They just didn’t know the ending yet.
The Family’s Favorite Son
Growing up, Grant could do almost anything and somehow make my parents proud.
He was older, confident, athletic, and naturally comfortable in the world my parents valued.
He went to the right college.
He graduated on schedule.
He took a respectable position in finance.
Eventually, he joined my father’s investment firm and climbed the corporate ladder.
By the time he was approaching forty, he had become exactly what my parents had always imagined a successful son should be.
He wore tailored suits.
He drove expensive cars.
He knew which restaurants required reservations weeks in advance.
He could discuss markets, investments, golf and business deals for hours.
And my parents loved introducing him.
“This is our son, Grant,” my mother would say.
There was always pride in her voice.
Then there was me.
I had been expected to follow a similar path.
Law school seemed like the obvious choice.
So I enrolled at Columbia.
And then I made what my family considered the unforgivable mistake.
I left.
I didn’t finish my first year.
I dropped out because I had become obsessed with a problem I had encountered while working with transportation companies.
Logistics was inefficient.
Companies were wasting enormous amounts of time and money figuring out routes, warehouse capacity, delivery schedules and load distribution.
I thought software could solve some of those problems.
My family thought I had lost my mind.
My father didn’t yell.
That almost made it worse.
He simply looked at me across the kitchen table and said:
“You’re confusing restlessness with ambition.”
My mother cried.
Grant laughed.
“You’re quitting law school to make an app?”
That sentence became a family joke.
For years.
The Company Nobody Believed In
I started with almost nothing.
I rented a tiny studio apartment in Brooklyn.
My desk was secondhand.
My computer was old.
I had two freelance engineers working with me whenever I could afford to pay them.
There was no glamorous startup office.
No investors waiting outside my door.
No famous mentor.
No guarantee that the company would survive six months.