broader world stage. We too need allies and partners in this challenging but all-important mission of holiness for impact.
Join SENT
Building SENT changed my life, and my greatest hope is that it changes yours too. We believe Spirit led founders will have an outsized impact on renewal of the Church and world in our lifetime. The SENT network is the nexus for Spirit-led founders and executives.
We want to empower and support bold leaders hungry to build transformative ventures and even more transformative lives.
If you’re not already involved in SENT, we’d be honored if you’d consider joining the SENT Network and giving us the opportunity to serve you, your company, and your mission. New Fellowship communities will be launching in September and the deadline to apply is August 1st. We also have rolling applications for Essential Membership and Mentorship. Learn more about our memberships.
If you’re interested, you can learn more or apply to join below.
