This is part 2 of our conversation with Thiago Da Costa, serial entrepreneur and founder and CEO of a Datagrid AI, a company that creates agent and connectors to help companies work more efficiently.

In part one we explored Thiago’s journey as a serial founder, and what it takes to scale companies from zero to meaningful revenue.

In this second part, we go deeper into what truly separates great CEOs from dangerous ones. We talk about transparency, capital discipline, customer obsession, and the growing risk of the celebrity CEO—leaders who master distribution and attention before they build real products. Tiago shares candid perspectives on motivation, resilience, and why founders who aren’t deeply anchored to the problem they’re solving will eventually burn out.

We also shift into a broader discussion on AI—why this moment is fundamentally different from past technology waves, where real opportunities still exist, and why so many AI startups are destined to fail.

Contact Dino at: dino@al4ep.com

Websites:

al4ep.com

datagrid.ai

Additional Guest Links:

LinkedIn: linkedin.com/in/thiagocosta2

Corporate LinkedIn: linkedin.com/company/datagrid-ai/

Authentic Leadership For Everyday People / Dino Cattaneo

Dino on LinkedIn: linkedin.com/in/dinocattaneo

Podcast Instagram – @al4edp

Podcast Twitter – @al4edp

Podcast Facebook: facebook.com/al4edp

Music

Susan Cattaneo: susancattaneo.bandcamp.com

Today's guest is Thiago Da Costa, a serial entrepreneur with multiple exits and decades of experience building deeply technical companies. His latest venture, Datagrid AI is an enterprise agentic solution that connects data and automates workflows across tools, files, and systems,

Thiago brings a rare combination of technical depth, founder instinct, and hard-earned perspective on what it really takes to start, scale, and survive as an entrepreneur. We talk candidly about the realities of founder-led growth, why most early hires fail, how scaling actually works in practice, and why instinct—tempered by experience—often matters more than advice.

We also dig into the employee side of the equation: how to evaluate a founder before joining a startup, what questions really matter in interviews, and why effort, ownership, and clarity are the ultimate differentiators in today’s market.

Contact Dino at: dino@al4ep.com

Websites:

al4ep.com

datagrid.ai

Additional Guest Links:

LinkedIn: linkedin.com/in/thiagocosta2

Corporate LinkedIn: linkedin.com/company/datagrid-ai/

Authentic Leadership For Everyday People / Dino Cattaneo

Dino on LinkedIn: linkedin.com/in/dinocattaneo

Podcast Instagram – @al4edp

Podcast Twitter – @al4edp

Podcast Facebook: facebook.com/al4edp

Music

Susan Cattaneo: susancattaneo.bandcamp.com

My guest today is an old friend, Nicolas Darveau-Garneau. We met in business school a long time ago, and he went on to become Google's chief evangelist. In that role he advised over a thousand CEOs. He condensed all that wisdom in a brand new book that's called Be A Sequoia Not A Bonsaoi. The book explains how the top 5% of companies beat their competitors.

Before becoming Google's chief evangelist, Nick also started and sold 4 companies. In this conversation, we talk about how to figure out if you want to be an entrepreneur and how to assess your own strengths to find the right path, what truly differentiates exceptional leaders, why culture is one of the most underestimated strategic assets.

Contact Dino at: dino@al4ep.com

Websites:

al4ep.com

nicolasdarveaugarneau.com

Additional Guest Links:

Be A Sequoia Not A Bonsai on Amazon - Barnes and Noble Books A Million Book Shop

LinkedIn: linkedin.com/in/nickdg

Authentic Leadership For Everyday People / Dino Cattaneo

Dino on LinkedIn: linkedin.com/in/dinocattaneo

Podcast Instagram – @al4edp

Podcast Twitter – @al4edp

Podcast Facebook: facebook.com/al4edp

Music

Susan Cattaneo: susancattaneo.bandcamp.com