How I Went From Waiting Tables to Making 7 Figures

May 10, 2017

When I first made the leap into entrepreneurship, I wanted it all.

I wanted to build my dream business overnight, have an enormous community of fans and friends, and make millions of dollars creating products I loved.

Having zero experience and a small network, those ambitions soon sputtered out. If I wanted to succeed, I had to adopt a new mindset. I had to figure out how to “level up.”

If I can trace my success to one thing, if I have one specific “superpower,” it’s this:

Doing work you’re passionate about is important. But the word passion has become a bit played out; everything in entrepreneurship is positioned toward making money doing what you love. Don’t get me wrong, you should work toward doing what you love. But sometimes you’ll have to go through several iterations of this process, gradually leveling up to get closer to what you want and who you want to be.

Related: 11 Things That Can Spark Massive Success in Your Life​

Level 1

I graduated college in 2009 and had absolutely no idea what I wanted to do. I figured I had two choices:

  1. Go back to school.
  2. Join the corporate rat race.

The only problem was that I didn’t want to be a doctor, lawyer or engineer—so more school didn’t make sense to me. And I didn’t want to do the corporate thing. Hell no.

In fact, the very thought of working in a cubicle made me want to throw myself headfirst into a boiling vat of tar. Not very inspiring.

Because I refused to take the next “logical” step, I was stuck in low-paying jobs waiting tables and answering phones. I started working at a chain restaurant to make ends meet, and it sucked. I wasn’t happy and I wasn’t making any money. I was fed up and frustrated. So I decided to take things into my own hands.

Level 2

I stopped waiting tables in 2012 and immediately started doing SAT test prep for Kaplan. Was test prep my No. 1 passion? Of course not. But it was a level up from serving steak. And that’s the point.

My hourly rate was $18. I thought this was fantastic at the time.

 

Was test prep my No. 1 passion? Of course not. But it was a level up from serving steak.

 

But then I found out that Kaplan was charging families more than $100 per hour for me to come to the house and teach little Timmy quadratic equations. In other words, I was doing $100 worth of work, and Kaplan was taking $82 out of my pocket.

Not cool.

Level 3

At that point, I realized I had a viable skill that people had proven they would pay me for, and I decided to level up. I launched my own test prep company, effectively cutting out the middleman and reaping all of the benefits.

I learned that I didn’t have to start from scratch. Rather than scouring Craigslist for clients, I cut the line and made deals with private admissions coaches who prep high school students for their college essays, interviews and packaging themselves.

I sold myself well and became their in-house test prep instructor. Everyone won. Instantly, I went from having no clients to a treasure trove of them overnight.

Level 4

From there, I decided to level up again. I got bored of test prep, but I realized how much I loved business and marketing.

I started freelancing online and got crafty about how to make money using skills I already possessed. Along the way, I learned how to position myself in a saturated marketplace, write valuable copy and close sales. I eventually bootstrapped a web development firm that started pulling in six figures in a year.

Game on.

Related: What Successful Freelancers Know About Earning Six Figures

Level 5

At that point, I realized there was something to this online business thing. I started devouring whatever information I could find about entrepreneurialism, startups, email marketing, copywriting, sales funnels, building an audience and more.

Then I made the best decision of my life and started Rich20Something, my personal blog where I could write about my experience as a frustrated 20-something who knew there had to be more to life than the 9-to-5. I found an audience. Or rather, they found me.

Soon after, I began working with startups like I Will Teach You to Be Rich, The Art of Charm and Pavlok—as an employee in some cases and a consultant in others. They brought me on to develop deep marketing strategies and funnel positioning to help them separate from the pack, as well as to write copy.

From those experiences, I gained the inside scoop on what it takes to dominate an online business. I knew I was ready.

Level 6

In 2014, I leveled up and took the leap of going full time with Rich20Something. I managed it completely by myself.

There was no turning back. I wrote and wrote and wrote and created a following by giving all of my content away for free. I made money by building digital information products and teaching young people how to start their own freelance businesses and online startups.

Level 7

Nowadays, I’ve built out a full team to support my vision of empowering 1 million millennials to embrace their inner entrepreneur.

When I look around me, I still sometimes can’t believe what I’ve accomplished. I have a team of three full-time employees, three interns, a few part-timers and dozens of service providers whom I depend on every week for various tasks.

I’ve made a career for myself that didn’t exist before—the ultimate win.

And I even wrote a book about it.

Are you itching to chase your entrepreneurial dreams? Stop living life on someone else’s terms and level up.

Related: Quiz: Do You Have the Entrepreneurial Mindset?​

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