• Greg Smith started tutoring the LSAT in law school.
• He automated a course and out-earned his lawyer salary selling it.
• He grew and scaled a learning platform that now generates $75 million in annual revenue.

This as-told-to essay is based on a conversation with Greg Smith, CEO of Thinkific. It has been edited for length and clarity.

I became interested in corporate law because of the role lawyers play in pivotal business decisions. As a CEO, I might navigate a merger or IPO only once or twice, but as a corporate lawyer, I'd be dealing with them constantly. It seemed to me there were more exciting corporate transactions in a few years of corporate law than there were in two lifetimes of being a CEO.

That pushed me to go to law school. While there, I started tutoring for the LSAT to help pay my bills, including student loan payments. I realized that a lot of my tutoring was repetitive, but I was limited by how many students I could fit into a room. I wanted to reach more people, have more impact, and generate more revenue.

So, in 2005, I launched an automated course. The course started generating thousands of dollars a month, without me investing much time or money. Once, when I had a month of my law job, I really focused on promoting the course, and it generated $10,000 in a month — more than I was making in my corporate role. That was a real signal that I should go deeper with this.

Soon, others asked me to help build their course platforms

I had always been drawn to entrepreneurship — probably because my parents were always thinking about their big ideas, but never able to follow through because of their day jobs. One time, on a plane ride, I had an aha moment: I needed to build a business.

I didn't immediately think about my course. Instead, I left my lawyer job for another startup opportunity, but that didn't pan out.

As I considered my options, I realized that other people and companies were already approaching me about helping them create a platform to support their own educational courses. I had inbound leads, and the solution they were looking for, so I decided to give it a try. In 2012, I founded Thinkific.

My brother was a cofounder, but we often butted heads

My brother Matt, who is eight years younger, saw me struggling to write code. He stepped in to help and became a cofounder. In the early days, there was a fair amount of healthy and unhealthy conflict between us in the office. We were driven and wanted to reach the same place, but we had different ideas about how to get there.

We both wanted to be the CEO — the one making major decisions. But in reality, there weren't that many decisions to be made. After three years of working together, Matt left to pursue another idea. Although we'd had disagreements at work, we always got along well on the weekends.

As Thinkific continued to grow and scale, Matt became one of my most trusted advisors. He briefly rejoined the company as Chief Strategy Officer, and our dynamic was very different. The company was growing so fast that we had tons of decisions to make, and I was grateful for anything he could take off my plate. Today, he's an advisor to the board. He's also the guy I can call when I'm struggling, just to talk.

I teach my kids to be proud of their failures

My kids are 7 and 10, and I talk to them a lot about failure. When my daughter was about 3, she asked what failure was. I told her that when something doesn't go the way you want, it's a huge opportunity.

Now, I'll regularly ask the kids about the things they failed at, to show them they should be proud of their failures. They love talking about it so much that they'll tell other kids, "You failed!" like it's the most exciting thing. Sometimes other parents give me the side eye about that, but I'm glad that their approach to failure is healthy — that will help them when they're trying new things.

• Jay Zigmont has been married for 17 years and has no kids.
• He rents his home because he and his wife move frequently.
• He's unlikely to retire fully, but likes a more fluid approach to work.

This as-told-to essay is based on a conversation with Jay Zigmont, founder of Childfree Wealth and Childfree Trust. It has been edited for length and clarity.

I wear a shirt when I want to start conversations. It says, "Proudly childfree and wealthy."

At financial conferences, it stops people in their tracks and gives me an opportunity to talk about my work helping childfree people make estate plans that match their lives.

My wife, Vicki, and I have been married for nearly 17 years. Because of a health condition she has, we always knew we wouldn't have kids. It's shaped everything about how we approach life, including our ideas about our careers, finances, retirement, and even home ownership.

Vicki is Catholic, and wanted to get married in the Catholic Church, but they wouldn't marry us if we didn't plan to have children. We asked three different churches, and all had the same answer. We got married at my Methodist church, and that was the first time we realized how much being childfree would impact all areas of our lives.

I'd like to die with very little money, not acquire more wealth

I'm 48, but in my late 30s, I had achieved my career and financial goals. I had $1 million in the bank and no debt, but I didn't know where to go from there.

As a childfree person, there's a point when you can have too much wealth. I'm not trying to build generational wealth — in fact, I'd like to die with very little money. That means my career isn't driven by financial gain. I focus on purpose, not profit.

Whatever Vicki and I have when we die will be left to our nephews, but I hope it's not much. Instead of leaving them a large sum later in life, we're supporting them when they need it most. We contribute to their college funds, and I would be happy to consider investing in their businesses or helping them buy a house. We also give generously to charities — my personal favorite is a charity that buys and forgives medical debt.

I likely won't ever retire fully

I plan to always work in some way. Instead of focusing on early retirement, I follow a FILE approach: "financial independence, live early." I want to work on projects I enjoy, but do so on my own time, from anywhere.

When you don't have kids, you have to reimagine the typical idea of success and what life can look like. That can take months, because you're untangling a lifetime of messaging, to figure out what you truly want.

I encourage people to think about this by writing their obituary. Mine would say something like "loving husband, world traveler, author, and innovator." Those are the things I want to focus on — not building wealth for wealth's sake. A few years ago, I tried my hand at maple syrup farming just because it sounded enjoyable.

My legacy will be helping other childfree people

Vicki and I rent our home, and although we've owned in the past, I don't think we ever will again. We move often, every two to three years, since we're not tied to a specific school system or living near family to help watch the kids. Renting saves us money, and I think it's usually the right move for most childfree people.

