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Why Habits?

If you missed it, I just concluded a 6 week series on all the firsts for Habits. Consider things like our first sale, how I found my co-founder, our first investor, attracting early employees, our first VC investor, how to manage F&F, and today I felt compelled to share some stories.

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Founder Fuel

The best part of any job? The people. I’ve always learned more from stories than textbooks, and perspective never hurts.

You can learn something from literally anyone.

In the beginning, I took every call with anyone who’d listen. Then social media blew up, and suddenly, we became THE place to find a financial advisor if you’re 25-45. Remember, for startups it's all about niche first - empire later.

Hence why we launched a mobile app to automate the whole process, but now I don’t get to meet as many families. And I miss that.

Me after hearing “Jack we need you to talk with 50 users during the outage…”

In true startup fashion, a tech glitch had me personally texting 50 users this week. Not ideal. But those convos reminded me why I do this.

Nothing beats hearing, You changed my life. Or That 30-minute call was better than I imagined. Those moments fuel everything.

But a startup eventually shifts from product to company-building. My job now? Training a team, building processes, and making sure every user feels valued (easier said than done).

A couple weeks ago, I felt burnt out. Happens. But talking to users keeps me going. It’s something special. And I know I’m very very very lucky to be in this position.

So, I want to share a few quick stories from the past week—four different Habits users, each in a different stage of their financial journey. Maybe you’ll see a bit of yourself in one of them.

For the record, these are real people who have allowed me to paraphrase their stories, experiences & messages for this blog post.

Single, 29

Job: UX Designer @ Tech Startup
Income: $110,000/yr
Net Worth: $40k
Location: Denver, CO

Her Story: “I was the friend who always had a financial plan. Maxed my 401(k), invested early, never carried credit card debt. But after years of grinding, I woke up one day and realized I had built a future-proof life… that I wasn’t actually enjoying. My ‘fun’ budget was nonexistent. So, I finally loosened my grip—moved somewhere I love, started traveling more, and let myself live a little.”

Her Advice: Being responsible doesn’t mean being boring. Money is a tool, not a trophy—use it to build a life you actually want.

Engaged, 34 & 31

Job: Engineer @ Aerospace Company, HR Manager @ Fortune 500
Income: $220,000/yr combined
Net Worth: $150k
Location: Raleigh, NC

Their Story: “We’re in that weird in-between stage—doing well financially but feeling stuck. We make good money, we save, but we also have a wedding, a house hunt, and maybe a kid in the next few years. And honestly? The thought of balancing all that makes our heads explode. We don’t want to be the couple drowning in mortgage debt or delaying kids because we ‘can’t afford it.’”

Their Advice: The biggest financial stress isn’t a single purchase—it’s stacking multiple life changes at once. Plan ahead so you don’t feel buried.

New Parents, 37 & 35 with a 6-Month-Old

Job: Marketing Director @ Consumer Brand, Pharmacist
Income: $280,000/yr combined
Net Worth: $400k
Location: Minneapolis, MN

Their Story: “We thought we were prepared for parenthood. What we weren’t prepared for? How expensive everything is. Daycare is a mortgage payment. Our grocery bill doubled overnight. Suddenly, saving feels impossible, and we’re questioning if we should be putting everything into 529 plans, real estate, or just trying to keep up with life.”

Their Advice: There’s no ‘perfect’ way to prepare for kids financially, but building flexibility into your budget is key. Life comes at you fast—make sure you can adapt.

Divorced Dad, 41 with a 10-Year-Old

Job: Product Manager @ Big Tech
Income: $250,000/yr
Net Worth: $750k
Location: Austin, TX

His Story: “I spent my 30s building a career and a family… and then life zigged when I thought it would zag. Divorce shook up everything—my finances, my priorities, my entire sense of stability. Splitting assets and covering two households isn’t cheap, but the real challenge was figuring out how to start fresh financially and personally.”

His Advice: Life doesn’t always go as planned. A solid financial foundation gives you options when you need them most.

What’s Coming Next?

A lot of you have asked for more versions of the “day in the life” type content. This time I’m going to try my best to document and share everything I’m doing next week, which also includes travel to NYC and Boston. Stay tuned!

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