Unreasonable Is the Advantage

In 2006, Will Guidara became the general manager of Eleven Madison Park, a fine dining restaurant in New York City that was... fine.

It had a Michelin star, elegant décor, and a respected chef, but it wasn’t transformative. The restaurant industry's playbook was clear: maintain standards, execute flawlessly, and play it safe.

Guidara and Chef Daniel Humm chose a different path. They wanted to serve excellent food, but they also wanted to create experiences so memorable that guests would tell the story for years.

They called it "unreasonable hospitality."

The Philosophy

Most restaurants focus on consistency: the same dish, prepared the same way, every time.

Guidara asked a different question: What if we listened so carefully that we could give guests something they didn't even know they wanted?

Businesspeople wanting to try a classic New York hot dog? Send a server out mid-meal to get one from a cart.

Family missing a beach vacation? Bring sand and beach chairs to their table for dessert.

This was expensive, inefficient, and impossible to scale. But Guidara understood: people don't remember perfect. They remember personal.

The Transformation

In 2017, Eleven Madison Park was named the World's Best Restaurant.

The restaurant became legendary not for what was on the plate, but for how it made people feel.

Guidara built a culture where every team member understood their job wasn't to execute tasks, but to create meaning.

In my work with LOUD Ventures and LOUD Collective, I see this choice constantly: optimize for efficiency or impact? Follow the playbook or write your own?

While systems matter, our greatest differentiator is often what we're willing to personalize and risk for the people we serve.

That's not a strategy we can copy, but a culture we have to build.

After founding four ventures and investing in over 80 companies through my work with LOUD, I've been in many battles. The pain isn't the conflict. It's being surprised by it.

Most founders brace for external battles, like competitors, market shifts, and regulatory hurdles. But the conflicts that truly test a venture happen inside the walls, between the people who all want the company to succeed.

The Founder’s Paradox

A venture is a long road with different phases and different people stepping in along the way. The scrappy founding team that got you from 0 to 1 isn't always the right team to take you from 10 to 100. 

Just because a founder started the journey does not mean the foundation is still right for the company it has become. The instincts that served you well in a garage don't always translate to managing 50 employees across three states. 

The flip side is equally true: Just because an experienced leader joins later does not mean they fully understand the history and lessons that got the company here.

The tension between founders, funders, leaders, and operators is constant. I've sat in enough board rooms and leadership meetings to know: everyone has a valid perspective. Everyone is trying to protect what they believe is right, especially as success grows.

The founding CEO wants to preserve the mission and culture. The new executive wants to implement best practices that drive efficiency. The investors want strong returns. The early team wants recognition for their sacrifices. 

All of these perspectives are legitimate. All of them will, at times, conflict.

The Path Forward

So what do you do with this? Three things:

1. Expect it. Stop being surprised when tension emerges. It's not a sign that you hired wrong or that the culture is broken, but that you're growing, that the stakes are higher, and that people care enough to fight for what they believe.
   
   

2. Stay open. The moment you stop listening - really listening - to perspectives that challenge your own, you've chosen stagnation over evolution. The best outcomes I've seen come when founders, funders, and leaders create space for honest, sometimes uncomfortable dialogue.
   
   

3. Honor the past, but do not be afraid to evolve. Your origin story matters. The lessons learned in the early days are real. But reverence for the past can't become a prison. The company you are today needs to be built for the company you're becoming tomorrow.

Having been on all sides - as a founder, investor, advisor, operator - I can tell you that the battles are worth it. 

The conflict is part of the journey. The only question is whether you'll let it break you or sharpen you. Need any help? Our team at the LOUD Collective can help.

I don’t want fear to be the reason I play small.

I've seen brilliant people shrink from their potential because they let fear make their decisions. Fear of failure, of judgment, or of outgrowing who they used to be.

I've done it myself more times than I'd like to admit.

This year, I'm choosing differently. I want to live into my greatest potential and do what feels right for myself and the world I care about. 

That's why I've chosen this mantra for the year ahead.

Marcus Aurelius said it long ago, but it's resonating with me more deeply right now.

They remind me daily that the external chaos will always be there. The only variable we control is how we show up.

So this year, when fear whispers "play small," I'll return to this truth: I have power over my mind.

If you have a mantra for this year, I'd love to hear it in the comments. If you don't have one yet, give yourself time to reflect and plan for the year ahead.

It's never too late to start playing big.