That big mirror behind the bar is not there for vanity, it is there because a bartender’s back is turned at the exact moments something can go wrong. We sit down with Tom Ostoyich, a career bartender who has worked since the late 1990s across New York City, New Orleans, and the Hudson Valley, to pull back the curtain on what bartending actually demands and what it can realistically pay.

Then we go to the parts that rarely make it into the glamorous version of nightlife: handling drunk or hostile guests, the legal risk of over serving, strict ID requirements, and the reality of watching for predatory behavior and possible drink tampering. But Tom also shares what's great about the job.

If you are exploring bartending jobs, service industry careers, or tip based work, this conversation is a grounded guide.

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Music credit: Kate Pierson & Monica Nation

About the host: Mirav Ozeri has always been drawn to storytelling and journalism, especially the stories of everyday people.

In the 90’s She founded her own video production company, producing, directing, and editing documentaries and videos for political organizations which led to a 17-year career at CBS News, where she served as a producer/editor, helped launch CBS MarketWatch, and later worked as a senior editor and segment producer until the program was acquired by Dow Jones.

During her years at CBS, Mirav developed and produced a television pilot built around a simple idea: giving people an honest look at what different careers are really like. Although the pilot was never picked up, the concept stayed with her. Years later, she brought it back as How Much Can I Make?, a podcast that explores real jobs, real stories, and the many paths people take to build a career.

A job where your “office” might be a hospital room, a birth center, or a stopped car on a bridge sounds impossible until you hear how a doula actually works. We sit down with Mary Riley, a doula who has supported more than 2,500 births, to unpack what real labor support looks like when plans change, policies shift, and emotions run high.

Then come the stories that make the work feel real: coaching a couple through an unplanned car birth in bumper-to-bumper traffic and the surprising ways memory and trauma can surface during labor.

If you’re curious about hiring a birth doula, becoming a doula as a career or side hustle, understanding doula costs in New York and beyond, or learning how birth advocacy can change outcomes, this conversation will stick with you.

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Trying to figure out what career might actually fit you? Take my QUICK CAREER QUIZ and see your matches, NO EMAIL, NO HUSTLE, just 5 questions:
Visit howmuchcanimake.info

Music credit: Kate Pierson & Monica Nation

About the host: Mirav Ozeri has always been drawn to storytelling and journalism, especially the stories of everyday people.

In the 90’s She founded her own video production company, producing, directing, and editing documentaries and videos for political organizations which led to a 17-year career at CBS News, where she served as a producer/editor, helped launch CBS MarketWatch, and later worked as a senior editor and segment producer until the program was acquired by Dow Jones.

During her years at CBS, Mirav developed and produced a television pilot built around a simple idea: giving people an honest look at what different careers are really like. Although the pilot was never picked up, the concept stayed with her. Years later, she brought it back as How Much Can I Make?, a podcast that explores real jobs, real stories, and the many paths people take to build a career.

We talk with Billy, a Broadway stage manager with 30 years of experience, about what it really takes to run a live theater production. He shares how he built his career, what stage managers do during rehearsals and performances, and how they handle missed cues, technical problems, injuries, and emergencies—all while keeping the show moving.

Billy also explains how to become a stage manager, the skills you need, the demanding Broadway schedule, job security, union benefits, and how much stage managers can earn—from low-paying early jobs to around $200,000 a year at the Broadway level. Plus, hear what it was like working with stars including Dolly Parton, Julia Roberts, Bradley Cooper, and Scarlett Johansson.

If you’re considering a career in theater or curious about what happens behind the curtain, this episode offers an honest look at the pressure, rewards, and earning potential of Broadway stage management.

Explore more creative jobs →

Trying to figure out what career might actually fit you? Take my QUICK CAREER QUIZ and see your matches, NO EMAIL, NO HUSTLE, just 5 questions:
Visit howmuchcanimake.info

Music credit: Kate Pierson & Monica Nation

About the host: Mirav Ozeri has always been drawn to storytelling and journalism, especially the stories of everyday people.

In the 90’s She founded her own video production company, producing, directing, and editing documentaries and videos for political organizations which led to a 17-year career at CBS News, where she served as a producer/editor, helped launch CBS MarketWatch, and later worked as a senior editor and segment producer until the program was acquired by Dow Jones.

During her years at CBS, Mirav developed and produced a television pilot built around a simple idea: giving people an honest look at what different careers are really like. Although the pilot was never picked up, the concept stayed with her. Years later, she brought it back as How Much Can I Make?, a podcast that explores real jobs, real stories, and the many paths people take to build a career.