In a recent episode of Lead with AI, I had the pleasure of speaking with Tom Fitzsimmons, co-founder of ByWay App, an innovative platform that's changing how people connect with spiritual guidance. Tom's journey is remarkable - from experiencing abuse within religious orders to building technology that helps people find meaning through genuine human connection. His background in tech startups, combined with his personal spiritual journey, gives him a unique perspective on how AI can bridge the gap between technology and faith.

ByWay App uses artificial intelligence not to replace human spiritual guides but to connect seekers with guides quickly and efficiently. What makes this conversation particularly relevant is how it addresses a growing need in our digital age: finding meaningful connection and spiritual insight amid information overload and increasing isolation.

From Personal Pain to Purposeful Technology

Tom's journey to creating ByWay began in an unexpected place – personal pain. He shared candidly about his experience living in a monastery in Rome, where he encountered "the very ugly side" of religious orders, including abuse. This painful chapter could have driven him away from faith entirely. Instead, years later, when a friend suggested creating a "BetterHelp for Christians," Tom initially dismissed the idea. It wasn't until he experienced a difficult breakup and found himself wanting spiritual guidance to better understand "the feminine heart" that he recognized the need for such a service.

What struck me most about Tom's story was how his past trauma became instrumental in shaping ByWay's mission. Rather than remaining a "spectator in the arena," as he put it, he chose to become a participant in creating solutions. This personal connection to the product's purpose gives ByWay authenticity that might otherwise be missing. Tom described how the nine months of market research that followed revealed a significant insight: approximately 80% of people in therapeutic sessions want to discuss their faith life, yet most therapists must wait for patients to bring up the topic.

The resulting vision for ByWay became clear – create a platform that could quickly connect people seeking spiritual guidance with directors from various traditions. Unlike therapy, which Tom values for providing "head knowledge," spiritual direction takes people "outside of themselves" to consider larger questions of purpose and meaning. This distinction forms the foundation of ByWay's approach, addressing what Tom sees as a higher calling than self-focus alone.

How AI Creates Human Connection, Not Replacement

When I asked Tom about how ByWay uses AI, his response challenged common misconceptions about technology replacing human connection. ByWay employs AI exclusively on the backend to parse information about thousands of spiritual directors and quickly match them with seekers based on their specific needs and preferences. The AI never replaces the human spiritual guide – it simply facilitates making the connection faster and more personalized.

Tom was emphatic about this distinction: "AI is never going to replace the human connection of growing in the spiritual life." He likened what they're building to how we can order food through Uber Eats or connect on dating apps – the technology doesn't replace the meal or the relationship; it simply removes friction from the initial connection. In ByWay's case, the AI analyzes information about spiritual directors' approaches and spiritualities – Benedictine, Jesuit, Franciscan, Carmelite, and others – then matches them with seekers who might resonate with their approach.

The ultimate goal is real-world impact: ByWay plans to eventually incorporate geo-tracking and fencing to encourage local, in-person meetings between seekers and spiritual guides. Tom envisions people moving from virtual connections to physical community, which he sees essential for genuine spiritual growth. As he explained, "We're not meant to replace human interaction... the bigger thing here is using a product to prompt connection." This approach addresses what Tom described as the paradox of modern life – we're more digitally connected than ever, yet increasingly lonely. ByWay aims to reverse this trend by using technology as a bridge to real community rather than a substitute for it.

Inclusion Across Faith Traditions

One of the most fascinating aspects of our conversation was Tom's vision for inclusivity. Despite ByWay's roots in Christian Catholic tradition, he emphasized that the platform welcomes people from all faith backgrounds – or none at all. When I asked if atheists or Buddhists could also find help through ByWay, Tom immediately challenged the notion of "door slamming" based on different beliefs.

Instead, he described ByWay as a connection point for anyone with questions, regardless of their faith background. He offered an intriguing comparison: "You can meet up with somebody using a dating app like Hinge or Tinder in a couple of seconds. Why can't you do that with a faith life?" This approach reframes spiritual exploration as something accessible and immediate rather than intimidating or exclusive. The goal is to start conversations and see where they lead, not to impose specific beliefs.

