From Waiting Tables to 7-Figure Success: My 7 Levels of Entrepreneurial Growth

When I dove into entrepreneurship, I dreamed big: building my ideal business overnight, amassing a loyal community, and earning millions from products I loved. With no experience and a tiny network, those dreams crashed hard. To succeed, I needed a mindset shift—a way to 'level up.'

If there's one superpower behind my achievements, it's this: Passion matters, but the term has become clichéd in entrepreneurship lore, often tied to 'do what you love and get rich.' Absolutely pursue what lights you up—you should. Yet it often takes iterations, incrementally aligning your work with your true desires.

Related: 11 Things That Can Trigger Massive Success In Your Life

Level 1

I graduated college in 2009 clueless about my path. My options seemed limited:

• Go back to school.
• Enter the corporate grind.

More schooling didn't appeal—I wasn't drawn to medicine, law, or engineering. Corporate life? The cubicle image alone made me cringe.

Rejecting those paths left me in dead-end jobs: waiting tables, answering phones. I landed at a restaurant chain just to pay bills. It drained me—no joy, no money. Fed up, I took control.

Level 2

In 2012, I quit waiting tables and prepped SAT tests for Kaplan. Was it my dream? No. But it beat slinging steaks—a clear step up.

My $18 hourly rate felt like a win then. But Kaplan charged families over $100/hour, pocketing $82. Unfair.

Level 3

Recognizing my proven skill, I launched my own test prep business, ditching the middleman. Instead of Craigslist hustling, I partnered with private admissions coaches handling essays, interviews, and apps.

I became their go-to test prep expert. Clients flooded in overnight. Win-win.

Level 4

Bored of tests but hooked on business and marketing, I freelanced online—monetizing existing skills. I mastered positioning in crowded markets, copywriting, and closing deals. Soon, my web development agency hit six figures in year one.

Game changer.

Related: What Successful Freelancers Know About Earning Six Figures

Level 5

Online business clicked. I devoured resources on startups, email marketing, copywriting, funnels, and audience-building.

Best move: Launching Rich20Something, my blog sharing a 20-something's frustrations with 9-5 life. An audience emerged organically.

I consulted for brands like I Will Teach You to Be Rich, The Art of Charm, and Pavlok—crafting marketing strategies, funnels, and copy that cut through the noise.

These gigs revealed online dominance secrets. I was primed.

Level 6

In 2014, I went full-time with Rich20Something, solo. No safety net. I created freely, built a following with valuable content, and monetized via digital products teaching freelancing and startups to young hustlers.

Level 7

Now, my team—three full-timers, three interns, part-timers, and dozens of contractors—fuels the mission: Empower 1 million millennials to unleash their entrepreneurial potential.

It's surreal. I've carved a unique career, authored a book on it, and live on my terms.

Ready for your entrepreneurial leap? Ditch others' scripts—level up now.

Related: Quiz: Do You Have the Entrepreneurial Mindset?