^{Instagram & TikTok Live}

Let’s Connect IRL! (sorta…)

Quick update before we dive in…I’ve been deep in the funny, satirical side of personal finance lately, but a lot of you said you missed the raw founder stuff.

Starting this week, I’ll be going live (for the first time) on Instagram to talk sales, fundraising, and the messy behind-the-scenes of Habits and startups in general.

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Rage Bait Era

It amazes me how heated people get online. Half the comments were parents calling me a moron, while the other half were fighting about the cost of living.

I hate to say it out loud, but polarizing posts win in 2025. Because algorithm’s LOVE when people disagree online. More comments, more shares, more logins, more scrolls, more time on their feeds, which are perfect for pushing more ads.

It’s really a shame. In my personal opinion, we should have open source algorithms. We should have a say in how our news feeds operate.

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How to Sell When Nobody Knows Who You Are

Early on, everything’s an experiment. And like any experiment, quantity beats quality. If nobody knows who you are, you just have to play the volume game. For me, that meant showing up on LinkedIn because every financial advisor lives there, and it’s one of the few platforms where people aren’t a mystery. You can see their education, experience, and personality. It was my CRM before we had one.

Over time it stopped being about volume and became about precision… perfecting the pitch, the follow-ups, the materials, and learning how to adapt when nothing goes to plan.

The First “Yes”

My first sale was at a coffee shop in Indianapolis. Just me, an iPad, and an advisor who had every reason to say no. I pitched him on this simple idea: “Wouldn’t it be awesome if the exact kind of clients you love working with could find you easily, simply, and securely?”

He paused and asked, “So what do I get if I pay $750 today?”

I told him, “I can guarantee I’ll get you one new client.”

That’s how it started…pure belief and persistence. The average CAC for a new client in this industry is over $4,000. Ours was a fraction of that because we relied on humanity and storytelling, not ads, gimmicks, or having 100 bank branches in the area.

You don’t need a perfect product to sell, you just need a believable promise.

The Travel Grind

For the next two years, I basically lived out of my car. I split time between Indianapolis, Chicago, Boston, and New York, chasing meetings, pitching advisors, and trying to prove Habits was real. My girlfriend was in PA school doing one-month rotations, so I followed her to random towns like Louisville and Fuquay-Varina, North Carolina, setting up shop anywhere with Wi-Fi.

I’d drive 10–14 hours, take calls from TikTok or LinkedIn leads, and pitch total strangers while flying down the highway. There were moments mid-sale when I’d lose signal in the hills of West Virginia or Pennsylvania, the call would drop, and I’d just sit there laughing because that’s how it goes. No polish, no script, just learning in real time.

That road-warrior phase gave me reps. Thousands of conversations. Thousands of data points. It’s how I learned what people actually wanted and what they didn’t.

You can’t sell what you don’t understand and you only understand it by talking to people nonstop.

Selling to Families Was Easy. Getting Attention Wasn’t.

For families, our pitch was simple: “Here are three advisors who fit your stage of life, your budget, and your personality.” That honesty built trust instantly.

But what most people don’t realize is we’ve done over 3,000 one-on-one Zoom calls with users. It’s easy to sell when someone’s sitting across from you. What’s hard is breaking through the noise to get that call. You might have five seconds of attention these days…if you’re lucky.

That’s where I learned the real battle isn’t selling the product. It’s selling the click.

Attention is the hardest currency in the world right now.

When Credibility Finally Caught Up

People didn’t start taking Habits seriously until this year. Financial services runs on reputation.

In January, we announced our raise and won a pitch competition. We later won “Best in Show” at Morningstar’s FinTech Showcase. We opened an office in One World Trade Center.

But none of those moments defined us. Credibility doesn’t come from a viral video or big announcement. It comes from stacking small wins daily.

Every email reply. Every DM answered. Every advisor call where someone hangs up and says, “These guys actually give a shit.” That’s what builds reputation.

Credibility isn’t a moment…it’s a muscle.

Selling the Future

These days, the hardest pitch isn’t about today, it’s about the decade ahead.

We’re a team of seven. We have real revenue, real users, and a product that’s finally humming. But we’re still so early. Veera and I talk constantly about what’s next: rebranding, scaling, evolving Habits from “the place to find an advisor” to something that lives in people’s daily lives.

That’s the pitch now: convincing people to see what we see before it’s visible.

The hardest sale is the one that hasn’t happened yet.

What I Wish I Knew at the Start

Less is more. Always.

Whether you’re DM’ing an advisor, persuading a young parent, pitching a partner, or recruiting a team member simplicity wins. Shorter copy. Simpler workflows. Cleaner websites.

You’ll hear “no” 99 times out of 100. The trick is to get through the 99 faster and learn from the one yes that worked.

Because sales is everything. It’s how you grow your revenue, your brand, your team, your investors, and yourself.

The simpler your message, the faster people believe it.

Final Takeaway

Selling when nobody knows who you are isn’t about tricking people, it’s about earning attention through honesty, repetition, and clarity.

If you want to be heard, simplify. If you want to be remembered, persist.

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