How 5 Gen Y'ers Went From Uncertainty to Success

These tales of inspiration should prompt you to ask yourself, 'is this all there is for me?'

learn more about Dan Feld

By Dan Feld

EXP Adventures

Opinions expressed by Entrepreneur contributors are their own.

It’s safe to assume that at some point you’ve reflected on your career path and wondered, “Is this all there is for me?”

Answering that question led me to experience the biggest failure of my life: quitting my New York City desk job of the past five years to become a school teacher in Mississippi, only to end up quitting on the first day of school and moving back in with my parents. Yes, really.

However, on the other side of my failure was the idea for a project that would answer my original question.

Related: 5 Killer Lessons I Learned from Interviewing World-Class Entrepreneurs

"Prologue Profiles" is a podcast series I host featuring intimate and honest interviews with Gen Y’ers taking risks and making their career dreams happen. I call them "Generation Why Not." I’ve hand-picked several stories I think you would find most inspiring as you continue along on your own journey.

1. Milo Pierwola: Professional Adventurer

After college Pierwola became a lawyer because, well, he didn’t know what else to do with his mathematics degree. But Pierwola didn’t want to be a lawyer -- he wanted to travel, and he set a life-changing goal for himself: “to be a profitable world traveler.”

He is now the founder of EXP Adventures, which creates personalized travel experiences around the world. (Um, what?)

Listen to Pierwola's interview here.

2. Loren Brill: Baking Entrepreneur

After college, Brill wasn’t sure what she wanted to do for her career. Then, her lymph nodes became swollen and she was diagnosed with cancer.

Brill got serious about her diet, learned about whole foods and developed a passion for baking. She took cooking classes and came up with all-natural dessert recipes.

Brill recovered from her illness and worked several desk jobs while the desire to get back into baking grew stronger. She entered and won a baking competition, which gave her the confidence to launch Sweet Loren's, featuring all-natural desserts that are available at Whole Foods and Fresh Direct.

Listen to Brill’s full interview here.

Related: 3 Millionaire Entrepreneurs You Probably Haven't Heard Of (and How They Did It)

3. Andrew Livingston: Fashion and Manufacturing Entrepreneur

Originally from California, Livingston grew up a professional snowboarder and competed nationally in soccer in high school. But a back injury ended his sports career and gave him two options: live in misery or pick a new passion.

Livingston was always into men's style, so he dove head first into fashion. He would identify a hole in the market based around the typically unglamorous world of manufacturing. Livingston dropped out of New York University, raised the money needed to buy an old hat factory in Brooklyn on Kickstarter and co-founded Knickerbocker Manufacturing Co.

Knickerbocker creates white label products for entrepreneur designers, collaborates with up-and-coming brands such as Blind Barber and sells its own men's collections.

Listen to Livingston's full interview here.

New York Called

4. Taryn Multack: Nail Art Entrepreneur

Multack thought she’d become a fashion designer, but in college she realized designing wasn’t for her.

While working at Macy’s corporate, she attended New York Fashion Week for the first time and was so inspired by what she saw on the runway that she went home to replicate the designs -- on her nails. Multack had been into painting her nails as long as she had been into fashion.

Multack tweeted out her nail art to beauty editors and got the attention of Teen Vogue and The Huffington Post. She made a new design every Tuesday for two years and is now better known to her 525,000 Tumblr followers as Miss Ladyfinger, collaborating with brands such as Maybelline and Seven Jeans.

Listen to Multack’s full interview here.

John Lee Dumas

5. John Lee Dumas: Podcast Entrepreneur

After serving in the military, Dumas found himself dreading his commercial real estate job and especially his commute.

While driving to work he loved listening to podcasts -- but he couldn’t find any shows that put out a new episode every day. Dumas saw an opportunity and launched "Entrepreneur On Fire," a daily podcast featuring interviews with successful entrepreneurs.

Dumas now brings in over six figures a month from his show and online podcasting community, Podcaster’s Paradise. He breaks it all down to the penny in his monthly income reports. Incredible.

Listen to Dumas’s full interview here.

Related: How a Kid in a Gang Became a Multi-Millionaire Entrepreneur

Dan Feld

Host of Prologue Profiles and Speaker

Dan Feld is the creator and host of the podcast Prologue Profiles, which features interviews with young entrepreneurs and artists taking risks and making their dreams happen. Feld also speaks at colleges and to young professionals to help audiences get out of their own way and get what they want for their career.

Subscribe and listen to Prologue Profiles on iTunes

Related Topics

Editor's Pick

Have More Responsibilities at Work, But No Pay Bump? Use This Script to Get the Raise You Deserve.
Black and Asian Founders Face Opposition at All Levels — Here's Why That Has to Change
Business News

'This Made Me Physically Recoil From My Phone': Lingerie Brand Apologizes For 'Creepy' Ad Referencing Ryan Reynolds and Bras

Online lingerie retailer Harper Wilde is under fire for a bizarre sponsored post it has since pulled from Instagram.

Thought Leaders

5 Small Daily Habits Self-Made Millionaires Use to Grow Their Wealth

We've all seen what self-made millionaires look like on TV, but it's a lot more subtle than that. Brian Tracy researched what small daily habits these successful entrepreneurs adopted on their journey from rags to riches.


Blake Lively Knows Being a Perfectionist Is 'Weaponized' Against Women, But She's Micromanaged Her Way to Millions, So She's Not Stopping Now

The "Gossip Girl" actress is done apologizing for being a control freak. After all, obsessing over every little detail is what's made her mixer brand Betty Buzz a raging success.

Business News

Viral Sensation 'Popcorn Guy' Has Earned a Gig at the 2023 Oscars

Jason Grosboll first went viral on TikTok for his theatrical method of buttering popcorn in a Texas movie theater.