The overnight success that took years: comics, musicians and creators on the long road

October 12, 2026 · 25 min read

Jo Koy describes a long road of false starts, Benny Blanco a long road to his breakthrough song, Joey Diaz comedy's long road, Rick Springfield the long road to Jessie's Girl, Josh Richards four years of grinding that looked like an overnight blow-up, Jesse Cole a decade of experiments and debt before Banana Ball worked, and Ali Siddiq a career built organically. Seeing how long the unseen stretch usually lasts helps people judge their own progress by a realistic clock and not by the moment the public noticed.

12 questions on this insight. Answer in your head, then open the card.
What happened after Jo Koy's first big booking, about five years into stand-up? Show answer

He was booked for a week of roughly twelve shows and told his father it was happening. Then he was booked a couple more times and it stopped.

What did Jo Koy do when Netflix passed on him? Show answer

He shot the special himself, and Netflix then bought it. He says it changed everything.

Why does Benny Blanco say showing up works? Show answer

He insists he has no special talent. If he keeps showing up, he says, eventually the other person might not be there and they will need the next best thing.

How long did Benny Blanco's song Eastside take to succeed? Show answer

Almost two years, including a deal dispute that stalled its release for about ten months. He calls it the longest climb to number one in radio history.

What was Rick Springfield's situation in 1980, eight years after his first American hit? Show answer

He had made four albums that went nowhere and was living in a cheap Hollywood apartment. He took a role on General Hospital for $500 an episode.

How long does Josh Richards say he worked before people called him an overnight success? Show answer

Four years, about three of them on Musical.ly before it became TikTok.

What did Jesse Cole do for ten years before Banana Ball? Show answer

He ran a college summer baseball team in Gastonia, North Carolina, as a laboratory for testing ideas. It drew one media story in those ten years.

What does Joe Rogan mean by being process oriented? Show answer

He focuses on the work and not the results: writing, performing, tweaking, reviewing tapes and talking with friends, so he gets a little sharper every day.

How many followers did Ali Siddiq have when Comedy Central gave him specials? Show answer

About 500 Instagram followers and 300 YouTube subscribers. The network picked him for the work.

What changed Joey Diaz's comedy after his early struggles? Show answer

He stopped focusing on material and rushing, and learned to relax and be himself on stage. He credits Paul Mooney for teaching him.

Where do Jo Koy and Benny Blanco disagree about talent? Show answer

Koy does not believe comedy can really be taught, while Blanco says he has no special talent and showing up is the whole trick. Koy still bombed many times and studied specials with a notebook.

What did Israel Adesanya do when he felt sad for a month after his UFC debut? Show answer

He started therapy, which gave him tools to protect his energy.

This is the short form. The full insight has every expert's reasoning, their own words and the sources.