I’m Charlie Youakim, Cofounder & CEO Of Sezzle, And This Is How I Work



Thanks to Minnesota Tech Startup Supporter Fueled Collective for underwriting our entrepreneur-focused How I Work series!


Sezzle was formed in 2016 initially to pursue ACH arbitrage, and after a big pivot they found a product-market fit by offering online retailers a ‘reverse layaway’ checkout service that allows their customers to pay with installments.

As a result of traction, they received $10m investment earlier this year to scale the team, now 30+ overall.

At the helm is CEO Charlie Youakim, interviewed here to learn about his habits and the the way he operates Sezzle on a typical day — inside and outside the office.

What one word best describes how you work?


What is your current device/hardware/office setup?

I use my cell phone (Google Pixel 2) and a 15” Macbook.

What apps/software/tools can’t you live without?

Google apps, LinkedIn, My cellular hotspot, Slack

What your sleep schedule like in terms of hours and the morning routine?

I usually get to bed around 11 pm and wake up at 6 am. Regretfully, I don’t have much of a morning routine on the exercise front. I typically head right into the office as soon as I can!

Is there a method to how you schedule your days?

I don’t try to structure it too much, but I love tools like Calendly that help reduce the back and forth in the scheduling process.

How much time do you spend in vs. out of the office?

I’m usually in the office for 11 hrs a day. I try to separate the office and home, but when you’re just starting out as a company that’s hard to do. Now that we’re getting some scale to our operations it’s becoming easier to do that.

Where is the office?

We office in Butler North. We really love the location and the office environment.

What’s your best time-saving shortcut/life hack?

Commuting to work on a scooter and parking it on the sidewalk in front of the office.

What is that one thing you have to do, no matter what, every day?

Check our merchant signup count and website traffic.

What is your preferred form of communication and why?

For most of my communication, email works the best because it allows me to reply between meetings.

On average, how many hours a day do you spend in meetings?

3 hours

When, where and what do you typically eat for lunch?

I used to bring in lunch and have it at my desk. But between home renovations, company growth, and travel I don’t think I’ve had a typical day in the last 3 months! Now when I’m in a hurry I usually head down to grab a slice of pizza.

How many hour a week do you work on average and do you work in the evenings and/or weekends?

When we were first starting out, it was a 7 day a week type role. We’ve added some great people to the team, so that’s reduced my time commitment and brought it to levels that can be sustainable. Now I usually work 10/11 hour weekdays and also put in a half-day on the weekend. I bet it averages out to 55 hour weeks.

What is the best advice you ever received, accepted, and applied?

Delegate and elevate. It’s the only way to scale up a business.

Fill in the blank: I’d love to see Mark McGuire from Minnesota’s tech industry answer these same questions.