Learning how to ask for this changed my life

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Imagine walking into a Chipotle in LA. You step up, scan the menu, and order a burrito, bowl, or maybe a salad. You go down the line, grab your food, and that’s that.

Simple. Familiar. Fine.

But what if a Michelin-starred chef was in the back—just waiting to cook you something with ingredients flown in from everything in the world?

Would you ask them to make you something?

Maybe. Maybe not.

But what if you found out it was free—all you had to do was ask?

Suddenly, yeah. You probably would.

Okay, maybe this is a terrible analogy, but here’s the point: we leave things on the table all the time. Not asking is basically choosing the burrito when there’s a world-class meal in the back. We don’t know what we don’t know.

Years ago, I needed to withdraw thousands of dollars. My bank had no physical branch, and Chase turned me away. Frustrated, I called my bank to complain. They got Chase to approve it.

Most people would stop there. But I was like, “can you do something for my embarrassment and trouble?”. A little time went by and the representative said they could give me $100 for my trouble.

Most everyone would accept it right then and there. But I’m a menace and said, “can you make it $250?”. They paused for a few seconds and said, “yes, you’ll see that amount in your checking account by tomorrow morning”.

And the next day, it showed up in my account.

That moment taught me something: audacity gets you places. It’s not about entitlement, it’s about asking with intention, curiosity, and a little courage. You’ll get some no’s. But sometimes, you’ll get $250. Or a chef’s special. Or a brand deal. Or a breakthrough.

Asking has opened doors for me: deals, sponsorships, venues, connections. You’d be surprised what people will say yes to when you just ask. And I just kinda forget the nos.

Asking can feel risky. It takes emotional intelligence. You don’t ask a new friend for $1,000 (unless you’re wild). But learning how to read the room while still making bold ask is a superpower.

This isn’t just for entrepreneurs. It works whether you’re asking for a discount, a job referral, or help with something that matters.

So—try it. Ask for something that feels audacious this week. Or don’t. Just know: you often have nothing to lose by trying.

What’s something you think would be audacious yet scary to ask for? Let me know and I’ll reply with my thoughts - I’ll read every response.

If you’re newer here, LA in Common is a community of the best people you know in LA. Hopefully this newsletter gives you a glimpse of what we’re building. If you’re looking to plug into a community of highly motivated yet absolutely genuine people - this is it. Reply ‘interested’ and I’ll send you more info.

Glad you’re here,
Daniel