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De-Influencing Financial Hardo’s

I love poking fun at financial influencer’s. So many of them talk sh*t about financial advisors or the industry as a whole, but then proceed to monetize credit card signups, clicks on their referral links, or selling the contact information for who join their “masterclass.”

And the video below is on pace to cross 3M views, so I think it’s safe to say that others agree with me.

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24K followers

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You can also watch this on Tiktok.

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Hiring Is Hard as Shit

I used to think hiring was about résumés, credentials, steller applications, and interviews. My first job at JPM? They bragged that 250 of us were picked out of 10,000+ applicants. So I had this mindset that I earned it, that I was special.

But here’s the truth: most hiring is luck. Right place, right time, and said the right thing in an interview. Over the years, I’ve come to accept that hiring is one of the most difficult parts, if not the hardest thing to do right at any organization . attitude and personality often matter more than skillset. People have to be able to do the damn job, sure. But the real differentiator? How they show up.

The Habits Way of Hiring

Veera and I talk about people almost every day. Our model at Habits is unusual compared to most startups. Almost everyone we’ve hired full-time first came through an apprenticeship or internship.

It’s simple: 5–20 hours a week, you get dropped into the chaos. We see how you handle it, then give you more responsibility. By month three, we usually know if it’s worth carving out budget for you.

Why? Because people can sound amazing on paper. Ivy League backgrounds. Former CROs. Ex-founders. Flashy LinkedIn résumés. But you don’t know someone’s true value until they’re in the trenches with you.

The best interview process is real work, not polished answers.

The One That Got Away

Back in 2022, Veera and I thought we found our first big hire. Well, I did at least. This guy was one of the first 500 employees at a major tech company, spent nearly a decade there, loved personal finance, and had the perfect blend of skills. He founds us through TikTok and reached out directly.

I spent four months training him. Nights, weekends, walking him through our MVP, bringing him into calls, teaching him our playbook. And it was especially time consuming because I was doing all of this while still working my 9-5 consulting job. The whole idea was to get him ready to go, and I’d join shortly after.

His first week on his own? He calls me on Friday and says, “Hey man, I don’t think I’m cut out for this.”

LITERALLY one week. After months of prep. We’re talking 10hrs+ every week on Zooms and calls. I literally said under my breath “what the f**k.”

Looking back, it was a blessing. But it was also proof that even if someone checks every single box, you don’t know until the work starts.

Hiring is a gamble. Sometimes the “perfect fit” folds on Day 7.

The Gift Card Guy

You literally can’t make this up. Veera still gives me a hard time about it.

Not all hiring horror stories end cleanly. Early on, we hired someone through a close friend’s referral. This guy was a former pro athlete, had tens of thousands of followers, went to a top MBA school…basically a perfect situational hire, right?

Two weeks in, he calls me frantically. Turns out, he got a random text from someone pretending to be me. BRO FELL FOR THE OLDEST TRICK IN THE SCROLL. Someone convinced him to go to Target, buy four $250 gift cards, and send the codes.

I was stunned. I did end up reimbursing him $1,000, even though at the time I was broke, living out of a buddy’s rental, and could fit all my possessions into a single car. It hurt. And after that? It just didn’t work out.

A good résumé can’t fix a lack of common sense.

When It Works

Not all stories are bad. Sometimes hiring works so well it’s electric.

One of our early apprentices came through with hustle and humility. The kind of guy who, if you gave him a list of 100 cold calls, he’d knock them out without flinching. We threw him into everything — cold calls, HubSpot campaigns, designing in Figma, even website projects. He took it all with enthusiasm and executed.

Last week, we gave him a full-time offer. That’s what you want to see.

Another win? A world-class marketer referred by an angel investor. She only worked with us for a few months but left us with the bedrock of our entire marketing philosophy. A ten-page Google Doc she put together in 2024 still gets referenced by the team today. She’s now crushing it at an incredible job, likely making seven figures, and we couldn’t be happier for her.

The right people elevate everything. Even short stints can shape the company for years.

Closing

Hiring is hard as sh*t. Most people won’t work out. Résumés lie. Perfect fits walk away. You’ll get burned.

But when you get it right, it changes everything. That’s why we keep taking bets. Because behind every cold call, résumé, apprenticeship or internship, there’s always a chance the next person you bring on isn’t just an employee…they’re the one who helps level up the whole company.

The wrong hire sets you back. The right hire changes your trajectory.

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What’s Coming Next?

Next week I’m going to break down a typical day in the life. I think we all love to see that type of content on Insta or TT, but not so much a breakdown of my schedule. More what’s going on inside my head as each hour passes and the problems that erupt.

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