Holly O’Brien, Founder of SkillZilla: Closing the Life Skills Gap for the Next Generation

Please share a brief introduction about yourself and your business

I’m Holly O’Brien, founder and CEO of SkillZilla. As a mom of six boys and someone who’s navigated everything from dropping out of high school to building startups, I know firsthand how crucial real-life skills are for young people. My journey as an entrepreneur started after watching my own teenagers struggle with basics like budgeting, which inspired me to invest my life savings into creating SkillZilla.

SkillZilla is an EdTech startup on a mission to make life skills education fun, practical, and accessible for every young adult. We use gamified lessons, a playful dinosaur theme, and real-world rewards to help teens and young adults (ages 14–24) build confidence and master the essentials like financial literacy, communication, and wellness. Our goal is to close the life skills gap and unlock brighter futures for the next generation.

Who are your customers?

Our customers are primarily parents, educators, schools, and organizations who want to empower young adults (ages 14–24) with essential life skills. We also serve angel investors and community partners interested in social impact and youth development.

On the user side, our direct audience is tech-savvy teens and young adults, especially those aged 17–21, who are looking for practical, engaging ways to build real-world skills. We have a strong focus on supporting underserved groups, including neurodivergent youth, foster and formerly incarcerated youth, and survivors of trafficking, through partnerships with schools and nonprofits.

What was your background prior to starting your own business?

Before starting SkillZilla, my background was a mix of real-life challenges and diverse work experience. I dropped out of high school at 17 because I felt traditional education wasn’t preparing me for the real world. I became a mom at 18, married young, and by 25 I was divorced with four kids. I worked my way up from waitressing jobs to earning six figures in the startup world, but also experienced the instability of layoffs... twice.

These experiences, especially watching my own kids struggle with basic life skills, inspired me to invest my life savings and create SkillZilla. My journey is all about resilience, learning by doing, and a deep passion for helping the next generation get the practical skills they need to thrive.

What made you take the leap to start your own business?

What really pushed me to take the leap was a moment watching one of my teenage sons struggle with something as basic as budgeting. As a mom of six boys, I kept seeing firsthand how schools weren’t teaching the real-world skills kids actually need due to lack of resources. Then I pointed the finger at myself and asked why I didn't teach them. The honest truth? I was working a fulltime job and side hustle to make ends meet. I simply didn't have the time or energy. I knew I couldn't be the only one. That frustration, and honestly, a sense of responsibility, lit a fire in me. "See a need, fill a need." -Robots I realized if I wanted things to change, I had to do something about it myself. So I invested my life savings and poured everything I had to build SkillZilla. I wanted to create a solution that would genuinely help young people build confidence and thrive, not just in school, but in life. That personal connection and passion for helping the next generation is what made me go all-in.

Did you always know you wanted to be an entrepreneur?

Did I always know I wanted to be an entrepreneur? Nope, not at all. But what I did know, even early on, was that I absolutely hated having my time wasted by other people. If you’ve ever had a job, you know how much time gets chewed up just following directions that aren’t even efficient, they’re just there to cover someone’s butt. I never liked being ordered around or told when to show up, and I’ve always had a personality that just isn’t built for working for someone else. Every job I’ve ever had, I brought an owner mentality, which I considered valuable but in reality only caused friction. Higher-ups would get nervous, thinking I was gunning for their jobs, when all I really wanted was to make things better for everyone. Turns out, bringing too many ideas to the table can make some folks uncomfortable. So, did I set out to be an entrepreneur? Not really. But I always knew I didn’t want to work for someone else, and eventually, that led me here.

Take us back to when you first launched your business; what was your marketing strategy to get the word out and did it go as planned?

When I first launched SkillZilla, my marketing strategy was all about grassroots movement and building genuine community buzz. I leaned hard into sharing my authentic founder journey on LinkedIn, being open about my real life as a mom of six, the highs and lows of startup life, and why life skills education mattered so much to me. My goal was to rally people around the mission, not just the product.

Here’s how I approached it: Facebook & Instagram: I posted daily, sharing behind-the-scenes moments, family stories, and direct asks for support. I celebrated every small win, tagged community partners, and went live at local events. I also jumped into Facebook groups, offering value and sharing my story to connect with parents and educators. SkillZilla Stories: I started a testimonial drive to highlight real user experiences, which helped build credibility and word-of-mouth. Weekly Mission-Driven Messaging: I kept the focus on our “why”, closing the life skills gap, and rotated calls-to-action to keep things fresh and inclusive.

Did it go as planned?

