Building A Software Company And A Life With Your Family At The Same Time

Most founders who sell their companies eventually start another company or create a new project. Old habits die hard for most former founders.

But there’s also a type of software company founder who intentionally built a valuable software company AND built a life with their families and interests at the same time.

They worked hard to build their profitable SaaS businesses so they could spend more time with their families and interests than in their businesses.

These founders generally have an easier time getting out of the entrepreneurial grind after they sell their companies.

Tech investors use the negative term “lifestyle business” to put down these companies and poke at the founders.

But these companies can be growing, profitable, defensible, and very valuable for founders and their teams. They just aren’t beholden to outside investors at all.

Joshua Strebel and his wife Sally bootstrapped their platform-as-a-service company Pagely® for 15 years before they sold it to GoDaddy in 2021 for a life-changing exit.

Only their lives didn’t change much after they won their big exit prize.

They already had serious profits for many years, lots of time with their family, and plenty of time for other interests.

As Joshua describes on the Practical Founders podcast this week:

“‘Lifestyle business’ was a naughty word to a lot of people. I began to use that term with pride and sarcastically and say, ‘Oh yeah, a lifestyle business sucks…unless your lifestyle is funded by a seven-figure income!’

“Sally and I discussed that this opportunity of being entrepreneurs allows us to raise our own children, and that was important to us. We don’t have multiple homes, we don’t have multiple supercars. But we really love experiences. We did a lot of traveling, even when our kids were still in strollers. Those are the things that we really like doing.

“You find out what you want sooner or later. What I wanted was enough. Enough financially to then have everything else I wanted. And what I want is to hang out with my kids, travel with my wife, build old classic cars, and ride mountain bikes.”

If you create enough leverage from your product, your team, and your business model, you can have a great software business AND a great life at the same time. You don’t have to choose one or the other, in many cases.

But you do need to choose to stay off big outside funding to do that. Big VC funding means betting your business AND your life for a potential prize much later. You can’t take profits now and slow your growth a little to do that.

Joshua now calls himself happily RETIRED. And I believe him.

That’s just one way to do it that works for some founders. It’s not the only way to do it or the best way for everyone.

Listen to this podcast interview with Joshua Strebel at practicalfounders dot com or use the link in the comments below.


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