Startup Luck is Important, But How Do You Define It?

by | Mar 2, 2025

Every practical SaaS founder I know works hard, takes risks, and does things normal people don’t do—for a long time. But how much of our successes came from “luck” as we define it?

Most things we do don’t work out so well, but some things work very well.

A few things (sometimes) turn out to be game-changers.

  • I think luck is a necessary part of the success equation. It comes in many forms:
  • Great timing to start or sell your business
  • Being in the game with enough tries to have opportunities for luck
  • Recognizing and acting on opportunities that come up
  • Being the right founder for the right product

Howard Gottlieb started Read-A-Thon in 2012 as a reading-based fundraising platform that helped students raise money while boosting education.

Their easy platform and simple fundraising approach created amazing results.

The Read-a-Thon business grew steadily and profitably without any outside funding.

Read-A-Thon helped over 4000 schools and students raise over $30 million in donations. Their platform has tracked over 30 billion reading minutes by students who have used it to earn donations.

Read-A-Thon was successfully acquired by private equity investors in early 2023 for an undisclosed amount.

The business has continued to grow and expand with a new CEO and key executives, with Howard on the board as an advisor and now a minority investor in the company.

He’s a 6-time entrepreneur who is very savvy and works very hard, but he knows there was some useful good fortune along the way:

“I have been very blessed and very lucky in my journey with the success of Read-A-Thon. Everyone should realize that and have some humility.

“If you succeed at the game, you can be the smartest guy or the smartest woman with the most brilliant idea, but it still will take 50% or more luck for everything to align correctly to succeed. Just realize that. It takes a lot of good fortune.

“At Read-A-Thon, our lucky moment was COVID because online fundraising was only in its infancy. When COVID hit and schools were out, Read-A-Thon was almost the only viable option. Our growth went from 40% a year to 100%, then 150% a year. So that was luck after all these years.”

Every founder I know has a different version of what luck has meant to them.

How do you define luck in your entrepreneurial adventures?

Check out this amazing interview with Howard Gottlieb on the Practical Founders Podcast. https://lnkd.in/g35fnHne

I wish you good luck when it matters most.

Greg Head posted this on LinkedIn on March 2, 2025.

Check out the comments and join the discussion on LinkedIn.

Related Posts

Gregslist Phoenix is Now Curated by PHX FWD

This week, after almost 10 years, my Gregslist of Phoenix Software Companies officially moves to a new home and a new host at PHX FWD at https://www.phxfwd.org/the-list. I created Gregslist.com/Phoenix as a comprehensive, curated, and ...

Unsexy SaaS is Cool Again

Biographies of successful entrepreneurs share one lesson that you won’t read about in most “how-to” business books: None of the wildly successful and famous people started out that way. They were just “normal” people who did very abnormal ...

Where Are All The $100M Bootstrapped SaaS Success Stories?

If SaaS and AI software bootstrapping works so well, why don't we hear about more $100M ARR independent success stories? There are far more bootstrapped software companies in the world than VC-funded ones. Yet when people think about big ...
No results found.