Betting on Yourself: How Ali Schwartz Left Corporate for Music
For most of her twenties, Ali Schwartz ran two lives that were not supposed to touch. In one, she was a sharp corporate operator, climbing from sales rep to business engagement and events lead at Yelp and eventually into a director-level role at Fortune Media. In the other, she was a singer, songwriter, and dancer writing songs in what she calls the singing closet, quietly convinced the music was only ever a hobby.
On the newest episode of Success, Rewritten, Ali sits down with host Emily LoMenzo Washcovick, who worked side by side with her at Yelp for years, to trace how those two lives finally converged. It is a conversation about treating creativity like a business, redefining success once you actually hit the numbers you were chasing, and why real progress moves so much slower than social media makes it look.
From the "singing closet" to center stage
Ali grew up around creativity and entrepreneurship in equal measure. Her dad spent more than 40 years in theater, her mom ran her own practice, and her grandfather ran his own business. But pursuing music never felt like a real option. College, a business and marketing degree, and a corporate job were simply the societal default, so that’s the path she took, and she treated singing and dancing as something she did on the side.
The turning point came in 2019, when she rented a venue, sold tickets, and headlined her own concert. Emily was in the room. That night is when the hobby stopped feeling like a hobby, and Ali started asking a bigger question: what would it look like to make music that sounded as professional as the vision in her head?
Treating creativity like a business
Ask Ali what she does and she will not lead with glamour. She is an entrepreneur who happens to sing.
"I run my musicianship like a business, and that's where I've seen the most success from it."
No two days look the same. She writes for other artists, records vocals she sells to producers, works on her own EP, teaches for DivaDance, and choreographs. In practice that means wearing the social media hat, the accountant hat, the CFO hat, and the creative director hat, often in the same afternoon. The through line is that she stopped waiting for permission and started operating like the business she was already running.
Why 20 million streams is not the finish line
Here is the part that reframes everything. Ali now has over 20 million streams and more than 5 million views in the past year. If you had told 2019 Ali those numbers, she says, she would have assumed her work was done. Instead, hitting them taught her they were never the real scoreboard.
"It's not the views and it's not the numbers to me."
In corporate, the ladder gave her a clear next rung: manager, senior manager, director, VP. As a full-time creative, she had to build her own definition of what a promotion even means. These days she measures a concert less by headcount and more by a feeling that is genuinely hard to quantify. Did she put on her best show? Did she connect with the people there? Did they walk out lighter than they came in? Her most recent concert had less people than the one before it, but she counts it as more successful because she added live dancers and grew as a performer.
The corporate skills that built her music career
Ali is quick to reject the idea that her corporate years were time away from her real work. The event planning, the relationship building, the ability to read a room and adjust her energy in real time, all of it transfers directly. She learned to handle tough crowds at Yelp with what Emily calls a “strategic sweetheart” approach: kindness at the forefront, but with enough backbone to keep an event moving when one person tries to hijack it. She would not be able to produce her shows at the level she does now without that experience.
The leap, and the reality she refuses to hide
When Fortune Media offered a director-level role, it checked every box. Bigger title, more money, growth on paper. Then she got there and the fulfillment never arrived. She credits her husband with naming what she could not: the music lit her up, and she was spending her days waiting for the clock to run out so she could go work on it.
She is also refreshingly honest about what made the leap possible. Savings from years in corporate, a husband who supported her emotionally and financially, parents who helped put her through college, and no debt. Plenty of people who look more successful on paper cannot walk away from a steady job, and she is careful not to pretend otherwise. Naming that privilege is part of telling the story truthfully.
Building community with Pop Hang
One of the things Ali loved most about the Yelp role was connecting people, and she has carried that straight into music. She runs Pop Hang NYC, a free community for artists, producers, and songwriters in New York, with partners that have included Warner Music and BMI. The goal is to put the person about to release their first single in the same room as someone about to release their third album. The producer she is making her current EP with came through a friend of a friend at one of these events, and her last two concerts featured people she met there.
"Collaboration is key. There's enough to go around."
Progress is an ice cube melting
The line that stays with you from this episode comes near the end. Ali borrows an image from Atomic Habits to describe what a decade of building has actually felt like.
"Progress is an ice cube melting, and you have to be okay with that."
You can do a huge amount of work before anything visibly changes. There is no silver bullet and no single viral moment that hands you a career. For anyone weighing their own pivot, that might be the most useful thing she says: the paddling under the surface is the job, and meaningful success asks for patience and a lot of grace.
The new episode of Success, Rewritten with Ali Schwartz is live now. Watch on YouTube or listen wherever you get your podcasts! (Spotify)
