On this episode of Paper Napkin Wisdom, I sat down with Juan DeAngulo, a veteran investor, entrepreneur, and systems thinker whose work bridges discipline and heart. Juan has scaled billion-dollar investment platforms, co-founded Inselligence—a fast-growing tech startup—and, just as importantly, learned to balance leadership with wellness after battling through years of personal struggle.

But his napkin is deceptively simple:

“I am true to myself and I release the outcome.”

Written on December 21, 2023, this phrase captures the essence of a leader who has lived both the cost and the gift of authenticity.

The Power of Truth to Self

Juan shares in the conversation that too often, leaders bend themselves to fit expectations—investors, clients, even their own self-imposed standards. The napkin reminds us that real clarity starts with aligning choices to who we are, not who we think others want us to be.

When you’re true to yourself, decisions become less about approval and more about alignment. As Juan puts it, that’s where courage begins: being willing to stand in your own truth, even if the path is uncertain.

Releasing the Outcome

The second part of Juan’s wisdom is just as critical. Once you’ve acted from a place of authenticity, you can’t cling to the result. He describes how early in his career he suffered from crippling anxiety and panic attacks—driven by an obsession with outcomes. Only when he learned to let go of the uncontrollable did he begin to reclaim peace and resilience.

“Release the outcome” isn’t resignation. It’s freedom. It’s choosing to focus on process, presence, and people—knowing the results will follow.

Five Key Takeaways

1. Authenticity is the anchor. Align with who you are before you align with strategy or market.

• Take Action: Write down one decision you’re facing and ask: is this truly aligned with who I am?

2. Control the process, not the results. You can own your effort and habits, but not the scoreboard.

• Take Action: Identify one area where you’re outcome-obsessed and reframe it into process goals.

3. Anxiety comes from gripping too tightly. Juan’s story of panic attacks shows how unsustainable it is to carry everything.

• Take Action: Create a daily ritual—meditation, journaling, or exercise—that helps you let go.

4. Resilience is a practice, not a trait. It’s built by repeatedly showing up, grounded in truth, even when results are uncertain.

• Take Action: Track your “resilience reps”—moments when you acted authentically despite fear.

5. Leadership is human connection. Systems and processes matter, but they’re only powerful when built on genuine human trust.

• Take Action: This week, check in with one teammate not about performance, but about how they’re doing as a person.

Why This Matters Today

In a world obsessed with metrics, hacks, and shortcuts, Juan’s napkin cuts through the noise. Leaders everywhere are tempted to measure themselves only by outcomes. But true transformation happens when you ground yourself in authenticity and trust the process.

About Juan DeAngulo

Juan DeAngulo is the co-founder and CEO of Inselligence, a platform bringing process intelligence to sales operations across three continents. He previously co-founded a real estate investment platform managing over $4 billion in assets. A graduate of Harvard Business School’s OPM program, Juan combines investment discipline with startup agility.

Beyond his professional achievements, Juan’s journey through debilitating anxiety and recovery through meditation, wellness, and holistic growth makes his leadership deeply human. Today, he is recognized as a culture architect—helping entrepreneurs and organizations design scalable systems, healthy cultures, and authentic leadership practices.

Connect with Juan on LinkedIn.

Your Turn

Juan’s napkin challenges us all: Are you being true to yourself? And if you are, can you release the outcome?

Grab a napkin, write down your answer, and share it with the hashtag #PaperNapkinWisdom.

Because when we act from authenticity and let go of the rest, we discover freedom—and often, better results than we could have planned.