Honestly, yes and no. The authentic approach helped us build a loyal early audience and some amazing partnerships, but it was a slow burn—getting real traction took longer than I expected. There were definitely challenges: building partnerships, converting awareness into paying customers, and navigating the legal stuff. But the grassroots, founder-led approach laid a strong foundation and kept our mission front and center, which I wouldn’t trade for anything.

What is the biggest challenge you have encountered along the way so far and what have you learned from it?

The biggest challenge I’ve faced so far with SkillZilla has been getting customers, building strong partnerships, and navigating all the legal hurdles that come with launching an EdTech startup. Honestly, it’s been a lot harder than I expected to turn early excitement into actual users and paying customers, especially with limited resources and no big marketing budget.

What I’ve learned from this is that relationships and persistence are everything. Building trust, whether with parents, educators, or partners takes a lot of time and genuine effort. I’ve also realized that being flexible and willing to pivot is key; sometimes the path you thought would work just doesn’t, and you have to try new strategies, ask for help, and keep showing up even when things feel overwhelming.

Most importantly, I’ve learned that staying true to the mission, making life skills accessible and fun for young people, keeps me going, even when the business side gets tough. Every small win, every piece of feedback from a parent or student, reminds me why I started and helps me push through the challenges.

What accomplishment are the most proud of to date in your business?

The accomplishment I’m most proud of so far is building SkillZilla from the ground up, starting with just an idea and my own life savings, and turning it into a real, growing community that’s genuinely helping young people. Seeing nearly 50,000 students join our interest list for the upcoming school year and hearing honest feedback from beta users who say our app is making a difference in their confidence and life skills, that’s huge for me.

I’m also proud of the partnerships we’ve built with organizations serving underserved youth, and of the fact that we’ve managed to keep everything mission-driven, fun, and authentic despite all the challenges. Every time a parent or student tells me SkillZilla made their life a little easier or helped them learn something important, it feels like a win worth celebrating.

Do you have any recent wins from the last year that you'd like to celebrate with our community?

I’m beyond excited to share that in the month of May, SkillZilla grew by an unbelievable 2,500%! That’s not a typo! We’ve seen explosive growth, and it’s all thanks to the support, feedback, and energy from our amazing community. This kind of momentum tells me that young people, families, and educators are hungry for real-life skills education that actually makes a difference. Every new user, every partnership, and every bit of word-of-mouth helps us move closer to our mission of unlocking life skills for the next generation.

What's next for your business? What can we expect to see over the next few years?

First up, we’re focused on scaling our user base, our immediate goal is to get 10,000 young people actively learning and building confidence through the SkillZilla app by the end of 2025. We’re rolling out new gamified courses, more real-world rewards, and expanding our community features to make learning life skills even more engaging and supportive.

You can also expect to see more partnerships with schools, nonprofits, and organizations that serve underserved youth. We’re building out our enterprise offerings and aiming to become the go-to platform for life skills education in both the U.S. and abroad.

And, of course, we’ll keep listening to our users, teens, parents, and educators, to make sure SkillZilla keeps evolving in ways that really matter. So, more features, more impact, and a bigger, global SkillZilla community are all on the horizon!

What is your top productivity tip? 

My top productivity tip is to ruthlessly prioritize and break big tasks into small, manageable steps. I’ve learned (especially as an AuDHD founder and mom of six!) that it’s easy to get overwhelmed by a massive to-do list, but if you focus on what truly moves the needle and tackle one bite-sized piece at a time, you’ll actually make progress without burning out. I rely on tools like Google Calendar and Monday.com to keep everything organized, but the real magic is in setting clear priorities for each day and giving yourself permission to let the non-essentials wait. Progress over perfection, always!

On the flip side, how do you avoid burnout?

Love this question! Honestly, avoiding burnout is all about making space for the things (and beings) that recharge you. For me, that means taking intentional breaks, snuggling with my cats, squeezing in some Xbox time, and hanging out with the hubster. Those little pockets of joy and connection are what keep me grounded when things get hectic.

I also try to protect my downtime as seriously as I do my work time. Whether it’s a quick gaming session, a cozy cuddle, or just zoning out with my favorite people (and pets), those moments help me reset so I can come back to work with more energy and creativity.

What is your approach to work-life balance / integration?

For me, there’s really no such thing as perfect “work-life balance”, it’s more like work-life management, and it’s always shifting. Sometimes work needs more from me, and sometimes my family (or my own sanity) takes the front seat. It’s about knowing what’s most important in that moment and being okay with the trade-offs.

