Member-only story

MORE BETTER MISTAKES

How to Make Big Money Without Taking Big Risks

You have to spend money to make money, but you don’t have to spend it all at once

Sanjay Singhal
Said Differently
Published in
6 min readApr 25, 2024

A man jumping over a chasm (and probably falling)
Maybe you should have tried that in your backyard first — Midjourney

My friend Vicki asked me after a yoga lesson if I could write an article on how to make money. Before I could say anything, she added, “I know you take risks, and I know I’ll have to take a risk if I want to expand my business. How do I get over my fear of risk?”

“Well…” I started, and she interrupted again.

“And don’t give me advice that requires a lot of money. I don’t have $500,000 lying around to invest in my business. In fact, nobody who reads an article on how to make money has any money. Ok, go ahead.”

I took a breath and waited. Vicki looked at me expectantly.

I finally said, “OK, I’ll give you a preview. The trick is not taking big risks at all. Most of the things you’re going to try will fail. Make lots of little mistakes and when something works out, then you spend a lot of money on it, when it’s already de-risked.”

And I told her a story.

I founded a company called ‘Simply Audiobooks’, which was an okay name, but what I really wanted was ‘Audiobooks.com’, the number one result that came up when you typed…

Create an account to read the full story.

The author made this story available to Medium members only.
If you’re new to Medium, create a new account to read this story on us.

Or, continue in mobile web

Already have an account? Sign in

Said Differently
Said Differently

Published in Said Differently

Said Differently is a home for unorthodox thinking that challenges lazy consensus views. Are you a careful observer and a clear thinker? You can help cut through the confusion by pointing out what the experts get wrong.

Sanjay Singhal
Sanjay Singhal

Written by Sanjay Singhal

I write about how to manage your career and life by telling stories about how I've botched my own career and life.

Responses (54)

Write a response