Why I Quit My Multi-Six Figure Job at 24 to Go into Business with my Dad

“You can’t walk away, Zach.”

“Dad, I’m not happy!” I retorted.

“Go to the gym, get the energy out, it’ll be better tomorrow,” Ray would say with routine delivery.

We both knew it wasn’t going to magically “be better tomorrow,” yet with exercise and a good night’s sleep, my anger and frustration would dissipate. Ray was seemingly always right. For months he begrudgingly took on the role of “part-time” therapist. My once a week rants became twice a week, then three times, then seemingly everyday.

“Okay Zach, I get it. I think you’re right, now’s as good a time as ever to move on.”

“Validation!” I remember thinking to myself.

Upon receiving Ray’s buy-in, I immediately drafted an email to send to my mentors to get their input. Their responses were all eerily similar, and each began with, “Yes.”

What I thought about before quitting my job

Well, it took me 10 seconds to quit, but it took me over a year of contemplation before I felt confident and comfortable “doing it.” During that year I endured many frustrations, downplayed their significance, convinced myself that things would “get better,” and pursued multiple avenues to transition out of my role and into a new one.

That year was a confusing time for me. I was earning more money than I ever had in my career, I took my girlfriend on a trip to Iceland that involved staying at the most luxurious resort in the country. I had a fancy car, a big house, a lofty title. “Wasn’t this what I wanted?” I remember thinking to myself.

Back in 2008, when I was 12 years old, I created my first website. It was called MoneyMakinGuru.com. I wrote articles about my entrepreneurial endeavors. I had always been attracted to making money.

Here’s a passage from my first website dated May 22, 2008 (grammar errors and all):

If you go to school, or if you have ever gone to school, you know about strict rules. None of the rules are stricter than the no gum rule. Well, if your bad ass like me, you would find away to break this rule, and make some money.

Not all kids have access to food stores to buy gum. So why not become the school supplier of gum. I thought of this idea when I was sitting at lunch and my friends were trading me food for gum. I said if you give me $.25 per piece they are yours. So one of my friends, sorry no names, bought 4 pieces of gum. Then I went into English and re-sold the candy I was traded for the gum. a win win situation. I ended the day with $1.75. $1.75 for the least amount of work I have ever done. My mom had paid a measly $3.50 for 16 pieces of 5 gum. I could have resold the whole pack for $4.00. I would have made $.50. Even though that may sound small, multiply that by all the days in the school year. You would make $95. Now that does sound like some nice money. Considering you would be doing minimal work.

It is just an idea, but maybe it could work for you. Subscribe to my feed if you like this post.

Your friend,


Now that I had money, I realized I wasn’t fulfilled. Cliche, eh? It’s the truth. Yes, money facilitated all sorts of incredible experiences, but it didn’t make me feel complete or whole. If anything, it made me feel disconnected from my peers.

Did I quit my job because of some altruistic, “Eat Pray Love,” go out in the world and “find myself” desire? Partly, yes. The other driving factor? My entrepreneurial spirit to create something of my own. 

You might also enjoy this article if you haven’t read it already: Five Years after Dropping out of College

At MarketSmart I disagreed with the CEO on how to grow the business. I had dedicated nearly one fourth of my life to MarketSmart, and although I carried a lofty title and a lot of sway, I couldn’t persuade the owner of the business to commit to the strategic decisions that seemed necessary to me.

My aspirations to make money, although now muted by having access to pretty much anything I wanted, couldn’t hold me back from vocally bringing to light seemingly obvious ways to grow the business. My primary responsibility as Chief Operating Officer was to be the CEO’s right hand man — to help him navigate operating the business. Hundreds of hours over the course of many years were spent talking with the CEO about business growth. Presentations were made, essays were written, competitive analysis was done… I brought any number of valid ideas to the table for how we could grow and where we needed to invest.

Towards the end of my tenure at MarketSmart, my ideas and aspirations for how to grow the company were vetoed. This misalignment, and the realization that my entrepreneurial spirit could not be fulfilled at MarketSmart, was the primary driver for my decision to move on.

As a strong willed person, you have a limited threshold for being told “no.” While contemplating my resignation from MarketSmart, I recognized that I wasn’t the right fit for the business.

