Why Saying ‘Yes’ Could Either Skyrocket Your Empire or Burn It to the Ground — The Untold Truth Every Entrepreneur Must Hear Now

I didn’t scale my career by saying no. Not in real estate. Not in venture capital. Not in life.

Sometimes the best thing you can do is say yes.
Even if it’s messy.
Even if it’s unclear.
Even if it’s outside your comfort zone.

That’s how I’ve always operated, and I’m still just getting started.

Related: 10 Habits That Separate Rich and Successful Founders From Wannabe Entrepreneurs

I’ve said yes to things that made zero sense on paper

You know what some of the best opportunities look like at first?

Work. Chaos. A gamble.

I didn’t build one of the largest independently owned brokerages in Texas by playing it safe. I built it by saying yes when it felt too early, too weird, too unknown.

There wasn’t a perfect roadmap.
There was just instinct.
And a whole lot of hustle.

People want the full itinerary before they take the first step.
What does hill #3 look like? Where are the bathrooms? When’s lunch?

Clarity doesn’t come from standing still. It comes from moving forward.

You can’t outsource gut instinct

Every pitch deck looks polished. Every founder sounds passionate. Every opportunity feels shiny in the moment. So, how do I decide what to say yes to?

I bet on people.

Of course, I look at the numbers. The market. The risk. But if someone’s got heart, grit, vision, and values, then it’s usually a good sign.

I’ve backed first-time founders.
I’ve backed celebrities.
I’ve backed people with zero connections but massive drive.

It’s not about whether it’s their first swing or their hundredth.
It’s about whether they’re stepping up with the bat superglued to their hands.

We don’t love Babe Ruth because he never struck out.
We love him because he kept swinging.

Related: How Saying ‘Yes’ to Every Opportunity Helped My Startup Make $1 Million in the First Year

Most people are scared to say yes

Saying yes means taking a risk. It means committing to something you might fail at — even publicly. It means opening the door to something new… that might not work.

But here’s what I’ve learned after two decades in business:

The bigger risk is waiting. Waiting for the perfect timing. Waiting for a guaranteed return. Waiting until you’re “ready.”

That’s not a strategy. That’s fear.

You can’t microwave real growth.
You’ve got to be in the kitchen.
Rolling dough. Dropping it. Cleaning up the mess. Starting again.

Saying yes builds the muscle you need later

Here’s something I’ve noticed across the board:

Most successful people were yes-men and yes-women at their first jobs.

Worked the floor? Yes.
Answered the phones? Yes.
Stayed late? Every day.

It’s not about being a pushover.
It’s about showing up with no ego. No entitlement.

That kind of posture doesn’t just open doors.
It builds the muscle memory to succeed when it’s your name on the door.

Read More: How Saying ‘Yes’ to Everything Can Stall Your Growth

Saying yes doesn’t mean saying yes to everything

Let me be clear. Saying yes with purpose doesn’t mean saying yes to distractions. It means asking better questions before you commit.

Ask yourself:

1. Can I grow from this?
2. Can I help someone else grow?
3. Does this align with the life I’m building?

If it’s a yes, move. Data is helpful, but instinct is your edge.

People who say yes build better networks

This one gets overlooked. You don’t build a killer network by waiting around.

You build it by saying yes to the 8 a.m. coffee. Yes to the LinkedIn intro. Yes to the event you weren’t sure about — but showed up anyway.

Curiosity is underrated.

You’re allowed to say yes just because you want to learn something. You’re allowed to say yes just to connect with someone. Some of my best investments start with a coffee and no agenda.

I live for that.

That’s why I started Coffee with Closers and Lunch with Legends.
To squeeze the juice out of every yes.

Make it count.
Turn the moment into momentum.

Join top CEOs, founders and operators at the Level Up conference to unlock strategies for scaling your business, boosting revenue and building sustainable success.

The world opens up to people who say yes

Every room I’ve stepped into came from saying yes to the last one.
Every leap I’ve taken opened doors I couldn’t see until I jumped.

Saying yes is about believing something better is possible — even if it’s not guaranteed.

Even if nobody else gets it.
Even if it scares you.

I’d still be sitting on the sidelines if I waited for the perfect moment.

Instead, I’m in the game.
Building. Betting. Believing.

You don’t need every answer.
You need the guts to say yes to the next right thing.

Say yes before you’re ready.
Say yes when it scares you.
Say yes when your gut says go, even if the world says wait.

Especially if you’re young, say yes to opportunities and build your own.

That’s where growth starts. That’s where momentum lives.

We don’t love Babe Ruth because of his perfect record.
We love him because he showed up. Swung hard. Kept swinging.

Be more like Babe.
Change the game by saying yes and stepping up to the plate.

You might see a return on your “yes” investment.