I actually dislike the term “work-life balance” because it sets up this expectation that you should always have everything perfectly in sync, and if you don’t, you’re somehow failing. That’s just not real life, especially as a founder. There are times when I miss dinner or work late, but I make sure those moments have real value and aren’t just busywork for the sake of it. At the end of the day, it’s about prioritizing what truly matters to me and my people. There’s no shame in the hustle, and there’s no shame in stepping away when you need to. The “balance” is just doing what’s needed for the top priority at any given time, whether that’s home, work, or a little bit of both.

What is one thing you wish you had known when you started your Entreprenista journey?

Honestly, the one thing I wish I’d known when I started my Entreprenista journey is that no one actually has it all figured out. It’s so easy to look at other founders or business owners and assume they have some secret playbook or endless confidence, but the truth is—we’re all just figuring things out as we go.

There’s no perfect roadmap, and everyone is facing their own challenges behind the scenes. The real magic happens when you stop waiting to feel “ready” and just start moving forward, even if it’s messy or uncertain. Trusting yourself, staying flexible, and learning as you go is way more important than pretending to have all the answers.

When hiring, what is your go-to interview question?

What's your favorite dinosaur and why?

Are you a Mamaprenista? If so, please share your best advice for simultaneously managing a business and a family

Don’t be afraid to ask for help, whether that’s leaning on your partner, getting the kids involved, or outsourcing where you can. And remember, it’s okay if the house is messy or dinner is takeout sometimes. Progress over perfection, always.

Finally, keep your sense of humor handy and celebrate the small wins, both at home and at work. You’re setting an amazing example for your kids just by showing up and building something you believe in.

Do you have a co-founder? If so, how did you find the right one for you and what are your best partnership tips?

Yes, I do have co-founders! My husband, Daniel O’Brien Jr., is my co-founder and our COO at SkillZilla—we’re partners in both life and business. We also brought on Stephanie Brooks as our CMO; I actually found her through LinkedIn after connecting over our shared passion for youth education and life skills.

As for finding the right co-founders, it really came down to shared values, complementary strengths, and a willingness to have honest conversations (sometimes the tough ones!). With Daniel, we already had a foundation of trust and a deep understanding of each other’s strengths and quirks. With Stephanie, I was drawn to her energy, expertise, and how naturally our visions aligned.

My top partnership tips: Be radically honest, even when it’s uncomfortable. Communication is everything, especially when things get tough. Clearly define your roles and responsibilities so everyone knows what they own and where to step in. Celebrate wins together, but also support each other through setbacks. Startups are a rollercoaster, and you need people around you who can ride the highs and the lows.

Respect each other’s boundaries and differences. You don’t have to agree on everything, but you do need to trust and value each other’s perspective. Check in regularly—not just about business, but about how you’re both feeling. The human side matters just as much as the business side.

If you’re looking for a co-founder, focus on finding someone who shares your mission, isn’t afraid to challenge you, and is in it for the long haul. And if you’re already in a partnership, keep those communication lines open and don’t forget to have fun together!

What's the one app on your phone you absolutely cannot live without and why?

Love this question! Honestly, the one app on my phone I absolutely cannot live without is the “I Am” affirmations app. As a founder, mom, and someone who’s constantly juggling a million things, I need those little reminders to stay grounded and keep my mindset positive. The app sends me daily affirmations that help me reset, refocus, and remind myself why I’m doing what I do, even on the tough days. It’s like a tiny dose of encouragement right when I need it most!

What is your favorite business tool or solution and why?

My favorite business tools, hands down, are Slack and Monday.com. Slack keeps my team connected, organized, and moving fast, whether we’re sharing quick updates, celebrating wins, or just checking in. It makes remote work feel way more personal and collaborative.

Monday is our go-to for project management and keeping everything (and everyone) on track. I love how visual and customizable it is. It helps me see the big picture, track progress, and make sure nothing falls through the cracks,especially with so many moving parts in a startup. Honestly, I’d be lost without both of them!

What advice do you have for aspiring Entreprenistas?

My top advice for aspiring Entreprenistas is to expect to pivot, probably more than once. The path you start on is almost never the one you end up following, and that’s completely normal. Flexibility and a willingness to adapt are your superpowers.

Also, be intentional about building your team and advisory board. Surround yourself with a mixed bag of people: different backgrounds, perspectives, and skill sets, not just folks who always agree with you. An echo chamber might feel comfortable, but real growth and innovation come from being challenged and seeing things from angles you’d never think of on your own. So: Stay open, stay curious, and don’t be afraid to shake things up. Your best ideas (and biggest breakthroughs) will often come from the unexpected!

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