My 2024 Reflections
Building Community, Thinking in Bets, and Knowing When to Quit
Hi friends,
As 2024 comes to a close, I wanted to share a recap of my year with some reflections and learnings. Here’s a look at the events and themes that were most present for me in 2024.
Kicked off the year with our honeymoon in Japan and Vietnam.
Simultaneously read two insightful books on hospitality:
Setting the Table: The Transforming Power of Hospitality in Business
Unreasonable Hospitality: The Remarkable Power of Giving People More Than They Expect
These books helped me reflect on how creating a sense of care, intentionality, and delight translates well beyond restaurants and into product design, team management, company building, and even personal relationships.
Made the difficult decision to wind down my first startup, Curio.
Reflecting on this chapter, I’m proud of the impact we made on our patients and grateful for the lessons in resilience, leadership, and company building that will guide me moving forward (read my LinkedIn post here).
A particularly relevant read during this time was Quit: The Power of Knowing When to Walk Away by Annie Duke. This book reinforced that strategic quitting is not failure but a valuable skill, emphasizing concepts like thinking in bets, avoiding the sunk cost fallacy, and establishing clear kill criteria to make better decisions.
Deepened my involvement in two founder communities: one focused on mindfulness/spirituality and another on poker.
Learned (more seriously) how to play poker, which became both an enjoyable hobby and a surprising teacher of valuable life skills including the game theory of decision-making, how to think in bets, and emotional regulation.
Playing simulated hands with ChatGPT/Claude and reading Every Hand Revealed by Gus Hansen were invaluable early resources. Happy to share my poker resources with anyone interested!
Traveled to the Philippines, Singapore, and India for a month.
Attended friends’ weddings, explored vibrant cities, went ring-shopping in the back alleyways of Manila, played poker at the largest casino in the Philippines, went on a solo wellness retreat in the jungle for a week.
Accompanied the trip with reading The Singapore Story: Memoirs of Lee Kuan Yew, which offers a captivating account of Singapore’s transformation into a global financial hub through visionary leadership and strategic policymaking.
Helped my talented wife launch her interior design side hustle in the Bay Area.
(And carried countless packages for her)
Made a habit of long Sunday morning bike rides with two close friends.
Over the course of the year, we rode more than 1,000 miles. These rides became a cherished ritual for catching up on life, work, and news/trends while staying active.
Completed my first century ride (100 miles).
Joined Spring Health after a serendipitous meeting through poker.
After a series of less-than-exciting interviews for tech roles, I met a mental health founder while playing poker and decided to join him at Spring Health, a leader in mental health EAP programs for employees. Together, we’re now heads-down building a new initiative, leveraging one of the largest networks of therapists in the country.
We’re quickly growing and hiring exceptional engineers, engineering managers, product designers, and product managers!
Traveled to Italy for my cousin’s wedding and spent quality time with family.
Spent time investing in and working with early-stage startups.
I deeply enjoyed connecting with other mission-driven founders working on solving problems in health, wellness, wearables, and mental health.
Celebrated our first wedding anniversary.
Stepped up my health and wellness routine:
Took 60 Barry’s Bootcamp classes, including one in Singapore.
Introduced Blueprint’s longevity mix and cocoa powder in the morning.
Used the new Lingo CGM for two months (now more affordable and available over the counter).
Installed a reverse osmosis water purification system at home (reach out if you'd like to try one of my water-tasting flights!).
Started reducing the use of plastics in our day-to-day, specifically as it relates to the consumption of microplastics in both what we eat/drink (water bottles, takeout containers, cutting boards, etc.) and wear.
Adopted a new men’s skincare routine.
Spent an uninterrupted 1-hour session with ChatGPT Advanced Voice.
Best product of the year—used it while riding my bike indoors on Zwift.
Became an American citizen 🇺🇸
I’m deeply grateful for the opportunities this country has offered me.
Reflecting on these moments, the overall theme for me this year was the power of community. Whether through poker, mental health, or cycling, being part of communities has provided not only support but also unexpected opportunities for growth and connection. Joining these groups has been a reminder of the importance of shared experiences and the transformative power of collective support.
Questions for You
What are your personal reflections for 2024?
Did any of this resonate with you?
How did you find or build community in 2024?
Let me know—I’d love to hear from you.
Cheers to a great 2025!
Matteo