Recently, Tennessee, where I live, passed a bill requiring students to learn about the "success sequence": graduating, getting a job, getting married, and having kids. We're taught so much about that one path to success, but there are more options.

My legacy won't be children, but rather helping other childfree people find the success sequence that's right for them.

• Many tech leaders say they're ditching screen time limits, though some still use them.
• Instead, they're focused on how their kids are interacting with technology, prioritizing creativity.
• Short-form video and social media remain major concerns for many parents.

These days, parenting means navigating a seemingly endless parade of decisions about technology. Can your toddler watch "Sesame Street" on an iPad? Does FaceTiming the grandparents count toward screen time? Should your teen have access to social media just because "everyone else" seems to?

Parents are more cognizant than ever about the pitfalls — and potential — of technology, so it's natural to wonder how the people leading tech companies handle this with their own kids. Paypal cofounder Peter Thiel and Snapchat CEO Evan Spiegel have both said they limit their young children (all 8 or under) to an hour and a half of screen time per week. Facebook founder Mark Zuckerberg has said that he wants his kids to use screens for communication, not passive consumption.

It turns out, tech leaders, for the most part, are like the rest of us: trying to balance screen-free time and critical thinking skills, while also giving their kids access to the world that technology can unlock.

Here's how seven tech leaders are handling technology decisions for their families.

Finding the middle

Kate Doerksen is the co-founder and CEO of Sage Haven, an app that helps parents monitor their kids' messaging. Her kids, who are 7 and 9, get an hour per day on their iPads or Nintendo Switch, plus additional time if the family is playing a video game together. She plans to delay smartphones and social media, but her daughter has an Apple Watch with messenger (which Doerksen monitors).

"Like most things in life, the right answer feels like it lies somewhere in the middle," Doerksen says. "It's not tech abstinence, and it's not unlimited, unfettered usage. It's moderate usage on non-addictive apps and games with boundaries."

Learning and creating

As the chief learning officer at the online education company Stride, Niyoka McCoy, sees tech as a normal part of life, but she's still intentional about how her children — who are 14 and 2 — use it.

"We believe technology should be a tool for learning and creativity first, and entertainment second," she says. Her kids don't have hard-and-fast screen time limits, but McCoy aims to avoid them passively consuming content.

"When kids spend too much time scrolling or watching instead of creating, learning, or building something meaningful," she says, "that is when technology stops being beneficial."

Focusing on well-being, not screen time

Three years ago, Hari Ravichandran's daughter, who was then 13, went through a tough time — one that he believes her access to a smartphone contributed to. He had given her a phone at 13, but now believes that was too young, so he decided to take the phone away and delay access until 15 or 16 for her as well as his three younger children.

"I knew we couldn't just send her back into the same digital environment that had amplified those issues," said Ravichandran, the founder and CEO of online security company Aura.

At the same time, "What I think is overblown is the idea that technology itself is the enemy," Ravichandran says. "Cutting it out completely doesn't solve the root problem and can actually limit kids' independence and digital literacy."

Today, he focuses on how technology impacts his children's mood, sleep, self-esteem, and overall well-being.

"For us, it's less about strict bans and more about awareness, accountability, and open dialogue," he says.

Making sure values align

Tim Sheehan, co-founder and CEO Greenlight — which provides debit cards for children and teens — gave his four kids access to smartphones at 12, and social media at 15. His kids now range in age from 17 to 26. When they were younger, he watched their tech consumption closely, knowing how impressionable they were.

"My goal is to make sure the outside influences in their lives support the values we're trying to instill," he says.

Limiting short-term video

Justice Eroline, chief technology officer at the software development firm BairesDev, has a blanket rule of 1 hour of screen time for his kids, who are 8, 10, and 12. Even within that, he pays close attention to the type of content they're watching.

"I don't allow short-form content for the kids as it affects their attention span," he says.

Ahu Chhapgar, chief technology officer at fintech company Paysafe and dad of two (ages 10 and 13), says short-form video worries him more than anything else.

"When kids get access to it, they almost enter a trance," he says. "That level of stimulus is not how the brain evolved to process information, and I do worry about long-term effects on attention and impulse control."

Allowing AI, and gaming

Unlike some parents, Eroline is much less concerned about gaming.

"Video games can teach kids a lot of different things: teamwork, reaction time, problem solving, grit, dealing with defeat," Eroline says. "The content of the video game might be questionable, but there are plenty that can work for different age ranges."

Chhapgar won't let his kids have access to smartphones until they're 14, and social media until they're 16, but he does encourage them to use ChatGPT for 20 minutes each day.

"No one has all the answers about AI yet," he says. "So I'd rather they explore, build, and experiment responsibly instead of just passively consuming technology."

Controlling the interaction

Nik Kale, principal engineer with Cisco Systems, makes sure that his 3-year-old isn't given a screen when she's upset.

"I don't want her building a dependency where the first response to discomfort is a device," he explains.

He also ensures that he or his wife — not an algorithm — are choosing what their daughter sees.

"I don't let automated systems make unsupervised decisions in my production environments at work," he says. "I'm not going to let one make unsupervised decisions about what my three-year-old's brain consumes either."

That, to him, is much more important than seemingly arbitrary screen time limits.

"Parents are adding up minutes like it's a toxicity dosage," he says, "when the real variable is whether a human or an algorithm is driving the experience."