Let me be really transparent with you: overnight success is myth.

Every successful founder I know has unflattering and embarrassing moments on the road to their eventual breakout, and this story is one of mine.

Go back in time with me to 2024…

For context, this was my life at the time: 

On the weekends I'd start at 6 in the morning and go until noon.

All of that, 7 days a week to maybe make an extra $2,000 a month.

One night while driving DoorDash, an order came in and I recognized the name of a girl I went to high school with.

When her name popped up on my screen, I freaked out.

I was supposed to be the smart kid, the one who was going to do something. 

And now I'm delivering her dinner.

That feeling didn't start that night and it didn't end that night either. 

For eight years, that's just how it felt to be me, like I wasn't ever going to reach my potential. 

Like everyone who knew me was quietly thinking, damn, he turned out to be a loser.

And that feeling didn't go away when I got a better job. 

I left the side hustles behind to work with Oliver at StudyBuddy, making more than all of them combined (at least I wasn't DoorDashing anymore).

The problem was that nothing I spent my time on felt like mine. 

You can't promotion your way out of that feeling, believe me I tried.

That feeling only slowly started to lift when I started working on Cal AI.

I finally had something I could hitch myself to and be proud of. 

And when the first major article got written about me, I posted it everywhere. 

I don't even use social media much, but that one was for everyone who saw me in my DoorDash years and thought I was washed.

The surreal part is the timeline of these events. 

Less than three years separate that delivery from today.

I'm 31 now, which means roughly 90% of my life was simply grinding, trying to make ends meet.

This is true for most successful entrepreneurs.

Ray Kroc was selling milkshake machines into his 50s before he built the McDonald’s empire.

J.K Rowling was rejected by 12 different publishers and didn’t hit it big with Harry Potter until she was in her 30s.

Colonel Sanders didn’t start franchising KFC until he was 62, after his roadside restaurant was killed by a new interstate bypass. 

He was a farm hard, streetcar conductor, and insurance salesman before he made it.

Sam Walton opened the first Walmart at age 44.

So if you're in your DoorDash years right now, eating the embarrassment, dreading the day a familiar name shows up on your screen: you might have to eat it for a while.

Nobody skips that part, they just don't post about it.

But if I can make it, so can you. Keep going.

- Jake