The Catholic Entrepreneur's Guide to Prayer w/ Alessandro DiSanto (Hallow)
The written guide from our discussion with Alessandro on the Podcast
In the first episode of Catholic Founders, we explore the most critical question we must answer as Catholic entrepreneurs: What should the prayer life of a Catholic entrepreneur look like?
This is effectively the blog version of the discussion we had with Alessandro DiSanto, Co-Founder of Hallow. If you'd like to listen, check out the podcast.
#1 An Entrepreneur's Guide to Prayer w/ Hallow Co-Founder, Alessandro DiSanto
Entrepreneurs are fundamentally people of action. Catholics fundamentally believe that God has a specific calling. So what do we get when we put these things together?
Hallow is the world’s #1 prayer app. With over 60 million downloads, Hallow has helped countless people grow closer to God—and it’s no surprise that their own prayer journeys are what led them to answer God’s call to found Hallow.
If you're looking for a 'business owner’s prayer manual' to go alongside your operations manual, this is a comprehensive breakdown for you.
We'll start by asking, how do you know if you’re called to entrepreneurship?
Then we'll understand the pillars of a strong prayer life.
Followed by four powerful tools in the prayer toolbox.
Then, the examples of how Hallow prays, daily, weekly, yearly, in times of struggle, and in times of success.
Finally, we discuss knowing when to quit.
1. Discerning Your Call
God gives us talents and skills, not just for ourselves, but to participate in His work on earth. Alessandro stressed that the only way to truly understand how to use those gifts is through prayer.
From the beginning of your entrepreneurial journey, throughout the ups and downs, and even at the end, prayer must guide you. Without it, we risk walking in pride or wandering aimlessly.
Alessandro and his co-founders didn’t start out as experts in prayer. Instead, they recognized the need to go deeper, and that desire led them to discover their mission—creating Hallow.
Notice the key words here “they recognized the need to go deeper.” God is calling each of us to go deeper. In that depth we can find Him — and in turn, find our calling.
2. Three Pillars of a Strong Prayer Life
Alessandro shared three foundational practices that every Catholic entrepreneur should prioritize:
Silence
Alessandro pointed to 1 Kings 19, where Elijah finds God in a “still small voice”—not in the fire, earthquake, or wind. Silence allows us to hear God amidst the noise of life.
Creating silence takes effort. Alessandro likened it to climbing a mountain: it requires active pursuit.
Practical tip: Choose a time of day that works for you. For Alessandro, that’s early morning.
Confession
Alessandro noticed his prayer life weakens when he’s overdue for confession. Frequent confession reconnects us to God and keeps us spiritually healthy.
Suggested frequency: bi-weekly (or even more often, depending on your needs).
Fasting
Fasting strengthens your will and helps overcome sin. Alessandro shared how fasting helped him conquer a persistent vice, inspired by the Gospel’s teaching that some challenges require both prayer and fasting.
Tip: Start small, such as abstaining from meat on Fridays, and build from there.
3. Four Tools for Deepening Prayer
In addition to the foundational practices, Alessandro highlighted four specific tools that can enhance your prayer life:
Lectio Divina
This meditative prayer focuses on scripture. You read a passage, reflect on a word or phrase that stands out, and ask what God is revealing to you.
Fun fact: Hallow itself was inspired by a Lectio Divina session where Alessandro’s co-founder Alex Jones meditated on the word “Hallow” from the Lord’s Prayer.
The Examen
This reflective prayer helps you review your day, identifying moments when you felt close to or far from God.
It’s a great evening practice, but you can also use it in the morning to reflect on the previous day.
The Saints
Learn from the lives of the saints and ask for their intercession. They’re relatable, real people who overcame challenges and lived holy lives.
Aspirations
Short, simple prayers can keep you connected to God throughout the day. Alessandro’s favorite: “Lord Jesus, Son of the Living God, have mercy on me, a sinner.”
4. Bringing Prayer Into Your Business
At Hallow, prayer isn’t just a personal practice—it’s built into their company culture. Here’s how they do it:
Start Meetings with Prayer: Every team and board meeting begins with either silent or spoken prayer.
Optional Team Prayer Times: Weekly prayer sessions create opportunities for team members to come together in prayer.
Praying Through Decisions: Leadership prays individually about major decisions and then shares their reflections.
Company Retreats: Twice a year, the entire Hallow team gathers for retreats that include daily Mass, confession, and communal prayer. (Tune into the discussion to hear two conversion stories as well)
5. Staying Grounded Amid Success
With Hallow’s rapid growth and widespread impact, Alessandro stressed the importance of staying humble and grounded:
Focus on the Mission: The team begins meetings by reading user testimonials, keeping the focus on serving others.
Recognize God’s Hand: Alessandro acknowledged that Hallow’s success is far beyond what they could achieve on their own.
Stewardship: The team reflects on the parable of the talents (Matthew 25:14-30) as a reminder to multiply the gifts God has entrusted to them.
6. Knowing When to Let Go
As entrepreneurs, knowing when to quit can be just as important as knowing when to start. Alessandro offered two strategies:
Define Success Early: Set clear success metrics before starting a project to avoid emotional attachment. This applies well to a product feature or even the company as a whole. If you have defined success early on, you’ll know what sticking it out looks like.
Stay Rooted in Values: Hallow’s core value is love, defined as willing the good of the other. This principle guides tough decisions, like pivoting strategies or letting go of team members.
Final Thoughts
Being a Catholic entrepreneur starts with committing to a deeper relationship with God. That means prioritizing silence, frequent confession, and fasting, while also using tools like Lectio Divina, the Examen, the saints, and aspirations.
Hallow’s story shows how powerful prayer can be when it’s woven into your life and work. As Alessandro reminded us, “To whom much is given, much is expected” (Luke 12:48).
If you’re looking to grow in your faith and prayer life, download the Hallow app. It’s been a game-changer for me, and I’m confident it can help you, too.
Until next time, God bless and happy building! - Silas Mähner
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