Get Naked First
Build meaningful relationships. Fast.
You’ve been in this story a thousand times.
You meet someone new — at a wedding, a dinner, a random backyard barbecue.
Smiles, handshakes.
And within seconds, the question drops:
"So, what do you do?"
It’s harmless enough. It's the default.
But if we’re honest, it’s also a little... lazy.
Because behind every business card title — lawyer, founder, architect, marketing manager — there’s a full human being:
Dreams. Struggles. Things they love. Things they're afraid of.
And if all we ask about is work, we miss the real story.
From Hustling to Connecting
I didn’t always see it this way.
Early in my career, when I was building my first company, I loved the "what do you do?" question.
It was an opportunity.
Maybe this person could become a client. Maybe they knew someone who could open a door.
Surface-level conversations were just part of the hustle. And I was fine with that.
But somewhere along the way, things shifted.
I realized the best connections I had — the ones that led to real friendships, partnerships, adventures — didn't start with a job title.
They started with curiosity. Vulnerability. A little bit of realness.
The Broken Record Player
After I sold my business, I noticed something strange.
Whenever someone asked what I did, I would instinctively say,
"I sold my company last year."
At first, it felt like a victory lap.
But after a while... it started to feel hollow. And repetitive.
How long could that be my story?
How long could I introduce myself by something I used to do?
It made me realize: the stories we tell about ourselves matter.
And they should grow as we grow.
Why We Stay at Level 1
There’s a reason small talk is the default: it's safe.
It doesn’t risk vulnerability.
It doesn’t require much thought.
It gives us a quick, polite way to engage without committing too much.
But it also keeps us stuck at Level 1 — the surface.
You know the feeling:
Name, handshake, job title.
Maybe a quick comment about the weather or traffic.
Then we both move on, a little emptier than before.
The truth is, every relationship has levels — and you only get to the good stuff when you're willing to unlock them.
Unlocking the Real Conversation
Every time you meet someone new, you start at Level 0: strangers.
Level 1 is easy:
“What do you do?”
Level 2 might be:
“How’s your family?”
Level 3 could be:
“What’s something you’re working on that you’re really proud of?”
Level 4 is:
“What’s been on your mind lately?”
The faster you’re willing to move up the levels — by being open, curious, and real — the better the conversations get.
And not every conversation will get to Level 7. That’s okay.
But you'd be amazed how many can — if someone is brave enough to lead.
Get Naked First
If you want deeper conversations, you have to get naked first.
You create a safe space by sharing a little more than you have to.
Something real. Something human. Something that invites the other person to do the same.
You’ll notice it when it happens:
Their body language relaxes.
They smile differently.
They stop looking around the room for someone else to talk to.
It’s like you both exhale.
And suddenly, you’re not strangers anymore.
You’re humans, connecting.
Better Questions to Ask
If you want to move beyond small talk, here are a few questions that can help:
What’s something you’re really into these days?
What’s the best thing that happened to you this week?
If you weren’t doing [your job], what would you be doing?
What’s a project or hobby you’re excited about right now?
What’s something you’re learning about yourself lately?
They’re simple, friendly, and invite people to share, not just report.
And if the conversation stalls?
Share something of your own first.
Realness is contagious.
Redefining Wealth
I’ve come to believe that wealth isn’t just money.
It’s the people you know, the quality of those relationships, and the depth of trust you can build.
Every real conversation is a small investment in that wealth.
And it pays dividends for the rest of your life.
So... What Do You Do?
If you meet me at a party these days and ask what I do, here’s what you’ll hear:
"I’m a dad — I have two kids, and taking them to school every morning is one of my greatest joys.
I’m also an exited entrepreneur.
These days, I invest in businesses I believe in and coach leadership teams to perform at the highest levels.
I’m passionate about one thing above almost everything else: accountability.
For me, that means turning what we say into what we do.
And I love to help others achieve their wildest dreams through active accountability."
It’s not perfect.
It’s not polished.
But it’s the truth, and it’s my naked self.
Final Tips to Unlock Better Conversations
Be willing to go first.
Share something real — it signals safety.Ask better questions.
Questions that invite a story, not just a title.Look for energy, not just answers.
Notice what lights people up — follow that thread.Be curious, not transactional.
Don’t chase opportunity — chase understanding.Practice.
Like anything else, the more you practice, the better you get at unlocking realness.
You never know who you're meeting.
You never know what door might open.
You never know what story is waiting, just beneath the surface.
All you have to do is get naked first.
