Caitlin Iseler, Founder and CEO of Happyly, is on a mission to inspire physical and mental wellness for working parents by providing ideas for personalized outdoor experiences.
After spending 15 years working in the technology industry, Caitlin decided to harness her talents to bring value to families. The Happyly app encourages families to step away from their screens and safely into the world to experience outdoor activities in less than 60 seconds. Through founding Happyly, Caitlin has learned the importance of celebrating the smaller wins and moving at a slower pace to ensure the long-term success of her company.
We asked Caitlin about the hardest and most rewarding part of her journey, how she celebrates her success along the way, and what’s next for Happyly.
Q: What makes Happly different from other platforms?
A: We built an app designed to get you off your screen and safely into the world to experience the physical and mental health benefits of being outside with those who matter most. Our entire UI is about 60 seconds or less. People are busy, especially working parents, and everything we do is built around making parents more productive so that they can find those micro-wins in everyday life.
Q: What’s been the hardest and most rewarding part of your entrepreneurial journey?
A: The most rewarding is definitely how united we are on the value of this mission. The Happyly team and the extended community that we have had the privilege of working with share immense enthusiasm for making outdoor exploration more accessible for all. I never imagined how many inspiring people would raise their hand to join us on this journey—it makes my heart smile every day.
Q: How do you celebrate successes along the way?
A: This is one of my favorite things to do. It’s easy to admire our company crushes, such as Rent the Runway, All Trails, and Class Pass at this stage, and underestimate all of the wins and challenges they experienced along the way. The snapshot we saw of Whitney Wolfe with her adorable kiddo on The New York Stock Exchange was an exhilarating moment. But I understand now that it comes with lots of lows and small wins along the way. While we grasp for big wins, those little wins are what make the journey worthwhile. A positive email from a corporate partner, a happy member returning from a family trip we helped plan, watching our team share our message with such obvious enthusiasm, and working with people that deeply support one another—that’s the good stuff!
Q: How have you grown as a leader since starting Happyly? What experiences have contributed to this growth?
A: I’m learning the value of patience every day. Accustomed to a client support role from my days in executive search at Korn Ferry, I operated from a reactionary place and always moved deliberately fast. While this maintains its value, I’m learning that sometimes moving slowly in order to carefully evaluate our choices is often just what we need. I’m not perfect, but I’m trying to be more patient with the speed of growth, others, and myself.
Q: What’s next for you and Happyly?
A: We will begin the process of an institutional fundraising round in the coming months as we continue to demonstrate proof of concept. This raise is important for a million reasons and our biggest consideration is finding the right partner with whom we align on values, our goals around impacting families, and, of course, financial opportunity.
Caitlin is a member of Dreamers & Doers, a private collective that amplifies the entrepreneurial pursuits of extraordinary women through thought leadership opportunities, authentic connection, and access. Learn more about Dreamers & Doers and subscribe to their monthly The Digest for top entrepreneurial and career resources.
The views and opinions expressed herein are the views and opinions of the author and do not necessarily reflect those of Nasdaq, Inc.