We’re excited to introduce you to the always interesting and insightful Chelsea Borruano. We hope you’ll enjoy our conversation with Chelsea below.

Chelsea, thanks for joining us, excited to have you contributing your stories and insights. Risking taking is a huge part of most people’s story but too often society overlooks those risks and only focuses on where you are today. Can you talk to us about a risk you’ve taken – it could be a big risk or a small one – but walk us through the backstory.

In my early 30s, I made the decision to go back to school to become a therapist after building a career in marketing. It was 2020 and I was trying to sell marketing services to companies who were trying to keep the doors open. So I quit. I started freelancing for nonprofits and putting a lot of energy in grad school while also starting a nonprofit for mental health and art. Now, after solo traveling for two years, I moved to San Francisco to build InsightsOut, a startup to help us connect more deeply with ourselves, each other, and humanity. And what I keep learning is that the risks are worth it.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m the co-founder and CEO of InsightsOut, where we’re building emotional awareness for the age of AI. Alongside that, I work in marketing helping mission-driven organizations tell their stories and run the You Aren’t Alone Project, a nonprofit using creative expression to support mental health.

My path here started with my own battle with depression and anxiety. When I found the support I needed, I also found a passion for doing this work. So when I met my now cofounder in Mexico while we were both solo traveling and he told me he was building a tool to help people navigate their therapy sessions, I was all in.

What started as a therapy companion app has shifted and grown to emotional learning for real life. Through our discovery process, talking to users, testing ideas, and understanding what people were actually looking for, we kept hearing that people wanted more insight into their emotions.

We’re now building a community and tools that help people practice emotional awareness as a daily skill.

We work with individuals through our app and community workshops and with founders and teams who want to better understand the emotional dynamics that shape trust, communication, and decision-making in their organizations.

What sets us apart is our focus on real-world application and our community at the heart of it all. We’re trying to helping people actually notice and work with their emotions instead of against them so they can bring those practices to their lives, work and relationships.

Any advice for managing a team?

At InsightsOut, we try to lead with emotional awareness as a practice. That means creating space for people to show up as humans first.

We start meetings with emotional check-ins. These check-ins aren’t just a way to connect. We also get energy from the practice that generates creativity and motivation. We build in acknowledgements to the end for sharing what we see in the other person. What I’ve learned is that morale isn’t something you fix after the fact. It’s something you build through consistent, small practices. When people feel safe, seen, and understood, they’re naturally more engaged, more collaborative, and more resilient through challenges.

A big part of this also comes from how we operate as co-founders. We prioritize trust and vulnerability in that relationship, which sets the tone for the rest of the team. Being open about fears, naming tensions early, and not pretending to have everything figured out creates permission for others to do the same.

How do you keep in touch with clients and foster brand loyalty?

A big part of that is the community we’re creating. Through workshops and live experiences, we’re building space for people to connect with their emotions alongside others. That shared experience builds a different level of connection, both to the work and to each other. That’s something I really learned leading the You Aren’t Alone Project.

Across all of this, we’re constantly listening. Whether it’s through direct conversations, product feedback, or how people engage in workshops, our community members are co-creators in what we’re building. A lot of the evolution of InsightsOut has come from really seeing people.​​​​​​​​​​​​​​​​

Partnerships are another important layer. We work with aligned organizations and communities to bring this work into different contexts, whether that’s teams, founders, or broader networks. It allows us to meet people where they already are, rather than expecting them to come to us.

Contact Info:

• Website: https://www.insightsout.app/
• Instagram: alongthegravelroad
• Linkedin: https://www.linkedin.com/in/chelseaborruano/
• Youtube: https://www.youtube.com/@insightsout-app