This open approach extends to how ByWay uses AI. Tom shared that they've considered training AI on the writings of saints and spiritual leaders, not to replace human guides but to offer additional resources between sessions with human directors. However, he emphasized that such technology would always supplement rather than replace human connection. This balance between leveraging cutting-edge technology while maintaining focus on human relationships distinguishes ByWay from platforms that might prioritize efficiency over authenticity.

The Future of Faith in a Digital World

When I asked Tom about his wildest vision for ByWay's future, his response was refreshingly modest and focused on impact rather than scale. Rather than aiming for a "multi-multi-million dollar exit," he shared that success would mean "serving a thousand people on their journey to get to know Jesus more deeply" within the first year, and perhaps 10,000 people within five years.

Tom's vision for ByWay's impact includes several key elements:

1. Community Building - Bringing people back to in-person community, whether in churches, small groups, or other settings
2. Vocational Discovery - Helping people find their calling or vocation
3. Healing Spaces - Creating opportunities for people to share brokenness in safe environments
4. Faith Formation - Supporting growth in spiritual life from a young age to prevent difficulties later
5. Hope Cultivation - Accompanying people and building hope through technology

What makes this vision stand out is its focus on using technology as a means to an end rather than an end in itself. Tom referenced the parable of the mustard seed, suggesting that starting small but with genuine faith can lead to significant impact. He believes that building technology to facilitate human connection around spiritual matters can help address fundamental questions that many people don't begin asking until later in life "as the complexity builds."

The most poignant moment in our discussion of the future came when Tom shared a personal story about his aunt and grandfather's deaths. With his aunt, he managed to arrange for last rites before she died, but his grandfather explicitly refused similar spiritual attention. Tom worried deeply about his grandfather's spiritual state until a spiritual director helped him recognize that faith means trusting outcomes we cannot control. This story illustrated Tom's view that ByWay isn't about controlling spiritual outcomes but about creating opportunities for connection and guidance, with faith in what might follow.

Building Bridges Between Technology and Spirituality

As our conversation drew to a close, I was struck by how ByWay represents a new paradigm in both technology and spirituality. In a world where we can have food delivered in an hour or meet someone on a dating app within a day, ByWay offers similar convenience for spiritual connections without promising instant spiritual growth. The platform recognizes that spiritual development takes time but removes unnecessary barriers to getting started.

What makes ByWay particularly relevant is how it addresses the paradox Tom identified in our modern world. Despite unprecedented digital connectivity, loneliness continues to rise. By using AI to facilitate meaningful human connections rather than replace them, ByWay offers a model for how technology might enhance rather than diminish our humanity. When Tom described the church as "a hospital for broken people," I could see how ByWay embodies this understanding – using technology to create an open door rather than a barrier.

For those of us interested in the future of both technology and faith, ByWay offers an inspiring case study. It suggests that AI can serve spiritual development not by attempting to replicate human guidance but by connecting people more efficiently with the guides they need. As Tom put it, "AI is never going to know your spirituality... What we want to do is just connect people quickly to another human being that can accompany them or guide them." This humble approach to technology's role in spiritual matters may well point the way forward for other applications seeking to enhance rather than replace human connection.

Join the Journey

If Tom's vision for ByWay resonates with you, I encourage you to keep an eye on this emerging platform. As we navigate an increasingly digital world, finding ways to use technology that enhance rather than replace human connection becomes ever more important. ByWay App is set to deploy in just a few months, offering a new model for how AI can serve our deeper human needs.

For listeners of Lead with AI, this conversation with Tom Fitzsimmons offers an insightful counterpoint to fears that technology will isolate us further. Instead, it suggests that with the right intention and design, AI can help us find our way back to one another and perhaps even to deeper spiritual understanding. If you're curious about faith questions or fascinated by technology that enhances human connection, I invite you to follow ByWay's development. Their approach offers valuable insights that could apply to many areas of digital innovation.

The question isn't whether technology will continue to transform our lives, but how we'll direct that transformation toward what matters most – genuine human connection and meaning. As Tom reminded us, sometimes the most valuable innovation starts small, like a mustard seed, but can grow to transform landscapes both digital and spiritual.

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