Trilogy

How two second-time founders are tackling one of the most pressing issues facing modern families

If you’ve ever stood on the sidelines of a soccer game or attended a school event lately, you’ve probably overheard the conversations. Parents huddled together, voices tinged with concern, discussing the same thing: their kids’ digital lives. It has become the number one, two, and three issues that parents are grappling with today.

For Karl Stillner and Steve Dossick, co-founders of BrightCanary, these weren’t just overheard conversations—they were a daily reality as fathers themselves. And as seasoned technologists who had just sold their previous company, PushSpring, to T-Mobile, they found themselves uniquely positioned to tackle this growing problem.

When Water Cooler Talks Turn Into Business Ideas

“There was a lot of water cooler talk when we were at T-Mobile,” Karl recalls about their time at the telecom giant after their acquisition. Both entrepreneurs were eager to return to the startup world. However, it was their personal experiences as parents that sparked their next venture.

Steve, father to soon-to-be 16-year-old twins, and Karl, with 14-year-old and 11-year-old children, were constantly discussing the challenges of guiding their children through the digital world. “How do you stop them from going to see the wrong thing on YouTube?” was just the beginning. As their kids got older and gained access to more platforms and devices, the challenges multiplied.

What frustrated them most as technologists was the lack of pragmatic solutions. The existing “command and control” software could tell parents when their kids used devices and which apps they accessed, but provided zero insight into what children were actually doing within those apps.

“They used iMessage for two hours. Well, what did they do inside iMessage for two hours? What did they watch on YouTube?” These were the questions keeping parents up at night, and the market had no good answers.

A Different Approach to Digital Parenting with BrightCanary

BrightCanary’s philosophy represents a fundamental shift from first-generation parental control solutions. Instead of focusing on blocking and preventing access—an approach the founders believe is “antiquated” in 2025—they’re focused on keeping parents informed about what their children are actually doing online.

“Kids have devices at school, they have devices on the bus, they have devices everywhere,” Karl explains. “This notion of being able to prevent kids from using the internet doesn’t make sense today.”

Their technological approach differs significantly from that of their competitors. Rather than relying solely on VPN or Mobile Device Management (MDM) solutions, BrightCanary uses multiple complementary technologies to cast a wider net, enabling more comprehensive monitoring across the services kids actually use.

Importantly, they’ve built their solution with iOS as a primary focus. In the US, 87% of kids use iOS devices, yet most existing solutions concentrate on Android due to technical limitations. This focus has enabled BrightCanary to address the market where users are located.

The AI Advantage

Being “10 to 15 years later” to market than their competitors has actually worked in BrightCanary’s favor. They’ve been able to integrate AI from day one, rather than bolting it on as an afterthought.

The difference is significant. Previous generations of monitoring tools relied on off-the-shelf machine learning models designed for large companies hosting user-generated content—essentially built to detect obvious violations, such as pornography. These models struggle with the way kids actually communicate online, often using snippets, incomplete sentences, and text message-style language.

“LLMs, because they’re just more fluid with written content, are much better able to understand the meaning and emotion behind communication that is written in snippets,” Steve notes. This AI-first approach has become a major differentiator, particularly as the company has learned that messaging—not just content consumption—is where parents’ greatest concerns lie.

The Messaging Revelation

One of BrightCanary’s most important early learnings was discovering that parents were more concerned about unmoderated messaging between kids than about content consumption. This insight took 12-15 months to fully understand and required a change in their technology approach.

“Instagram is a messaging app. Snap is actually a messaging app,” Steve points out. While these platforms have robust content moderation for public posts, direct messages remain completely unmoderated—creating what Steve calls “the Wild West.”

The numbers are staggering: the average kid on BrightCanary’s platform sends and receives over 1,000 messages per day. With children spending upwards of six to seven hours daily on non-school digital activities—the majority of their waking hours outside school—parents were operating completely blind to what was happening in this crucial part of their kids’ lives.

Beyond the Tech-Worker Stereotype

When BrightCanary launched, the founders hypothesized their market would primarily consist of tech workers and high-income households—essentially people trying to solve a problem they’d helped create. They were wrong.

“That particular segment under indexes, and we see much more over-indexing in the Midwest, in the South, across faith-based organizations, across military backgrounds,” Karl reveals. The customer base has proven to be extremely broad, reflecting what many have noted: this is a bipartisan, non-political issue affecting families everywhere.

The universality of the problem extends internationally as well, though the founders believe the US is at the forefront due to earlier device adoption among children.

Building Culture in a Remote World

As second-time founders, Karl and Steve have developed specific strategies for building company culture, especially in a post-COVID remote environment. They prioritize hiring people who understand and align with their mission. The majority of their employees have kids, and even those who don’t have personal connections to the problem they’re solving. “We can’t pay as well as Amazon can, we work harder than they do in a lot of ways, but if they’re not aligned with the mission, they’re not going to be able to do this long term,” Steve explains.

They’ve also found success hiring developers with “alternative backgrounds”—people who might be overlooked by large tech companies but bring strong skills and diverse perspectives to the team.

The Road Ahead

Looking forward, BrightCanary sees a significant opportunity in the growing digital literacy among both parents and children. Children aged 13-16 are becoming increasingly aware of the costs associated with digital overuse and are seeking greater autonomy in managing their digital lives.

The company envisions a future where they serve parents of children aged 8-14, then graduate those kids into a service that puts them in the driver’s seat—an AI-driven companion that’s entirely context-aware of their digital life, providing trusted, objective, and private guidance as they navigate the online world independently.

Lessons for Fellow Entrepreneurs

For other entrepreneurs considering the leap, Karl and Steve emphasize several key points:

• Enjoy the journey: “Entrepreneurs need to have fun doing this. It’s far too stressful to do without having a notion of enjoying it.”
• Find the right partner: Having a co-founder you trust and work well with makes the journey “a lot less lonely and a lot more enjoyable.”
• It takes longer than you think: They’re now on their third iteration of the product, each building on the learnings from the previous version.
• Don’t rush product-market fit: “Don’t rush the product market fit phase and get the product right. The go-to-market will be that much easier if you’ve nailed the product-market fit.”
• Choose your investors carefully: Focus first on who you’ll be working with as individuals, not just the financial terms or firm reputation.

The BrightCanary Mission Continues

For Karl and Steve, BrightCanary represents more than just another business opportunity. They regularly receive feedback from parents about how they’re helping them raise their children and have “averted all kinds of terrible situations.” This mission-driven approach helps make the inherent challenges of building a B2C business—from longer paths to profitability to the complexities of market creation—more manageable.

As Jonathan Haidt’s “The Anxious Generation” remains on the New York Times bestseller list for its 67th week, it’s clear that the problem BrightCanary is solving isn’t going anywhere. In fact, with digital usage among children having doubled during COVID and never returning to pre-pandemic levels, the need for solutions like theirs has never been greater.

The company’s journey from water cooler conversations to helping parents navigate one of the most challenging aspects of modern child-rearing demonstrates how personal experience, technological expertise, and a genuine mission to help can come together to create meaningful solutions to real-world problems.

To hear the full conversation with Karl Stillner and Steve Dossick, including more insights on their entrepreneurial journey and building BrightCanary, subscribe to the CLOUDBREAK podcast on Apple, Spotify, or wherever you get your podcasts.