Two-Time Bootstrapper Decided to Spend More Time with His Family

This SaaS founder bootstrapped his first company and did pretty well when he sold it, but he didn’t want to go back to stressful 80-hour weeks again.

So when he started his second SaaS company he decided to work reasonable hours to spend time with his young family.

He deliberately didn’t raise venture capital or try to create a fast-growing company that would consume him.

That’s one of the ways to succeed as a practical founder. But this didn’t happen last year.

Raj Khera started his second company, MailerMailer, way back in 2001. That’s 10 years before SaaS and web apps and recurring revenue were common.

He ran MailerMailer for 16 years as a steady business that gave him and his family a great life. He sold the business in 2017.

He was a practical SaaS founder 20 years with a lifestyle business, long before it was cool in the software industry to do either of those things.

On the Practical Founders Podcast this week, Raj talked about the decisions he made, the lessons he learned, and how it worked out for him over his long career.

He had a very good business and a great life, but it wasn’t by chance:

“To me, after my first exit, time with my kids was more important. I knew that I would need to pay for that time in some way. And that way was to not build a $100 million a year company.

“Think about what you really want. There’s no right or wrong answer. It was a choice. If you don’t want a $100 million company, it’s not like there’s something wrong with you.

“Enjoy the journey, because if you’re just waiting for the destination you might just drop dead on your way.”

He helped turn around another software company for his third exit. This time it was a VC-funded company.

Now Raj coaches software founders who want to grow efficiently with advanced search engine marketing tactics.

Practical SaaS founders like Raj aren’t new.

But they are far more common now than they were 20 years ago.

Listen to the interview with Raj to hear more about his choices on the Practical Founders Podcast.


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