Rather than “clock-in” and receive a paycheck, I decided to quit. This could be youth and naivety, but I simply don’t have it in me to “show up” and get paid. I’m 24. I have too much energy. I want to do something meaningful with the hours I am awake each day. I don’t want to take advantage of a company that has given so much to me.

Getting a nice paycheck and not feeling compelled by what I did that day doesn’t equate to me.

Bootstrapping a new business, from scratch, with my dad

Many business gurus profess you shouldn’t start a company with family members. Fortunately for me (as my first website name made clear), I’ve thought of myself as a “guru,” and with that in mind, I decided not to follow their advice.

I’ve gone into business with my dad, Ray.

This is my second attempt at starting my own company. The first, a subscription service for protein supplements, was a relatively inexpensive learning experience during my freshman year at the University of Pittsburgh.

This business, CarEdge, feels a touch more informed, legitimate, and well thought out.

What is CarEdge

Is it fun buying a car? Think back to the last time you purchased a vehicle. Would you describe the experience as confidence-inspiring, transparent, efficient or pleasant?

For many, buying a car is the second largest purchase they’ll make in their lifetime. However, unlike the largest purchase (typically a home), there is no “agent” there to guide you through the process. Google searching for information, reading tips on how to negotiate, and then going into a dealership to talk to a salesperson appears to be an adequate “status quo” for approaching car sales.

Ray, my father, has 42 years of experience in the retail car business. He’s managed and operated dealerships across the United States representing myriad brands. During his career he’s sold well over $100 million in inventory to consumers. He knows a thing or two about the car business.

CarEdge makes car buying less painful, more convenient, and fun. Instead of walking into a dealership, you have CarEdge do the work for you. We research, locate, and negotiate on your behalf.

You get 42 years of experience on your side, and the comfort of knowing that you’re not getting the runaround by a salesperson. All from the comfort of your home!

Information economy & content marketing

“Yes, that is correct, he is 8 years old and made $26 million last year.” Ray looked at me in disbelief.

“Shit! We should have started when I was younger,” Ray replied with his typical sense of humor.

You might also enjoy this article if you haven’t read it already: How Much Work Do You Actually Get Done at Work?

Ryan’s World, a Youtube channel featuring 8 year old Ryan Kaji, grossed $26 million dollars in 2019. In explaining to my father how this 8 year old out-earned professional athletes, hedge fund managers, and 99.99% of humanity, the lightbulb began to go off.

“Dad, I don’t think we can make that kind of money from Youtube, but there’s a chance. People love information, they like learning, being entertained, etc. Why do you think there are 3 million Wikipedia articles? Because people love information.”

My speech was resonating, and Ray could see where I was going.

“You’re going to want me to make videos, aren’t you?”

Fast forward to today, and 130 people subscribe to Ray’s Youtube channel, with nearly 150 hours of “watch time” in just three short months.

Our desire to teach individuals about the car business, and a commitment to “peel back the curtain” on how it works, are primary drivers of the CarEdge business model.

Content marketing is all about providing valuable and free resources to people. For example, in a recent Youtube video and written guide, Ray explains what credit score car dealers use. The content, which I then posted on reddit went viral (5k upvotes). This is a great example of how hungry individuals are for this type of information.

The reason it is called content marketing, and not content production, is because it serves a business purpose. The free and valuable content is used as a way to educate and inform individuals, who then, on their own volition, will explore your website and online presence. From there, as a business, we have the responsibility (and obligation) to make it clear to a prospective customer what product or services we provide. In the case of CarEdge, it’s the car buying service.

Our strategy is to share as much about the car business as we can. If we do a good job and provide relevant and valuable information to consumers, we feel confident we’ll convert some visitors into customers. And, even if we don’t, Ray feels like he is leaving his legacy for his grandkids to see someday (how sweet is that?).

Be a part of the journey

If you’re interested in following me along this journey, subscribe to my family and friends newsletter. Each month you’ll receive an update on how business is going with CarEdge. If you’re compelled to learn more about the trials and tribulations of bootstrapping a company, you’ll want to subscribe.

Thank you for taking the time to read this.

About the author

I'm Zach Shefska, welcome to my personal website. I'm currently working on CarEdge. I like to travel, write, and make pottery.