^{Job Opportunity at Habits:}

We’re Looking for a Young Designer to Help Us Rebrand Our Startup

It’s been over three years since we touched our branding and we’ve grown a lot since then. So we’re opening up a rare opportunity for a student or recent grad to help us reimagine our entire visual identity.

We’re talking logo, font, mobile visuals, animations, and more.

This isn’t just a side project. The chosen designer will:

• Get full creative freedom

• Work directly with our founding team

• See their work featured on a startup that reaches millions per month

• Be paid, flexible, and supported by a team that’s been in their shoes

We could’ve hired a professional agency. But we’d rather offer someone their big break—because that’s how most of our team got started, too.

Check the details below or PLEASE SHARE this with you who believe is a great fit.

Let’s build something iconic.

^{Paid Advertisement:}

Find Your Financial Advisor with Habits!

For a limited time, I’m making myself available for any of you considering if a financial advisor is right for you or your family.

Needless to say, it’s been a spooky start to the year with elections, geopolitical tensions, tariff wars, and market volatility.

Just do me a favor, download the app and click the link below to find time.

Also, did you know I’m available via text? You can reach me at ‪(812) 805-0099.

^{Main Story:}

Why I Pitch VCs Every Quarter (Even When I’m Not Raising)

Every quarter, I block off two days and stack back-to-back VC meetings, but we’re not raising. And it’s not a vanity thing. It’s not “warming people up” either.

It’s about sharpening the sword. Pitching is a different headspace than building. It forces me to level up how I talk about the business—quickly, clearly, confidently.

There’s no better way to stress-test your story than to repeat it eight times in a row to people who don’t owe you a damn thing.

The Pitch Mindset Is Just Different

On pitch days, I wake up in a different mode. I’m not thinking about team updates or bug fixes. It’s only about distribution, product traction, and value props. I’m asking myself:

That mindset bleeds into everything. Consider how I prioritize, what content I create, what updates I push. It creates a momentum that’s hard to replicate during a regular week of ops and logistics.

The faster you can switch between operator and evangelist, the better founder you become.

Pre-Revenue = Story. Post-Revenue = Proof.

When you’re early, no one expects data. They’re investing in you, your obsession, and your take on the world. It’s vibes, clarity, vision.

But once there’s revenue on the board, vibes won’t cut it. Investors want to see traction. They want a story of progress—month-over-month growth, not just momentum theater. It’s about whether your team has the edge, the moat, the obsession to iterate your way to something real.

And for us? Product-market fit isn’t a fluffy milestone. It’s when CAC drops, conversion spikes, and capital becomes fuel (NOT oxygen).

Once there’s money in the system, the story shifts from what could be to what’s already working.

Where Habits Is Right Now

We’re not at PMF yet—but we’re past the “is this even real?” stage. Habits has a working product, strong engagement, clear pain points on both sides of the marketplace, and a real GTM engine (sorta - Hubspot frustrates the f**k out of me) with organic growth. And we’ve done all that in the most crowded and competitive space you could pick: fintech + advice.

So here’s the deal, any VC who wants to play here has to believe we can get to $5M+ ARR and punch our way into Series A territory. That belief doesn’t come from pretty decks or witty copy. It comes from proving that this team can compete, adapt, and win.

In other words, investors don’t give a sh*t that I crossed 25k followers on a new social media channel, had a video achieve over 2M views in 48hrs, or added 10 new firms to our sales pipeline.

When the category is saturated, conviction matters more than optimism.

What I Want to Know About VCs

I don’t walk into a meeting trying to impress someone I know nothing about. That’s a waste of both our time. I research ahead of time. In the early days it took 30min, and now it takes 5min. I mostly want to understand how they think.

• Who am I meeting with, specifically?

• What’s their mandate or investment philosophy?

• What types of companies do they actually get excited about?

• What’s their average check size? Do they lead or follow?

• What are some recent investments, and why did they lean into those?

• Which portfolio company are they personally most fired up about?

• Are they raising a fund? Where are they in the fund cycle?

• How many more investments are they planning to make this year?

• Do they co-invest often, and if so, with whom?

• What do they read, talk about, reference all the time?

• Who in their portfolio company would complement us?

• Have they made any recent investments in our space?

And if I can’t find that info online, I ask. But only after I know they’re even remotely interested in what we’re building. Otherwise, it’s just noise.

If a VC can’t see themselves investing in your space or model, nothing else matters, not even the “right” answers.

How I Run a Pitch Meeting

I don’t do the slow warm-up. I get right into it. Deck or no deck, I break down the business as directly as I can: revenue, burn, engagement, retention, GTM, CAC, LTV, momentum. The metrics VCs actually care about.

Then I ask a simple, pointed question:

If they’re out, cool. If they’re curious, I’ll start asking questions that help me position better and understand whether this could be a fit. I’m listening for alignment, not approval.

At this point, I’m not trying to chase a yes. I’m trying to avoid wasting time.

The best founders don’t chase capital. They create urgency.

Why I Don’t Take Any Meeting Personally

Let’s be honest…95% of the people you pitch are going to say no. Not because your startup sucks, but because they’re tired, distracted, in-between fund cycles, or already mentally committed to something else.

Sometimes you’re meeting with someone who just spilled coffee on themselves. Sometimes they’re running on no sleep because their baby was up all night. Or maybe they’ve already seen five founders that morning and just don’t have the bandwidth to really hear you.

That’s why I can stack eight meetings in a day and not spiral. I walk in, feel it out in five minutes, and either shift into high gear or cruise through the rest of it. There’s zero ego in it anymore.

Rejection is just a signal. The sooner you read it, the less it stings.

Final Thought

Someone I think highly of (meaning a mentor who is just a f**king master story-teller and visionary and crushes everything he touches) once said to me “you’re always thinking about raising or always closing a round.”

And the key takeaway to that statement is you’re always fundraising.

Because if you only pitch when you’re raising, you’ll show up rusty and desperate when it matters most.

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