Habits matches you to vetted advisors who already work with hundreds of people like you…same income range, same life stage, same questions.

It takes a few minutes. It’s low pressure. So whether you’re a first timer or thinking of a change, this is the obvious next step.

Use their mobile app, your computer, or use their instant match solution if you’re pressed for time!

I’ve made similar posts like these before, and they always seem to resonate with a lot of people. What do you think? Are single households the latest flex?

Last week I went to visit one of our institutional investors. And it was a full circle moment.

We’ve been raising capital again, and it’s standard practice to go back to existing investors. Some have pro rata rights. Some have MFN clauses. Some just deserve the respect of a conversation before you open the round wider.

But this one felt different.

4 years ago, I pitched at one of Elevate Ventures’ pitch nights. It was hosted alongside TechPoint in Indiana. I remember the room vividly. Maybe 15 people. 10 were polite attendees making sure there was a crowd. 5 were actual angels or VCs. At the time, Habits was me, myself, and I.

And my vision? All over the place. A marketplace. A data platform. A financial advisor GTM engine. Basically HubSpot, Reddit, and Bloomberg Terminal had a baby and I was trying to explain it in 15 minutes.

I’ve always been a dream big type of guy. Sometimes painfully so.

That night I met someone who would quietly follow our journey for years. Opening our monthly investor memo as we crawled from $10k ARR to $20k to $50k. Small numbers. Small wins. Consistent progress.

In May 2024, we pitched their investment committee and secured a $100k check. Our first institutional check. That’s different. It hits different. 6 months later we closed over $1M total.

Fast forward to last week. I walked into their new office.

Colored LED lighting. Cold brew on tap. Putting green outside. Podcast studio. Massive open floor plan. Conference rooms that make you feel like you should be reporting quarterly earnings.

Meanwhile, I spend 95% of my time at a standing desk in my apartment. 2 monitors. An iPad. A notebook. Coffee I made myself. Leaving the apartment for errands, the gym, or a walk so I don’t feel like an animal in captivity.

When I stepped off the elevator, it felt like walking into a tunnel before a stadium entrance. Like you’re about to run out and people are chanting your name.

They weren’t. But that’s what it feels like.

Environment can trick you into thinking you’re bigger or smaller than you actually are.

Half their IC was on Zoom. 4 people were in person. I stood at a podium.

For 15-20 minutes, I did what founders do. Word vomit. Progress. Reminding them why they invested. Showing what we’ve built. What we’ve learned. What we’ve pivoted on. What we’re iterating on. I was bragging in the healthiest way possible.

“You gave me $100k. Here’s what I did with it.”

I felt totally natural. No nerves. No imposter syndrome. Honestly, I barely practiced. I blocked off 1 hour that morning to tighten my thoughts.

Then I finished. No clapping. No dramatic pause. Just a subtle, “Nice progress.” And straight into Q&A. It wasn’t rude. That’s just the game.

But it always makes me laugh.

3 years of working 6 days a week, 10-12 hours a day, for a subtle “nice job.” And I don’t mean that bitterly. It’s just funny. VCs hear 100 pitches and say yes to maybe 5-10. And probably seriously investigate 1. Their calibration is different. Their emotional response is muted by design.

That subtle nod is a compliment. It’s just not cinematic.

Validation at the next level rarely feels as dramatic as you imagined.

The Q&A is my favorite part.

I love getting drilled. It feels like a test. Not the boring ones I got Bs in. The kind that test conviction. The kind that test if you hesitate. If you really believe what you’re saying.

They challenged assumptions. Dug into metrics. Questioned the pivots. Not aggressively. Just professionally. Seeing if there were cracks.

There weren’t.

We wrapped up. Handshakes. Next steps. Some stayed. Some moved on to their next meeting within 30 seconds. And that’s the part that always hits me.

You walk in feeling like you’re about to run into a stadium. You leave realizing you were one 45-minute block on someone else’s calendar.

It’s the same weird feeling you get when a friend-of-a-friend casually mentions their bonus was 40% higher this year. Or that they just bought a Rolex. Or that they’re spending 10 days in Italy but “it wasn’t that bad.” Those moments where you think, why did you say that to me?

Not harmful. Not malicious. Just slightly off. And then you realize. They’re not trying to impress you. They’re just living their life. And you’re not the main character in it.

Most moments that feel significant to you are background noise to someone else.

Afterward, I walked around their office introducing myself to random employees. I genuinely forgot what it felt like to work in a room with 20+ people at once.

Say what you will about remote work and flexibility. Spend enough time in isolation and it messes with you.

Some days I’ll walk to a coffee shop and pay $6 for a cold brew just to say, “Hi. Can I get a cold brew?” Wait. “Thank you.” And walk home. Human interaction as a purchased commodity.

It’s funny how our brains work.

In this case, I was technically asking them for money. Pitching. Raising capital. But even if they had said no, the chance to be in that room, feel the energy of people building things, see other humans operating in close proximity, was worth it.

Just like the $6 coffee. Just like enduring the subtle “nice progress.” Just like those awkward, harmless flexes from acquaintances.

We’re all trying to build something. A company. A career. A family. A sense of meaning. And the more you zoom out, the more you realize something simple.

No matter how hard you work. No matter how much grit you think you have. No matter how many hours you pour into the thing you’re building.

You are not the main character in everyone else’s story. And that’s not humbling in a sad way. It’s freeing.

The sooner you accept you’re one chapter in someone else’s book, the easier it is to focus on writing your own.

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