How Alessandro DiSanto Left Finance to Build Hallow

The Blog Version of Episode #3. A deep dive in the Alessandro's back story + The Vatican's mission to lead AI and Technology development.

Welcome back to Catholic Founders. Today we’re releasing the written version of episode #3. If you prefer to listen, you can do so here. 👇

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Why should you read / listen?

• To hear an amazing example of being willing to answer the call God had for one of His children.

• You’ll hear a realistic description of what it was like for these three to leave their high-paying jobs to start… a prayer app (imagine the ridicule in the minds of their co-workers).

• And you’ll get a sneak peak into what the Vatican conference on AI and technology last year discussed.

• Plus… BONUS! You’ll get to know Alessandro’s story in a more nuanced way.

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When Alessandro DiSanto co-founded Hallow, the leading Catholic prayer app, it wasn’t the career trajectory he had in mind. Despite being raised in a family of entrepreneurs, Alessandro had no intention of becoming an entrepreneur. He decided to pursue finance and worked in a world of high-stakes investing and billion-dollar deals. But through a deeply personal rediscovery of prayer, he found himself facing a different kind of calling—one that led him away from the private jet money and into the unknown world of Catholic tech.

From Finance to Faith: An Unlikely Path to Entrepreneurship

Growing up in an Italian Catholic family, Alessandro was surrounded by hard work—his relatives ran pizzerias and a real estate business. But he was academically inclined and set his sights on finance, following in the footsteps of his grandfather, an investing enthusiast. Private equity became his world, where long hours and high pay promised financial security and prestige. Entrepreneurship? Not on his radar.

But something was missing. Despite outward success, Alessandro found himself stressed, overworked, and physically drained. It was his best friend (and future co-founder), Alex, who first suggested meditation to help him find peace. That seemingly small suggestion set off a chain reaction that led Alessandro to rediscover prayer in a profound way.

Discovering Prayer as a Foundational Practice

As Alessandro explored meditation, he found himself confronted by deeper, uncomfortable questions. What was he really meant to do with his life? Had he ever truly sought God’s will? These weren’t questions he could simply ignore—and for the first time, he took them seriously.

It was through Lectio Divina and the Examen—forms of structured, meditative Catholic prayer—that Alessandro experienced a profound shift. No longer was his faith simply an intellectual exercise; it became a real, living relationship with God. And with that, a calling began to emerge.

A Moment of Clarity: The Day They Committed to Hallow

One of the most pivotal moments in the journey toward founding Hallow came during a Saturday morning gathering with his co-founders. Alessandro had been working relentless hours in private equity, pushing himself to exhaustion. The night before, he had stayed in the office until 5 a.m., only getting about an hour and a half of sleep before Ubering to his friend Eric’s apartment in the burbs.

As they sat together, they decided to begin with 45 minutes of contemplative prayer—