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I don't know about you, but even though I use AI almost every single day, there is still a part of me that gets nervous about it.
I love nothing more than sitting across from a friend with a cup of coffee, driving in the car with my kids and husband to Seattle to see a World Cup Game (yep, I went), or being out in nature with nothing but my own thoughts, no machine, no screen, just me. I am deeply passionate about human connection. So passionate that I did a TED talk on The Power of Human Connection.
So when I think about what AI might mean for how we relate to each other, it concerns me. And yet here I am, using AI daily, and if I am honest, loving it. That conflict lives inside of me, and it is exactly what led me to this conversation with today's guest, Jack Swift.
I met Jack about two years ago. I was up in the hills outside of Los Angeles, spending the day at a conference on human performance, and at dinner that night I ended up sitting next to Jack.
Within minutes we were talking about Jungian psychology, Internal Family Systems, and the nature of the soul.
That is just who Jack is.
He goes deep fast, and with such warmth that you don’t realize how far you have gone until you come up for air. Something about him immediately put me at ease about what it means to be human in this moment.
Jack grew up in Hope, Arkansas (yes, the same town as the Clintons), where something was planted in him early around service and possibility. That thread carried him to West Point as a DI athlete, to the Army as an Airborne Ranger, into institutional finance, and eventually to co-found and lead TIFIN. On this AI-native fintech platform, he grew the team from 30 to over 300 people and oversaw JPMorgan's acquisition of 55ip. When Jack talks about AI, he is not theorizing. He has lived it from the inside.
And yet what strikes me most about Jack is not his resume. It is that alongside all of that, he co-founded Sangha, a community I am lucky enough to be part of. A collective of heart-centered leaders, small circles of people who meet regularly, grow together, and integrate their inner work into every part of life. It tells you everything you need to know about who Jack really is.
What makes his story so human is that through his success, he was also quietly struggling. Leaning on alcohol to numb emotions he didn’t have words for, stuck in fight-or-flight, measuring his worth by what the world reflected back to him. He shares all of this openly, including the one moment with his daughter that finally changed everything. That part of our conversation stopped me in my tracks.
Here is a taste of what we get into:
✨Leading from the inside out and why knowing your own truth is the most important leadership skill right now
✨The “resentment trap” and what a story about music in a car taught me about relationships
✨Why “I don’t know” and “I made a mistake” are the two most powerful things a leader can say
✨How Jack uses AI agents as thought partners, including helping his own son figure out his next career chapter
If you have ever worried about jobs, wondered what to tell your kids to study, or felt like this technology is moving faster than you can keep up with, this episode is for you. Jack does not dismiss that fear. He meets it with honesty and reframes it in a way that gave me hope.
As someone who carries caution around what AI means for human connection, I can tell you this conversation with Jack left me feeling more hopeful about AI, about people, and about life itself.
xo
Molly
Jack’s Resources and Links
- Level 7 Leadership: The Blueprint for the Human+Machine Era by Jack Swift, and L7 AI agent at l7leadership.com
- Website
- Sangha
Love,
Molly
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