From Waiting Tables to 7-Figures: Rich20Something on the Entrepreneurial Journey

When I first made the leap into entrepreneurialism, I wanted it all. I wanted to build my dream business overnight and 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. And I did.

I figured 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.

Take a look at my entrepreneurial journey here, as I share how I “leveled up,” and how you, too, can get closer to your goals:

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. I didn’t want to do the corporate thing, either. In fact, the very thought of working in a cubicle made me want to throw myself head first into a boiling vat of tar. 

Since I refused to take the next “logical” step, I was stuck at 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.

Related: 3 Crucial Steps to Fail Proof Your New Business Idea

Level 2

I stopped waiting tables in 2012 and immediately started doing SAT test prep for Kaplan. Was test prep my number one passion? No, but it was a level up from serving steak, and that is the point.

My hourly rate was $18, which I thought was fantastic at the time. Then I found out that Kaplan was charging families over $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 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 and interviews. 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 realized how much I loved business and marketing.

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

Game on.

Level 5

At that point, I realized there was something to this whole 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 really awesome 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 got the inside scoop on what it takes to dominate an online business and then knew I was ready.

Level 6

In 2014, I leveled up and took the leap of faith, 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 huge 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.

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Level 7

Nowadays, I’ve built out a full team to support my vision of empowering a 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, the ultimate win. By “leveling up” and following your own passions no matter what, you will get closer to what you want and who you want to be in own your personal entrepreneurial journey.

“Rich20Something: Ditch Your Average Job, Start an Epic Business and Score the Life You Want” by Daniel DiPiazza is available on May 2. Pre-order your copy today at

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